CN103083307A - 稠环化合物 - Google Patents
稠环化合物 Download PDFInfo
- Publication number
- CN103083307A CN103083307A CN2012105303764A CN201210530376A CN103083307A CN 103083307 A CN103083307 A CN 103083307A CN 2012105303764 A CN2012105303764 A CN 2012105303764A CN 201210530376 A CN201210530376 A CN 201210530376A CN 103083307 A CN103083307 A CN 103083307A
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- Prior art keywords
- compound
- methyl
- group
- alkyl
- dimethyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 373
- 239000003814 drug Substances 0.000 claims abstract description 65
- 150000003839 salts Chemical class 0.000 claims abstract description 63
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 25
- 102100026148 Free fatty acid receptor 1 Human genes 0.000 claims abstract description 22
- 101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 0.000 claims abstract description 22
- 229940079593 drug Drugs 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 77
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 65
- 125000005843 halogen group Chemical group 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 47
- 238000002360 preparation method Methods 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound 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 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 238000006722 reduction reaction Methods 0.000 claims description 13
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 10
- 108090001061 Insulin Proteins 0.000 claims description 10
- 229940100389 Sulfonylurea Drugs 0.000 claims description 10
- 229940125396 insulin Drugs 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 7
- 229960000698 nateglinide Drugs 0.000 claims description 6
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 claims description 6
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 6
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 5
- 229940123208 Biguanide Drugs 0.000 claims description 5
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 5
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 5
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 5
- 159000000007 calcium salts Chemical class 0.000 claims description 5
- XGXRWHAYNFAHBM-UHFFFAOYSA-N 2-(6-hydroxy-2,3-dihydro-1-benzofuran-3-yl)acetic acid Chemical compound OC1=CC=C2C(CC(=O)O)COC2=C1 XGXRWHAYNFAHBM-UHFFFAOYSA-N 0.000 claims description 4
- 229960004580 glibenclamide Drugs 0.000 claims description 4
- 229960004346 glimepiride Drugs 0.000 claims description 4
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 claims description 4
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 claims description 4
- 229960003365 mitiglinide Drugs 0.000 claims description 4
- WPGGHFDDFPHPOB-BBWFWOEESA-N mitiglinide Chemical compound C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)O)C1=CC=CC=C1 WPGGHFDDFPHPOB-BBWFWOEESA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 4
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 4
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 3
- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical group OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 claims description 3
- ZSBOMTDTBDDKMP-OAHLLOKOSA-N alogliptin Chemical group C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZSBOMTDTBDDKMP-OAHLLOKOSA-N 0.000 claims description 3
- 229960001667 alogliptin Drugs 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 150000004283 biguanides Chemical class 0.000 claims description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 3
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical group CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 3
- 229960003105 metformin Drugs 0.000 claims description 3
- 229960005095 pioglitazone Drugs 0.000 claims description 3
- 229960001729 voglibose Drugs 0.000 claims description 3
- BPLHYJUFAJGXNJ-UHFFFAOYSA-N 4-[3-(hydroxymethyl)phenyl]-2,3,5,6-tetramethylphenol Chemical compound CC1=C(O)C(C)=C(C)C(C=2C=C(CO)C=CC=2)=C1C BPLHYJUFAJGXNJ-UHFFFAOYSA-N 0.000 claims description 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 2
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960005370 atorvastatin Drugs 0.000 claims description 2
- 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 claims 4
- 239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- XVTKVGIZQCELOW-RUZDIDTESA-N 2-[(3s)-6-[[3-[2,6-diethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound CCC1=CC(OCCCS(C)(=O)=O)=CC(CC)=C1C1=CC=CC(COC=2C=C3OC[C@@H](CC(O)=O)C3=CC=2)=C1 XVTKVGIZQCELOW-RUZDIDTESA-N 0.000 claims 1
