JP2006524248A5 - - Google Patents
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- JP2006524248A5 JP2006524248A5 JP2006510073A JP2006510073A JP2006524248A5 JP 2006524248 A5 JP2006524248 A5 JP 2006524248A5 JP 2006510073 A JP2006510073 A JP 2006510073A JP 2006510073 A JP2006510073 A JP 2006510073A JP 2006524248 A5 JP2006524248 A5 JP 2006524248A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- amino
- sulfonyl
- halogen
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 293
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 122
- 229910052736 halogen Inorganic materials 0.000 claims 67
- 150000002367 halogens Chemical class 0.000 claims 67
- 125000004438 haloalkoxy group Chemical group 0.000 claims 58
- 125000001188 haloalkyl group Chemical group 0.000 claims 58
- 125000003545 alkoxy group Chemical group 0.000 claims 55
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 28
- -1 R 21 Chemical compound 0.000 claims 24
- 125000001624 naphthyl group Chemical group 0.000 claims 24
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 15
- 125000004122 cyclic group Chemical group 0.000 claims 14
- 125000001589 carboacyl group Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000002883 imidazolyl group Chemical group 0.000 claims 11
- 125000000168 pyrrolyl group Chemical group 0.000 claims 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 8
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000002541 furyl group Chemical group 0.000 claims 8
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 8
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims 7
- 125000000335 thiazolyl group Chemical group 0.000 claims 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 5
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 125000006177 alkyl benzyl group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000001326 naphthylalkyl group Chemical group 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- JHKKHOMJBFWLEZ-MUUNZHRXSA-N (2r)-2-[4-[[4-chloro-2-(trifluoromethyl)quinolin-5-yl]methyl-[3-(trifluoromethyl)phenyl]sulfonylamino]phenoxy]-3-phenylpropanoic acid Chemical compound C([C@H](C(=O)O)OC=1C=CC(=CC=1)N(CC=1C2=C(Cl)C=C(N=C2C=CC=1)C(F)(F)F)S(=O)(=O)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 JHKKHOMJBFWLEZ-MUUNZHRXSA-N 0.000 claims 1
- GLVXKHNRMFPSHO-NDEPHWFRSA-N (2s)-2-[4-[(4-methoxycarbonylphenyl)methyl-[4-(trifluoromethoxy)phenyl]sulfonylamino]phenoxy]-3-phenylpropanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1CN(S(=O)(=O)C=1C=CC(OC(F)(F)F)=CC=1)C(C=C1)=CC=C1O[C@H](C(O)=O)CC1=CC=CC=C1 GLVXKHNRMFPSHO-NDEPHWFRSA-N 0.000 claims 1
- BCPKHMXABDQTTL-HKBQPEDESA-N (2s)-2-[4-[naphthalen-2-ylmethyl-[3-(trifluoromethyl)phenyl]sulfonylamino]phenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)OC=1C=CC(=CC=1)N(CC=1C=C2C=CC=CC2=CC=1)S(=O)(=O)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 BCPKHMXABDQTTL-HKBQPEDESA-N 0.000 claims 1
- GKRLUNNMEGNCIT-DEOSSOPVSA-N (2s)-2-[[4-(2-bromo-5-dibenzofuran-4-yl-1,3-thiazol-4-yl)phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)C1=C(SC(Br)=N1)C=1C=2OC3=CC=CC=C3C=2C=CC=1)C1=CC=CC=C1 GKRLUNNMEGNCIT-DEOSSOPVSA-N 0.000 claims 1
- LQNOVIJALGPGQL-DEOSSOPVSA-N (2s)-2-[[4-(5-bromo-2-dibenzofuran-4-yl-1,3-thiazol-4-yl)phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)C1=C(SC(=N1)C=1C=2OC3=CC=CC=C3C=2C=CC=1)Br)C1=CC=CC=C1 LQNOVIJALGPGQL-DEOSSOPVSA-N 0.000 claims 1
