JP2004534035A5 - - Google Patents
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- JP2004534035A5 JP2004534035A5 JP2002589475A JP2002589475A JP2004534035A5 JP 2004534035 A5 JP2004534035 A5 JP 2004534035A5 JP 2002589475 A JP2002589475 A JP 2002589475A JP 2002589475 A JP2002589475 A JP 2002589475A JP 2004534035 A5 JP2004534035 A5 JP 2004534035A5
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- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- trifluoromethyl
- acetic acid
- thio
- 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 41
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 8
- -1 perfluoro Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- OGIHVIPVTSNHSP-UHFFFAOYSA-N 2-[4-[[2-(benzylsulfanylmethyl)-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(OC(=C2)C=2C=CC(=CC=2)C(F)(F)F)CSCC=2C=CC=CC=2)=C1 OGIHVIPVTSNHSP-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- GRRWANPLQMUWDL-UHFFFAOYSA-N 2-[4-[[5-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(OC(=C2)C=2C=CC(Cl)=CC=2)C(F)(F)F)=C1 GRRWANPLQMUWDL-UHFFFAOYSA-N 0.000 claims 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- SFNNLGOPNQUXCV-UHFFFAOYSA-N 2-[2-ethyl-4-[[2-methyl-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCC2=C(OC(=C2)C=2C=CC(=CC=2)C(F)(F)F)C)=C1 SFNNLGOPNQUXCV-UHFFFAOYSA-N 0.000 claims 2
- IFGWJUVVQJCSBR-UHFFFAOYSA-N 2-[2-methyl-4-[2-[2-methyl-5-[4-(trifluoromethyl)phenyl]furan-3-yl]ethyl]phenoxy]acetic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CCC1=CC=C(OCC(O)=O)C(C)=C1 IFGWJUVVQJCSBR-UHFFFAOYSA-N 0.000 claims 2
- APSHKIJUEPDIOL-UHFFFAOYSA-N 2-[2-methyl-4-[2-[3-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]ethyl]phenoxy]acetic acid Chemical compound CC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CCC1=CC=C(OCC(O)=O)C(C)=C1 APSHKIJUEPDIOL-UHFFFAOYSA-N 0.000 claims 2
- GAMPIJLBSSQQJO-UHFFFAOYSA-N 2-[2-methyl-4-[2-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]phenoxy]acetic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CCC1=CC=C(OCC(O)=O)C(C)=C1 GAMPIJLBSSQQJO-UHFFFAOYSA-N 0.000 claims 2
- BXAAPBCAAXFNBT-UHFFFAOYSA-N 2-[2-methyl-4-[[2-(3-methylbutyl)-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC(C)CCC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 BXAAPBCAAXFNBT-UHFFFAOYSA-N 0.000 claims 2
- PLPKWTIJWDCGJS-UHFFFAOYSA-N 2-[2-methyl-4-[[2-(propan-2-ylsulfanylmethyl)-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC(C)SCC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 PLPKWTIJWDCGJS-UHFFFAOYSA-N 0.000 claims 2
- ACFOOAHSONTJOH-UHFFFAOYSA-N 2-[2-methyl-4-[[2-(trifluoromethyl)-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(OC(=C2)C=2C=CC(=CC=2)C(F)(F)F)C(F)(F)F)=C1 ACFOOAHSONTJOH-UHFFFAOYSA-N 0.000 claims 2
- LXNJDHJMSCSYMK-UHFFFAOYSA-N 2-[2-methyl-4-[[2-[(n-methylanilino)methyl]-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C=1C=CC=CC=1N(C)CC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 LXNJDHJMSCSYMK-UHFFFAOYSA-N 0.000 claims 2
- YQGCQTMMVIIVLC-UHFFFAOYSA-N 2-[2-methyl-4-[[2-methyl-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 YQGCQTMMVIIVLC-UHFFFAOYSA-N 0.000 claims 2
