SI3065738T1 - Compounds and procedures for modulating the farnesoid X receptors - Google Patents
Compounds and procedures for modulating the farnesoid X receptors Download PDFInfo
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- SI3065738T1 SI3065738T1 SI201430692T SI201430692T SI3065738T1 SI 3065738 T1 SI3065738 T1 SI 3065738T1 SI 201430692 T SI201430692 T SI 201430692T SI 201430692 T SI201430692 T SI 201430692T SI 3065738 T1 SI3065738 T1 SI 3065738T1
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- Prior art keywords
- methyl
- carboxamido
- pyrazole
- dihydrochromeno
- chloro
- Prior art date
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- 102100038495 Bile acid receptor Human genes 0.000 title claims abstract 8
- 238000000034 method Methods 0.000 title claims 2
- 239000000203 mixture Substances 0.000 title claims 2
- 101150027485 NR1H4 gene Proteins 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 54
- -1 pyrazole-3-carboxamido Chemical group 0.000 claims 44
- 239000005711 Benzoic acid Substances 0.000 claims 27
- 235000010233 benzoic acid Nutrition 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 23
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 12
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 230000001404 mediated effect Effects 0.000 claims 5
- 206010008635 Cholestasis Diseases 0.000 claims 4
- 230000007870 cholestasis Effects 0.000 claims 4
- 231100000359 cholestasis Toxicity 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 2
- VXCYSIHBMFKOEQ-UHFFFAOYSA-N 3-[[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2ccccc2F)c2COc3ccc(Cl)cc3-c12 VXCYSIHBMFKOEQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 206010025476 Malabsorption Diseases 0.000 claims 2
- 208000004155 Malabsorption Syndromes Diseases 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 208000012347 Parenteral nutrition associated liver disease Diseases 0.000 claims 2
- 206010057969 Reflux gastritis Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000003613 bile acid Substances 0.000 claims 2
- 208000010643 digestive system disease Diseases 0.000 claims 2
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- JYTIXGYXBIBOMN-UHFFFAOYSA-N nidufexor Chemical compound Cn1nc(C(=O)N(Cc2ccccc2)Cc2ccc(cc2)C(O)=O)c2COc3ccc(Cl)cc3-c12 JYTIXGYXBIBOMN-UHFFFAOYSA-N 0.000 claims 2
- IMDAWGZBLRKXIE-UHFFFAOYSA-N 1-[[[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]methyl]cyclopropane-1-carboxylic acid Chemical compound ClC1=CC2=C(C=C1)OCC1=C2N(N=C1C(=O)N(CC1=C(C=CC=C1)F)CC(=O)NCC1(CC1)C(=O)O)C IMDAWGZBLRKXIE-UHFFFAOYSA-N 0.000 claims 1
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 claims 1
- OWQVCFQVVKBOOT-UHFFFAOYSA-N 3,5-difluoro-4-[2-[(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]ethoxy]benzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2c(F)cc(cc2F)C(O)=O)Cc2ccccc2F)c2COc3ccc(F)cc3-c12 OWQVCFQVVKBOOT-UHFFFAOYSA-N 0.000 claims 1
