TW201206911A - Bicyclic compound - Google Patents
Bicyclic compound Download PDFInfo
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- TW201206911A TW201206911A TW100114410A TW100114410A TW201206911A TW 201206911 A TW201206911 A TW 201206911A TW 100114410 A TW100114410 A TW 100114410A TW 100114410 A TW100114410 A TW 100114410A TW 201206911 A TW201206911 A TW 201206911A
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- -1 Bicyclic compound Chemical class 0.000 title description 218
- 150000001875 compounds Chemical class 0.000 claims abstract description 764
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 32
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 26
- 208000008589 Obesity Diseases 0.000 claims abstract description 20
- 235000020824 obesity Nutrition 0.000 claims abstract description 20
- 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 17
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 17
- 201000011510 cancer Diseases 0.000 claims abstract description 15
- 208000002249 Diabetes Complications Diseases 0.000 claims abstract description 14
- 206010020772 Hypertension Diseases 0.000 claims abstract description 14
- 206010012655 Diabetic complications Diseases 0.000 claims abstract description 13
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 13
- 206010019280 Heart failures Diseases 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims description 176
- 238000000034 method Methods 0.000 claims description 143
- 125000000217 alkyl group Chemical group 0.000 claims description 142
- 125000005843 halogen group Chemical group 0.000 claims description 103
- 150000003839 salts Chemical class 0.000 claims description 80
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 75
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
- 125000003545 alkoxy group Chemical group 0.000 claims description 59
- 125000000623 heterocyclic group Chemical group 0.000 claims description 56
- 239000003795 chemical substances by application Substances 0.000 claims description 54
- 125000004429 atom Chemical group 0.000 claims description 53
- 238000004519 manufacturing process Methods 0.000 claims description 48
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- 239000003814 drug Substances 0.000 claims description 42
- 125000003277 amino group Chemical class 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 18
- 229940124597 therapeutic agent Drugs 0.000 claims description 18
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 239000007789 gas Substances 0.000 claims description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 9
- 210000002027 skeletal muscle Anatomy 0.000 claims description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 239000008177 pharmaceutical agent Substances 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 230000003449 preventive effect Effects 0.000 claims description 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical group C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 239000010931 gold Substances 0.000 claims description 3
- 230000004060 metabolic process Effects 0.000 claims description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002532 enzyme inhibitor Substances 0.000 claims description 2
- 229940125532 enzyme inhibitor Drugs 0.000 claims description 2
- STHHLVCQSLRQNI-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octane Chemical compound C1C2CCN1CCC2 STHHLVCQSLRQNI-UHFFFAOYSA-N 0.000 claims 1
- QUSRJRFKZHTCIL-UHFFFAOYSA-N 2-piperidin-4-yl-1h-indole Chemical compound C1CNCCC1C1=CC2=CC=CC=C2N1 QUSRJRFKZHTCIL-UHFFFAOYSA-N 0.000 claims 1
- 206010041235 Snoring Diseases 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- 208000016253 exhaustion Diseases 0.000 claims 1
- 210000003041 ligament Anatomy 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 10
- 230000002401 inhibitory effect Effects 0.000 abstract description 7
- 208000001076 sarcopenia Diseases 0.000 abstract description 2
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 339
- 239000002904 solvent Substances 0.000 description 336
- 239000012442 inert solvent Substances 0.000 description 132
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 127
- 239000002585 base Substances 0.000 description 98
- 230000035484 reaction time Effects 0.000 description 74
- 239000000203 mixture Substances 0.000 description 72
- 235000002639 sodium chloride Nutrition 0.000 description 71
- 229910052751 metal Inorganic materials 0.000 description 61
- 239000002184 metal Substances 0.000 description 61
- 239000003849 aromatic solvent Substances 0.000 description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 42
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 42
- 238000002360 preparation method Methods 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 37
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 35
