JP2015503595A5 - - Google Patents
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- Publication number
- JP2015503595A5 JP2015503595A5 JP2014551505A JP2014551505A JP2015503595A5 JP 2015503595 A5 JP2015503595 A5 JP 2015503595A5 JP 2014551505 A JP2014551505 A JP 2014551505A JP 2014551505 A JP2014551505 A JP 2014551505A JP 2015503595 A5 JP2015503595 A5 JP 2015503595A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- heterocyclyl
- compound
- heteroaryl
- cycloalkyl
- 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 47
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 31
- 125000001072 heteroaryl group Chemical group 0.000 claims 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims 28
- 150000003839 salts Chemical class 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 25
- 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 claims 17
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 102100026148 Free fatty acid receptor 1 Human genes 0.000 claims 4
- 101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- DGENZVKCTGIDRZ-UHFFFAOYSA-N 3-[4-[(3-phenoxyphenyl)methylamino]phenyl]propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1NCC1=CC=CC(OC=2C=CC=CC=2)=C1 DGENZVKCTGIDRZ-UHFFFAOYSA-N 0.000 claims 2
- 229940125827 GPR40 agonist Drugs 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 239000000243 solution Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- -1 phenyl compound Chemical class 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 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 8
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 238000010828 elution Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- YFPCLQKFNXUAAK-UHFFFAOYSA-N cyclopentyl acetate Chemical compound CC(=O)OC1CCCC1 YFPCLQKFNXUAAK-UHFFFAOYSA-N 0.000 description 3
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HWUBARZKSVOKKK-AREMUKBSSA-N 2-[(3s)-6-[[3-[2,6-dimethyl-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxyphenyl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=C4OC[C@@H](CC(O)=O)C4=CC=3)C=CC=2)C(C)=CC=1OC1CCN(C(=O)OC(C)(C)C)CC1 HWUBARZKSVOKKK-AREMUKBSSA-N 0.000 description 2
- GNSJAOXMTQXKPL-NFBKMPQASA-N 2-[(3s)-6-[[5-[2,6-dimethyl-4-[(3r)-oxolan-3-yl]oxyphenyl]-2-hydroxyphenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=C4OC[C@@H](CC(O)=O)C4=CC=3)C(O)=CC=2)C(C)=CC=1O[C@@H]1CCOC1 GNSJAOXMTQXKPL-NFBKMPQASA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 210000003097 mucus Anatomy 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- GJEZBVHHZQAEDB-SYDPRGILSA-N (1s,5r)-6-oxabicyclo[3.1.0]hexane Chemical compound C1CC[C@H]2O[C@H]21 GJEZBVHHZQAEDB-SYDPRGILSA-N 0.000 description 1
- BBTGETRKFPWMMZ-HSZRJFAPSA-N 2-[(3s)-6-[[3-[2,6-dimethyl-4-(1-propanoylazetidin-3-yl)oxyphenyl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C1N(C(=O)CC)CC1OC1=CC(C)=C(C=2C=C(COC=3C=C4OC[C@@H](CC(O)=O)C4=CC=3)C=CC=2)C(C)=C1 BBTGETRKFPWMMZ-HSZRJFAPSA-N 0.000 description 1