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 1
- PDRYWSXZQFRPQR-UHFFFAOYSA-N 3-[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]ethoxy]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2cc(ccc2F)C(O)=O)Cc2ccccc2F)c2COc3ccc(Cl)cc3-c12 PDRYWSXZQFRPQR-UHFFFAOYSA-N 0.000 claims 1
- DTQKJSVGRYVELH-UHFFFAOYSA-N 3-[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]ethylamino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCNc2cc(ccc2F)C(O)=O)Cc2ccccc2F)c2COc3ccc(Cl)cc3-c12 DTQKJSVGRYVELH-UHFFFAOYSA-N 0.000 claims 1
- LYVMCHZYDPLRTR-UHFFFAOYSA-N 3-[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]ethylamino]benzoic acid Chemical compound Cn1nc(C(=O)N(CCNc2cccc(c2)C(O)=O)Cc2ccccc2F)c2COc3ccc(Cl)cc3-c12 LYVMCHZYDPLRTR-UHFFFAOYSA-N 0.000 claims 1
- LRPVFIZBQAZGFZ-UHFFFAOYSA-N 3-[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-fluorophenyl)methyl]amino]ethylamino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCNc2cc(ccc2F)C(O)=O)Cc2cccc(F)c2)c2COc3ccc(Cl)cc3-c12 LRPVFIZBQAZGFZ-UHFFFAOYSA-N 0.000 claims 1
- HIYVXBLCLCKENU-UHFFFAOYSA-N 3-[2-[benzyl-(7,8-difluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]ethylamino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCNc2cc(ccc2F)C(O)=O)Cc2ccccc2)c2COc3cc(F)c(F)cc3-c12 HIYVXBLCLCKENU-UHFFFAOYSA-N 0.000 claims 1
- NYZPDZBXJAVCNO-UHFFFAOYSA-N 3-[2-[benzyl-(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]ethylamino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCNc2cc(ccc2F)C(O)=O)Cc2ccccc2)c2COc3ccc(Cl)cc3-c12 NYZPDZBXJAVCNO-UHFFFAOYSA-N 0.000 claims 1
- FFTIMDOOUCFJRA-UHFFFAOYSA-N 3-[2-[benzyl-(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]ethylamino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCNc2cc(ccc2F)C(O)=O)Cc2ccccc2)c2COc3ccc(F)cc3-c12 FFTIMDOOUCFJRA-UHFFFAOYSA-N 0.000 claims 1
- AXSQKBZSOIOPNL-UHFFFAOYSA-N 3-[[2-[(1,6-dimethyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]benzoic acid Chemical compound Cc1cccc2-c3c(COc12)c(nn3C)C(=O)N(CC(=O)Nc1cccc(c1)C(O)=O)Cc1ccccc1F AXSQKBZSOIOPNL-UHFFFAOYSA-N 0.000 claims 1
- DKTKXEQFYHWHHL-UHFFFAOYSA-N 3-[[2-[(1,8-dimethyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]benzoic acid Chemical compound Cc1ccc2OCc3c(nn(C)c3-c2c1)C(=O)N(CC(=O)Nc1cccc(c1)C(O)=O)Cc1ccccc1F DKTKXEQFYHWHHL-UHFFFAOYSA-N 0.000 claims 1
- XGTOEFRCFILKLS-UHFFFAOYSA-N 3-[[2-[(2-fluorophenyl)methyl-(1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]acetyl]amino]benzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cccc(c2)C(O)=O)Cc2ccccc2F)c2COc3ccccc3-c12 XGTOEFRCFILKLS-UHFFFAOYSA-N 0.000 claims 1
- BFOVMDBXSYRDBM-UHFFFAOYSA-N 3-[[2-[(6,8-difluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]benzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cccc(c2)C(O)=O)Cc2ccccc2F)c2COc3c(F)cc(F)cc3-c12 BFOVMDBXSYRDBM-UHFFFAOYSA-N 0.000 claims 1
- FCGNRHAXOCMKJS-UHFFFAOYSA-N 3-[[2-[(7,8-difluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2ccccc2F)c2COc3cc(F)c(F)cc3-c12 FCGNRHAXOCMKJS-UHFFFAOYSA-N 0.000 claims 1
