CA2585557C - Nouveaux composes pharmaceutiques - Google Patents

Nouveaux composes pharmaceutiques Download PDF

Info

Publication number: CA2585557C
Authority: CA; Canada
Prior art keywords: ethyl; pyrimidin; pyrazolo; amine; ethoxyethyl
Prior art date: 2004-10-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002585557A

Other languages

English (en)

Other versions

CA2585557A1 (fr

Inventor

Brad Alan Acker

Robert Owen Hughes

Eric John Jacobsen

Hwang-Fun Lu

Thomas Edward Rogers

Michael Brent Tollefson

John Keith Walker

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co LLC

Original Assignee

Pharmacia and Upjohn Co LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2004-10-28

Filing date

2005-10-17

Publication date

2009-08-18

2005-10-17 Application filed by Pharmacia and Upjohn Co LLC filed Critical Pharmacia and Upjohn Co LLC

2006-05-04 Publication of CA2585557A1 publication Critical patent/CA2585557A1/fr

2009-08-18 Application granted granted Critical

2009-08-18 Publication of CA2585557C publication Critical patent/CA2585557C/fr

2025-10-17 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000002590 phosphodiesterase V inhibitor Substances 0.000 title abstract description 7
229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 title abstract description 5
APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title description 3
238000002360 preparation method Methods 0.000 claims abstract description 415
150000001875 compounds Chemical class 0.000 claims abstract description 414
-1 cyclic guanylate monophosphate Chemical class 0.000 claims abstract description 274
238000011282 treatment Methods 0.000 claims abstract description 32
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 195
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 151
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 60
150000003839 salts Chemical class 0.000 claims description 34
239000012453 solvate Substances 0.000 claims description 20
239000003814 drug Substances 0.000 claims description 13
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 10
101100296726 Caenorhabditis elegans pde-5 gene Proteins 0.000 claims description 9
230000009286 beneficial effect Effects 0.000 claims description 5
230000005764 inhibitory process Effects 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 3
FEIOTTPJYXBGOP-UHFFFAOYSA-N 1,3-bis(2-ethoxyethyl)-5-n,5-n-dimethyl-7-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C)N=C2C(CCOCC)=NN(CCOCC)C2=C1NC1=CC(C)=CC=N1 FEIOTTPJYXBGOP-UHFFFAOYSA-N 0.000 claims description 2
BLKCIFPIUHPNDB-UHFFFAOYSA-N OC(=O)C(F)(F)F.CCOCc1nn(CCOCC(F)(F)F)c2c(Nc3ccncn3)nc(nc12)N1CCN(CC1)C(=O)OC(C)(C)C Chemical compound OC(=O)C(F)(F)F.CCOCc1nn(CCOCC(F)(F)F)c2c(Nc3ccncn3)nc(nc12)N1CCN(CC1)C(=O)OC(C)(C)C BLKCIFPIUHPNDB-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
SOKKGTRTVOYRCX-UHFFFAOYSA-N tert-butyl 4-[7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]-3-(2,2,2-trifluoroethoxymethyl)pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2COCC(F)(F)F)C2=N1 SOKKGTRTVOYRCX-UHFFFAOYSA-N 0.000 claims description 2
NKVZUKMJXKMWCB-UHFFFAOYSA-N 1-[3-ethyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxamide Chemical compound N1=C(N2CC(CCC2)C(N)=O)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 NKVZUKMJXKMWCB-UHFFFAOYSA-N 0.000 claims 2
OQDATHXTNKTVAH-CALCHBBNSA-N 5-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)N[C@@H](C)C2)=NC=1NC1=CC=CC(C)=N1 OQDATHXTNKTVAH-CALCHBBNSA-N 0.000 claims 2
HHAULIGFDSRELR-QGZVFWFLSA-N 1-(2-ethoxyethyl)-3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC(C)=CC=N1 HHAULIGFDSRELR-QGZVFWFLSA-N 0.000 claims 1
PPPYMEOPXVUWCO-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=N1 PPPYMEOPXVUWCO-MRXNPFEDSA-N 0.000 claims 1
TUCVEIDMALGDIA-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=NC=N1 TUCVEIDMALGDIA-OAHLLOKOSA-N 0.000 claims 1
NEWAASLDNWLOOG-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-(ethoxymethyl)-n-(4-fluorophenyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=C(F)C=C1 NEWAASLDNWLOOG-MRXNPFEDSA-N 0.000 claims 1
GITXUDXPKFFWLH-QGZVFWFLSA-N 1-(2-ethoxyethyl)-3-(ethoxymethyl)-n-(6-ethylpyridin-2-yl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(CC)=N1 GITXUDXPKFFWLH-QGZVFWFLSA-N 0.000 claims 1
CNYYVKXBXUYOEY-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC(C)=CC=N1 CNYYVKXBXUYOEY-MRXNPFEDSA-N 0.000 claims 1
XXZHIDRMOCZAFT-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=N1 XXZHIDRMOCZAFT-OAHLLOKOSA-N 0.000 claims 1
HCNLOJQGOVQLQQ-CQSZACIVSA-N 1-(2-ethoxyethyl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=NC=N1 HCNLOJQGOVQLQQ-CQSZACIVSA-N 0.000 claims 1
NAKPDBFQPWAIHO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-(methoxymethyl)-5-piperazin-1-yl-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2CCNCC2)=NC=1NC1=CC=NC=N1 NAKPDBFQPWAIHO-UHFFFAOYSA-N 0.000 claims 1
UOWQVSPGTUZNLW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)-n-(3-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=NC=CC=C1C UOWQVSPGTUZNLW-UHFFFAOYSA-N 0.000 claims 1
GAZBPJSYFHKHNT-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC(C)=CC=N1 GAZBPJSYFHKHNT-UHFFFAOYSA-N 0.000 claims 1
IQTINNXJGBHZFP-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC(C)=N1 IQTINNXJGBHZFP-UHFFFAOYSA-N 0.000 claims 1
JXRFSMPVFGDABM-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)-n-phenylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC=C1 JXRFSMPVFGDABM-UHFFFAOYSA-N 0.000 claims 1
DKMYDPXRIRBRHV-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(3-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=NC=CC=C1C DKMYDPXRIRBRHV-MRXNPFEDSA-N 0.000 claims 1
DYPDWDBQCMHXIP-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC(C)=CC=N1 DYPDWDBQCMHXIP-MRXNPFEDSA-N 0.000 claims 1
WUMNVPPPDAQCCH-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyrimidin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=NC=CC(C)=N1 WUMNVPPPDAQCCH-OAHLLOKOSA-N 0.000 claims 1
CKLXBKCWYMHANC-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-phenylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=C1 CKLXBKCWYMHANC-MRXNPFEDSA-N 0.000 claims 1
DYPDWDBQCMHXIP-INIZCTEOSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3s)-3-methylpiperazin-1-yl]-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@H](C)NCC2)=NC=1NC1=CC(C)=CC=N1 DYPDWDBQCMHXIP-INIZCTEOSA-N 0.000 claims 1
JZEJSKHODSENIT-INIZCTEOSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3s)-3-methylpiperazin-1-yl]-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@H](C)NCC2)=NC=1NC1=CC=CC(C)=N1 JZEJSKHODSENIT-INIZCTEOSA-N 0.000 claims 1
WYOKLIUTLXIBLC-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(1-ethylpiperidin-4-yl)-7-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(CC)CC1 WYOKLIUTLXIBLC-UHFFFAOYSA-N 0.000 claims 1
MUXVDKXXOUJOFI-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(1-ethylpiperidin-4-yl)-7-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=C(C)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(CC)CC1 MUXVDKXXOUJOFI-UHFFFAOYSA-N 0.000 claims 1
QBWVTNLSVSCFEL-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(1-ethylpiperidin-4-yl)-7-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(CC)CC1 QBWVTNLSVSCFEL-UHFFFAOYSA-N 0.000 claims 1
MZMOWAKPUKLJGP-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(1-methylpiperidin-4-yl)-7-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(C)CC1 MZMOWAKPUKLJGP-UHFFFAOYSA-N 0.000 claims 1
KEJIFILQJYVKPL-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(1-propan-2-ylpiperidin-4-yl)-7-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(C(C)C)CC1 KEJIFILQJYVKPL-UHFFFAOYSA-N 0.000 claims 1
XOPCGQWCEOLCSB-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-(piperidin-4-ylmethyl)-7-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 XOPCGQWCEOLCSB-UHFFFAOYSA-N 0.000 claims 1
HRRIBNWFHPLPLR-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CCN(C)CC2)=NC=1NC1=CC(C)=CC=N1 HRRIBNWFHPLPLR-UHFFFAOYSA-N 0.000 claims 1
OUBRVKYMSDPJMW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-(5-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CCN(C)CC2)=NC=1NC1=CC=C(C)C=N1 OUBRVKYMSDPJMW-UHFFFAOYSA-N 0.000 claims 1
BWHNNEMQHHTTJC-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CCN(C)CC2)=NC=1NC1=CC=CC=N1 BWHNNEMQHHTTJC-UHFFFAOYSA-N 0.000 claims 1
FHUOEUSJZABXPZ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-7-n-(3-methylphenyl)-5-n-(1-methylpyrrolidin-3-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CN(C)CC2)=NC=1NC1=CC=CC(C)=C1 FHUOEUSJZABXPZ-UHFFFAOYSA-N 0.000 claims 1
PFYZHGVAVYUBFG-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-7-n-(4-methylpyridin-2-yl)-5-n-(1-methylpyrrolidin-3-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CN(C)CC2)=NC=1NC1=CC(C)=CC=N1 PFYZHGVAVYUBFG-UHFFFAOYSA-N 0.000 claims 1
TZBPVZOVQXJOAK-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-n-piperidin-4-yl-7-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCNCC1 TZBPVZOVQXJOAK-UHFFFAOYSA-N 0.000 claims 1
GRYMXFLCUPGRFW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-piperazin-1-yl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC=N1 GRYMXFLCUPGRFW-UHFFFAOYSA-N 0.000 claims 1
LDLNMLJYTORHKF-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(3-fluorophenyl)-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2C=C(F)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 LDLNMLJYTORHKF-UHFFFAOYSA-N 0.000 claims 1
WPFVQRDMPLDYQI-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(3-methoxyphenyl)-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2C=C(OC)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 WPFVQRDMPLDYQI-UHFFFAOYSA-N 0.000 claims 1
GKUBWDIKHOSFGJ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(4-fluorophenyl)-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2C=CC(F)=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 GKUBWDIKHOSFGJ-UHFFFAOYSA-N 0.000 claims 1
FSXHZTOSBFMJNT-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(4-methylpyridin-2-yl)-5-n-(1-propan-2-ylpiperidin-4-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(C(C)C)CC1 FSXHZTOSBFMJNT-UHFFFAOYSA-N 0.000 claims 1
FYRCMBJWMHKGSP-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(4-methylpyridin-2-yl)-5-n-(2-morpholin-4-ylethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCCN1CCOCC1 FYRCMBJWMHKGSP-UHFFFAOYSA-N 0.000 claims 1
XDLYAHVCLXQTFX-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(4-methylpyridin-2-yl)-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 XDLYAHVCLXQTFX-UHFFFAOYSA-N 0.000 claims 1
SBVLBLDYDBXPBQ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(4-methylpyridin-2-yl)-5-n-piperidin-4-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCNCC1 SBVLBLDYDBXPBQ-UHFFFAOYSA-N 0.000 claims 1
PLOCGLSEEJOBFO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-ethylpyridin-2-yl)-5-n-methyl-5-n-(1-methylpiperidin-4-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CCN(C)CC2)=NC=1NC1=CC=CC(CC)=N1 PLOCGLSEEJOBFO-UHFFFAOYSA-N 0.000 claims 1
AMSPIGUJBZIQHY-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-ethylpyridin-2-yl)-5-n-methyl-5-n-(1-methylpyrrolidin-3-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CN(C)CC2)=NC=1NC1=CC=CC(CC)=N1 AMSPIGUJBZIQHY-UHFFFAOYSA-N 0.000 claims 1
QCUCDXSSDJFTNO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-methylpyridin-2-yl)-5-n-(1-propan-2-ylpiperidin-4-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=C(C)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(C(C)C)CC1 QCUCDXSSDJFTNO-UHFFFAOYSA-N 0.000 claims 1
INXAFIHEAUEMHU-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-methylpyridin-2-yl)-5-n-(2-morpholin-4-ylethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=C(C)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCCN1CCOCC1 INXAFIHEAUEMHU-UHFFFAOYSA-N 0.000 claims 1
JLQIQBLFJBEJTD-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-methylpyridin-2-yl)-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=C(C)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 JLQIQBLFJBEJTD-UHFFFAOYSA-N 0.000 claims 1
FOEPKDSBOPDZEN-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-(6-methylpyridin-2-yl)-5-n-piperidin-4-ylpyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2N=C(C)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCNCC1 FOEPKDSBOPDZEN-UHFFFAOYSA-N 0.000 claims 1
QQVDTGNVTWLTCF-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-7-n-phenyl-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2C=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 QQVDTGNVTWLTCF-UHFFFAOYSA-N 0.000 claims 1
GWBZSJGDLCIQOO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-fluorophenyl)-5-(4-methylpiperazin-1-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC(F)=C1 GWBZSJGDLCIQOO-UHFFFAOYSA-N 0.000 claims 1
WZAYJMNVBWGTEC-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-fluorophenyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(F)=C1 WZAYJMNVBWGTEC-OAHLLOKOSA-N 0.000 claims 1
RPEPTARZZYIHPE-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-fluorophenyl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC(F)=C1 RPEPTARZZYIHPE-UHFFFAOYSA-N 0.000 claims 1
DIPTYEMVBCCERV-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-methoxyphenyl)-5-(4-methylpiperazin-1-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC(OC)=C1 DIPTYEMVBCCERV-UHFFFAOYSA-N 0.000 claims 1
LXEIVZNLQWRYPZ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-methoxyphenyl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC(OC)=C1 LXEIVZNLQWRYPZ-UHFFFAOYSA-N 0.000 claims 1
SEYNTVSJFXWNHU-QGZVFWFLSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-methylphenyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(C)=C1 SEYNTVSJFXWNHU-QGZVFWFLSA-N 0.000 claims 1
FTFLQFFFCFEWQC-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(3-methylpyridin-2-yl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=NC=CC=C1C FTFLQFFFCFEWQC-UHFFFAOYSA-N 0.000 claims 1
IOJTWWISEIGGBD-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(4-fluorophenyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=C(F)C=C1 IOJTWWISEIGGBD-OAHLLOKOSA-N 0.000 claims 1
AFNXLLBJVMVVLQ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC(C)=CC=N1 AFNXLLBJVMVVLQ-UHFFFAOYSA-N 0.000 claims 1
RVESLZBWSIINGV-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(5-methylpyridin-2-yl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=C(C)C=N1 RVESLZBWSIINGV-UHFFFAOYSA-N 0.000 claims 1
RHUURABEIWKMSG-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-(6-methylpyridin-2-yl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC(C)=N1 RHUURABEIWKMSG-UHFFFAOYSA-N 0.000 claims 1
XIEAYYVLHOZOEO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-n-phenyl-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC=C1 XIEAYYVLHOZOEO-UHFFFAOYSA-N 0.000 claims 1
BQACRCDDFBIQAX-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-5-(4-methylpiperazin-1-yl)-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC(C)=CC=N1 BQACRCDDFBIQAX-UHFFFAOYSA-N 0.000 claims 1
VMCOCLYBDRDLSE-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-5-(4-methylpiperazin-1-yl)-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC(C)=N1 VMCOCLYBDRDLSE-UHFFFAOYSA-N 0.000 claims 1
YVHDEWQLIMAKJD-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-5-(4-methylpiperazin-1-yl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC=N1 YVHDEWQLIMAKJD-UHFFFAOYSA-N 0.000 claims 1
KGUYYHZGVBWCDQ-OAHLLOKOSA-N 1-(2-ethoxyethyl)-3-methyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC(C)=CC=N1 KGUYYHZGVBWCDQ-OAHLLOKOSA-N 0.000 claims 1
QMCFQTQVCHAMDL-CQSZACIVSA-N 1-(2-ethoxyethyl)-3-methyl-5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=N1 QMCFQTQVCHAMDL-CQSZACIVSA-N 0.000 claims 1
ZHZMWQQYGLFACT-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-5-piperazin-1-yl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC=N1 ZHZMWQQYGLFACT-UHFFFAOYSA-N 0.000 claims 1
XCUNWJSUUNZLPM-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-n-(6-methylpyridin-2-yl)-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCNCC2)=NC=1NC1=CC=CC(C)=N1 XCUNWJSUUNZLPM-UHFFFAOYSA-N 0.000 claims 1
SFTMAEWYVZRVMG-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-(4-ethylpiperazin-1-yl)-3-(methoxymethyl)-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2CCN(CC)CC2)=NC=1NC1=CC=NC=N1 SFTMAEWYVZRVMG-UHFFFAOYSA-N 0.000 claims 1
OCYIZENYTQXCPM-OAHLLOKOSA-N 1-(2-ethoxyethyl)-n-(4-fluorophenyl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=C(F)C=C1 OCYIZENYTQXCPM-OAHLLOKOSA-N 0.000 claims 1
DNCWLPCUHNCWHU-MRXNPFEDSA-N 1-(2-ethoxyethyl)-n-(6-ethylpyridin-2-yl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(CC)=N1 DNCWLPCUHNCWHU-MRXNPFEDSA-N 0.000 claims 1
VGLBIYCAGGWOPA-UHFFFAOYSA-N 1-[1-(2-ethoxyethyl)-3-ethyl-7-(4-fluoroanilino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxamide Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CC(CCC2)C(N)=O)=NC=1NC1=CC=C(F)C=C1 VGLBIYCAGGWOPA-UHFFFAOYSA-N 0.000 claims 1
GXZQZXDEHAFIGK-UHFFFAOYSA-N 1-[1-(2-ethoxyethyl)-3-ethyl-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxamide Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CC(CCC2)C(N)=O)=NC=1NC1=CC(C)=CC=N1 GXZQZXDEHAFIGK-UHFFFAOYSA-N 0.000 claims 1
WCRZNYFZUQOBDV-UHFFFAOYSA-N 1-[1-(2-ethoxyethyl)-3-ethyl-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-4-carboxamide Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CC2)C(N)=O)=NC=1NC1=CC(C)=CC=N1 WCRZNYFZUQOBDV-UHFFFAOYSA-N 0.000 claims 1
YYCDTEXHHPXFSD-UHFFFAOYSA-N 1-[1-(2-ethoxyethyl)-3-ethyl-7-[(6-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-4-carboxamide Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CC2)C(N)=O)=NC=1NC1=CC=CC(C)=N1 YYCDTEXHHPXFSD-UHFFFAOYSA-N 0.000 claims 1
CBTKVKJWTOABRM-UHFFFAOYSA-N 1-[3-(ethoxymethyl)-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-ol 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C(C)OCC1=NN(C2=C1N=C(N=C2NC2=NC=NC=C2)N2CCC(CC2)O)CCOCC(F)(F)F CBTKVKJWTOABRM-UHFFFAOYSA-N 0.000 claims 1
HOKQFCPKIIDGFM-UHFFFAOYSA-N 1-[3-ethyl-7-[(4-methylpyridin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxamide Chemical compound N1=C(N2CC(CCC2)C(N)=O)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC(C)=CC=N1 HOKQFCPKIIDGFM-UHFFFAOYSA-N 0.000 claims 1
REZOYUVWUDBAOR-UHFFFAOYSA-N 2-[4-[3-ethyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperazin-1-yl]ethanol Chemical compound N1=C(N2CCN(CCO)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 REZOYUVWUDBAOR-UHFFFAOYSA-N 0.000 claims 1
RAOKRLJQSPBJHF-UHFFFAOYSA-N 3-(cyclopropylmethoxymethyl)-5-piperazin-1-yl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C12=NC(N3CCNCC3)=NC(NC=3N=CN=CC=3)=C2N(CCOCC(F)(F)F)N=C1COCC1CC1 RAOKRLJQSPBJHF-UHFFFAOYSA-N 0.000 claims 1
YPJRURLHMDFAQL-UHFFFAOYSA-N 3-(ethoxymethyl)-5-(4-methylpiperazin-1-yl)-N-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOCc1nn(CCOCC(F)(F)F)c2c(Nc3ccncn3)nc(nc12)N1CCN(C)CC1 YPJRURLHMDFAQL-UHFFFAOYSA-N 0.000 claims 1
ZOYXHCXQYKRMDZ-GOSISDBHSA-N 3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-(6-methylpyridin-2-yl)-1-(2-propoxyethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(C)=N1 ZOYXHCXQYKRMDZ-GOSISDBHSA-N 0.000 claims 1
KRUQTMNEBMWLIU-PFEQFJNWSA-N 3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(N2C[C@@H](C)NCC2)N=C2C(COCC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 KRUQTMNEBMWLIU-PFEQFJNWSA-N 0.000 claims 1
KRUQTMNEBMWLIU-UQKRIMTDSA-N 3-(ethoxymethyl)-5-[(3s)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(N2C[C@H](C)NCC2)N=C2C(COCC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 KRUQTMNEBMWLIU-UQKRIMTDSA-N 0.000 claims 1
RTHLTPDYVGEYBH-UHFFFAOYSA-N 3-(ethoxymethyl)-5-piperazin-1-yl-N-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOCc1nn(CCOCC(F)(F)F)c2c(Nc3ccncn3)nc(nc12)N1CCNCC1 RTHLTPDYVGEYBH-UHFFFAOYSA-N 0.000 claims 1
YOIADBZBIOMCDL-MRXNPFEDSA-N 3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-1-(2-propoxyethyl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=N1 YOIADBZBIOMCDL-MRXNPFEDSA-N 0.000 claims 1
AVVFUMYYGGYMMF-QGZVFWFLSA-N 3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]-n-(6-methylpyridin-2-yl)-1-(2-propoxyethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(C)=N1 AVVFUMYYGGYMMF-QGZVFWFLSA-N 0.000 claims 1
TUWXCZSSUQGSIV-UHFFFAOYSA-N 3-ethyl-5-(4-ethylpiperazin-1-yl)-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(CC)CCN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2CC)C2=N1 TUWXCZSSUQGSIV-UHFFFAOYSA-N 0.000 claims 1
LPIMXICOGCYACY-UHFFFAOYSA-N 3-ethyl-5-(4-ethylsulfonylpiperazin-1-yl)-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCN(CC2)S(=O)(=O)CC)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 LPIMXICOGCYACY-UHFFFAOYSA-N 0.000 claims 1
HMXWWEZJHIDDEP-UHFFFAOYSA-N 3-ethyl-5-(4-methyl-1,4-diazepan-1-yl)-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCN(C)CCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 HMXWWEZJHIDDEP-UHFFFAOYSA-N 0.000 claims 1
IJUIVMPEWZKWIH-CQSZACIVSA-N 3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(4-methylpyrimidin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=NC=CC(C)=N1 IJUIVMPEWZKWIH-CQSZACIVSA-N 0.000 claims 1
WHGIWJDENAGZPX-OAHLLOKOSA-N 3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-(6-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC(C)=N1 WHGIWJDENAGZPX-OAHLLOKOSA-N 0.000 claims 1
MPXCHGIQKTWWQT-CYBMUJFWSA-N 3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-pyrazin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CN=CC=N1 MPXCHGIQKTWWQT-CYBMUJFWSA-N 0.000 claims 1
