JP2013513605A5 - - Google Patents
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- JP2013513605A5 JP2013513605A5 JP2012543091A JP2012543091A JP2013513605A5 JP 2013513605 A5 JP2013513605 A5 JP 2013513605A5 JP 2012543091 A JP2012543091 A JP 2012543091A JP 2012543091 A JP2012543091 A JP 2012543091A JP 2013513605 A5 JP2013513605 A5 JP 2013513605A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- chloro
- fluorophenyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000217 alkyl group Chemical group 0.000 claims description 395
- 229910052757 nitrogen Inorganic materials 0.000 claims description 232
- 125000005843 halogen group Chemical group 0.000 claims description 125
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 109
- -1 substituted Chemical class 0.000 claims description 109
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 108
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 87
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 73
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- 150000003839 salts Chemical class 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 102220470259 Charged multivesicular body protein 5_D11N_mutation Human genes 0.000 claims description 32
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 102220065736 rs543286136 Human genes 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 208000008589 Obesity Diseases 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 235000020824 obesity Nutrition 0.000 claims description 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 6
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 6
- 229940127003 anti-diabetic drug Drugs 0.000 claims description 6
- 239000003472 antidiabetic agent Substances 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 4
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 108010088406 Glucagon-Like Peptides Proteins 0.000 claims description 4
- 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 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- GSBKRFGXEJLVMI-UHFFFAOYSA-N Nervonyl carnitine Chemical compound CCC[N+](C)(C)C GSBKRFGXEJLVMI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003613 bile acid Substances 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 230000003914 insulin secretion Effects 0.000 claims description 4
- 230000004060 metabolic process Effects 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 3
- XRFBEGXBZOEFGX-UHFFFAOYSA-O 2-[[3-chloro-4-[2-[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]ethyl]-5-fluorobenzoyl]amino]ethyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(CCC=3C(=CC(=CC=3F)C(=O)NCC[N+](C)(C)C)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 XRFBEGXBZOEFGX-UHFFFAOYSA-O 0.000 claims description 2
- TVVGYHNDGBBLFV-UHFFFAOYSA-O 2-[[3-chloro-4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzoyl]amino]ethyl-trimethylazanium Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)C(=O)NCC[N+](C)(C)C)Cl)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)=C1 TVVGYHNDGBBLFV-UHFFFAOYSA-O 0.000 claims description 2
- TYMQLFZVMNUKCQ-UHFFFAOYSA-O 2-[[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methoxy]-5-fluorobenzoyl]amino]ethyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(COC=3C(=CC(=CC=3F)C(=O)NCC[N+](C)(C)C)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 TYMQLFZVMNUKCQ-UHFFFAOYSA-O 0.000 claims description 2
- UUDGEQVYCVMWKG-UHFFFAOYSA-O 2-[[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzoyl]amino]ethyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(=O)NCC[N+](C)(C)C)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 UUDGEQVYCVMWKG-UHFFFAOYSA-O 0.000 claims description 2
- HRJOIFMDODYARC-UHFFFAOYSA-O 2-[[4-[[5-[2-(3-amino-1,2-benzoxazol-5-yl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3-chloro-5-fluorobenzoyl]amino]ethyl-trimethylazanium Chemical compound C=1C=C2ON=C(N)C2=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=C(C(=O)NCC[N+](C)(C)C)C=C1Cl HRJOIFMDODYARC-UHFFFAOYSA-O 0.000 claims description 2