- ZNOVKRKFMKPLMQ-NDEPHWFRSA-N (2s)-2-[[4-[(6-bromo-4-phenylquinazolin-2-yl)-(carboxymethyl)amino]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)N(CC(O)=O)C=1N=C2C=CC(Br)=CC2=C(C=2C=CC=CC=2)N=1)C(O)=O)C1=CC=CC=C1 ZNOVKRKFMKPLMQ-NDEPHWFRSA-N 0.000 claims 1
- PCSFTJMWGDYZCX-MHZLTWQESA-N (2s)-2-[[4-[(6-bromo-4-phenylquinazolin-2-yl)amino]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(NC=2N=C3C=CC(Br)=CC3=C(C=3C=CC=CC=3)N=2)=CC=1)C(O)=O)C1=CC=CC=C1 PCSFTJMWGDYZCX-MHZLTWQESA-N 0.000 claims 1
- LPMDVNAIYXJYEB-PMERELPUSA-N (2s)-2-[[4-[2,5-bis(4-ethylphenyl)-1,3-thiazol-4-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CC)=CC=C1C1=NC(C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)=C(C=2C=CC(CC)=CC=2)S1 LPMDVNAIYXJYEB-PMERELPUSA-N 0.000 claims 1
- GLQZAIDSYMCFEE-LJAQVGFWSA-N (2s)-2-[[4-[2-[(4-chlorobenzoyl)amino]-5-(4-ethylphenyl)-1,3-thiazol-4-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CC)=CC=C1C1=C(C=2C=CC(=CC=2)S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)N=C(NC(=O)C=2C=CC(Cl)=CC=2)S1 GLQZAIDSYMCFEE-LJAQVGFWSA-N 0.000 claims 1
- CVHVGARZKZAYQQ-YTTGMZPUSA-N (2s)-2-[[4-[3-(4-chlorophenyl)-5-(4-ethylphenyl)pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CC)=CC=C1C1=CC(C=2C=CC(Cl)=CC=2)=NN1C1=CC=C(S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)C=C1 CVHVGARZKZAYQQ-YTTGMZPUSA-N 0.000 claims 1
- PIVKFJRIOIHDTC-DHUJRADRSA-N (2s)-2-[[4-[3-(4-chlorophenyl)-5-(4-pentylphenyl)pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC(C=2C=CC(Cl)=CC=2)=NN1C1=CC=C(S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)C=C1 PIVKFJRIOIHDTC-DHUJRADRSA-N 0.000 claims 1
- GBHZDBWVJGMGQV-PMERELPUSA-N (2s)-2-[[4-[3-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)N1C(=CC(=N1)C=1C=CC(Cl)=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C(O)=O)C1=CC=CC=C1 GBHZDBWVJGMGQV-PMERELPUSA-N 0.000 claims 1
- KZSOAFBUMYFOIN-BHVANESWSA-N (2s)-2-[[4-[3-(4-methoxyphenyl)-5-(4-pentylphenyl)pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC(C=2C=CC(OC)=CC=2)=NN1C1=CC=C(S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)C=C1 KZSOAFBUMYFOIN-BHVANESWSA-N 0.000 claims 1
- NODJWEUGMNBPSQ-UMSFTDKQSA-N (2s)-2-[[4-[3-(4-methoxyphenyl)-5-(4-propan-2-ylphenyl)pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)C(C=2C=CC(=CC=2)C(C)C)=C1 NODJWEUGMNBPSQ-UMSFTDKQSA-N 0.000 claims 1
- VOZAWPQEXAOGTQ-YTTGMZPUSA-N (2s)-2-[[4-[4-bromo-3-(4-chlorophenyl)-5-(4-pentylphenyl)pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=C(Br)C(C=2C=CC(Cl)=CC=2)=NN1C1=CC=C(S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)C=C1 VOZAWPQEXAOGTQ-YTTGMZPUSA-N 0.000 claims 1
- UHDSXUYQEBQGGT-MHZLTWQESA-N (2s)-2-[[4-[4-bromo-3-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)N1C(=C(Br)C(=N1)C=1C=CC(Cl)=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C(O)=O)C1=CC=CC=C1 UHDSXUYQEBQGGT-MHZLTWQESA-N 0.000 claims 1
- OGFJQHVTLKGHTG-NDEPHWFRSA-N (2s)-2-[[4-[4-bromo-3-(4-methoxyphenyl)-5-[4-(trifluoromethyl)phenyl]pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)C(C=2C=CC(=CC=2)C(F)(F)F)=C1Br OGFJQHVTLKGHTG-NDEPHWFRSA-N 0.000 claims 1
- ZVLZDZWNWRJEPT-PMERELPUSA-N (2s)-2-[[4-[5-(4-bromophenyl)-3-(4-chlorophenyl)pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)N1C(=CC(=N1)C=1C=CC(Cl)=CC=1)C=1C=CC(Br)=CC=1)C(O)=O)C1=CC=CC=C1 ZVLZDZWNWRJEPT-PMERELPUSA-N 0.000 claims 1
- XJACIPWRBQLUQI-HKBQPEDESA-N (2s)-2-[[4-[5-(4-bromophenyl)-3-(4-methoxyphenyl)pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)C(C=2C=CC(Br)=CC=2)=C1 XJACIPWRBQLUQI-HKBQPEDESA-N 0.000 claims 1