- GIZVCPXCAQOBAY-ILBGXUMGSA-N 2-[(3s)-6-[[3-[2,6-dimethyl-4-[(3r)-1-methylsulfonylpyrrolidin-3-yl]oxyphenyl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=C4OC[C@@H](CC(O)=O)C4=CC=3)C=CC=2)C(C)=CC=1O[C@@H]1CCN(S(C)(=O)=O)C1 GIZVCPXCAQOBAY-ILBGXUMGSA-N 0.000 description 1
- NRMCDKBVCXQLCB-VPUSJEBWSA-N 2-[(3s)-6-[[3-[2,6-dimethyl-4-[(3s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-3-yl]oxyphenyl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=C4OC[C@@H](CC(O)=O)C4=CC=3)C=CC=2)C(C)=CC=1O[C@H]1CCN(C(=O)OC(C)(C)C)C1 NRMCDKBVCXQLCB-VPUSJEBWSA-N 0.000 description 1
- IRVNXZAQDKLDOT-POURPWNDSA-N 2-[(3s)-6-[[5-[2,6-dimethyl-4-[(3r)-oxolan-3-yl]oxyphenyl]-2-phenylmethoxyphenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=C4OC[C@@H](CC(O)=O)C4=CC=3)C(OCC=3C=CC=CC=3)=CC=2)C(C)=CC=1O[C@@H]1CCOC1 IRVNXZAQDKLDOT-POURPWNDSA-N 0.000 description 1
- OBEDIUDGEVLUGG-UHFFFAOYSA-N 2-[6-[[3-(2,6-dimethyl-4-piperidin-4-yloxyphenyl)phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=C4OCC(CC(O)=O)C4=CC=3)C=CC=2)C(C)=CC=1OC1CCNCC1 OBEDIUDGEVLUGG-UHFFFAOYSA-N 0.000 description 1
- RGTRSFUXNGBZKU-UHFFFAOYSA-N 3-(4-hydroxy-2,6-dimethylphenyl)benzaldehyde Chemical compound CC1=CC(O)=CC(C)=C1C1=CC=CC(C=O)=C1 RGTRSFUXNGBZKU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- NPMLAFCTRRQRJD-UHFFFAOYSA-N OC1CCNCC1.OC1CCN(CC1)C(=O)OC(C)(C)C Chemical compound OC1CCNCC1.OC1CCN(CC1)C(=O)OC(C)(C)C NPMLAFCTRRQRJD-UHFFFAOYSA-N 0.000 description 1
- WYYUCIHSRDQKES-QVAQPMOVSA-N O[C@@H]1CN(CC1)C(=O)OC(C)(C)C.Cl.O[C@@H]1CNCC1 Chemical compound O[C@@H]1CN(CC1)C(=O)OC(C)(C)C.Cl.O[C@@H]1CNCC1 WYYUCIHSRDQKES-QVAQPMOVSA-N 0.000 description 1
- GSGYFWDQUOYKSX-FGVGDJRVSA-N O[C@H]1CNCC1.C(=O)(OC(C)(C)C)N1C[C@@H](CC1)O Chemical compound O[C@H]1CNCC1.C(=O)(OC(C)(C)C)N1C[C@@H](CC1)O GSGYFWDQUOYKSX-FGVGDJRVSA-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
- KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- HBEDSQVIWPRPAY-UHFFFAOYSA-N dihydro-benzofuran Natural products C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 1
- 150000002440 hydroxy compounds Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- MIFNUMWQYKGPGC-XMMPIXPASA-N methyl 2-[(3s)-6-[[3-(2,6-dimethyl-4-piperidin-4-yloxyphenyl)phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H](C1=CC=2)CC(=O)OC)OC1=CC=2OCC(C=1)=CC=CC=1C(C(=C1)C)=C(C)C=C1OC1CCNCC1 MIFNUMWQYKGPGC-XMMPIXPASA-N 0.000 description 1
- VMSCNYLKNKMHAP-HXUWFJFHSA-N methyl 2-[(3s)-6-[[3-(4-hydroxy-2,6-dimethylphenyl)phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H](C1=CC=2)CC(=O)OC)OC1=CC=2OCC(C=1)=CC=CC=1C1=C(C)C=C(O)C=C1C VMSCNYLKNKMHAP-HXUWFJFHSA-N 0.000 description 1
- RHMDISFJOKCCAQ-SSDOTTSWSA-N methyl 2-[(3s)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 RHMDISFJOKCCAQ-SSDOTTSWSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- PKXZJJICMGZSAS-RUZDIDTESA-N tert-butyl 3-[4-[3-[[(3s)-3-(2-methoxy-2-oxoethyl)-2,3-dihydro-1-benzofuran-6-yl]oxymethyl]phenyl]-3,5-dimethylphenoxy]azetidine-1-carboxylate Chemical compound C([C@H](C1=CC=2)CC(=O)OC)OC1=CC=2OCC(C=1)=CC=CC=1C(C(=C1)C)=C(C)C=C1OC1CN(C(=O)OC(C)(C)C)C1 PKXZJJICMGZSAS-RUZDIDTESA-N 0.000 description 1