- NJAUWCZVYRTXBK-UHFFFAOYSA-N 2-[2-methyl-4-[[2-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl]methoxy]phenoxy]acetic acid Chemical compound CC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1COC1=CC=C(OCC(O)=O)C(C)=C1 NJAUWCZVYRTXBK-UHFFFAOYSA-N 0.000 claims 2
- ITRQPZTWQRRMLO-UHFFFAOYSA-N 2-[2-methyl-4-[[2-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC=1SC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 ITRQPZTWQRRMLO-UHFFFAOYSA-N 0.000 claims 2
- RWIGMUATWNDKOG-UHFFFAOYSA-N 2-[2-methyl-4-[[3-(phenoxymethyl)-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(C=C(S2)C=2C=CC(=CC=2)C(F)(F)F)COC=2C=CC=CC=2)=C1 RWIGMUATWNDKOG-UHFFFAOYSA-N 0.000 claims 2
- QZMBSSNIFPSIFA-UHFFFAOYSA-N 2-[2-methyl-4-[[3-methyl-4-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound S1C=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=C1CSC1=CC=C(OCC(O)=O)C(C)=C1 QZMBSSNIFPSIFA-UHFFFAOYSA-N 0.000 claims 2
- RYDLVQHROFTVOM-UHFFFAOYSA-N 2-[2-methyl-4-[[3-methyl-5-[4-(trifluoromethoxy)phenyl]thiophen-2-yl]methoxy]phenoxy]acetic acid Chemical compound CC=1C=C(C=2C=CC(OC(F)(F)F)=CC=2)SC=1COC1=CC=C(OCC(O)=O)C(C)=C1 RYDLVQHROFTVOM-UHFFFAOYSA-N 0.000 claims 2
- QWZDPYZVCBHSEZ-UHFFFAOYSA-N 2-[2-methyl-4-[[3-methyl-5-[4-(trifluoromethyl)phenyl]furan-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)OC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 QWZDPYZVCBHSEZ-UHFFFAOYSA-N 0.000 claims 2
- YOCZJLKEOZCIGA-UHFFFAOYSA-N 2-[2-methyl-4-[[3-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methoxy]phenoxy]acetic acid Chemical compound CC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC1=CC=C(OCC(O)=O)C(C)=C1 YOCZJLKEOZCIGA-UHFFFAOYSA-N 0.000 claims 2
- RCYQDTIQCZUMKJ-UHFFFAOYSA-N 2-[2-methyl-4-[[3-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 RCYQDTIQCZUMKJ-UHFFFAOYSA-N 0.000 claims 2
- ZOFQTJMODLMZPP-UHFFFAOYSA-N 2-[4-[2-[5-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-yl]ethyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(CCC2=C(OC(=C2)C=2C=CC(Cl)=CC=2)C(F)(F)F)=C1 ZOFQTJMODLMZPP-UHFFFAOYSA-N 0.000 claims 2
- MTRUSCUYORMMOS-UHFFFAOYSA-N 2-[4-[[2-methyl-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]-2-propan-2-ylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C(C)C)=CC(SCC2=C(OC(=C2)C=2C=CC(=CC=2)C(F)(F)F)C)=C1 MTRUSCUYORMMOS-UHFFFAOYSA-N 0.000 claims 2
- TVIYUKWTXNGZIY-UHFFFAOYSA-N 2-[4-[[3-ethyl-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound CCC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 TVIYUKWTXNGZIY-UHFFFAOYSA-N 0.000 claims 2
- PUWXDYPTEZFQDT-UHFFFAOYSA-N 2-[4-[[5-(4-chlorophenyl)-2-methylfuran-3-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound CC=1OC(C=2C=CC(Cl)=CC=2)=CC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 PUWXDYPTEZFQDT-UHFFFAOYSA-N 0.000 claims 2
- NYKCZJCAVYIWAV-UHFFFAOYSA-N 3-[2-methyl-4-[2-[3-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]ethyl]phenyl]propanoic acid Chemical compound CC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CCC1=CC=C(CCC(O)=O)C(C)=C1 NYKCZJCAVYIWAV-UHFFFAOYSA-N 0.000 claims 2
