ES2546154T3 - Ácidos indaniloxidihidrobenzofuranilacéticos, útiles para el tratamiento del síndrome metabólico - Google Patents
Ácidos indaniloxidihidrobenzofuranilacéticos, útiles para el tratamiento del síndrome metabólico Download PDFInfo
- Publication number
- ES2546154T3 ES2546154T3 ES11788845.3T ES11788845T ES2546154T3 ES 2546154 T3 ES2546154 T3 ES 2546154T3 ES 11788845 T ES11788845 T ES 11788845T ES 2546154 T3 ES2546154 T3 ES 2546154T3
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- Prior art keywords
- alkyl
- groups
- indan
- group
- cycloalkyl
- Prior art date
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- 239000002253 acid Substances 0.000 title description 20
- 150000007513 acids Chemical class 0.000 title description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 title 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 110
- -1 cyano, nitro, amino Chemical group 0.000 abstract description 95
- 125000000217 alkyl group Chemical group 0.000 abstract description 38
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 21
- 125000005842 heteroatom Chemical group 0.000 abstract description 19
- 229910052731 fluorine Inorganic materials 0.000 abstract description 15
- 229910052801 chlorine Inorganic materials 0.000 abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 abstract description 13
- 229910052794 bromium Inorganic materials 0.000 abstract description 12
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 abstract description 12
- 125000003118 aryl group Chemical group 0.000 abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 9
- 229910052799 carbon Inorganic materials 0.000 abstract description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 5
- 239000000758 substrate Substances 0.000 abstract description 5
- 125000004429 atom Chemical group 0.000 abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 150000001602 bicycloalkyls Chemical group 0.000 abstract description 2
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 229910052740 iodine Inorganic materials 0.000 abstract 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 1
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 abstract 1
- 125000003003 spiro group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 description 137
- 239000000543 intermediate Substances 0.000 description 94
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- 238000001819 mass spectrum Methods 0.000 description 66
- 239000000203 mixture Substances 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 150000004702 methyl esters Chemical class 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 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 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 239000007832 Na2SO4 Substances 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000003643 water by type Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical class N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- RNXQQZNOSYBFTN-VIFPVBQESA-N (1s)-4-bromo-2,3-dihydro-1h-inden-1-ol Chemical compound C1=CC=C(Br)C2=C1[C@@H](O)CC2 RNXQQZNOSYBFTN-VIFPVBQESA-N 0.000 description 4
- XGXRWHAYNFAHBM-ZCFIWIBFSA-N 2-[(3s)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound OC1=CC=C2[C@H](CC(=O)O)COC2=C1 XGXRWHAYNFAHBM-ZCFIWIBFSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 102100026148 Free fatty acid receptor 1 Human genes 0.000 description 4
