HRP960465A2 - Heterocyclic compounds - Google Patents

Heterocyclic compounds Download PDF

Info

Publication number: HRP960465A2
Authority: HR; Croatia
Prior art keywords: pyrimidine; alkyl; pyrido; alkoxy; compound
Prior art date: 1995-10-11

Application number

HR9614757.4A

Other languages

English (en)

Croatian (hr)

Inventor

George Stuart Cockerill

Steven Barry Guntrip

Steven Carl Mckeown

Martin John Page

Kathryn Jane Smith

Saide Vile

Alan Thomas Hudson

Original Assignee

Glaxo Group Ltd

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.)

1995-10-11

Filing date

1996-10-10

Publication date

1998-02-28

1995-10-11 Priority claimed from GBGB9520845.0A external-priority patent/GB9520845D0/en

1996-07-13 Priority claimed from GBGB9614757.4A external-priority patent/GB9614757D0/en

1996-10-10 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1998-02-28 Publication of HRP960465A2 publication Critical patent/HRP960465A2/hr

Links

150000002391 heterocyclic compounds Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 125
238000000034 method Methods 0.000 claims description 85
-1 trifluoromethoxy, nitro, amino Chemical group 0.000 claims description 62
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 47
125000003545 alkoxy group Chemical group 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 39
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 29
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 28
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 28
229910052760 oxygen Inorganic materials 0.000 claims description 26
238000011282 treatment Methods 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
125000003282 alkyl amino group Chemical group 0.000 claims description 22
230000000694 effects Effects 0.000 claims description 22
125000000623 heterocyclic group Chemical group 0.000 claims description 22
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 19
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
239000000825 pharmaceutical preparation Substances 0.000 claims description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
208000035475 disorder Diseases 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000002837 carbocyclic group Chemical group 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
230000008569 process Effects 0.000 claims description 11
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
230000001594 aberrant effect Effects 0.000 claims description 10
125000005236 alkanoylamino group Chemical group 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
QXOVLZVIYMRNAV-UHFFFAOYSA-N 6-chloro-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 QXOVLZVIYMRNAV-UHFFFAOYSA-N 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
241001465754 Metazoa Species 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
230000001404 mediated effect Effects 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 7
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
201000011510 cancer Diseases 0.000 claims description 6
125000004989 dicarbonyl group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
WXTYHXBDAUYJQS-UHFFFAOYSA-N n-[4-(benzenesulfonyl)phenyl]-6-chloropyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 WXTYHXBDAUYJQS-UHFFFAOYSA-N 0.000 claims description 6
DOKKMZLPMGLGJX-UHFFFAOYSA-N 6-(3-methylimidazol-4-yl)-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CN1C=NC=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 DOKKMZLPMGLGJX-UHFFFAOYSA-N 0.000 claims description 5
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
BQNICBAZEPWTNW-UHFFFAOYSA-N 4-n-[4-(1,3-dioxolan-2-ylmethoxy)phenyl]-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1)=CC=C1OCC1OCCO1 BQNICBAZEPWTNW-UHFFFAOYSA-N 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
JAKTZPDFCZIXQM-UHFFFAOYSA-N 6-n,6-n-dimethyl-4-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 JAKTZPDFCZIXQM-UHFFFAOYSA-N 0.000 claims description 4
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
YTKICSVFCXOIJB-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)-6-thiomorpholin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1NC(C1=C2)=NC=NC1=CN=C2N1CCSCC1 YTKICSVFCXOIJB-UHFFFAOYSA-N 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
PAQYIEZTLSDLQO-UHFFFAOYSA-N pyrido[3,4-d]pyrimidine Chemical compound N1=CN=C2C=NC=CC2=C1 PAQYIEZTLSDLQO-UHFFFAOYSA-N 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
208000037803 restenosis Diseases 0.000 claims description 4
229910052720 vanadium Inorganic materials 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
NGGKKVSEPYCGNW-UHFFFAOYSA-N 2-[[4-[4-(benzenesulfonyl)anilino]pyrido[3,4-d]pyrimidin-6-yl]-methylamino]ethanol Chemical compound N1=CN=C2C=NC(N(CCO)C)=CC2=C1NC(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 NGGKKVSEPYCGNW-UHFFFAOYSA-N 0.000 claims description 3
XXKCPVIIXOPXEP-UHFFFAOYSA-N 4-n-[4-(benzenesulfonyl)phenyl]-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 XXKCPVIIXOPXEP-UHFFFAOYSA-N 0.000 claims description 3
UPIYTHRGZLPZQS-UHFFFAOYSA-N 5-[4-(4-phenylmethoxyanilino)pyrido[3,4-d]pyrimidin-6-yl]furan-2-carbaldehyde Chemical compound O1C(C=O)=CC=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 UPIYTHRGZLPZQS-UHFFFAOYSA-N 0.000 claims description 3