- OFFXGAMUFNSMCO-HHHXNRCGSA-N tert-butyl 4-[4-[3-[[(3s)-3-(2-methoxy-2-oxoethyl)-2,3-dihydro-1-benzofuran-6-yl]oxymethyl]phenyl]-3,5-dimethylphenoxy]piperidine-1-carboxylate Chemical compound C([C@H](C1=CC=2)CC(=O)OC)OC1=CC=2OCC(C=1)=CC=CC=1C(C(=C1)C)=C(C)C=C1OC1CCN(C(=O)OC(C)(C)C)CC1 OFFXGAMUFNSMCO-HHHXNRCGSA-N 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210008286.9 | 2012-01-12 | ||
| CN201210008286 | 2012-01-12 | ||
| PCT/CN2012/087606 WO2013104257A1 (zh) | 2012-01-12 | 2012-12-27 | 多环类衍生物、其制备方法及其在医药上的应用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015503595A JP2015503595A (ja) | 2015-02-02 |
| JP2015503595A5 true JP2015503595A5 (enExample) | 2016-01-28 |
| JP6122871B2 JP6122871B2 (ja) | 2017-04-26 |
Family
ID=48781054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014551505A Active JP6122871B2 (ja) | 2012-01-12 | 2012-12-27 | 多環式化合物誘導体、それらの製造方法および医薬用途 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9139548B2 (enExample) |
| EP (1) | EP2803664B1 (enExample) |
| JP (1) | JP6122871B2 (enExample) |
| KR (1) | KR102036547B1 (enExample) |
| CN (1) | CN103429581B (enExample) |
| AU (1) | AU2012365706B2 (enExample) |
| BR (1) | BR112014016648B1 (enExample) |
| CA (1) | CA2860353A1 (enExample) |
| MX (1) | MX357780B (enExample) |
| RU (1) | RU2621039C1 (enExample) |
| TW (1) | TWI588136B (enExample) |
| UA (1) | UA115975C2 (enExample) |
| WO (1) | WO2013104257A1 (enExample) |
| ZA (1) | ZA201404625B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592211B (zh) * | 2013-10-31 | 2018-10-16 | 广东东阳光药业有限公司 | 联苯类化合物及其用途 |
| CN104650055A (zh) * | 2013-11-22 | 2015-05-27 | 山东轩竹医药科技有限公司 | 芳香多环羧酸衍生物 |
| CN104788412B (zh) * | 2014-01-22 | 2017-02-15 | 山东轩竹医药科技有限公司 | 芳香多环羧酸衍生物 |
| US10968193B2 (en) | 2014-08-08 | 2021-04-06 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| US10100042B2 (en) | 2014-08-08 | 2018-10-16 | Merck Sharp & Dohme Corp. | [5,6]—fused bicyclic antidiabetic compounds |
| EP3177282B1 (en) | 2014-08-08 | 2021-10-06 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| WO2016019587A1 (en) | 2014-08-08 | 2016-02-11 | Merck Sharp & Dohme Corp. | [7, 6]-fused bicyclic antidiabetic compounds |
| PL3206756T3 (pl) | 2014-10-14 | 2019-06-28 | Basf Se | Zastosowanie heksadeka-8,15-dienalu jako aromatycznej substancji chemicznej |
| CN106478616B (zh) * | 2015-08-27 | 2020-05-12 | 江苏恒瑞医药股份有限公司 | 一种gpr40激动剂的结晶形式及其制备方法 |
| CN108236611A (zh) * | 2016-12-27 | 2018-07-03 | 江苏恒瑞医药股份有限公司 | 两种化合物联合在制备治疗糖尿病药物中的用途 |
| CN108236609B (zh) * | 2016-12-27 | 2022-10-21 | 江苏恒瑞医药股份有限公司 | 一种gpr40激动剂药物组合物及其制备方法 |
| WO2019160882A1 (en) | 2018-02-13 | 2019-08-22 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| WO2019204609A1 (en) | 2018-04-19 | 2019-10-24 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| BR112020026746A2 (pt) | 2018-07-13 | 2021-03-30 | Gilead Sciences, Inc. | Composto, composição farmacêutica, métodos para inibir pd-1, pd-l1 e/ou a interação de pd-1/pd-l1 e para tratar câncer, e, kit para tratar ou prevenir câncer ou uma doença ou condição. |
