JP2007527416A5 - - Google Patents
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- JP2007527416A5 JP2007527416A5 JP2006538316A JP2006538316A JP2007527416A5 JP 2007527416 A5 JP2007527416 A5 JP 2007527416A5 JP 2006538316 A JP2006538316 A JP 2006538316A JP 2006538316 A JP2006538316 A JP 2006538316A JP 2007527416 A5 JP2007527416 A5 JP 2007527416A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- thiadiazol
- phenyl
- phenoxy
- propionic acid
- 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 33
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 229910052799 carbon Inorganic materials 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 12
- -1 chloro, methyl Chemical group 0.000 claims 11
- 239000002253 acid Substances 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 230000001404 mediated effect Effects 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- NWOQGTFCVBLDHG-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[3-[4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCC=2SN=C(N=2)C=2C=CC(OC(F)(F)F)=CC=2)=C1 NWOQGTFCVBLDHG-UHFFFAOYSA-N 0.000 claims 4
- VNJJEMOMRQCJFH-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCC=2SN=C(N=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 VNJJEMOMRQCJFH-UHFFFAOYSA-N 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- ODCHEZKQADNMGG-UHFFFAOYSA-N 2-[4-[[3-(3,4-dichlorophenyl)-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=C(Cl)C(Cl)=CC=2)=C1 ODCHEZKQADNMGG-UHFFFAOYSA-N 0.000 claims 3
- IYNGJYKTRDXUDJ-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[3-[4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=CC(OC(F)(F)F)=CC=2)=C1 IYNGJYKTRDXUDJ-UHFFFAOYSA-N 0.000 claims 3
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims 3
- 102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 238000009472 formulation Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims 3
- 108091008765 peroxisome proliferator-activated receptors β/δ Proteins 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- GPMFVXQGEDONAI-UHFFFAOYSA-N 2-[4-[2-[3-[3-chloro-4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]ethylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCCC=2SN=C(N=2)C=2C=C(Cl)C(=CC=2)C(F)(F)F)=C1 GPMFVXQGEDONAI-UHFFFAOYSA-N 0.000 claims 2
- HLHWPILWJFQPRD-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 HLHWPILWJFQPRD-UHFFFAOYSA-N 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 2
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- VKQSDPFDBIOVSF-UHFFFAOYSA-N 1-[2-methyl-4-[[3-[4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]methylsulfanyl]phenoxy]cyclopentane-1-carboxylic acid Chemical compound C=1C=C(OC2(CCCC2)C(O)=O)C(C)=CC=1SCC(SN=1)=NC=1C1=CC=C(OC(F)(F)F)C=C1 VKQSDPFDBIOVSF-UHFFFAOYSA-N 0.000 claims 1
- WPEUTERXVLVBJD-UHFFFAOYSA-N 1-[4-[[3-(3,4-dichlorophenyl)-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenoxy]cyclopentane-1-carboxylic acid Chemical compound C=1C=C(OC2(CCCC2)C(O)=O)C(C)=CC=1SCC(SN=1)=NC=1C1=CC=C(Cl)C(Cl)=C1 WPEUTERXVLVBJD-UHFFFAOYSA-N 0.000 claims 1