DNAQHZRAPBUFQJ-UHFFFAOYSA-N 6-(1-methylimidazol-2-yl)-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CN1C=CN=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 DNAQHZRAPBUFQJ-UHFFFAOYSA-N 0.000 claims description 3
LZQOJWXKGWWUSQ-UHFFFAOYSA-N 6-(furan-2-yl)-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1NC(C1=C2)=NC=NC1=CN=C2C1=CC=CO1 LZQOJWXKGWWUSQ-UHFFFAOYSA-N 0.000 claims description 3
GXFDHJDKDGVBRU-UHFFFAOYSA-N 6-chloro-n-[4-(1,3-dioxolan-2-ylmethoxy)phenyl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1)=CC=C1OCC1OCCO1 GXFDHJDKDGVBRU-UHFFFAOYSA-N 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 3
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
208000007536 Thrombosis Diseases 0.000 claims description 3
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
150000007942 carboxylates Chemical class 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
YQQXWIQTZVBINC-UHFFFAOYSA-N n-[4-(benzenesulfonyl)phenyl]-6-(4-methylpiperazin-1-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C(N=CC1=NC=N2)=CC1=C2NC1=CC=C(S(=O)(=O)C=2C=CC=CC=2)C=C1 YQQXWIQTZVBINC-UHFFFAOYSA-N 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
229930192474 thiophene Chemical group 0.000 claims description 3
229910052721 tungsten Inorganic materials 0.000 claims description 3
TYOJYLRMQHRNOX-UHFFFAOYSA-N 2-[4-[[6-(dimethylamino)pyrido[3,4-d]pyrimidin-4-yl]amino]phenyl]-2-phenylacetonitrile Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1)=CC=C1C(C#N)C1=CC=CC=C1 TYOJYLRMQHRNOX-UHFFFAOYSA-N 0.000 claims description 2
ZMCMFEUHXKDHQG-UHFFFAOYSA-N 4-n-[4-(benzenesulfonyl)phenyl]-6-n-[2-(dimethylamino)ethyl]-6-n-methylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)CCN(C)C)=CC2=C1NC(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 ZMCMFEUHXKDHQG-UHFFFAOYSA-N 0.000 claims description 2
IQJVEWGFUVNHPS-UHFFFAOYSA-N 4-n-[4-[(3-fluorophenyl)methoxy]phenyl]-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 IQJVEWGFUVNHPS-UHFFFAOYSA-N 0.000 claims description 2
125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
ZUCRFFRRDPTULV-UHFFFAOYSA-N 6-(4-methylpiperazin-1-yl)-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C(N=CC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 ZUCRFFRRDPTULV-UHFFFAOYSA-N 0.000 claims description 2
BRJBLARSOFKJME-UHFFFAOYSA-N 6-chloro-n-(4-phenylsulfanylphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1)=CC=C1SC1=CC=CC=C1 BRJBLARSOFKJME-UHFFFAOYSA-N 0.000 claims description 2
HCFTYUFPNVXOJF-UHFFFAOYSA-N 6-phenylmethoxy-n-(4-phenylmethoxyphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1NC(C1=C2)=NC=NC1=CN=C2OCC1=CC=CC=C1 HCFTYUFPNVXOJF-UHFFFAOYSA-N 0.000 claims description 2
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
125000005110 aryl thio group Chemical group 0.000 claims description 2
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000005879 dioxolanyl group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
MJQAMWVEPJHQQZ-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(NC=2C3=CC=CN=C3N=CN=2)C=CC=1OCC1=CC=CC=C1 MJQAMWVEPJHQQZ-UHFFFAOYSA-N 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 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 claims description 2
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
125000005554 pyridyloxy group Chemical group 0.000 claims description 2
229940124530 sulfonamide Drugs 0.000 claims description 2
150000003456 sulfonamides Chemical class 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
229940079593 drug Drugs 0.000 claims 3
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 2
HGVWHDUJXWPIFH-UHFFFAOYSA-N 4-n-(3-chloro-4-phenylmethoxyphenyl)-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1 HGVWHDUJXWPIFH-UHFFFAOYSA-N 0.000 claims 1
DVOJKAZVHWAKET-UHFFFAOYSA-N 7-methyl-n-(4-phenoxyphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 DVOJKAZVHWAKET-UHFFFAOYSA-N 0.000 claims 1
QCNWIOGBGNQTAN-UHFFFAOYSA-N 7-methyl-n-[4-phenylmethoxy-3-(trifluoromethyl)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NC(C=C1C(F)(F)F)=CC=C1OCC1=CC=CC=C1 QCNWIOGBGNQTAN-UHFFFAOYSA-N 0.000 claims 1
125000000000 cycloalkoxy group Chemical group 0.000 claims 1
GWELHWZVDHWXOD-UHFFFAOYSA-N n-(4-benzylphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1CC1=CC=CC=C1 GWELHWZVDHWXOD-UHFFFAOYSA-N 0.000 claims 1
MLGCIGKABIXNCH-UHFFFAOYSA-N n-(4-phenoxyphenyl)-5-thiophen-2-ylthieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2SC=C(C=3SC=CC=3)C=2C=1NC(C=C1)=CC=C1OC1=CC=CC=C1 MLGCIGKABIXNCH-UHFFFAOYSA-N 0.000 claims 1
ZSWUAMCGOVXUQL-UHFFFAOYSA-N n-(4-phenoxyphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound N=1C=NC=2C=CSC=2C=1NC(C=C1)=CC=C1OC1=CC=CC=C1 ZSWUAMCGOVXUQL-UHFFFAOYSA-N 0.000 claims 1
FZALGTPXQZDQND-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1OCC1=CC=CC=C1 FZALGTPXQZDQND-UHFFFAOYSA-N 0.000 claims 1
LJILSPYXOKMTGZ-UHFFFAOYSA-N n-[3-chloro-4-[(2-fluorophenyl)methoxy]phenyl]-5-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C)=CSC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1F LJILSPYXOKMTGZ-UHFFFAOYSA-N 0.000 claims 1
KKGIBJKTQQCUSF-UHFFFAOYSA-N n-[3-chloro-4-[(2-fluorophenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound FC1=CC=CC=C1COC(C(=C1)Cl)=CC=C1NC1=NC=NC2=C1SC=C2 KKGIBJKTQQCUSF-UHFFFAOYSA-N 0.000 claims 1
