UA77042C2 - Substituted 4-tetrahydroquinolines, use thereof as medicament, a medicament containing them - Google Patents

Substituted 4-tetrahydroquinolines, use thereof as medicament, a medicament containing them Download PDF

Info

Publication number: UA77042C2
Authority: UA; Ukraine
Prior art keywords: methyl; dichloro; tetrahydroisoquinolin; atoms; uphenyl
Prior art date: 2001-12-05

Application number

UA20040705310A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Sanofi Aventis Deutschland

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.)

2001-12-05

Filing date

2002-11-20

Publication date

2006-10-16

2002-11-20 Application filed by Sanofi Aventis Deutschland filed Critical Sanofi Aventis Deutschland

2006-10-16 Publication of UA77042C2 publication Critical patent/UA77042C2/uk

Links

239000003814 drug Substances 0.000 title abstract description 14
150000001875 compounds Chemical class 0.000 claims abstract description 166
238000011282 treatment Methods 0.000 claims abstract description 37
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
230000002265 prevention Effects 0.000 claims abstract description 19
201000010099 disease Diseases 0.000 claims abstract description 15
230000006378 damage Effects 0.000 claims abstract description 8
210000000056 organ Anatomy 0.000 claims abstract description 8
230000035939 shock Effects 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 279
-1 K12 radical Chemical class 0.000 claims description 168
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 152
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 124
125000004437 phosphorous atom Chemical group 0.000 claims description 119
125000004433 nitrogen atom Chemical group N* 0.000 claims description 113
229910052757 nitrogen Inorganic materials 0.000 claims description 107
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 76
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 62
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 60
150000001408 amides Chemical class 0.000 claims description 55
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 51
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 51
239000004202 carbamide Substances 0.000 claims description 49
239000002253 acid Substances 0.000 claims description 43
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 42
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 41
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 41
230000007958 sleep Effects 0.000 claims description 39
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 38
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 37
KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 35
150000003254 radicals Chemical class 0.000 claims description 34
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 32
229940080818 propionamide Drugs 0.000 claims description 32
STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 31
KNWWGBNAUNTSRV-UHFFFAOYSA-N 4-methylpiperazine-1-carboxylic acid Chemical compound CN1CCN(C(O)=O)CC1 KNWWGBNAUNTSRV-UHFFFAOYSA-N 0.000 claims description 30
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 30
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 28
229910052799 carbon Inorganic materials 0.000 claims description 28
229910052760 oxygen Inorganic materials 0.000 claims description 26
125000001424 substituent group Chemical group 0.000 claims description 26
229910052796 boron Inorganic materials 0.000 claims description 25
229940126601 medicinal product Drugs 0.000 claims description 25
GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 claims description 24
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 24
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 24
DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 claims description 24
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 23
NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 23
WFCLWJHOKCQYOQ-UHFFFAOYSA-N 1-acetylpiperidine-4-carboxylic acid Chemical compound CC(=O)N1CCC(C(O)=O)CC1 WFCLWJHOKCQYOQ-UHFFFAOYSA-N 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 22
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 22
DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 21
JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 20
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 19
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 18
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 18
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 17
SUGDSKDKCOFIQN-UHFFFAOYSA-N 1-methylsulfonylpiperidine-4-carboxylic acid Chemical compound CS(=O)(=O)N1CCC(C(O)=O)CC1 SUGDSKDKCOFIQN-UHFFFAOYSA-N 0.000 claims description 16
IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical compound OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 claims description 16
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 16
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 16
WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims description 16
HCKNAJXCHMACDN-UHFFFAOYSA-N 1-methylpiperidine-4-carboxylic acid Chemical compound CN1CCC(C(O)=O)CC1 HCKNAJXCHMACDN-UHFFFAOYSA-N 0.000 claims description 15
ZPXGMXNPRXENML-UHFFFAOYSA-N 5-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-2-hydroxybenzoic acid Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(O)C(C(O)=O)=C1 ZPXGMXNPRXENML-UHFFFAOYSA-N 0.000 claims description 15
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000002883 imidazolyl group Chemical group 0.000 claims description 15
125000002971 oxazolyl group Chemical group 0.000 claims description 15
125000003226 pyrazolyl group Chemical group 0.000 claims description 15
125000000168 pyrrolyl group Chemical group 0.000 claims description 15
125000003831 tetrazolyl group Chemical group 0.000 claims description 15
125000000335 thiazolyl group Chemical group 0.000 claims description 15
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 14
ROCHTQWNNZUYOK-UHFFFAOYSA-N 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzoic acid Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(C(O)=O)=C1 ROCHTQWNNZUYOK-UHFFFAOYSA-N 0.000 claims description 14
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 14
125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 14
125000003386 piperidinyl group Chemical group 0.000 claims description 14
125000004076 pyridyl group Chemical group 0.000 claims description 14
125000001425 triazolyl group Chemical group 0.000 claims description 14
OGVXGNOUQNLCAU-UHFFFAOYSA-N 4-(4-bromophenyl)-6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(Br)C=C1 OGVXGNOUQNLCAU-UHFFFAOYSA-N 0.000 claims description 13
229940057054 1,3-dimethylurea Drugs 0.000 claims description 12
NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 claims description 12
IOOWDXMXZBYKLR-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole-4-carboxylic acid Chemical compound CC1=NNC(C)=C1C(O)=O IOOWDXMXZBYKLR-UHFFFAOYSA-N 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
229960003966 nicotinamide Drugs 0.000 claims description 12
235000005152 nicotinamide Nutrition 0.000 claims description 12
239000011570 nicotinamide Substances 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
LUVXGUJFNMUWEZ-UHFFFAOYSA-N 1,2-dimethylimidazole-4-sulfonic acid Chemical compound CC1=NC(S(O)(=O)=O)=CN1C LUVXGUJFNMUWEZ-UHFFFAOYSA-N 0.000 claims description 11
QETVYTNAHZLDNS-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(S(N)(=O)=O)C=C1 QETVYTNAHZLDNS-UHFFFAOYSA-N 0.000 claims description 10
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
ITSVCLWKVUKMHH-UHFFFAOYSA-N 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)aniline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(N)=C1 ITSVCLWKVUKMHH-UHFFFAOYSA-N 0.000 claims description 9
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 9
XGMDYIYCKWMWLY-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonic acid Chemical compound OS(=O)(=O)CC(F)(F)F XGMDYIYCKWMWLY-UHFFFAOYSA-N 0.000 claims description 8
VDVWTJFVFQVCFN-UHFFFAOYSA-N 2,5-dimethyl-1h-pyrrole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=C(C)N1 VDVWTJFVFQVCFN-UHFFFAOYSA-N 0.000 claims description 8
WLQPUTXHTCZSFK-UHFFFAOYSA-N 5-bromothiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)S1 WLQPUTXHTCZSFK-UHFFFAOYSA-N 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 8
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims description 8
208000035475 disorder Diseases 0.000 claims description 8
125000004434 sulfur atom Chemical group 0.000 claims description 8
SELDCFUFDZPRLP-UHFFFAOYSA-N 1,4-dimethylpyrrole-2-carboxylic acid Chemical compound CC=1C=C(C(O)=O)N(C)C=1 SELDCFUFDZPRLP-UHFFFAOYSA-N 0.000 claims description 7
CHHASAIQKXOAOX-UHFFFAOYSA-N 1-(2,2-dimethylpropoxy)-2,2-dimethylpropane Chemical compound CC(C)(C)COCC(C)(C)C CHHASAIQKXOAOX-UHFFFAOYSA-N 0.000 claims description 7
OOPDWMLXBWNOLH-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzoic acid Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(C(O)=O)C=C1 OOPDWMLXBWNOLH-UHFFFAOYSA-N 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 7
230000000302 ischemic effect Effects 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
UNNPAFDYRLETBW-UHFFFAOYSA-N 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(S(N)(=O)=O)=C1 UNNPAFDYRLETBW-UHFFFAOYSA-N 0.000 claims description 6
JTXNWYHSDXNOAG-UHFFFAOYSA-N 4-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]morpholine Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1N1CCOCC1 JTXNWYHSDXNOAG-UHFFFAOYSA-N 0.000 claims description 6
WOSRCHOJUSCXJV-UHFFFAOYSA-N 6,8-dichloro-2-cyclopropyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C2CC2)CC1C1=CC=CC=C1 WOSRCHOJUSCXJV-UHFFFAOYSA-N 0.000 claims description 6
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
XMYPFIYRTAOIFI-UHFFFAOYSA-N 2-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)aniline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1N XMYPFIYRTAOIFI-UHFFFAOYSA-N 0.000 claims description 5
ATZPMMXKZFAFOP-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)aniline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(N)C=C1 ATZPMMXKZFAFOP-UHFFFAOYSA-N 0.000 claims description 5
SNWGRRCTCGASCN-UHFFFAOYSA-N 4-nitro-1h-pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CN1 SNWGRRCTCGASCN-UHFFFAOYSA-N 0.000 claims description 5
XSGVEJDBLQQXST-UHFFFAOYSA-N 5-chloro-1,3-dimethylpyrazole-4-sulfonic acid Chemical class CC1=NN(C)C(Cl)=C1S(O)(=O)=O XSGVEJDBLQQXST-UHFFFAOYSA-N 0.000 claims description 5
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 5
229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
150000004702 methyl esters Chemical class 0.000 claims description 5
HWHOOFAFSRSPOT-UHFFFAOYSA-N 2-chloro-5-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(Cl)C(S(N)(=O)=O)=C1 HWHOOFAFSRSPOT-UHFFFAOYSA-N 0.000 claims description 4
LJCWTVCXFOSCRP-UHFFFAOYSA-N 4-(3-bromophenyl)-6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(Br)=C1 LJCWTVCXFOSCRP-UHFFFAOYSA-N 0.000 claims description 4
BYEHLECXGQISFM-UHFFFAOYSA-N 6,8-dichloro-2-methyl-4-(4-pyrrolidin-1-ylphenyl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1N1CCCC1 BYEHLECXGQISFM-UHFFFAOYSA-N 0.000 claims description 4