- ZYNQSBLIFRMDLD-UHFFFAOYSA-N 3-[2-methyl-4-[[3-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methoxy]phenyl]propanoic acid Chemical compound CC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC1=CC=C(CCC(O)=O)C(C)=C1 ZYNQSBLIFRMDLD-UHFFFAOYSA-N 0.000 claims 2
- JSNSIMSPRLOPEO-UHFFFAOYSA-N 3-[4-[[3-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methoxy]phenyl]propanoic acid Chemical compound CC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC1=CC=C(CCC(O)=O)C=C1 JSNSIMSPRLOPEO-UHFFFAOYSA-N 0.000 claims 2
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 2
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims 2
- 125000005275 alkylenearyl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- BBLUXMGQSDRGJA-UHFFFAOYSA-N 2-[2-methyl-4-[1-[3-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]ethoxy]phenoxy]acetic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=CC(C)=C1C(C)OC1=CC=C(OCC(O)=O)C(C)=C1 BBLUXMGQSDRGJA-UHFFFAOYSA-N 0.000 claims 1
- CBEIZYSKUHRBSX-UHFFFAOYSA-N 2-[2-methyl-4-[1-[5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]ethoxy]phenoxy]acetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(C)OC1=CC=C(OCC(O)=O)C(C)=C1 CBEIZYSKUHRBSX-UHFFFAOYSA-N 0.000 claims 1
- HLCJTTRMBMZTSS-UHFFFAOYSA-N 2-[2-methyl-4-[1-[5-[4-(trifluoromethyl)phenyl]thiophen-3-yl]ethoxy]phenoxy]acetic acid Chemical compound C=1SC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1C(C)OC1=CC=C(OCC(O)=O)C(C)=C1 HLCJTTRMBMZTSS-UHFFFAOYSA-N 0.000 claims 1
- MYKMFVMSLQQNGT-UHFFFAOYSA-N 2-[2-methyl-4-[[2-(2-methylpropyl)-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC(C)CC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 MYKMFVMSLQQNGT-UHFFFAOYSA-N 0.000 claims 1
- UHWSZKUHVZTHMD-UHFFFAOYSA-N 2-[2-methyl-4-[[2-(2-pyridin-4-ylethyl)-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.C1=C(OCC(O)=O)C(C)=CC(SCC2=C(OC(=C2)C=2C=CC(=CC=2)C(F)(F)F)CCC=2C=CN=CC=2)=C1 UHWSZKUHVZTHMD-UHFFFAOYSA-N 0.000 claims 1
- AIRWCGGTUHPHNS-UHFFFAOYSA-N 2-[2-methyl-4-[[2-(phenoxymethyl)-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(OC(=C2)C=2C=CC(=CC=2)C(F)(F)F)COC=2C=CC=CC=2)=C1 AIRWCGGTUHPHNS-UHFFFAOYSA-N 0.000 claims 1
- YJFZVLMAJHJFJC-UHFFFAOYSA-N 2-[2-methyl-4-[[2-(trifluoromethyl)-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methoxy]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(OCC2=C(OC(=C2)C=2C=CC(=CC=2)C(F)(F)F)C(F)(F)F)=C1 YJFZVLMAJHJFJC-UHFFFAOYSA-N 0.000 claims 1
- SDXYXAXTXVTKBP-UHFFFAOYSA-N 2-[2-methyl-4-[[2-[2-(4-methylphenyl)ethyl]-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=CC(C)=CC=C1CCC1=C(CSC=2C=C(C)C(OCC(O)=O)=CC=2)C=C(C=2C=CC(=CC=2)C(F)(F)F)O1 SDXYXAXTXVTKBP-UHFFFAOYSA-N 0.000 claims 1
- BRTCHXMHYSMHJJ-UHFFFAOYSA-N 2-[2-methyl-4-[[2-[[methyl(2-phenylethyl)amino]methyl]-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.O1C(C=2C=CC(=CC=2)C(F)(F)F)=CC(CSC=2C=C(C)C(OCC(O)=O)=CC=2)=C1CN(C)CCC1=CC=CC=C1 BRTCHXMHYSMHJJ-UHFFFAOYSA-N 0.000 claims 1