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- CHMBDVJEMKFZAU-UHFFFAOYSA-N 3-[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenyl]propyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(CCC[N+](C)(C)C)=CC=3F)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 CHMBDVJEMKFZAU-UHFFFAOYSA-N 0.000 claims description 2
- OEYCUWABLLKHDX-UHFFFAOYSA-N 3-[4-[[5-[2-(3-chloro-4-fluorophenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]propyl-trimethylazanium Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(CCC[N+](C)(C)C)=CC=2F)F)C(C)(C)C=2C=C(Cl)C(F)=CC=2)=C1 OEYCUWABLLKHDX-UHFFFAOYSA-N 0.000 claims description 2
- IAESLBAFXKPVCG-UHFFFAOYSA-N 3-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]prop-2-ynyl-triethylazanium Chemical compound FC1=CC(C#CC[N+](CC)(CC)CC)=CC(F)=C1CSC1=NC=C(C(C)(C)C=2C=C(OC)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 IAESLBAFXKPVCG-UHFFFAOYSA-N 0.000 claims description 2
- UELQMJSWOBJOAX-UHFFFAOYSA-N 3-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]prop-2-ynyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C#CC[N+](C)(C)C)F)=NC=2)C=2C=CC(F)=CC=2)=C1 UELQMJSWOBJOAX-UHFFFAOYSA-N 0.000 claims description 2
- CQGSLSNQUMVQDW-UHFFFAOYSA-N 3-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]propyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(CCC[N+](C)(C)C)=CC=3F)F)=NC=2)C=2C=CC(F)=CC=2)=C1 CQGSLSNQUMVQDW-UHFFFAOYSA-N 0.000 claims description 2
- VMVAHJQCFFKNIJ-UHFFFAOYSA-N 3-[[2-chloro-5-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-4-fluorophenyl]sulfonylamino]propyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(Cl)=C(C=3)S(=O)(=O)NCCC[N+](C)(C)C)F)=NC=2)C=2C=CC(F)=CC=2)=C1 VMVAHJQCFFKNIJ-UHFFFAOYSA-N 0.000 claims description 2
- QONZRUZZNNOJBR-UHFFFAOYSA-N 3-[[2-chloro-5-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenyl]sulfonylamino]propyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C=C(C(Cl)=CC=3)S(=O)(=O)NCCC[N+](C)(C)C)=NC=2)C=2C=CC(F)=CC=2)=C1 QONZRUZZNNOJBR-UHFFFAOYSA-N 0.000 claims description 2
- CYPYLDDFEHFHKX-UHFFFAOYSA-N 3-[[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenyl]sulfonylamino]propyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)NCCC[N+](C)(C)C)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 CYPYLDDFEHFHKX-UHFFFAOYSA-N 0.000 claims description 2
- XOZXGYLCCWOVHE-UHFFFAOYSA-N 3-[[4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]sulfonylamino]propyl-trimethylazanium Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)S(=O)(=O)NCCC[N+](C)(C)C)F)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)=C1 XOZXGYLCCWOVHE-UHFFFAOYSA-N 0.000 claims description 2
- PHZWVHNYVOGUIP-UHFFFAOYSA-O 3-[[4-[[5-[2-(4-chloro-3-hydroxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]sulfonylamino]propyl-trimethylazanium Chemical compound C=1C=C(Cl)C(O)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=C(S(=O)(=O)NCCC[N+](C)(C)C)C=C1F PHZWVHNYVOGUIP-UHFFFAOYSA-O 0.000 claims description 2
- UXGVODFPURWQFW-UHFFFAOYSA-N 3-[[4-chloro-5-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorophenyl]sulfonylamino]propyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(F)=C(C=3)S(=O)(=O)NCCC[N+](C)(C)C)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 UXGVODFPURWQFW-UHFFFAOYSA-N 0.000 claims description 2
- HBAFNFVIVROBBV-UHFFFAOYSA-O 3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-n-(1,1-dimethylpiperidin-1-ium-4-yl)-5-fluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(=O)NC3CC[N+](C)(C)CC3)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 HBAFNFVIVROBBV-UHFFFAOYSA-O 0.000 claims description 2
- YOACYQJRMLGRAN-UHFFFAOYSA-N 3-chloro-5-fluoro-4-[[5-[2-(4-fluoro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-n-(3-pyridin-1-ium-1-ylpropyl)benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)NCCC[N+]=3C=CC=CC=3)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 YOACYQJRMLGRAN-UHFFFAOYSA-N 0.000 claims description 2
