JP5260507B2 - インドール化合物 - Google Patents
インドール化合物 Download PDFInfo
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- JP5260507B2 JP5260507B2 JP2009515658A JP2009515658A JP5260507B2 JP 5260507 B2 JP5260507 B2 JP 5260507B2 JP 2009515658 A JP2009515658 A JP 2009515658A JP 2009515658 A JP2009515658 A JP 2009515658A JP 5260507 B2 JP5260507 B2 JP 5260507B2
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- 150000002475 indoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 419
- -1 2-thienylsulfonyl Chemical group 0.000 claims description 385
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 195
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 122
- 125000005843 halogen group Chemical group 0.000 claims description 119
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 106
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 86
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 80
- 150000003839 salts Chemical class 0.000 claims description 61
- 239000003814 drug Substances 0.000 claims description 54
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 53
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 36
- 206010012601 diabetes mellitus Diseases 0.000 claims description 33
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 30
- 125000002950 monocyclic group Chemical group 0.000 claims description 30
- 229940124597 therapeutic agent Drugs 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
- 150000001408 amides Chemical class 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 208000008589 Obesity Diseases 0.000 claims description 13
- 235000020824 obesity Nutrition 0.000 claims description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- 230000000069 prophylactic effect Effects 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 229940124828 glucokinase activator Drugs 0.000 claims description 7
- CBOSBNKSXLFSCD-UHFFFAOYSA-N 2-[2-[7-[methyl(pyridin-2-ylsulfonyl)amino]-1h-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl]acetamide Chemical compound C=1C=CC=NC=1S(=O)(=O)N(C)C(C=1N2)=CC=CC=1C=C2C1=NCC(CC(N)=O)S1 CBOSBNKSXLFSCD-UHFFFAOYSA-N 0.000 claims description 4
- OAXSUSZGLQWOOI-UHFFFAOYSA-N 2-[2-[7-[methyl(thiophen-2-ylsulfonyl)amino]-1h-indol-2-yl]-1-thia-3,8-diazaspiro[4.5]dec-2-en-8-yl]acetamide Chemical compound C=1C=CSC=1S(=O)(=O)N(C)C(C=1N2)=CC=CC=1C=C2C(S1)=NCC21CCN(CC(N)=O)CC2 OAXSUSZGLQWOOI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 4
- BEYYLQOWGYFPAA-UHFFFAOYSA-N n-[2-[4-(hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(2-methoxyethoxy)-1h-indol-7-yl]-n-methylpyridine-2-sulfonamide Chemical compound C=12NC(C=3SCC(CO)N=3)=CC2=CC(OCCOC)=CC=1N(C)S(=O)(=O)C1=CC=CC=N1 BEYYLQOWGYFPAA-UHFFFAOYSA-N 0.000 claims description 4
- LKZWRIUWVWHYKZ-UHFFFAOYSA-N n-methyl-n-[2-(8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-2-yl)-1h-indol-7-yl]thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)N(C)C(C=1N2)=CC=CC=1C=C2C(S1)=NCC21CCOCC2 LKZWRIUWVWHYKZ-UHFFFAOYSA-N 0.000 claims description 4
- HYMJWLBAIUGXBW-UHFFFAOYSA-N n-methyl-n-[2-[5-(morpholin-4-ylmethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1h-indol-7-yl]thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)N(C)C(C=1N2)=CC=CC=1C=C2C(S1)=NCC1CN1CCOCC1 HYMJWLBAIUGXBW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 177
- 125000001424 substituent group Chemical group 0.000 description 177
- 239000002904 solvent Substances 0.000 description 99
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 96
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 91
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 73
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 73