- 101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 125000002757 morpholinyl group Chemical group 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 125000003566 oxetanyl group Chemical group 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-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
- 239000000443 aerosol Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000012039 electrophile Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
- JAICRPHZHDNVQL-SECBINFHSA-N (1r)-6-(trifluoromethyl)-2,3-dihydro-1h-inden-1-ol Chemical compound C1=C(C(F)(F)F)C=C2[C@H](O)CCC2=C1 JAICRPHZHDNVQL-SECBINFHSA-N 0.000 description 2
- DXVPKKRFBPLRRN-SECBINFHSA-N (1r)-6-bromo-2,3-dihydro-1h-inden-1-ol Chemical compound C1=C(Br)C=C2[C@H](O)CCC2=C1 DXVPKKRFBPLRRN-SECBINFHSA-N 0.000 description 2
- DKONDGLWLXRZGO-QRWMCTBCSA-N (1s)-1-[1-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydro-1h-inden-4-yl]-2,2-dimethylpropan-1-ol Chemical compound CC(C)(C)[C@H](O)C1=CC=CC2=C1CCC2O[Si](C)(C)C(C)(C)C DKONDGLWLXRZGO-QRWMCTBCSA-N 0.000 description 2
- PWUYJTDRMLHWKF-HNNXBMFYSA-N (1s)-1-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydro-1h-indene-4-carbonitrile Chemical compound C1=CC=C(C#N)C2=C1[C@@H](O[Si](C)(C)C(C)(C)C)CC2 PWUYJTDRMLHWKF-HNNXBMFYSA-N 0.000 description 2
- MEFZMTYUOQFQHF-JTQLQIEISA-N (1s)-1-hydroxy-2,3-dihydro-1h-indene-4-carbonitrile Chemical compound C1=CC=C(C#N)C2=C1[C@@H](O)CC2 MEFZMTYUOQFQHF-JTQLQIEISA-N 0.000 description 2
- XYANGZGKLJBDRT-VIFPVBQESA-N (1s)-4-(1,1,2,2,2-pentafluoroethyl)-2,3-dihydro-1h-inden-1-ol Chemical compound C1=CC=C(C(F)(F)C(F)(F)F)C2=C1[C@@H](O)CC2 XYANGZGKLJBDRT-VIFPVBQESA-N 0.000 description 2
- OQHOANBYHVKCAO-LBPRGKRZSA-N (1s)-4-(1,1-difluoro-2-methoxy-2-methylpropyl)-2,3-dihydro-1h-inden-1-ol Chemical compound COC(C)(C)C(F)(F)C1=CC=CC2=C1CC[C@@H]2O OQHOANBYHVKCAO-LBPRGKRZSA-N 0.000 description 2
- UAGDXBOCSUHXET-ZDUSSCGKSA-N (1s)-4-(2,2-dimethylpropyl)-2,3-dihydro-1h-inden-1-ol Chemical compound CC(C)(C)CC1=CC=CC2=C1CC[C@@H]2O UAGDXBOCSUHXET-ZDUSSCGKSA-N 0.000 description 2
- ZXCNSEXMBFABBI-LBAUFKAWSA-N (1s)-4-(2-methoxy-3,3-dimethylbutan-2-yl)-2,3-dihydro-1h-inden-1-ol Chemical compound COC(C)(C(C)(C)C)C1=CC=CC2=C1CC[C@@H]2O ZXCNSEXMBFABBI-LBAUFKAWSA-N 0.000 description 2
- YZUOSZWXZGCIHX-SFHVURJKSA-N (1s)-4-(2-propan-2-ylphenyl)-2,3-dihydro-1h-inden-1-ol Chemical compound CC(C)C1=CC=CC=C1C1=CC=CC2=C1CC[C@@H]2O YZUOSZWXZGCIHX-SFHVURJKSA-N 0.000 description 2
- VSIKRNKEFUIRSW-QMMMGPOBSA-N (1s)-4-(trifluoromethoxy)-2,3-dihydro-1h-inden-1-ol Chemical compound C1=CC=C(OC(F)(F)F)C2=C1[C@@H](O)CC2 VSIKRNKEFUIRSW-QMMMGPOBSA-N 0.000 description 2
- IDHGYOQGMVANDO-VIFPVBQESA-N (1s)-4-chloro-2,3-dihydro-1h-inden-1-ol Chemical compound C1=CC=C(Cl)C2=C1[C@@H](O)CC2 IDHGYOQGMVANDO-VIFPVBQESA-N 0.000 description 2
- IGMZTSAXNSAYIY-LBPRGKRZSA-N (1s)-4-cyclopropyl-2,3-dihydro-1h-inden-1-ol Chemical compound C([C@@H]1O)CC2=C1C=CC=C2C1CC1 IGMZTSAXNSAYIY-LBPRGKRZSA-N 0.000 description 2
- JAWQVIMTFOFMOH-ZDUSSCGKSA-N (1s)-4-morpholin-4-yl-2,3-dihydro-1h-inden-1-ol Chemical compound C([C@@H]1O)CC2=C1C=CC=C2N1CCOCC1 JAWQVIMTFOFMOH-ZDUSSCGKSA-N 0.000 description 2
- HTZPALFSQCZAFO-INIZCTEOSA-N (1s)-5-(2,6-dimethylphenyl)-2,3-dihydro-1h-inden-1-ol Chemical compound CC1=CC=CC(C)=C1C1=CC=C([C@@H](O)CC2)C2=C1 HTZPALFSQCZAFO-INIZCTEOSA-N 0.000 description 2