- WSOFCLJALJCKCD-DHUJRADRSA-N (2s)-2-[[4-[5-(4-butoxyphenyl)-3-(4-methoxyphenyl)pyrazol-1-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(OCCCC)=CC=C1C1=CC(C=2C=CC(OC)=CC=2)=NN1C1=CC=C(S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)C=C1 WSOFCLJALJCKCD-DHUJRADRSA-N 0.000 claims 1
- IMDNFMFXZZXLPE-NDEPHWFRSA-N (2s)-2-[[4-[5-(4-chlorophenyl)-2-(4-ethylphenyl)-1,3-thiazol-4-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CC)=CC=C1C1=NC(C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)=C(C=2C=CC(Cl)=CC=2)S1 IMDNFMFXZZXLPE-NDEPHWFRSA-N 0.000 claims 1
- VZVPGXOQYBTWHP-UHBYFKDRSA-N (2s)-2-[[4-[5-(4-methoxyphenyl)-3-(4-pentylphenyl)-3,4-dihydropyrazol-2-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1N(C=2C=CC(=CC=2)S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)N=C(C=2C=CC(OC)=CC=2)C1 VZVPGXOQYBTWHP-UHBYFKDRSA-N 0.000 claims 1
- XHUNKDZROLPGTH-NDEPHWFRSA-N (2s)-2-[[4-[[4-(3-chloro-4-methylphenyl)-5-(4-methylphenyl)-1,3-thiazol-2-yl]carbamoyl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=C(Cl)C(C)=CC=2)N=C(NC(=O)C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)S1 XHUNKDZROLPGTH-NDEPHWFRSA-N 0.000 claims 1
- QFMTUHKHFHYKON-MHZLTWQESA-N (2s)-2-[[4-[[4-(3-chlorophenyl)-5-(4-methylphenyl)-1,3-thiazol-2-yl]carbamoyl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=C(Cl)C=CC=2)N=C(NC(=O)C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)S1 QFMTUHKHFHYKON-MHZLTWQESA-N 0.000 claims 1
- XQRNKFVAIHBWNB-MHZLTWQESA-N (2s)-2-[[4-[[4-(4-bromophenyl)-5-(4-methylphenyl)-1,3-thiazol-2-yl]carbamoyl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(Br)=CC=2)N=C(NC(=O)C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)S1 XQRNKFVAIHBWNB-MHZLTWQESA-N 0.000 claims 1
- KNCKDNIJKMLDRQ-NDEPHWFRSA-N (2s)-2-[[4-[[4-(4-chlorophenyl)-5-(4-ethylphenyl)-1,3-thiazol-2-yl]carbamoyl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CC)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C(NC(=O)C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)S1 KNCKDNIJKMLDRQ-NDEPHWFRSA-N 0.000 claims 1
- SWURVAQLIFKIKR-MHZLTWQESA-N (2s)-2-[[4-[[4-(4-chlorophenyl)-5-(4-methoxyphenyl)-1,3-thiazol-2-yl]carbamoyl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C(NC(=O)C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)S1 SWURVAQLIFKIKR-MHZLTWQESA-N 0.000 claims 1
- BYJQHIMUPSGRRO-NDEPHWFRSA-N (2s)-2-[[4-[[4-(4-chlorophenyl)-5-(4-methylphenyl)-1,3-thiazol-2-yl]carbamoyl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)C(=O)NC=1SC(=C(N=1)C=1C=CC(Cl)=CC=1)C=1C=CC(C)=CC=1)C(O)=O)C1=CC=CC=C1 BYJQHIMUPSGRRO-NDEPHWFRSA-N 0.000 claims 1
- KSCXGQYYBWNVJE-MHZLTWQESA-N (2s)-2-[[4-[[4-(4-chlorophenyl)-5-(4-methylphenyl)-1,3-thiazol-2-yl]carbamoyl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C(NC(=O)C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)S1 KSCXGQYYBWNVJE-MHZLTWQESA-N 0.000 claims 1
- CADCTZHISCGOJA-PMERELPUSA-N (2s)-2-[methyl-[4-[(4-phenyl-6-propan-2-ylquinazolin-2-yl)amino]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C1=CC=C(C=C1)NC1=NC2=CC=C(C=C2C(C=2C=CC=CC=2)=N1)C(C)C)C(O)=O)C1=CC=CC=C1 CADCTZHISCGOJA-PMERELPUSA-N 0.000 claims 1
- WALBWNAHKQXMJK-HTIIIDOHSA-N (2s)-2-[methyl-[4-[3-(4-pentylphenyl)-5-[4-(trifluoromethoxy)phenyl]-3,4-dihydropyrazol-2-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1N(C=2C=CC(=CC=2)S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)N=C(C=2C=CC(OC(F)(F)F)=CC=2)C1 WALBWNAHKQXMJK-HTIIIDOHSA-N 0.000 claims 1
- RQDQPMLFGZGDCD-NDEPHWFRSA-N (2s)-2-[methyl-[4-[5-(4-pentylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)C=C1 RQDQPMLFGZGDCD-NDEPHWFRSA-N 0.000 claims 1