XBIPOXQOAFPLKE-CQSZACIVSA-N 3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 XBIPOXQOAFPLKE-CQSZACIVSA-N 0.000 claims 1
UCRSYBKADUKGLT-CYBMUJFWSA-N 3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 UCRSYBKADUKGLT-CYBMUJFWSA-N 0.000 claims 1
UCRSYBKADUKGLT-ZDUSSCGKSA-N 3-ethyl-5-[(3s)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 UCRSYBKADUKGLT-ZDUSSCGKSA-N 0.000 claims 1
MSLJYTVWMHIMIV-UHFFFAOYSA-N 3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-(4-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C2CCN(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC(C)=CC=N1 MSLJYTVWMHIMIV-UHFFFAOYSA-N 0.000 claims 1
DKJUADHNWXNJQF-UHFFFAOYSA-N 3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-pyrazin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C2CCN(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CN=CC=N1 DKJUADHNWXNJQF-UHFFFAOYSA-N 0.000 claims 1
RFUQTPAAFXXWIY-UHFFFAOYSA-N 3-ethyl-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-7-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C2CCN(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 RFUQTPAAFXXWIY-UHFFFAOYSA-N 0.000 claims 1
PAIBQHDKQCITSF-UHFFFAOYSA-N 3-ethyl-5-n-methyl-7-n-(4-methylphenyl)-5-n-(1-methylpiperidin-4-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C2CCN(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=C1 PAIBQHDKQCITSF-UHFFFAOYSA-N 0.000 claims 1
OTVPORBTBHZBBY-UHFFFAOYSA-N 3-ethyl-5-piperazin-1-yl-n-pyrazin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CN=CC=N1 OTVPORBTBHZBBY-UHFFFAOYSA-N 0.000 claims 1
LTSKFIUQHVFYPX-UHFFFAOYSA-N 3-ethyl-7-n-(4-fluorophenyl)-5-n-methyl-5-n-(1-methylpiperidin-4-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(N(C)C2CCN(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(F)C=C1 LTSKFIUQHVFYPX-UHFFFAOYSA-N 0.000 claims 1
YGCVBPWMIHLBJH-CQSZACIVSA-N 3-ethyl-n-(4-fluorophenyl)-5-[(3r)-3-methylpiperazin-1-yl]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(F)C=C1 YGCVBPWMIHLBJH-CQSZACIVSA-N 0.000 claims 1
YBBACVAVZQMBOM-UHFFFAOYSA-N 3-ethyl-n-(4-fluorophenyl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(F)C=C1 YBBACVAVZQMBOM-UHFFFAOYSA-N 0.000 claims 1
GDERROXSQPLAQY-MRXNPFEDSA-N 3-ethyl-n-(4-methylphenyl)-5-[(3r)-3-methylpiperazin-1-yl]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=C1 GDERROXSQPLAQY-MRXNPFEDSA-N 0.000 claims 1
QEPWMKCPTLKANP-UHFFFAOYSA-N 3-ethyl-n-(4-methylphenyl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=C1 QEPWMKCPTLKANP-UHFFFAOYSA-N 0.000 claims 1
FGSINUUPXUCXID-UHFFFAOYSA-N 3-ethyl-n-(4-methylpyridin-2-yl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC(C)=CC=N1 FGSINUUPXUCXID-UHFFFAOYSA-N 0.000 claims 1
JXMQNAMZSSIGDD-UHFFFAOYSA-N 3-ethyl-n-(4-methylpyrimidin-2-yl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=NC=CC(C)=N1 JXMQNAMZSSIGDD-UHFFFAOYSA-N 0.000 claims 1
OVLZJPISKIFEAA-UHFFFAOYSA-N 3-ethyl-n-(6-methylpyridin-2-yl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC(C)=N1 OVLZJPISKIFEAA-UHFFFAOYSA-N 0.000 claims 1
KEVLUTBMYJZCCE-KRWDZBQOSA-N 3-ethyl-n-pyrimidin-4-yl-5-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2[C@@H](CCC2)CN2CCCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 KEVLUTBMYJZCCE-KRWDZBQOSA-N 0.000 claims 1
PACSWDNFOVMFNZ-UHFFFAOYSA-N 3-methyl-5-(4-methylpiperazin-1-yl)-n-(4-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCN1C1=NC(NC=2N=CC=C(C)C=2)=C(N(CCOCC(F)(F)F)N=C2C)C2=N1 PACSWDNFOVMFNZ-UHFFFAOYSA-N 0.000 claims 1
TXUISVPZWBYVAL-UHFFFAOYSA-N 3-methyl-5-(4-methylpiperazin-1-yl)-n-(6-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCN1C1=NC(NC=2N=C(C)C=CC=2)=C(N(CCOCC(F)(F)F)N=C2C)C2=N1 TXUISVPZWBYVAL-UHFFFAOYSA-N 0.000 claims 1
PXIFCRCOYQBRAK-UHFFFAOYSA-N 3-methyl-5-(4-methylpiperazin-1-yl)-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCN1C1=NC(NC=2N=CC=CC=2)=C(N(CCOCC(F)(F)F)N=C2C)C2=N1 PXIFCRCOYQBRAK-UHFFFAOYSA-N 0.000 claims 1
KOBHUQKQHNXZSP-CYBMUJFWSA-N 3-methyl-5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN[C@H](C)CN1C1=NC(NC=2N=CC=CC=2)=C(N(CCOCC(F)(F)F)N=C2C)C2=N1 KOBHUQKQHNXZSP-CYBMUJFWSA-N 0.000 claims 1
OLSXWCSSRFQJRB-UHFFFAOYSA-N 3-methyl-5-piperazin-1-yl-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 OLSXWCSSRFQJRB-UHFFFAOYSA-N 0.000 claims 1
JPPXWCPFACXJOK-UHFFFAOYSA-N 3-methyl-n-(4-methylpyridin-2-yl)-5-piperazin-1-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC(C)=CC=N1 JPPXWCPFACXJOK-UHFFFAOYSA-N 0.000 claims 1
GLMQUPDEVTYSIW-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(4-fluorophenyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCCC2)=NC=1NC1=CC=C(F)C=C1 GLMQUPDEVTYSIW-UHFFFAOYSA-N 0.000 claims 1
QRQOUVMRMMPLKS-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCCC2)=NC=1NC1=CC(C)=CC=N1 QRQOUVMRMMPLKS-UHFFFAOYSA-N 0.000 claims 1
KBQCZXKHJACKAD-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-3-ethyl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 KBQCZXKHJACKAD-UHFFFAOYSA-N 0.000 claims 1
JWQSKUQODCDYQU-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-3-methyl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCCC2)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 JWQSKUQODCDYQU-UHFFFAOYSA-N 0.000 claims 1
DLVTXTOJYQCXOY-UHFFFAOYSA-N 5-(3,4-dimethylpiperazin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CC(C)N(C)CC2)=NC=1NC1=CC(C)=CC=N1 DLVTXTOJYQCXOY-UHFFFAOYSA-N 0.000 claims 1
PAKNUWOSQFRPIH-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(3-fluorophenyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=CC(F)=C1 PAKNUWOSQFRPIH-UHFFFAOYSA-N 0.000 claims 1
CIKJBAYSAWJFLF-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(3-methoxyphenyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=CC(OC)=C1 CIKJBAYSAWJFLF-UHFFFAOYSA-N 0.000 claims 1
UMDUIFDDMSVEOP-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(4-fluorophenyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=C(F)C=C1 UMDUIFDDMSVEOP-UHFFFAOYSA-N 0.000 claims 1
LASVKJLQJACNOV-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC(C)=CC=N1 LASVKJLQJACNOV-UHFFFAOYSA-N 0.000 claims 1
OWFMCOSQZOAGJK-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-phenylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=CC=C1 OWFMCOSQZOAGJK-UHFFFAOYSA-N 0.000 claims 1
IKBHJPDGHXDTTP-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=CC=N1 IKBHJPDGHXDTTP-UHFFFAOYSA-N 0.000 claims 1
XNHOANPNYNAQJH-UHFFFAOYSA-N 5-(4-aminopiperidin-1-yl)-1-(2-ethoxyethyl)-3-methyl-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCC(N)CC2)=NC=1NC1=CC=CC(C)=N1 XNHOANPNYNAQJH-UHFFFAOYSA-N 0.000 claims 1
BXNGPIIKDFLEGG-ROUUACIJSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(2-ethoxyethyl)-3-(ethoxymethyl)-n-(6-ethylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=CC(CC)=N1 BXNGPIIKDFLEGG-ROUUACIJSA-N 0.000 claims 1
XECDTYMNNAVCDO-GJZGRUSLSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(2-ethoxyethyl)-3-(ethoxymethyl)-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=NC=N1 XECDTYMNNAVCDO-GJZGRUSLSA-N 0.000 claims 1
ISOTXRXRUDXRAI-GJZGRUSLSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(2-ethoxyethyl)-3-(methoxymethyl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=CC=N1 ISOTXRXRUDXRAI-GJZGRUSLSA-N 0.000 claims 1
WLMADZDSQBDONK-IRXDYDNUSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(2-ethoxyethyl)-n-(6-ethylpyridin-2-yl)-3-(methoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=CC(CC)=N1 WLMADZDSQBDONK-IRXDYDNUSA-N 0.000 claims 1
GORWAUPRSANCLH-IRXDYDNUSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-(ethoxymethyl)-1-(2-propoxyethyl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COCC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=CC=N1 GORWAUPRSANCLH-IRXDYDNUSA-N 0.000 claims 1
BQHYPTWIVDNXNY-ROUUACIJSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-(ethoxymethyl)-n-(6-methylpyridin-2-yl)-1-(2-propoxyethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COCC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC=CC(C)=N1 BQHYPTWIVDNXNY-ROUUACIJSA-N 0.000 claims 1
SHVYXZBRAOEKLQ-ROUUACIJSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-n-(4,6-dimethylpyridin-2-yl)-1-(2-ethoxyethyl)-3-(ethoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2[C@H]3C[C@H](NC3)C2)=NC=1NC1=CC(C)=CC(C)=N1 SHVYXZBRAOEKLQ-ROUUACIJSA-N 0.000 claims 1
OIHMKXZADULKIA-CQSZACIVSA-N 5-[(3r)-3,4-dimethylpiperazin-1-yl]-3-ethyl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)N(C)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 OIHMKXZADULKIA-CQSZACIVSA-N 0.000 claims 1
IOZJYKBDTUBWSV-OAHLLOKOSA-N 5-[(3r)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-3-(4,4,4-trifluorobutoxymethyl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN[C@H](C)CN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2COCCCC(F)(F)F)C2=N1 IOZJYKBDTUBWSV-OAHLLOKOSA-N 0.000 claims 1
OSRZCRFHOPPVDR-CALCHBBNSA-N 5-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)N[C@@H](C)C2)=NC=1NC1=CC(C)=CC=N1 OSRZCRFHOPPVDR-CALCHBBNSA-N 0.000 claims 1
PDLOULNXIJXNIW-ZDUSSCGKSA-N 5-[(3s)-3-methylpiperazin-1-yl]-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]-3-(2,2,2-trifluoroethoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN[C@@H](C)CN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2COCC(F)(F)F)C2=N1 PDLOULNXIJXNIW-ZDUSSCGKSA-N 0.000 claims 1
AMBSOYSAQQXYJT-IYBDPMFKSA-N 5-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)N[C@@H](C)C2)=NC=1NC1=CC=CC=N1 AMBSOYSAQQXYJT-IYBDPMFKSA-N 0.000 claims 1
MROMCAKLKXCOAN-UHFFFAOYSA-N 5-[4-(2-aminoethyl)piperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(CCN)CC2)=NC=1NC1=CC(C)=CC=N1 MROMCAKLKXCOAN-UHFFFAOYSA-N 0.000 claims 1
DWBODCJIKNJWFW-UHFFFAOYSA-N 5-[4-(2-aminoethyl)piperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(CCN)CC2)=NC=1NC1=CC=CC(C)=N1 DWBODCJIKNJWFW-UHFFFAOYSA-N 0.000 claims 1
YDMKQZLRKOHBFO-UHFFFAOYSA-N 5-[4-(2-aminoethyl)piperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(CCN)CC2)=NC=1NC1=CC=CC=N1 YDMKQZLRKOHBFO-UHFFFAOYSA-N 0.000 claims 1
HYPYDFGYXJFEHS-UHFFFAOYSA-N 5-[4-(aminomethyl)piperidin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CN)CC2)=NC=1NC1=CC(C)=CC=N1 HYPYDFGYXJFEHS-UHFFFAOYSA-N 0.000 claims 1
KDHAYSNKXNPQAU-UHFFFAOYSA-N 5-[4-(aminomethyl)piperidin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CN)CC2)=NC=1NC1=CC=CC(C)=N1 KDHAYSNKXNPQAU-UHFFFAOYSA-N 0.000 claims 1
IXJRRKVUMKLONX-UHFFFAOYSA-N 5-[4-(aminomethyl)piperidin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CN)CC2)=NC=1NC1=CC=CC=N1 IXJRRKVUMKLONX-UHFFFAOYSA-N 0.000 claims 1
VGXRBHNQQLSXDW-UHFFFAOYSA-N 5-[[1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)pyrazolo[4,3-d]pyrimidin-7-yl]amino]-1h-pyridin-2-one Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC=1C=CC(=O)NC=1 VGXRBHNQQLSXDW-UHFFFAOYSA-N 0.000 claims 1
YULHTLCUWNXIFL-CQSZACIVSA-N 5-[[1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-yl]amino]-1h-pyridin-2-one Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC=1C=CC(=O)NC=1 YULHTLCUWNXIFL-CQSZACIVSA-N 0.000 claims 1
ZBUQBIFJWMOBFH-UHFFFAOYSA-N 5-[[1-(2-ethoxyethyl)-3-ethyl-5-piperazin-1-ylpyrazolo[4,3-d]pyrimidin-7-yl]amino]-1h-pyridin-2-one Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC=1C=CC(=O)NC=1 ZBUQBIFJWMOBFH-UHFFFAOYSA-N 0.000 claims 1
LCDYWUAAUATRIN-UHFFFAOYSA-N 5-n-(1-benzylpyrrolidin-3-yl)-1-(2-ethoxyethyl)-3-ethyl-5-n-methyl-7-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N(C)C2CN(CC=3C=CC=CC=3)CC2)=NC=1NC1=CC(C)=CC=N1 LCDYWUAAUATRIN-UHFFFAOYSA-N 0.000 claims 1
UEVIFNWBXVHDGP-UHFFFAOYSA-N 5-n-(2-aminoethyl)-3-ethyl-7-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N1=C(NCCN)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 UEVIFNWBXVHDGP-UHFFFAOYSA-N 0.000 claims 1
OIKJIBHVIBURIU-UHFFFAOYSA-N 5-piperazin-1-yl-3-(propan-2-yloxymethyl)-N-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C(C)(C)OCC1=NN(C2=C1N=C(N=C2NC2=NC=NC=C2)N2CCNCC2)CCOCC(F)(F)F OIKJIBHVIBURIU-UHFFFAOYSA-N 0.000 claims 1
SMHSLTJSVKJSLF-UHFFFAOYSA-N 5-piperazin-1-yl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]-3-(2,2,2-trifluoroethoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC(F)(F)F)N=C(COCC(F)(F)F)C2=NC(N2CCNCC2)=NC=1NC1=CC=NC=N1 SMHSLTJSVKJSLF-UHFFFAOYSA-N 0.000 claims 1
JFAUVMPNYQDZHH-UHFFFAOYSA-N 5-piperazin-1-yl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]-3-(3,3,3-trifluoropropoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCC2)N=C2C(COCCC(F)(F)F)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 JFAUVMPNYQDZHH-UHFFFAOYSA-N 0.000 claims 1
QDCFKUANWNRTDE-UHFFFAOYSA-N 7-n-(3-chlorophenyl)-1-(2-ethoxyethyl)-3-ethyl-5-n-(piperidin-4-ylmethyl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound N=1C(NC=2C=C(Cl)C=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NCC1CCNCC1 QDCFKUANWNRTDE-UHFFFAOYSA-N 0.000 claims 1
FBXPMOWWOYMNLF-UHFFFAOYSA-N C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=CC(=C2)C)N2CCC(CC2)CO)CCOCC(F)(F)F Chemical compound C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=CC(=C2)C)N2CCC(CC2)CO)CCOCC(F)(F)F FBXPMOWWOYMNLF-UHFFFAOYSA-N 0.000 claims 1
XQRLRIABELSLSI-OAHLLOKOSA-N C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=CC(=C2)C)N2C[C@H](NCC2)C)CCOCC(F)(F)F Chemical compound C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=CC(=C2)C)N2C[C@H](NCC2)C)CCOCC(F)(F)F XQRLRIABELSLSI-OAHLLOKOSA-N 0.000 claims 1
BDBOKHIGDSMNEJ-MRXNPFEDSA-N C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=CC(=CC=C2)OC)N2C[C@H](NCC2)C)CC Chemical compound C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=CC(=CC=C2)OC)N2C[C@H](NCC2)C)CC BDBOKHIGDSMNEJ-MRXNPFEDSA-N 0.000 claims 1
BMHVWXVLEHHSBG-MRXNPFEDSA-N C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC(=CC=C2)CC)N2C[C@H](NCC2)C)CC Chemical compound C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC(=CC=C2)CC)N2C[C@H](NCC2)C)CC BMHVWXVLEHHSBG-MRXNPFEDSA-N 0.000 claims 1
MEMIXHNQNSWWOX-MRXNPFEDSA-N C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=C(C=C2)C)N2C[C@H](NCC2)C)CC Chemical compound C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=C(C=C2)C)N2C[C@H](NCC2)C)CC MEMIXHNQNSWWOX-MRXNPFEDSA-N 0.000 claims 1
KCWGJEVLXMWZRX-UHFFFAOYSA-N C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=CC=C2)N2CCN(CC2)C)CC Chemical compound C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=CC=C2)N2CCN(CC2)C)CC KCWGJEVLXMWZRX-UHFFFAOYSA-N 0.000 claims 1
CDOWLGGQYRKAGM-OAHLLOKOSA-N C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=CC=C2)N2C[C@H](NCC2)C)CC Chemical compound C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=CC=C2)N2C[C@H](NCC2)C)CC CDOWLGGQYRKAGM-OAHLLOKOSA-N 0.000 claims 1
PJLODXUVJVTZCA-QGZVFWFLSA-N CC1=CC(=NC(=C1)C)NC=1C2=C(N=C(N1)N1C[C@H](NCC1)C)C(=NN2CCOCC)CC Chemical compound CC1=CC(=NC(=C1)C)NC=1C2=C(N=C(N1)N1C[C@H](NCC1)C)C(=NN2CCOCC)CC PJLODXUVJVTZCA-QGZVFWFLSA-N 0.000 claims 1
PDLOULNXIJXNIW-CYBMUJFWSA-N C[C@@H]1CN(CCN1)C=1N=C(C2=C(N1)C(=NN2CCOCC(F)(F)F)COCC(F)(F)F)NC2=NC=NC=C2 Chemical compound C[C@@H]1CN(CCN1)C=1N=C(C2=C(N1)C(=NN2CCOCC(F)(F)F)COCC(F)(F)F)NC2=NC=NC=C2 PDLOULNXIJXNIW-CYBMUJFWSA-N 0.000 claims 1
YXCNJGBXUJPJCQ-UHFFFAOYSA-N ClC=1C=C(C=CC1)NC=1C2=C(N=C(N1)N1CCNCC1)C(=NN2CCOCC)CC Chemical compound ClC=1C=C(C=CC1)NC=1C2=C(N=C(N1)N1CCNCC1)C(=NN2CCOCC)CC YXCNJGBXUJPJCQ-UHFFFAOYSA-N 0.000 claims 1
XQBROSGEMIHETQ-IODNYQNNSA-N FC(C(=O)O)(F)F.[C@@H]12N(C[C@@H](NC1)C2)C=2N=C(C1=C(N2)C(=NN1CCOCC(F)(F)F)COCC)NC1=NC=NC=C1 Chemical compound FC(C(=O)O)(F)F.[C@@H]12N(C[C@@H](NC1)C2)C=2N=C(C1=C(N2)C(=NN1CCOCC(F)(F)F)COCC)NC1=NC=NC=C1 XQBROSGEMIHETQ-IODNYQNNSA-N 0.000 claims 1
241000124008 Mammalia Species 0.000 claims 1
XUOBOPQEYFPWNK-UHFFFAOYSA-N NC1CCN(CC1)C=1N=C(C2=C(N1)C(=NN2CCOCC)CC)NC2=CC(=CC=C2)Cl Chemical compound NC1CCN(CC1)C=1N=C(C2=C(N1)C(=NN2CCOCC)CC)NC2=CC(=CC=C2)Cl XUOBOPQEYFPWNK-UHFFFAOYSA-N 0.000 claims 1
JDLWXBTZHYLVNL-UHFFFAOYSA-N [1-[1-(2-ethoxyethyl)-3-ethyl-7-(4-fluoroanilino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-yl]methanol Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CO)CC2)=NC=1NC1=CC=C(F)C=C1 JDLWXBTZHYLVNL-UHFFFAOYSA-N 0.000 claims 1
YRVSFLWYKOXNHW-UHFFFAOYSA-N [1-[1-(2-ethoxyethyl)-3-ethyl-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-yl]methanol Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCC(CO)CC2)=NC=1NC1=CC(C)=CC=N1 YRVSFLWYKOXNHW-UHFFFAOYSA-N 0.000 claims 1
OGDNRCJDKHWITM-UHFFFAOYSA-N [1-[3-(ethoxymethyl)-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-yl]methanol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(N2CCC(CO)CC2)N=C2C(COCC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 OGDNRCJDKHWITM-UHFFFAOYSA-N 0.000 claims 1
HIUQBQRVQMIPFS-UHFFFAOYSA-N [1-[3-ethyl-7-(pyrazin-2-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-yl]methanol Chemical compound N1=C(N2CCC(CO)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CN=CC=N1 HIUQBQRVQMIPFS-UHFFFAOYSA-N 0.000 claims 1
ZGZQIJSFWHZTPW-UHFFFAOYSA-N [1-[3-ethyl-7-(pyridin-2-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-yl]methanol Chemical compound N1=C(N2CCC(CO)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 ZGZQIJSFWHZTPW-UHFFFAOYSA-N 0.000 claims 1
AXPKYIJKKSCJMW-UHFFFAOYSA-N [1-[3-ethyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-3-yl]methanol Chemical compound N1=C(N2CC(CO)CCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 AXPKYIJKKSCJMW-UHFFFAOYSA-N 0.000 claims 1
DOYHEYNIRPCUIX-UHFFFAOYSA-N [1-[3-ethyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-yl]methanol Chemical compound N1=C(N2CCC(CO)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 DOYHEYNIRPCUIX-UHFFFAOYSA-N 0.000 claims 1
GRQLTRQLHRKPNG-UHFFFAOYSA-N [1-[3-ethyl-7-[(4-methylpyrimidin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-yl]methanol Chemical compound N1=C(N2CCC(CO)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=NC=CC(C)=N1 GRQLTRQLHRKPNG-UHFFFAOYSA-N 0.000 claims 1
GPJANRZNMQZGMK-UHFFFAOYSA-N [1-[3-ethyl-7-[(6-methylpyridin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-yl]methanol Chemical compound N1=C(N2CCC(CO)CC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC(C)=N1 GPJANRZNMQZGMK-UHFFFAOYSA-N 0.000 claims 1
WZBOISBGYRMZSU-UHFFFAOYSA-N [1-[3-methyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-3-yl]methanol Chemical compound N1=C(N2CC(CO)CCC2)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 WZBOISBGYRMZSU-UHFFFAOYSA-N 0.000 claims 1
ACZRRRMIFJPMAO-UHFFFAOYSA-N [1-[3-methyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidin-4-yl]methanol Chemical compound N1=C(N2CCC(CO)CC2)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 ACZRRRMIFJPMAO-UHFFFAOYSA-N 0.000 claims 1
CNTHATZVLALNJP-ROUUACIJSA-N [C@@H]12N(C[C@@H](NC1)C2)C=2N=C(C1=C(N2)C(=NN1CCOCC)COCC)NC1=CC=C(C=C1)F Chemical compound [C@@H]12N(C[C@@H](NC1)C2)C=2N=C(C1=C(N2)C(=NN1CCOCC)COCC)NC1=CC=C(C=C1)F CNTHATZVLALNJP-ROUUACIJSA-N 0.000 claims 1
YBKZXHRVXSZUJO-HOTGVXAUSA-N [C@@H]12N(C[C@@H](NC1)C2)C=2N=C(C1=C(N2)C(=NN1CCOCC)COCC)NC1=NC=CC=C1 Chemical compound [C@@H]12N(C[C@@H](NC1)C2)C=2N=C(C1=C(N2)C(=NN1CCOCC)COCC)NC1=NC=CC=C1 YBKZXHRVXSZUJO-HOTGVXAUSA-N 0.000 claims 1
PSYTYIGKMHRVMR-UHFFFAOYSA-N ethyl 4-[[1-(2-ethoxyethyl)-3-ethyl-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]amino]piperidine-1-carboxylate Chemical compound N=1C(NC=2N=CC=C(C)C=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC1CCN(C(=O)OCC)CC1 PSYTYIGKMHRVMR-UHFFFAOYSA-N 0.000 claims 1
OLFLQENATNKUGW-UHFFFAOYSA-N n,n-diethyl-1-[3-ethyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N(CC)CC)CCCN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2CC)C2=N1 OLFLQENATNKUGW-UHFFFAOYSA-N 0.000 claims 1
MOPLQNBPKHESRE-UHFFFAOYSA-N n-(3-chlorophenyl)-1-(2-ethoxyethyl)-3-ethyl-5-(4-methylpiperazin-1-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCN(C)CC2)=NC=1NC1=CC=CC(Cl)=C1 MOPLQNBPKHESRE-UHFFFAOYSA-N 0.000 claims 1
WNNKNOUFHQVNDZ-OAHLLOKOSA-N n-(3-chlorophenyl)-1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC(Cl)=C1 WNNKNOUFHQVNDZ-OAHLLOKOSA-N 0.000 claims 1
HFSJUYPZQGLUOO-GOSISDBHSA-N n-(4,6-dimethylpyridin-2-yl)-1-(2-ethoxyethyl)-3-(ethoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC(C)=CC(C)=N1 HFSJUYPZQGLUOO-GOSISDBHSA-N 0.000 claims 1
FUFMKKZPYTVCSX-QGZVFWFLSA-N n-(4,6-dimethylpyridin-2-yl)-1-(2-ethoxyethyl)-3-(methoxymethyl)-5-[(3r)-3-methylpiperazin-1-yl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC(C)=CC(C)=N1 FUFMKKZPYTVCSX-QGZVFWFLSA-N 0.000 claims 1
MIERCSAVVVRQCL-UHFFFAOYSA-N tert-butyl 4-[3-(propan-2-yloxymethyl)-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C(C)(C)OCC1=NN(C2=C1N=C(N=C2NC2=NC=NC=C2)N2CCN(CC2)C(=O)OC(C)(C)C)CCOCC(F)(F)F MIERCSAVVVRQCL-UHFFFAOYSA-N 0.000 claims 1
238000000034 method Methods 0.000 abstract description 190
239000000203 mixture Substances 0.000 abstract description 123
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
206010020772 Hypertension Diseases 0.000 abstract description 12
239000000543 intermediate Substances 0.000 abstract description 7
230000008569 process Effects 0.000 abstract description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 317
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 174
239000000243 solution Substances 0.000 description 135
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 126
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 116
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 95
235000019441 ethanol Nutrition 0.000 description 94
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 75
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
238000006243 chemical reaction Methods 0.000 description 75