- KNMNOGQXCIDEEU-UHFFFAOYSA-N 3-[[2-[(7,8-difluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-fluorophenyl)methyl]amino]acetyl]amino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2cccc(F)c2)c2COc3cc(F)c(F)cc3-c12 KNMNOGQXCIDEEU-UHFFFAOYSA-N 0.000 claims 1
- GGZMIQOZEZVMFU-UHFFFAOYSA-N 3-[[2-[(8-chloro-1-methyl-4,5-dihydrobenzo[g]indazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]benzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cccc(c2)C(O)=O)Cc2ccccc2F)c2CCc3ccc(Cl)cc3-c12 GGZMIQOZEZVMFU-UHFFFAOYSA-N 0.000 claims 1
- ZATHISJDRHJQBN-UHFFFAOYSA-N 3-[[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-(cyclopentylmethyl)amino]acetyl]amino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CC2CCCC2)CC(=O)Nc2cc(ccc2F)C(O)=O)c2COc3ccc(Cl)cc3-c12 ZATHISJDRHJQBN-UHFFFAOYSA-N 0.000 claims 1
- KULUFJJQJIWRFV-UHFFFAOYSA-N 3-[[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]-2,2-dimethylpropanoic acid Chemical compound ClC1=CC2=C(C=C1)OCC1=C2N(N=C1C(=O)N(CC1=C(C=CC=C1)F)CC(=O)NCC(C(=O)O)(C)C)C KULUFJJQJIWRFV-UHFFFAOYSA-N 0.000 claims 1
- DWQDJXCNBFBDPM-UHFFFAOYSA-N 3-[[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]-4-methylbenzoic acid Chemical compound Cc1ccc(cc1NC(=O)CN(Cc1ccccc1F)C(=O)c1nn(C)c-2c1COc1ccc(Cl)cc-21)C(O)=O DWQDJXCNBFBDPM-UHFFFAOYSA-N 0.000 claims 1
- KZZCHQQOPFXRBH-UHFFFAOYSA-N 3-[[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]-5-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(F)cc(c2)C(O)=O)Cc2ccccc2F)c2COc3ccc(Cl)cc3-c12 KZZCHQQOPFXRBH-UHFFFAOYSA-N 0.000 claims 1
- VGWTXFWZHWQQJH-UHFFFAOYSA-N 3-[[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-methylphenyl)methyl]amino]acetyl]amino]-4-fluorobenzoic acid Chemical compound Cc1cccc(CN(CC(=O)Nc2cc(ccc2F)C(O)=O)C(=O)c2nn(C)c-3c2COc2ccc(Cl)cc-32)c1 VGWTXFWZHWQQJH-UHFFFAOYSA-N 0.000 claims 1
- OHMJGQNDPYODGN-UHFFFAOYSA-N 3-[[2-[(8-chloro-6-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]benzoic acid Chemical compound ClC1=CC2=C(C(=C1)F)OCC1=C2N(N=C1C(=O)N(CC1=C(C=CC=C1)F)CC(=O)NC=1C=C(C(=O)O)C=CC1)C OHMJGQNDPYODGN-UHFFFAOYSA-N 0.000 claims 1
- HKEONNPTZPMISU-UHFFFAOYSA-N 3-[[2-[(9-chloro-1-methyl-4,5-dihydro-[1]benzoxepino[5,4-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]acetyl]amino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2ccccc2F)c2CCOc3ccc(Cl)cc3-c12 HKEONNPTZPMISU-UHFFFAOYSA-N 0.000 claims 1
- VZEJXIMAZDNTBT-UHFFFAOYSA-N 3-[[2-[benzyl-(1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]acetyl]amino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2ccccc2)c2COc3ccccc3-c12 VZEJXIMAZDNTBT-UHFFFAOYSA-N 0.000 claims 1
- VVZHZJSSBZCQJO-UHFFFAOYSA-N 3-[[2-[benzyl-(7,8-difluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]acetyl]amino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2ccccc2)c2COc3cc(F)c(F)cc3-c12 VVZHZJSSBZCQJO-UHFFFAOYSA-N 0.000 claims 1