- GIVRDNCABIOBRR-UHFFFAOYSA-N 2-[2-methyl-4-[[2-methyl-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methoxy]phenoxy]acetic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1COC1=CC=C(OCC(O)=O)C(C)=C1 GIVRDNCABIOBRR-UHFFFAOYSA-N 0.000 claims 1
- RBQLTRZGQRMWFQ-UHFFFAOYSA-N 2-[2-methyl-4-[[3-(propan-2-ylsulfanylmethyl)-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methoxy]phenoxy]acetic acid Chemical compound CC(C)SCC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC1=CC=C(OCC(O)=O)C(C)=C1 RBQLTRZGQRMWFQ-UHFFFAOYSA-N 0.000 claims 1
- LCLKBXKOLVIZQR-UHFFFAOYSA-N 2-[2-methyl-4-[[3-(propan-2-ylsulfanylmethyl)-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC(C)SCC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 LCLKBXKOLVIZQR-UHFFFAOYSA-N 0.000 claims 1
- WTFZAJWHDSOBLE-UHFFFAOYSA-N 2-[2-methyl-4-[[3-[(n-methylanilino)methyl]-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C=1C=CC=CC=1N(C)CC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 WTFZAJWHDSOBLE-UHFFFAOYSA-N 0.000 claims 1
- AZHPTSALPMQRGW-UHFFFAOYSA-N 2-[2-methyl-4-[[3-[[4-(trifluoromethyl)phenoxy]methyl]-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(C=C(S2)C=2C=CC(=CC=2)C(F)(F)F)COC=2C=CC(=CC=2)C(F)(F)F)=C1 AZHPTSALPMQRGW-UHFFFAOYSA-N 0.000 claims 1
- RZAFHMYSLNFMNQ-UHFFFAOYSA-N 2-[2-methyl-4-[[3-methyl-5-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]thiophen-2-yl]methoxy]phenoxy]acetic acid Chemical compound CC=1C=C(C=2C=CC(OC(F)(F)C(F)F)=CC=2)SC=1COC1=CC=C(OCC(O)=O)C(C)=C1 RZAFHMYSLNFMNQ-UHFFFAOYSA-N 0.000 claims 1
- UPWRVBXHFNSFQT-UHFFFAOYSA-N 2-[2-methyl-4-[[3-methyl-5-[4-(trifluoromethoxy)phenyl]thiophen-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC=1C=C(C=2C=CC(OC(F)(F)F)=CC=2)SC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 UPWRVBXHFNSFQT-UHFFFAOYSA-N 0.000 claims 1
- UUQKPRXFMLMBMG-UHFFFAOYSA-N 2-[2-methyl-4-[[3-methyl-5-[4-(trifluoromethyl)phenyl]furan-2-yl]methoxy]phenoxy]acetic acid Chemical compound CC=1C=C(C=2C=CC(=CC=2)C(F)(F)F)OC=1COC1=CC=C(OCC(O)=O)C(C)=C1 UUQKPRXFMLMBMG-UHFFFAOYSA-N 0.000 claims 1
- MCAMNELDXNLQFK-UHFFFAOYSA-N 2-[2-methyl-4-[[5-[4-(trifluoromethyl)phenyl]furan-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2OC(=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 MCAMNELDXNLQFK-UHFFFAOYSA-N 0.000 claims 1
- YMFYVQVRPWQAIC-UHFFFAOYSA-N 2-[2-methyl-4-[[5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2C=C(OC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 YMFYVQVRPWQAIC-UHFFFAOYSA-N 0.000 claims 1
- XEUGLMGFMXQQRN-UHFFFAOYSA-N 2-[2-methyl-4-[[5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2SC(=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 XEUGLMGFMXQQRN-UHFFFAOYSA-N 0.000 claims 1
- IYMWINVCTXDNAV-UHFFFAOYSA-N 2-[2-methyl-4-[[5-[4-(trifluoromethyl)phenyl]thiophen-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2C=C(SC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 IYMWINVCTXDNAV-UHFFFAOYSA-N 0.000 claims 1
- PHIRDEHXYOMRQH-UHFFFAOYSA-N 2-[4-[[2-(furan-2-ylmethylsulfanylmethyl)-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(OC(=C2)C=2C=CC(=CC=2)C(F)(F)F)CSCC=2OC=CC=2)=C1 PHIRDEHXYOMRQH-UHFFFAOYSA-N 0.000 claims 1
