JP2007511485A5 - - Google Patents
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- JP2007511485A5 JP2007511485A5 JP2006538823A JP2006538823A JP2007511485A5 JP 2007511485 A5 JP2007511485 A5 JP 2007511485A5 JP 2006538823 A JP2006538823 A JP 2006538823A JP 2006538823 A JP2006538823 A JP 2006538823A JP 2007511485 A5 JP2007511485 A5 JP 2007511485A5
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- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- pyrazol
- amino
- carbonyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- -1 morpholino, pyrrolidino, piperidino, thiophenyl Chemical group 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 claims 3
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims 3
- 208000022531 anorexia Diseases 0.000 claims 3
- 206010061428 decreased appetite Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- BMCXRYMMKLEOTJ-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-1-methylpyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C(C)(C)C)=C2)=C1 BMCXRYMMKLEOTJ-UHFFFAOYSA-N 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- STQUOPOPURPPAC-UHFFFAOYSA-N 2-[2-chloro-6-methyl-4-[[[1-methyl-5-[4-(2-methylpropyl)phenyl]pyrazole-3-carbonyl]amino]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(C(=O)NCC=2C=C(Cl)C(OC(C)(C)C(O)=O)=C(C)C=2)=NN1C STQUOPOPURPPAC-UHFFFAOYSA-N 0.000 claims 1
- FLKLKHZVPKKAHT-UHFFFAOYSA-N 2-[2-methoxy-4-[[[1-methyl-5-(4-propan-2-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(OC)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C(C)C)=C2)=C1 FLKLKHZVPKKAHT-UHFFFAOYSA-N 0.000 claims 1
- DSQDXGANBLAVCL-UHFFFAOYSA-N 2-[2-methoxy-4-[[[1-methyl-5-[4-(2-methylpropyl)phenyl]pyrazole-3-carbonyl]amino]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(OC)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(CC(C)C)=CC=3)=C2)=C1 DSQDXGANBLAVCL-UHFFFAOYSA-N 0.000 claims 1
- GKTGWVSKNNYTPC-UHFFFAOYSA-N 2-[2-methoxy-4-[[[2-methyl-5-(4-propan-2-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(OC)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C(C)C)C)=C1 GKTGWVSKNNYTPC-UHFFFAOYSA-N 0.000 claims 1
- POJKJAGKSKBXAQ-UHFFFAOYSA-N 2-[4-[[[1-benzyl-5-(4-tert-butylphenyl)pyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(CC=3C=CC=CC=3)C(C=3C=CC(=CC=3)C(C)(C)C)=C2)=C1 POJKJAGKSKBXAQ-UHFFFAOYSA-N 0.000 claims 1
- ZIKHPLAYCZPPPB-UHFFFAOYSA-N 2-[4-[[[2-[5-(4-tert-butylphenyl)-1-methylpyrazol-3-yl]acetyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)CC2=NN(C)C(C=3C=CC(=CC=3)C(C)(C)C)=C2)=C1 ZIKHPLAYCZPPPB-UHFFFAOYSA-N 0.000 claims 1
- RHYXFZPDGPLDTQ-UHFFFAOYSA-N 2-[4-[[[2-[5-(4-tert-butylphenyl)-2-methylpyrazol-3-yl]acetyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)CC=2N(N=C(C=2)C=2C=CC(=CC=2)C(C)(C)C)C)=C1 RHYXFZPDGPLDTQ-UHFFFAOYSA-N 0.000 claims 1
- ZQFFCRTYQIETBZ-UHFFFAOYSA-N 2-[4-[[[2-benzyl-5-(4-tert-butylphenyl)pyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C(C)(C)C)CC=2C=CC=CC=2)=C1 ZQFFCRTYQIETBZ-UHFFFAOYSA-N 0.000 claims 1
- IFNFZYFWAKNNLC-UHFFFAOYSA-N 2-[4-[[[3-(4-tert-butylphenyl)-1h-pyrazole-5-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NNC(=C2)C=2C=CC(=CC=2)C(C)(C)C)=C1 IFNFZYFWAKNNLC-UHFFFAOYSA-N 0.000 claims 1
- AEXZSCUBUIJTHV-UHFFFAOYSA-N 2-[4-[[[5-(4-butylphenyl)-1-methylpyrazole-3-carbonyl]amino]methyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(CCCC)=CC=C1C1=CC(C(=O)NCC=2C=C(C)C(OC(C)(C)C(O)=O)=C(C)C=2)=NN1C AEXZSCUBUIJTHV-UHFFFAOYSA-N 0.000 claims 1