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 54
- 235000002639 sodium chloride Nutrition 0.000 description 54
- 150000002430 hydrocarbons Chemical group 0.000 description 53
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 52
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 49
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 47
- 239000002585 base Substances 0.000 description 46
- 125000003118 aryl group Chemical group 0.000 description 45
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 42
- 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 42
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 42
- 239000008103 glucose Substances 0.000 description 42
- 229930195733 hydrocarbon Natural products 0.000 description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 37
- 239000004215 Carbon black (E152) Substances 0.000 description 36
- 108010021582 Glucokinase Proteins 0.000 description 35
- 102100029237 Hexokinase-4 Human genes 0.000 description 35
- 229910052731 fluorine Inorganic materials 0.000 description 35
- 125000001153 fluoro group Chemical group F* 0.000 description 35
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 125000003277 amino group Chemical group 0.000 description 31
- 230000035484 reaction time Effects 0.000 description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 30
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 30
- 238000000034 method Methods 0.000 description 29
- 239000003638 chemical reducing agent Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 26
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 25
- 239000013078 crystal Substances 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 23
- 125000002883 imidazolyl group Chemical group 0.000 description 23
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 22
- 229940052303 ethers for general anesthesia Drugs 0.000 description 22
- 239000007788 liquid Substances 0.000 description 22
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229960004132 diethyl ether Drugs 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 125000001425 triazolyl group Chemical group 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 125000003710 aryl alkyl group Chemical group 0.000 description 20
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 20
- 125000004076 pyridyl group Chemical group 0.000 description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
- 150000002170 ethers Chemical class 0.000 description 19
- 125000002757 morpholinyl group Chemical group 0.000 description 19
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 19
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 18
- 235000011054 acetic acid Nutrition 0.000 description 17
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 17
- 229910052801 chlorine Inorganic materials 0.000 description 17
- 125000001309 chloro group Chemical group Cl* 0.000 description 17
- 229940079593 drug Drugs 0.000 description 17
- 125000004043 oxo group Chemical group O=* 0.000 description 17
- 238000006722 reduction reaction Methods 0.000 description 17
- 229930195734 saturated hydrocarbon Natural products 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 239000003377 acid catalyst Substances 0.000 description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 16
- 125000002541 furyl group Chemical group 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 15
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 15
- 125000005530 alkylenedioxy group Chemical group 0.000 description 15
- 210000004369 blood Anatomy 0.000 description 15
- 239000008280 blood Substances 0.000 description 15