- ODFQQKIPPLXPMJ-UHFFFAOYSA-N 2-[4-[[2-[(2,4-difluorophenyl)sulfanylmethyl]-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(OC(=C2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C(=CC(F)=CC=2)F)=C1 ODFQQKIPPLXPMJ-UHFFFAOYSA-N 0.000 claims 1
- SXOWQVCVAJUPMS-UHFFFAOYSA-N 2-[4-[[2-[(3,5-dimethylphenyl)sulfanylmethyl]-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound CC1=CC(C)=CC(SCC2=C(C=C(O2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=C(C)C(OCC(O)=O)=CC=2)=C1 SXOWQVCVAJUPMS-UHFFFAOYSA-N 0.000 claims 1
- IDTGXFJFUKLFEN-UHFFFAOYSA-N 2-[4-[[2-[(4-tert-butylphenyl)sulfanylmethyl]-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(OC(=C2)C=2C=CC(=CC=2)C(F)(F)F)CSC=2C=CC(=CC=2)C(C)(C)C)=C1 IDTGXFJFUKLFEN-UHFFFAOYSA-N 0.000 claims 1
- YFSYOPQVNBHVBU-UHFFFAOYSA-N 2-[4-[[2-methyl-5-[4-(trifluoromethyl)phenyl]furan-3-yl]methylsulfanyl]-2-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CSC1=CC=C(OCC(O)=O)C(C(F)(F)F)=C1 YFSYOPQVNBHVBU-UHFFFAOYSA-N 0.000 claims 1
- QOYYFIVYYRAKLC-UHFFFAOYSA-N 2-[4-[[3-(benzylsulfanylmethyl)-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl]methylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=C(C=C(S2)C=2C=CC(=CC=2)C(F)(F)F)CSCC=2C=CC=CC=2)=C1 QOYYFIVYYRAKLC-UHFFFAOYSA-N 0.000 claims 1
- CBSFAEQCEQSAHC-UHFFFAOYSA-N 2-[4-[[5-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-yl]methoxy]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(OCC2=C(OC(=C2)C=2C=CC(Cl)=CC=2)C(F)(F)F)=C1 CBSFAEQCEQSAHC-UHFFFAOYSA-N 0.000 claims 1
- SZIQXEQVPOYRNY-UHFFFAOYSA-N 2-[4-[[5-(4-chlorophenyl)-2-methylfuran-3-yl]methoxy]-2-methylphenoxy]acetic acid Chemical compound CC=1OC(C=2C=CC(Cl)=CC=2)=CC=1COC1=CC=C(OCC(O)=O)C(C)=C1 SZIQXEQVPOYRNY-UHFFFAOYSA-N 0.000 claims 1
- UYDAXIJQZDVGMK-UHFFFAOYSA-N 2-[4-[[5-(4-chlorophenyl)-2-methylfuran-3-yl]methylsulfanyl]-2-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC=1OC(C=2C=CC(Cl)=CC=2)=CC=1CSC1=CC=C(OCC(O)=O)C(C(F)(F)F)=C1 UYDAXIJQZDVGMK-UHFFFAOYSA-N 0.000 claims 1
- XHPVYJHZQFIHLT-UHFFFAOYSA-N 2-[4-[[5-[2,3-difluoro-4-(trifluoromethyl)phenyl]-3-methylthiophen-2-yl]methoxy]-2-methylphenoxy]acetic acid Chemical compound CC=1C=C(C=2C(=C(F)C(=CC=2)C(F)(F)F)F)SC=1COC1=CC=C(OCC(O)=O)C(C)=C1 XHPVYJHZQFIHLT-UHFFFAOYSA-N 0.000 claims 1
- OIILLEZAFONCDR-UHFFFAOYSA-N 2-[4-[[5-[2,5-difluoro-4-(trifluoromethyl)phenyl]-3-methylthiophen-2-yl]methoxy]-2-methylphenoxy]acetic acid Chemical compound CC=1C=C(C=2C(=CC(=C(F)C=2)C(F)(F)F)F)SC=1COC1=CC=C(OCC(O)=O)C(C)=C1 OIILLEZAFONCDR-UHFFFAOYSA-N 0.000 claims 1
- NCBKIYWMBUIWNA-UHFFFAOYSA-N 2-[4-[[5-[2-fluoro-4-(trifluoromethyl)phenyl]-3-methylthiophen-2-yl]methoxy]-2-methylphenoxy]acetic acid Chemical compound CC=1C=C(C=2C(=CC(=CC=2)C(F)(F)F)F)SC=1COC1=CC=C(OCC(O)=O)C(C)=C1 NCBKIYWMBUIWNA-UHFFFAOYSA-N 0.000 claims 1