- HMOKLCRRRAILAD-UHFFFAOYSA-N 3-[[2-[benzyl-(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]acetyl]amino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2ccccc2)c2COc3ccc(Cl)cc3-c12 HMOKLCRRRAILAD-UHFFFAOYSA-N 0.000 claims 1
- ZGIUMPYWCSNPSP-UHFFFAOYSA-N 3-[[2-[benzyl-(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]acetyl]amino]benzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cccc(c2)C(O)=O)Cc2ccccc2)c2COc3ccc(Cl)cc3-c12 ZGIUMPYWCSNPSP-UHFFFAOYSA-N 0.000 claims 1
- KVOGLRAFJSWVJO-UHFFFAOYSA-N 3-[[2-[benzyl-(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]acetyl]amino]-4-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2ccccc2)c2COc3ccc(F)cc3-c12 KVOGLRAFJSWVJO-UHFFFAOYSA-N 0.000 claims 1
- IJAKQJGOKGUNQY-UHFFFAOYSA-N 3-fluoro-4-[2-[(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]ethoxy]benzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2ccc(cc2F)C(O)=O)Cc2ccccc2F)c2COc3ccc(F)cc3-c12 IJAKQJGOKGUNQY-UHFFFAOYSA-N 0.000 claims 1
- WXMKEVSMUFZMKR-UHFFFAOYSA-N 4-[2-[(7,8-difluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]ethoxy]-3-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2ccc(cc2F)C(O)=O)Cc2ccccc2F)c2COc3cc(F)c(F)cc3-c12 WXMKEVSMUFZMKR-UHFFFAOYSA-N 0.000 claims 1
- PXZYNNRNWBUPNT-UHFFFAOYSA-N 4-[2-[(7,8-difluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-fluorophenyl)methyl]amino]ethoxy]-3-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2ccc(cc2F)C(O)=O)Cc2cccc(F)c2)c2COc3cc(F)c(F)cc3-c12 PXZYNNRNWBUPNT-UHFFFAOYSA-N 0.000 claims 1
- AZQSCICKUHOZOX-UHFFFAOYSA-N 4-[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-(cyclopentylmethyl)amino]ethoxy]-3,5-dimethylbenzoic acid Chemical compound Cc1cc(cc(C)c1OCCN(CC1CCCC1)C(=O)c1nn(C)c-2c1COc1ccc(Cl)cc-21)C(O)=O AZQSCICKUHOZOX-UHFFFAOYSA-N 0.000 claims 1
- XIDJZZCPABSJCW-UHFFFAOYSA-N 4-[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]ethoxy]-3,5-difluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2c(F)cc(cc2F)C(O)=O)Cc2ccccc2F)c2COc3ccc(Cl)cc3-c12 XIDJZZCPABSJCW-UHFFFAOYSA-N 0.000 claims 1
- BYGKMYHAYBMJMM-UHFFFAOYSA-N 4-[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]ethoxy]-3,5-dimethylbenzoic acid Chemical compound Cc1cc(cc(C)c1OCCN(Cc1ccccc1F)C(=O)c1nn(C)c-2c1COc1ccc(Cl)cc-21)C(O)=O BYGKMYHAYBMJMM-UHFFFAOYSA-N 0.000 claims 1
- YPNFQWNWBXQXPH-UHFFFAOYSA-N 4-[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]ethoxy]-3-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2ccc(cc2F)C(O)=O)Cc2ccccc2F)c2COc3ccc(Cl)cc3-c12 YPNFQWNWBXQXPH-UHFFFAOYSA-N 0.000 claims 1
- SMJHCJJTEVTFLW-UHFFFAOYSA-N 4-[2-[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-fluorophenyl)methyl]amino]ethoxy]-3-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2ccc(cc2F)C(O)=O)Cc2cccc(F)c2)c2COc3ccc(Cl)cc3-c12 SMJHCJJTEVTFLW-UHFFFAOYSA-N 0.000 claims 1
- ZVYKQLMAEOESRQ-UHFFFAOYSA-N 4-[2-[benzyl-(7,8-difluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]ethoxy]-3-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2ccc(cc2F)C(O)=O)Cc2ccccc2)c2COc3cc(F)c(F)cc3-c12 ZVYKQLMAEOESRQ-UHFFFAOYSA-N 0.000 claims 1