- 235000019253 formic acid Nutrition 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 150000007524 organic acids Chemical class 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 14
- 125000004193 piperazinyl group Chemical group 0.000 description 14
- 125000003386 piperidinyl group Chemical group 0.000 description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 150000001298 alcohols 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
- 230000000694 effects Effects 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 12
- 235000005985 organic acids Nutrition 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 235000011181 potassium carbonates Nutrition 0.000 description 12
- 125000001544 thienyl group Chemical group 0.000 description 12
- 206010056997 Impaired fasting glucose Diseases 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 229940002612 prodrug Drugs 0.000 description 11
- 239000000651 prodrug Substances 0.000 description 11
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 11
- 206010006895 Cachexia Diseases 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 10
- 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 10
- 230000003914 insulin secretion Effects 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 125000000335 thiazolyl group Chemical group 0.000 description 10
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 9
- 208000002705 Glucose Intolerance Diseases 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 150000001924 cycloalkanes Chemical class 0.000 description 9
- 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 9
- 210000004185 liver Anatomy 0.000 description 9
- 229940098779 methanesulfonic acid Drugs 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 9
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 9
- 125000003831 tetrazolyl group Chemical group 0.000 description 9
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 9
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 8
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
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- 125000004300 thiazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])SC1([H])* 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/14—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 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
-
- 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
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| JP2009515658A JP5260507B2 (ja) | 2006-10-19 | 2007-10-18 | インドール化合物 |
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| JP2009515658A JP5260507B2 (ja) | 2006-10-19 | 2007-10-18 | インドール化合物 |
| PCT/JP2007/070772 WO2008050821A1 (en) | 2006-10-19 | 2007-10-18 | Indole compound |
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| JP2010506825A JP2010506825A (ja) | 2010-03-04 |
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| US8445679B2 (en) * | 2007-04-16 | 2013-05-21 | Abbvie Inc. | 7-substituted indole MCL-1 inhibitors |
| WO2008136428A1 (ja) | 2007-04-27 | 2008-11-13 | Takeda Pharmaceutical Company Limited | 含窒素５員複素環化合物 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2009025477A1 (en) | 2007-08-17 | 2009-02-26 | Lg Life Sciences Ltd. | Indole compounds as an inhibitor of cellular necrosis |
| US20100267708A1 (en) * | 2007-12-20 | 2010-10-21 | Lg Life Sciences Ltd. | Glucokinase activators and pharmaceutical compositions containing the same as an active ingredient |
| US20100291533A1 (en) * | 2008-01-04 | 2010-11-18 | Soon Ha Kim | Indole and indazole derivatives having a cell-, tissue- and organ-preserving effect |