- LEQBIYIYFWBWEQ-OAQYLSRUSA-N 2-[(3s)-6-[[3-[3,5-dichloro-2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound CC1=C(Cl)C(OCCCS(C)(=O)=O)=C(Cl)C(C)=C1C1=CC=CC(COC=2C=C3OC[C@@H](CC(O)=O)C3=CC=2)=C1 LEQBIYIYFWBWEQ-OAQYLSRUSA-N 0.000 claims 1
- SMQHICHIKHDWQK-JOCHJYFZSA-N 2-[(3s)-6-[[3-[3-chloro-2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound CC1=CC(OCCCS(C)(=O)=O)=C(Cl)C(C)=C1C1=CC=CC(COC=2C=C3OC[C@@H](CC(O)=O)C3=CC=2)=C1 SMQHICHIKHDWQK-JOCHJYFZSA-N 0.000 claims 1
- TZRMVMQZTUFNGG-JOCHJYFZSA-N 2-[(3s)-6-[[3-[3-fluoro-2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound CC1=CC(OCCCS(C)(=O)=O)=C(F)C(C)=C1C1=CC=CC(COC=2C=C3OC[C@@H](CC(O)=O)C3=CC=2)=C1 TZRMVMQZTUFNGG-JOCHJYFZSA-N 0.000 claims 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 claims 1
- GIPNZBATXCUTDZ-UHFFFAOYSA-N 4-(4-bromo-3,5-dimethylphenoxy)thiane Chemical compound CC1=C(Br)C(C)=CC(OC2CCSCC2)=C1 GIPNZBATXCUTDZ-UHFFFAOYSA-N 0.000 claims 1
- BZCALJIHZVNMGJ-HSZRJFAPSA-N Fasiglifam Chemical compound CC1=CC(OCCCS(C)(=O)=O)=CC(C)=C1C1=CC=CC(COC=2C=C3OC[C@@H](CC(O)=O)C3=CC=2)=C1 BZCALJIHZVNMGJ-HSZRJFAPSA-N 0.000 claims 1
- 102100023915 Insulin Human genes 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- DWBKKABOJCRZJE-UHFFFAOYSA-N methyl 3-[2,6-dimethyl-4-(thian-4-yloxy)phenyl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C(=CC(OC3CCSCC3)=CC=2C)C)=C1 DWBKKABOJCRZJE-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- IWYJYHUNXVAVAA-OAHLLOKOSA-N trelagliptin Chemical group C=1C(F)=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 IWYJYHUNXVAVAA-OAHLLOKOSA-N 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 abstract description 10
- 239000000651 prodrug Substances 0.000 abstract description 10
- 229940122199 Insulin secretagogue Drugs 0.000 abstract description 8
- 230000001105 regulatory effect Effects 0.000 abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 356
- -1 heterocyclic radical Chemical class 0.000 description 332
- 239000000203 mixture Substances 0.000 description 221
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 200
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 173
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 158
- 239000000243 solution Substances 0.000 description 113
- 239000002585 base Substances 0.000 description 110
- 230000002829 reductive effect Effects 0.000 description 88
- 238000002425 crystallisation Methods 0.000 description 85
- 230000008025 crystallization Effects 0.000 description 85
- 239000000376 reactant Substances 0.000 description 80
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 79
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 74
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 63
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 61
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- 238000001035 drying Methods 0.000 description 56
- 235000011054 acetic acid Nutrition 0.000 description 54
- 229910052757 nitrogen Inorganic materials 0.000 description 54
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 54
- 238000005406 washing Methods 0.000 description 54
- 238000003756 stirring Methods 0.000 description 52
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 48
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 47
- 238000010898 silica gel chromatography Methods 0.000 description 47
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- 239000002904 solvent Substances 0.000 description 39
- 229910052760 oxygen Inorganic materials 0.000 description 34
- 239000001301 oxygen Substances 0.000 description 33
- 239000012230 colorless oil Substances 0.000 description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000012046 mixed solvent Substances 0.000 description 27
- 235000011121 sodium hydroxide Nutrition 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000007864 aqueous solution Substances 0.000 description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 26
- 239000003795 chemical substances by application Substances 0.000 description 26
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 24
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 22
- 239000008103 glucose Substances 0.000 description 22
- 230000003287 optical effect Effects 0.000 description 22
- 238000001556 precipitation Methods 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000003513 alkali Substances 0.000 description 21
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 17
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 17
- 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 17
- 125000000623 heterocyclic group Chemical group 0.000 description 16