SHBPZIGBKLSQFG-UHFFFAOYSA-N 6,8-dichloro-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1 SHBPZIGBKLSQFG-UHFFFAOYSA-N 0.000 claims description 4
230000001154 acute effect Effects 0.000 claims description 4
230000004663 cell proliferation Effects 0.000 claims description 4
230000002093 peripheral effect Effects 0.000 claims description 4
230000000241 respiratory effect Effects 0.000 claims description 4
230000029058 respiratory gaseous exchange Effects 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
206010041235 Snoring Diseases 0.000 claims description 3
201000011040 acute kidney failure Diseases 0.000 claims description 3
208000020832 chronic kidney disease Diseases 0.000 claims description 3
AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 3
125000004494 ethyl ester group Chemical group 0.000 claims description 3
230000005764 inhibitory process Effects 0.000 claims description 3
230000004060 metabolic process Effects 0.000 claims description 3
201000002859 sleep apnea Diseases 0.000 claims description 3
ZTWFDFFSPSWCEP-UHFFFAOYSA-N 2,4-dimethyl-4-phenyl-1,3-dihydroisoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1(C)C1=CC=CC=C1 ZTWFDFFSPSWCEP-UHFFFAOYSA-N 0.000 claims description 2
ZBINDVNASLJSJF-UHFFFAOYSA-N 2,6-dimethyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(C)=CC=C2CN(C)CC1C1=CC=CC=C1 ZBINDVNASLJSJF-UHFFFAOYSA-N 0.000 claims description 2
SUYOCKAQLJWIGF-UHFFFAOYSA-N 2,8-dimethyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(C)=C2CN(C)CC1C1=CC=CC=C1 SUYOCKAQLJWIGF-UHFFFAOYSA-N 0.000 claims description 2
SCROJUWBHGENKF-UHFFFAOYSA-N 2-butyl-4-phenyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C12=CC=CC(N)=C2CN(CCCC)CC1C1=CC=CC=C1 SCROJUWBHGENKF-UHFFFAOYSA-N 0.000 claims description 2
QKUVNSGJPHVOHY-UHFFFAOYSA-N 2-ethyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(CC)CC1C1=CC=CC=C1 QKUVNSGJPHVOHY-UHFFFAOYSA-N 0.000 claims description 2
NNVATDBGKYTMIL-UHFFFAOYSA-N 2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=CC=C1 NNVATDBGKYTMIL-UHFFFAOYSA-N 0.000 claims description 2
ZZYPDSKOTDXNJI-UHFFFAOYSA-N 2-methyl-8-nitro-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC([N+]([O-])=O)=C2CN(C)CC1C1=CC=CC=C1 ZZYPDSKOTDXNJI-UHFFFAOYSA-N 0.000 claims description 2
WALQZRTZISWWJK-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=C(Cl)C=C1Cl WALQZRTZISWWJK-UHFFFAOYSA-N 0.000 claims description 2
IRZHQDDIUQJKJQ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=C(Cl)C(Cl)=C1 IRZHQDDIUQJKJQ-UHFFFAOYSA-N 0.000 claims description 2
YPCPHQRYILZBJY-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(Cl)C(Cl)=C1 YPCPHQRYILZBJY-UHFFFAOYSA-N 0.000 claims description 2
IWCPITVSHIVSOX-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC(Cl)=C1 IWCPITVSHIVSOX-UHFFFAOYSA-N 0.000 claims description 2
ODIYTWXTFQEXKZ-UHFFFAOYSA-N 4-(8-amino-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzene-1,2-diol Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=C(O)C(O)=C1 ODIYTWXTFQEXKZ-UHFFFAOYSA-N 0.000 claims description 2
LMZGHKOXTNBVJV-UHFFFAOYSA-N 5,6-dichloro-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC(Cl)=C(Cl)C2=C1CN(C)CC2C1=CC=CC=C1 LMZGHKOXTNBVJV-UHFFFAOYSA-N 0.000 claims description 2
OFEGITGLTYCZKZ-UHFFFAOYSA-N 5,8-dichloro-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=C(Cl)C=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1 OFEGITGLTYCZKZ-UHFFFAOYSA-N 0.000 claims description 2
DOGUAYAXSQVEBS-UHFFFAOYSA-N 5-(8-amino-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C1C2=CC=CC(N)=C2CN(C)C1 DOGUAYAXSQVEBS-UHFFFAOYSA-N 0.000 claims description 2
KCAPDRPOFJFNBM-UHFFFAOYSA-N 6,7-dichloro-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=C(Cl)C=C2CN(C)CC1C1=CC=CC=C1 KCAPDRPOFJFNBM-UHFFFAOYSA-N 0.000 claims description 2
HJPBWJPDZBZIBF-UHFFFAOYSA-N 6,8-dichloro-2-ethyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(CC)CC1C1=CC=CC=C1 HJPBWJPDZBZIBF-UHFFFAOYSA-N 0.000 claims description 2
MQKVNEREAGDEFV-UHFFFAOYSA-N 6,8-dichloro-2-methyl-4-(4-methylphenyl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(C)C=C1 MQKVNEREAGDEFV-UHFFFAOYSA-N 0.000 claims description 2
LOVQZNURWACHBM-UHFFFAOYSA-N 6,8-dichloro-4-(4-chlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(Cl)C=C1 LOVQZNURWACHBM-UHFFFAOYSA-N 0.000 claims description 2
LQKVSIAEMCZTBA-UHFFFAOYSA-N 6,8-dichloro-4-(4-fluorophenyl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(F)C=C1 LQKVSIAEMCZTBA-UHFFFAOYSA-N 0.000 claims description 2
SMNDOAOGUPEWHX-UHFFFAOYSA-N 6,8-dichloro-4-phenyl-2-propan-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C(C)C)CC1C1=CC=CC=C1 SMNDOAOGUPEWHX-UHFFFAOYSA-N 0.000 claims description 2
FXSGMQJMMGOBJR-UHFFFAOYSA-N 7-chloro-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(Cl)C=C2CN(C)CC1C1=CC=CC=C1 FXSGMQJMMGOBJR-UHFFFAOYSA-N 0.000 claims description 2
IWTBQDAWZVFFLJ-UHFFFAOYSA-N 8-bromo-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(Br)=C2CN(C)CC1C1=CC=CC=C1 IWTBQDAWZVFFLJ-UHFFFAOYSA-N 0.000 claims description 2
PJIBWJPNKNAWGQ-UHFFFAOYSA-N 8-chloro-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1 PJIBWJPNKNAWGQ-UHFFFAOYSA-N 0.000 claims description 2
OBCHZURPAABPDI-UHFFFAOYSA-N 8-methoxy-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC=2C(OC)=CC=CC=2C1C1=CC=CC=C1 OBCHZURPAABPDI-UHFFFAOYSA-N 0.000 claims description 2
208000009304 Acute Kidney Injury Diseases 0.000 claims description 2
208000033626 Renal failure acute Diseases 0.000 claims description 2
208000012998 acute renal failure Diseases 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
210000003169 central nervous system Anatomy 0.000 claims description 2
244000078703 ectoparasite Species 0.000 claims description 2
XXPANQJNYNUNES-UHFFFAOYSA-N nomifensine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC=C1 XXPANQJNYNUNES-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 11
VHKMTORCXXPIFI-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrazole-4-carboxylic acid Chemical compound OC(=O)C=1C=NNC=1C(F)(F)F VHKMTORCXXPIFI-UHFFFAOYSA-N 0.000 claims 4
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 2
OSZMNJRKIPAVOS-UHFFFAOYSA-N 4-phenyl-1,2,3,4-tetrahydroisoquinoline Chemical class C1NCC2=CC=CC=C2C1C1=CC=CC=C1 OSZMNJRKIPAVOS-UHFFFAOYSA-N 0.000 claims 1
208000030090 Acute Disease Diseases 0.000 claims 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims 1
208000022831 chronic renal failure syndrome Diseases 0.000 claims 1
230000006870 function Effects 0.000 claims 1
230000003871 intestinal function Effects 0.000 claims 1
229940047889 isobutyramide Drugs 0.000 claims 1
SWGQYEFEIOSAID-UHFFFAOYSA-N n,4-dimethylpiperazine-1-carboxamide Chemical compound CNC(=O)N1CCN(C)CC1 SWGQYEFEIOSAID-UHFFFAOYSA-N 0.000 claims 1
210000001428 peripheral nervous system Anatomy 0.000 claims 1
238000004321 preservation Methods 0.000 claims 1
238000001356 surgical procedure Methods 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 9
206010028980 Neoplasm Diseases 0.000 abstract description 8
201000011510 cancer Diseases 0.000 abstract description 7
239000003795 chemical substances by application Substances 0.000 abstract description 6
206010012601 diabetes mellitus Diseases 0.000 abstract description 5
102000004895 Lipoproteins Human genes 0.000 abstract description 4
108090001030 Lipoproteins Proteins 0.000 abstract description 4
230000002475 laxative effect Effects 0.000 abstract description 3
210000002966 serum Anatomy 0.000 abstract description 3
206010048554 Endothelial dysfunction Diseases 0.000 abstract description 2
230000000879 anti-atherosclerotic effect Effects 0.000 abstract description 2
230000001413 cellular effect Effects 0.000 abstract description 2
201000001883 cholelithiasis Diseases 0.000 abstract description 2
230000008694 endothelial dysfunction Effects 0.000 abstract description 2
230000003176 fibrotic effect Effects 0.000 abstract description 2
208000001130 gallstones Diseases 0.000 abstract description 2
206010020718 hyperplasia Diseases 0.000 abstract description 2
239000008141 laxative Substances 0.000 abstract description 2
210000000653 nervous system Anatomy 0.000 abstract description 2
102000052126 Sodium-Hydrogen Exchangers Human genes 0.000 abstract 1
108091006672 Sodium–hydrogen antiporter Proteins 0.000 abstract 1
230000004075 alteration Effects 0.000 abstract 1
229940030600 antihypertensive agent Drugs 0.000 abstract 1
239000002220 antihypertensive agent Substances 0.000 abstract 1
210000004556 brain Anatomy 0.000 abstract 1
244000045947 parasite Species 0.000 abstract 1
238000011321 prophylaxis Methods 0.000 abstract 1
230000004202 respiratory function Effects 0.000 abstract 1
230000008961 swelling Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
239000000243 solution Substances 0.000 description 97
238000000034 method Methods 0.000 description 70
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 59
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 56
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
239000002904 solvent Substances 0.000 description 51
239000013067 intermediate product Substances 0.000 description 49
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
239000012074 organic phase Substances 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
229910052943 magnesium sulfate Inorganic materials 0.000 description 30
235000019341 magnesium sulphate Nutrition 0.000 description 30
239000012071 phase Substances 0.000 description 30
238000003756 stirring Methods 0.000 description 30
239000000203 mixture Substances 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
238000000746 purification Methods 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 26
238000002953 preparative HPLC Methods 0.000 description 26
235000013877 carbamide Nutrition 0.000 description 25
239000000047 product Substances 0.000 description 23
239000012043 crude product Substances 0.000 description 21
235000010469 Glycine max Nutrition 0.000 description 20
238000012545 processing Methods 0.000 description 20
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 19
239000011734 sodium Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
241000159610 Roya <green alga> Species 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
241000566113 Branta sandvicensis Species 0.000 description 17
239000008346 aqueous phase Substances 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
239000007787 solid Substances 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
208000037516 chromosome inversion disease Diseases 0.000 description 15
229910052754 neon Inorganic materials 0.000 description 15
229910052720 vanadium Inorganic materials 0.000 description 15
108020004414 DNA Proteins 0.000 description 14
HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 13
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 13
239000012047 saturated solution Substances 0.000 description 13
239000007858 starting material Substances 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 12
230000009471 action Effects 0.000 description 12
150000002500 ions Chemical class 0.000 description 12
235000015854 Heliotropium curassavicum Nutrition 0.000 description 11
244000301682 Heliotropium curassavicum Species 0.000 description 11