- OMPVSODEIZVPQA-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-1-(2-methoxyethyl)pyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound COCCN1N=C(C(=O)NCC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)C=C1C1=CC=C(C(C)(C)C)C=C1 OMPVSODEIZVPQA-UHFFFAOYSA-N 0.000 claims 1
- WHIJGRIOJCKYQC-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-1-(2-morpholin-4-ylethyl)pyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid;hydrochloride Chemical compound Cl.C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(CCN3CCOCC3)C(C=3C=CC(=CC=3)C(C)(C)C)=C2)=C1 WHIJGRIOJCKYQC-UHFFFAOYSA-N 0.000 claims 1
- RRZTUCGMIFUIDD-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-1-ethylpyrazole-3-carbonyl]amino]methyl]-2-methoxyphenoxy]-2-methylpropanoic acid Chemical compound CCN1N=C(C(=O)NCC=2C=C(OC)C(OC(C)(C)C(O)=O)=CC=2)C=C1C1=CC=C(C(C)(C)C)C=C1 RRZTUCGMIFUIDD-UHFFFAOYSA-N 0.000 claims 1
- AUKXWOYKKNDADD-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-1-ethylpyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound CCN1N=C(C(=O)NCC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)C=C1C1=CC=C(C(C)(C)C)C=C1 AUKXWOYKKNDADD-UHFFFAOYSA-N 0.000 claims 1
- ASNQEFKXXIMVQR-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-1-methylpyrazole-3-carbonyl]amino]methyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound CC1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C(C)(C)C)=C2)=C1 ASNQEFKXXIMVQR-UHFFFAOYSA-N 0.000 claims 1
- VBJNROFWFNODQW-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-1-methylpyrazole-3-carbonyl]amino]methyl]phenoxy]-2-methylpropanoic acid Chemical compound CN1N=C(C(=O)NCC=2C=CC(OC(C)(C)C(O)=O)=CC=2)C=C1C1=CC=C(C(C)(C)C)C=C1 VBJNROFWFNODQW-UHFFFAOYSA-N 0.000 claims 1
- SXMPFVUTKBRPST-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-1-prop-2-enylpyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(CC=C)C(C=3C=CC(=CC=3)C(C)(C)C)=C2)=C1 SXMPFVUTKBRPST-UHFFFAOYSA-N 0.000 claims 1
- HZIOXHZMCMSLJZ-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-(2-methoxyethyl)pyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound COCCN1N=C(C=2C=CC(=CC=2)C(C)(C)C)C=C1C(=O)NCC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 HZIOXHZMCMSLJZ-UHFFFAOYSA-N 0.000 claims 1
- SHADJSKBHZSPQD-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-(2-morpholin-4-ylethyl)pyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C(C)(C)C)CCN2CCOCC2)=C1 SHADJSKBHZSPQD-UHFFFAOYSA-N 0.000 claims 1
- RWNOJGMOKSIOJQ-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-ethylpyrazole-3-carbonyl]amino]methyl]-2-methoxyphenoxy]-2-methylpropanoic acid Chemical compound CCN1N=C(C=2C=CC(=CC=2)C(C)(C)C)C=C1C(=O)NCC1=CC=C(OC(C)(C)C(O)=O)C(OC)=C1 RWNOJGMOKSIOJQ-UHFFFAOYSA-N 0.000 claims 1
- OTOWLPBTZHONBE-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-ethylpyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound CCN1N=C(C=2C=CC(=CC=2)C(C)(C)C)C=C1C(=O)NCC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 OTOWLPBTZHONBE-UHFFFAOYSA-N 0.000 claims 1
- OPCCRUAQNXTYGB-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-methylpyrazole-3-carbonyl]amino]methyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound CC1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C(C)(C)C)C)=C1 OPCCRUAQNXTYGB-UHFFFAOYSA-N 0.000 claims 1