- BHZIXCXGFDVCEL-UHFFFAOYSA-N 2-[2-methyl-4-[[3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 BHZIXCXGFDVCEL-UHFFFAOYSA-N 0.000 claims 1
- YNXASAKCMJFZFR-UHFFFAOYSA-N 2-[4-[2-[3-(3,4-dichlorophenyl)-1,2,4-thiadiazol-5-yl]ethoxy]-2-methylphenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(OCCC=2SN=C(N=2)C=2C=C(Cl)C(Cl)=CC=2)=C1 YNXASAKCMJFZFR-UHFFFAOYSA-N 0.000 claims 1
- GSHLBDIEADYNJN-UHFFFAOYSA-N 2-[4-[2-[3-(3,4-dichlorophenyl)-1,2,4-thiadiazol-5-yl]ethylsulfanyl]-2-methylphenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(SCCC=2SN=C(N=2)C=2C=C(Cl)C(Cl)=CC=2)=C1 GSHLBDIEADYNJN-UHFFFAOYSA-N 0.000 claims 1
- XGEZXSQEKKWDLW-UHFFFAOYSA-N 2-[4-[2-[3-(3-fluoro-4-methylphenyl)-1,2,4-thiadiazol-5-yl]ethyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(F)C(C)=CC=C1C1=NSC(CCC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)=N1 XGEZXSQEKKWDLW-UHFFFAOYSA-N 0.000 claims 1
- MERINUFDYVZFQP-UHFFFAOYSA-N 2-[4-[2-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]ethoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCCC=2SN=C(N=2)C=2C=C(Cl)C(OC(F)(F)F)=CC=2)=C1 MERINUFDYVZFQP-UHFFFAOYSA-N 0.000 claims 1
- JFFSHPMRLQULRT-UHFFFAOYSA-N 2-[4-[2-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]ethoxy]-2-methylphenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(OCCC=2SN=C(N=2)C=2C=C(Cl)C(OC(F)(F)F)=CC=2)=C1 JFFSHPMRLQULRT-UHFFFAOYSA-N 0.000 claims 1
- KXQOZDPRHUGYAO-UHFFFAOYSA-N 2-[4-[2-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]ethyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CCC=2SN=C(N=2)C=2C=C(Cl)C(OC(F)(F)F)=CC=2)=C1 KXQOZDPRHUGYAO-UHFFFAOYSA-N 0.000 claims 1
- DHSAJVJECPVWRM-UHFFFAOYSA-N 2-[4-[2-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]ethylsulfanyl]-2-methylphenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(SCCC=2SN=C(N=2)C=2C=C(Cl)C(OC(F)(F)F)=CC=2)=C1 DHSAJVJECPVWRM-UHFFFAOYSA-N 0.000 claims 1
- RKAYVGWXNZOPAD-UHFFFAOYSA-N 2-[4-[2-[3-[3-chloro-4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]ethyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CCC=2SN=C(N=2)C=2C=C(Cl)C(=CC=2)C(F)(F)F)=C1 RKAYVGWXNZOPAD-UHFFFAOYSA-N 0.000 claims 1
- FMQGRVGNXNWEQI-UHFFFAOYSA-N 2-[4-[2-[3-[3-fluoro-4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]ethyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CCC=2SN=C(N=2)C=2C=C(F)C(=CC=2)C(F)(F)F)=C1 FMQGRVGNXNWEQI-UHFFFAOYSA-N 0.000 claims 1
- QDHGUQJAWFDXPA-UHFFFAOYSA-N 2-[4-[[3-(2,4-dichlorophenyl)-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C(=CC(Cl)=CC=2)Cl)=C1 QDHGUQJAWFDXPA-UHFFFAOYSA-N 0.000 claims 1
- MXHMPCCXYYUBRL-UHFFFAOYSA-N 2-[4-[[3-(3,4-dichlorophenyl)-1,2,4-thiadiazol-5-yl]methoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCC=2SN=C(N=2)C=2C=C(Cl)C(Cl)=CC=2)=C1 MXHMPCCXYYUBRL-UHFFFAOYSA-N 0.000 claims 1
- UFACEIGLNAMLPU-UHFFFAOYSA-N 2-[4-[[3-(3,4-dichlorophenyl)-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=C(Cl)C(Cl)=CC=2)=C1 UFACEIGLNAMLPU-UHFFFAOYSA-N 0.000 claims 1
- BIEZLHAQUMPLCK-UHFFFAOYSA-N 2-[4-[[3-(3,4-dimethylphenyl)-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(C)C(C)=CC=C1C1=NSC(CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)=N1 BIEZLHAQUMPLCK-UHFFFAOYSA-N 0.000 claims 1