- XHFHPHCRPUUCBS-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[phenyl-[5-[4-(trifluoromethyl)phenyl]thiophen-3-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OC(C=2C=C(SC=2)C=2C=CC(=CC=2)C(F)(F)F)C=2C=CC=CC=2)=C1 XHFHPHCRPUUCBS-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- FFMJLHDVACASSI-UHFFFAOYSA-N 3-[2-methyl-4-[2-[2-methyl-5-[4-(trifluoromethyl)phenyl]furan-3-yl]ethyl]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CCC1=CC=C(CCC(O)=O)C(C)=C1 FFMJLHDVACASSI-UHFFFAOYSA-N 0.000 claims 1
- HFRYZGKPKOQJPS-UHFFFAOYSA-N 3-[4-[[5-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-yl]methoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OCC2=C(OC(=C2)C=2C=CC(Cl)=CC=2)C(F)(F)F)=C1 HFRYZGKPKOQJPS-UHFFFAOYSA-N 0.000 claims 1
- NRGRJXGBBXXZOU-UHFFFAOYSA-N 3-[4-[[5-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-yl]methoxy]phenyl]propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1OCC1=C(C(F)(F)F)OC(C=2C=CC(Cl)=CC=2)=C1 NRGRJXGBBXXZOU-UHFFFAOYSA-N 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- SPBGXUAHMQXDRP-UHFFFAOYSA-N C=1C=CN=CC=1CN(C)CC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 Chemical compound C=1C=CN=CC=1CN(C)CC=1OC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1CSC1=CC=C(OCC(O)=O)C(C)=C1 SPBGXUAHMQXDRP-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010020710 Hyperphagia Diseases 0.000 claims 1
- 102000004877 Insulin Human genes 0.000 claims 1
- 108090001061 Insulin Proteins 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229940125396 insulin Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 235000020830 overeating Nutrition 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
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| PCT/GB2002/002152 WO2002092590A1 (en) | 2001-05-11 | 2002-05-09 | Furan and thiophene derivatives that activate human peroxisome proliferator activated receptors |
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Families Citing this family (41)
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| US7041691B1 (en) | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| US20030171399A1 (en) | 2000-06-28 | 2003-09-11 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| US7105551B2 (en) * | 2000-12-20 | 2006-09-12 | Smithkline Beecham Corporation | Thiazole derivatives for treating PPAR related disorders |
| GB0113232D0 (en) * | 2001-05-31 | 2001-07-25 | Glaxo Group Ltd | Chemical process |
| IL160304A0 (en) | 2001-08-10 | 2004-07-25 | Nippon Chemiphar Co | ACTIVATOR FOR PEROXISOME PROLIFERATOR-RESPONSIVE RECEPTOR delta |
| ITRM20020014A1 (it) * | 2002-01-15 | 2003-07-15 | Sigma Tau Ind Farmaceuti | Derivati di acidi a-feniltiocarbossilici e a-fenilossicarbossilici utili per il trattamento di patologie che rispondono all'attivazione del |
| US20030207924A1 (en) * | 2002-03-07 | 2003-11-06 | Xue-Min Cheng | Compounds that modulate PPAR activity and methods of preparation |
| US6833380B2 (en) | 2002-03-07 | 2004-12-21 | Warner-Lambert Company, Llc | Compounds that modulate PPAR activity and methods of preparation |
| US6875780B2 (en) | 2002-04-05 | 2005-04-05 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods for their preparation |