239000002904 solvent Substances 0.000 description 72
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
239000011541 reaction mixture Substances 0.000 description 64
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
229910052757 nitrogen Inorganic materials 0.000 description 63
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 63
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 62
238000005160 1H NMR spectroscopy Methods 0.000 description 61
MPDXYVOXVJOKIN-UHFFFAOYSA-N 1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound NC1=NC=NC2=C1NN=C2 MPDXYVOXVJOKIN-UHFFFAOYSA-N 0.000 description 54
125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 51
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
239000007787 solid Substances 0.000 description 47
JOMNTHCQHJPVAZ-RXMQYKEDSA-N (2r)-2-methylpiperazine Chemical compound C[C@@H]1CNCCN1 JOMNTHCQHJPVAZ-RXMQYKEDSA-N 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 44
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 44
229910052760 oxygen Inorganic materials 0.000 description 44
239000001301 oxygen Chemical group 0.000 description 44
239000005864 Sulphur Chemical group 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
125000005842 heteroatom Chemical group 0.000 description 40
239000000047 product Substances 0.000 description 39
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 38
125000006413 ring segment Chemical group 0.000 description 38
239000000741 silica gel Substances 0.000 description 37
229910002027 silica gel Inorganic materials 0.000 description 37
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 35
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 34
229910052739 hydrogen Inorganic materials 0.000 description 33
235000019439 ethyl acetate Nutrition 0.000 description 32
239000007858 starting material Substances 0.000 description 32
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
238000004440 column chromatography Methods 0.000 description 30
239000001257 hydrogen Substances 0.000 description 30
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 29
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
238000009472 formulation Methods 0.000 description 27
125000001072 heteroaryl group Chemical group 0.000 description 27
238000004293 19F NMR spectroscopy Methods 0.000 description 25
229910052943 magnesium sulfate Inorganic materials 0.000 description 25
235000019341 magnesium sulphate Nutrition 0.000 description 25
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 25
125000000753 cycloalkyl group Chemical group 0.000 description 24
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 23
239000012043 crude product Substances 0.000 description 23
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 23
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 23
150000001412 amines Chemical class 0.000 description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 description 22
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
208000002193 Pain Diseases 0.000 description 21
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 21
239000002585 base Substances 0.000 description 21
125000002950 monocyclic group Chemical group 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 20
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
125000000217 alkyl group Chemical group 0.000 description 20
238000010992 reflux Methods 0.000 description 20
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 19
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 19
230000036407 pain Effects 0.000 description 19
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 19
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 18
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
101150041968 CDC13 gene Proteins 0.000 description 17
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 16
150000001299 aldehydes Chemical class 0.000 description 16
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 16
239000010410 layer Substances 0.000 description 16
238000003786 synthesis reaction Methods 0.000 description 16
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
125000004122 cyclic group Chemical group 0.000 description 15
125000005843 halogen group Chemical group 0.000 description 15
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 14
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 14
238000001914 filtration Methods 0.000 description 14
125000004433 nitrogen atom Chemical group N* 0.000 description 14
229960001760 dimethyl sulfoxide Drugs 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
238000003756 stirring Methods 0.000 description 13
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
150000001298 alcohols Chemical class 0.000 description 12
235000011114 ammonium hydroxide Nutrition 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 11
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 11
BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 description 11
125000004043 oxo group Chemical group O=* 0.000 description 11
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 10
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
239000012071 phase Substances 0.000 description 10
IQHXABCGSFAKPN-UHFFFAOYSA-N pyrrolidine-3-carboxamide Chemical compound NC(=O)C1CCNC1 IQHXABCGSFAKPN-UHFFFAOYSA-N 0.000 description 10
230000002829 reductive effect Effects 0.000 description 10
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
229920002554 vinyl polymer Polymers 0.000 description 10
UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 description 9
ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical group CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 9
229910021529 ammonia Inorganic materials 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 9
150000004985 diamines Chemical class 0.000 description 9
208000035475 disorder Diseases 0.000 description 9
150000002170 ethers Chemical class 0.000 description 9
125000001188 haloalkyl group Chemical group 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
239000003112 inhibitor Substances 0.000 description 9
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 9
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 9
229940083542 sodium Drugs 0.000 description 9
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 9
YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 9
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
235000019270 ammonium chloride Nutrition 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
229940052303 ethers for general anesthesia Drugs 0.000 description 8
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 description 7
UFNHMYRIAGSKMF-UHFFFAOYSA-N 5,7-dichloro-1-(2-ethoxyethyl)-3-ethylpyrazolo[4,3-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2N(CCOCC)N=C(CC)C2=N1 UFNHMYRIAGSKMF-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
125000003545 alkoxy group Chemical group 0.000 description 7
229950011175 aminopicoline Drugs 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
125000005347 halocycloalkyl group Chemical group 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 7
125000003386 piperidinyl group Chemical group 0.000 description 7
150000003138 primary alcohols Chemical class 0.000 description 7
230000009467 reduction Effects 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
208000011580 syndromic disease Diseases 0.000 description 7
150000003512 tertiary amines Chemical class 0.000 description 7
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 6
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
206010019280 Heart failures Diseases 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
229960004132 diethyl ether Drugs 0.000 description 6
229940079593 drug Drugs 0.000 description 6
125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
AKFFNTKRAYWFRN-UHFFFAOYSA-N ethyl 5-(trifluoromethyl)-1h-pyrazole-3-carboxylate Chemical compound CCOC(=O)C=1C=C(C(F)(F)F)NN=1 AKFFNTKRAYWFRN-UHFFFAOYSA-N 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
125000000719 pyrrolidinyl group Chemical group 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
CIKNBRXBEBXORQ-UHFFFAOYSA-N 4-nitro-5-(trifluoromethyl)-1h-pyrazole-3-carboxamide Chemical compound NC(=O)C1=NNC(C(F)(F)F)=C1[N+]([O-])=O CIKNBRXBEBXORQ-UHFFFAOYSA-N 0.000 description 5
PSUXBAOGDOGJBK-UHFFFAOYSA-N 4-nitro-5-(trifluoromethyl)-1h-pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=NNC(C(F)(F)F)=C1[N+]([O-])=O PSUXBAOGDOGJBK-UHFFFAOYSA-N 0.000 description 5
206010002383 Angina Pectoris Diseases 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
206010019233 Headaches Diseases 0.000 description 5
102000004877 Insulin Human genes 0.000 description 5
108090001061 Insulin Proteins 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
206010028980 Neoplasm Diseases 0.000 description 5
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 5
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 5
125000001246 bromo group Chemical group Br* 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000001816 cooling Methods 0.000 description 5
125000000392 cycloalkenyl group Chemical group 0.000 description 5
150000002084 enol ethers Chemical class 0.000 description 5
238000001640 fractional crystallisation Methods 0.000 description 5
125000004438 haloalkoxy group Chemical group 0.000 description 5
125000004356 hydroxy functional group Chemical group O* 0.000 description 5
230000000155 isotopic effect Effects 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
125000003367 polycyclic group Chemical group 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
125000003226 pyrazolyl group Chemical group 0.000 description 5
OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 5
230000009466 transformation Effects 0.000 description 5
230000002792 vascular Effects 0.000 description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 4
FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 4
ALOCUZOKRULSAA-UHFFFAOYSA-N 1-methylpiperidin-4-amine Chemical compound CN1CCC(N)CC1 ALOCUZOKRULSAA-UHFFFAOYSA-N 0.000 description 4
UTWGLBBNAKWLCN-UHFFFAOYSA-N 2-[5-(dimethylamino)-1-(2-ethoxyethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-3-yl]acetaldehyde Chemical compound C=12N(CCOCC)N=C(CC=O)C2=NC(N(C)C)=NC=1NC1=CC(C)=CC=N1 UTWGLBBNAKWLCN-UHFFFAOYSA-N 0.000 description 4
NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 4
BRBUBVKGJRPRRD-UHFFFAOYSA-N 4,6-dimethylpyridin-2-amine Chemical compound CC1=CC(C)=NC(N)=C1 BRBUBVKGJRPRRD-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
BKCDRDWXZVTACN-UHFFFAOYSA-N 5-chloro-3-(chloromethyl)-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC(F)(F)F)N=C(CCl)C2=NC(Cl)=NC=1NC1=CC=NC=N1 BKCDRDWXZVTACN-UHFFFAOYSA-N 0.000 description 4
JXKAUUVMXZIJNZ-UHFFFAOYSA-N 6-ethylpyridin-2-amine Chemical compound CCC1=CC=CC(N)=N1 JXKAUUVMXZIJNZ-UHFFFAOYSA-N 0.000 description 4
ZTAWTRPFJHKMRU-UHFFFAOYSA-N 7-deaza-8-aza-2,6-diaminopurine Chemical class NC1=NC(N)=C2NN=CC2=N1 ZTAWTRPFJHKMRU-UHFFFAOYSA-N 0.000 description 4
229920000858 Cyclodextrin Polymers 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
208000018737 Parkinson disease Diseases 0.000 description 4
201000001880 Sexual dysfunction Diseases 0.000 description 4
208000006011 Stroke Diseases 0.000 description 4
102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 4
108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
125000005036 alkoxyphenyl group Chemical group 0.000 description 4
150000004791 alkyl magnesium halides Chemical class 0.000 description 4
125000002393 azetidinyl group Chemical group 0.000 description 4
239000012267 brine Substances 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
206010012601 diabetes mellitus Diseases 0.000 description 4
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 4
RRANRLASTUBGSJ-UHFFFAOYSA-N dimethyl 4-nitro-1h-pyrazole-3,5-dicarboxylate Chemical compound COC(=O)C1=NNC(C(=O)OC)=C1[N+]([O-])=O RRANRLASTUBGSJ-UHFFFAOYSA-N 0.000 description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
201000010099 disease Diseases 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000000499 gel Substances 0.000 description 4
231100000869 headache Toxicity 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
UKZCGMDMXDLAGZ-UHFFFAOYSA-M magnesium;2-methylpropane;bromide Chemical compound [Mg+2].[Br-].C[C-](C)C UKZCGMDMXDLAGZ-UHFFFAOYSA-M 0.000 description 4
125000002757 morpholinyl group Chemical group 0.000 description 4
229910017604 nitric acid Inorganic materials 0.000 description 4
150000002828 nitro derivatives Chemical class 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000002245 particle Substances 0.000 description 4
RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 4
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 4
150000003141 primary amines Chemical class 0.000 description 4
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 4
235000013772 propylene glycol Nutrition 0.000 description 4
125000003373 pyrazinyl group Chemical group 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
125000000714 pyrimidinyl group Chemical group 0.000 description 4
231100000872 sexual dysfunction Toxicity 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
239000007921 spray Substances 0.000 description 4
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
125000001412 tetrahydropyranyl group Chemical group 0.000 description 4
229910052723 transition metal Inorganic materials 0.000 description 4
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
125000004377 trifluoropropoxy group Chemical group FC(CCO*)(F)F 0.000 description 4
208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
JOMNTHCQHJPVAZ-YFKPBYRVSA-N (2s)-2-methylpiperazine Chemical compound C[C@H]1CNCCN1 JOMNTHCQHJPVAZ-YFKPBYRVSA-N 0.000 description 3
WFRACAPFIGCKJO-UHFFFAOYSA-N 2-[5-(dimethylamino)-1-(2-ethoxyethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-3-yl]ethanol Chemical compound C=12N(CCOCC)N=C(CCO)C2=NC(N(C)C)=NC=1NC1=CC(C)=CC=N1 WFRACAPFIGCKJO-UHFFFAOYSA-N 0.000 description 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 3
BSNWGHKUQKGZCJ-UHFFFAOYSA-N 3-[tert-butyl(dimethyl)silyl]oxy-5-chloro-1-(2-ethoxyethyl)-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(O[Si](C)(C)C(C)(C)C)C2=NC(Cl)=NC=1NC1=CC(C)=CC=N1 BSNWGHKUQKGZCJ-UHFFFAOYSA-N 0.000 description 3
XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 3
AUMADYUKQJLVTK-UHFFFAOYSA-N 5,7-dichloro-1-(2-ethoxyethyl)-3-(trifluoromethyl)pyrazolo[4,3-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2N(CCOCC)N=C(C(F)(F)F)C2=N1 AUMADYUKQJLVTK-UHFFFAOYSA-N 0.000 description 3
JXFTZXVMPBEIOG-UHFFFAOYSA-N 5,7-dichloro-1-[2-(2,2,2-trifluoroethoxy)ethyl]-3-(trifluoromethyl)pyrazolo[4,3-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2N(CCOCC(F)(F)F)N=C(C(F)(F)F)C2=N1 JXFTZXVMPBEIOG-UHFFFAOYSA-N 0.000 description 3
VLAKWWGKRCEHMS-UHFFFAOYSA-N 5-(dimethylamino)-1-(2-ethoxyethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carbaldehyde Chemical compound C=12N(CCOCC)N=C(C=O)C2=NC(N(C)C)=NC=1NC1=CC(C)=CC=N1 VLAKWWGKRCEHMS-UHFFFAOYSA-N 0.000 description 3
JGAMVAKAWLNRGG-UHFFFAOYSA-N 5-chloro-1-(2-ethoxyethyl)-3-(methoxymethyl)-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(Cl)=NC=1NC1=CC=NC=N1 JGAMVAKAWLNRGG-UHFFFAOYSA-N 0.000 description 3
LIEVOSBPDISJOV-UHFFFAOYSA-N 5-chloro-1-(2-ethoxyethyl)-n-(6-ethylpyridin-2-yl)-3-(methoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(Cl)=NC=1NC1=CC=CC(CC)=N1 LIEVOSBPDISJOV-UHFFFAOYSA-N 0.000 description 3
XTPUQGFKKAURLH-UHFFFAOYSA-N 5-ethyl-4-nitro-1h-pyrazole-3-carboxamide Chemical compound CCC=1NN=C(C(N)=O)C=1[N+]([O-])=O XTPUQGFKKAURLH-UHFFFAOYSA-N 0.000 description 3
DLCHCAYDSKIFIN-UHFFFAOYSA-N 5-methyl-3-(trifluoromethyl)-1h-pyrazole Chemical compound CC1=CC(C(F)(F)F)=NN1 DLCHCAYDSKIFIN-UHFFFAOYSA-N 0.000 description 3
QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
208000024172 Cardiovascular disease Diseases 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
208000007342 Diabetic Nephropathies Diseases 0.000 description 3
208000032131 Diabetic Neuropathies Diseases 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
206010022489 Insulin Resistance Diseases 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
208000019693 Lung disease Diseases 0.000 description 3
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 3
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
208000004550 Postoperative Pain Diseases 0.000 description 3
206010064911 Pulmonary arterial hypertension Diseases 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
VEECJKMJRXJGIP-UHFFFAOYSA-N [5-(dimethylamino)-1-(2-ethoxyethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-3-yl]methanol Chemical compound C=12N(CCOCC)N=C(CO)C2=NC(N(C)C)=NC=1NC1=CC(C)=CC=N1 VEECJKMJRXJGIP-UHFFFAOYSA-N 0.000 description 3
238000005903 acid hydrolysis reaction Methods 0.000 description 3
YAJCHEVQCOHZDC-QMMNLEPNSA-N actrapid Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3N=CNC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@H](C)CC)[C@H](C)CC)[C@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C(N)=O)C1=CNC=N1 YAJCHEVQCOHZDC-QMMNLEPNSA-N 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
150000004703 alkoxides Chemical class 0.000 description 3
150000003931 anilides Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052792 caesium Inorganic materials 0.000 description 3
229940088029 cardizem Drugs 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical group C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 3
125000000000 cycloalkoxy group Chemical group 0.000 description 3
150000005690 diesters Chemical class 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000010828 elution Methods 0.000 description 3
239000000066 endothelium dependent relaxing factor Substances 0.000 description 3
HQLRSKMYONCVJM-UHFFFAOYSA-N ethyl 4-nitro-5-(trifluoromethyl)-1h-pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NNC(C(F)(F)F)=C1[N+]([O-])=O HQLRSKMYONCVJM-UHFFFAOYSA-N 0.000 description 3
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
239000010408 film Substances 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
125000002883 imidazolyl group Chemical group 0.000 description 3
201000001881 impotence Diseases 0.000 description 3
208000002551 irritable bowel syndrome Diseases 0.000 description 3
125000000842 isoxazolyl group Chemical group 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000012669 liquid formulation Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
208000030159 metabolic disease Diseases 0.000 description 3
SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 3
125000006431 methyl cyclopropyl group Chemical group 0.000 description 3
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 3
201000006417 multiple sclerosis Diseases 0.000 description 3
210000003205 muscle Anatomy 0.000 description 3
208000010125 myocardial infarction Diseases 0.000 description 3
238000006396 nitration reaction Methods 0.000 description 3
239000002840 nitric oxide donor Substances 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
125000001715 oxadiazolyl group Chemical group 0.000 description 3
125000002971 oxazolyl group Chemical group 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 3
238000002638 palliative care Methods 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
125000004193 piperazinyl group Chemical group 0.000 description 3
239000012286 potassium permanganate Substances 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
125000002098 pyridazinyl group Chemical group 0.000 description 3
JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 description 3
230000008085 renal dysfunction Effects 0.000 description 3
150000003335 secondary amines Chemical group 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
FDGZZTICDKUCIA-UHFFFAOYSA-N sodium;cyclopropylmethanolate Chemical compound [Na+].[O-]CC1CC1 FDGZZTICDKUCIA-UHFFFAOYSA-N 0.000 description 3
239000000758 substrate Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
SCBVFHHXDSXYKA-UHFFFAOYSA-N tert-butyl 4-[3-[tert-butyl(dimethyl)silyl]oxy-1-(2-ethoxyethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical compound C=12N(CCOCC)N=C(O[Si](C)(C)C(C)(C)C)C2=NC(N2CCN(CC2)C(=O)OC(C)(C)C)=NC=1NC1=CC(C)=CC=N1 SCBVFHHXDSXYKA-UHFFFAOYSA-N 0.000 description 3
125000005207 tetraalkylammonium group Chemical group 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
238000012546 transfer Methods 0.000 description 3
HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 description 2
HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 2
CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
QEASJVYPHMYPJM-UHFFFAOYSA-N 1,2-dihydrotriazol-5-one Chemical compound OC1=CNN=N1 QEASJVYPHMYPJM-UHFFFAOYSA-N 0.000 description 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
MMYKTRPLXXWLBC-UHFFFAOYSA-N 1-bromo-2-ethoxyethane Chemical compound CCOCCBr MMYKTRPLXXWLBC-UHFFFAOYSA-N 0.000 description 2
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
KASVWBYINCPZIG-UHFFFAOYSA-N 141721-97-3 Chemical compound CC(C)C=1NN=C(C(O)=O)C=1[N+]([O-])=O KASVWBYINCPZIG-UHFFFAOYSA-N 0.000 description 2
RQFCJASXJCIDSX-UHFFFAOYSA-N 14C-Guanosin-5'-monophosphat Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(COP(O)(O)=O)C(O)C1O RQFCJASXJCIDSX-UHFFFAOYSA-N 0.000 description 2
KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