- FLQLWFXLPSYPDP-UHFFFAOYSA-N 3-chloro-n-[(1,1-dimethylpiperidin-1-ium-4-yl)methyl]-5-fluoro-4-[[5-[2-(4-fluoro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)NCC3CC[N+](C)(C)CC3)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 FLQLWFXLPSYPDP-UHFFFAOYSA-N 0.000 claims description 2
- FYGZGBIFZZJLNU-DEOSSOPVSA-O 3-chloro-n-[(3s)-1,1-dimethylpiperidin-1-ium-3-yl]-5-fluoro-4-[[5-[2-(4-fluoro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzamide Chemical compound C1=C(F)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(=O)N[C@@H]3C[N+](C)(C)CCC3)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 FYGZGBIFZZJLNU-DEOSSOPVSA-O 0.000 claims description 2
- NWMQYBDQFWTAPE-QHCPKHFHSA-O 3-chloro-n-[(3s)-1,1-dimethylpyrrolidin-1-ium-3-yl]-5-fluoro-4-[[5-[2-(4-fluoro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzamide Chemical compound C1=C(F)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(=O)N[C@@H]3C[N+](C)(C)CC3)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 NWMQYBDQFWTAPE-QHCPKHFHSA-O 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 claims description 2
- ZCVRVXJCYQNTJL-UHFFFAOYSA-N 4-[3-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]propyl]-1-aza-4-azoniabicyclo[2.2.2]octane Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(CCC[N+]45CCN(CC4)CC5)=CC=3F)F)=NC=2)C=2C=CC(F)=CC=2)=C1 ZCVRVXJCYQNTJL-UHFFFAOYSA-N 0.000 claims description 2
- SNXDJFCTGNSJJG-UHFFFAOYSA-N 4-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]butyl-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(CCCC[N+](C)(C)C)=CC=3F)F)=NC=2)C=2C=CC(F)=CC=2)=C1 SNXDJFCTGNSJJG-UHFFFAOYSA-N 0.000 claims description 2
- YNJZULWXFBRPIW-HSZRJFAPSA-N 4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-n-[(3r)-1,1-dimethylpiperidin-1-ium-3-yl]-3,5-difluorobenzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)N[C@H]3C[N+](C)(C)CCC3)F)=NC=2)C=2C=CC(F)=CC=2)=C1 YNJZULWXFBRPIW-HSZRJFAPSA-N 0.000 claims description 2
- YNJZULWXFBRPIW-QHCPKHFHSA-N 4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-n-[(3s)-1,1-dimethylpiperidin-1-ium-3-yl]-3,5-difluorobenzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)N[C@@H]3C[N+](C)(C)CCC3)F)=NC=2)C=2C=CC(F)=CC=2)=C1 YNJZULWXFBRPIW-QHCPKHFHSA-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
- 229940123208 Biguanide Drugs 0.000 claims description 2
- 229940100389 Sulfonylurea Drugs 0.000 claims description 2
- BEORZHNQZYQVEF-RUZDIDTESA-N [(3r)-1-[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenyl]sulfonylpiperidin-3-yl]-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)N3C[C@@H](CCC3)[N+](C)(C)C)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 BEORZHNQZYQVEF-RUZDIDTESA-N 0.000 claims description 2
- QBBOXMMWTGVWQX-XMMPIXPASA-N [(3r)-1-[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenyl]sulfonylpyrrolidin-3-yl]-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)N3C[C@@H](CC3)[N+](C)(C)C)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 QBBOXMMWTGVWQX-XMMPIXPASA-N 0.000 claims description 2
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- AZULDSRGQDMWIC-UHFFFAOYSA-N [1-[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenyl]sulfonylpiperidin-4-yl]-ethyl-dimethylazanium Chemical compound C1CC([N+](C)(C)CC)CCN1S(=O)(=O)C(C=C1Cl)=CC(F)=C1CSC1=NC=C(C(C)(C)C=2C=C(OC)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 AZULDSRGQDMWIC-UHFFFAOYSA-N 0.000 claims 1
- WZOGGVZCIREOIG-UHFFFAOYSA-N [1-[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenyl]sulfonylpiperidin-4-yl]-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)N3CCC(CC3)[N+](C)(C)C)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 WZOGGVZCIREOIG-UHFFFAOYSA-N 0.000 claims 1