- WGENSCGUJNQUTJ-DHUJRADRSA-N (2s)-2-[methyl-[4-[5-(4-pentylphenyl)-3-[4-(trifluoromethoxy)phenyl]pyrazol-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC(C=2C=CC(OC(F)(F)F)=CC=2)=NN1C1=CC=C(S(=O)(=O)N(C)[C@@H](CC=2C=CC=CC=2)C(O)=O)C=C1 WGENSCGUJNQUTJ-DHUJRADRSA-N 0.000 claims 1
- KCODHGCQOIAXDB-XIFFEERXSA-N (2s)-3-phenyl-2-[3-[(4-phenylphenyl)methyl-[4-(trifluoromethoxy)phenyl]sulfonylamino]phenoxy]propanoic acid Chemical compound C([C@@H](C(=O)O)OC=1C=C(C=CC=1)N(CC=1C=CC(=CC=1)C=1C=CC=CC=1)S(=O)(=O)C=1C=CC(OC(F)(F)F)=CC=1)C1=CC=CC=C1 KCODHGCQOIAXDB-XIFFEERXSA-N 0.000 claims 1
- MXRZLRAEMBMECY-XIFFEERXSA-N (2s)-3-phenyl-2-[4-[(4-phenylphenyl)methyl-[3-(trifluoromethyl)phenyl]sulfonylamino]phenoxy]propanoic acid Chemical compound C([C@@H](C(=O)O)OC=1C=CC(=CC=1)N(CC=1C=CC(=CC=1)C=1C=CC=CC=1)S(=O)(=O)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 MXRZLRAEMBMECY-XIFFEERXSA-N 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- FGJYKLNJNRVADL-UHFFFAOYSA-N 2-[3-(4-bromoanilino)-4-[(4-butylphenyl)sulfonylamino]phenoxy]-3-phenylpropanoic acid Chemical compound C1=CC(CCCC)=CC=C1S(=O)(=O)NC(C(=C1)NC=2C=CC(Br)=CC=2)=CC=C1OC(C(O)=O)CC1=CC=CC=C1 FGJYKLNJNRVADL-UHFFFAOYSA-N 0.000 claims 1
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- OGPBWXWOXJROEK-UHFFFAOYSA-N 2-[3-(4-butylanilino)-4-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonylamino]phenoxy]-3-phenylpropanoic acid Chemical compound C1=CC(CCCC)=CC=C1NC1=CC(OC(CC=2C=CC=CC=2)C(O)=O)=CC=C1NS(=O)(=O)C1=C(C)C2=CC(Cl)=CC=C2S1 OGPBWXWOXJROEK-UHFFFAOYSA-N 0.000 claims 1
- ZPQIWHVSHNEESK-UHFFFAOYSA-N 2-[3-(4-butylanilino)-4-[[2-nitro-4-(trifluoromethyl)phenyl]sulfonylamino]phenoxy]-3-phenylpropanoic acid Chemical compound C1=CC(CCCC)=CC=C1NC1=CC(OC(CC=2C=CC=CC=2)C(O)=O)=CC=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O ZPQIWHVSHNEESK-UHFFFAOYSA-N 0.000 claims 1
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- RAUAPPNMPXUSTN-UHFFFAOYSA-N 2-[4-[(4-bromobenzoyl)amino]-3-(4-butylanilino)phenoxy]-3-phenylpropanoic acid Chemical compound C1=CC(CCCC)=CC=C1NC1=CC(OC(CC=2C=CC=CC=2)C(O)=O)=CC=C1NC(=O)C1=CC=C(Br)C=C1 RAUAPPNMPXUSTN-UHFFFAOYSA-N 0.000 claims 1
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- IOIZTKLTECDAEB-UHFFFAOYSA-N 2-[[4-[2-[(2-cyclopentylacetyl)amino]-5-(4-ethylphenyl)-1,3-thiazol-4-yl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C1=CC(CC)=CC=C1C1=C(C=2C=CC(=CC=2)S(=O)(=O)N(C)C(CC=2C=CC=CC=2)C(O)=O)N=C(NC(=O)CC2CCCC2)S1 IOIZTKLTECDAEB-UHFFFAOYSA-N 0.000 claims 1
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- QFMTUHKHFHYKON-UHFFFAOYSA-N 2-[[4-[[4-(3-chlorophenyl)-5-(4-methylphenyl)-1,3-thiazol-2-yl]carbamoyl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=C(Cl)C=CC=2)N=C(NC(=O)C=2C=CC(=CC=2)S(=O)(=O)NC(CC=2C=CC=CC=2)C(O)=O)S1 QFMTUHKHFHYKON-UHFFFAOYSA-N 0.000 claims 1
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- JBFMBGQPNREJIQ-UHFFFAOYSA-N 2-benzyl-4-[3-[(3,4-dichlorophenyl)sulfonyl-[(4-phenylphenyl)methyl]amino]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C(Cl)C(Cl)=CC=1)CC(C=C1)=CC=C1C1=CC=CC=C1 JBFMBGQPNREJIQ-UHFFFAOYSA-N 0.000 claims 1
- MDVAMKOEJJVUAY-UHFFFAOYSA-N 2-benzyl-4-[3-[(3,4-dichlorophenyl)sulfonyl-[(4-propan-2-ylphenyl)methyl]amino]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CN(S(=O)(=O)C=1C=C(Cl)C(Cl)=CC=1)C1=CC=CC(C(=O)CC(CC=2C=CC=CC=2)C(O)=O)=C1 MDVAMKOEJJVUAY-UHFFFAOYSA-N 0.000 claims 1
