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 |
|---|---|---|---|---|
| BR112016009630B1 (pt) | 2013-11-05 | 2021-02-09 | Novartis Ag | receptores de farnesoide x, seus usos, combinação e composição farmacêutica |
| 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 |
| JP7599014B2 (ja) * | 2020-06-30 | 2024-12-12 | オクヴィルク，ゼレン | グアニル酸シクラーゼｃ（ｇｕｃｙ２ｃ）アゴニストおよび短鎖脂肪酸またはそのプロドラッグの組み合わせを含む医薬組成物 |
| 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 |
| EP0386892A3 (en) * | 1989-03-09 | 1990-11-28 | 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 |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| US20040259887A1 (en) * | 2003-06-18 | 2004-12-23 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| JP2008505965A (ja) * | 2004-07-12 | 2008-02-28 | カディラ ヘルスケア リミティド | カンナビノイド受容体修飾因子としての三環式ピラゾール誘導体 |
| ES2582945T3 (es) * | 2005-04-12 | 2016-09-16 | Vicore Pharma Ab | Nuevos agonistas bicíclicos de angiotensina II |
| CN101448791B (zh) * | 2006-05-24 | 2011-11-16 | 伊莱利利公司 | Fxr激动剂 |
| EP2346832A1 (en) * | 2008-10-27 | 2011-07-27 | Glaxo Group Limited | Tricyclic compounds as glutamate receptor modulators |
| IT1395724B1 (it) * | 2009-02-25 | 2012-10-19 | Neuroscienze Pharmaness S C A R L | Composti farmaceutici |
| IT1394400B1 (it) * | 2009-02-25 | 2012-06-15 | Neuroscienze Pharmaness S C Ar L | Composizioni farmaceutiche |
| 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 |
| ES2570569T3 (es) * | 2009-09-28 | 2016-05-19 | Hoffmann La Roche | Compuestos de benzoxazepina como inhibidores de la PI3K y métodos de uso |
| WO2014209980A1 (en) * | 2013-06-24 | 2014-12-31 | Merck Patent Gmbh | Pyrazole compounds as modulators of fshr and uses thereof |
| BR112016009630B1 (pt) * | 2013-11-05 | 2021-02-09 | Novartis Ag | receptores de farnesoide x, seus usos, combinação e composição farmacêutica |
-
2016
- 2016-04-29 CN CN201680023961.1A patent/CN107531721B/zh not_active Expired - Fee Related
- 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
- 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
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