- QKPRBQKBZSCFSF-UHFFFAOYSA-N 2-[4-[[3-(3-chloro-4-methylphenyl)-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(Cl)C(C)=CC=C1C1=NSC(CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)=N1 QKPRBQKBZSCFSF-UHFFFAOYSA-N 0.000 claims 1
- DXYOPAUYEVLJOE-UHFFFAOYSA-N 2-[4-[[3-(3-fluoro-4-methylphenyl)-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=C(F)C(C)=CC=C1C1=NSC(CSC=2C=C(C)C(SC(C)(C)C(O)=O)=CC=2)=N1 DXYOPAUYEVLJOE-UHFFFAOYSA-N 0.000 claims 1
- CHWARMCOUPSGEK-UHFFFAOYSA-N 2-[4-[[3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=CC(Cl)=CC=2)=C1 CHWARMCOUPSGEK-UHFFFAOYSA-N 0.000 claims 1
- RZGXJNCOBNXAPV-UHFFFAOYSA-N 2-[4-[[3-(4-tert-butylphenyl)-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=CC(=CC=2)C(C)(C)C)=C1 RZGXJNCOBNXAPV-UHFFFAOYSA-N 0.000 claims 1
- QSJXRYSFKIOKCA-UHFFFAOYSA-N 2-[4-[[3-(4-tert-butylphenyl)-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=CC(=CC=2)C(C)(C)C)=C1 QSJXRYSFKIOKCA-UHFFFAOYSA-N 0.000 claims 1
- MJILFCJFAXMPDJ-UHFFFAOYSA-N 2-[4-[[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]methoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCC=2SN=C(N=2)C=2C=C(Cl)C(OC(F)(F)F)=CC=2)=C1 MJILFCJFAXMPDJ-UHFFFAOYSA-N 0.000 claims 1
- MYVWFBUMMXGFBZ-UHFFFAOYSA-N 2-[4-[[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=C(Cl)C(OC(F)(F)F)=CC=2)=C1 MYVWFBUMMXGFBZ-UHFFFAOYSA-N 0.000 claims 1
- JRDRAZYHPGCBPO-UHFFFAOYSA-N 2-[4-[[3-[3-chloro-4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=C(Cl)C(=CC=2)C(F)(F)F)=C1 JRDRAZYHPGCBPO-UHFFFAOYSA-N 0.000 claims 1
- JEWOTCVMOJUQPP-UHFFFAOYSA-N 2-[4-[[3-[3-fluoro-4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]methylsulfanyl]-2-methylphenyl]sulfanyl-2-methylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=C(F)C(=CC=2)C(F)(F)F)=C1 JEWOTCVMOJUQPP-UHFFFAOYSA-N 0.000 claims 1
- NBVHBGMDNBBQCN-UHFFFAOYSA-N 2-[4-[[5-(4-chlorophenyl)-1,2,4-thiadiazol-3-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2N=C(SN=2)C=2C=CC(Cl)=CC=2)=C1 NBVHBGMDNBBQCN-UHFFFAOYSA-N 0.000 claims 1
- SQRNABWRYMDTPM-UHFFFAOYSA-N 2-[4-[[5-(4-tert-butylphenyl)-1,2,4-thiadiazol-3-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2N=C(SN=2)C=2C=CC(=CC=2)C(C)(C)C)=C1 SQRNABWRYMDTPM-UHFFFAOYSA-N 0.000 claims 1
- OPJBMQYIFRGFDI-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[2-[3-[4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]ethoxy]phenyl]sulfanylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(OCCC=2SN=C(N=2)C=2C=CC(OC(F)(F)F)=CC=2)=C1 OPJBMQYIFRGFDI-UHFFFAOYSA-N 0.000 claims 1
- MPLYDDLLNVJMRS-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[2-[3-[4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]ethylsulfanyl]phenyl]sulfanylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(SCCC=2SN=C(N=2)C=2C=CC(OC(F)(F)F)=CC=2)=C1 MPLYDDLLNVJMRS-UHFFFAOYSA-N 0.000 claims 1
- OMEMFMWVEOSCFL-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[2-[3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]ethylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCCC=2SN=C(N=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 OMEMFMWVEOSCFL-UHFFFAOYSA-N 0.000 claims 1
