JP2018519252A5 - - Google Patents
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- JP2018519252A5 JP2018519252A5 JP2017556538A JP2017556538A JP2018519252A5 JP 2018519252 A5 JP2018519252 A5 JP 2018519252A5 JP 2017556538 A JP2017556538 A JP 2017556538A JP 2017556538 A JP2017556538 A JP 2017556538A JP 2018519252 A5 JP2018519252 A5 JP 2018519252A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- chromeno
- pyrazol
- acetamide
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 51
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- -1 tetrapyranyl Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 102100038495 Bile acid receptor Human genes 0.000 claims description 16
- 101000603876 Homo sapiens Bile acid receptor Proteins 0.000 claims description 16
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 230000001404 mediated effect Effects 0.000 claims description 14
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 206010008635 Cholestasis Diseases 0.000 claims description 8
- 230000007870 cholestasis Effects 0.000 claims description 8
- 231100000359 cholestasis Toxicity 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 208000019423 liver disease Diseases 0.000 claims description 8
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 210000004185 liver Anatomy 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 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 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 4
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 4
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
- 206010012735 Diarrhoea Diseases 0.000 claims description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 4
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 4
- 239000003613 bile acid Substances 0.000 claims description 4
- SYGSTRANUHFLOT-UHFFFAOYSA-N chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC=C2C3=NN=C(C(=O)N)C3=COC2=C1 SYGSTRANUHFLOT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 208000010643 digestive system disease Diseases 0.000 claims description 4
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 235000016236 parenteral nutrition Nutrition 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 238000002054 transplantation Methods 0.000 claims description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
- OHLADRJEBUQJMW-UHFFFAOYSA-N 8-chloro-N-[(2-fluorophenyl)methyl]-1-methyl-N-[2-(propan-2-ylcarbamoylamino)ethyl]-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound ClC1=CC2=C(C=C1)OCC1=C2N(N=C1C(=O)N(CCNC(NC(C)C)=O)CC1=C(C=CC=C1)F)C OHLADRJEBUQJMW-UHFFFAOYSA-N 0.000 claims description 2
- BZJJXKGWZPZYQE-UHFFFAOYSA-N 8-chloro-N-[(2-fluorophenyl)methyl]-1-methyl-N-[2-(propan-2-ylsulfonylamino)ethyl]-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound ClC1=CC2=C(C=C1)OCC1=C2N(N=C1C(=O)N(CCNS(=O)(=O)C(C)C)CC1=C(C=CC=C1)F)C BZJJXKGWZPZYQE-UHFFFAOYSA-N 0.000 claims description 2
- OGHLXWSUHYMUKS-UHFFFAOYSA-N 8-chloro-N-[(3-fluorophenyl)methyl]-1-methyl-N-[2-(1,3-thiazol-2-ylamino)ethyl]-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound ClC1=CC2=C(C=C1)OCC1=C2N(N=C1C(=O)N(CCNC=1SC=CN=1)CC1=CC(=CC=C1)F)C OGHLXWSUHYMUKS-UHFFFAOYSA-N 0.000 claims description 2
- IAEQIQBKMOAWGP-UHFFFAOYSA-N 8-chloro-N-[2-(cyclopropylmethylcarbamoylamino)ethyl]-N-[(2-fluorophenyl)methyl]-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound ClC1=CC2=C(C=C1)OCC1=C2N(N=C1C(=O)N(CC1=C(C=CC=C1)F)CCNC(NCC1CC1)=O)C IAEQIQBKMOAWGP-UHFFFAOYSA-N 0.000 claims description 2
- 208000022309 Alcoholic Liver disease Diseases 0.000 claims description 2
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- JGSWAGMWZXMFQW-UHFFFAOYSA-N N-(2-acetamidoethyl)-N-benzyl-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=CC=CC=1OC2)CCNC(C)=O JGSWAGMWZXMFQW-UHFFFAOYSA-N 0.000 claims description 2
- MACNYKLUIOMLPQ-UHFFFAOYSA-N N-(2-acetamidoethyl)-N-benzyl-8-bromo-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)Br)CCNC(C)=O MACNYKLUIOMLPQ-UHFFFAOYSA-N 0.000 claims description 2