| CN112955435B (zh) | 2018-10-24 | 2024-09-06 | 吉利德科学公司 | Pd-1/pd-l1抑制剂 |
| JP2022552655A (ja) | 2019-10-07 | 2022-12-19 | キャリーオペ，インク． | Ｇｐｒ１１９アゴニスト |
| PH12022552277A1 (en) | 2020-02-28 | 2024-03-04 | Kallyope Inc | Gpr40 agonists |
| JP2023526625A (ja) | 2020-05-19 | 2023-06-22 | キャリーオペ，インク． | Ａｍｐｋアクチベーター |
| CN116390925A (zh) | 2020-06-26 | 2023-07-04 | 卡尔优普公司 | Ampk活化剂 |
| CN114163426B (zh) * | 2020-09-10 | 2024-03-19 | 上海爱博医药科技有限公司 | 苯并含氧杂环类化合物及其医药应用 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0772610B9 (de) * | 1994-07-22 | 2001-07-25 | Byk Gulden Lomberg Chemische Fabrik GmbH | Dihydrobenzofurane |
| EP1630152A4 (en) * | 2003-05-30 | 2009-09-23 | Takeda Pharmaceutical | CONDENSED CYCLIC COMPOUND |
| US20060257987A1 (en) | 2003-08-20 | 2006-11-16 | Gonzalez Valcarcel Isabel Cris | Ppar modulators |
| WO2005051890A1 (en) | 2003-11-19 | 2005-06-09 | Smithkline Beecham Corporation | Aminophenylcyclopropyl carboxylic acids and derivatives as agonists to gpr40 |
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| AU2004309271A1 (en) * | 2003-12-25 | 2005-07-14 | Takeda Pharmaceutical Company Limited | 3-(4-benzyloxyphenyl)propanoic acid derivatives |
| EP1726580A4 (en) * | 2004-03-15 | 2008-02-13 | Takeda Pharmaceutical | AMINOPHNYLPROPANO ACID DERIVATIVE |
| EP1749000A4 (en) * | 2004-05-25 | 2009-12-30 | Metabolex Inc | BICYCLIC SUBSTITUTED TRIAZOLE AS PPAR MODULATORS AND METHOD FOR THE PRODUCTION THEREOF |
| CA2646430A1 (en) * | 2006-03-14 | 2007-09-20 | Amgen Inc. | Bicyclic carboxylic acid derivatives useful for treating metabolic disorders |
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| BRPI1013937A2 (pt) * | 2009-04-22 | 2016-08-09 | Astellas Pharma Inc | compostos de ácido carboxílico |
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-
2012
- 2012-12-27 UA UAA201408867A patent/UA115975C2/uk unknown
- 2012-12-27 KR KR1020147022007A patent/KR102036547B1/ko not_active Expired - Fee Related
- 2012-12-27 US US14/371,123 patent/US9139548B2/en not_active Expired - Fee Related
- 2012-12-27 BR BR112014016648-0A patent/BR112014016648B1/pt not_active IP Right Cessation
- 2012-12-27 WO PCT/CN2012/087606 patent/WO2013104257A1/zh not_active Ceased
- 2012-12-27 CN CN201280011690.XA patent/CN103429581B/zh active Active
- 2012-12-27 MX MX2014008125A patent/MX357780B/es active IP Right Grant
- 2012-12-27 AU AU2012365706A patent/AU2012365706B2/en not_active Ceased
- 2012-12-27 EP EP12865081.9A patent/EP2803664B1/en not_active Not-in-force
- 2012-12-27 JP JP2014551505A patent/JP6122871B2/ja active Active
- 2012-12-27 CA CA2860353A patent/CA2860353A1/en not_active Abandoned
- 2012-12-27 RU RU2014132158A patent/RU2621039C1/ru not_active IP Right Cessation
-
2013
- 2013-01-09 TW TW102100678A patent/TWI588136B/zh not_active IP Right Cessation
-
2014
- 2014-06-24 ZA ZA2014/04625A patent/ZA201404625B/en unknown
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