- OQNSPIUYFRIRCH-UHFFFAOYSA-N 4-[2-[benzyl-(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]ethoxy]-3,5-difluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2c(F)cc(cc2F)C(O)=O)Cc2ccccc2)c2COc3ccc(Cl)cc3-c12 OQNSPIUYFRIRCH-UHFFFAOYSA-N 0.000 claims 1
- ULAMPKYWOCISHL-UHFFFAOYSA-N 4-[2-[benzyl-(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]ethoxy]-3,5-difluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2c(F)cc(cc2F)C(O)=O)Cc2ccccc2)c2COc3ccc(F)cc3-c12 ULAMPKYWOCISHL-UHFFFAOYSA-N 0.000 claims 1
- RQLKTWUCUCJISI-UHFFFAOYSA-N 4-[2-[benzyl-(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]ethoxy]-3-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(CCOc2ccc(cc2F)C(O)=O)Cc2ccccc2)c2COc3ccc(F)cc3-c12 RQLKTWUCUCJISI-UHFFFAOYSA-N 0.000 claims 1
- LIBJDTRMQPEPNY-UHFFFAOYSA-N 4-[[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]methyl]-3-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(Cc2ccccc2F)Cc2ccc(cc2F)C(O)=O)c2COc3ccc(Cl)cc3-c12 LIBJDTRMQPEPNY-UHFFFAOYSA-N 0.000 claims 1
- IQIHHXCDAAIRAM-UHFFFAOYSA-N 4-[[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]methyl]benzoic acid Chemical compound Cn1nc(C(=O)N(Cc2ccc(cc2)C(O)=O)Cc2ccccc2F)c2COc3ccc(Cl)cc3-c12 IQIHHXCDAAIRAM-UHFFFAOYSA-N 0.000 claims 1
- UQQMPQAPKULNGX-UHFFFAOYSA-N 4-[[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3,5-difluorophenyl)methyl]amino]methyl]benzoic acid Chemical compound Cn1nc(C(=O)N(Cc2ccc(cc2)C(O)=O)Cc2cc(F)cc(F)c2)c2COc3ccc(Cl)cc3-c12 UQQMPQAPKULNGX-UHFFFAOYSA-N 0.000 claims 1
- KRWBWJRLLXSGJQ-UHFFFAOYSA-N 4-[[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-fluorophenyl)methyl]amino]methyl]-2-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(Cc2cccc(F)c2)Cc2ccc(C(O)=O)c(F)c2)c2COc3ccc(Cl)cc3-c12 KRWBWJRLLXSGJQ-UHFFFAOYSA-N 0.000 claims 1
- OISCITBTBYYNPZ-UHFFFAOYSA-N 4-[[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-methylphenyl)methyl]amino]methyl]-3-fluorobenzoic acid Chemical compound Cc1cccc(CN(Cc2ccc(cc2F)C(O)=O)C(=O)c2nn(C)c-3c2COc2ccc(Cl)cc-32)c1 OISCITBTBYYNPZ-UHFFFAOYSA-N 0.000 claims 1
- GJNULYRFVCWOQT-UHFFFAOYSA-N 4-[[benzyl-(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]methyl]-2-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(Cc2ccccc2)Cc2ccc(C(O)=O)c(F)c2)c2COc3ccc(Cl)cc3-c12 GJNULYRFVCWOQT-UHFFFAOYSA-N 0.000 claims 1
- HJBFMXAWFGCWBE-UHFFFAOYSA-N 4-[[benzyl-(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]methyl]-3-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(Cc2ccccc2)Cc2ccc(cc2F)C(O)=O)c2COc3ccc(Cl)cc3-c12 HJBFMXAWFGCWBE-UHFFFAOYSA-N 0.000 claims 1
- BMUMHLCCNNCEMA-UHFFFAOYSA-N 4-[[benzyl-(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]methyl]-3-fluorobenzoic acid Chemical compound Cn1nc(C(=O)N(Cc2ccccc2)Cc2ccc(cc2F)C(O)=O)c2COc3ccc(F)cc3-c12 BMUMHLCCNNCEMA-UHFFFAOYSA-N 0.000 claims 1