- FLQUVMBVTFSJRY-VIFPVBQESA-N (1s)-5-(trifluoromethyl)-2,3-dihydro-1h-inden-1-ol Chemical compound FC(F)(F)C1=CC=C2[C@@H](O)CCC2=C1 FLQUVMBVTFSJRY-VIFPVBQESA-N 0.000 description 2
- DRXIUUZVRAOHBS-VIFPVBQESA-N (1s)-5-bromo-2,3-dihydro-1h-inden-1-ol Chemical compound BrC1=CC=C2[C@@H](O)CCC2=C1 DRXIUUZVRAOHBS-VIFPVBQESA-N 0.000 description 2
- WDXUNFVYUDYDQA-VIFPVBQESA-N (1s)-5-chloro-2,3-dihydro-1h-inden-1-ol Chemical compound ClC1=CC=C2[C@@H](O)CCC2=C1 WDXUNFVYUDYDQA-VIFPVBQESA-N 0.000 description 2
- JAICRPHZHDNVQL-VIFPVBQESA-N (1s)-6-(trifluoromethyl)-2,3-dihydro-1h-inden-1-ol Chemical compound C1=C(C(F)(F)F)C=C2[C@@H](O)CCC2=C1 JAICRPHZHDNVQL-VIFPVBQESA-N 0.000 description 2
- RQKILQSITWCOKV-JTQLQIEISA-N (1s)-6-methyl-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-ol Chemical compound FC(F)(F)C1=CC(C)=CC2=C1CC[C@@H]2O RQKILQSITWCOKV-JTQLQIEISA-N 0.000 description 2
- MDXMTZYIFQCSHB-QMMMGPOBSA-N (1s)-7-(trifluoromethyl)-2,3-dihydro-1h-inden-1-ol Chemical compound C1=CC(C(F)(F)F)=C2[C@@H](O)CCC2=C1 MDXMTZYIFQCSHB-QMMMGPOBSA-N 0.000 description 2
- WTFIVWOOPIQVJR-QMMMGPOBSA-N (1s)-7-fluoro-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-ol Chemical compound FC1=CC=C(C(F)(F)F)C2=C1[C@@H](O)CC2 WTFIVWOOPIQVJR-QMMMGPOBSA-N 0.000 description 2
- WTTSHUTYXBNHJJ-VIFPVBQESA-N (1s)-7-methyl-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-ol Chemical compound CC1=CC=C(C(F)(F)F)C2=C1[C@@H](O)CC2 WTTSHUTYXBNHJJ-VIFPVBQESA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- JKFCMPFVUYZBBW-XJDOXCRVSA-N 1-[(1s)-1-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydro-1h-inden-4-yl]-2,2-dimethylpent-4-en-1-ol Chemical compound C1=CC=C(C(O)C(C)(C)CC=C)C2=C1[C@@H](O[Si](C)(C)C(C)(C)C)CC2 JKFCMPFVUYZBBW-XJDOXCRVSA-N 0.000 description 2
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- FHQOPBXDKDDFEH-FZKQIMNGSA-N methyl 2-[(3s)-6-[[(1r)-5-chloro-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC(Cl)=CC=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 FHQOPBXDKDDFEH-FZKQIMNGSA-N 0.000 description 1
- ZWTJDKXZTWDXOM-ADLMAVQZSA-N methyl 2-[(3s)-6-[[(1r)-6-fluoro-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC(F)=C2)C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 ZWTJDKXZTWDXOM-ADLMAVQZSA-N 0.000 description 1
- UTMXAHNVISUDNE-BFUOFWGJSA-N methyl 2-[(3s)-6-[[(1r)-6-methyl-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC(C)=C2)C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 UTMXAHNVISUDNE-BFUOFWGJSA-N 0.000 description 1
- SUYFGCQOXWMPBO-CXAGYDPISA-N methyl 2-[(3s)-6-[[(1r)-7-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC=CC(C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 SUYFGCQOXWMPBO-CXAGYDPISA-N 0.000 description 1
- FSZJMHGMTWAEIT-FZKQIMNGSA-N methyl 2-[(3s)-6-[[(1r)-7-methyl-4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2C)C(F)(F)F)=C2[C@@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 FSZJMHGMTWAEIT-FZKQIMNGSA-N 0.000 description 1
- JCTSMAOMLOEEET-ACJLOTCBSA-N methyl 2-[(3s)-6-[[(1s)-6-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC=C(C(F)(F)F)C=C2[C@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 JCTSMAOMLOEEET-ACJLOTCBSA-N 0.000 description 1
- BQGLBAUIXKRBHU-ACJLOTCBSA-N methyl 2-[(3s)-6-[[(1s)-6-bromo-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC2=CC=C(Br)C=C2[C@H]1OC1=CC=C2[C@H](CC(=O)OC)COC2=C1 BQGLBAUIXKRBHU-ACJLOTCBSA-N 0.000 description 1