- XJTMJEXPAKBYGX-UHFFFAOYSA-N 2-benzyl-4-[3-[[4-chloro-3-(trifluoromethyl)phenyl]methyl-(3,4-dichlorophenyl)sulfonylamino]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C(Cl)C(Cl)=CC=1)CC1=CC=C(Cl)C(C(F)(F)F)=C1 XJTMJEXPAKBYGX-UHFFFAOYSA-N 0.000 claims 1
- BEWQJYBUCBCAEC-UHFFFAOYSA-N 2-benzyl-4-[3-[[4-chloro-3-(trifluoromethyl)phenyl]methyl-[4-(dimethylamino)-3-(trifluoromethyl)phenyl]sulfonylamino]phenyl]-4-oxobutanoic acid Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC=C1S(=O)(=O)N(C=1C=C(C=CC=1)C(=O)CC(CC=1C=CC=CC=1)C(O)=O)CC1=CC=C(Cl)C(C(F)(F)F)=C1 BEWQJYBUCBCAEC-UHFFFAOYSA-N 0.000 claims 1
- GOLWZHKBZLKQBC-UHFFFAOYSA-N 2-benzyl-4-[3-[[4-methoxy-3-(trifluoromethyl)phenyl]sulfonyl-(naphthalen-2-ylmethyl)amino]phenyl]-4-oxobutanoic acid Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1S(=O)(=O)N(C=1C=C(C=CC=1)C(=O)CC(CC=1C=CC=CC=1)C(O)=O)CC1=CC=C(C=CC=C2)C2=C1 GOLWZHKBZLKQBC-UHFFFAOYSA-N 0.000 claims 1
- JUZLAAWEYZUMLO-UHFFFAOYSA-N 2-benzyl-4-[3-[naphthalen-2-ylmethyl(naphthalen-2-ylsulfonyl)amino]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC(N(CC=2C=C3C=CC=CC3=CC=2)S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=CC=1C(=O)CC(C(=O)O)CC1=CC=CC=C1 JUZLAAWEYZUMLO-UHFFFAOYSA-N 0.000 claims 1
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- DMJQBPNURGLAKH-UHFFFAOYSA-N 2-benzyl-4-[3-[naphthalen-2-ylsulfonyl-[(4-phenylphenyl)methyl]amino]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)CC(C=C1)=CC=C1C1=CC=CC=C1 DMJQBPNURGLAKH-UHFFFAOYSA-N 0.000 claims 1
- SZVBYJHIZLSMGJ-UHFFFAOYSA-N 2-benzyl-4-[4-[(3,4-dichlorophenyl)sulfonyl-[[4-(trifluoromethoxy)phenyl]methyl]amino]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=C1)=CC=C1N(S(=O)(=O)C=1C=C(Cl)C(Cl)=CC=1)CC1=CC=C(OC(F)(F)F)C=C1 SZVBYJHIZLSMGJ-UHFFFAOYSA-N 0.000 claims 1
- OWGRBVJTVKYCOU-UHFFFAOYSA-N 2-benzyl-4-[4-[[2-nitro-4-(trifluoromethyl)phenyl]sulfonylamino]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O OWGRBVJTVKYCOU-UHFFFAOYSA-N 0.000 claims 1
- ZRJQMASSRAEXNJ-UHFFFAOYSA-N 2-benzyl-4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]methyl-(3,4-dichlorophenyl)sulfonylamino]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=C1)=CC=C1N(S(=O)(=O)C=1C=C(Cl)C(Cl)=CC=1)CC1=CC=C(Cl)C(C(F)(F)F)=C1 ZRJQMASSRAEXNJ-UHFFFAOYSA-N 0.000 claims 1
- QDNHSNOWFZAGPR-UHFFFAOYSA-N 2-benzyl-4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]methyl-(3-fluoro-4-methoxyphenyl)sulfonylamino]phenyl]-4-oxobutanoic acid Chemical compound C1=C(F)C(OC)=CC=C1S(=O)(=O)N(C=1C=CC(=CC=1)C(=O)CC(CC=1C=CC=CC=1)C(O)=O)CC1=CC=C(Cl)C(C(F)(F)F)=C1 QDNHSNOWFZAGPR-UHFFFAOYSA-N 0.000 claims 1
- YOQJZLYEHNZJCL-UHFFFAOYSA-N 2-benzyl-4-[4-[[4-methoxy-3-(trifluoromethyl)phenyl]sulfonyl-(naphthalen-1-ylmethyl)amino]phenyl]-4-oxobutanoic acid Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1S(=O)(=O)N(C=1C=CC(=CC=1)C(=O)CC(CC=1C=CC=CC=1)C(O)=O)CC1=CC=CC2=CC=CC=C12 YOQJZLYEHNZJCL-UHFFFAOYSA-N 0.000 claims 1
- JCPPTWAYIFGDOE-UHFFFAOYSA-N 2-benzyl-4-oxo-4-[3-[(4-phenylphenyl)methyl-[4-(trifluoromethoxy)phenyl]sulfonylamino]phenyl]butanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=CC(OC(F)(F)F)=CC=1)CC(C=C1)=CC=C1C1=CC=CC=C1 JCPPTWAYIFGDOE-UHFFFAOYSA-N 0.000 claims 1
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- XZFKCUPYEGVDOG-UHFFFAOYSA-N 2-benzyl-4-oxo-4-[4-[(4-phenylphenyl)methyl-[4-(trifluoromethoxy)phenyl]sulfonylamino]phenyl]butanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=C1)=CC=C1N(S(=O)(=O)C=1C=CC(OC(F)(F)F)=CC=1)CC(C=C1)=CC=C1C1=CC=CC=C1 XZFKCUPYEGVDOG-UHFFFAOYSA-N 0.000 claims 1