235000013405 beer Nutrition 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
239000000126 substance Substances 0.000 description 11
244000068988 Glycine max Species 0.000 description 10
240000000220 Panda oleosa Species 0.000 description 10
235000016496 Panda oleosa Nutrition 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 10
235000006732 Torreya nucifera Nutrition 0.000 description 10
244000111306 Torreya nucifera Species 0.000 description 10
238000001035 drying Methods 0.000 description 10
238000004108 freeze drying Methods 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
238000012360 testing method Methods 0.000 description 10
101500020117 Aedes aegypti Sialokinin Proteins 0.000 description 9
235000008331 Pinus X rigitaeda Nutrition 0.000 description 9
235000011613 Pinus brutia Nutrition 0.000 description 9
241000018646 Pinus brutia Species 0.000 description 9
210000004369 blood Anatomy 0.000 description 9
239000008280 blood Substances 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
210000001508 eye Anatomy 0.000 description 9
240000007154 Coffea arabica Species 0.000 description 8
241000283965 Ochotona princeps Species 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
206010041349 Somnolence Diseases 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
239000000872 buffer Substances 0.000 description 8
235000016213 coffee Nutrition 0.000 description 8
235000013353 coffee beverage Nutrition 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 7
GUJXWKXDISDARD-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=C(Cl)C=C1Cl GUJXWKXDISDARD-UHFFFAOYSA-N 0.000 description 7
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
241000283725 Bos Species 0.000 description 7
VQUJECICMKGUIA-UHFFFAOYSA-N Cl.[N+](=O)([O-])C1=CC=C(C=C1)OC1=CC=C(C=C1)[N+](=O)[O-] Chemical compound Cl.[N+](=O)([O-])C1=CC=C(C=C1)OC1=CC=C(C=C1)[N+](=O)[O-] VQUJECICMKGUIA-UHFFFAOYSA-N 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
239000012300 argon atmosphere Substances 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
239000000284 extract Substances 0.000 description 7
235000013305 food Nutrition 0.000 description 7
235000011389 fruit/vegetable juice Nutrition 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
229910052727 yttrium Inorganic materials 0.000 description 7
MWAGUKZCDDRDCS-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 MWAGUKZCDDRDCS-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 6
230000005526 G1 to G0 transition Effects 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 6
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 6
235000009337 Spinacia oleracea Nutrition 0.000 description 6
244000300264 Spinacia oleracea Species 0.000 description 6
229910052770 Uranium Inorganic materials 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
229940079593 drug Drugs 0.000 description 6
HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000007429 general method Methods 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
244000145841 kine Species 0.000 description 6
238000011084 recovery Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
230000009466 transformation Effects 0.000 description 6
210000003462 vein Anatomy 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
241000282326 Felis catus Species 0.000 description 5
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
241000282320 Panthera leo Species 0.000 description 5
241001424341 Tara spinosa Species 0.000 description 5
206010000496 acne Diseases 0.000 description 5
235000013339 cereals Nutrition 0.000 description 5
239000008103 glucose Substances 0.000 description 5
235000001727 glucose Nutrition 0.000 description 5
239000005457 ice water Substances 0.000 description 5
208000014674 injury Diseases 0.000 description 5
230000003993 interaction Effects 0.000 description 5
230000001404 mediated effect Effects 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000011435 rock Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-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
FYJORSKXVAOJFZ-UHFFFAOYSA-N 4-methylpiperazine-1-carboxamide Chemical compound CN1CCN(C(N)=O)CC1 FYJORSKXVAOJFZ-UHFFFAOYSA-N 0.000 description 4
IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
208000002874 Acne Vulgaris Diseases 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
201000001320 Atherosclerosis Diseases 0.000 description 4
101000616562 Danio rerio Sonic hedgehog protein A Proteins 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
241000009328 Perro Species 0.000 description 4
241000549435 Pria Species 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
101100209990 Rattus norvegicus Slc18a2 gene Proteins 0.000 description 4
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 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
241001415849 Strigiformes Species 0.000 description 4
GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 4
229940088623 biologically active substance Drugs 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
244000309464 bull Species 0.000 description 4
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 4
239000000969 carrier Substances 0.000 description 4
235000013351 cheese Nutrition 0.000 description 4
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
KEBHLNDPKPIPLI-UHFFFAOYSA-N hydron;2-(3h-inden-4-yloxymethyl)morpholine;chloride Chemical compound Cl.C=1C=CC=2C=CCC=2C=1OCC1CNCCO1 KEBHLNDPKPIPLI-UHFFFAOYSA-N 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
210000002445 nipple Anatomy 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical class BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 4
XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
235000013616 tea Nutrition 0.000 description 4
OGCUAECIKFVXQG-UHFFFAOYSA-N 2-(2,4-difluorophenyl)ethanamine Chemical compound NCCC1=CC=C(F)C=C1F OGCUAECIKFVXQG-UHFFFAOYSA-N 0.000 description 3
CHZPJUSFUDUEMZ-UHFFFAOYSA-N 3-acetylbenzoic acid Chemical compound CC(=O)C1=CC=CC(C(O)=O)=C1 CHZPJUSFUDUEMZ-UHFFFAOYSA-N 0.000 description 3
235000007119 Ananas comosus Nutrition 0.000 description 3
244000099147 Ananas comosus Species 0.000 description 3
241000486634 Bena Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
235000009025 Carya illinoensis Nutrition 0.000 description 3
244000068645 Carya illinoensis Species 0.000 description 3
241000283153 Cetacea Species 0.000 description 3
241000254173 Coleoptera Species 0.000 description 3
101150105088 Dele1 gene Proteins 0.000 description 3
241001649081 Dina Species 0.000 description 3
241000283074 Equus asinus Species 0.000 description 3
241000975394 Evechinus chloroticus Species 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
206010020772 Hypertension Diseases 0.000 description 3
206010021143 Hypoxia Diseases 0.000 description 3
101100237844 Mus musculus Mmp19 gene Proteins 0.000 description 3
GMEHFXXZSWDEDB-UHFFFAOYSA-N N-ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 description 3
101001098066 Naja melanoleuca Basic phospholipase A2 1 Proteins 0.000 description 3
208000002193 Pain Diseases 0.000 description 3
241001659863 Panna Species 0.000 description 3
241001387976 Pera Species 0.000 description 3
241000269435 Rana <genus> Species 0.000 description 3
241000022563 Rema Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241001575049 Sonia Species 0.000 description 3
244000269722 Thea sinensis Species 0.000 description 3
MZZINWWGSYUHGU-UHFFFAOYSA-J ToTo-1 Chemical compound [I-].[I-].[I-].[I-].C12=CC=CC=C2C(C=C2N(C3=CC=CC=C3S2)C)=CC=[N+]1CCC[N+](C)(C)CCC[N+](C)(C)CCC[N+](C1=CC=CC=C11)=CC=C1C=C1N(C)C2=CC=CC=C2S1 MZZINWWGSYUHGU-UHFFFAOYSA-J 0.000 description 3
241001377938 Yara Species 0.000 description 3
AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 3
239000002956 ash Substances 0.000 description 3
230000003143 atherosclerotic effect Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
230000008859 change Effects 0.000 description 3
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
208000031513 cyst Diseases 0.000 description 3
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 3
UMYZHWLYICNGRQ-UHFFFAOYSA-N ethanol;heptane Chemical compound CCO.CCCCCCC UMYZHWLYICNGRQ-UHFFFAOYSA-N 0.000 description 3
238000007710 freezing Methods 0.000 description 3
230000008014 freezing Effects 0.000 description 3
239000011521 glass Substances 0.000 description 3
235000012907 honey Nutrition 0.000 description 3
208000028867 ischemia Diseases 0.000 description 3
USJUUYYGHABIBU-UHFFFAOYSA-N methanesulfonamide;hydrochloride Chemical compound Cl.CS(N)(=O)=O USJUUYYGHABIBU-UHFFFAOYSA-N 0.000 description 3
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 3
208000010125 myocardial infarction Diseases 0.000 description 3
230000036407 pain Effects 0.000 description 3
229920000767 polyaniline Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002243 precursor Substances 0.000 description 3
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
230000007017 scission Effects 0.000 description 3
235000011888 snacks Nutrition 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000007921 spray Substances 0.000 description 3
150000003526 tetrahydroisoquinolines Chemical class 0.000 description 3
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-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
OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 2
XFXSJOHJDZJFCP-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)ethanamine Chemical compound CS(=O)(=O)C1=CC=C(CCN)C=C1 XFXSJOHJDZJFCP-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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 2
NZRDKNBIPVLNHA-UHFFFAOYSA-N 5-Acetylsalicylic acid Chemical compound CC(=O)C1=CC=C(O)C(C(O)=O)=C1 NZRDKNBIPVLNHA-UHFFFAOYSA-N 0.000 description 2
LDBYWWIOZYWOLG-UHFFFAOYSA-N 6,8-dichloro-2-cyclopropyl-4-phenyl-3,4-dihydro-1h-isoquinoline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC(Cl)=CC(Cl)=C2CN(C2CC2)CC1C1=CC=CC=C1 LDBYWWIOZYWOLG-UHFFFAOYSA-N 0.000 description 2
LAXMGXGWGIBHHT-UHFFFAOYSA-N 6,8-dichloro-2-methyl-4-(4-piperidin-1-ylphenyl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1N1CCCCC1 LAXMGXGWGIBHHT-UHFFFAOYSA-N 0.000 description 2
241000208140 Acer Species 0.000 description 2
241001143500 Aceraceae Species 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
102000009346 Adenosine receptors Human genes 0.000 description 2
108050000203 Adenosine receptors Proteins 0.000 description 2
241001136792 Alle Species 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
206010003402 Arthropod sting Diseases 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
241000282461 Canis lupus Species 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
241000283707 Capra Species 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000511343 Chondrostoma nasus Species 0.000 description 2
241001342895 Chorus Species 0.000 description 2
235000003913 Coccoloba uvifera Nutrition 0.000 description 2
244000241257 Cucumis melo Species 0.000 description 2
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
206010011732 Cyst Diseases 0.000 description 2
206010011906 Death Diseases 0.000 description 2
235000005459 Digitaria exilis Nutrition 0.000 description 2