- KLYDUYZDMNRZRI-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[3-[3-[4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]propyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CCCC=2SN=C(N=2)C=2C=CC(OC(F)(F)F)=CC=2)=C1 KLYDUYZDMNRZRI-UHFFFAOYSA-N 0.000 claims 1
- NOGFMWFVYKCBFZ-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[3-[4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-5-yl]methylsulfanyl]phenyl]sulfanylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=CC(OC(F)(F)F)=CC=2)=C1 NOGFMWFVYKCBFZ-UHFFFAOYSA-N 0.000 claims 1
- KMTIQLGWRDJDQI-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]methylsulfanyl]phenyl]sulfanylpropanoic acid Chemical compound C1=C(SC(C)(C)C(O)=O)C(C)=CC(SCC=2SN=C(N=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 KMTIQLGWRDJDQI-UHFFFAOYSA-N 0.000 claims 1
- UVIJCJUVHLWTDI-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[5-(4-propan-2-ylphenyl)-1,2,4-thiadiazol-3-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(CSC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)=NS1 UVIJCJUVHLWTDI-UHFFFAOYSA-N 0.000 claims 1
- LEZYIYZIYKDSJI-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[5-[4-(trifluoromethoxy)phenyl]-1,2,4-thiadiazol-3-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2N=C(SN=2)C=2C=CC(OC(F)(F)F)=CC=2)=C1 LEZYIYZIYKDSJI-UHFFFAOYSA-N 0.000 claims 1
- RJFFDLMVDVMUFD-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[5-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-3-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2N=C(SN=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 RJFFDLMVDVMUFD-UHFFFAOYSA-N 0.000 claims 1
- LTSPOFAGKMZGON-UHFFFAOYSA-N 2-methyl-2-[4-[[3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCC1=NC(C=2C=CC(=CC=2)C(F)(F)F)=NS1 LTSPOFAGKMZGON-UHFFFAOYSA-N 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 0 C*(*c(cc1)c(*)c(*)c1N)C(*)* Chemical compound C*(*c(cc1)c(*)c(*)c1N)C(*)* 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51656103P | 2003-10-31 | 2003-10-31 | |
| PCT/US2004/036028 WO2005041959A1 (en) | 2003-10-31 | 2004-10-28 | Phenoxyacetic acids derivatives useful as peroxisome proliferator-activated receptor (ppar) dual agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007527416A JP2007527416A (ja) | 2007-09-27 |
| JP2007527416A5 true JP2007527416A5 (https=) | 2007-12-06 |
Family
ID=34549548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006538316A Withdrawn JP2007527416A (ja) | 2003-10-31 | 2004-10-28 | ペルオキシソーム増殖因子活性化受容体（ｐｐａｒ）二重作動薬として有用なフェノキシ酢酸誘導体 |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US7015329B2 (https=) |
| EP (1) | EP1684752B1 (https=) |
| JP (1) | JP2007527416A (https=) |
| KR (1) | KR20060109925A (https=) |
| CN (1) | CN1897939A (https=) |
| AR (1) | AR046311A1 (https=) |
| AT (1) | ATE362367T1 (https=) |
| AU (1) | AU2004285530A1 (https=) |
| BR (1) | BRPI0416106A (https=) |
| CA (1) | CA2544317A1 (https=) |
| CR (1) | CR8377A (https=) |
| DE (1) | DE602004006529T2 (https=) |