- IXAYUHQSVQMJBR-UHFFFAOYSA-N 2-benzyl-4-oxo-4-[4-[[4-(trifluoromethoxy)phenyl]sulfonylamino]phenyl]butanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 IXAYUHQSVQMJBR-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- XWPMVHQMDVXBDB-UHFFFAOYSA-N 4-(4-dibenzofuran-4-ylphenyl)-4-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]butanoic acid Chemical compound C=1C=C(C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1C(=O)CC(C(=O)O)CC1=CC=CC(C(F)(F)F)=C1 XWPMVHQMDVXBDB-UHFFFAOYSA-N 0.000 claims 1
- CQIVFZIDUIVKRL-UHFFFAOYSA-N 4-[3-[anthracen-2-ylsulfonyl(naphthalen-2-ylmethyl)amino]phenyl]-2-benzyl-4-oxobutanoic acid Chemical compound C=1C=CC(N(CC=2C=C3C=CC=CC3=CC=2)S(=O)(=O)C=2C=C3C=C4C=CC=CC4=CC3=CC=2)=CC=1C(=O)CC(C(=O)O)CC1=CC=CC=C1 CQIVFZIDUIVKRL-UHFFFAOYSA-N 0.000 claims 1
- QKIAFNMHJZONJQ-UHFFFAOYSA-N 4-[4-[(4-chlorophenyl)methyl-[4-(trifluoromethoxy)phenyl]sulfonylamino]phenyl]-4-oxo-2-(pyridin-3-ylmethyl)butanoic acid Chemical compound C=1C=CN=CC=1CC(C(=O)O)CC(=O)C(C=C1)=CC=C1N(S(=O)(=O)C=1C=CC(OC(F)(F)F)=CC=1)CC1=CC=C(Cl)C=C1 QKIAFNMHJZONJQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- PSAUZUMDZSIOAR-HKBQPEDESA-N benzyl (2s)-2-[4-[(5-nitrofuran-2-yl)methyl-[3-(trifluoromethyl)phenyl]sulfonylamino]phenoxy]-3-phenylpropanoate Chemical compound O1C([N+](=O)[O-])=CC=C1CN(S(=O)(=O)C=1C=C(C=CC=1)C(F)(F)F)C(C=C1)=CC=C1O[C@H](C(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 PSAUZUMDZSIOAR-HKBQPEDESA-N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- PEMIDKHZQZRGIR-UMSFTDKQSA-N methyl (2s)-3-phenyl-2-[4-[(4-phenylphenyl)methyl-[3-(trifluoromethyl)phenyl]sulfonylamino]phenoxy]propanoate Chemical compound C([C@@H](C(=O)OC)OC=1C=CC(=CC=1)N(CC=1C=CC(=CC=1)C=1C=CC=CC=1)S(=O)(=O)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 PEMIDKHZQZRGIR-UMSFTDKQSA-N 0.000 claims 1
- HPQSNQBJPHSEKF-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[(3,4-dichlorophenyl)methyl-(3,4-dichlorophenyl)sulfonylamino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C(Cl)C(Cl)=CC=1)CC1=CC=C(Cl)C(Cl)=C1 HPQSNQBJPHSEKF-UHFFFAOYSA-N 0.000 claims 1
- ZUKVSYREOLHYLF-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[(3,4-dichlorophenyl)sulfonyl-(naphthalen-2-ylmethyl)amino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(CC=1C=C2C=CC=CC2=CC=1)S(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 ZUKVSYREOLHYLF-UHFFFAOYSA-N 0.000 claims 1
- WJIRYSAERINXCW-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[(3,4-dichlorophenyl)sulfonyl-[(4-phenylphenyl)methyl]amino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C(Cl)C(Cl)=CC=1)CC(C=C1)=CC=C1C1=CC=CC=C1 WJIRYSAERINXCW-UHFFFAOYSA-N 0.000 claims 1
- CITITEOLNUMHNK-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[(3,4-difluorophenyl)sulfonyl-(naphthalen-2-ylmethyl)amino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(CC=1C=C2C=CC=CC2=CC=1)S(=O)(=O)C1=CC=C(F)C(F)=C1 CITITEOLNUMHNK-UHFFFAOYSA-N 0.000 claims 1
- ISQXXEMTFPDFQG-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[[4-(dimethylamino)-3-(trifluoromethyl)phenyl]sulfonyl-(naphthalen-2-ylmethyl)amino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(CC=1C=C2C=CC=CC2=CC=1)S(=O)(=O)C1=CC=C(N(C)C)C(C(F)(F)F)=C1 ISQXXEMTFPDFQG-UHFFFAOYSA-N 0.000 claims 1
- TZNDVYZEMAURJV-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[[4-(dimethylamino)-3-fluorophenyl]sulfonyl-(naphthalen-2-ylmethyl)amino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(CC=1C=C2C=CC=CC2=CC=1)S(=O)(=O)C1=CC=C(N(C)C)C(F)=C1 TZNDVYZEMAURJV-UHFFFAOYSA-N 0.000 claims 1