- KOYSWFKBKRJLBV-UHFFFAOYSA-N [1-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]sulfonylpiperidin-4-yl]-trimethylazanium Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)N3CCC(CC3)[N+](C)(C)C)F)=NC=2)C=2C=CC(F)=CC=2)=C1 KOYSWFKBKRJLBV-UHFFFAOYSA-N 0.000 claims 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 1
- 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 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 1
- 0 CC1(*)C[N+](*)(*)CCCC1 Chemical compound CC1(*)C[N+](*)(*)CCCC1 0.000 description 51
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 34
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 31
- 238000000034 method Methods 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 125000005037 alkyl phenyl group Chemical group 0.000 description 8
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 4
- IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 description 4
- 102100025353 G-protein coupled bile acid receptor 1 Human genes 0.000 description 4
- 101000857733 Homo sapiens G-protein coupled bile acid receptor 1 Proteins 0.000 description 4
- OTVAEFIXJLOWRX-UHFFFAOYSA-N 2,2-dichloro-n-[1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide Chemical group CS(=O)(=O)C1=CC=C(C(O)C(CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-UHFFFAOYSA-N 0.000 description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical group OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 3
- MUSHJGINQWRFRN-UHFFFAOYSA-N CC(C)(C)c(cc1C)ccc1OC Chemical compound CC(C)(C)c(cc1C)ccc1OC MUSHJGINQWRFRN-UHFFFAOYSA-N 0.000 description 2
- QRPPSTNABSMSCS-UHFFFAOYSA-N CC(C)(C)c1ccc(C)c(C)c1 Chemical compound CC(C)(C)c1ccc(C)c(C)c1 QRPPSTNABSMSCS-UHFFFAOYSA-N 0.000 description 2
- USNAVJUSTKDBRV-UHFFFAOYSA-N CC(C)(C)c1ccc(C)c(OC)c1 Chemical compound CC(C)(C)c1ccc(C)c(OC)c1 USNAVJUSTKDBRV-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229950004696 flusalan Drugs 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- QTPPECNJSHHJEP-UHFFFAOYSA-N [1-[3-chloro-5-fluoro-4-[[5-[2-(4-fluoro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenyl]sulfonylpiperidin-4-yl]-trimethylazanium Chemical compound C1=C(F)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)N3CCC(CC3)[N+](C)(C)C)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 QTPPECNJSHHJEP-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
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- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
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- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
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| AR (1) | AR077851A1 (enExample) |
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| TW201247627A (en) | 2011-04-28 | 2012-12-01 | Bristol Myers Squibb Co | Novel bicyclic nitrogen containing heteroaryl TGR5 receptor modulators |
| WO2013102929A1 (en) | 2011-12-26 | 2013-07-11 | Cadila Healthcare Limited | Novel compounds for treatment of diabetes, obesity or related disorders |
| WO2013164838A1 (en) * | 2012-03-07 | 2013-11-07 | Cadila Healthcare Limited | Heterocyclic compounds and their use for treatment of diabetes, obesity or related disorders |
| LT6064B (lt) | 2012-10-15 | 2014-08-25 | Vilniaus Universitetas | Fluorinti benzensulfonamidai kaip karboanhidrazės inhibitoriai |
| WO2014100025A1 (en) * | 2012-12-17 | 2014-06-26 | Exelixis, Inc. | Tgr5 agonists having an imidazole or triazole core with subtituent having a quaternary nitrogen |
| WO2014100021A1 (en) * | 2012-12-17 | 2014-06-26 | Exelixis, Inc. | Tgr5 agonists: imidazole and triazole compounds containing a quaternary nitrogen |
| CN103755652B (zh) * | 2013-12-20 | 2015-08-05 | 陕西理工学院 | 一种磺酰胺类化合物及其应用 |
| ES2869429T3 (es) * | 2014-06-12 | 2021-10-25 | Univ Lille Ii Droit & Sante | Derivados de imidazol o 1,2,4-triazol y su uso |
| CA2954978A1 (en) | 2014-07-29 | 2016-02-04 | Institut Pasteur De Lille | 2-oxo-3,4-dihydropyridine-5-carboxylates and their use |
| EA034776B1 (ru) | 2015-05-20 | 2020-03-19 | Эмджен Инк. | Триазоловые агонисты рецептора apj |