| EA (1) | EA009804B1 (https=) |
| EC (1) | ECSP066536A (https=) |
| ES (1) | ES2287786T3 (https=) |
| IL (1) | IL175310A0 (https=) |
| NO (1) | NO20062511L (https=) |
| TW (1) | TW200528438A (https=) |
| UA (1) | UA84035C2 (https=) |
| WO (1) | WO2005041959A1 (https=) |
| ZA (1) | ZA200604420B (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1667964B1 (en) | 2003-09-19 | 2009-07-22 | Janssen Pharmaceutica N.V. | 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs |
| CN1897939A (zh) * | 2003-10-31 | 2007-01-17 | 詹森药业有限公司 | 适用作过氧化物酶体增生物激活受体（ppar）双重激动剂的苯氧基乙酸衍生物 |
| US20080045580A1 (en) * | 2004-10-11 | 2008-02-21 | Dr Reddy's Laboratories Limited | Novel Isoxazole Compounds Having Ppar Agonist Activity |
| JO3006B1 (ar) | 2005-09-14 | 2016-09-05 | Janssen Pharmaceutica Nv | املاح ليسين مبتكرة من مشتقات حامض 4-((فينوكسي الكيل)ثيو) فينوكسي الخليك |
| UY30288A1 (es) * | 2006-04-18 | 2007-08-31 | Janssen Pharmaceutica Nv | Derivados del ácido benzoazepin-oxi-acético como agonistas de ppar-delta usados para aumentar hdl-c. reducir ldl-c y reducir colesterol |
| ES2399147T3 (es) | 2006-09-08 | 2013-03-26 | Rhode Island Hospital | Tratamiento, prevención y reversión de una enfermedad hepática alcohólica |
| US9308198B2 (en) | 2006-09-08 | 2016-04-12 | Rhode Island Hospital | Treatment, prevention, and reversal of alcohol-induced brain disease |
| US20160331729A9 (en) | 2007-04-11 | 2016-11-17 | Omeros Corporation | Compositions and methods for prophylaxis and treatment of addictions |
| EP3788877B1 (en) | 2007-04-11 | 2024-08-07 | Omeros Corporation | Compositions and methods for prophylaxis and treatment of addictions |
| US11241420B2 (en) | 2007-04-11 | 2022-02-08 | Omeros Corporation | Compositions and methods for prophylaxis and treatment of addictions |
| EP2310371B1 (fr) | 2008-05-26 | 2013-05-15 | Genfit | Composés agonistes ppar, préparation et utilisations pour le traitement du diabète et/ou des dyslipidémies |
| WO2012007500A2 (de) | 2010-07-15 | 2012-01-19 | Bayer Cropscience Ag | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| RU2013114390A (ru) | 2010-08-31 | 2014-10-10 | СНУ Ар энд ДиБи ФАУНДЕЙШН | Применение фетального репрограммирования посредством ppar-дельта-агониста |
| WO2012052412A1 (de) | 2010-10-22 | 2012-04-26 | Bayer Cropscience Ag | Neue heterocylische verbindungen als schädlingsbekämpfungsmittel |
| CA2871640A1 (en) | 2012-04-26 | 2013-10-31 | Bristol-Myers Squibb Company | Par4 agonist peptides |
| LT2841437T (lt) | 2012-04-26 | 2017-09-11 | Bristol-Myers Squibb Company | Imidazotiadiazolo ir imidazopirazino dariniai, kaip proteazės aktyvuotų receptorių 4 (par4) inhibitoriai, skirti trombocitų agregacijos gydymui |
| KR102750722B1 (ko) * | 2022-03-16 | 2025-01-09 | 재단법인 대구경북첨단의료산업진흥재단 | 싸이아다이아졸 화합물 및 이를 포함하는 염증성 질환의 예방 또는 치료용 약학적 조성물 |
| WO2024153134A1 (zh) * | 2023-01-18 | 2024-07-25 | 哈尔滨三联药业股份有限公司 | 五元杂环类化合物及其医药用途 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE451346T1 (de) * | 1998-03-10 | 2009-12-15 | Ono Pharmaceutical Co | Carbonsäurederivate und medikamente die diese als aktiven wirkstoff enthalten |