- GMQKWFJVQAVOIB-ZZAPORBBSA-N methyl 2-[6-[[(1r)-4-(1-methylpyrazol-4-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OCC(C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C=1C=NN(C)C=1 GMQKWFJVQAVOIB-ZZAPORBBSA-N 0.000 description 1
- DBDVGDAIGQYMKV-IXXGTQFESA-N methyl 2-[6-[[(1r)-4-(4-methoxyphenyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C([C@H]1OC=2C=C3OCC(C3=CC=2)CC(=O)OC)CC2=C1C=CC=C2C1=CC=C(OC)C=C1 DBDVGDAIGQYMKV-IXXGTQFESA-N 0.000 description 1
- SQBMIZXNWXOQHS-UHFFFAOYSA-N methyl 2-[6-[[4-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound C1CC(C(=CC=C2)C(F)(F)F)=C2C1OC1=CC=C2C(CC(=O)OC)COC2=C1 SQBMIZXNWXOQHS-UHFFFAOYSA-N 0.000 description 1
- UZKXUKZPWZVIMC-UHFFFAOYSA-N methyl 3-[2-(1,1,2,2,2-pentafluoroethyl)phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1C(F)(F)C(F)(F)F UZKXUKZPWZVIMC-UHFFFAOYSA-N 0.000 description 1
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- 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
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- GYMHCIVSCUPNPV-OYKVQYDMSA-N tert-butyl-[[(1s)-4-(1-methoxy-2,2-dimethylpropyl)-2,3-dihydro-1h-inden-1-yl]oxy]-dimethylsilane Chemical compound COC(C(C)(C)C)C1=CC=CC2=C1CC[C@@H]2O[Si](C)(C)C(C)(C)C GYMHCIVSCUPNPV-OYKVQYDMSA-N 0.000 description 1
- KHCJHFNAEVOTDV-YDNXMHBPSA-N tert-butyl-[[(1s)-4-(2-methoxy-3,3-dimethylbutan-2-yl)-2,3-dihydro-1h-inden-1-yl]oxy]-dimethylsilane Chemical compound COC(C)(C(C)(C)C)C1=CC=CC2=C1CC[C@@H]2O[Si](C)(C)C(C)(C)C KHCJHFNAEVOTDV-YDNXMHBPSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- 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
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- 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
-
- 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
-
- 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
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10193382 | 2010-12-01 | ||
| EP10193382 | 2010-12-01 | ||
| EP11154999 | 2011-02-18 | ||
| EP11154999 | 2011-02-18 | ||
| EP11175646 | 2011-07-27 | ||
| EP11175646 | 2011-07-27 | ||
| PCT/EP2011/071410 WO2012072691A1 (en) | 2010-12-01 | 2011-11-30 | Indanyloxydihydrobenzofuranylacetic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2546154T3 true ES2546154T3 (es) | 2015-09-21 |
Family
ID=45063142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11788845.3T Active ES2546154T3 (es) | 2010-12-01 | 2011-11-30 | Ácidos indaniloxidihidrobenzofuranilacéticos, útiles para el tratamiento del síndrome metabólico |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20120302566A1 (enExample) |
| EP (1) | EP2646425B1 (enExample) |
| JP (1) | JP5853317B2 (enExample) |
| AR (1) | AR084050A1 (enExample) |
| DK (1) | DK2646425T3 (enExample) |
| ES (1) | ES2546154T3 (enExample) |
| HU (1) | HUE025363T2 (enExample) |
| PL (1) | PL2646425T3 (enExample) |
| UY (1) | UY33758A (enExample) |
| WO (1) | WO2012072691A1 (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US8642585B2 (en) * | 2012-03-26 | 2014-02-04 | Boehringer Ingelheim International Gmbh | Indanyloxydihydrobenzofuranylacetic acids |
| US8809376B2 (en) * | 2012-04-30 | 2014-08-19 | Boehringer Ingelheim International Gmbh | Indanyloxydihydrobenzofuranylacetic acids |
| EP2872127A1 (en) | 2012-07-11 | 2015-05-20 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| KR20150088878A (ko) | 2012-11-28 | 2015-08-03 | 베링거 인겔하임 인터내셔날 게엠베하 | 신규한 인다닐옥시디하이드로벤조푸라닐아세트산 |