| EP2242745A1 (de) * | 2008-02-07 | 2010-10-27 | Sanofi-Aventis | Neue phenyl-substituierte imidazolidine, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| DK2276760T3 (da) | 2008-04-10 | 2014-05-26 | Takeda Pharmaceutical | Kondenserede ringforbindelser og anvendelse deraf |
| US8349886B2 (en) * | 2008-04-16 | 2013-01-08 | Takeda Pharmaceutical Company Limited | Nitrogenated 5-membered heterocyclic compound |
| AR072297A1 (es) | 2008-06-27 | 2010-08-18 | Novartis Ag | Derivados de indol-2-il-piridin-3-ilo, composicion farmaceutica que los comprende y su uso en medicamentos para el tratamiento de enfermedades mediadas por la sintasa aldosterona. |
| JP5597200B2 (ja) * | 2008-08-18 | 2014-10-01 | プロメガ コーポレイション | ルミネッセンスを生じる化合物およびチトクロムｐ４５０３ａ酵素を検出するための方法 |
| AR073380A1 (es) | 2008-09-25 | 2010-11-03 | Takeda Pharmaceutical | Composicion farmaceutica solida. comprimido multicapa |
| EP2351743A4 (en) | 2008-10-27 | 2012-05-09 | Takeda Pharmaceutical | BICYCLIC COMPOUND |
| EP2371826A4 (en) | 2008-12-29 | 2012-06-27 | Takeda Pharmaceutical | NEW CONNECTION WITH CONDENSED RINGS AND ITS USE |
| WO2010117085A1 (en) * | 2009-04-09 | 2010-10-14 | Banyu Pharmaceutical Co.,Ltd. | Aryl indole derivatives |
| EP2440541A1 (en) | 2009-06-09 | 2012-04-18 | Takeda Pharmaceutical Company Limited | Novel fused cyclic compound and use thereof |
| MX2012001284A (es) | 2009-07-28 | 2012-03-26 | Takeda Pharmaceutical | Tableta. |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| MA34245B1 (fr) | 2010-04-27 | 2013-05-02 | Takeda Pharmaceutcal Company Ltd | Dérivés de composés bicycliques et leur utilisation en tant qu'inhibiteurs de l'acc. |
| EA022094B1 (ru) | 2010-06-16 | 2015-10-30 | Такеда Фармасьютикал Компани Лимитед | Кристаллическая форма амидного соединения |
| WO2011159781A2 (en) * | 2010-06-17 | 2011-12-22 | Senomyx, Inc. | Bitter taste modulators |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| 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 |
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| EP2617726A4 (en) | 2010-09-17 | 2014-05-14 | Takeda Pharmaceutical | DIABETES THERAPEUTIC |
| EA201390794A1 (ru) | 2010-11-30 | 2013-11-29 | Такеда Фармасьютикал Компани Лимитед | Бициклическое соединение |
| BR112013020634A2 (pt) | 2011-02-17 | 2016-10-25 | Takeda Pharmaceutical | método para produzir uma forma opticamente ativa de um composto, sal, complexo de rutênio, composto, e, cristal |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013057944A1 (ja) * | 2011-10-19 | 2013-04-25 | 興和株式会社 | 新規なスピロインドリン化合物、及びそれを含有する医薬 |
| EP2772485A4 (en) | 2011-10-24 | 2015-06-10 | Takeda Pharmaceutical | BICYCLIC CONNECTION |
| EP2802571A1 (en) | 2012-01-12 | 2014-11-19 | Takeda Pharmaceutical Company Limited | Benzimidazole derivatives as mch receptor antagonists |
| EP2816032A4 (en) | 2012-02-13 | 2015-09-30 | Takeda Pharmaceutical | AROMATIC RING CONNECTION |
| US9382188B2 (en) | 2012-02-13 | 2016-07-05 | Takeda Pharmaceutical Company Limited | Aromatic ring compound |
| US20150011549A1 (en) | 2012-02-15 | 2015-01-08 | Takeda Pharmaceutical Company Limited | Tablet |
| CN104254525B (zh) | 2012-02-24 | 2016-05-25 | 武田药品工业株式会社 | 芳环化合物 |
| CN104350040B (zh) | 2012-03-29 | 2016-06-01 | 武田药品工业株式会社 | 芳环化合物 |
| EP2836482B1 (en) | 2012-04-10 | 2019-12-25 | The Regents of The University of California | Compositions and methods for treating cancer |
| US9440987B2 (en) | 2012-05-10 | 2016-09-13 | Takeda Pharmaceutical Company Limited | Aromatic ring compound |
| US9505772B2 (en) | 2012-05-10 | 2016-11-29 | Takeda Pharmaceutical Company Limited | Aromatic ring compound |
| CN104519874B (zh) | 2012-06-05 | 2018-08-03 | 武田药品工业株式会社 | 固体制剂 |