YJESXPJLNPVMAS-UHFFFAOYSA-N 3-(2-chloroethyl)-1-(2-ethoxyethyl)-5-n,5-n-dimethyl-7-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidine-5,7-diamine Chemical compound C=12N(CCOCC)N=C(CCCl)C2=NC(N(C)C)=NC=1NC1=CC(C)=CC=N1 YJESXPJLNPVMAS-UHFFFAOYSA-N 0.000 description 2
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 2
YCFMAXYHXWUZNJ-UHFFFAOYSA-N 4-amino-2-(2-ethoxyethyl)-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound CCOCCN1N=C(C(F)(F)F)C(N)=C1C(N)=O YCFMAXYHXWUZNJ-UHFFFAOYSA-N 0.000 description 2
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 2
XHVOHNXZRCGUEH-UHFFFAOYSA-N 4-nitro-5-propan-2-yl-1h-pyrazole-3-carboxamide Chemical compound CC(C)C=1NN=C(C(N)=O)C=1[N+]([O-])=O XHVOHNXZRCGUEH-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
IWBORWUNXZWLEO-CALCHBBNSA-N 5-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-n-(5-methylpyridin-2-yl)-3-propan-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)N[C@@H](C)C2)N=C2C(C(C)C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 IWBORWUNXZWLEO-CALCHBBNSA-N 0.000 description 2
JPQMZTOCAWXLJU-UHFFFAOYSA-N 5-chloro-3-(chloromethyl)-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC(F)(F)F)N=C(CCl)C2=NC(Cl)=NC=1NC1=CC=CC=N1 JPQMZTOCAWXLJU-UHFFFAOYSA-N 0.000 description 2
LTWDWTYATSOYLQ-UHFFFAOYSA-N 5-chloro-3-(ethoxymethyl)-n-(6-methylpyridin-2-yl)-1-(2-propoxyethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COCC)C2=NC(Cl)=NC=1NC1=CC=CC(C)=N1 LTWDWTYATSOYLQ-UHFFFAOYSA-N 0.000 description 2
JSNYFZRWPDDAPD-UHFFFAOYSA-N 5-chloro-3-(ethoxymethyl)-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(Cl)N=C2C(COCC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 JSNYFZRWPDDAPD-UHFFFAOYSA-N 0.000 description 2
LDQQVKFDBUMGEQ-UHFFFAOYSA-N 5-chloro-n-(4,6-dimethylpyridin-2-yl)-1-(2-ethoxyethyl)-3-(ethoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(Cl)=NC=1NC1=CC(C)=CC(C)=N1 LDQQVKFDBUMGEQ-UHFFFAOYSA-N 0.000 description 2
BDOLBAYXGBJXKF-UHFFFAOYSA-N 5-chloro-n-(4,6-dimethylpyridin-2-yl)-1-(2-ethoxyethyl)-3-(methoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(Cl)=NC=1NC1=CC(C)=CC(C)=N1 BDOLBAYXGBJXKF-UHFFFAOYSA-N 0.000 description 2
MWTOSFMGNUDEHY-UHFFFAOYSA-N 5-methyl-4-nitro-1h-pyrazole-3-carboxamide Chemical compound CC=1NN=C(C(N)=O)C=1[N+]([O-])=O MWTOSFMGNUDEHY-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
UXOWGYHJODZGMF-QORCZRPOSA-N Aliskiren Chemical compound COCCCOC1=CC(C[C@@H](C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)C(C)C)=CC=C1OC UXOWGYHJODZGMF-QORCZRPOSA-N 0.000 description 2
208000024827 Alzheimer disease Diseases 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
208000008035 Back Pain Diseases 0.000 description 2
206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
101800000407 Brain natriuretic peptide 32 Proteins 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
206010058019 Cancer Pain Diseases 0.000 description 2
241000819038 Chichester Species 0.000 description 2
229920001268 Cholestyramine Polymers 0.000 description 2
201000006705 Congenital generalized lipodystrophy Diseases 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
206010012289 Dementia Diseases 0.000 description 2
201000005948 Donohue syndrome Diseases 0.000 description 2
208000010228 Erectile Dysfunction Diseases 0.000 description 2
206010016059 Facial pain Diseases 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
208000010412 Glaucoma Diseases 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
206010061216 Infarction Diseases 0.000 description 2
108010065920 Insulin Lispro Proteins 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
208000019695 Migraine disease Diseases 0.000 description 2
238000006751 Mitsunobu reaction Methods 0.000 description 2
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000007126 N-alkylation reaction Methods 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
102000003729 Neprilysin Human genes 0.000 description 2
108090000028 Neprilysin Proteins 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
102000008299 Nitric Oxide Synthase Human genes 0.000 description 2
108010021487 Nitric Oxide Synthase Proteins 0.000 description 2
208000001132 Osteoporosis Diseases 0.000 description 2
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
208000018262 Peripheral vascular disease Diseases 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
206010036376 Postherpetic Neuralgia Diseases 0.000 description 2
208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
208000012322 Raynaud phenomenon Diseases 0.000 description 2
206010062237 Renal impairment Diseases 0.000 description 2
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 description 2
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 2
238000007239 Wittig reaction Methods 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
230000007000 age related cognitive decline Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000004849 alkoxymethyl group Chemical group 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000002399 angioplasty Methods 0.000 description 2
230000002917 arthritic effect Effects 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000005604 azodicarboxylate group Chemical group 0.000 description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
RVSSYVYJECMDPC-UHFFFAOYSA-N benzyl 4-[1-(2-ethoxyethyl)-3-(2-hydroxyethyl)-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical compound C=12N(CCOCC)N=C(CCO)C2=NC(N2CCN(CC2)C(=O)OCC=2C=CC=CC=2)=NC=1NC1=CC=NC=N1 RVSSYVYJECMDPC-UHFFFAOYSA-N 0.000 description 2
PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 2
239000002876 beta blocker Substances 0.000 description 2
229940097320 beta blocking agent Drugs 0.000 description 2
239000003613 bile acid Substances 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
238000009835 boiling Methods 0.000 description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
229910000024 caesium carbonate Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000000969 carrier Substances 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
208000015114 central nervous system disease Diseases 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
239000007822 coupling agent Substances 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
208000033679 diabetic kidney disease Diseases 0.000 description 2
150000008049 diazo compounds Chemical class 0.000 description 2
208000016097 disease of metabolism Diseases 0.000 description 2
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
230000004064 dysfunction Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000132 electrospray ionisation Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
125000001207 fluorophenyl group Chemical group 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 2
ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
238000005469 granulation Methods 0.000 description 2
230000003179 granulation Effects 0.000 description 2
RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
WNRQPCUGRUFHED-DETKDSODSA-N humalog Chemical compound C([C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(O)=O)C1=CC=C(O)C=C1.C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CS)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 WNRQPCUGRUFHED-DETKDSODSA-N 0.000 description 2
229940038661 humalog Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
239000007943 implant Substances 0.000 description 2
230000007574 infarction Effects 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
238000002955 isolation Methods 0.000 description 2
125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 description 2
125000001786 isothiazolyl group Chemical group 0.000 description 2
238000010902 jet-milling Methods 0.000 description 2
239000002502 liposome Substances 0.000 description 2
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
206010027599 migraine Diseases 0.000 description 2
239000003595 mist Substances 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
235000001968 nicotinic acid Nutrition 0.000 description 2
239000011664 nicotinic acid Substances 0.000 description 2
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
238000006053 organic reaction Methods 0.000 description 2
201000008482 osteoarthritis Diseases 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
230000002093 peripheral effect Effects 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
239000003444 phase transfer catalyst Substances 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 2
DBMHTLOVZSDLFD-UHFFFAOYSA-N piperidin-1-ylmethanamine Chemical compound NCN1CCCCC1 DBMHTLOVZSDLFD-UHFFFAOYSA-N 0.000 description 2
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229960003975 potassium Drugs 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000003380 propellant Substances 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
150000003217 pyrazoles Chemical class 0.000 description 2
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 2
125000000168 pyrrolyl group Chemical group 0.000 description 2
230000002285 radioactive effect Effects 0.000 description 2
238000004366 reverse phase liquid chromatography Methods 0.000 description 2
238000004007 reversed phase HPLC Methods 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
238000012552 review Methods 0.000 description 2
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
150000003333 secondary alcohols Chemical class 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
230000001568 sexual effect Effects 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
WELFBGSXCZXFDT-UHFFFAOYSA-N sodium;3,3,3-trifluoropropan-1-olate Chemical compound [Na+].[O-]CCC(F)(F)F WELFBGSXCZXFDT-UHFFFAOYSA-N 0.000 description 2
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 2
208000020431 spinal cord injury Diseases 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
238000010189 synthetic method Methods 0.000 description 2
RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 2
GPMGXEONBWICPF-UHFFFAOYSA-N tert-butyl 4-[1-(2-ethoxyethyl)-3-(1-hydroxyethyl)-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical compound C=12N(CCOCC)N=C(C(C)O)C2=NC(N2CCN(CC2)C(=O)OC(C)(C)C)=NC=1NC1=CC=NC=N1 GPMGXEONBWICPF-UHFFFAOYSA-N 0.000 description 2
HUVXBRMYDNUDQX-UHFFFAOYSA-N tert-butyl 4-[1-(2-ethoxyethyl)-3-(hydroxymethyl)-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical group C=12N(CCOCC)N=C(CO)C2=NC(N2CCN(CC2)C(=O)OC(C)(C)C)=NC=1NC1=CC=NC=N1 HUVXBRMYDNUDQX-UHFFFAOYSA-N 0.000 description 2
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000009901 transfer hydrogenation reaction Methods 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
125000004665 trialkylsilyl group Chemical group 0.000 description 2
230000002861 ventricular Effects 0.000 description 2
208000009935 visceral pain Diseases 0.000 description 2
239000003039 volatile agent Substances 0.000 description 2
235000012431 wafers Nutrition 0.000 description 2
UKHJNJFJCGBKSF-WHFBIAKZSA-N (1s,4s)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1N[C@]2([H])CN[C@@]1([H])C2 UKHJNJFJCGBKSF-WHFBIAKZSA-N 0.000 description 1
XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
NVXFXLSOGLFXKQ-JMSVASOKSA-N (2s)-1-[(2r,4r)-5-ethoxy-2,4-dimethyl-5-oxopentanoyl]-2,3-dihydroindole-2-carboxylic acid Chemical compound C1=CC=C2N(C(=O)[C@H](C)C[C@@H](C)C(=O)OCC)[C@H](C(O)=O)CC2=C1 NVXFXLSOGLFXKQ-JMSVASOKSA-N 0.000 description 1
ZBOYJODMIAUJHH-SANMLTNESA-N (2s)-1-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C=1C(OC)=C(CN2[C@@H](CCCC2)C(O)=O)C(OC)=CC=1OCC(C=1C)=CC=CC=1C1=CC=CC=C1 ZBOYJODMIAUJHH-SANMLTNESA-N 0.000 description 1
GKYIONYOYVKKQI-MPGHIAIKSA-N (2s)-2-[[(2s,3r)-2-(benzoylsulfanylmethyl)-3-phenylbutanoyl]amino]propanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C)C(O)=O)[C@@H](C)C=1C=CC=CC=1)SC(=O)C1=CC=CC=C1 GKYIONYOYVKKQI-MPGHIAIKSA-N 0.000 description 1
LPUDGHQMOAHMMF-JBACZVJFSA-N (2s)-2-[[[(2s)-6-amino-2-(methanesulfonamido)hexanoyl]amino]methyl]-3-[1-[[(1s)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl]cyclopentyl]propanoic acid Chemical compound N([C@@H](CC=1C=CC(O)=CC=1)C(O)=O)C(=O)C1(C[C@@H](CNC(=O)[C@H](CCCCN)NS(=O)(=O)C)C(O)=O)CCCC1 LPUDGHQMOAHMMF-JBACZVJFSA-N 0.000 description 1
ZONOMVGGONAQQA-QTBHSTJXSA-N (2s)-2-acetamidopropanoic acid;[3-[[(2r)-1-ethenoxy-3-sulfanylidenepropan-2-yl]amino]-2,2-dimethyl-3-oxopropyl] nitrate Chemical compound OC(=O)[C@H](C)NC(C)=O.[O-][N+](=O)OCC(C)(C)C(=O)N[C@H](COC=C)C=S ZONOMVGGONAQQA-QTBHSTJXSA-N 0.000 description 1
XMBSMMCPKFDGEO-ZETCQYMHSA-N (2s)-2-amino-5-[[amino-(2-methoxyethylamino)methylidene]amino]pentanoic acid Chemical compound COCCNC(=N)NCCC[C@H](N)C(O)=O XMBSMMCPKFDGEO-ZETCQYMHSA-N 0.000 description 1
BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 description 1
YWUIUNGMQOICND-UHFFFAOYSA-N (2z)-2-diazo-1,1,1-trifluoroethane Chemical compound FC(F)(F)C=[N+]=[N-] YWUIUNGMQOICND-UHFFFAOYSA-N 0.000 description 1
ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
LHQBWMOHKDFGBX-CQSZACIVSA-N (3r)-1-[1-(2-ethoxyethyl)-3-ethyl-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](CCC2)C(O)=O)=NC=1NC1=CC=NC=N1 LHQBWMOHKDFGBX-CQSZACIVSA-N 0.000 description 1
PZHUMIQRRYMFBV-OAHLLOKOSA-N (3r)-1-[1-(2-ethoxyethyl)-3-methyl-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@@H](CCC2)C(O)=O)=NC=1NC1=CC=CC=N1 PZHUMIQRRYMFBV-OAHLLOKOSA-N 0.000 description 1
MHBSPPKZNIWRQH-CQSZACIVSA-N (3r)-1-[1-(2-ethoxyethyl)-3-methyl-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@@H](CCC2)C(O)=O)=NC=1NC1=CC=NC=N1 MHBSPPKZNIWRQH-CQSZACIVSA-N 0.000 description 1
AFNXCAWUYNRJCT-CYBMUJFWSA-N (3r)-1-[1-(2-ethoxyethyl)-3-methyl-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@@H](CC2)C(N)=O)=NC=1NC1=CC=NC=N1 AFNXCAWUYNRJCT-CYBMUJFWSA-N 0.000 description 1
ZXMZVSFWVARMRI-OAHLLOKOSA-N (3r)-1-[1-(2-ethoxyethyl)-3-methyl-7-[(5-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@@H](CC2)C(O)=O)=NC=1NC1=CC=C(C)C=N1 ZXMZVSFWVARMRI-OAHLLOKOSA-N 0.000 description 1
FBRAAMVMTBLDQY-MRXNPFEDSA-N (3r)-1-[1-(2-ethoxyethyl)-3-propan-2-yl-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C(C)C)C2=NC(N2C[C@@H](CCC2)C(O)=O)=NC=1NC1=CC=CC=N1 FBRAAMVMTBLDQY-MRXNPFEDSA-N 0.000 description 1
DRVWOMREQWCBCD-CYBMUJFWSA-N (3r)-1-[1-(2-ethoxyethyl)-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound C=12N(CCOCC)N=CC2=NC(N2C[C@@H](CC2)C(N)=O)=NC=1NC1=CC=CC=N1 DRVWOMREQWCBCD-CYBMUJFWSA-N 0.000 description 1
QEKPMMUZRWQQSX-CQSZACIVSA-N (3r)-1-[3-ethyl-7-[(5-methylpyridin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound N1=C(N2C[C@@H](CC2)C(N)=O)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 QEKPMMUZRWQQSX-CQSZACIVSA-N 0.000 description 1
FLLMVGWHRDFQNJ-CQSZACIVSA-N (3r)-1-[3-methyl-7-(pyridin-2-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound N1=C(N2C[C@@H](CCC2)C(O)=O)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 FLLMVGWHRDFQNJ-CQSZACIVSA-N 0.000 description 1
HTCCWWLKQKVHFE-OAHLLOKOSA-N (3r)-1-[3-methyl-7-[(5-methylpyridin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound N1=C(N2C[C@@H](CCC2)C(O)=O)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 HTCCWWLKQKVHFE-OAHLLOKOSA-N 0.000 description 1
WOSKVLDLPSAZDR-CQSZACIVSA-N (3r)-1-[3-methyl-7-[(5-methylpyridin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxylic acid Chemical compound N1=C(N2C[C@@H](CC2)C(O)=O)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 WOSKVLDLPSAZDR-CQSZACIVSA-N 0.000 description 1
CKFWDLFFXXVSBJ-DHIUTWEWSA-N (3r,5r)-3-butyl-3-ethyl-7,8-dimethoxy-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound C1([C@@H]2C3=CC(OC)=C(OC)C=C3S(=O)(=O)C[C@@](N2)(CC)CCCC)=CC=CC=C1 CKFWDLFFXXVSBJ-DHIUTWEWSA-N 0.000 description 1
KOGUODJHOARITL-HNNXBMFYSA-N (3s)-1-[1-(2-ethoxyethyl)-3-ethyl-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@H](CCC2)C(O)=O)=NC=1NC1=CC=CC=N1 KOGUODJHOARITL-HNNXBMFYSA-N 0.000 description 1
VOKIQBXXDUJVGK-AWEZNQCLSA-N (3s)-1-[1-(2-ethoxyethyl)-3-ethyl-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@H](CC2)C(O)=O)=NC=1NC1=CC=CC=N1 VOKIQBXXDUJVGK-AWEZNQCLSA-N 0.000 description 1
PZHUMIQRRYMFBV-HNNXBMFYSA-N (3s)-1-[1-(2-ethoxyethyl)-3-methyl-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@H](CCC2)C(O)=O)=NC=1NC1=CC=CC=N1 PZHUMIQRRYMFBV-HNNXBMFYSA-N 0.000 description 1
FDXMIZCVANTTMN-ZDUSSCGKSA-N (3s)-1-[1-(2-ethoxyethyl)-3-methyl-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@H](CC2)C(O)=O)=NC=1NC1=CC=NC=N1 FDXMIZCVANTTMN-ZDUSSCGKSA-N 0.000 description 1
WRFVCDRMGVQLRO-INIZCTEOSA-N (3s)-1-[1-(2-ethoxyethyl)-3-methyl-7-[(5-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@H](CCC2)C(O)=O)=NC=1NC1=CC=C(C)C=N1 WRFVCDRMGVQLRO-INIZCTEOSA-N 0.000 description 1
FBRAAMVMTBLDQY-INIZCTEOSA-N (3s)-1-[1-(2-ethoxyethyl)-3-propan-2-yl-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C(C)C)C2=NC(N2C[C@H](CCC2)C(O)=O)=NC=1NC1=CC=CC=N1 FBRAAMVMTBLDQY-INIZCTEOSA-N 0.000 description 1
DBDHVODCAUVLLH-ZDUSSCGKSA-N (3s)-1-[1-(2-ethoxyethyl)-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=CC2=NC(N2C[C@H](CC2)C(O)=O)=NC=1NC1=CC=CC=N1 DBDHVODCAUVLLH-ZDUSSCGKSA-N 0.000 description 1
JHDBQWMNXFVNON-ZDUSSCGKSA-N (3s)-1-[1-(2-ethoxyethyl)-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=CC2=NC(N2C[C@H](CCC2)C(O)=O)=NC=1NC1=CC=NC=N1 JHDBQWMNXFVNON-ZDUSSCGKSA-N 0.000 description 1
QNRZMBRYALZVEP-AWEZNQCLSA-N (3s)-1-[3-ethyl-7-(pyridin-2-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound N1=C(N2C[C@H](CCC2)C(O)=O)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 QNRZMBRYALZVEP-AWEZNQCLSA-N 0.000 description 1
JLACUTOJARXNLY-ZDUSSCGKSA-N (3s)-1-[3-ethyl-7-(pyridin-2-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxylic acid Chemical compound N1=C(N2C[C@H](CC2)C(O)=O)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 JLACUTOJARXNLY-ZDUSSCGKSA-N 0.000 description 1
VZHMOUHUHWLMPH-HNNXBMFYSA-N (3s)-1-[3-ethyl-7-[(5-methylpyridin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound N1=C(N2C[C@H](CCC2)C(O)=O)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 VZHMOUHUHWLMPH-HNNXBMFYSA-N 0.000 description 1
NENOXVJBLVLWRY-ZDUSSCGKSA-N (3s)-1-[3-methyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound N1=C(N2C[C@H](CCC2)C(O)=O)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 NENOXVJBLVLWRY-ZDUSSCGKSA-N 0.000 description 1
HTCCWWLKQKVHFE-HNNXBMFYSA-N (3s)-1-[3-methyl-7-[(5-methylpyridin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound N1=C(N2C[C@H](CCC2)C(O)=O)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 HTCCWWLKQKVHFE-HNNXBMFYSA-N 0.000 description 1
WCAPOFOUNKTWDC-ZDUSSCGKSA-N (3s)-1-[7-(pyridin-2-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C1[C@@H](C(=O)O)CCCN1C1=NC(NC=2N=CC=CC=2)=C(N(CCOCC(F)(F)F)N=C2)C2=N1 WCAPOFOUNKTWDC-ZDUSSCGKSA-N 0.000 description 1
PQRDQUCQFYFJBS-LBPRGKRZSA-N (3s)-1-[7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]piperidine-3-carboxylic acid Chemical compound C1[C@@H](C(=O)O)CCCN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2)C2=N1 PQRDQUCQFYFJBS-LBPRGKRZSA-N 0.000 description 1
TYWGMLORNCVYBR-ZDUSSCGKSA-N (3s)-1-[7-[(5-methylpyridin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxylic acid Chemical compound N1=CC(C)=CC=C1NC1=NC(N2C[C@H](CC2)C(O)=O)=NC2=C1N(CCOCC(F)(F)F)N=C2 TYWGMLORNCVYBR-ZDUSSCGKSA-N 0.000 description 1
TWZGTRJIOQHMDR-HNNXBMFYSA-N (3s)-1-[7-[(5-methylpyridin-2-yl)amino]-3-propan-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxylic acid Chemical compound N1=C(N2C[C@H](CC2)C(O)=O)N=C2C(C(C)C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 TWZGTRJIOQHMDR-HNNXBMFYSA-N 0.000 description 1
VTAANPGBUKBPKX-AWEZNQCLSA-N (3s)-n-[1-(2-ethoxyethyl)-3-ethyl-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC(=O)[C@H]1CCNC1 VTAANPGBUKBPKX-AWEZNQCLSA-N 0.000 description 1
JFJWXNYCHZADMC-ZDUSSCGKSA-N (3s)-n-[1-(2-ethoxyethyl)-3-ethyl-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound N=1C(NC=2N=CN=CC=2)=C2N(CCOCC)N=C(CC)C2=NC=1NC(=O)[C@H]1CCNC1 JFJWXNYCHZADMC-ZDUSSCGKSA-N 0.000 description 1
JQDSQSRRZYVEMT-AWEZNQCLSA-N (3s)-n-[1-(2-ethoxyethyl)-3-methyl-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC)N=C(C)C2=NC=1NC(=O)[C@H]1CCNC1 JQDSQSRRZYVEMT-AWEZNQCLSA-N 0.000 description 1
WANRFMACXSGKMS-LBPRGKRZSA-N (3s)-n-[3-ethyl-7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound N1=C(NC(=O)[C@@H]2CNCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=NC=N1 WANRFMACXSGKMS-LBPRGKRZSA-N 0.000 description 1
OGVVSONPVLPMNW-AWEZNQCLSA-N (3s)-n-[3-methyl-7-[(5-methylpyridin-2-yl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound N1=C(NC(=O)[C@@H]2CNCC2)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 OGVVSONPVLPMNW-AWEZNQCLSA-N 0.000 description 1
IHSUDEHHQZUGRF-AWEZNQCLSA-N (3s)-n-[3-propan-2-yl-7-(pyridin-2-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound N1=C(NC(=O)[C@@H]2CNCC2)N=C2C(C(C)C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 IHSUDEHHQZUGRF-AWEZNQCLSA-N 0.000 description 1
KFJPGNQJANZMLL-LBPRGKRZSA-N (3s)-n-[7-(pyridin-2-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound N=1C(NC=2N=CC=CC=2)=C2N(CCOCC(F)(F)F)N=CC2=NC=1NC(=O)[C@H]1CCNC1 KFJPGNQJANZMLL-LBPRGKRZSA-N 0.000 description 1
XVYXCICEUDQOFG-NSHDSACASA-N (3s)-n-[7-(pyrimidin-4-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-5-yl]pyrrolidine-3-carboxamide Chemical compound N=1C(NC=2N=CN=CC=2)=C2N(CCOCC(F)(F)F)N=CC2=NC=1NC(=O)[C@H]1CCNC1 XVYXCICEUDQOFG-NSHDSACASA-N 0.000 description 1
KKXFMWXZXDUYBF-BDAKNGLRSA-N (3s,5r)-3-(aminomethyl)-5-methyloctanoic acid Chemical compound CCC[C@@H](C)C[C@H](CN)CC(O)=O KKXFMWXZXDUYBF-BDAKNGLRSA-N 0.000 description 1