101100460157 Drosophila melanogaster nenya gene Proteins 0.000 description 2
208000007530 Essential hypertension Diseases 0.000 description 2
RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 2
241000755093 Gaidropsarus vulgaris Species 0.000 description 2
241000581652 Hagenia abyssinica Species 0.000 description 2
101000850431 Homo sapiens Synaptic vesicle membrane protein VAT-1 homolog Proteins 0.000 description 2
101000964584 Homo sapiens Zinc finger protein 160 Proteins 0.000 description 2
244000025221 Humulus lupulus Species 0.000 description 2
241000764773 Inna Species 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
235000004431 Linum usitatissimum Nutrition 0.000 description 2
240000006240 Linum usitatissimum Species 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
241001291562 Martes pennanti Species 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
101100042271 Mus musculus Sema3b gene Proteins 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
101000867030 Myxine glutinosa Homeobox protein engrailed-like B Proteins 0.000 description 2
241000750004 Nestor meridionalis Species 0.000 description 2
101800001775 Nuclear inclusion protein A Proteins 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
101150034459 Parpbp gene Proteins 0.000 description 2
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
241001377010 Pila Species 0.000 description 2
240000005546 Piper methysticum Species 0.000 description 2
235000016787 Piper methysticum Nutrition 0.000 description 2
208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
240000008976 Pterocarpus marsupium Species 0.000 description 2
244000046146 Pueraria lobata Species 0.000 description 2
235000010575 Pueraria lobata Nutrition 0.000 description 2
240000001987 Pyrus communis Species 0.000 description 2
208000004756 Respiratory Insufficiency Diseases 0.000 description 2
235000011449 Rosa Nutrition 0.000 description 2
235000014548 Rubus moluccanus Nutrition 0.000 description 2
235000003976 Ruta Nutrition 0.000 description 2
240000005746 Ruta graveolens Species 0.000 description 2
235000012377 Salvia columbariae var. columbariae Nutrition 0.000 description 2
240000005481 Salvia hispanica Species 0.000 description 2
235000001498 Salvia hispanica Nutrition 0.000 description 2
208000006011 Stroke Diseases 0.000 description 2
241000282887 Suidae Species 0.000 description 2
102100033475 Synaptic vesicle membrane protein VAT-1 homolog Human genes 0.000 description 2
206010052428 Wound Diseases 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
102100040815 Zinc finger protein 160 Human genes 0.000 description 2
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 2
150000003869 acetamides Chemical class 0.000 description 2
NUQQCCGRQJCSEV-UHFFFAOYSA-N acetic acid;4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonamide Chemical compound CC(O)=O.C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(S(N)(=O)=O)C=C1 NUQQCCGRQJCSEV-UHFFFAOYSA-N 0.000 description 2
150000008062 acetophenones Chemical class 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000000556 agonist Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
OWCDMRFUFMERMZ-UHFFFAOYSA-N benzenesulfonamide;hydrochloride Chemical compound Cl.NS(=O)(=O)C1=CC=CC=C1 OWCDMRFUFMERMZ-UHFFFAOYSA-N 0.000 description 2
WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
150000003939 benzylamines Chemical class 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
210000004204 blood vessel Anatomy 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
235000014167 chia Nutrition 0.000 description 2
238000013375 chromatographic separation Methods 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
XAEWZDYWZHIUCT-UHFFFAOYSA-N desipramine hydrochloride Chemical compound [H+].[Cl-].C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 XAEWZDYWZHIUCT-UHFFFAOYSA-N 0.000 description 2
235000021186 dishes Nutrition 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
235000001159 dosh Nutrition 0.000 description 2
244000245171 dosh Species 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
239000006260 foam Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
210000004013 groin Anatomy 0.000 description 2
230000012010 growth Effects 0.000 description 2
210000003128 head Anatomy 0.000 description 2
230000007954 hypoxia Effects 0.000 description 2
230000003834 intracellular effect Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
238000002156 mixing Methods 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
235000013550 pizza Nutrition 0.000 description 2
235000021018 plums Nutrition 0.000 description 2
239000002574 poison Substances 0.000 description 2
231100000614 poison Toxicity 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
201000004193 respiratory failure Diseases 0.000 description 2
210000002345 respiratory system Anatomy 0.000 description 2
235000005806 ruta Nutrition 0.000 description 2
TUXCLJQCYVCGDW-UHFFFAOYSA-N sativan Chemical compound COC1=CC(OC)=CC=C1C1CC2=CC=C(O)C=C2OC1 TUXCLJQCYVCGDW-UHFFFAOYSA-N 0.000 description 2
239000013049 sediment Substances 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000004071 soot Substances 0.000 description 2
101150041594 soti gene Proteins 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
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 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
229910052721 tungsten Inorganic materials 0.000 description 2
230000001755 vocal effect Effects 0.000 description 2
238000004018 waxing Methods 0.000 description 2
210000002268 wool Anatomy 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
WLNBMPZUVDTASE-HXIISURNSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO WLNBMPZUVDTASE-HXIISURNSA-N 0.000 description 1
RLLPVAHGXHCWKJ-IEBWSBKVSA-N (3-phenoxyphenyl)methyl (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-IEBWSBKVSA-N 0.000 description 1
NAPPWIFDUAHTRY-XYDRQXHOSA-N (8r,9s,10r,13s,14s,17r)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 NAPPWIFDUAHTRY-XYDRQXHOSA-N 0.000 description 1
108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 description 1
FVUGZKDGWGKCFE-UHFFFAOYSA-N 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCCC2=C1CC(C(C)=O)(C)C(C)C2 FVUGZKDGWGKCFE-UHFFFAOYSA-N 0.000 description 1
WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
WGLUZJWOTTXZIC-UHFFFAOYSA-N 1-(bromomethyl)-2,4-dimethylbenzene Chemical compound CC1=CC=C(CBr)C(C)=C1 WGLUZJWOTTXZIC-UHFFFAOYSA-N 0.000 description 1
HGKPAXHJTMHWAH-UHFFFAOYSA-N 1-(bromomethyl)-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(CBr)C=C1 HGKPAXHJTMHWAH-UHFFFAOYSA-N 0.000 description 1
PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 1
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 1
WCGPCBACLBHDCI-UHFFFAOYSA-N 2,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C(F)=C1 WCGPCBACLBHDCI-UHFFFAOYSA-N 0.000 description 1
VQGZTRKXOUWMAC-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)ethanamine Chemical compound CC1=CC=C(CCN)C(C)=C1 VQGZTRKXOUWMAC-UHFFFAOYSA-N 0.000 description 1
GYYRSYUPFKJPRT-UHFFFAOYSA-N 2-(4-bromo-2-chlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Br)C=C1Cl GYYRSYUPFKJPRT-UHFFFAOYSA-N 0.000 description 1
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 1
SHWIBSLBAOBAFU-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.CN(C)CCOCCN(C)C SHWIBSLBAOBAFU-UHFFFAOYSA-N 0.000 description 1
HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
KNVRBEGQERGQRP-UHFFFAOYSA-N 2-amino-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CN KNVRBEGQERGQRP-UHFFFAOYSA-N 0.000 description 1
MZBXSQBQPJWECM-UHFFFAOYSA-N 2-bromo-1-(3-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=CC(Br)=C1 MZBXSQBQPJWECM-UHFFFAOYSA-N 0.000 description 1
FKJSFKCZZIXQIP-UHFFFAOYSA-N 2-bromo-1-(4-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=C(Br)C=C1 FKJSFKCZZIXQIP-UHFFFAOYSA-N 0.000 description 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
WVCHIGAIXREVNS-UHFFFAOYSA-N 2-hydroxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(O)=CC(=O)C(=O)C2=C1 WVCHIGAIXREVNS-UHFFFAOYSA-N 0.000 description 1
239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
GICIECWTEWJCRE-UHFFFAOYSA-N 3,4,4,7-tetramethyl-2,3-dihydro-1h-naphthalene Chemical compound CC1=CC=C2C(C)(C)C(C)CCC2=C1 GICIECWTEWJCRE-UHFFFAOYSA-N 0.000 description 1
QKEFOVJZNPELQH-UHFFFAOYSA-N 3-(2-bromoacetyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)CBr)=C1 QKEFOVJZNPELQH-UHFFFAOYSA-N 0.000 description 1
GRNHLFULJDXJKR-UHFFFAOYSA-N 3-(2-sulfanylethyl)-1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)NC2=C1 GRNHLFULJDXJKR-UHFFFAOYSA-N 0.000 description 1
SBCFGFDAZCTSRH-UHFFFAOYSA-N 3-acetylbenzonitrile Chemical compound CC(=O)C1=CC=CC(C#N)=C1 SBCFGFDAZCTSRH-UHFFFAOYSA-N 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
JOFJQVFBXUBXGM-UHFFFAOYSA-N 4-(4-bromophenyl)-6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(Br)C=C1 JOFJQVFBXUBXGM-UHFFFAOYSA-N 0.000 description 1
OPKTYGMCIDQTHP-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-n-propylbenzamide Chemical compound C1=CC(C(=O)NCCC)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 OPKTYGMCIDQTHP-UHFFFAOYSA-N 0.000 description 1
BDDRCLQZCBSWQN-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonamide;hydrochloride Chemical compound Cl.C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(S(N)(=O)=O)C=C1 BDDRCLQZCBSWQN-UHFFFAOYSA-N 0.000 description 1
NIEVPMJEVHSEIJ-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonyl chloride Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(S(Cl)(=O)=O)C=C1 NIEVPMJEVHSEIJ-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
DYPSDTOQOSPYOT-UHFFFAOYSA-N 4-bromo-1-(bromomethyl)-2-chlorobenzene Chemical compound ClC1=CC(Br)=CC=C1CBr DYPSDTOQOSPYOT-UHFFFAOYSA-N 0.000 description 1
MWZTVLNYXAKUKY-LBEKAKSKSA-N 4-hydroxy-N-[2-[(1R,13S)-3-methyl-8-oxo-11-azatetracyclo[8.4.0.01,13.02,7]tetradeca-2,4,6,9-tetraene-11-carbonyl]imidazo[1,2-a]pyridin-6-yl]benzamide Chemical compound C=1([C@]23C[C@@H]3C3)C(C)=CC=CC=1C(=O)C=C2N3C(=O)C(N=C1C=C2)=CN1C=C2NC(=O)C1=CC=C(O)C=C1 MWZTVLNYXAKUKY-LBEKAKSKSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
ZNQDTUOXQKYMEX-UHFFFAOYSA-N 6,8-dichloro-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1 ZNQDTUOXQKYMEX-UHFFFAOYSA-N 0.000 description 1
BZTDTCNHAFUJOG-UHFFFAOYSA-N 6-carboxyfluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C11OC(=O)C2=CC=C(C(=O)O)C=C21 BZTDTCNHAFUJOG-UHFFFAOYSA-N 0.000 description 1
BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
241001290610 Abildgaardia Species 0.000 description 1
244000144619 Abrus precatorius Species 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
240000005020 Acaciella glauca Species 0.000 description 1
208000010444 Acidosis Diseases 0.000 description 1
241000881711 Acipenser sturio Species 0.000 description 1
208000003200 Adenoma Diseases 0.000 description 1
206010001233 Adenoma benign Diseases 0.000 description 1
102100040439 Adenylate kinase 4, mitochondrial Human genes 0.000 description 1
108050004095 Adenylate kinase 4, mitochondrial Proteins 0.000 description 1
102100022958 Adenylate kinase 7 Human genes 0.000 description 1
108050000848 Adenylate kinase 7 Proteins 0.000 description 1