- RWSQTZOKSVLYSJ-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-methylpyrazole-3-carbonyl]amino]methyl]-2-methoxyphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(OC)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C(C)(C)C)C)=C1 RWSQTZOKSVLYSJ-UHFFFAOYSA-N 0.000 claims 1
- QWVAVDLPTMWMGV-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-methylpyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C(C)(C)C)C)=C1 QWVAVDLPTMWMGV-UHFFFAOYSA-N 0.000 claims 1
- MAOVVAJEAXSPFU-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-methylpyrazole-3-carbonyl]amino]methyl]-2-prop-2-enylphenoxy]-2-methylpropanoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)C(C)(C)C)C=C1C(=O)NCC1=CC=C(OC(C)(C)C(O)=O)C(CC=C)=C1 MAOVVAJEAXSPFU-UHFFFAOYSA-N 0.000 claims 1
- MGQNNPJXCUIFFA-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-methylpyrazole-3-carbonyl]amino]methyl]-2-propylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(CCC)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C(C)(C)C)C)=C1 MGQNNPJXCUIFFA-UHFFFAOYSA-N 0.000 claims 1
- MNZSYDYUUQTJOB-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-methylpyrazole-3-carbonyl]amino]methyl]phenoxy]-2-methylpropanoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)C(C)(C)C)C=C1C(=O)NCC1=CC=C(OC(C)(C)C(O)=O)C=C1 MNZSYDYUUQTJOB-UHFFFAOYSA-N 0.000 claims 1
- DZHZNVPNJXPNRR-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-prop-2-enylpyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C(C)(C)C)CC=C)=C1 DZHZNVPNJXPNRR-UHFFFAOYSA-N 0.000 claims 1
- IUVBHXFYFQQYNU-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-prop-2-enylpyrazole-3-carbonyl]amino]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN(CC=C)C(C(=O)NCC=2C=CC(OC(C)(C)C(O)=O)=CC=2)=C1 IUVBHXFYFQQYNU-UHFFFAOYSA-N 0.000 claims 1
- JIOKCDDFLAVCGR-UHFFFAOYSA-N 2-[4-[[[5-[(4-tert-butylphenyl)methyl]-2-methylpyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(CC=3C=CC(=CC=3)C(C)(C)C)C=2)C)=C1 JIOKCDDFLAVCGR-UHFFFAOYSA-N 0.000 claims 1
- APWBHRHPRDNQFL-UHFFFAOYSA-N 2-[4-[[[5-[4-(furan-2-yl)phenyl]-1-methylpyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C=3OC=CC=3)=C2)=C1 APWBHRHPRDNQFL-UHFFFAOYSA-N 0.000 claims 1
- XMOANMMSPJBNRJ-UHFFFAOYSA-N 2-[4-[[[5-[4-(furan-3-yl)phenyl]-1-methylpyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C3=COC=C3)=C2)=C1 XMOANMMSPJBNRJ-UHFFFAOYSA-N 0.000 claims 1
- PHJROTQNLZGIOE-UHFFFAOYSA-N 2-[5-[[[5-(4-tert-butylphenyl)-2-(2-phenylethyl)pyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC=C1CNC(=O)C1=CC(C=2C=CC(=CC=2)C(C)(C)C)=NN1CCC1=CC=CC=C1 PHJROTQNLZGIOE-UHFFFAOYSA-N 0.000 claims 1
- CBNBIAHEHQQVDG-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(3-piperidin-1-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=C(C=CC=3)N3CCCCC3)=C2)=C1 CBNBIAHEHQQVDG-UHFFFAOYSA-N 0.000 claims 1
- IOSMRGMGAZMMBG-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(3-pyrrolidin-1-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=C(C=CC=3)N3CCCC3)=C2)=C1 IOSMRGMGAZMMBG-UHFFFAOYSA-N 0.000 claims 1
- HQQOFEIOQWARCX-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-morpholin-4-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)N3CCOCC3)=C2)=C1 HQQOFEIOQWARCX-UHFFFAOYSA-N 0.000 claims 1