GUEQOLSQPOTTME-RQJHMYQMSA-N (3s,5r)-3-amino-5-methylheptanoic acid Chemical compound CC[C@@H](C)C[C@H](N)CC(O)=O GUEQOLSQPOTTME-RQJHMYQMSA-N 0.000 description 1
XKWDZEJCUWTBOM-BDAKNGLRSA-N (3s,5r)-3-amino-5-methylnonanoic acid Chemical compound CCCC[C@@H](C)C[C@H](N)CC(O)=O XKWDZEJCUWTBOM-BDAKNGLRSA-N 0.000 description 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 description 1
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
SIWVGXQOXWGJCI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;2-ethenylbenzenesulfonic acid Chemical compound C=CC1=CC=CC=C1C=C.OS(=O)(=O)C1=CC=CC=C1C=C SIWVGXQOXWGJCI-UHFFFAOYSA-N 0.000 description 1
XXZGTQWSPXACIV-UHFFFAOYSA-N 1-(2,2,2-trifluoroethoxy)ethanol Chemical compound CC(O)OCC(F)(F)F XXZGTQWSPXACIV-UHFFFAOYSA-N 0.000 description 1
BQYZDMNAARQHKR-UHFFFAOYSA-N 1-(2-bromoethoxy)propane Chemical compound CCCOCCBr BQYZDMNAARQHKR-UHFFFAOYSA-N 0.000 description 1
XFHPRYZSVGTEEI-MRXNPFEDSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3r)-3-ethylpiperazin-1-yl]-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](CC)NCC2)=NC=1NC1=CC=CC=N1 XFHPRYZSVGTEEI-MRXNPFEDSA-N 0.000 description 1
XFHPRYZSVGTEEI-INIZCTEOSA-N 1-(2-ethoxyethyl)-3-ethyl-5-[(3s)-3-ethylpiperazin-1-yl]-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@H](CC)NCC2)=NC=1NC1=CC=CC=N1 XFHPRYZSVGTEEI-INIZCTEOSA-N 0.000 description 1
PTMRXAVVDWQRBW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-ethyl-5-piperazin-1-yl-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCC2)=NC=1NC1=CC=NC=N1 PTMRXAVVDWQRBW-UHFFFAOYSA-N 0.000 description 1
MQRBPSSFVSBWSR-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-methyl-5-piperazin-1-yl-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCNCC2)=NC=1NC1=CC=NC=N1 MQRBPSSFVSBWSR-UHFFFAOYSA-N 0.000 description 1
WMSDNZPDNXKRSA-MRXNPFEDSA-N 1-(2-ethoxyethyl)-5-[(3r)-3-ethylpiperazin-1-yl]-3-methyl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2C[C@@H](CC)NCC2)=NC=1NC1=CC=CC=N1 WMSDNZPDNXKRSA-MRXNPFEDSA-N 0.000 description 1
CODIZTIZGBWIKN-QGZVFWFLSA-N 1-(2-ethoxyethyl)-5-[(3r)-3-ethylpiperazin-1-yl]-3-propan-2-yl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C(C)C)C2=NC(N2C[C@@H](CC)NCC2)=NC=1NC1=CC=CC=N1 CODIZTIZGBWIKN-QGZVFWFLSA-N 0.000 description 1
ARDAARCLSUALQA-GOSISDBHSA-N 1-(2-ethoxyethyl)-5-[(3r)-3-ethylpiperazin-1-yl]-n-(5-methylpyridin-2-yl)-3-propan-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C(C)C)C2=NC(N2C[C@@H](CC)NCC2)=NC=1NC1=CC=C(C)C=N1 ARDAARCLSUALQA-GOSISDBHSA-N 0.000 description 1
MPORVVMPXUXLFJ-CQSZACIVSA-N 1-(2-ethoxyethyl)-5-[(3r)-3-ethylpiperazin-1-yl]-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=CC2=NC(N2C[C@@H](CC)NCC2)=NC=1NC1=CC=NC=N1 MPORVVMPXUXLFJ-CQSZACIVSA-N 0.000 description 1
HELWOMDTOSGEGC-MRXNPFEDSA-N 1-(2-ethoxyethyl)-5-[(3r)-3-methylpiperazin-1-yl]-3-propan-2-yl-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C(C)C)C2=NC(N2C[C@@H](C)NCC2)=NC=1NC1=CC=CC=N1 HELWOMDTOSGEGC-MRXNPFEDSA-N 0.000 description 1
CAXAHOAOGWXJCJ-INIZCTEOSA-N 1-(2-ethoxyethyl)-5-[(3s)-3-ethylpiperazin-1-yl]-n-(5-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=CC2=NC(N2C[C@H](CC)NCC2)=NC=1NC1=CC=C(C)C=N1 CAXAHOAOGWXJCJ-INIZCTEOSA-N 0.000 description 1
XDRZFWPWRKKFKI-HNNXBMFYSA-N 1-(2-ethoxyethyl)-5-[(3s)-3-ethylpiperazin-1-yl]-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=CC2=NC(N2C[C@H](CC)NCC2)=NC=1NC1=CC=CC=N1 XDRZFWPWRKKFKI-HNNXBMFYSA-N 0.000 description 1
MPORVVMPXUXLFJ-AWEZNQCLSA-N 1-(2-ethoxyethyl)-5-[(3s)-3-ethylpiperazin-1-yl]-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=CC2=NC(N2C[C@H](CC)NCC2)=NC=1NC1=CC=NC=N1 MPORVVMPXUXLFJ-AWEZNQCLSA-N 0.000 description 1
IMNKZAWXTOQTRM-HNNXBMFYSA-N 1-(2-ethoxyethyl)-5-[(3s)-3-methylpiperazin-1-yl]-n-(5-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=CC2=NC(N2C[C@H](C)NCC2)=NC=1NC1=CC=C(C)C=N1 IMNKZAWXTOQTRM-HNNXBMFYSA-N 0.000 description 1
GYGMMOKNMNPDBL-UHFFFAOYSA-N 1-(2-ethoxyethyl)-n-(5-methylpyridin-2-yl)-5-piperazin-1-yl-3-propan-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C(C)C)C2=NC(N2CCNCC2)=NC=1NC1=CC=C(C)C=N1 GYGMMOKNMNPDBL-UHFFFAOYSA-N 0.000 description 1
TYODDTFWIMEWAD-UHFFFAOYSA-N 1-ethoxy-3-iodopropane Chemical compound CCOCCCI TYODDTFWIMEWAD-UHFFFAOYSA-N 0.000 description 1
WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
FLNMQGISZVYIIK-UHFFFAOYSA-N 1-ethylpyrazole Chemical compound CCN1C=CC=N1 FLNMQGISZVYIIK-UHFFFAOYSA-N 0.000 description 1
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical class C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 1
BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 1
FSKYZRCACCHDGR-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidin-4-one Chemical class C1=CN=C2C(=O)N=CNC2=C1 FSKYZRCACCHDGR-UHFFFAOYSA-N 0.000 description 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
VTKJONLXRSQSGR-UHFFFAOYSA-N 2,3,6,6a,7,7a-hexahydropyrazino[1,2-b]$b-carboline-1,4-quinone Chemical class C1=CC=CC2NC(CN3C(=O)CNC(=O)C3=C3)C3=C21 VTKJONLXRSQSGR-UHFFFAOYSA-N 0.000 description 1
GVOIPDXOCSEXRH-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)-n-[(2,2,2-trifluoro-1-triphenylsilylethylidene)amino]benzenesulfonamide Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1S(=O)(=O)NN=C(C(F)(F)F)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GVOIPDXOCSEXRH-UHFFFAOYSA-N 0.000 description 1
ISYQWKOXKGJREA-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane;dihydrobromide Chemical compound Br.Br.C1NC2CNC1C2 ISYQWKOXKGJREA-UHFFFAOYSA-N 0.000 description 1
HRBLSBRWIWIOGW-UHFFFAOYSA-N 2-(2,2,2-trifluoroethoxy)ethanol Chemical compound OCCOCC(F)(F)F HRBLSBRWIWIOGW-UHFFFAOYSA-N 0.000 description 1
KYKUZTBLYLKPIT-UHFFFAOYSA-N 2-(2-bromoethoxy)propane Chemical compound CC(C)OCCBr KYKUZTBLYLKPIT-UHFFFAOYSA-N 0.000 description 1
DAUXKAKXMYWKLU-UHFFFAOYSA-N 2-(2-ethoxyethyl)-4-nitro-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound CCOCCN1N=C(C(F)(F)F)C([N+]([O-])=O)=C1C(N)=O DAUXKAKXMYWKLU-UHFFFAOYSA-N 0.000 description 1
LCMJCOHUPUWCGZ-UHFFFAOYSA-N 2-(2-ethoxyethyl)-5-methoxycarbonyl-4-nitropyrazole-3-carboxylic acid Chemical compound CCOCCN1N=C(C(=O)OC)C([N+]([O-])=O)=C1C(O)=O LCMJCOHUPUWCGZ-UHFFFAOYSA-N 0.000 description 1
ACRKYRIOLWFSMK-UHFFFAOYSA-N 2-(2-ethoxyethyl)-n-ethyl-4-nitro-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound CCNC(=O)C1=C([N+]([O-])=O)C(C(F)(F)F)=NN1CCOCC ACRKYRIOLWFSMK-UHFFFAOYSA-N 0.000 description 1
YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
VTAKZNRDSPNOAU-UHFFFAOYSA-M 2-(chloromethyl)oxirane;hydron;prop-2-en-1-amine;n-prop-2-enyldecan-1-amine;trimethyl-[6-(prop-2-enylamino)hexyl]azanium;dichloride Chemical compound Cl.[Cl-].NCC=C.ClCC1CO1.CCCCCCCCCCNCC=C.C[N+](C)(C)CCCCCCNCC=C VTAKZNRDSPNOAU-UHFFFAOYSA-M 0.000 description 1
GHCFWKFREBNSPC-UHFFFAOYSA-N 2-Amino-4-methylpyrimidine Chemical compound CC1=CC=NC(N)=N1 GHCFWKFREBNSPC-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
JXSBZOVCVUSLIO-NQMVMOMDSA-N 2-[(1r,5r,6s)-6-(aminomethyl)-6-bicyclo[3.2.0]heptanyl]acetic acid Chemical compound C1CC[C@H]2[C@@](CN)(CC(O)=O)C[C@H]21 JXSBZOVCVUSLIO-NQMVMOMDSA-N 0.000 description 1
QKBKGNDTLQFSEU-UHFFFAOYSA-N 2-bromo-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Br)=C QKBKGNDTLQFSEU-UHFFFAOYSA-N 0.000 description 1
125000005999 2-bromoethyl group Chemical group 0.000 description 1
ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 1
JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 description 1
MIVRMHJOEYRXQB-UHFFFAOYSA-N 2-diazonio-1-methoxyethenolate Chemical compound COC(=O)C=[N+]=[N-] MIVRMHJOEYRXQB-UHFFFAOYSA-N 0.000 description 1
SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 description 1
ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical group CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
ALWVPFIPTLPTEV-UHFFFAOYSA-N 2h-pyrazolo[4,3-d]pyrimidine-3,5-dione Chemical compound C1=NC(=O)N=C2C(=O)NN=C21 ALWVPFIPTLPTEV-UHFFFAOYSA-N 0.000 description 1
ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
MLYMYGBNGIZLMB-UHFFFAOYSA-N 3,5-dichloro-2h-pyrazolo[4,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2C(Cl)=NNC2=C1 MLYMYGBNGIZLMB-UHFFFAOYSA-N 0.000 description 1
MOEZPHHJIZLEKX-UHFFFAOYSA-N 3-[[1-(aminomethyl)cyclohexyl]methyl]-2h-1,2,4-oxadiazol-5-one Chemical compound N=1OC(=O)NC=1CC1(CN)CCCCC1 MOEZPHHJIZLEKX-UHFFFAOYSA-N 0.000 description 1
HISMRKYDXNXRDR-OAHLLOKOSA-N 3-ethyl-5-[(3r)-3-ethylpiperazin-1-yl]-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN[C@H](CC)CN1C1=NC(NC=2N=CC=CC=2)=C(N(CCOCC(F)(F)F)N=C2CC)C2=N1 HISMRKYDXNXRDR-OAHLLOKOSA-N 0.000 description 1
HISMRKYDXNXRDR-HNNXBMFYSA-N 3-ethyl-5-[(3s)-3-ethylpiperazin-1-yl]-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN[C@@H](CC)CN1C1=NC(NC=2N=CC=CC=2)=C(N(CCOCC(F)(F)F)N=C2CC)C2=N1 HISMRKYDXNXRDR-HNNXBMFYSA-N 0.000 description 1
ZAZKHJACWGNDDI-HNNXBMFYSA-N 3-ethyl-5-[(3s)-3-methylpiperazin-1-yl]-n-(5-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@H](C)NCC2)N=C2C(CC)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 ZAZKHJACWGNDDI-HNNXBMFYSA-N 0.000 description 1
NCGICGYLBXGBGN-UHFFFAOYSA-N 3-morpholin-4-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine;hydrochloride Chemical compound Cl.[N-]1OC(=N)C=[N+]1N1CCOCC1 NCGICGYLBXGBGN-UHFFFAOYSA-N 0.000 description 1
DAJWLVKYZBEQFI-UHFFFAOYSA-N 4-(trifluoromethyl)-1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C1=NNC=C1C(F)(F)F DAJWLVKYZBEQFI-UHFFFAOYSA-N 0.000 description 1
YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
JVXDFTZWKFHULK-UHFFFAOYSA-N 4-amino-1h-pyrazole-5-carboxamide Chemical compound NC(=O)C=1NN=CC=1N JVXDFTZWKFHULK-UHFFFAOYSA-N 0.000 description 1
HJLRZHHJZROOKA-UHFFFAOYSA-N 4-amino-2-[2-(2,2,2-trifluoroethoxy)ethyl]-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound NC(=O)C1=C(N)C(C(F)(F)F)=NN1CCOCC(F)(F)F HJLRZHHJZROOKA-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 1
XORHNJQEWQGXCN-UHFFFAOYSA-N 4-nitro-1h-pyrazole Chemical compound [O-][N+](=O)C=1C=NNC=1 XORHNJQEWQGXCN-UHFFFAOYSA-N 0.000 description 1
SVHOGXCJBBYKOT-UHFFFAOYSA-N 4-nitro-1h-pyrazole-5-carboxamide Chemical compound NC(=O)C=1NN=CC=1[N+]([O-])=O SVHOGXCJBBYKOT-UHFFFAOYSA-N 0.000 description 1
OEOQYHINYSQQOO-UHFFFAOYSA-N 4-nitro-5-propyl-1h-pyrazole-3-carboxamide Chemical compound CCCC1=NNC(C(N)=O)=C1[N+]([O-])=O OEOQYHINYSQQOO-UHFFFAOYSA-N 0.000 description 1
NLXIGOBFPAGAPS-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-(5-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCCC2)=NC=1NC1=CC=C(C)C=N1 NLXIGOBFPAGAPS-UHFFFAOYSA-N 0.000 description 1
QYCXAPDCEQJJIX-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-1-(2-ethoxyethyl)-3-ethyl-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2CCNCCC2)=NC=1NC1=CC=NC=N1 QYCXAPDCEQJJIX-UHFFFAOYSA-N 0.000 description 1
LKCCQHAFYYVKIY-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-1-(2-ethoxyethyl)-3-methyl-n-(5-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(C)C2=NC(N2CCNCCC2)=NC=1NC1=CC=C(C)C=N1 LKCCQHAFYYVKIY-UHFFFAOYSA-N 0.000 description 1
CKCVBDBYPHAQPR-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-3-methyl-n-(5-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCCC2)N=C2C(C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 CKCVBDBYPHAQPR-UHFFFAOYSA-N 0.000 description 1
MSSVIODBYADJTR-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-3-propan-2-yl-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2CCNCCC2)N=C2C(C(C)C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 MSSVIODBYADJTR-UHFFFAOYSA-N 0.000 description 1
OSPYFIOHMBSNMJ-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-n-(5-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=CC(C)=CC=C1NC1=NC(N2CCNCCC2)=NC2=C1N(CCOCC(F)(F)F)N=C2 OSPYFIOHMBSNMJ-UHFFFAOYSA-N 0.000 description 1
OKBMPJDMIGKHCZ-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC(F)(F)F)N=CC2=NC(N2CCNCCC2)=NC=1NC1=CC=NC=N1 OKBMPJDMIGKHCZ-UHFFFAOYSA-N 0.000 description 1
CIVNBJPTGRMGRS-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrazole-3-carboxylic acid Chemical compound OC(=O)C=1C=C(C(F)(F)F)NN=1 CIVNBJPTGRMGRS-UHFFFAOYSA-N 0.000 description 1
UBICCUUHQDIACN-CYBMUJFWSA-N 5-[(3r)-3-methylpiperazin-1-yl]-n-pyridin-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN[C@H](C)CN1C1=NC(NC=2N=CC=CC=2)=C(N(CCOCC(F)(F)F)N=C2)C2=N1 UBICCUUHQDIACN-CYBMUJFWSA-N 0.000 description 1
RYFUWXFHCVDVBX-IAGOWNOFSA-N 5-[(3r,5r)-3,5-dimethylpiperazin-1-yl]-1-(2-ethoxyethyl)-3-ethyl-n-(5-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(N2C[C@@H](C)N[C@H](C)C2)=NC=1NC1=CC=C(C)C=N1 RYFUWXFHCVDVBX-IAGOWNOFSA-N 0.000 description 1
IWBORWUNXZWLEO-IAGOWNOFSA-N 5-[(3r,5r)-3,5-dimethylpiperazin-1-yl]-n-(5-methylpyridin-2-yl)-3-propan-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@@H](C)N[C@H](C)C2)N=C2C(C(C)C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 IWBORWUNXZWLEO-IAGOWNOFSA-N 0.000 description 1
NHRGHEIBOMPFLE-OKILXGFUSA-N 5-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-1-(2-ethoxyethyl)-n-pyrimidin-4-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=CC2=NC(N2C[C@@H](C)N[C@@H](C)C2)=NC=1NC1=CC=NC=N1 NHRGHEIBOMPFLE-OKILXGFUSA-N 0.000 description 1
QONCXHYWVZYIMJ-AWEZNQCLSA-N 5-[(3s)-3-methylpiperazin-1-yl]-n-(5-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN[C@@H](C)CN1C1=NC(NC=2N=CC(C)=CC=2)=C(N(CCOCC(F)(F)F)N=C2)C2=N1 QONCXHYWVZYIMJ-AWEZNQCLSA-N 0.000 description 1
IWOHERCDINQBDN-INIZCTEOSA-N 5-[(3s)-3-methylpiperazin-1-yl]-n-(5-methylpyridin-2-yl)-3-propan-2-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound N1=C(N2C[C@H](C)NCC2)N=C2C(C(C)C)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=C(C)C=N1 IWOHERCDINQBDN-INIZCTEOSA-N 0.000 description 1
XLFFUYKFPUVBKL-IYBDPMFKSA-N 5-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-1-(2-ethoxyethyl)-n-(5-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=CC2=NC(N2C[C@@H](C)N[C@@H](C)C2)=NC=1NC1=CC=C(C)C=N1 XLFFUYKFPUVBKL-IYBDPMFKSA-N 0.000 description 1
UPJSCDQTPUWAEE-BETUJISGSA-N 5-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-3-methyl-n-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=NC(NC=2N=CN=CC=2)=C(N(CCOCC(F)(F)F)N=C2C)C2=N1 UPJSCDQTPUWAEE-BETUJISGSA-N 0.000 description 1
OJNYGCVZWIXOMW-UHFFFAOYSA-N 5-chloro-1-(2-ethoxyethyl)-3-(ethoxymethyl)-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(Cl)=NC=1NC1=CC(C)=CC=N1 OJNYGCVZWIXOMW-UHFFFAOYSA-N 0.000 description 1
GPYRHGJDBPLURY-UHFFFAOYSA-N 5-chloro-1-(2-ethoxyethyl)-3-(ethoxymethyl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COCC)C2=NC(Cl)=NC=1NC1=CC=CC=N1 GPYRHGJDBPLURY-UHFFFAOYSA-N 0.000 description 1
UFZMCZZBCQJSOQ-UHFFFAOYSA-N 5-chloro-1-(2-ethoxyethyl)-3-(methoxymethyl)-n-(4-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(COC)C2=NC(Cl)=NC=1NC1=CC(C)=CC=N1 UFZMCZZBCQJSOQ-UHFFFAOYSA-N 0.000 description 1
WKVCKAMSHCHYPB-UHFFFAOYSA-N 5-chloro-1-(2-ethoxyethyl)-3-ethyl-n-(6-methylpyridin-2-yl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCC)N=C(CC)C2=NC(Cl)=NC=1NC1=CC=CC(C)=N1 WKVCKAMSHCHYPB-UHFFFAOYSA-N 0.000 description 1
XGRVUJNXJPGEPW-UHFFFAOYSA-N 5-chloro-3-(ethoxymethyl)-1-(2-propoxyethyl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COCC)C2=NC(Cl)=NC=1NC1=CC=CC=N1 XGRVUJNXJPGEPW-UHFFFAOYSA-N 0.000 description 1
UKMFJXVAKZGDBR-UHFFFAOYSA-N 5-chloro-3-(methoxymethyl)-1-(2-propoxyethyl)-n-pyridin-2-ylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C=12N(CCOCCC)N=C(COC)C2=NC(Cl)=NC=1NC1=CC=CC=N1 UKMFJXVAKZGDBR-UHFFFAOYSA-N 0.000 description 1
VGJQCOQUYZFRAO-UHFFFAOYSA-N 5-chloro-n-(4-methylpyridin-2-yl)-1-[2-(2,2,2-trifluoroethoxy)ethyl]-3-(2,2,2-trifluoroethoxymethyl)pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound CC1=CC=NC(NC=2C=3N(CCOCC(F)(F)F)N=C(COCC(F)(F)F)C=3N=C(Cl)N=2)=C1 VGJQCOQUYZFRAO-UHFFFAOYSA-N 0.000 description 1
MZVQCTATYLWIQA-UHFFFAOYSA-N 5-methyl-4-nitro-3-(trifluoromethyl)-1h-pyrazole Chemical compound CC=1NN=C(C(F)(F)F)C=1[N+]([O-])=O MZVQCTATYLWIQA-UHFFFAOYSA-N 0.000 description 1
MZRUFMBFIKGOAL-UHFFFAOYSA-N 5-nitro-1h-pyrazole Chemical compound [O-][N+](=O)C1=CC=NN1 MZRUFMBFIKGOAL-UHFFFAOYSA-N 0.000 description 1
RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 1
UUVDJIWRSIJEBS-UHFFFAOYSA-N 6-methoxypyridin-3-amine Chemical group COC1=CC=C(N)C=N1 UUVDJIWRSIJEBS-UHFFFAOYSA-N 0.000 description 1
USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 description 1
239000005541 ACE inhibitor Substances 0.000 description 1
208000004998 Abdominal Pain Diseases 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
201000006641 Acquired generalized lipodystrophy Diseases 0.000 description 1
206010000599 Acromegaly Diseases 0.000 description 1
208000009304 Acute Kidney Injury Diseases 0.000 description 1
208000026872 Addison Disease Diseases 0.000 description 1
208000007848 Alcoholism Diseases 0.000 description 1
201000004384 Alopecia Diseases 0.000 description 1
229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 1
229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
208000031091 Amnestic disease Diseases 0.000 description 1
206010002153 Anal fissure Diseases 0.000 description 1
102000008873 Angiotensin II receptor Human genes 0.000 description 1
108050000824 Angiotensin II receptor Proteins 0.000 description 1
206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
208000016583 Anus disease Diseases 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
208000036487 Arthropathies Diseases 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
IUVMAUQEZFTTFB-YUMQZZPRSA-N Atagabalin Chemical compound C[C@H]1CC(CN)(CC(O)=O)C[C@@H]1C IUVMAUQEZFTTFB-YUMQZZPRSA-N 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
206010003658 Atrial Fibrillation Diseases 0.000 description 1
208000000412 Avitaminosis Diseases 0.000 description 1
208000037157 Azotemia Diseases 0.000 description 1
XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 1
229940123208 Biguanide Drugs 0.000 description 1
206010071445 Bladder outlet obstruction Diseases 0.000 description 1
206010006002 Bone pain Diseases 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
206010068065 Burning mouth syndrome Diseases 0.000 description 1
TWZGTRJIOQHMDR-OAHLLOKOSA-N C(C)(C)C1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@@H](CC2)C(=O)O)CCOCC(F)(F)F Chemical compound C(C)(C)C1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@@H](CC2)C(=O)O)CCOCC(F)(F)F TWZGTRJIOQHMDR-OAHLLOKOSA-N 0.000 description 1
NXRNMEOTKIDWKQ-ZDUSSCGKSA-N C(C)(C)C1=NN(C2=C1N=C(N=C2NC2=NC=NC=C2)N2C[C@H](CC2)C(=O)O)CCOCC(F)(F)F Chemical compound C(C)(C)C1=NN(C2=C1N=C(N=C2NC2=NC=NC=C2)N2C[C@H](CC2)C(=O)O)CCOCC(F)(F)F NXRNMEOTKIDWKQ-ZDUSSCGKSA-N 0.000 description 1
ZJCGPLQWKWESNW-CQSZACIVSA-N C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@@H](CC2)C(=O)O)CCOCC(F)(F)F Chemical compound C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@@H](CC2)C(=O)O)CCOCC(F)(F)F ZJCGPLQWKWESNW-CQSZACIVSA-N 0.000 description 1
VZHMOUHUHWLMPH-OAHLLOKOSA-N C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@@H](CCC2)C(=O)O)CCOCC(F)(F)F Chemical compound C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@@H](CCC2)C(=O)O)CCOCC(F)(F)F VZHMOUHUHWLMPH-OAHLLOKOSA-N 0.000 description 1
ZJCGPLQWKWESNW-AWEZNQCLSA-N C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@H](CC2)C(=O)O)CCOCC(F)(F)F Chemical compound C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@H](CC2)C(=O)O)CCOCC(F)(F)F ZJCGPLQWKWESNW-AWEZNQCLSA-N 0.000 description 1
ANSZTJANDGMZEF-LBPRGKRZSA-N C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=NC=C2)N2C[C@H](CC2)C(=O)O)CCOCC(F)(F)F Chemical compound C(C)C1=NN(C2=C1N=C(N=C2NC2=NC=NC=C2)N2C[C@H](CC2)C(=O)O)CCOCC(F)(F)F ANSZTJANDGMZEF-LBPRGKRZSA-N 0.000 description 1
ARDAARCLSUALQA-SFHVURJKSA-N C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=C(C=C2)C)N2C[C@@H](NCC2)CC)C(C)C Chemical compound C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=C(C=C2)C)N2C[C@@H](NCC2)CC)C(C)C ARDAARCLSUALQA-SFHVURJKSA-N 0.000 description 1
AHRJKQBDCUOQBW-HNNXBMFYSA-N C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=NC=C2)N2C[C@@H](NCC2)C)C(C)C Chemical compound C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=NC=C2)N2C[C@@H](NCC2)C)C(C)C AHRJKQBDCUOQBW-HNNXBMFYSA-N 0.000 description 1
RCASRDJUHSUVHM-AWEZNQCLSA-N C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=NC=C2)N2C[C@H](CC2)C(=O)O)C(C)C Chemical compound C(C)OCCN1N=C(C=2N=C(N=C(C21)NC2=NC=NC=C2)N2C[C@H](CC2)C(=O)O)C(C)C RCASRDJUHSUVHM-AWEZNQCLSA-N 0.000 description 1
INARZYFHPLLZQN-CQSZACIVSA-N C(C)OCCN1N=CC=2N=C(N=C(C21)NC2=NC=CC=C2)N2C[C@@H](CCC2)C(=O)O Chemical compound C(C)OCCN1N=CC=2N=C(N=C(C21)NC2=NC=CC=C2)N2C[C@@H](CCC2)C(=O)O INARZYFHPLLZQN-CQSZACIVSA-N 0.000 description 1
XPIFNKHEWOUNCF-LBPRGKRZSA-N C(C)OCCN1N=CC=2N=C(N=C(C21)NC2=NC=NC=C2)N2C[C@H](CC2)C(=O)O Chemical compound C(C)OCCN1N=CC=2N=C(N=C(C21)NC2=NC=NC=C2)N2C[C@H](CC2)C(=O)O XPIFNKHEWOUNCF-LBPRGKRZSA-N 0.000 description 1
239000002083 C09CA01 - Losartan Substances 0.000 description 1
239000002080 C09CA02 - Eprosartan Substances 0.000 description 1
239000004072 C09CA03 - Valsartan Substances 0.000 description 1
239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
239000002081 C09CA05 - Tasosartan Substances 0.000 description 1
239000002053 C09CA06 - Candesartan Substances 0.000 description 1
239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
239000002051 C09CA08 - Olmesartan medoxomil Substances 0.000 description 1
125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
125000004649 C2-C8 alkynyl group Chemical group 0.000 description 1