| JP2015127299A (ja) | 2012-07-19 | 2015-07-09 | 武田薬品工業株式会社 | 固形製剤 |
| WO2014085486A2 (en) | 2012-11-30 | 2014-06-05 | Waters Technologies Corporation | Methods and apparatus for the analysis of vitamin d metabolites |
| US9605000B2 (en) | 2013-03-14 | 2017-03-28 | Takeda Pharmaceutical Company Limited | Spiro azetidine isoxazole derivatives and their use as SSTR antagonists |
| US10005720B2 (en) | 2013-04-05 | 2018-06-26 | North Carolina Central University | Compounds useful for the treatment of metabolic disorders and synthesis of the same |
| TW201536767A (zh) | 2013-07-09 | 2015-10-01 | Takeda Pharmaceutical | 雜環化合物 |
| HRP20181011T1 (hr) | 2013-08-09 | 2018-08-24 | Takeda Pharmaceutical Company Limited | Aromatski spoj |
| WO2015026172A1 (ko) * | 2013-08-22 | 2015-02-26 | 주식회사 엘지생명과학 | 세포괴사 저해제로서의 인돌아미드 화합물 |
| JO3442B1 (ar) | 2013-10-07 | 2019-10-20 | Takeda Pharmaceuticals Co | مضادات ذات نوع فرعي من مستقبل سوماتوستاتين 5 (sstr5) |
| US9428470B2 (en) | 2014-02-13 | 2016-08-30 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| US9346776B2 (en) | 2014-02-13 | 2016-05-24 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound |
| CN104098498A (zh) * | 2014-07-30 | 2014-10-15 | 天津市斯芬克司药物研发有限公司 | 一种吲唑类化合物及其制备方法 |
| JOP20180029A1 (ar) | 2017-03-30 | 2019-01-30 | Takeda Pharmaceuticals Co | مركب حلقي غير متجانس |
| AR111199A1 (es) | 2017-03-31 | 2019-06-12 | Takeda Pharmaceuticals Co | Compuesto aromático agonista de gpr40 |
| CN110719903A (zh) | 2017-03-31 | 2020-01-21 | 武田药品工业株式会社 | 芳族环化合物 |
| JOP20180028A1 (ar) | 2017-03-31 | 2019-01-30 | Takeda Pharmaceuticals Co | مركب ببتيد |
| EA202092269A1 (ru) | 2018-03-23 | 2020-12-14 | Кармот Терапьютикс, Инк. | Модуляторы сопряженных с g-белком рецепторов |
| TW202024028A (zh) | 2018-08-27 | 2020-07-01 | 日商思可海雅藥品股份有限公司 | 苯甲酸酯化合物 |
| JP7511548B2 (ja) | 2018-09-24 | 2024-07-05 | 武田薬品工業株式会社 | Ｇｉｐ受容体アゴニストペプチド化合物及びその使用 |
| US12122815B2 (en) | 2018-09-24 | 2024-10-22 | Takeda Pharmaceutical Company Limited | GIP receptor agonist peptide compounds and uses thereof |
| CN109250963B (zh) * | 2018-09-29 | 2021-07-16 | 福建省昊立建设工程有限公司 | 一种复合增韧混凝土及其制备方法 |
| PH12022552056A1 (en) | 2020-02-07 | 2024-02-12 | Gasherbrum Bio Inc | Heterocyclic glp-1 agonists |
| PE20221727A1 (es) | 2020-03-25 | 2022-11-04 | Takeda Pharmaceuticals Co | Dosificacion qw de compuestos peptidicos agonistas del receptor de gip y sus usos |
| BR112022019114A2 (pt) | 2020-03-25 | 2023-02-14 | Takeda Pharmaceuticals Co | Dosagem qd de compostos peptídicos agonistas do receptor de gip e usos dos mesmos |
| CN113563306B (zh) * | 2020-04-28 | 2022-07-01 | 新发药业有限公司 | 一种2-(4-苯氧基苯基)-6-(哌啶-4-)基烟酰胺的制备方法 |
| PE20240890A1 (es) | 2021-05-13 | 2024-04-24 | Carmot Therapeutics Inc | Moduladores de los receptores acoplados a proteinas g |
| CN119137124A (zh) | 2022-03-09 | 2024-12-13 | 加舒布鲁姆生物公司 | 杂环glp-1激动剂 |
| JP2025510741A (ja) | 2022-03-21 | 2025-04-15 | ガシャーブラム・バイオ・インコーポレイテッド | ヘテロ環式ｇｌｐ－１アゴニスト |
| CN119255988A (zh) | 2022-04-14 | 2025-01-03 | 加舒布鲁姆生物公司 | 杂环glp-1激动剂 |
| WO2024125602A1 (en) | 2022-12-15 | 2024-06-20 | Gasherbrum Bio, Inc. | Salts and solid forms of a compound having glp-1 agonist activity |
| WO2024131869A1 (en) | 2022-12-22 | 2024-06-27 | Gasherbrum Bio, Inc. | Heterocyclic glp-1 agonists |
| EP4638455A1 (en) | 2022-12-22 | 2025-10-29 | Gasherbrum Bio, Inc. | Heterocyclic glp-1 agonists |
| CN120957993A (zh) | 2023-02-16 | 2025-11-14 | 加舒布鲁姆生物公司 | 杂环glp-1激动剂 |
| WO2025006921A1 (en) | 2023-06-30 | 2025-01-02 | Gasherbrum Bio, Inc. | Heterocyclic glp-1 agonists |
| WO2025015268A1 (en) | 2023-07-13 | 2025-01-16 | Aconcagua Bio, Inc. | Modulators of calcitonin receptor and/or amylin receptor activity |