- PEJZCXALXBAFHO-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[[4-chloro-3-(trifluoromethyl)phenyl]methyl-(3,4-dichlorophenyl)sulfonylamino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C(Cl)C(Cl)=CC=1)CC1=CC=C(Cl)C(C(F)(F)F)=C1 PEJZCXALXBAFHO-UHFFFAOYSA-N 0.000 claims 1
- AJYJJYCOGBYMDF-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[[4-chloro-3-(trifluoromethyl)phenyl]methyl-(3,4-difluorophenyl)sulfonylamino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C(F)C(F)=CC=1)CC1=CC=C(Cl)C(C(F)(F)F)=C1 AJYJJYCOGBYMDF-UHFFFAOYSA-N 0.000 claims 1
- GJZRYOFRLHZQAF-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[[4-chloro-3-(trifluoromethyl)phenyl]methyl-[4-(dimethylamino)-3-(trifluoromethyl)phenyl]sulfonylamino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C(C(N(C)C)=CC=1)C(F)(F)F)CC1=CC=C(Cl)C(C(F)(F)F)=C1 GJZRYOFRLHZQAF-UHFFFAOYSA-N 0.000 claims 1
- KZJUIDUODBHOLR-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[[4-chloro-3-(trifluoromethyl)phenyl]methyl-naphthalen-2-ylsulfonylamino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)CC1=CC=C(Cl)C(C(F)(F)F)=C1 KZJUIDUODBHOLR-UHFFFAOYSA-N 0.000 claims 1
- NHYWCIUPMJNCLY-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[naphthalen-2-ylmethyl(naphthalen-2-ylsulfonyl)amino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC(N(CC=2C=C3C=CC=CC3=CC=2)S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=CC=1C(=O)CC(C(=O)OC)CC1=CC=CC=C1 NHYWCIUPMJNCLY-UHFFFAOYSA-N 0.000 claims 1
- PYGOZWJGCVMKRL-UHFFFAOYSA-N methyl 2-benzyl-4-[3-[naphthalen-2-ylsulfonyl-[(4-phenylphenyl)methyl]amino]phenyl]-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)CC(C=C1)=CC=C1C1=CC=CC=C1 PYGOZWJGCVMKRL-UHFFFAOYSA-N 0.000 claims 1
- WQKZHVLFLQRBKC-UHFFFAOYSA-N methyl 4-[3-[(4-benzoylphenyl)methyl-(3,4-dichlorophenyl)sulfonylamino]phenyl]-2-benzyl-4-oxobutanoate Chemical compound C=1C=CC=CC=1CC(C(=O)OC)CC(=O)C(C=1)=CC=CC=1N(S(=O)(=O)C=1C=C(Cl)C(Cl)=CC=1)CC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 WQKZHVLFLQRBKC-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Applications Claiming Priority (2)
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| US46310203P | 2003-04-14 | 2003-04-14 | |
| PCT/US2004/011650 WO2004092146A2 (en) | 2003-04-14 | 2004-04-14 | N- (((((1,3-thiazol-2-yl) amino) carbonyl) phenyl) sulfonyl) phenylalanine derivatives and related compounds for the treatment of diabetes |
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| GEP20094605B (en) * | 2004-06-04 | 2009-02-10 | Merck & Co Inc | Pyrazole derivatives, compositions containing such compounds and methods of use thereof |
| AU2005269792B9 (en) | 2004-07-22 | 2008-11-27 | Merck Sharp & Dohme Corp. | Substituted pyrazoles, compositions containing such compounds and methods of use |
| CA2585555A1 (en) * | 2004-10-28 | 2006-05-11 | The Institutes For Pharmaceutical Discovery, Llc | Substituted phenylalkanoic acids |
| US7709658B2 (en) | 2005-07-26 | 2010-05-04 | Merck Sharp & Dohme Corp. | Process for synthesizing a substituted pyrazole |
| DE102006013957A1 (de) * | 2006-03-27 | 2007-10-04 | Bayer Healthcare Aktiengesellschaft | Substituierte N-Benzyl-N-phenylbenzolsulfonamide |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| GB0815782D0 (en) * | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815784D0 (en) * | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815781D0 (en) * | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| US8410284B2 (en) | 2008-10-22 | 2013-04-02 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| US8329914B2 (en) | 2008-10-31 | 2012-12-11 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| JP2013520502A (ja) | 2010-02-25 | 2013-06-06 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体 |