FIEPNGQUUSUAPN-UHFFFAOYSA-N n-[3-chloro-4-[(2-methoxyphenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound COC1=CC=CC=C1COC(C(=C1)Cl)=CC=C1NC1=NC=NC2=C1SC=C2 FIEPNGQUUSUAPN-UHFFFAOYSA-N 0.000 claims 1
FMHSSZBRISKOBK-UHFFFAOYSA-N n-[3-methoxy-4-[(2-methoxyphenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound COC1=CC=CC=C1COC(C(=C1)OC)=CC=C1NC1=NC=NC2=C1SC=C2 FMHSSZBRISKOBK-UHFFFAOYSA-N 0.000 claims 1
PRRAODUKSVKQQJ-UHFFFAOYSA-N n-[4-(cyclohexylmethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1OCC1CCCCC1 PRRAODUKSVKQQJ-UHFFFAOYSA-N 0.000 claims 1
MFQDINXHDBLVFM-UHFFFAOYSA-N n-[4-(thiophen-2-ylmethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1OCC1=CC=CS1 MFQDINXHDBLVFM-UHFFFAOYSA-N 0.000 claims 1
JOXKCVILYFDEMM-UHFFFAOYSA-N n-[4-[(2-bromophenyl)methoxy]-3-chlorophenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound ClC1=CC(NC=2C=3SC=CC=3N=CN=2)=CC=C1OCC1=CC=CC=C1Br JOXKCVILYFDEMM-UHFFFAOYSA-N 0.000 claims 1
RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims 1
125000005505 thiomorpholino group Chemical group 0.000 claims 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 59
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 47
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 34
239000000047 product Substances 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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XKKIPRNFABKBDW-UHFFFAOYSA-N n-[3-chloro-4-[(2-fluorophenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.FC1=CC=CC=C1COC(C(=C1)Cl)=CC=C1NC1=NC=NC2=C1SC=C2 XKKIPRNFABKBDW-UHFFFAOYSA-N 0.000 description 1
TXEVAORXZXOVAP-UHFFFAOYSA-N n-[3-chloro-4-[(2-methoxyphenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC=C1COC(C(=C1)Cl)=CC=C1NC1=NC=NC2=C1SC=C2 TXEVAORXZXOVAP-UHFFFAOYSA-N 0.000 description 1
QAXVWZBEQAHKRO-UHFFFAOYSA-N n-[3-methoxy-4-[(2-methoxyphenyl)methoxy]phenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC=C1COC(C(=C1)OC)=CC=C1NC1=NC=NC2=C1SC=C2 QAXVWZBEQAHKRO-UHFFFAOYSA-N 0.000 description 1
QZHRWYONEKRKIV-UHFFFAOYSA-N n-[4-(cyclohexylmethoxy)phenyl]-5-methylthieno[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=12C(C)=CSC2=NC=NC=1NC(C=C1)=CC=C1OCC1CCCCC1 QZHRWYONEKRKIV-UHFFFAOYSA-N 0.000 description 1
VCHIWKNEEJOWDH-UHFFFAOYSA-N n-[4-(cyclohexylmethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1OCC1CCCCC1 VCHIWKNEEJOWDH-UHFFFAOYSA-N 0.000 description 1
XOEBIPHQEASZSY-UHFFFAOYSA-N n-[4-(thiophen-2-ylmethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=1C=C(NC=2C=3SC=CC=3N=CN=2)C=CC=1OCC1=CC=CS1 XOEBIPHQEASZSY-UHFFFAOYSA-N 0.000 description 1
NHQXBUYAPLBXDL-UHFFFAOYSA-N n-[4-[(2-bromophenyl)methoxy]-3-chlorophenyl]thieno[3,2-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.ClC1=CC(NC=2C=3SC=CC=3N=CN=2)=CC=C1OCC1=CC=CC=C1Br NHQXBUYAPLBXDL-UHFFFAOYSA-N 0.000 description 1
QRLOPDIVUDLFSZ-UHFFFAOYSA-N n-benzylpyrimidin-4-amine Chemical class C=1C=CC=CC=1CNC1=CC=NC=N1 QRLOPDIVUDLFSZ-UHFFFAOYSA-N 0.000 description 1
239000007923 nasal drop Substances 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
229940097496 nasal spray Drugs 0.000 description 1
239000007922 nasal spray Substances 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
238000011369 optimal treatment Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
201000002528 pancreatic cancer Diseases 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
108060006633 protein kinase Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
RKOZEGQZEADBAT-UHFFFAOYSA-N pyrido[3,4-d]pyrimidine hydrochloride Chemical compound Cl.N1=CN=C2C=NC=CC2=C1 RKOZEGQZEADBAT-UHFFFAOYSA-N 0.000 description 1
IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000009703 regulation of cell differentiation Effects 0.000 description 1
230000010076 replication Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 1
229940100611 topical cream Drugs 0.000 description 1
229940100615 topical ointment Drugs 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000013519 translation Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
SANWDQJIWZEKOD-UHFFFAOYSA-N tributyl(furan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CO1 SANWDQJIWZEKOD-UHFFFAOYSA-N 0.000 description 1
CUTVPKSVLXXPII-UHFFFAOYSA-N tributyl-(1-methyl-3h-pyrazol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)N1CC=CN1C CUTVPKSVLXXPII-UHFFFAOYSA-N 0.000 description 1
KFWFYOPKNSYTMV-UHFFFAOYSA-N tributyl-(1-methylimidazol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CN1C KFWFYOPKNSYTMV-UHFFFAOYSA-N 0.000 description 1
OGYWKJKAIAEDQX-UHFFFAOYSA-N tributyl-(3-methylimidazol-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=CN1C OGYWKJKAIAEDQX-UHFFFAOYSA-N 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
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
231100000588 tumorigenic Toxicity 0.000 description 1
230000000381 tumorigenic effect Effects 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- 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
- 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
- A61P9/10—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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