- YCUGJRWGKWZVKB-UHFFFAOYSA-N 4-fluoro-3-[2-[(2-fluorophenyl)methyl-(1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]ethylamino]benzoic acid Chemical compound FC1=C(C=C(C(=O)O)C=C1)NCCN(C(=O)C=1C2=C(N(N1)C)C=1C=CC=CC1OC2)CC2=C(C=CC=C2)F YCUGJRWGKWZVKB-UHFFFAOYSA-N 0.000 claims 1
- NOKLTKFAVVUZDY-UHFFFAOYSA-N 4-fluoro-3-[2-[(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]ethylamino]benzoic acid Chemical compound FC1=C(C=C(C(=O)O)C=C1)NCCN(C(=O)C=1C2=C(N(N1)C)C=1C=C(C=CC1OC2)F)CC2=C(C=CC=C2)F NOKLTKFAVVUZDY-UHFFFAOYSA-N 0.000 claims 1
- YMOMNUUERLHSSV-UHFFFAOYSA-N 4-fluoro-3-[2-[(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-fluorophenyl)methyl]amino]ethylamino]benzoic acid Chemical compound Cn1nc(C(=O)N(CCNc2cc(ccc2F)C(O)=O)Cc2cccc(F)c2)c2COc3ccc(F)cc3-c12 YMOMNUUERLHSSV-UHFFFAOYSA-N 0.000 claims 1
- MMZZOOQALWEITH-UHFFFAOYSA-N 4-fluoro-3-[2-[(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-methylphenyl)methyl]amino]ethylamino]benzoic acid Chemical compound FC1=C(C=C(C(=O)O)C=C1)NCCN(C(=O)C=1C2=C(N(N1)C)C=1C=C(C=CC1OC2)F)CC2=CC(=CC=C2)C MMZZOOQALWEITH-UHFFFAOYSA-N 0.000 claims 1
- NEXCYZNWKVTNOM-HNNXBMFYSA-N 4-fluoro-3-[[(2S)-2-[(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(2-fluorophenyl)methyl]amino]propanoyl]amino]benzoic acid Chemical compound FC1=C(C=C(C(=O)O)C=C1)NC([C@H](C)N(C(=O)C=1C2=C(N(N1)C)C=1C=C(C=CC1OC2)F)CC2=C(C=CC=C2)F)=O NEXCYZNWKVTNOM-HNNXBMFYSA-N 0.000 claims 1
- UWYOBIWUMJODEJ-UHFFFAOYSA-N 4-fluoro-3-[[2-[(1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-methylphenyl)methyl]amino]acetyl]amino]benzoic acid Chemical compound Cc1cccc(CN(CC(=O)Nc2cc(ccc2F)C(O)=O)C(=O)c2nn(C)c-3c2COc2ccccc-32)c1 UWYOBIWUMJODEJ-UHFFFAOYSA-N 0.000 claims 1
- PYNDYKVAQFINGU-UHFFFAOYSA-N 4-fluoro-3-[[2-[(2-fluorophenyl)methyl-(1-methyl-4,5-dihydropyrazolo[3,4-f]quinoline-3-carbonyl)amino]acetyl]amino]benzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2ccccc2F)c2CCc3ncccc3-c12 PYNDYKVAQFINGU-UHFFFAOYSA-N 0.000 claims 1
- KJMXTDPPYTXLEQ-UHFFFAOYSA-N 4-fluoro-3-[[2-[(2-fluorophenyl)methyl-(1-methyl-4,5-dihydropyrazolo[4,3-h]quinoline-3-carbonyl)amino]acetyl]amino]benzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2ccccc2F)c2CCc3cccnc3-c12 KJMXTDPPYTXLEQ-UHFFFAOYSA-N 0.000 claims 1
- OHKQMEARTYNBDN-UHFFFAOYSA-N 4-fluoro-3-[[2-[(3-fluorophenyl)methyl-(1,5,5-trimethyl-4H-benzo[g]indazole-3-carbonyl)amino]acetyl]amino]benzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2cccc(F)c2)c2CC(C)(C)c3ccccc3-c12 OHKQMEARTYNBDN-UHFFFAOYSA-N 0.000 claims 1
- UMNZXIQCUCGUCN-UHFFFAOYSA-N 4-fluoro-3-[[2-[(3-fluorophenyl)methyl-(1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]acetyl]amino]benzoic acid Chemical compound Cn1nc(C(=O)N(CC(=O)Nc2cc(ccc2F)C(O)=O)Cc2cccc(F)c2)c2COc3ccccc3-c12 UMNZXIQCUCGUCN-UHFFFAOYSA-N 0.000 claims 1