- DHHNCATZTSKAKM-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-phenylmethoxyphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(OCC=4C=CC=CC=4)=CC=3)=C2)=C1 DHHNCATZTSKAKM-UHFFFAOYSA-N 0.000 claims 1
- SMURNEUIYATOSV-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-phenylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C=3C=CC=CC=3)=C2)=C1 SMURNEUIYATOSV-UHFFFAOYSA-N 0.000 claims 1
- JSTDJUSSZHCXGB-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-piperidin-1-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)N3CCCCC3)=C2)=C1 JSTDJUSSZHCXGB-UHFFFAOYSA-N 0.000 claims 1
- VFDBFQYMWTVKKS-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-prop-2-enoxyphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(OCC=C)=CC=3)=C2)=C1 VFDBFQYMWTVKKS-UHFFFAOYSA-N 0.000 claims 1
- ICQSHZWOSZQXQP-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-propan-2-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=CC(C(=O)NCC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)=NN1C ICQSHZWOSZQXQP-UHFFFAOYSA-N 0.000 claims 1
- UFKREXXXYPUDAP-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-pyridin-4-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C=3C=CN=CC=3)=C2)=C1 UFKREXXXYPUDAP-UHFFFAOYSA-N 0.000 claims 1
- JPQLNXQUXRQYHE-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-pyrrolidin-1-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)N3CCCC3)=C2)=C1 JPQLNXQUXRQYHE-UHFFFAOYSA-N 0.000 claims 1
- XYNWLLGKTZMMCR-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-thiophen-2-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C=3SC=CC=3)=C2)=C1 XYNWLLGKTZMMCR-UHFFFAOYSA-N 0.000 claims 1
- BIPCJUYHEQBDLC-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-[4-(2-methylphenyl)phenyl]pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C=3C(=CC=CC=3)C)=C2)=C1 BIPCJUYHEQBDLC-UHFFFAOYSA-N 0.000 claims 1
- RZKIWMZPDRGCSP-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-[4-(2-methylpropyl)phenyl]pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(C(=O)NCC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)=NN1C RZKIWMZPDRGCSP-UHFFFAOYSA-N 0.000 claims 1
- OBVBKFWKMJVFQB-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(3-phenylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)C)=C1 OBVBKFWKMJVFQB-UHFFFAOYSA-N 0.000 claims 1
- GHJWPZBMWRTWTP-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(3-piperidin-1-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=C(C=CC=2)N2CCCCC2)C)=C1 GHJWPZBMWRTWTP-UHFFFAOYSA-N 0.000 claims 1
- VPNFXFZPZROYOJ-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(3-pyrrolidin-1-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=C(C=CC=2)N2CCCC2)C)=C1 VPNFXFZPZROYOJ-UHFFFAOYSA-N 0.000 claims 1
- KTSNEFUVGDGYSM-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(4-morpholin-4-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)N2CCOCC2)C)=C1 KTSNEFUVGDGYSM-UHFFFAOYSA-N 0.000 claims 1
- UFGQMVJKSOQAMR-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(4-phenylmethoxyphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C)=C1 UFGQMVJKSOQAMR-UHFFFAOYSA-N 0.000 claims 1
- ZAFYJKLGONVCNU-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(4-piperidin-1-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)N2CCCCC2)C)=C1 ZAFYJKLGONVCNU-UHFFFAOYSA-N 0.000 claims 1