| TW202519220A (zh) | 2023-07-13 | 2025-05-16 | 美商雅空嘉閣生物公司 | 化合物、組合物及方法 |
| WO2025045208A1 (en) | 2023-08-31 | 2025-03-06 | Gasherbrum Bio, Inc. | Heteroaryl-heterocycloalkyl-based glp-1 agonists |
| US20250188081A1 (en) * | 2023-12-08 | 2025-06-12 | Shaman Pharma, LLC | Method for Production of Spiro-Oxindole and Indoxyl Derivatives of Mitragynine |
| WO2025137307A1 (en) | 2023-12-20 | 2025-06-26 | Gasherbrum Bio, Inc. | Heterocyclic glp-1 agonists |
| WO2025154021A1 (en) | 2024-01-19 | 2025-07-24 | Takeda Pharmaceutical Company Limited | Improved gip receptor agonist peptide compounds and uses thereof |
| WO2025154020A1 (en) | 2024-01-19 | 2025-07-24 | Takeda Pharmaceutical Company Limited | Improved gip receptor agonist peptide compounds and uses thereof |
| WO2025171340A1 (en) | 2024-02-08 | 2025-08-14 | Aconcagua Bio, Inc. | The treatment of calcitonin- and/or amylin-receptor associated conditions |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2656610B1 (fr) * | 1989-12-29 | 1992-05-07 | Sanofi Sa | Derives d'amino-2 phenyl-4 thiazole, leur procede de preparation et leur application therapeutique. |
| KR0174752B1 (ko) * | 1993-09-10 | 1999-02-01 | 나이토 하루오 | 이환식 헤테로환 함유 술폰아미드 유도체 및 그 제조방법 |
| JP3545461B2 (ja) * | 1993-09-10 | 2004-07-21 | エーザイ株式会社 | 二環式ヘテロ環含有スルホンアミド誘導体 |
| CN1072649C (zh) | 1995-09-13 | 2001-10-10 | 武田药品工业株式会社 | 苯并氧杂吖庚因化合物,其生产方法和用途 |
| CA2322162A1 (en) * | 1998-02-25 | 1999-09-02 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| JP4007743B2 (ja) | 1999-02-26 | 2007-11-14 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 血管新生阻害剤 |
| AR035016A1 (es) | 1999-08-25 | 2004-04-14 | Takeda Chemical Industries Ltd | Composicion de azol promotor de produccion/secrecion de neurotrofina, compuesto prodroga del mismo, composicion farmaceutica que lo comprende y uso del mismo para preparar esta ultima. |
| GB0003636D0 (en) * | 2000-02-16 | 2000-04-05 | Smithkline Beecham Plc | Novel compounds |
| US6930185B2 (en) | 2000-04-28 | 2005-08-16 | Takeda Chemical Industries, Ltd. | Melanin-concentrating hormone antagonist |
| US7229986B2 (en) | 2000-05-16 | 2007-06-12 | Takeda Pharmaceutical Company Ltd. | Melanin-concentrating hormone antagonist |
| MXPA05003391A (es) | 2002-10-03 | 2005-06-22 | Hoffmann La Roche | Indol-3-carboxamidas como activadores de glucocinasa. |
| EP1532980A1 (en) * | 2003-11-24 | 2005-05-25 | Novo Nordisk A/S | N-heteroaryl indole carboxamides and analogues thereof, for use as glucokinase activators in the treatment of diabetes |
| US7498445B2 (en) * | 2004-05-05 | 2009-03-03 | Renopharm Ltd. | Thiazole-based nitric oxide donors capable of releasing two or more nitric oxide molecules and uses thereof |
| EP1632491A1 (en) * | 2004-08-30 | 2006-03-08 | Laboratorios Del Dr. Esteve, S.A. | Substituted indole compounds and their use as 5-HT6 receptor modulators |
| CA2605778A1 (en) | 2005-04-20 | 2006-10-26 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound |
| WO2007037543A1 (ja) | 2005-09-29 | 2007-04-05 | Banyu Pharmaceutical Co., Ltd. | ビアリールアミド誘導体 |
| WO2007037534A1 (ja) | 2005-09-30 | 2007-04-05 | Banyu Pharmaceutical Co., Ltd. | ２－へテロアリール置換インドール誘導体 |
| DK2188291T3 (da) * | 2007-08-14 | 2013-01-07 | Bayer Ip Gmbh | Fusionerede bicykliske pyrimidiner |
| PA8793301A1 (es) * | 2007-08-14 | 2009-04-23 | Bayer Schering Pharma Ag | Imidazoles bicíclicos fusionados |
| JO2784B1 (en) * | 2007-10-18 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | 5,3,1 - Triazole substitute derivative |
| ES2424023T3 (es) * | 2007-10-18 | 2013-09-26 | Janssen Pharmaceutica N.V. | 1,2,4-triazoles trisustituidos |
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