HR9614757.4A 1995-10-11 1996-10-10 Heterocyclic compounds HRP960465A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9520845.0A GB9520845D0 (en)	1995-10-11	1995-10-11	Therapeutically active compounds
GBGB9614757.4A GB9614757D0 (en)	1996-07-13	1996-07-13	Therapeutically active compounds

Publications (1)

Publication Number	Publication Date
HRP960465A2 true HRP960465A2 (en)	1998-02-28

Family

ID=26307933

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR9614757.4A HRP960465A2 (en)	1995-10-11	1996-10-10	Heterocyclic compounds

Country Status (8)

Country	Link
US (1)	US6169091B1 (id)
EP (1)	EP0861253A1 (id)
JP (1)	JPH11513398A (id)
AR (1)	AR004010A1 (id)
AU (1)	AU7289696A (id)
HR (1)	HRP960465A2 (id)
ID (1)	ID16345A (id)
WO (1)	WO1997013771A1 (id)

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- 1996-10-10 EP EP96934612A patent/EP0861253A1/en not_active Withdrawn
- 1996-10-10 AU AU72896/96A patent/AU7289696A/en not_active Abandoned
- 1996-10-10 HR HR9614757.4A patent/HRP960465A2/hr not_active Application Discontinuation
- 1996-10-10 US US09/051,324 patent/US6169091B1/en not_active Expired - Fee Related
- 1996-10-10 JP JP9514711A patent/JPH11513398A/ja active Pending
- 1996-10-10 WO PCT/EP1996/004399 patent/WO1997013771A1/en not_active Ceased

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Publication number	Publication date
AR004010A1 (es)	1998-09-30
AU7289696A (en)	1997-04-30
JPH11513398A (ja)	1999-11-16
EP0861253A1 (en)	1998-09-02
US6169091B1 (en)	2001-01-02
ID16345A (id)	1997-09-25
WO1997013771A1 (en)	1997-04-17

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Date	Code	Title	Description
1998-02-28	A1OB	Publication of a patent application
1999-05-07	ODBC	Application rejected

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