235000001674 Agaricus brunnescens Nutrition 0.000 description 1
240000000489 Agave utahensis Species 0.000 description 1
108010088751 Albumins Proteins 0.000 description 1
102000009027 Albumins Human genes 0.000 description 1
241001116389 Aloe Species 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
241001233887 Ania Species 0.000 description 1
241000272814 Anser sp. Species 0.000 description 1
240000003291 Armoracia rusticana Species 0.000 description 1
206010003225 Arteriospasm coronary Diseases 0.000 description 1
241000271566 Aves Species 0.000 description 1
235000017491 Bambusa tulda Nutrition 0.000 description 1
244000218454 Bambusa tulda Species 0.000 description 1
241001658044 Beata Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000167854 Bourreria succulenta Species 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
206010048962 Brain oedema Diseases 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000011293 Brassica napus Nutrition 0.000 description 1
235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
101100310222 Caenorhabditis briggsae she-1 gene Proteins 0.000 description 1
101100495769 Caenorhabditis elegans che-1 gene Proteins 0.000 description 1
101100388509 Caenorhabditis elegans che-3 gene Proteins 0.000 description 1
101100172628 Caenorhabditis elegans eri-1 gene Proteins 0.000 description 1
101100421668 Caenorhabditis elegans slo-1 gene Proteins 0.000 description 1
101100311260 Caenorhabditis elegans sti-1 gene Proteins 0.000 description 1
101100314454 Caenorhabditis elegans tra-1 gene Proteins 0.000 description 1
241000272173 Calidris Species 0.000 description 1
241000282421 Canidae Species 0.000 description 1
229940122072 Carbonic anhydrase inhibitor Drugs 0.000 description 1
244000201986 Cassia tora Species 0.000 description 1
208000003417 Central Sleep Apnea Diseases 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
235000019743 Choline chloride Nutrition 0.000 description 1
206010056370 Congestive cardiomyopathy Diseases 0.000 description 1
206010010774 Constipation Diseases 0.000 description 1
235000004257 Cordia myxa Nutrition 0.000 description 1
244000157795 Cordia myxa Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
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 1
101100325645 Danio rerio aurkb gene Proteins 0.000 description 1
101100421144 Danio rerio selenoo1 gene Proteins 0.000 description 1
101100256884 Dictyostelium discoideum shkE gene Proteins 0.000 description 1
201000010046 Dilated cardiomyopathy Diseases 0.000 description 1
235000017274 Diospyros sandwicensis Nutrition 0.000 description 1
241001050985 Disco Species 0.000 description 1
101100285518 Drosophila melanogaster how gene Proteins 0.000 description 1
101100453960 Drosophila melanogaster klar gene Proteins 0.000 description 1
101100507451 Drosophila melanogaster sip3 gene Proteins 0.000 description 1
235000009300 Ehretia acuminata Nutrition 0.000 description 1
244000046038 Ehretia acuminata Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000283086 Equidae Species 0.000 description 1
235000002757 Erythrina edulis Nutrition 0.000 description 1
240000008187 Erythrina edulis Species 0.000 description 1
101100501444 Escherichia phage P1 17 gene Proteins 0.000 description 1
UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
IWNWLPUNKAYUAW-UHFFFAOYSA-N Ethylendiamine dihydroiodide Chemical compound I.I.NCCN IWNWLPUNKAYUAW-UHFFFAOYSA-N 0.000 description 1
208000010201 Exanthema Diseases 0.000 description 1
101150096839 Fcmr gene Proteins 0.000 description 1
235000008730 Ficus carica Nutrition 0.000 description 1
244000025361 Ficus carica Species 0.000 description 1
206010016717 Fistula Diseases 0.000 description 1
235000002918 Fraxinus excelsior Nutrition 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
244000287680 Garcinia dulcis Species 0.000 description 1
241001547860 Gaya Species 0.000 description 1
241000288140 Gruiformes Species 0.000 description 1
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000825469 Haemulon vittatum Species 0.000 description 1
101001126084 Homo sapiens Piwi-like protein 2 Proteins 0.000 description 1
101000880116 Homo sapiens SERTA domain-containing protein 2 Proteins 0.000 description 1
101000702691 Homo sapiens Zinc finger protein SNAI1 Proteins 0.000 description 1
235000008694 Humulus lupulus Nutrition 0.000 description 1
206010020591 Hypercapnia Diseases 0.000 description 1
208000031226 Hyperlipidaemia Diseases 0.000 description 1
206010021137 Hypovolaemia Diseases 0.000 description 1
208000004356 Hysteria Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
241001397173 Kali <angiosperm> Species 0.000 description 1
241001026509 Kata Species 0.000 description 1
206010023421 Kidney fibrosis Diseases 0.000 description 1
241001417512 Kyphosidae Species 0.000 description 1
241000282838 Lama Species 0.000 description 1
244000208060 Lawsonia inermis Species 0.000 description 1
206010051602 Laziness Diseases 0.000 description 1
208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 1
241000234435 Lilium Species 0.000 description 1
229940110339 Long-acting muscarinic antagonist Drugs 0.000 description 1
208000019693 Lung disease Diseases 0.000 description 1
241001124569 Lycaenidae Species 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
240000002129 Malva sylvestris Species 0.000 description 1
235000006770 Malva sylvestris Nutrition 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
101150087188 Mast1 gene Proteins 0.000 description 1
241001214257 Mene Species 0.000 description 1
206010027417 Metabolic acidosis Diseases 0.000 description 1
241000046866 Metula Species 0.000 description 1
241000751119 Mila <angiosperm> Species 0.000 description 1
244000131360 Morinda citrifolia Species 0.000 description 1
241001206439 Motya Species 0.000 description 1
101100202896 Mus musculus Selenoo gene Proteins 0.000 description 1
101100049053 Mus musculus Vash1 gene Proteins 0.000 description 1
240000005561 Musa balbisiana Species 0.000 description 1
235000018290 Musa x paradisiaca Nutrition 0.000 description 1
241000030927 Myomys Species 0.000 description 1
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
FUSGACRLAFQQRL-UHFFFAOYSA-N N-Ethyl-N-nitrosourea Chemical compound CCN(N=O)C(N)=O FUSGACRLAFQQRL-UHFFFAOYSA-N 0.000 description 1
SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
229940125652 NAMI Drugs 0.000 description 1
101000800755 Naja oxiana Alpha-elapitoxin-Nno2a Proteins 0.000 description 1
241001274216 Naso Species 0.000 description 1
241001318330 Nenia Species 0.000 description 1
241000013563 Neotis Species 0.000 description 1
241000771698 Nerada Species 0.000 description 1
208000007256 Nevus Diseases 0.000 description 1
GFRROZIJVHUSKZ-FXGMSQOLSA-N OS I Natural products C[C@@H]1O[C@@H](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](OC[C@@H](O)[C@@H](O)[C@@H](O)CO)[C@@H]2NC(=O)C)[C@H](O)[C@H](O)[C@H]1O GFRROZIJVHUSKZ-FXGMSQOLSA-N 0.000 description 1
241000545337 Odessia Species 0.000 description 1
102100027069 Odontogenic ameloblast-associated protein Human genes 0.000 description 1
101710091533 Odontogenic ameloblast-associated protein Proteins 0.000 description 1
241000207836 Olea <angiosperm> Species 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
101150102323 PDYN gene Proteins 0.000 description 1
241001559981 Palyas Species 0.000 description 1
241000282322 Panthera Species 0.000 description 1
241000282376 Panthera tigris Species 0.000 description 1
241000412626 Penetes Species 0.000 description 1
235000000857 Pentadesma butyracea Nutrition 0.000 description 1
240000002134 Pentadesma butyracea Species 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
241001442654 Percnon planissimum Species 0.000 description 1
102000017795 Perilipin-1 Human genes 0.000 description 1
108010067162 Perilipin-1 Proteins 0.000 description 1
241001520299 Phascolarctos cinereus Species 0.000 description 1
240000004760 Pimpinella anisum Species 0.000 description 1
235000008565 Pinus banksiana Nutrition 0.000 description 1
244000113943 Pinus sabiniana Species 0.000 description 1
235000006237 Pinus sabiniana Nutrition 0.000 description 1
241000920340 Pion Species 0.000 description 1
102100029365 Piwi-like protein 2 Human genes 0.000 description 1
241000514450 Podocarpus latifolius Species 0.000 description 1
241000143946 Pontia Species 0.000 description 1
241000183024 Populus tremula Species 0.000 description 1
244000088401 Pyrus pyrifolia Species 0.000 description 1
235000001630 Pyrus pyrifolia var culta Nutrition 0.000 description 1
241000219492 Quercus Species 0.000 description 1
101150069124 RAN1 gene Proteins 0.000 description 1
101000697856 Rattus norvegicus Bile acid-CoA:amino acid N-acyltransferase Proteins 0.000 description 1
101100451967 Rattus norvegicus Ephx1 gene Proteins 0.000 description 1
235000009411 Rheum rhabarbarum Nutrition 0.000 description 1
244000299790 Rheum rhabarbarum Species 0.000 description 1
241000220010 Rhode Species 0.000 description 1
241001620634 Roger Species 0.000 description 1
102100037351 SERTA domain-containing protein 2 Human genes 0.000 description 1
241000979389 Scherya Species 0.000 description 1
241000801924 Sena Species 0.000 description 1
229910004219 SiNi Inorganic materials 0.000 description 1
244000191761 Sida cordifolia Species 0.000 description 1
241000350393 Sinna Species 0.000 description 1
241000168254 Siro Species 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
240000003829 Sorghum propinquum Species 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
101000720079 Stichodactyla helianthus DELTA-stichotoxin-She4a Proteins 0.000 description 1
101000636833 Streptomyces fradiae 2-deoxystreptamine N-acetyl-D-glucosaminyltransferase Proteins 0.000 description 1
208000034972 Sudden Infant Death Diseases 0.000 description 1
206010042440 Sudden infant death syndrome Diseases 0.000 description 1
235000019486 Sunflower oil Nutrition 0.000 description 1
241000375392 Tana Species 0.000 description 1
241000120020 Tela Species 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
241000736892 Thujopsis dolabrata Species 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
208000037386 Typhoid Diseases 0.000 description 1
241001199012 Usta Species 0.000 description 1
244000277051 Vaccinium cereum Species 0.000 description 1
241000256856 Vespidae Species 0.000 description 1
241000700605 Viruses Species 0.000 description 1
235000013447 Xanthosoma atrovirens Nutrition 0.000 description 1
240000001781 Xanthosoma sagittifolium Species 0.000 description 1
101000577938 Xenopus laevis Midkine-B Proteins 0.000 description 1
101100020289 Xenopus laevis koza gene Proteins 0.000 description 1
101150052610 Yars1 gene Proteins 0.000 description 1
206010048232 Yawning Diseases 0.000 description 1
241001080519 Zera Species 0.000 description 1
208000020329 Zika virus infectious disease Diseases 0.000 description 1
102100030917 Zinc finger protein SNAI1 Human genes 0.000 description 1
241000079527 Ziziphus spina-christi Species 0.000 description 1
GYMWQLRSSDFGEQ-ADRAWKNSSA-N [(3e,8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.O/N=C/1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(OC(C)=O)C#C)[C@@H]4[C@@H]3CCC2=C\1 GYMWQLRSSDFGEQ-ADRAWKNSSA-N 0.000 description 1
YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical class C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 description 1
229960000571 acetazolamide Drugs 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000012190 activator Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
230000032683 aging Effects 0.000 description 1
229940083712 aldosterone antagonist Drugs 0.000 description 1
239000002170 aldosterone antagonist Substances 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
235000011399 aloe vera Nutrition 0.000 description 1
ZSBOMTDTBDDKMP-OAHLLOKOSA-N alogliptin Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZSBOMTDTBDDKMP-OAHLLOKOSA-N 0.000 description 1
PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
208000007502 anemia Diseases 0.000 description 1
238000002399 angioplasty Methods 0.000 description 1
229940127282 angiotensin receptor antagonist Drugs 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
230000002337 anti-port Effects 0.000 description 1
239000003416 antiarrhythmic agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
208000008784 apnea Diseases 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000036523 atherogenesis Effects 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
235000021167 banquet Nutrition 0.000 description 1
230000003796 beauty Effects 0.000 description 1
CJPQIRJHIZUAQP-MRXNPFEDSA-N benalaxyl-M Chemical compound CC=1C=CC=C(C)C=1N([C@H](C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-MRXNPFEDSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
LVKZSFMYNWRPJX-UHFFFAOYSA-N benzenearsonic acid Natural products O[As](O)(=O)C1=CC=CC=C1 LVKZSFMYNWRPJX-UHFFFAOYSA-N 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
150000005524 benzylchlorides Chemical class 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
208000006752 brain edema Diseases 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
244000309466 calf Species 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000003489 carbonate dehydratase inhibitor Substances 0.000 description 1
ZJRWDIJRKKXMNW-UHFFFAOYSA-N carbonic acid;cobalt Chemical compound [Co].OC(O)=O ZJRWDIJRKKXMNW-UHFFFAOYSA-N 0.000 description 1
230000001269 cardiogenic effect Effects 0.000 description 1
230000003293 cardioprotective effect Effects 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000001364 causal effect Effects 0.000 description 1
LTINZAODLRIQIX-FBXRGJNPSA-N cefpodoxime proxetil Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC)C(=O)OC(C)OC(=O)OC(C)C)C(=O)C(=N/OC)\C1=CSC(N)=N1 LTINZAODLRIQIX-FBXRGJNPSA-N 0.000 description 1
230000007248 cellular mechanism Effects 0.000 description 1
208000018747 cerebellar ataxia with neuropathy and bilateral vestibular areflexia syndrome Diseases 0.000 description 1
238000000451 chemical ionisation Methods 0.000 description 1
SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
229960003178 choline chloride Drugs 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
208000019425 cirrhosis of liver Diseases 0.000 description 1
AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 description 1
229910000001 cobalt(II) carbonate Inorganic materials 0.000 description 1
239000000571 coke Substances 0.000 description 1
238000004891 communication Methods 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
208000012839 conversion disease Diseases 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
230000002354 daily effect Effects 0.000 description 1
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HDRXZJPWHTXQRI-BHDTVMLSSA-N diltiazem hydrochloride Chemical compound [Cl-].C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CC[NH+](C)C)C2=CC=CC=C2S1 HDRXZJPWHTXQRI-BHDTVMLSSA-N 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000035622 drinking Effects 0.000 description 1
229940000406 drug candidate Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
239000008151 electrolyte solution Substances 0.000 description 1
229940021013 electrolyte solution Drugs 0.000 description 1
QTTMOCOWZLSYSV-QWAPEVOJSA-M equilin sodium sulfate Chemical compound [Na+].[O-]S(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 QTTMOCOWZLSYSV-QWAPEVOJSA-M 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
229940011871 estrogen Drugs 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
OZWSHPFNEYQJSN-UHFFFAOYSA-N ethyl 3-(2-bromoacetyl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C(=O)CBr)=C1 OZWSHPFNEYQJSN-UHFFFAOYSA-N 0.000 description 1
SHYIEDSDUINFSE-UHFFFAOYSA-N ethyl 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 SHYIEDSDUINFSE-UHFFFAOYSA-N 0.000 description 1
OUFLMGGBKDKXKJ-UHFFFAOYSA-N ethyl 5-(2-bromoacetyl)-2-hydroxybenzoate Chemical compound CCOC(=O)C1=CC(C(=O)CBr)=CC=C1O OUFLMGGBKDKXKJ-UHFFFAOYSA-N 0.000 description 1
VGKYNVLECUYQIL-UHFFFAOYSA-N ethyl 5-acetyl-2-hydroxybenzoate Chemical compound CCOC(=O)C1=CC(C(C)=O)=CC=C1O VGKYNVLECUYQIL-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
201000005884 exanthem Diseases 0.000 description 1
230000005284 excitation Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000000887 face Anatomy 0.000 description 1
201000003373 familial cold autoinflammatory syndrome 3 Diseases 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000021323 fish oil Nutrition 0.000 description 1
230000003890 fistula Effects 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
238000005242 forging Methods 0.000 description 1
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 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
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229960004198 guanidine Drugs 0.000 description 1
229960000789 guanidine hydrochloride Drugs 0.000 description 1
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
244000144980 herd Species 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229960002003 hydrochlorothiazide Drugs 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
208000020346 hyperlipoproteinemia Diseases 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
208000017482 infantile neuronal ceroid lipofuscinosis Diseases 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
208000028774 intestinal disease Diseases 0.000 description 1
230000012105 intracellular pH reduction Effects 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
239000008274 jelly Substances 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
239000003446 ligand Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
230000007774 longterm Effects 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
235000012245 magnesium oxide Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000027939 micturition Effects 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
201000003152 motion sickness Diseases 0.000 description 1
235000012459 muffins Nutrition 0.000 description 1
UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
ISNLISSGALOLGC-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC(Cl)=CC=C1CNC1CC1 ISNLISSGALOLGC-UHFFFAOYSA-N 0.000 description 1
201000008383 nephritis Diseases 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
235000017524 noni Nutrition 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
230000000474 nursing effect Effects 0.000 description 1
235000008935 nutritious Nutrition 0.000 description 1
230000000414 obstructive effect Effects 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
229940103456 oseni Drugs 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000005192 partition Methods 0.000 description 1
235000015927 pasta Nutrition 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000035778 pathophysiological process Effects 0.000 description 1
239000011049 pearl Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 1
YKWNDAOEJQMLGH-UHFFFAOYSA-N phenyl 2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)OC1=CC=CC=C1 YKWNDAOEJQMLGH-UHFFFAOYSA-N 0.000 description 1
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
235000021178 picnic Nutrition 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000011148 porous material Substances 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000009117 preventive therapy Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
208000037920 primary disease Diseases 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 1
201000004240 prostatic hypertrophy Diseases 0.000 description 1
239000011251 protective drug Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
MXRGZXBFSKSZPH-UHFFFAOYSA-N protheobromine Chemical compound O=C1N(CC(O)C)C(=O)N(C)C2=C1N(C)C=N2 MXRGZXBFSKSZPH-UHFFFAOYSA-N 0.000 description 1
208000005069 pulmonary fibrosis Diseases 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
206010037844 rash Diseases 0.000 description 1
230000008439 repair process Effects 0.000 description 1
230000010410 reperfusion Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
230000000894 saliuretic effect Effects 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
235000015067 sauces Nutrition 0.000 description 1
210000003786 sclera Anatomy 0.000 description 1
208000037921 secondary disease Diseases 0.000 description 1
229920006012 semi-aromatic polyamide Polymers 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
238000009958 sewing Methods 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
PEVNIEPIRVCPAW-UHFFFAOYSA-J sodium;1h-imidazole;methylsulfinylmethane;ruthenium(3+);tetrachloride Chemical compound [Na+].[Cl-].[Cl-].[Cl-].[Cl-].[Ru+3].CS(C)=O.C1=CNC=N1 PEVNIEPIRVCPAW-UHFFFAOYSA-J 0.000 description 1
HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
239000008279 sol Substances 0.000 description 1
229940061368 sonata Drugs 0.000 description 1
235000014347 soups Nutrition 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000011477 surgical intervention Methods 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
238000010257 thawing Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000012549 training Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
201000008297 typhoid fever Diseases 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000003466 welding Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
KGPGQDLTDHGEGT-JCIKCJKQSA-N zeven Chemical compound C=1C([C@@H]2C(=O)N[C@H](C(N[C@H](C3=CC(O)=C4)C(=O)NCCCN(C)C)=O)[C@H](O)C5=CC=C(C(=C5)Cl)OC=5C=C6C=C(C=5O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@H](O5)C(O)=O)NC(=O)CCCCCCCCC(C)C)OC5=CC=C(C=C5)C[C@@H]5C(=O)N[C@H](C(N[C@H]6C(=O)N2)=O)C=2C(Cl)=C(O)C=C(C=2)OC=2C(O)=CC=C(C=2)[C@H](C(N5)=O)NC)=CC=C(O)C=1C3=C4O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O KGPGQDLTDHGEGT-JCIKCJKQSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- 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
- A61P1/10—Laxatives
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- 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
- A61P11/16—Central respiratory analeptics
- 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
- 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
- A61P33/00—Antiparasitic agents
- 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
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