WOSKVLDLPSAZDR-AWEZNQCLSA-N CC1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@H](CC2)C(=O)O)CCOCC(F)(F)F Chemical compound CC1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@H](CC2)C(=O)O)CCOCC(F)(F)F WOSKVLDLPSAZDR-AWEZNQCLSA-N 0.000 description 1
QYJAJLZINMKWCS-CQSZACIVSA-N CC1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@H](NCC2)C)CCOCC(F)(F)F Chemical compound CC1=NN(C2=C1N=C(N=C2NC2=NC=C(C=C2)C)N2C[C@H](NCC2)C)CCOCC(F)(F)F QYJAJLZINMKWCS-CQSZACIVSA-N 0.000 description 1
TYWGMLORNCVYBR-CYBMUJFWSA-N CC=1C=CC(=NC1)NC=1C2=C(N=C(N1)N1C[C@@H](CC1)C(=O)O)C=NN2CCOCC(F)(F)F Chemical compound CC=1C=CC(=NC1)NC=1C2=C(N=C(N1)N1C[C@@H](CC1)C(=O)O)C=NN2CCOCC(F)(F)F TYWGMLORNCVYBR-CYBMUJFWSA-N 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
SLBPXAJXWFRXDT-FIWHBWSRSA-N CCOCCn1nc(C(C)O)c2nc(nc(Nc3ccncn3)c12)N1CCN([C@H](C)C1)C(=O)OCc1ccccc1 Chemical compound CCOCCn1nc(C(C)O)c2nc(nc(Nc3ccncn3)c12)N1CCN([C@H](C)C1)C(=O)OCc1ccccc1 SLBPXAJXWFRXDT-FIWHBWSRSA-N 0.000 description 1
HYCODCGSNULBCS-GASCZTMLSA-N C[C@@H]1CN(C[C@@H](N1)C)C=1N=C(C2=C(N1)C(=NN2CCOCC(F)(F)F)C)NC2=NC=C(C=C2)C Chemical compound C[C@@H]1CN(C[C@@H](N1)C)C=1N=C(C2=C(N1)C(=NN2CCOCC(F)(F)F)C)NC2=NC=C(C=C2)C HYCODCGSNULBCS-GASCZTMLSA-N 0.000 description 1
WEPVZQBJWFAWOK-GASCZTMLSA-N C[C@@H]1CN(C[C@@H](N1)C)C=1N=C(C2=C(N1)C=NN2CCOCC(F)(F)F)NC2=NC=C(C=C2)C Chemical compound C[C@@H]1CN(C[C@@H](N1)C)C=1N=C(C2=C(N1)C=NN2CCOCC(F)(F)F)NC2=NC=C(C=C2)C WEPVZQBJWFAWOK-GASCZTMLSA-N 0.000 description 1
206010006895 Cachexia Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229940127291 Calcium channel antagonist Drugs 0.000 description 1
241000282421 Canidae Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000283707 Capra Species 0.000 description 1
OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
206010007559 Cardiac failure congestive Diseases 0.000 description 1
208000031229 Cardiomyopathies Diseases 0.000 description 1
108010078791 Carrier Proteins Proteins 0.000 description 1
102000014914 Carrier Proteins Human genes 0.000 description 1
102100033668 Cartilage matrix protein Human genes 0.000 description 1
206010007749 Cataract diabetic Diseases 0.000 description 1
206010064012 Central pain syndrome Diseases 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
206010008190 Cerebrovascular accident Diseases 0.000 description 1
241000282994 Cervidae Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
208000000094 Chronic Pain Diseases 0.000 description 1
238000003512 Claisen condensation reaction Methods 0.000 description 1
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
208000006561 Cluster Headache Diseases 0.000 description 1
229920002905 Colesevelam Polymers 0.000 description 1
229920002911 Colestipol Polymers 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
102000008186 Collagen Human genes 0.000 description 1
108010035532 Collagen Proteins 0.000 description 1
206010053547 Congenital generalised lipodystrophy Diseases 0.000 description 1
208000016998 Conn syndrome Diseases 0.000 description 1
102000034534 Cotransporters Human genes 0.000 description 1
108020003264 Cotransporters Proteins 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
229920002785 Croscarmellose sodium Polymers 0.000 description 1
208000014311 Cushing syndrome Diseases 0.000 description 1
201000003883 Cystic fibrosis Diseases 0.000 description 1
DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
208000002249 Diabetes Complications Diseases 0.000 description 1
208000032780 Diabetic arthropathy Diseases 0.000 description 1
206010012655 Diabetic complications Diseases 0.000 description 1
206010012665 Diabetic gangrene Diseases 0.000 description 1
206010012689 Diabetic retinopathy Diseases 0.000 description 1
LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 1
208000034669 Dunnigan type familial partial lipodystrophy Diseases 0.000 description 1
206010013924 Dyskinesia oesophageal Diseases 0.000 description 1
206010013935 Dysmenorrhoea Diseases 0.000 description 1
108010061435 Enalapril Proteins 0.000 description 1
206010048554 Endothelial dysfunction Diseases 0.000 description 1
241000792859 Enema Species 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000283086 Equidae Species 0.000 description 1
208000007530 Essential hypertension Diseases 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
238000004252 FT/ICR mass spectrometry Methods 0.000 description 1
GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
208000003929 Familial Partial Lipodystrophy Diseases 0.000 description 1
208000020970 Familial partial lipodystrophy, Dunnigan type Diseases 0.000 description 1
208000021663 Female sexual arousal disease Diseases 0.000 description 1
208000001640 Fibromyalgia Diseases 0.000 description 1
208000009531 Fissure in Ano Diseases 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 1
208000011688 Generalised anxiety disease Diseases 0.000 description 1
208000022461 Glomerular disease Diseases 0.000 description 1
206010018404 Glucagonoma Diseases 0.000 description 1
FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 1
208000002705 Glucose Intolerance Diseases 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
208000003807 Graves Disease Diseases 0.000 description 1
208000015023 Graves' disease Diseases 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
WDZVGELJXXEGPV-YIXHJXPBSA-N Guanabenz Chemical compound NC(N)=N\N=C\C1=C(Cl)C=CC=C1Cl WDZVGELJXXEGPV-YIXHJXPBSA-N 0.000 description 1
INJOMKTZOLKMBF-UHFFFAOYSA-N Guanfacine Chemical compound NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl INJOMKTZOLKMBF-UHFFFAOYSA-N 0.000 description 1
108010078321 Guanylate Cyclase Proteins 0.000 description 1
102000014469 Guanylate cyclase Human genes 0.000 description 1
229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
208000030836 Hashimoto thyroiditis Diseases 0.000 description 1
206010019196 Head injury Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
101001018382 Homo sapiens Cartilage matrix protein Proteins 0.000 description 1
102000013266 Human Regular Insulin Human genes 0.000 description 1
108010090613 Human Regular Insulin Proteins 0.000 description 1
208000023105 Huntington disease Diseases 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
208000031226 Hyperlipidaemia Diseases 0.000 description 1
206010021135 Hypovitaminosis Diseases 0.000 description 1
206010021639 Incontinence Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
102000003746 Insulin Receptor Human genes 0.000 description 1
108010001127 Insulin Receptor Proteins 0.000 description 1
108010044467 Isoenzymes Proteins 0.000 description 1
208000012659 Joint disease Diseases 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 1
208000035369 Leprechaunism Diseases 0.000 description 1
206010024419 Libido decreased Diseases 0.000 description 1
108010007859 Lisinopril Proteins 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
208000000060 Migraine with aura Diseases 0.000 description 1
102000003979 Mineralocorticoid Receptors Human genes 0.000 description 1
108090000375 Mineralocorticoid Receptors Proteins 0.000 description 1
208000020128 Mitral stenosis Diseases 0.000 description 1
UWWDHYUMIORJTA-HSQYWUDLSA-N Moexipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 UWWDHYUMIORJTA-HSQYWUDLSA-N 0.000 description 1
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000023178 Musculoskeletal disease Diseases 0.000 description 1
208000000112 Myalgia Diseases 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
108010029138 N-nitratopivaloyl-S-(N'-acetylalanyl)-cysteine ethyl ester Proteins 0.000 description 1
208000001738 Nervous System Trauma Diseases 0.000 description 1
SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
239000000006 Nitroglycerin Substances 0.000 description 1
208000001294 Nociceptive Pain Diseases 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
239000005480 Olmesartan Substances 0.000 description 1
UQGKUQLKSCSZGY-UHFFFAOYSA-N Olmesartan medoxomil Chemical compound C=1C=C(C=2C(=CC=CC=2)C2=NNN=N2)C=CC=1CN1C(CCC)=NC(C(C)(C)O)=C1C(=O)OCC=1OC(=O)OC=1C UQGKUQLKSCSZGY-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
102000004316 Oxidoreductases Human genes 0.000 description 1
108090000854 Oxidoreductases Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241000282579 Pan Species 0.000 description 1
206010033645 Pancreatitis Diseases 0.000 description 1
206010033647 Pancreatitis acute Diseases 0.000 description 1
208000027089 Parkinsonian disease Diseases 0.000 description 1
206010034010 Parkinsonism Diseases 0.000 description 1
241001494479 Pecora Species 0.000 description 1
208000000450 Pelvic Pain Diseases 0.000 description 1
206010034576 Peripheral ischaemia Diseases 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
208000004983 Phantom Limb Diseases 0.000 description 1
206010056238 Phantom pain Diseases 0.000 description 1
QZVCTJOXCFMACW-UHFFFAOYSA-N Phenoxybenzamine Chemical compound C=1C=CC=CC=1CN(CCCl)C(C)COC1=CC=CC=C1 QZVCTJOXCFMACW-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
XRKXJJYSKUIIEN-LLVKDONJSA-N Pivopril Chemical compound CC(C)(C)C(=O)SC[C@@H](C)C(=O)N(CC(O)=O)C1CCCC1 XRKXJJYSKUIIEN-LLVKDONJSA-N 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
108010005991 Pork Regular Insulin Proteins 0.000 description 1
206010065016 Post-traumatic pain Diseases 0.000 description 1
201000009916 Postpartum depression Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
208000006399 Premature Obstetric Labor Diseases 0.000 description 1
206010036600 Premature labour Diseases 0.000 description 1
241000288906 Primates Species 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
208000006262 Psychological Sexual Dysfunctions Diseases 0.000 description 1
201000001177 Pyomyositis Diseases 0.000 description 1
208000016140 Rabson-Mendenhall syndrome Diseases 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
208000003782 Raynaud disease Diseases 0.000 description 1
206010038419 Renal colic Diseases 0.000 description 1
208000033626 Renal failure acute Diseases 0.000 description 1
201000003099 Renovascular Hypertension Diseases 0.000 description 1
206010038687 Respiratory distress Diseases 0.000 description 1
208000017442 Retinal disease Diseases 0.000 description 1
RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
208000034189 Sclerosis Diseases 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N Sec-butyl alcohol Natural products CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
201000004239 Secondary hypertension Diseases 0.000 description 1
229910018557 Si O Inorganic materials 0.000 description 1
206010040893 Skin necrosis Diseases 0.000 description 1
239000004115 Sodium Silicate Substances 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
102000007637 Soluble Guanylyl Cyclase Human genes 0.000 description 1
108010007205 Soluble Guanylyl Cyclase Proteins 0.000 description 1
208000027520 Somatoform disease Diseases 0.000 description 1
206010041329 Somatostatinoma Diseases 0.000 description 1
239000004147 Sorbitan trioleate Substances 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
201000002661 Spondylitis Diseases 0.000 description 1
208000010040 Sprains and Strains Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
241000282887 Suidae Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229940100389 Sulfonylurea Drugs 0.000 description 1
238000006859 Swern oxidation reaction Methods 0.000 description 1
206010042957 Systolic hypertension Diseases 0.000 description 1
206010043118 Tardive Dyskinesia Diseases 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
208000008548 Tension-Type Headache Diseases 0.000 description 1
229940123464 Thiazolidinedione Drugs 0.000 description 1
208000001435 Thromboembolism Diseases 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 description 1
FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
208000003800 Urinary Bladder Neck Obstruction Diseases 0.000 description 1
241000282458 Ursus sp. Species 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
201000004810 Vascular dementia Diseases 0.000 description 1
206010047095 Vascular pain Diseases 0.000 description 1
206010047115 Vasculitis Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
TUQDMVHGTMRAAB-UHFFFAOYSA-N [5-chloro-1-(2-ethoxyethyl)-7-(pyridin-2-ylamino)pyrazolo[4,3-d]pyrimidin-3-yl]methanol Chemical compound C=12N(CCOCC)N=C(CO)C2=NC(Cl)=NC=1NC1=CC=CC=N1 TUQDMVHGTMRAAB-UHFFFAOYSA-N 0.000 description 1
FZBJNTRGZHJXRQ-UHFFFAOYSA-N [5-chloro-1-(2-ethoxyethyl)-7-(pyrimidin-2-ylamino)pyrazolo[4,3-d]pyrimidin-3-yl]methanol Chemical compound C=12N(CCOCC)N=C(CO)C2=NC(Cl)=NC=1NC1=NC=CC=N1 FZBJNTRGZHJXRQ-UHFFFAOYSA-N 0.000 description 1
ICRXQXXDFLCZPJ-UHFFFAOYSA-N [5-chloro-1-(2-ethoxyethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-3-yl]methanol Chemical compound C=12N(CCOCC)N=C(CO)C2=NC(Cl)=NC=1NC1=CC(C)=CC=N1 ICRXQXXDFLCZPJ-UHFFFAOYSA-N 0.000 description 1
GMLHTEOLAKERQT-UHFFFAOYSA-N [5-chloro-7-(pyridin-2-ylamino)-1-[2-(2,2,2-trifluoroethoxy)ethyl]pyrazolo[4,3-d]pyrimidin-3-yl]methanol Chemical compound N1=C(Cl)N=C2C(CO)=NN(CCOCC(F)(F)F)C2=C1NC1=CC=CC=N1 GMLHTEOLAKERQT-UHFFFAOYSA-N 0.000 description 1
GTSIREOHSCZYGV-UHFFFAOYSA-N [F].CCCC[N+](CCCC)(CCCC)CCCC Chemical compound [F].CCCC[N+](CCCC)(CCCC)CCCC GTSIREOHSCZYGV-UHFFFAOYSA-N 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
229960002632 acarbose Drugs 0.000 description 1
XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
201000011040 acute kidney failure Diseases 0.000 description 1
208000005298 acute pain Diseases 0.000 description 1
201000003229 acute pancreatitis Diseases 0.000 description 1
208000012998 acute renal failure Diseases 0.000 description 1
229940092980 adalat Drugs 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000000674 adrenergic antagonist Substances 0.000 description 1
125000006241 alcohol protecting group Chemical group 0.000 description 1
229960004601 aliskiren Drugs 0.000 description 1
125000004450 alkenylene group Chemical group 0.000 description 1
125000005227 alkyl sulfonate group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
239000002160 alpha blocker Substances 0.000 description 1
239000003888 alpha glucosidase inhibitor Substances 0.000 description 1
229940124308 alpha-adrenoreceptor antagonist Drugs 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 1
229960002576 amiloride Drugs 0.000 description 1
HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 1
229960000528 amlodipine Drugs 0.000 description 1
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
230000001466 anti-adreneric effect Effects 0.000 description 1
230000000702 anti-platelet effect Effects 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
229940009098 aspartate Drugs 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
229960002274 atenolol Drugs 0.000 description 1
230000003143 atherosclerotic effect Effects 0.000 description 1
229960005370 atorvastatin Drugs 0.000 description 1
125000002785 azepinyl group Chemical group 0.000 description 1
229960004530 benazepril Drugs 0.000 description 1
230000008901 benefit Effects 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000003310 benzodiazepinyl group Chemical group N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
ZRLBATAGNCPZIC-XMMPIXPASA-N benzyl (2r)-4-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-(2-ethoxyethyl)-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]-2-methylpiperazine-1-carboxylate Chemical group C=12N(CCOCC)N=C(CO[Si](C)(C)C(C)(C)C)C2=NC(N2C[C@@H](C)N(CC2)C(=O)OCC=2C=CC=CC=2)=NC=1NC1=CC=NC=N1 ZRLBATAGNCPZIC-XMMPIXPASA-N 0.000 description 1
KKBIUAUSZKGNOA-HNAYVOBHSA-N benzyl (2s)-2-[[(2s)-2-(acetylsulfanylmethyl)-3-(1,3-benzodioxol-5-yl)propanoyl]amino]propanoate Chemical compound O=C([C@@H](NC(=O)[C@@H](CSC(C)=O)CC=1C=C2OCOC2=CC=1)C)OCC1=CC=CC=C1 KKBIUAUSZKGNOA-HNAYVOBHSA-N 0.000 description 1
ABNXTZQEPLZSSM-UHFFFAOYSA-N benzyl 4-[1,3-bis(2-ethoxyethyl)-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical compound N1=C(N2CCN(CC2)C(=O)OCC=2C=CC=CC=2)N=C2C(CCOCC)=NN(CCOCC)C2=C1NC1=CC=NC=N1 ABNXTZQEPLZSSM-UHFFFAOYSA-N 0.000 description 1
JADDYCLHIRNFSF-UHFFFAOYSA-N benzyl 4-[1-(2-ethoxyethyl)-3-(2-oxoethyl)-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical compound C=12N(CCOCC)N=C(CC=O)C2=NC(N2CCN(CC2)C(=O)OCC=2C=CC=CC=2)=NC=1NC1=CC=NC=N1 JADDYCLHIRNFSF-UHFFFAOYSA-N 0.000 description 1
IEKIGZGINMHHGS-UHFFFAOYSA-N benzyl 4-[1-(2-ethoxyethyl)-3-formyl-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical compound C=12N(CCOCC)N=C(C=O)C2=NC(N2CCN(CC2)C(=O)OCC=2C=CC=CC=2)=NC=1NC1=CC=NC=N1 IEKIGZGINMHHGS-UHFFFAOYSA-N 0.000 description 1
RVMDQCYPPLJXTK-UHFFFAOYSA-N benzyl 4-[3-(2-chloroethyl)-1-(2-ethoxyethyl)-7-(pyrimidin-4-ylamino)pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical group C=12N(CCOCC)N=C(CCCl)C2=NC(N2CCN(CC2)C(=O)OCC=2C=CC=CC=2)=NC=1NC1=CC=NC=N1 RVMDQCYPPLJXTK-UHFFFAOYSA-N 0.000 description 1
CTOUWUYDDUSBQE-UHFFFAOYSA-N benzyl piperazine-1-carboxylate Chemical group C1CNCCN1C(=O)OCC1=CC=CC=C1 CTOUWUYDDUSBQE-UHFFFAOYSA-N 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
UIEATEWHFDRYRU-UHFFFAOYSA-N bepridil Chemical compound C1CCCN1C(COCC(C)C)CN(C=1C=CC=CC=1)CC1=CC=CC=C1 UIEATEWHFDRYRU-UHFFFAOYSA-N 0.000 description 1
229960003665 bepridil Drugs 0.000 description 1
229960004324 betaxolol Drugs 0.000 description 1
NWIUTZDMDHAVTP-UHFFFAOYSA-N betaxolol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1CCOCC1CC1 NWIUTZDMDHAVTP-UHFFFAOYSA-N 0.000 description 1
125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
150000004283 biguanides Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
ZICDXDPVQDNYTC-UHFFFAOYSA-N butan-2-ol Chemical compound CCC([CH2+])O ZICDXDPVQDNYTC-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000000480 calcium channel blocker Substances 0.000 description 1
XAAHAAMILDNBPS-UHFFFAOYSA-L calcium hydrogenphosphate dihydrate Chemical compound O.O.[Ca+2].OP([O-])([O-])=O XAAHAAMILDNBPS-UHFFFAOYSA-L 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
229960000932 candesartan Drugs 0.000 description 1
SGZAIDDFHDDFJU-UHFFFAOYSA-N candesartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SGZAIDDFHDDFJU-UHFFFAOYSA-N 0.000 description 1
229960000830 captopril Drugs 0.000 description 1
FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
208000003295 carpal tunnel syndrome Diseases 0.000 description 1
LWAFSWPYPHEXKX-UHFFFAOYSA-N carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 description 1
229960001222 carteolol Drugs 0.000 description 1
NPAKNKYSJIDKMW-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 description 1
229960004195 carvedilol Drugs 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
206010008118 cerebral infarction Diseases 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
235000015111 chews Nutrition 0.000 description 1
238000004296 chiral HPLC Methods 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 1
229960002155 chlorothiazide Drugs 0.000 description 1
229960001523 chlortalidone Drugs 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
208000020832 chronic kidney disease Diseases 0.000 description 1
208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 1
208000022831 chronic renal failure syndrome Diseases 0.000 description 1
HHHKFGXWKKUNCY-FHWLQOOXSA-N cilazapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 HHHKFGXWKKUNCY-FHWLQOOXSA-N 0.000 description 1
229960005025 cilazapril Drugs 0.000 description 1
229960001214 clofibrate Drugs 0.000 description 1
KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
229960002896 clonidine Drugs 0.000 description 1
208000018912 cluster headache syndrome Diseases 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229960001152 colesevelam Drugs 0.000 description 1
GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 description 1
229960002604 colestipol Drugs 0.000 description 1
229920001436 collagen Polymers 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
238000007887 coronary angioplasty Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
229960001681 croscarmellose sodium Drugs 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
239000013058 crude material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000009109 curative therapy Methods 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
201000003146 cystitis Diseases 0.000 description 1
239000002619 cytotoxin Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229960005227 delapril Drugs 0.000 description 1
WOUOLAUOZXOLJQ-MBSDFSHPSA-N delapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 WOUOLAUOZXOLJQ-MBSDFSHPSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000007933 dermal patch Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
229910052805 deuterium Inorganic materials 0.000 description 1
201000007025 diabetic cataract Diseases 0.000 description 1
230000003205 diastolic effect Effects 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 1
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
229940099364 dichlorofluoromethane Drugs 0.000 description 1
IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 1
229960005156 digoxin Drugs 0.000 description 1
LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
230000010339 dilation Effects 0.000 description 1
229960004166 diltiazem Drugs 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
229950010286 diolamine Drugs 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
125000005879 dioxolanyl group Chemical group 0.000 description 1
HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
238000007907 direct compression Methods 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