- BMSVWGYWVIMLBF-UHFFFAOYSA-N 4-fluoro-3-[[2-[(8-fluoro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-methylphenyl)methyl]amino]acetyl]amino]benzoic acid Chemical compound FC1=C(C=C(C(=O)O)C=C1)NC(CN(C(=O)C=1C2=C(N(N1)C)C=1C=C(C=CC1OC2)F)CC2=CC(=CC=C2)C)=O BMSVWGYWVIMLBF-UHFFFAOYSA-N 0.000 claims 1
- OIPRUMTZVHIJMF-UHFFFAOYSA-N 5-[[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-fluorophenyl)methyl]amino]methyl]-6-methylpyridine-2-carboxylic acid Chemical compound Cc1nc(ccc1CN(Cc1cccc(F)c1)C(=O)c1nn(C)c-2c1COc1ccc(Cl)cc-21)C(O)=O OIPRUMTZVHIJMF-UHFFFAOYSA-N 0.000 claims 1
- PMLAYJDPZOLTFC-UHFFFAOYSA-N 5-[[(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)-[(3-fluorophenyl)methyl]amino]methyl]pyridine-2-carboxylic acid Chemical compound Cn1nc(C(=O)N(Cc2ccc(nc2)C(O)=O)Cc2cccc(F)c2)c2COc3ccc(Cl)cc3-c12 PMLAYJDPZOLTFC-UHFFFAOYSA-N 0.000 claims 1
- 201000011374 Alagille syndrome Diseases 0.000 claims 1
- 208000022309 Alcoholic Liver disease Diseases 0.000 claims 1
- 125000006519 CCH3 Chemical group 0.000 claims 1
- RPWGKSUXPCHRRO-UHFFFAOYSA-N CN1N=C(C(N(CC(NC(C=C(C=C2)F)=C2C(O)=O)=O)CC2=CC(F)=CC=C2)=O)C2=C1C(C=C(C=C1)Cl)=C1OC2 Chemical compound CN1N=C(C(N(CC(NC(C=C(C=C2)F)=C2C(O)=O)=O)CC2=CC(F)=CC=C2)=O)C2=C1C(C=C(C=C1)Cl)=C1OC2 RPWGKSUXPCHRRO-UHFFFAOYSA-N 0.000 claims 1
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010024715 Liver transplant rejection Diseases 0.000 claims 1
- 208000033147 Parenteral nutrition-associated cholestasis Diseases 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- QNHCWLYFWBZVOM-UHFFFAOYSA-N benzoic acid;hydrate Chemical compound O.OC(=O)C1=CC=CC=C1 QNHCWLYFWBZVOM-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000007882 cirrhosis Effects 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940011871 estrogen Drugs 0.000 claims 1
- 239000000262 estrogen Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000035558 fertility Effects 0.000 claims 1
- 230000002440 hepatic effect Effects 0.000 claims 1
- 208000001024 intrahepatic cholestasis Diseases 0.000 claims 1
- 230000007872 intrahepatic cholestasis Effects 0.000 claims 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical class COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
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- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361900013P | 2013-11-05 | 2013-11-05 | |
| EP14803001.8A EP3065738B1 (en) | 2013-11-05 | 2014-11-04 | Compositions and methods for modulating farnesoid x receptors |
| PCT/US2014/063948 WO2015069666A1 (en) | 2013-11-05 | 2014-11-04 | Compositions and methods for modulating farnesoid x receptors |
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| Publication Number | Publication Date |
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| SI3065738T1 true SI3065738T1 (en) | 2018-06-29 |
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| SI201430692T SI3065738T1 (en) | 2013-11-05 | 2014-11-04 | Compounds and procedures for modulating the farnesoid X receptors |
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