UA20040705310A 2001-12-05 2002-11-20 Substituted 4-tetrahydroquinolines, use thereof as medicament, a medicament containing them UA77042C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10159714		2001-12-05
PCT/EP2002/012990 WO2003048129A1 (de)	2001-12-05	2002-11-20	Substituierte 4-phenyltetrahydroisochinoline, verfahren zu ihrer herstellung, ihre verwendung als medikament, sowie sie enthaltendes medikament

Publications (1)

Publication Number	Publication Date
UA77042C2 true UA77042C2 (en)	2006-10-16

Family

ID=7708117

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20040705310A UA77042C2 (en)	2001-12-05	2002-11-20	Substituted 4-tetrahydroquinolines, use thereof as medicament, a medicament containing them

Country Status (33)

Country	Link
EP (1)	EP1453810B1 (sr)
JP (1)	JP4510457B2 (sr)
KR (1)	KR20050044724A (sr)
CN (1)	CN100497314C (sr)
AR (1)	AR037620A1 (sr)
AT (1)	ATE425968T1 (sr)
AU (1)	AU2002356689B2 (sr)
BR (1)	BR0214753A (sr)
CA (1)	CA2469385A1 (sr)
CO (1)	CO5580748A2 (sr)
DE (1)	DE50213372D1 (sr)
DK (1)	DK1453810T3 (sr)
EC (1)	ECSP045138A (sr)
ES (1)	ES2324528T3 (sr)
HR (1)	HRP20040507A2 (sr)
HU (1)	HUP0600854A2 (sr)
IL (1)	IL162316A0 (sr)
MA (1)	MA27147A1 (sr)
MX (1)	MXPA04005343A (sr)
MY (1)	MY157371A (sr)
NO (1)	NO326650B1 (sr)
NZ (1)	NZ533322A (sr)
OA (1)	OA12740A (sr)
PE (1)	PE20030726A1 (sr)
PL (1)	PL369313A1 (sr)
PT (1)	PT1453810E (sr)
RS (1)	RS48004A (sr)
RU (1)	RU2298003C2 (sr)
TN (1)	TNSN04100A1 (sr)
TW (1)	TWI281860B (sr)
UA (1)	UA77042C2 (sr)
WO (1)	WO2003048129A1 (sr)
ZA (1)	ZA200403711B (sr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10312963A1 (de) *	2003-03-24	2004-10-07	Aventis Pharma Deutschland Gmbh	Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament
TW200526626A (en)	2003-09-13	2005-08-16	Astrazeneca Ab	Chemical compounds
DE102004046492A1 (de) *	2004-09-23	2006-03-30	Sanofi-Aventis Deutschland Gmbh	Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament
US20060111393A1 (en) *	2004-11-22	2006-05-25	Molino Bruce F	4-Phenyl substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin
DE102005001411A1 (de) *	2005-01-12	2006-07-27	Sanofi-Aventis Deutschland Gmbh	Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament
ES2430569T3 (es)	2005-02-18	2013-11-21	Astrazeneca Ab	Compuestos antibacterianos derivados de piperidina
US20080269214A1 (en) *	2005-03-04	2008-10-30	Astrazeneca Ab	Pyrrole Derivatives as Dna Gyrase and Topoisomerase Inhibitors
DE102005044817A1 (de)	2005-09-20	2007-03-22	Sanofi-Aventis Deutschland Gmbh	Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament
DE102006012545A1 (de) *	2006-03-18	2007-09-27	Sanofi-Aventis	Substituierte 2-Amino-4-phenyl-dihydrochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament
US10543207B2 (en)	2008-12-31	2020-01-28	Ardelyx, Inc.	Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders
CN103819403B (zh) *	2008-12-31	2017-01-04	阿德利克斯公司	用于治疗与体液潴留或盐超负荷有关的病症和胃肠道病症的化合物和方法
WO2018129556A1 (en) *	2017-01-09	2018-07-12	Ardelyx, Inc.	Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders
ES2446971T3 (es)	2009-05-12	2014-03-11	Albany Molecular Research, Inc.	Tetrahidroisoquinolinas sustituidas con arilo, heteroarilo, y heterociclo y su uso
MX363056B (es) *	2012-08-21	2019-03-06	Ardelyx Inc	Compuestos y metodos para inhibir al antipuerto mediado por nhe en el tratamiento de trastornos asociados con la retencion de fluidos o la sobrecarga de sal y trastornos del tracto gastrointestinal.
CN105392483B (zh)	2013-04-12	2019-03-15	阿德利克斯公司	用于抑制磷酸盐转运的nhe3结合化合物和方法
CN103788084A (zh) *	2014-03-02	2014-05-14	湖南华腾制药有限公司	四氢异喹啉衍生物及其合成方法
WO2016013657A1 (ja)	2014-07-25	2016-01-28	大正製薬株式会社	ヘテロアリールで置換されたフェニルテトラヒドロイソキノリン化合物
JP6903923B2 (ja) *	2016-01-22	2021-07-14	大正製薬株式会社	ヘテロアリールで置換されたフェニルテトラヒドロイソキノリン化合物を有効成分として含有する医薬
EA201991676A1 (ru)	2017-01-09	2020-01-30	Арделикс, Инк.	Ингибиторы nhe-опосредованного антипорта
KR20240090875A (ko) *	2017-01-09	2024-06-21	알데릭스, 인코포레이티드	위장관 장애를 치료하는 데 유용한 화합물
IL303799A (en) *	2020-12-18	2023-08-01	Shanghai Jemincare Pharmaceuticals Co Ltd	TETRAHYDROISOQUINOLINE COMPOUND IN SUBSTITUTE BENZOHETROCYCLE