| US6242493B1 (en) | 1998-03-13 | 2001-06-05 | Merck Frosst Canada & Co. | Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment |
| WO1999065881A1 (en) | 1998-06-19 | 1999-12-23 | Nissan Chemical Industries, Ltd. | Heterocyclic compounds as hypoglycemic agents |
| AUPP609198A0 (en) | 1998-09-22 | 1998-10-15 | Curtin University Of Technology | Use of non-peptidyl compounds for the treatment of insulin related ailments |
| EP1177176B1 (en) | 1999-04-28 | 2006-04-19 | Aventis Pharma Deutschland GmbH | Tri-aryl acid derivatives as ppar receptor ligands |
| NZ515086A (en) | 1999-04-28 | 2003-10-31 | Aventis Pharma Gmbh | Di-aryl acid derivatives as PPAR receptor ligands |
| DE60005973T2 (de) * | 1999-08-27 | 2004-05-13 | Eli Lilly And Co., Indianapolis | Biaryl-oxa(thia)zolderivate und ihre verwendung als ppars modulatoren |
| US6787552B2 (en) * | 2000-08-11 | 2004-09-07 | Nippon Chemiphar Co., Ltd. | PPAR delta activators |
| US6875780B2 (en) * | 2002-04-05 | 2005-04-05 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods for their preparation |
| AU2003299790A1 (en) | 2002-12-20 | 2004-07-22 | Bayer Pharmaceuticals Corporation | Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation |
| CN1897939A (zh) * | 2003-10-31 | 2007-01-17 | 詹森药业有限公司 | 适用作过氧化物酶体增生物激活受体（ppar）双重激动剂的苯氧基乙酸衍生物 |
-
2004
- 2004-10-28 CN CNA2004800382161A patent/CN1897939A/zh active Pending
- 2004-10-28 ES ES04796767T patent/ES2287786T3/es not_active Expired - Lifetime
- 2004-10-28 EP EP04796767A patent/EP1684752B1/en not_active Expired - Lifetime
- 2004-10-28 KR KR1020067010610A patent/KR20060109925A/ko not_active Withdrawn
- 2004-10-28 US US10/975,785 patent/US7015329B2/en not_active Expired - Fee Related
- 2004-10-28 DE DE602004006529T patent/DE602004006529T2/de not_active Expired - Fee Related
- 2004-10-28 WO PCT/US2004/036028 patent/WO2005041959A1/en not_active Ceased
- 2004-10-28 AU AU2004285530A patent/AU2004285530A1/en not_active Abandoned
- 2004-10-28 JP JP2006538316A patent/JP2007527416A/ja not_active Withdrawn
- 2004-10-28 EA EA200600878A patent/EA009804B1/ru not_active IP Right Cessation
- 2004-10-28 AT AT04796767T patent/ATE362367T1/de not_active IP Right Cessation
- 2004-10-28 UA UAA200605139A patent/UA84035C2/ru unknown
- 2004-10-28 CA CA002544317A patent/CA2544317A1/en not_active Abandoned
- 2004-10-28 BR BRPI0416106-8A patent/BRPI0416106A/pt not_active IP Right Cessation
- 2004-10-29 AR ARP040103979A patent/AR046311A1/es not_active Application Discontinuation
- 2004-10-29 TW TW093132849A patent/TW200528438A/zh unknown
-
2005
- 2005-11-15 US US11/274,656 patent/US7498351B2/en not_active Expired - Fee Related
-
2006
- 2006-04-27 IL IL175310A patent/IL175310A0/en unknown
- 2006-04-28 EC EC2006006536A patent/ECSP066536A/es unknown
- 2006-05-02 CR CR8377A patent/CR8377A/es unknown
- 2006-05-30 ZA ZA200604420A patent/ZA200604420B/en unknown
- 2006-05-31 NO NO20062511A patent/NO20062511L/no not_active Application Discontinuation
-
2009
- 2009-01-23 US US12/358,703 patent/US20090131489A1/en not_active Abandoned
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