| KR102630720B1 (ko) * | 2015-08-28 | 2024-01-29 | 세키스이 메디칼 가부시키가이샤 | 벤질 화합물 |
| WO2017042380A1 (en) | 2015-09-11 | 2017-03-16 | Universite De Lille 2 Droit Et Sante | Novel 5-amino-2-thioimidazole compounds and their use |
| WO2017134188A1 (en) | 2016-02-03 | 2017-08-10 | Universite De Lille 2 Droit Et Sante | Novel dihydropyridinone and dihydropyrimidinone compounds and their use |
| WO2017192485A1 (en) | 2016-05-03 | 2017-11-09 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| PL3466934T3 (pl) | 2016-05-31 | 2024-06-10 | Taiho Pharmaceutical Co., Ltd. | Związki sulfonoamidowe lub ich sól jako inhibitory reduktazy rybonukleotydowej do leczenia nowotworu |
| WO2018005794A2 (en) * | 2016-07-01 | 2018-01-04 | Venenum Biodesign Llc | Novel non-systemic tgr5 agonists |
| WO2018097945A1 (en) | 2016-11-16 | 2018-05-31 | Amgen Inc. | Heteroaryl-substituted triazoles as apj receptor agonists |
| MA46827A (fr) | 2016-11-16 | 2019-09-25 | Amgen Inc | Composés de triazole à substitution cycloalkyle en tant qu'agonistes du récepteur apj |
| US10906890B2 (en) | 2016-11-16 | 2021-02-02 | Amgen Inc. | Triazole phenyl compounds as agonists of the APJ receptor |
| US10689367B2 (en) | 2016-11-16 | 2020-06-23 | Amgen Inc. | Triazole pyridyl compounds as agonists of the APJ receptor |
| EP3541792B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
| MA46824A (fr) | 2016-11-16 | 2019-09-25 | Amgen Inc | Composés de triazole substitués par alkyle en tant qu'agonistes du récepteur apj |
| US11149040B2 (en) | 2017-11-03 | 2021-10-19 | Amgen Inc. | Fused triazole agonists of the APJ receptor |
| WO2019107386A1 (ja) | 2017-11-29 | 2019-06-06 | 大鵬薬品工業株式会社 | 抗腫瘍剤 |
| EP3788037A1 (en) | 2018-05-01 | 2021-03-10 | Amgen Inc. | Substituted pyrimidinones as agonists of the apj receptor |
| WO2021071837A1 (en) | 2019-10-07 | 2021-04-15 | Kallyope, Inc. | Gpr119 agonists |
| TW202140440A (zh) | 2020-02-28 | 2021-11-01 | 美商克力歐普股份有限公司 | Gpr40激動劑 |
| EP4153589A4 (en) | 2020-05-19 | 2024-06-12 | Kallyope, Inc. | AMPK ACTIVATORS |
| WO2021263039A1 (en) | 2020-06-26 | 2021-12-30 | Kallyope, Inc. | Ampk activators |
| EP4225435B1 (en) * | 2020-10-09 | 2024-12-11 | Bristol-Myers Squibb Company | Aminoimidazole fpr2 agonists |
| CN114736845B (zh) * | 2022-03-23 | 2024-03-05 | 浙江树人学院 | 胰岛细胞团葡萄糖糖刺激胰岛素分泌试验高糖低糖溶液配制试剂盒 |
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| US4107288A (en) | 1974-09-18 | 1978-08-15 | Pharmaceutical Society Of Victoria | Injectable compositions, nanoparticles useful therein, and process of manufacturing same |
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| AR040241A1 (es) * | 2002-06-10 | 2005-03-23 | Merck & Co Inc | Inhibidores de la 11-beta-hidroxiesteroide deshidrogrenasa 1 para el tratamiento de la diabetes obesidad y dislipidemia |
| WO2004089367A1 (en) | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | Pharmaceutical use of substituted 1,2,4-triazoles |
| JP2007509959A (ja) * | 2003-10-28 | 2007-04-19 | アムゲン インコーポレイティッド | トリアゾール化合物およびそれに関連する使用法 |
| WO2005087750A1 (en) | 2004-03-08 | 2005-09-22 | Wyeth | Ion channel modulators |
| WO2010062861A2 (en) * | 2008-11-26 | 2010-06-03 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of obesity and diabetes |
| US8785488B2 (en) * | 2009-02-12 | 2014-07-22 | Exelixis Patent Company Llc | Triazole and imidazole derivatives for use as TGR5 agonists in the treatment of diabetes and obesity |
-
2010
- 2010-08-11 WO PCT/US2010/045195 patent/WO2011071565A1/en not_active Ceased
- 2010-08-11 TW TW099126800A patent/TW201120027A/zh unknown
- 2010-08-11 JP JP2012543091A patent/JP2013513605A/ja active Pending
- 2010-08-11 AR ARP100102942A patent/AR077851A1/es unknown
- 2010-08-11 EP EP10747545A patent/EP2509960A1/en not_active Withdrawn
- 2010-08-11 US US13/515,132 patent/US8846739B2/en active Active
- 2010-08-11 CN CN2010800637043A patent/CN102781922A/zh active Pending
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