- QYPXPQNPAVMDSX-UHFFFAOYSA-N N-(2-acetamidoethyl)-N-benzyl-8-butan-2-yl-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)C(C)CC)CCNC(C)=O QYPXPQNPAVMDSX-UHFFFAOYSA-N 0.000 claims description 2
- CBMHPXMRCSOEGI-UHFFFAOYSA-N N-(2-acetamidoethyl)-N-benzyl-8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)Cl)CCNC(C)=O CBMHPXMRCSOEGI-UHFFFAOYSA-N 0.000 claims description 2
- KLTWDTANPBFDIR-UHFFFAOYSA-N N-(2-acetamidoethyl)-N-benzyl-8-cyclopropyl-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)C1CC1)CCNC(C)=O KLTWDTANPBFDIR-UHFFFAOYSA-N 0.000 claims description 2
- ROHLVDVTZUAMTQ-UHFFFAOYSA-N N-(2-acetamidoethyl)-N-benzyl-8-ethenyl-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)C=C)CCNC(C)=O ROHLVDVTZUAMTQ-UHFFFAOYSA-N 0.000 claims description 2
- CDHOHVGLWSAVQU-UHFFFAOYSA-N N-(2-acetamidoethyl)-N-benzyl-8-iodo-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)I)CCNC(C)=O CDHOHVGLWSAVQU-UHFFFAOYSA-N 0.000 claims description 2
- RFSOIZWEFLJNBM-UHFFFAOYSA-N N-[(4-aminophenyl)methyl]-N-benzyl-8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound NC1=CC=C(C=C1)CN(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)Cl)CC1=CC=CC=C1 RFSOIZWEFLJNBM-UHFFFAOYSA-N 0.000 claims description 2
- DGRCTKXRBNKOSI-UHFFFAOYSA-N N-[2-(4-carbamoyl-2-fluorophenoxy)ethyl]-8-chloro-N-[(2-fluorophenyl)methyl]-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(N)(=O)C1=CC(=C(OCCN(C(=O)C=2C3=C(N(N=2)C)C=2C=C(C=CC=2OC3)Cl)CC2=C(C=CC=C2)F)C=C1)F DGRCTKXRBNKOSI-UHFFFAOYSA-N 0.000 claims description 2
- ALLYMLNBCFGBDF-UHFFFAOYSA-N N-benzyl-8-bromo-1-methyl-N-[2-(2-methylpropanoylamino)ethyl]-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)Br)CCNC(C(C)C)=O ALLYMLNBCFGBDF-UHFFFAOYSA-N 0.000 claims description 2
- KALKGDNPOCPEPI-UHFFFAOYSA-N N-benzyl-8-bromo-1-methyl-N-[2-(propan-2-ylsulfonylamino)ethyl]-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)Br)CCNS(=O)(=O)C(C)C KALKGDNPOCPEPI-UHFFFAOYSA-N 0.000 claims description 2
- OTBKYMXVSVHGNW-UHFFFAOYSA-N N-benzyl-8-chloro-1-methyl-N-[(4-methylsulfonylphenyl)methyl]-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)Cl)CC1=CC=C(C=C1)S(=O)(=O)C OTBKYMXVSVHGNW-UHFFFAOYSA-N 0.000 claims description 2
- XFVSJYUXQSJETC-UHFFFAOYSA-N N-benzyl-8-chloro-1-methyl-N-[2-(2-methylpropanoylamino)ethyl]-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)Cl)CCNC(C(C)C)=O XFVSJYUXQSJETC-UHFFFAOYSA-N 0.000 claims description 2
- HBZUVACJLAETFL-UHFFFAOYSA-N N-benzyl-8-chloro-1-methyl-N-[[4-(methylsulfamoyl)phenyl]methyl]-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)Cl)CC1=CC=C(C=C1)S(NC)(=O)=O HBZUVACJLAETFL-UHFFFAOYSA-N 0.000 claims description 2
- CWCIRYMDLDCTEP-UHFFFAOYSA-N N-benzyl-8-chloro-N-[(3-fluorophenyl)methyl]-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C2=C(N(N=1)C)C=1C=C(C=CC=1OC2)Cl)CC1=CC(=CC=C1)F CWCIRYMDLDCTEP-UHFFFAOYSA-N 0.000 claims description 2
- NAHCXGDLFTYZHZ-UHFFFAOYSA-N N-benzyl-N-[(4-carbamoylphenyl)methyl]-8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound Cn1nc(C(=O)N(Cc2ccccc2)Cc2ccc(cc2)C(N)=O)c2COc3ccc(Cl)cc3-c12 NAHCXGDLFTYZHZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010057969 Reflux gastritis Diseases 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000001587 cholestatic effect Effects 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229940011871 estrogen Drugs 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
- 208000024908 graft versus host disease Diseases 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 208000001024 intrahepatic cholestasis Diseases 0.000 claims description 2
- 230000007872 intrahepatic cholestasis Effects 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 230000035935 pregnancy Effects 0.000 claims description 2
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims description 2