| EP2928886B1 (en) | 2012-12-07 | 2016-11-02 | Boehringer Ingelheim International GmbH | New indanyloxydihydrobenzofuranylacetic acids |
| EP2953681B1 (en) | 2013-02-06 | 2017-03-15 | Boehringer Ingelheim International GmbH | New indanyloxydihydrobenzofuranylacetic acids |
| JP2016516004A (ja) | 2013-02-22 | 2016-06-02 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | 抗糖尿病二環式化合物 |
| WO2015024526A1 (en) * | 2013-08-23 | 2015-02-26 | Fujian Haixi Pharmaceuticals Co., Ltd | Carboxylic acid compounds in treatment of diabetes mellitus |
| WO2015044073A1 (en) * | 2013-09-26 | 2015-04-02 | Boehringer Ingelheim International Gmbh | Process and intermediates for preparing indanyloxydihydrobenzofuranyl acetic acid derivatives as gpr40 agonists |
| US10519115B2 (en) | 2013-11-15 | 2019-12-31 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| EP3074375B1 (en) * | 2013-11-28 | 2018-04-04 | Boehringer Ingelheim International GmbH | New indanyloxyphenylcyclopropanecarboxylic acids |
| EP3076959B1 (en) | 2013-12-04 | 2018-07-04 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| WO2015119899A1 (en) | 2014-02-06 | 2015-08-13 | Merck Sharp & Dohme Corp. | Antidiabetic compounds |
| CN105001212B (zh) * | 2014-04-16 | 2018-01-16 | 江苏柯菲平医药股份有限公司 | 稠环化合物及其制备方法和应用 |
| WO2015176267A1 (en) | 2014-05-22 | 2015-11-26 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2016022742A1 (en) | 2014-08-08 | 2016-02-11 | 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 |
| WO2016022448A1 (en) | 2014-08-08 | 2016-02-11 | 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 |
| CN104177320B (zh) * | 2014-08-27 | 2016-03-02 | 广东东阳光药业有限公司 | 一种脲取代联苯类化合物及其组合物及用途 |
| US10676458B2 (en) | 2016-03-29 | 2020-06-09 | Merch Sharp & Dohne Corp. Rahway | Antidiabetic bicyclic compounds |
| WO2018106518A1 (en) | 2016-12-06 | 2018-06-14 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| KR102007633B1 (ko) * | 2016-12-15 | 2019-08-06 | 일동제약(주) | 신규 페닐 프로피온 산 유도체 및 이의 용도 |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| CN110198928B (zh) | 2017-01-26 | 2023-08-29 | 勃林格殷格翰国际有限公司 | 苄氧基吡啶基环丙烷甲酸、其药物组合物和用途 |
| EP3573952B1 (en) | 2017-01-26 | 2021-07-14 | Boehringer Ingelheim International GmbH | Benzylaminopyridylcyclopropanecarboxylic acids, pharmaceuticalcompositions and uses thereof |
| WO2018138028A1 (en) | 2017-01-26 | 2018-08-02 | Boehringer Ingelheim International Gmbh | Benzylaminopyrazinylcyclopropanecarboxylic acids, pharmaceutical compositions and uses thereof |
| WO2018138030A1 (en) | 2017-01-26 | 2018-08-02 | Boehringer Ingelheim International Gmbh | Benzyloxypyrazinylcyclopropanecarboxylic acids, pharmaceutical compositions and uses thereof |
| EP3580222B1 (en) | 2017-02-08 | 2021-04-07 | Boehringer Ingelheim International GmbH | Indanylaminoazadihydrobenzofuranylacetic acids, pharmaceutical compositions for the treatment of diabetes |
| EP3709995A4 (en) | 2017-11-16 | 2021-04-14 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| SI3752501T1 (sl) | 2018-02-13 | 2023-08-31 | Gilead Sciences, Inc. | Inhibitorji pd-1/pd-l1 |
| CA3093130C (en) | 2018-04-19 | 2023-10-17 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| SI3820572T1 (sl) | 2018-07-13 | 2023-12-29 | Gilead Sciences, Inc. | Inhibitorji pd-1/pd-l1 |
| JP7158577B2 (ja) | 2018-10-24 | 2022-10-21 | ギリアード サイエンシーズ, インコーポレイテッド | Pd-1/pd-l1阻害剤 |
| JP2022552655A (ja) | 2019-10-07 | 2022-12-19 | キャリーオペ,インク. | Gpr119アゴニスト |