- 239000003112 inhibitor Substances 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 15
- 150000003851 azoles Chemical class 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 238000013459 approach Methods 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 201000010099 disease Diseases 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 13
- 206010056997 Impaired fasting glucose Diseases 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 229910052783 alkali metal Inorganic materials 0.000 description 13
- 230000006870 function Effects 0.000 description 13
- 150000003053 piperidines Chemical class 0.000 description 13
- 125000000547 substituted alkyl group Chemical group 0.000 description 13
- KFKSIUOALVIACE-UHFFFAOYSA-N 3-phenylbenzaldehyde Chemical compound O=CC1=CC=CC(C=2C=CC=CC=2)=C1 KFKSIUOALVIACE-UHFFFAOYSA-N 0.000 description 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 12
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 12
- 239000004327 boric acid Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 235000011181 potassium carbonates Nutrition 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 11
- 238000010586 diagram Methods 0.000 description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- 230000002265 prevention Effects 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
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Classifications
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Landscapes
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| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP2205548A1 (en) | 2007-10-10 | 2010-07-14 | Amgen, Inc | Substituted biphenyl gpr40 modulators |
| CA2716352C (en) * | 2008-03-06 | 2013-05-28 | Amgen Inc. | Conformationally constrained carboxylic acid derivatives useful for treating metabolic disorders |
| WO2009117421A2 (en) * | 2008-03-17 | 2009-09-24 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| US8586607B2 (en) | 2008-07-28 | 2013-11-19 | Syddansk Universitet | Compounds for the treatment of metabolic diseases |
| TW201014850A (en) | 2008-09-25 | 2010-04-16 | Takeda Pharmaceutical | Solid pharmaceutical composition |
| EP2358656B1 (en) | 2008-10-15 | 2014-01-01 | Amgen, Inc | Spirocyclic gpr40 modulators |
| JP5535931B2 (ja) | 2008-10-27 | 2014-07-02 | 武田薬品工業株式会社 | 二環性化合物 |
| AR074760A1 (es) * | 2008-12-18 | 2011-02-09 | Metabolex Inc | Agonistas del receptor gpr120 y usos de los mismos en medicamentos para el tratamiento de diabetes y el sindrome metabolico. |
| WO2010076884A1 (ja) | 2008-12-29 | 2010-07-08 | 武田薬品工業株式会社 | 新規縮合環化合物およびその用途 |
| AR075158A1 (es) | 2009-01-27 | 2011-03-16 | Takeda Pharmaceutical | Derivados de pirrolopirimidinas, composiciones farmaceuticas y usos. |
| US20120035196A1 (en) | 2009-04-22 | 2012-02-09 | Kenji Negoro | Carboxylic acid compound |
| US20120172351A1 (en) | 2009-06-09 | 2012-07-05 | Nobuyuki Negoro | Novel fused cyclic compound and use thereof |
| AU2010279171A1 (en) | 2009-07-28 | 2012-03-01 | Takeda Pharmaceutical Company Limited | Tablet |
| EP2495238A4 (en) | 2009-10-30 | 2013-04-24 | Mochida Pharm Co Ltd | NEW 3-HYDROXY-5-ARYLISOXAZOLE DERIVATIVE |
| US8476287B2 (en) | 2009-12-25 | 2013-07-02 | Mochida Pharmaceutical Co., Ltd. | 3-hydroxy-5-arylisothiazole derivative |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
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| BR112012032055B8 (pt) | 2010-06-16 | 2019-11-12 | Takeda Pharmaceuticals Co | cristal de cloridrato de 1-(4-metoxibutil)-n-(2-metilpropil)-n-[(3s,5r)-5-(morfolin-4-ilcarbonil)piperidin-3-il]-1h-benzimidazol-2-carboxamida, medicamento, e, uso do cristal |
| US8299117B2 (en) | 2010-06-16 | 2012-10-30 | Metabolex Inc. | GPR120 receptor agonists and uses thereof |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
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| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| JP5816626B2 (ja) | 2010-09-17 | 2015-11-18 | 武田薬品工業株式会社 | 糖尿病治療剤 |
| JP5809157B2 (ja) | 2010-10-08 | 2015-11-10 | 持田製薬株式会社 | 環状アミド誘導体 |
| AR084032A1 (es) | 2010-11-30 | 2013-04-17 | Takeda Pharmaceutical | Compuesto biciclico |
| AR084050A1 (es) | 2010-12-01 | 2013-04-17 | Boehringer Ingelheim Int | Acidos indaniloxidihidrobenzofuranilaceticos |
| WO2014011926A1 (en) | 2012-07-11 | 2014-01-16 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| AU2012218401A1 (en) | 2011-02-17 | 2013-09-05 | Takeda Pharmaceutical Company Limited | Production method of optically active dihydrobenzofuran derivative |
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