| JP2005035966A (ja) * | 2002-09-06 | 2005-02-10 | Takeda Chem Ind Ltd | フランまたはチオフェン誘導体およびその医薬用途 |
| WO2004022551A1 (ja) * | 2002-09-06 | 2004-03-18 | Takeda Pharmaceutical Company Limited | フランまたはチオフェン誘導体およびその医薬用途 |
| AU2003277576A1 (en) * | 2002-11-08 | 2004-06-07 | Takeda Pharmaceutical Company Limited | Receptor function controlling agent |
| US7504433B2 (en) | 2003-01-06 | 2009-03-17 | Eli Lilly And Company | Thiophene derivative PPAR modulators |
| US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| EP1493739A1 (fr) * | 2003-07-03 | 2005-01-05 | Warner-Lambert Company LLC | Dérivés thiophényliques d'aminoacides, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
| US7223761B2 (en) | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| BRPI0416283A (pt) | 2003-11-05 | 2007-01-23 | Hoffmann La Roche | compostos, processo para a fabricação de compostos, composição farmacêutica, método para o tratamento e/ou prevenção de doenças que são moduladas por agonistas de ppar(delta) e/ou ppar(alfa) e uso destes compostos |
| AU2004309271A1 (en) | 2003-12-25 | 2005-07-14 | Takeda Pharmaceutical Company Limited | 3-(4-benzyloxyphenyl)propanoic acid derivatives |
| US7585880B2 (en) | 2003-12-26 | 2009-09-08 | Takeda Pharmaceutical Company Limited | Phenylpropanoic acid derivatives |
| GB0403148D0 (en) * | 2004-02-12 | 2004-03-17 | Smithkline Beecham Corp | Chemical compounds |
| DE602004004631D1 (de) | 2004-04-01 | 2007-03-22 | Sanofi Aventis Deutschland | Oxadiazolone, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pharmazeutika |
| JPWO2006090920A1 (ja) * | 2005-02-28 | 2008-07-24 | 日本ケミファ株式会社 | ペルオキシソーム増殖剤活性化受容体δの活性化剤 |
| CN101193876B (zh) * | 2005-05-07 | 2011-05-11 | 财团法人首尔大学校产学协力财团 | 制备PPARδ的配体的方法和用于制备该配体的中间化合物 |
| CA2609446A1 (en) * | 2005-05-25 | 2006-11-30 | Nippon Chemiphar Co., Ltd. | Activator for peroxisome proliferator-activated receptor |
| JP2009509988A (ja) | 2005-09-29 | 2009-03-12 | サノフィ−アベンティス | フェニル−及びピリジニル−１，２，４−オキサジアゾロン誘導体、その製造方法、及び医薬品としてのその使用 |
| PT1931660E (pt) | 2005-09-29 | 2012-10-30 | Sanofi Sa | Derivados de fenil-[1,2,4]-oxadiazol-5-ona com grupo fenilo, processos para a sua preparação e sua utilização como fármacos |
| EP2044042A2 (en) * | 2006-01-10 | 2009-04-08 | SmithKline Beecham Corporation | Polymorphic forms of { 2-methyl-4- [4-methyl-2- (trifluoromethylphenyl) thiazol-5-methylthiol phenoxy}-acetic acid |
| NZ572268A (en) | 2006-04-18 | 2011-09-30 | Nippon Chemiphar Co | Activating agent for peroxisome proliferator activated receptor delta (ppar) |
| NZ574905A (en) * | 2006-08-22 | 2011-12-22 | Ranbaxy Lab Ltd | Matrix metalloproteinase inhibitors |
| JP2010514804A (ja) | 2006-12-29 | 2010-05-06 | ザ・ソーク・インスティチュート・フォー・バイオロジカル・スタディーズ | 運動能力を高めるための方法 |
| FR2910894A1 (fr) * | 2006-12-29 | 2008-07-04 | Genfit Sa | Derives de 3-phenyl-1-(phenylthienyl)propan-1-one et de 3-phenyl-1-(phenylfuranyl)propan-1-one substitues, preparation et utilisation. |
| WO2008103574A2 (en) * | 2007-02-23 | 2008-08-28 | Eli Lilly And Company | Peroxisome proliferator activated receptor modulators |