XRKMNJXYOFSTBE-UHFFFAOYSA-N disodium;iron(4+);nitroxyl anion;pentacyanide;dihydrate Chemical compound O.O.[Na+].[Na+].[Fe+4].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].O=[N-] XRKMNJXYOFSTBE-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
125000005883 dithianyl group Chemical group 0.000 description 1
229940126534 drug product Drugs 0.000 description 1
229940112141 dry powder inhaler Drugs 0.000 description 1
238000010410 dusting Methods 0.000 description 1
201000006549 dyspepsia Diseases 0.000 description 1
238000004520 electroporation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
XFLQIRAKKLNXRQ-UUWRZZSWSA-N elobixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)NCC(O)=O)C=3C=CC=CC=3)C=C2S(=O)(=O)CC(CCCC)(CCCC)CN1C1=CC=CC=C1 XFLQIRAKKLNXRQ-UUWRZZSWSA-N 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
229960000873 enalapril Drugs 0.000 description 1
GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
230000008694 endothelial dysfunction Effects 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940095399 enema Drugs 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 description 1
229960001208 eplerenone Drugs 0.000 description 1
229960004563 eprosartan Drugs 0.000 description 1
OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 description 1
AVOLMBLBETYQHX-UHFFFAOYSA-N etacrynic acid Chemical compound CCC(=C)C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl AVOLMBLBETYQHX-UHFFFAOYSA-N 0.000 description 1
229960003199 etacrynic acid Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
KCKXBNDUEKMBFJ-ZETCQYMHSA-N ethyl (2r)-2-[(2,2-dimethyl-3-nitrooxypropanoyl)amino]-3-sulfanylpropanoate Chemical compound CCOC(=O)[C@H](CS)NC(=O)C(C)(C)CO[N+]([O-])=O KCKXBNDUEKMBFJ-ZETCQYMHSA-N 0.000 description 1
UCDOJQCUOURTPS-UHFFFAOYSA-N ethyl 2-bromoprop-2-enoate Chemical compound CCOC(=O)C(Br)=C UCDOJQCUOURTPS-UHFFFAOYSA-N 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 1
FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 1
229960000815 ezetimibe Drugs 0.000 description 1
229950005203 fasidotril Drugs 0.000 description 1
229960003580 felodipine Drugs 0.000 description 1
229960002297 fenofibrate Drugs 0.000 description 1
YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
229940125753 fibrate Drugs 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
150000004673 fluoride salts Chemical class 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
229960003765 fluvastatin Drugs 0.000 description 1
229960002490 fosinopril Drugs 0.000 description 1
229940050411 fumarate Drugs 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229960003883 furosemide Drugs 0.000 description 1
229960002870 gabapentin Drugs 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229960003627 gemfibrozil Drugs 0.000 description 1
YRSVDSQRGBYVIY-GJZGRUSLSA-N gemopatrilat Chemical compound O=C1N(CC(O)=O)C(C)(C)CCC[C@@H]1NC(=O)[C@@H](S)CC1=CC=CC=C1 YRSVDSQRGBYVIY-GJZGRUSLSA-N 0.000 description 1
208000029364 generalized anxiety disease Diseases 0.000 description 1
239000011521 glass Substances 0.000 description 1
229960004580 glibenclamide Drugs 0.000 description 1
WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
229960004346 glimepiride Drugs 0.000 description 1
229960001381 glipizide Drugs 0.000 description 1
229960001731 gluceptate Drugs 0.000 description 1
KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
229940095884 glucophage Drugs 0.000 description 1
229940088991 glucotrol Drugs 0.000 description 1
229940097042 glucuronate Drugs 0.000 description 1
229960003711 glyceryl trinitrate Drugs 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
230000004116 glycogenolysis Effects 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
229940120105 glynase Drugs 0.000 description 1
230000005484 gravity Effects 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229960004553 guanabenz Drugs 0.000 description 1
229960002048 guanfacine Drugs 0.000 description 1
229940126514 guanylate cyclase activator Drugs 0.000 description 1
239000003119 guanylate cyclase activator Substances 0.000 description 1
230000010243 gut motility Effects 0.000 description 1
230000003676 hair loss Effects 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
208000014617 hemorrhoid Diseases 0.000 description 1
238000007210 heterogeneous catalysis Methods 0.000 description 1
229950000177 hibenzate Drugs 0.000 description 1
238000007172 homogeneous catalysis Methods 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
238000001794 hormone therapy Methods 0.000 description 1
229940103471 humulin Drugs 0.000 description 1
229920002674 hyaluronan Polymers 0.000 description 1
229960003160 hyaluronic acid Drugs 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
DMDGGSIALPNSEE-UHFFFAOYSA-N hydroflumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O DMDGGSIALPNSEE-UHFFFAOYSA-N 0.000 description 1
229960003313 hydroflumethiazide Drugs 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000000852 hydrogen donor Substances 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
201000001421 hyperglycemia Diseases 0.000 description 1
208000017020 hypoactive sexual desire disease Diseases 0.000 description 1
208000003532 hypothyroidism Diseases 0.000 description 1
230000002989 hypothyroidism Effects 0.000 description 1
230000008706 hypoxic vasoconstriction Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
208000009326 ileitis Diseases 0.000 description 1
JXEHXYFSIOYTAH-SFYZADRCSA-N imagabalin Chemical compound CCC[C@@H](C)C[C@H](N)CC(O)=O JXEHXYFSIOYTAH-SFYZADRCSA-N 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
238000009169 immunotherapy Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
NDDAHWYSQHTHNT-UHFFFAOYSA-N indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 description 1
229960004569 indapamide Drugs 0.000 description 1
229950009810 indolapril Drugs 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
208000000509 infertility Diseases 0.000 description 1
230000036512 infertility Effects 0.000 description 1
231100000535 infertility Toxicity 0.000 description 1
208000021267 infertility disease Diseases 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
229940120120 innopran Drugs 0.000 description 1
239000004041 inotropic agent Substances 0.000 description 1
229940030980 inova Drugs 0.000 description 1
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 1
239000004026 insulin derivative Substances 0.000 description 1
238000001361 intraarterial administration Methods 0.000 description 1
238000007917 intracranial administration Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000007913 intrathecal administration Methods 0.000 description 1
238000007915 intraurethral administration Methods 0.000 description 1
238000007914 intraventricular administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
229960002198 irbesartan Drugs 0.000 description 1
YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
229940088024 isoptin Drugs 0.000 description 1
MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
229960000201 isosorbide dinitrate Drugs 0.000 description 1
YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 1
229960003827 isosorbide mononitrate Drugs 0.000 description 1
229960004427 isradipine Drugs 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
229940116871 l-lactate Drugs 0.000 description 1
229960001632 labetalol Drugs 0.000 description 1
230000003902 lesion Effects 0.000 description 1
239000003446 ligand Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
208000022215 lipoatrophic diabetes Diseases 0.000 description 1
201000009099 lipoatrophic diabetes mellitus Diseases 0.000 description 1
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
229960002394 lisinopril Drugs 0.000 description 1
CZRQXSDBMCMPNJ-ZUIPZQNBSA-N lisinopril dihydrate Chemical compound O.O.C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 CZRQXSDBMCMPNJ-ZUIPZQNBSA-N 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
210000004446 longitudinal ligament Anatomy 0.000 description 1
230000007774 longterm Effects 0.000 description 1
229960004773 losartan Drugs 0.000 description 1
KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
239000006210 lotion Substances 0.000 description 1
229960004844 lovastatin Drugs 0.000 description 1
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
208000002780 macular degeneration Diseases 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229940091250 magnesium supplement Drugs 0.000 description 1
QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
208000024714 major depressive disease Diseases 0.000 description 1
229940049920 malate Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
229960003105 metformin Drugs 0.000 description 1
OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
150000004704 methoxides Chemical class 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
DYROHZMICXBUMX-UHFFFAOYSA-N methoxymethylidene(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=COC)C1=CC=CC=C1 DYROHZMICXBUMX-UHFFFAOYSA-N 0.000 description 1
VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
CUCICJZHJKDCBT-UHFFFAOYSA-N methyl 5-carbamoyl-1-(2-ethoxyethyl)-4-nitropyrazole-3-carboxylate Chemical compound CCOCCN1N=C(C(=O)OC)C([N+]([O-])=O)=C1C(N)=O CUCICJZHJKDCBT-UHFFFAOYSA-N 0.000 description 1
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
MKUWVMRNQOOSAT-UHFFFAOYSA-N methylvinylmethanol Natural products CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 1
AQCHWTWZEMGIFD-UHFFFAOYSA-N metolazone Chemical compound CC1NC2=CC(Cl)=C(S(N)(=O)=O)C=C2C(=O)N1C1=CC=CC=C1C AQCHWTWZEMGIFD-UHFFFAOYSA-N 0.000 description 1
229960002817 metolazone Drugs 0.000 description 1
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
229960002237 metoprolol Drugs 0.000 description 1
239000004530 micro-emulsion Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229960001110 miglitol Drugs 0.000 description 1
206010052787 migraine without aura Diseases 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
208000006887 mitral valve stenosis Diseases 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229960005170 moexipril Drugs 0.000 description 1
XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 description 1
229960004027 molsidomine Drugs 0.000 description 1
125000006682 monohaloalkyl group Chemical group 0.000 description 1
230000003232 mucoadhesive effect Effects 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 1
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
XHXVAJHZTIXQQD-UHFFFAOYSA-N n-[bis(aziridin-1-yl)phosphoryl]-5-[(4-butoxyphenyl)methyl]-2,6-dimethylpyrimidin-4-amine Chemical compound C1=CC(OCCCC)=CC=C1CC1=C(C)N=C(C)N=C1NP(=O)(N1CC1)N1CC1 XHXVAJHZTIXQQD-UHFFFAOYSA-N 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 description 1
229960004255 nadolol Drugs 0.000 description 1
239000002105 nanoparticle Substances 0.000 description 1
OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
229960000698 nateglinide Drugs 0.000 description 1
125000005484 neopentoxy group Chemical group 0.000 description 1
230000009826 neoplastic cell growth Effects 0.000 description 1
201000008383 nephritis Diseases 0.000 description 1
HPNRHPKXQZSDFX-OAQDCNSJSA-N nesiritide Chemical compound C([C@H]1C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)CNC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CO)C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1N=CNC=1)C(O)=O)=O)[C@@H](C)CC)C1=CC=CC=C1 HPNRHPKXQZSDFX-OAQDCNSJSA-N 0.000 description 1
229960001267 nesiritide Drugs 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
208000021722 neuropathic pain Diseases 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
229960001597 nifedipine Drugs 0.000 description 1
239000002353 niosome Substances 0.000 description 1
229960000227 nisoldipine Drugs 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
150000002829 nitrogen Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229940103453 novolin Drugs 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229950004864 olamine Drugs 0.000 description 1
VTRAEEWXHOVJFV-UHFFFAOYSA-N olmesartan Chemical compound CCCC1=NC(C(C)(C)O)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 VTRAEEWXHOVJFV-UHFFFAOYSA-N 0.000 description 1
229960005117 olmesartan Drugs 0.000 description 1
229960001199 olmesartan medoxomil Drugs 0.000 description 1
LVRLSYPNFFBYCZ-VGWMRTNUSA-N omapatrilat Chemical compound C([C@H](S)C(=O)N[C@H]1CCS[C@H]2CCC[C@H](N2C1=O)C(=O)O)C1=CC=CC=C1 LVRLSYPNFFBYCZ-VGWMRTNUSA-N 0.000 description 1
229950000973 omapatrilat Drugs 0.000 description 1
238000011275 oncology therapy Methods 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
230000008816 organ damage Effects 0.000 description 1
229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
PXQPEWDEAKTCGB-UHFFFAOYSA-M orotate Chemical compound [O-]C(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-M 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000003544 oxime group Chemical group 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
208000027753 pain disease Diseases 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
KQXKVJAGOJTNJS-HNNXBMFYSA-N penbutolol Chemical compound CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1 KQXKVJAGOJTNJS-HNNXBMFYSA-N 0.000 description 1
229960002035 penbutolol Drugs 0.000 description 1
230000035515 penetration Effects 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
229950008492 pentopril Drugs 0.000 description 1
208000008494 pericarditis Diseases 0.000 description 1
229960002582 perindopril Drugs 0.000 description 1
IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
229960003418 phenoxybenzamine Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 1
229960002508 pindolol Drugs 0.000 description 1
229960005095 pioglitazone Drugs 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
CXWQAPHDSYDHBR-UHFFFAOYSA-N piperidine-4-carboxamide Chemical compound NC(=O)C1CCNCC1.NC(=O)C1CCNCC1 CXWQAPHDSYDHBR-UHFFFAOYSA-N 0.000 description 1
229950008688 pivopril Drugs 0.000 description 1
238000000711 polarimetry Methods 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
125000006684 polyhaloalkyl group Polymers 0.000 description 1
208000005987 polymyositis Diseases 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
231100000857 poor renal function Toxicity 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229960002965 pravastatin Drugs 0.000 description 1
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
201000011461 pre-eclampsia Diseases 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
201000009104 prediabetes syndrome Diseases 0.000 description 1
AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 1
229960001233 pregabalin Drugs 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
208000026440 premature labor Diseases 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
208000013846 primary aldosteronism Diseases 0.000 description 1
201000009395 primary hyperaldosteronism Diseases 0.000 description 1
VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940121649 protein inhibitor Drugs 0.000 description 1
239000012268 protein inhibitor Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003236 psychic effect Effects 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
208000002815 pulmonary hypertension Diseases 0.000 description 1
UYLWKSJTHLRFBX-UHFFFAOYSA-N purin-6-one Chemical class O=C1N=CN=C2N=CN=C12 UYLWKSJTHLRFBX-UHFFFAOYSA-N 0.000 description 1
125000004308 pyranonyl group Chemical group O1C(C(=CC=C1)*)=O 0.000 description 1
XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
IUYQIJQHYDZUDF-UHFFFAOYSA-N pyrazolo[3,4-d]pyrimidin-4-one Chemical class O=C1N=CN=C2N=NC=C12 IUYQIJQHYDZUDF-UHFFFAOYSA-N 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
125000006513 pyridinyl methyl group Chemical group 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
208000022587 qualitative or quantitative defects of dystrophin Diseases 0.000 description 1
229940073095 questran Drugs 0.000 description 1
229960001455 quinapril Drugs 0.000 description 1
JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
229960003401 ramipril Drugs 0.000 description 1
HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
239000002461 renin inhibitor Substances 0.000 description 1
229940086526 renin-inhibitors Drugs 0.000 description 1
229960002354 repaglinide Drugs 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
239000002151 riboflavin Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
229960004586 rosiglitazone Drugs 0.000 description 1
229960000672 rosuvastatin Drugs 0.000 description 1
BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
210000003131 sacroiliac joint Anatomy 0.000 description 1
229950001780 sampatrilat Drugs 0.000 description 1
239000004576 sand Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229960002855 simvastatin Drugs 0.000 description 1
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
210000002027 skeletal muscle Anatomy 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940083618 sodium nitroprusside Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
ZRHIRBWUAAAOJE-UHFFFAOYSA-N sodium;4,4,4-trifluorobutan-1-olate Chemical compound [Na+].[O-]CCCC(F)(F)F ZRHIRBWUAAAOJE-UHFFFAOYSA-N 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
241000894007 species Species 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
229960002909 spirapril Drugs 0.000 description 1
HRWCVUIFMSZDJS-SZMVWBNQSA-N spirapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)CC1=CC=CC=C1 HRWCVUIFMSZDJS-SZMVWBNQSA-N 0.000 description 1
108700035424 spirapril Proteins 0.000 description 1
LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
229960002256 spironolactone Drugs 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000010922 spray-dried dispersion Methods 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000009747 swallowing Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960000651 tasosartan Drugs 0.000 description 1
ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
229960005187 telmisartan Drugs 0.000 description 1
VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
229960001693 terazosin Drugs 0.000 description 1
BZVHDLWVOYINCR-UHFFFAOYSA-N tert-butyl 4-[1-(2-ethoxyethyl)-3-(1-hydroxyethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical compound C=12N(CCOCC)N=C(C(C)O)C2=NC(N2CCN(CC2)C(=O)OC(C)(C)C)=NC=1NC1=CC(C)=CC=N1 BZVHDLWVOYINCR-UHFFFAOYSA-N 0.000 description 1
JXFTYNQQRGAODA-UHFFFAOYSA-N tert-butyl 4-[1-(2-ethoxyethyl)-3-(hydroxymethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-5-yl]piperazine-1-carboxylate Chemical compound C=12N(CCOCC)N=C(CO)C2=NC(N2CCN(CC2)C(=O)OC(C)(C)C)=NC=1NC1=CC(C)=CC=N1 JXFTYNQQRGAODA-UHFFFAOYSA-N 0.000 description 1
LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical group CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 1
CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical group CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 1
OFBWJMQYKLZJTG-UHFFFAOYSA-N tert-butyl-[[5,7-dichloro-1-(2-ethoxyethyl)pyrazolo[4,3-d]pyrimidin-3-yl]methoxy]-dimethylsilane Chemical compound ClC1=NC(Cl)=C2N(CCOCC)N=C(CO[Si](C)(C)C(C)(C)C)C2=N1 OFBWJMQYKLZJTG-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 description 1
125000006173 tetrahydropyranylmethyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
150000001467 thiazolidinediones Chemical class 0.000 description 1
125000002769 thiazolinyl group Chemical group 0.000 description 1
125000001166 thiolanyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
229960004605 timolol Drugs 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
229960005461 torasemide Drugs 0.000 description 1
CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 description 1
229950004514 torcetrapib Drugs 0.000 description 1
229960002051 trandolapril Drugs 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
238000000844 transformation Methods 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
229960001288 triamterene Drugs 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
206010044652 trigeminal neuralgia Diseases 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
208000009852 uremia Diseases 0.000 description 1
229960004699 valsartan Drugs 0.000 description 1
SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
210000003556 vascular endothelial cell Anatomy 0.000 description 1
210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1
208000030401 vitamin deficiency disease Diseases 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
229960002769 zofenopril Drugs 0.000 description 1
FIKYECRHLXONOX-UHFFFAOYSA-N zolasartan Chemical compound CCCCC1=NC(Cl)=C(C(O)=O)N1CC1=CC=C(OC(=C2Br)C=3C(=CC=CC=3)C3=NNN=N3)C2=C1 FIKYECRHLXONOX-UHFFFAOYSA-N 0.000 description 1
229950004433 zolasartan Drugs 0.000 description 1
210000002517 zygapophyseal joint Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Diabetes (AREA)
Hematology (AREA)
Endocrinology (AREA)
Obesity (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Reproductive Health (AREA)
Physical Education & Sports Medicine (AREA)
Ophthalmology & Optometry (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Dermatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Gynecology & Obstetrics (AREA)
Psychiatry (AREA)
Pulmonology (AREA)
Addiction (AREA)
Pregnancy & Childbirth (AREA)
Immunology (AREA)
Oncology (AREA)
Hospice & Palliative Care (AREA)