- 238000010511 deprotection reaction Methods 0.000 description 35
- 150000002825 nitriles Chemical class 0.000 description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
- 150000008282 halocarbons Chemical class 0.000 description 31
- 125000006239 protecting group Chemical group 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 31
- 125000003396 thiol group Chemical group [H]S* 0.000 description 31
- 239000003054 catalyst Substances 0.000 description 29
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 29
- 238000006722 reduction reaction Methods 0.000 description 27
- 239000008103 glucose Substances 0.000 description 26
- 125000001183 hydrocarbyl group Chemical group 0.000 description 26
- 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 25
- 239000002253 acid Substances 0.000 description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 24
- 125000001153 fluoro group Chemical group F* 0.000 description 24
- 150000007524 organic acids Chemical class 0.000 description 24
- 150000001412 amines Chemical class 0.000 description 23
- 239000003153 chemical reaction reagent Substances 0.000 description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 23
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 22
- 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 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 21
- 239000011903 deuterated solvents Substances 0.000 description 21
- 229940079593 drug Drugs 0.000 description 21
- 229910052731 fluorine Inorganic materials 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000003513 alkali Substances 0.000 description 20
- 150000004982 aromatic amines Chemical class 0.000 description 20
- 239000003112 inhibitor Substances 0.000 description 20
- 125000000842 isoxazolyl group Chemical group 0.000 description 20
- 239000003638 chemical reducing agent Substances 0.000 description 18
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 18
- 239000004215 Carbon black (E152) Substances 0.000 description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 16
- 239000007800 oxidant agent Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 235000011054 acetic acid Nutrition 0.000 description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 15
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- 150000007529 inorganic bases Chemical class 0.000 description 15
- 229910052987 metal hydride Inorganic materials 0.000 description 15
- 150000004681 metal hydrides Chemical class 0.000 description 15
- 125000002524 organometallic group Chemical group 0.000 description 15
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 13
- 238000005804 alkylation reaction Methods 0.000 description 13
- 210000004369 blood Anatomy 0.000 description 13
- 239000008280 blood Substances 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 13
- 125000000335 thiazolyl group Chemical group 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012190 activator Substances 0.000 description 12
- 150000001540 azides Chemical class 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 125000003226 pyrazolyl group Chemical group 0.000 description 12
- 150000003512 tertiary amines Chemical class 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 11
- 206010036790 Productive cough Diseases 0.000 description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 11
- 239000010949 copper Substances 0.000 description 11
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
- 238000001990 intravenous administration Methods 0.000 description 11
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 11
- 150000002923 oximes Chemical class 0.000 description 11
- 208000024794 sputum Diseases 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 125000001113 thiadiazolyl group Chemical group 0.000 description 11
- 229920002678 cellulose Polymers 0.000 description 10
- 239000001913 cellulose Substances 0.000 description 10
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 238000007363 ring formation reaction Methods 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 159000000011 group IA salts Chemical class 0.000 description 9
- 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 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 description 8
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- 239000007868 Raney catalyst Substances 0.000 description 6
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
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- 125000001309 chloro group Chemical group Cl* 0.000 description 6
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
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- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
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- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
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- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