- 230000000750 progressive effect Effects 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 208000010157 sclerosing cholangitis Diseases 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- BGUQVOOXVXLYEI-UHFFFAOYSA-N N-[2-(4-carbamoyl-2-fluorophenoxy)ethyl]-8-fluoro-N-[(2-fluorophenyl)methyl]-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C(N)(=O)C1=CC(=C(OCCN(C(=O)C=2C3=C(N(N=2)C)C=2C=C(C=CC=2OC3)F)CC2=C(C=CC=C2)F)C=C1)F BGUQVOOXVXLYEI-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562154862P | 2015-04-30 | 2015-04-30 | |
| US62/154,862 | 2015-04-30 | ||
| PCT/IB2016/052424 WO2016174616A1 (en) | 2015-04-30 | 2016-04-29 | Fused tricyclic pyrazole derivatives useful for modulating farnesoid x receptors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018519252A JP2018519252A (ja) | 2018-07-19 |
| JP2018519252A5 true JP2018519252A5 (https=) | 2019-05-09 |
| JP6691552B2 JP6691552B2 (ja) | 2020-04-28 |
Family
ID=55910302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017556538A Expired - Fee Related JP6691552B2 (ja) | 2015-04-30 | 2016-04-29 | ファルネソイドｘ受容体をモジュレートするのに有用である縮合三環式ピラゾール誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10351576B2 (https=) |
| EP (1) | EP3288948B1 (https=) |
| JP (1) | JP6691552B2 (https=) |
| CN (1) | CN107531721B (https=) |
| ES (1) | ES2770128T3 (https=) |
| WO (1) | WO2016174616A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102350357B1 (ko) | 2013-11-05 | 2022-01-14 | 노파르티스 아게 | 파르네소이드 x 수용체의 조정을 위한 조성물 및 방법 |
| TW201808283A (zh) * | 2016-08-05 | 2018-03-16 | 廣東東陽光藥業有限公司 | 含氮三環化合物及其在藥物中的應用 |
| CN116056719A (zh) * | 2020-06-30 | 2023-05-02 | 索伦·欧克维克 | 包含鸟苷酸环化酶c(gucy2c)激动剂和短链脂肪酸或其前药的组合的药物组合物 |
| CN120682241A (zh) * | 2024-03-22 | 2025-09-23 | 复旦大学附属中山医院 | 三环骨架化合物及其在制备抗肿瘤药物中的应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT72878B (en) | 1980-04-24 | 1983-03-29 | Merck & Co Inc | Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents |
| EP0463090A1 (en) * | 1989-03-09 | 1992-01-02 | E.I. Du Pont De Nemours And Company | Arthropodicidal tetrahydrobenzopyranopyrazoles |
| JP3006925B2 (ja) * | 1990-09-14 | 2000-02-07 | 協和醗酵工業株式会社 | ピラゾロキノリン誘導体 |
| JP2007524596A (ja) | 2003-02-28 | 2007-08-30 | トランスフォーム・ファーマシューティカルズ・インコーポレイテッド | 共結晶医薬組成物 |
| US20040259887A1 (en) * | 2003-06-18 | 2004-12-23 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| EP2343302A1 (en) * | 2004-07-12 | 2011-07-13 | Cadila Healthcare Limited | Tricyclic pyrazole derivatives as cannabinoid receptor modulators |
| IN2014DN02217A (https=) * | 2005-04-12 | 2015-07-10 | Vicore Pharma Ab | |
| BRPI0712262A2 (pt) * | 2006-05-24 | 2012-07-10 | Lilly Co Eli | agonistas de fxr |
| JP2012506848A (ja) * | 2008-10-27 | 2012-03-22 | グラクソ グループ リミテッド | グルタミン酸受容体モジュレーターとしての三環式化合物 |
| IT1394400B1 (it) * | 2009-02-25 | 2012-06-15 | Neuroscienze Pharmaness S C Ar L | Composizioni farmaceutiche |
| IT1395724B1 (it) * | 2009-02-25 | 2012-10-19 | Neuroscienze Pharmaness S C A R L | Composti farmaceutici |
| IT1393930B1 (it) * | 2009-02-25 | 2012-05-17 | Neuroscienze Pharmaness S C A R L | Composti farmaceutici |
| US8071589B2 (en) * | 2009-07-31 | 2011-12-06 | N. V. Organon | Dihydrobenzoindazoles |
| MY160064A (en) * | 2009-09-28 | 2017-02-15 | Hoffmann La Roche | Benzoxazepin pi3k inhibitor compounds and methods of use |
| KR102318498B1 (ko) * | 2013-06-24 | 2021-10-27 | 메르크 파텐트 게엠베하 | Fshr의 조절인자로서의 피라졸 화합물 및 이의 용도 |
| KR102350357B1 (ko) * | 2013-11-05 | 2022-01-14 | 노파르티스 아게 | 파르네소이드 x 수용체의 조정을 위한 조성물 및 방법 |
-
2016
- 2016-04-29 CN CN201680023961.1A patent/CN107531721B/zh not_active Expired - Fee Related
- 2016-04-29 US US15/569,498 patent/US10351576B2/en active Active
- 2016-04-29 WO PCT/IB2016/052424 patent/WO2016174616A1/en not_active Ceased
- 2016-04-29 EP EP16720183.9A patent/EP3288948B1/en active Active
- 2016-04-29 ES ES16720183T patent/ES2770128T3/es active Active
- 2016-04-29 JP JP2017556538A patent/JP6691552B2/ja not_active Expired - Fee Related
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