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19951702A1 (de) *	1999-10-27	2001-05-03	Aventis Pharma Gmbh	Verwendung von 2-Amino-3,4-dihydro-chinazolinen zur Herstellung eines Medikaments zur Behandlung oder Prophylaxe von durch ischämischen Zuständen bewirkten Krankheiten
CN100436420C (zh) *	1999-11-03	2008-11-26	Amr科技公司	4-苯基取代的四氢异喹啉及其用于制备药物的用途
DK1246806T3 (da) *	1999-11-03	2008-06-16	Amr Technology Inc	Aryl- og heteroarylsubstituerede tetrahydroisoquinoliner og anvendelse deraf til blokering af genoptagelse af norepinefrin, dopsmin og serotonin
EP1113007A1 (en) *	1999-12-24	2001-07-04	Pfizer Inc.	Tetrahydroisoquinoline compounds as estrogen agonists/antagonists
DE10019062A1 (de) *	2000-04-18	2001-10-25	Merck Patent Gmbh	2-Guanidino-4-aryl-chinazoline als NHE-3 Inhibitoren

2002
- 2002-11-20 DK DK02804183T patent/DK1453810T3/da active
- 2002-11-20 BR BR0214753-0A patent/BR0214753A/pt not_active IP Right Cessation
- 2002-11-20 EP EP02804183A patent/EP1453810B1/de not_active Expired - Lifetime
- 2002-11-20 AU AU2002356689A patent/AU2002356689B2/en not_active Ceased
- 2002-11-20 JP JP2003549321A patent/JP4510457B2/ja not_active Expired - Fee Related
- 2002-11-20 AT AT02804183T patent/ATE425968T1/de not_active IP Right Cessation
- 2002-11-20 NZ NZ533322A patent/NZ533322A/en unknown
- 2002-11-20 WO PCT/EP2002/012990 patent/WO2003048129A1/de not_active Ceased
- 2002-11-20 CN CNB028278879A patent/CN100497314C/zh not_active Expired - Fee Related
- 2002-11-20 KR KR1020047008697A patent/KR20050044724A/ko not_active Abandoned
- 2002-11-20 MX MXPA04005343A patent/MXPA04005343A/es active IP Right Grant
- 2002-11-20 ES ES02804183T patent/ES2324528T3/es not_active Expired - Lifetime
- 2002-11-20 HU HU0600854A patent/HUP0600854A2/hu unknown
- 2002-11-20 RU RU2004120295/04A patent/RU2298003C2/ru not_active IP Right Cessation
- 2002-11-20 IL IL16231602A patent/IL162316A0/xx unknown
- 2002-11-20 PT PT02804183T patent/PT1453810E/pt unknown
- 2002-11-20 CA CA002469385A patent/CA2469385A1/en not_active Abandoned
- 2002-11-20 RS YU48004A patent/RS48004A/sr unknown
- 2002-11-20 UA UA20040705310A patent/UA77042C2/uk unknown
- 2002-11-20 PL PL02369313A patent/PL369313A1/xx not_active Application Discontinuation
- 2002-11-20 HR HR20040507A patent/HRP20040507A2/hr not_active Application Discontinuation
- 2002-11-20 OA OA1200400166A patent/OA12740A/en unknown
- 2002-11-20 DE DE50213372T patent/DE50213372D1/de not_active Expired - Lifetime
- 2002-11-26 PE PE2002001138A patent/PE20030726A1/es not_active Application Discontinuation
- 2002-12-03 TW TW091134977A patent/TWI281860B/zh not_active IP Right Cessation
- 2002-12-03 AR ARP020104667A patent/AR037620A1/es unknown
- 2002-12-04 MY MYPI20024565A patent/MY157371A/en unknown
2004
- 2004-05-14 ZA ZA200403711A patent/ZA200403711B/en unknown
- 2004-05-21 MA MA27693A patent/MA27147A1/fr unknown
- 2004-05-25 NO NO20042158A patent/NO326650B1/no not_active IP Right Cessation
- 2004-06-03 CO CO04052088A patent/CO5580748A2/es not_active Application Discontinuation
- 2004-06-04 EC EC2004005138A patent/ECSP045138A/es unknown
- 2004-06-04 TN TNP2004000100A patent/TNSN04100A1/en unknown

Also Published As

Publication number	Publication date
AR037620A1 (es)	2004-11-17
JP2005515205A (ja)	2005-05-26
TNSN04100A1 (en)	2006-06-01
EP1453810A1 (de)	2004-09-08
RU2298003C2 (ru)	2007-04-27
HK1072597A1 (zh)	2005-09-02
DK1453810T3 (da)	2009-07-20
HRP20040507A2 (en)	2005-08-31
WO2003048129A1 (de)	2003-06-12
ATE425968T1 (de)	2009-04-15
ES2324528T3 (es)	2009-08-10
RU2004120295A (ru)	2006-01-10
EP1453810B1 (de)	2009-03-18
OA12740A (en)	2006-06-30
CO5580748A2 (es)	2005-11-30
MA27147A1 (fr)	2005-01-03
NO20042158L (no)	2004-08-27
CA2469385A1 (en)	2003-06-12
PT1453810E (pt)	2009-05-27
ECSP045138A (es)	2004-08-27
MY157371A (en)	2016-06-15
TW200306190A (en)	2003-11-16
MXPA04005343A (es)	2004-09-27
AU2002356689A1 (en)	2003-06-17
PL369313A1 (en)	2005-04-18
AU2002356689B2 (en)	2008-05-15
IL162316A0 (en)	2005-11-20
CN100497314C (zh)	2009-06-10
RS48004A (sr)	2006-10-27
BR0214753A (pt)	2004-12-14
KR20050044724A (ko)	2005-05-12
TWI281860B (en)	2007-06-01
PE20030726A1 (es)	2003-09-30
DE50213372D1 (de)	2009-04-30
NO326650B1 (no)	2009-01-26
NZ533322A (en)	2006-02-24
HUP0600854A2 (en)	2007-02-28
ZA200403711B (en)	2005-06-09
JP4510457B2 (ja)	2010-07-21
CN1617856A (zh)	2005-05-18

Publication	Publication Date	Title
UA126549C2 (uk)	2022-11-02	Композиція і спосіб для з'єднання позаклітинних доменів типу і та типу іі як гетерологічного химерного білка
Khalil-Manesh et al.	1993	Lead-induced hypertension: possible role of endothelial factors
UA129537C2 (uk)	2025-05-28	Сполука-коагоніст gip/glp1
HUE025013T2 (hu)	2016-04-28	Szulfonamid-származékok
UA129947C2 (uk)	2025-09-24	Спосіб застосування коагоніста gip/glp1 при діабеті
ES2750008T3 (es)	2020-03-24	Células madre mesenquimatosas modificadas genéticamente que expresan klotho
UA121662C2 (uk)	2020-07-10	Химерний інсектицидний білок, інгібіторний відносно лускокрилих шкідників
HU230380B1 (hu)	2016-03-29	N-Védett amino-hidroxi-adamantán-karbonsav és eljárás az előálllítására
UA121093C2 (uk)	2020-04-10	Конструкція, яка містить токсиген, що кодує пестицидний білок, і спосіб її застосування для знищення напівтвердокрилих шкідників
CN110381982B (zh)	2023-11-28	与myomixer促进的肌细胞融合相关的组合物和方法
HU230679B1 (en)	2017-08-28	Mammalian interleukin-12 p40 and interleukin b30, combinations thereof, antibodies, uses in pharmaceutical compositions
UA124734C2 (uk)	2021-11-10	Антитіло проти с5 і його застосування
UA126656C2 (uk)	2023-01-11	Біспецифічна конструкція антитіла до psma і cd3, яке залучають t-клітини
UA114173C2 (uk)	2017-05-10	Пристрій та спосіб для проведення проточної цитометрії
HUE031616T2 (hu)	2017-07-28	N1-pirazol-spiroketon acetil-koenzim-A karboxiláz inhibítorok
UA76887C2 (uk)	2006-09-15	Сполука піперидину
UA129793C2 (uk)	2025-08-06	Антитіло до фактора згортання xi
UA118866C2 (uk)	2019-03-25	Химерний білок сті
UA128281C2 (uk)	2024-05-29	Одержання маїсу, стійкого до північної плямистості листя
UA130716C2 (uk)	2026-04-29	Тонке картування і підтвердження локусу qtl, відповідального за ознаки вмісту волокон і кольору оболонки насіння, і ідентифікація маркерів snp для маркер-опосередкованого відбору на ці ознаки в лінії каноли з жовтою оболонкою насіння (ysc) yn01-429 і в її лінії диференціювання
McDougall Jr	2018	By Eastern windows: the story of a battle of souls and minds in the prison camps of Sumatra
Brown	1911	The Tamans of the Upper Chindwin, Burma
UA108224C2 (uk)	2015-04-10	Терапевтичні сполуки, які модулюють тирозинфосфатазу з підвищеним вмістом в смугастому тілі, і пов'язані з ними способи застосування
KR20260049582A (ko)	2026-04-14	약물의 제조에 있어서의 양성자 펌프 조절제의 용도
Stephen	0	British Columbia