- XGRRRLKUALPLQN-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(4-prop-2-enoxyphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(OCC=C)=CC=2)C)=C1 XGRRRLKUALPLQN-UHFFFAOYSA-N 0.000 claims 1
- IHMYTWLHTOGGRA-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(4-propan-2-ylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=NN(C)C(C(=O)NCC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)=C1 IHMYTWLHTOGGRA-UHFFFAOYSA-N 0.000 claims 1
- HUHYEXVSWOSGEP-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-[4-(2-methylphenyl)phenyl]pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C=2C(=CC=CC=2)C)C)=C1 HUHYEXVSWOSGEP-UHFFFAOYSA-N 0.000 claims 1
- QASOYNCNSYBPTE-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-[4-(2-methylpropyl)phenyl]pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=NN(C)C(C(=O)NCC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)=C1 QASOYNCNSYBPTE-UHFFFAOYSA-N 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 208000032841 Bulimia Diseases 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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| GB0326747A GB0326747D0 (en) | 2003-11-17 | 2003-11-17 | Chemical compounds |
| GB0329462A GB0329462D0 (en) | 2003-12-19 | 2003-12-19 | Chemical compounds |
| PCT/EP2004/012965 WO2005049578A1 (en) | 2003-11-17 | 2004-11-15 | Substituted pyrazoles as ppar agonists |
Publications (2)
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| JP2007511485A JP2007511485A (ja) | 2007-05-10 |
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| JP (1) | JP2007511485A (https=) |
| AR (1) | AR046625A1 (https=) |
| AT (1) | ATE402926T1 (https=) |
| DE (1) | DE602004015498D1 (https=) |
| ES (1) | ES2311179T3 (https=) |
| TW (1) | TW200526588A (https=) |
| WO (1) | WO2005049578A1 (https=) |
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| US20080064682A1 (en) * | 2004-07-01 | 2008-03-13 | Daiichi Pharmaceutical Co., Ltd. | Pyrazole Derivatives |
| RU2007135745A (ru) * | 2005-02-28 | 2009-04-10 | Ниппон Кемифар Ко., Лтд. (JP) | АКТИВАТОР δ- РЕЦЕПТОРА, АКТИВИРУЕМОГО ПРОЛИФЕРАТОРОМ ПЕРОКСИСОМЫ |
| US8703805B2 (en) * | 2005-06-27 | 2014-04-22 | Exelixis Patent Company Llc | Modulators of LXR |
| CN101466687B (zh) | 2006-04-18 | 2012-04-11 | 日本化学医药株式会社 | 过氧化物酶体增殖剂激活受体δ的激活剂 |
| KR20090094125A (ko) | 2006-12-08 | 2009-09-03 | 엑셀리시스, 인코포레이티드 | Ｌｘｒ 및 ｆｘｒ 조절자 |
| JP2010523623A (ja) * | 2007-04-11 | 2010-07-15 | グラクソ グループ リミテッド | Ｐ２ｘ７調節因子としてのピラゾール誘導体 |
| MX2010011252A (es) | 2008-04-15 | 2010-11-30 | Nippon Chemiphar Co | Activador para el receptor activado por el proliferador de peroxisoma. |
| WO2010058858A1 (ja) * | 2008-11-21 | 2010-05-27 | ラクオリア創薬株式会社 | ５－ｈｔ２ｂ受容体拮抗活性を有する新規ピラゾール－３－カルボキサミド誘導体 |
| UY32826A (es) | 2009-08-04 | 2011-02-28 | Takeda Pharmaceutical | Compuestos heterocíclicos |
| KR101758201B1 (ko) * | 2009-12-15 | 2017-07-14 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 1-알킬-/1-아릴-5-피라졸카복실산 유도체의 제조방법 |
| TWI508968B (zh) | 2010-02-08 | 2015-11-21 | Biota Scient Management | 用於治療呼吸道融合性病毒感染的化合物 |
| JP6155187B2 (ja) | 2010-03-30 | 2017-06-28 | ヴァーセオン コーポレイション | トロンビンの阻害剤としての多置換芳香族化合物 |
| CN101870676B (zh) * | 2010-06-24 | 2011-09-07 | 山东大学 | 1-(2-肟基-2-苯基乙基)-3-苯基-1h-吡唑-5-甲酸乙酯衍生物及其制备与应用 |
| CN110179795A (zh) | 2013-03-15 | 2019-08-30 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的多取代芳族化合物的制药用途 |