| JP5694561B2 (ja) | 2010-12-23 | 2015-04-01 | ファイザー・インク | グルカゴン受容体モジュレーター |
| WO2012100734A1 (en) * | 2011-01-24 | 2012-08-02 | Glaxo Group Limited | Compounds useful as retinoid-related orphan receptor gamma modulators |
| WO2012107850A1 (en) | 2011-02-08 | 2012-08-16 | Pfizer Inc. | Glucagon receptor modulator |
| PH12013501686A1 (en) | 2011-02-25 | 2017-10-25 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| KR20140023441A (ko) | 2011-07-22 | 2014-02-26 | 화이자 인코포레이티드 | 퀴놀린일 글루카곤 수용체 조절제 |
| CA2880901A1 (en) | 2012-08-02 | 2014-02-06 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| KR20150087400A (ko) | 2012-11-20 | 2015-07-29 | 버텍스 파마슈티칼스 인코포레이티드 | 인돌아민 2,3-디옥시게나제의 억제제로서 유용한 화합물 |
| RU2015140066A (ru) | 2013-02-22 | 2017-03-30 | Мерк Шарп И Доум Корп. | Противодиабетические бициклические соединения |
| TW201444798A (zh) | 2013-02-28 | 2014-12-01 | 必治妥美雅史谷比公司 | 作爲強效ｒｏｃｋ１及ｒｏｃｋ２抑制劑之苯基吡唑衍生物 |
| US9828345B2 (en) | 2013-02-28 | 2017-11-28 | Bristol-Myers Squibb Company | Phenylpyrazole derivatives as potent ROCK1 and ROCK2 inhibitors |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| EP3126358A1 (de) | 2014-04-03 | 2017-02-08 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituierte cyclopentancarbonsäuren zur behandlung von atemwegserkrankungen |
| US20170022171A1 (en) | 2014-04-03 | 2017-01-26 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituted cyclopentanecarboxylic acids and their use |
| WO2015150362A2 (de) | 2014-04-03 | 2015-10-08 | Bayer Pharma Aktiengesellschaft | Chirale 2,5-disubstituierte cyclopentancarbonsäure-derivate und ihre verwendung |
| CN109071423A (zh) | 2016-02-09 | 2018-12-21 | 益方生物科技（上海）有限公司 | 吲哚胺-2,3-双加氧酶(ido)抑制剂 |
| CN106632076B (zh) * | 2016-09-20 | 2019-04-30 | 中国药科大学 | 4,6-二苯基嘧啶类化合物、其制备方法和医药用途 |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| KR102606541B1 (ko) * | 2021-04-23 | 2023-11-29 | 가천대학교 산학협력단 | 바이페닐설폰아마이드 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 글루카곤 수용체 활성 관련 질환의 예방 또는 치료용 약학적 조성물 |
| CN115337301A (zh) * | 2022-07-22 | 2022-11-15 | 汕头大学医学院第一附属医院 | Anle138b在制备改善饮食诱导胰岛素抵抗药物中的应用 |
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-
2004
- 2004-04-14 WO PCT/US2004/011650 patent/WO2004092146A2/en not_active Ceased
- 2004-04-14 US US10/824,057 patent/US20040248937A1/en not_active Abandoned
- 2004-04-14 CA CA002522080A patent/CA2522080A1/en not_active Abandoned
- 2004-04-14 EP EP04750170A patent/EP1633354B1/en not_active Expired - Lifetime
- 2004-04-14 EA EA200501607A patent/EA200501607A1/ru unknown
- 2004-04-14 JP JP2006510073A patent/JP2006524248A/ja active Pending
- 2004-04-14 DE DE602004011511T patent/DE602004011511T2/de not_active Expired - Fee Related
- 2004-04-14 AU AU2004231106A patent/AU2004231106A1/en not_active Abandoned
- 2004-04-14 CN CNA2004800145768A patent/CN1794989A/zh active Pending
- 2004-04-14 MX MXPA05010937A patent/MXPA05010937A/es unknown
- 2004-04-14 BR BRPI0409447-6A patent/BRPI0409447A/pt not_active IP Right Cessation
- 2004-04-14 KR KR1020057019661A patent/KR20050121732A/ko not_active Withdrawn
- 2004-04-14 AT AT04750170T patent/ATE384526T1/de not_active IP Right Cessation
-
2005
- 2005-10-17 NO NO20054769A patent/NO20054769L/no not_active Application Discontinuation
- 2005-11-11 ZA ZA200509123A patent/ZA200509123B/en unknown
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