| TW202140440A (zh) | 2020-02-28 | 2021-11-01 | 美商克力歐普股份有限公司 | Gpr40激動劑 |
| AU2021275038A1 (en) | 2020-05-19 | 2022-12-22 | Kallyope, Inc. | AMPK activators |
| CA3183575A1 (en) | 2020-06-26 | 2021-12-30 | Iyassu Sebhat | Ampk activators |
| JP2024524246A (ja) * | 2021-06-23 | 2024-07-05 | ブループリント メディシンズ コーポレイション | Egfr阻害剤を調製するための方法 |
| WO2025140655A1 (en) * | 2023-12-30 | 2025-07-03 | Fujian Haixi Pharmaceuticals Co., Ltd. | Heteroaryl compounds as multi-target protein kinase inhibitors |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2628103B1 (fr) | 1988-03-03 | 1991-06-14 | Roussel Uclaf | Nouveaux esters pyrethrinoides portant un noyau indanyle, leur procede de preparation et leur application comme pesticides |
| JP4594611B2 (ja) * | 2002-11-08 | 2010-12-08 | 武田薬品工業株式会社 | 受容体機能調節剤 |
| US7960369B2 (en) | 2002-11-08 | 2011-06-14 | Takeda Pharmaceutical Company Limited | Receptor function regulator |
| JP4805552B2 (ja) * | 2003-05-30 | 2011-11-02 | 武田薬品工業株式会社 | 縮合環化合物 |
| US7446216B2 (en) | 2004-12-16 | 2008-11-04 | Exxonmobil Chemical Patents Inc. | Halogen substituted metallocene compounds for olefin polymerization |
| CA2621949A1 (en) | 2005-09-14 | 2007-03-22 | Amgen Inc. | Conformationally constrained 3- (4-hydroxy-phenyl) - substituted-propanoic acids useful for treating metabolic disorders |
| EP2006271A4 (en) * | 2006-03-30 | 2011-08-10 | Asahi Kasei Pharma Corp | SUBSTITUTED BICYCLIC CYCLIC DERIVATIVE AND USE THEREOF |
| CL2007001873A1 (es) | 2006-06-27 | 2008-01-04 | Takeda Pharmaceutical | Acido((3s))-6-((¨2,6-dimetil-4-(3-(metilsulfonil)-propoxi)bifenil-3-il)metoxi-2,3-dihidro-1-benzofuran-3-il)acetico o una sal del mismo |
| WO2008054675A2 (en) * | 2006-10-31 | 2008-05-08 | Merck & Co., Inc. | Antidiabetic bicyclic compounds |
| CA2727340A1 (en) * | 2008-06-25 | 2009-12-30 | Daiichi Sankyo Company, Limited | Carboxylic acid compound |
| JP5551707B2 (ja) * | 2008-10-15 | 2014-07-16 | アムジエン・インコーポレーテツド | スピロ環gpr40調節因子 |
| EP2440541A1 (en) * | 2009-06-09 | 2012-04-18 | Takeda Pharmaceutical Company Limited | Novel fused cyclic compound and use thereof |
| US8642585B2 (en) * | 2012-03-26 | 2014-02-04 | Boehringer Ingelheim International Gmbh | Indanyloxydihydrobenzofuranylacetic acids |
-
2011
- 2011-11-30 PL PL11788845T patent/PL2646425T3/pl unknown
- 2011-11-30 UY UY0001033758A patent/UY33758A/es not_active Application Discontinuation
- 2011-11-30 ES ES11788845.3T patent/ES2546154T3/es active Active
- 2011-11-30 AR ARP110104457A patent/AR084050A1/es unknown
- 2011-11-30 WO PCT/EP2011/071410 patent/WO2012072691A1/en not_active Ceased
- 2011-11-30 DK DK11788845.3T patent/DK2646425T3/en active
- 2011-11-30 HU HUE11788845A patent/HUE025363T2/en unknown
- 2011-11-30 US US13/307,455 patent/US20120302566A1/en not_active Abandoned
- 2011-11-30 EP EP11788845.3A patent/EP2646425B1/en not_active Not-in-force
- 2011-11-30 JP JP2013541333A patent/JP5853317B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2646425A1 (en) | 2013-10-09 |
| EP2646425B1 (en) | 2015-06-10 |
| UY33758A (es) | 2012-06-29 |
| US20120302566A1 (en) | 2012-11-29 |
| PL2646425T3 (pl) | 2015-12-31 |
| DK2646425T3 (en) | 2015-08-24 |
| WO2012072691A1 (en) | 2012-06-07 |
| AR084050A1 (es) | 2013-04-17 |
| JP2013544268A (ja) | 2013-12-12 |
| JP5853317B2 (ja) | 2016-02-09 |
| HUE025363T2 (en) | 2016-02-29 |
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