| HK1214252A1 (zh) | 2013-03-15 | 2016-07-22 | Verseon Corporation | 作為凝血酶抑制劑的鹵代吡唑 |
| TWI636047B (zh) | 2013-08-14 | 2018-09-21 | 英商卡爾維斯塔製藥有限公司 | 雜環衍生物 |
| US10189810B2 (en) | 2014-09-17 | 2019-01-29 | Verseon Corporation | Pyrazolyl-substituted pyridone compounds as serine protease inhibitors |
| GB201421085D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | New enzyme inhibitors |
| GB201421083D0 (en) * | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | Enzyme inhibitors |
| CN107405333A (zh) | 2015-02-27 | 2017-11-28 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的被取代的吡唑化合物 |
| IL263235B (en) | 2016-05-31 | 2022-07-01 | Kalvista Pharmaceuticals Ltd | History of pyrazoles as plasma kallikrein inhibitors |
| GB201609607D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts |
| GB201609603D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-[(6-cyano-2-fluoro-3-methoxyphenyl)Methyl]-3-(methoxymethyl)-1-({4-[(2-ox opyridin-1-YL)Methyl]phenyl}methyl)pyrazole-4-carboxamide |
| CN110087667A (zh) | 2016-08-16 | 2019-08-02 | 隐形生物治疗公司 | Elamipretide的基于N-羧基酸酐的规模合成 |
| WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| HUE057912T2 (hu) | 2017-11-29 | 2022-06-28 | Kalvista Pharmaceuticals Ltd | Plazma kallikrein inhibitort tartalmazó dózisformák |
| TWI805699B (zh) | 2018-03-01 | 2023-06-21 | 日商日本煙草產業股份有限公司 | 甲基內醯胺環化合物及其用途 |
| MX2020010433A (es) | 2018-04-04 | 2020-10-28 | Japan Tobacco Inc | Compuestos de pirazol sustituidos con heteroarilo y uso farmaceutico de los mismos. |
| JP2021528405A (ja) * | 2018-06-18 | 2021-10-21 | ヤンセン ファーマシューティカ エヌ．ベー． | ＲＯＲγｔのモジュレータとしてのアミド置換チアゾール |
| WO2021028645A1 (en) | 2019-08-09 | 2021-02-18 | Kalvista Pharmaceuticals Limited | Plasma kallikrein inhibitors |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3621775A1 (de) * | 1986-03-13 | 1988-01-07 | Thomae Gmbh Dr K | Neue substituierte thiazole und oxazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| IL135177A0 (en) * | 1997-10-02 | 2001-05-20 | Sankyo Co | Amidocarboxylic acid derivatives and pharmaceutical compositions containing the same |
| HK1045991B (en) * | 1999-11-10 | 2004-12-10 | Takeda Pharmaceutical Company Limited | 5-membered n-heterocyclic compounds with hypoglycemic and hypolipidemic activity |
| PE20011010A1 (es) * | 1999-12-02 | 2001-10-18 | Glaxo Group Ltd | Oxazoles y tiazoles sustituidos como agonista del receptor activado por el proliferador de peroxisomas humano |
| JP3372923B2 (ja) * | 2000-02-25 | 2003-02-04 | エヌイーシーマイクロシステム株式会社 | 半導体集積回路 |
| US7319104B2 (en) * | 2002-03-01 | 2008-01-15 | Smithkline Beecham Corporation | hPPARs activators |
-
2004
- 2004-11-12 TW TW093134800A patent/TW200526588A/zh unknown
- 2004-11-15 WO PCT/EP2004/012965 patent/WO2005049578A1/en not_active Ceased
- 2004-11-15 DE DE602004015498T patent/DE602004015498D1/de not_active Expired - Fee Related
- 2004-11-15 JP JP2006538823A patent/JP2007511485A/ja active Pending
- 2004-11-15 AT AT04818779T patent/ATE402926T1/de not_active IP Right Cessation
- 2004-11-15 US US10/595,868 patent/US20080021030A1/en not_active Abandoned
- 2004-11-15 ES ES04818779T patent/ES2311179T3/es not_active Expired - Lifetime
- 2004-11-15 EP EP04818779A patent/EP1685113B1/en not_active Expired - Lifetime
- 2004-11-15 AR ARP040104209A patent/AR046625A1/es unknown
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