| KR20080082541A (ko) * | 2007-03-07 | 2008-09-11 | 동아제약주식회사 | 퍼옥시좀 증식자-활성화 감마 수용체를 조절하는 신규한페닐프로판산 유도체의 제조방법 및 약학적 용도 |
| DE102008007400A1 (de) * | 2008-02-04 | 2009-08-06 | Bayer Healthcare Ag | Substituierte Furane und ihre Verwendung |
| BRPI0911197A2 (pt) | 2008-04-15 | 2015-10-13 | Nippon Chemiphar Co | composto, ativador de receptor ativado pelo proliferador de peroxissoma, e, medicamento para o tratamento e /ou profilaxia de uma doença. |
| CN101643451B (zh) * | 2008-08-07 | 2013-03-06 | 浙江海正药业股份有限公司 | 过氧化物酶增殖物激活受体亚型δ类激动剂化合物及其制备方法 |
| WO2012030165A2 (ko) | 2010-08-31 | 2012-03-08 | 서울대학교산학협력단 | P P A R δ 활성물질의 태자재프로그래밍용도 |
| WO2014159054A1 (en) * | 2013-03-14 | 2014-10-02 | Janssen Pharmaceutica Nv | Gpr120 agonists for the treatment of type ii diabetes |
| BR112015021757B8 (pt) * | 2013-03-14 | 2022-08-23 | Dow Agrosciences Llc | Molécula apresentando certas utilidades pesticidas, e processo |
| US11634387B2 (en) | 2019-09-26 | 2023-04-25 | Abionyx Pharma Sa | Compounds useful for treating liver diseases |
| WO2022189856A1 (en) * | 2021-03-08 | 2022-09-15 | Abionyx Pharma Sa | Compounds useful for treating liver diseases |
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|---|---|---|---|---|
| GB9817118D0 (en) | 1998-08-07 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| EP1177187B1 (en) * | 1999-04-28 | 2007-07-25 | Sanofi-Aventis Deutschland GmbH | Di-aryl acid derivatives as ppar receptor ligands |
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2001
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2002
- 2002-05-09 EP EP02722506A patent/EP1392674B1/en not_active Expired - Lifetime
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- 2002-05-09 DE DE60205481T patent/DE60205481T2/de not_active Expired - Fee Related
- 2002-05-09 CZ CZ20033064A patent/CZ20033064A3/cs unknown
- 2002-05-09 US US10/476,194 patent/US7091237B2/en not_active Expired - Fee Related
- 2002-05-09 CN CNA028096940A patent/CN1507442A/zh active Pending
- 2002-05-09 BR BR0209468-1A patent/BR0209468A/pt not_active IP Right Cessation
- 2002-05-09 KR KR10-2003-7014660A patent/KR20040023600A/ko not_active Withdrawn
- 2002-05-09 JP JP2002589475A patent/JP2004534035A/ja active Pending
- 2002-05-09 PL PL02367478A patent/PL367478A1/xx not_active Application Discontinuation
- 2002-05-09 WO PCT/GB2002/002152 patent/WO2002092590A1/en not_active Ceased
- 2002-05-09 AT AT02722506T patent/ATE301649T1/de not_active IP Right Cessation
- 2002-05-09 ES ES02722506T patent/ES2247322T3/es not_active Expired - Lifetime
- 2002-05-09 HU HU0304051A patent/HUP0304051A3/hu unknown
- 2002-05-09 IL IL15833202A patent/IL158332A0/xx unknown
- 2002-05-09 CA CA002446797A patent/CA2446797A1/en not_active Abandoned
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2003
- 2003-10-27 ZA ZA200308352A patent/ZA200308352B/en unknown
- 2003-11-10 NO NO20034986A patent/NO20034986D0/no not_active Application Discontinuation
- 2003-11-10 CO CO03099078A patent/CO5540343A2/es not_active Application Discontinuation
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