CA002585557A 2004-10-28 2005-10-17 Nouveaux composes pharmaceutiques Expired - Fee Related CA2585557C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US62294104P	2004-10-28	2004-10-28
US60/622,941		2004-10-28
PCT/IB2005/003326 WO2006046135A2 (fr)	2004-10-28	2005-10-17	Nouveaux composes pharmaceutiques

Publications (2)

Publication Number	Publication Date
CA2585557A1 CA2585557A1 (fr)	2006-05-04
CA2585557C true CA2585557C (fr)	2009-08-18

Family

ID=35530735

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002585557A Expired - Fee Related CA2585557C (fr)	2004-10-28	2005-10-17	Nouveaux composes pharmaceutiques

Country Status (4)

Country	Link
EP (1)	EP1809632A2 (fr)
JP (1)	JP2008517994A (fr)
CA (1)	CA2585557C (fr)
WO (1)	WO2006046135A2 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT1881985E (pt)	2005-05-12	2011-02-01	Pfizer	Formas cristalinas anidras de n-[1-(2-etoxietil)-5-(n- -etil-n-metilamino)-7-(4-metilpiridin-2-il-amino)-1h- -pirazolo[4,3-d]pirimidino-3-carbonil]metanossulfonamida
NL2000291C2 (nl)	2005-11-10	2009-02-17	Pfizer Prod Inc	1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H- pyrazool(4,3-d)pyrimidine-5-yl)piperidine-4-carbonzuur en zouten daarvan.
ES2310144B1 (es)	2007-06-15	2010-01-12	Galenicum Health, S.L.	Intermedios para la preparacion de un inhibidor de la fosfodiesterasa tipo 5.
DK2646443T3 (en)	2010-12-01	2014-11-17	Pfizer	CAT-II inhibitors
IN2014DN07224A (fr)	2012-02-03	2015-04-24	Basf Se
IN2014DN07954A (fr)	2012-03-13	2015-05-01	Basf Se
US9422267B2 (en)	2012-12-26	2016-08-23	Medivation Technologies, Inc.	Fused pyrimidine compounds and use thereof
WO2015036059A1 (fr)	2013-09-16	2015-03-19	Basf Se	Composés fongicides de pyrimidine
US11554120B2 (en) *	2018-08-03	2023-01-17	Bristol-Myers Squibb Company	1H-pyrazolo[4,3-d]pyrimidine compounds as toll-like receptor 7 (TLR7) agonists and methods and uses therefor
CN115322105A (zh) *	2021-05-11	2022-11-11	江苏润安制药有限公司	一种合成艾拉莫德关键中间体的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10031584A1 (de) *	2000-06-29	2002-01-10	Merck Patent Gmbh	5-Aminoalkyl-pyrazolo[4,3-d]pyrimidine
KR100824193B1 (ko) *	2003-04-29	2008-04-21	화이자 인코포레이티드	고혈압 치료에 유용한5,7-디아미노피라졸로[4,3-ｄ]피리미딘
GB0327319D0 (en) *	2003-11-24	2003-12-24	Pfizer Ltd	Novel pharmaceuticals

2005
- 2005-10-17 EP EP05800579A patent/EP1809632A2/fr not_active Withdrawn
- 2005-10-17 JP JP2007538544A patent/JP2008517994A/ja not_active Withdrawn
- 2005-10-17 WO PCT/IB2005/003326 patent/WO2006046135A2/fr not_active Ceased
- 2005-10-17 CA CA002585557A patent/CA2585557C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP2008517994A (ja)	2008-05-29
WO2006046135A3 (fr)	2006-08-17
WO2006046135A2 (fr)	2006-05-04
CA2585557A1 (fr)	2006-05-04
EP1809632A2 (fr)	2007-07-25

Legal Events

Date	Code	Title	Description
2007-04-27	EEER	Examination request
2010-10-18	MKLA	Lapsed

Publication	Publication Date	Title
CA2523831C (fr)	2008-11-18	5,7-diaminopyrazolo[4,3]d!pyrimidines utiles pour le traitement de l'hypertension
CA2546987C (fr)	2009-05-12	5,7-diaminopyrazolo [4,3-d] pyrimidines a effet inhibiteur par rapport ala pde-5
AU2012288491A1 (en)	2014-01-30	Indazoles
KR20160058188A (ko)	2016-05-24	Ｂｔｋ의 치환된 니코틴이미드 저해제 및 그의 제조 방법 및 암, 염증 및 자가면역 질환에의 용도
KR20020038941A (ko)	2002-05-24	포스포디에스테라아제 억제제로서의5-(2-치환된-5-헤테로사이클릴설포닐피리드-3-일)-디하이드로피라졸로[4,3-ｄ]피리미딘-7-온
CA2791166A1 (fr)	2011-09-01	Composes pyrazolopyrimidines et leur utilisation comme inhibiteur de la pde10
EP2935272A1 (fr)	2015-10-28	Utilisation d'imidazopyrazines à substitution pyrazole comme inhibiteurs de caséine kinase 1 d/e
EP1809632A2 (fr)	2007-07-25	Derives de pyrazolo [4,3-d] pyrimidine utiles comme inhibiteurs de pde-5
HK1142522A (en)	2010-12-10	5, 7-diaminopyrazolo [4,3-d] pyrimidines with pde -5 inhibiting activity and composition thereof
HK1087108B (en)	2009-07-03	5,7-diaminopyrazolo[4,3-d]pyrimidines useful in the treatment of hypertension
HK1099286B (en)	2012-06-01	5,7-diaminopyrazolo [4,3-d] pyrimidines with pde-5 inhibiting activity
HK1128917B (en)	2011-12-09	5,7-diaminopyrazolo [4,3-d] pyrimidines with pde-5 inhibiting activity