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- 201000000334 ureter transitional cell carcinoma Diseases 0.000 description 1
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- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
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- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
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Classifications
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- 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
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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| TWI719974B (zh) * | 2015-03-30 | 2021-03-01 | 日商塩野義製藥股份有限公司 | 9員縮合環衍生物 |
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| EA201390794A1 (ru) | 2010-11-30 | 2013-11-29 | Такеда Фармасьютикал Компани Лимитед | Бициклическое соединение |
| EP2772485A4 (en) * | 2011-10-24 | 2015-06-10 | Takeda Pharmaceutical | BICYCLIC CONNECTION |
| US8530460B2 (en) * | 2011-12-19 | 2013-09-10 | Boehringer Ingelheim International Gmbh | Azetidine derivatives |
| US8530461B2 (en) | 2011-12-29 | 2013-09-10 | Boehringer Ingelheim International Gmbh | Azetidine derivatives |
| US8623860B2 (en) * | 2011-12-30 | 2014-01-07 | Boehringer Ingelheim International Gmbh | Azetidine derivatives, pharmaceutical compositions and uses thereof |
| BR112016004118A2 (pt) | 2013-09-12 | 2017-10-17 | Pfizer | uso de inibidores da acetil-coa carboxilase para tratamento de acne vulgar |
| JP6050291B2 (ja) * | 2014-08-07 | 2016-12-21 | 長谷川香料株式会社 | ソラノンの製造方法およびその合成中間体 |
| CN106636402B (zh) * | 2016-12-22 | 2020-09-15 | 中南大学湘雅医院 | 一种判断鼻咽癌放疗敏感性的分子标志物及应用 |
| JP7361584B2 (ja) * | 2018-12-19 | 2023-10-16 | 高砂香料工業株式会社 | アミドの還元によるアミンの製造方法 |
| WO2023090411A1 (ja) | 2021-11-19 | 2023-05-25 | 塩野義製薬株式会社 | 心疾患または骨格筋の疾患の治療用医薬 |
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-
2011
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- 2011-04-26 KR KR1020127030925A patent/KR20130094211A/ko not_active Withdrawn
- 2011-04-26 AR ARP110101434A patent/AR080969A1/es unknown
- 2011-04-26 EA EA201291115A patent/EA021698B1/ru not_active IP Right Cessation
- 2011-04-26 EP EP11722184.6A patent/EP2563765B1/en active Active
- 2011-04-26 NZ NZ603777A patent/NZ603777A/xx not_active IP Right Cessation
- 2011-04-26 ES ES11722184.6T patent/ES2546130T3/es active Active
- 2011-04-26 GE GEAP201112904A patent/GEP20146178B/en unknown
- 2011-04-26 US US13/094,015 patent/US8703758B2/en not_active Expired - Fee Related
- 2011-04-26 JP JP2012547392A patent/JP5693611B2/ja not_active Expired - Fee Related
- 2011-04-26 BR BR112012027648A patent/BR112012027648A2/pt not_active IP Right Cessation
- 2011-04-26 CA CA2797767A patent/CA2797767A1/en not_active Abandoned
- 2011-04-26 UY UY0001033354A patent/UY33354A/es not_active Application Discontinuation
- 2011-04-26 PH PH1/2012/502347A patent/PH12012502347A1/en unknown
- 2011-04-26 CN CN201180031899.8A patent/CN103025716B/zh not_active Expired - Fee Related
- 2011-04-26 TW TW100114410A patent/TW201206911A/zh unknown
- 2011-04-26 WO PCT/JP2011/060616 patent/WO2011136385A1/en not_active Ceased
- 2011-04-26 SG SG2012086880A patent/SG185759A1/en unknown
- 2011-04-26 UA UAA201213528A patent/UA108102C2/ru unknown
- 2011-04-26 AU AU2011246004A patent/AU2011246004A1/en not_active Abandoned
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2012
- 2012-11-26 CR CR20120598A patent/CR20120598A/es not_active Application Discontinuation
- 2012-11-26 ZA ZA2012/08895A patent/ZA201208895B/en unknown
- 2012-11-27 EC ECSP12012311 patent/ECSP12012311A/es unknown
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI719974B (zh) * | 2015-03-30 | 2021-03-01 | 日商塩野義製藥股份有限公司 | 9員縮合環衍生物 |
Also Published As
| Publication number | Publication date |
|---|---|
| MA34245B1 (fr) | 2013-05-02 |
| NZ603777A (en) | 2013-08-30 |
| CA2797767A1 (en) | 2011-11-03 |
| KR20130094211A (ko) | 2013-08-23 |
| CR20120598A (es) | 2013-02-19 |
| ES2546130T3 (es) | 2015-09-18 |
| CN103025716A (zh) | 2013-04-03 |
| BR112012027648A2 (pt) | 2019-09-24 |
| AR080969A1 (es) | 2012-05-23 |
| US8703758B2 (en) | 2014-04-22 |
| CO6640253A2 (es) | 2013-03-22 |
| CN103025716B (zh) | 2014-12-24 |
| UA108102C2 (uk) | 2015-03-25 |
| AU2011246004A1 (en) | 2012-11-29 |
| SG185759A1 (en) | 2012-12-28 |
| GEP20146178B (en) | 2014-10-10 |
| ECSP12012311A (es) | 2013-05-31 |
| JP2013525262A (ja) | 2013-06-20 |
| EP2563765B1 (en) | 2015-05-27 |
| EA201291115A1 (ru) | 2013-04-30 |
| EA021698B1 (ru) | 2015-08-31 |
| US20110263562A1 (en) | 2011-10-27 |
| UY33354A (es) | 2011-12-01 |
| PH12012502347A1 (en) | 2014-10-14 |
| WO2011136385A1 (en) | 2011-11-03 |
| JP5693611B2 (ja) | 2015-04-01 |
| EP2563765A1 (en) | 2013-03-06 |
| ZA201208895B (en) | 2014-01-29 |
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