JP2007501288A5 - - Google Patents
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- JP2007501288A5 JP2007501288A5 JP2006536536A JP2006536536A JP2007501288A5 JP 2007501288 A5 JP2007501288 A5 JP 2007501288A5 JP 2006536536 A JP2006536536 A JP 2006536536A JP 2006536536 A JP2006536536 A JP 2006536536A JP 2007501288 A5 JP2007501288 A5 JP 2007501288A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- salt
- dione
- phenoxy
- methoxycarbonylethyl
- 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.)
- Granted
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- 150000003839 salts Chemical class 0.000 claims 168
- 150000001875 compounds Chemical class 0.000 claims 41
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 239000011593 sulfur Substances 0.000 claims 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 12
- -1 cyano, formyl Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 239000001301 oxygen Substances 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 10
- 235000001014 amino acid Nutrition 0.000 claims 9
- 229940024606 amino acid Drugs 0.000 claims 9
- 150000001413 amino acids Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 239000000543 intermediate Substances 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 230000000269 nucleophilic effect Effects 0.000 claims 2
- COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical compound O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 1
- IEAGYIIYKUNMJQ-UHFFFAOYSA-N 2-amino-3-[2-amino-4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]phenyl]propanoic acid Chemical compound C1=C(N)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 IEAGYIIYKUNMJQ-UHFFFAOYSA-N 0.000 claims 1
- SEWGFPXFVMMKEI-UHFFFAOYSA-N 2-amino-3-[2-amino-4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoic acid Chemical compound C1=C(N)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 SEWGFPXFVMMKEI-UHFFFAOYSA-N 0.000 claims 1
- XUBIOWXXEXLHEO-UHFFFAOYSA-N 2-amino-3-[2-amino-4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]propanoic acid Chemical compound C1=C(N)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 XUBIOWXXEXLHEO-UHFFFAOYSA-N 0.000 claims 1
- KEJQAEUDZFJOEE-UHFFFAOYSA-N 2-amino-3-[2-amino-4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoic acid Chemical compound C1=C(N)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 KEJQAEUDZFJOEE-UHFFFAOYSA-N 0.000 claims 1
- DNCFFWWPBHXGLE-UHFFFAOYSA-N 2-amino-3-[4-[2-amino-4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1)N)=CC=C1CC1C(=O)NC(=O)O1 DNCFFWWPBHXGLE-UHFFFAOYSA-N 0.000 claims 1
- GYZRAZRLRVJVFG-UHFFFAOYSA-N 2-amino-3-[4-[2-amino-4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1)N)=CC=C1C=C1C(=O)NC(=O)O1 GYZRAZRLRVJVFG-UHFFFAOYSA-N 0.000 claims 1
- LVSLBYSKKZGLOY-UHFFFAOYSA-N 2-amino-3-[4-[2-amino-4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1)N)=CC=C1CC1C(=O)NC(=O)S1 LVSLBYSKKZGLOY-UHFFFAOYSA-N 0.000 claims 1
- STJMJLNDWIFIQK-UHFFFAOYSA-N 2-amino-3-[4-[2-amino-4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1)N)=CC=C1C=C1C(=O)NC(=O)S1 STJMJLNDWIFIQK-UHFFFAOYSA-N 0.000 claims 1
- TYGUMOWIQVZSHW-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2,3-difluorophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1F)F)=CC=C1CC1C(=O)NC(=O)O1 TYGUMOWIQVZSHW-UHFFFAOYSA-N 0.000 claims 1
- DIQYSJCKUNKKIG-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1CC1C(=O)NC(=O)O1 DIQYSJCKUNKKIG-UHFFFAOYSA-N 0.000 claims 1
- LMVXXXFHMCNCKW-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-fluorophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1)F)=CC=C1CC1C(=O)NC(=O)O1 LMVXXXFHMCNCKW-UHFFFAOYSA-N 0.000 claims 1
- ZRPDMWVIJCZPBH-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-methylphenoxy]phenyl]propanoic acid Chemical compound C=1C=C(OC=2C=CC(CC(N)C(O)=O)=CC=2)C(C)=CC=1CC1OC(=O)NC1=O ZRPDMWVIJCZPBH-UHFFFAOYSA-N 0.000 claims 1
- VLMFSKUOKJCFDN-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-nitrophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1)[N+]([O-])=O)=CC=C1CC1C(=O)NC(=O)O1 VLMFSKUOKJCFDN-UHFFFAOYSA-N 0.000 claims 1
- SQMOIGUGYKOLFL-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-3,5-difluorophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1F)=CC(F)=C1CC1C(=O)NC(=O)O1 SQMOIGUGYKOLFL-UHFFFAOYSA-N 0.000 claims 1
- VQTYLKRLKRBOSC-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-3-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1C(F)(F)F)=CC=C1CC1C(=O)NC(=O)O1 VQTYLKRLKRBOSC-UHFFFAOYSA-N 0.000 claims 1
- COKASQDIFJTIPJ-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-3-fluorophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1F)=CC=C1CC1C(=O)NC(=O)O1 COKASQDIFJTIPJ-UHFFFAOYSA-N 0.000 claims 1
- FDFQQNSLHSNPIY-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2,3-difluorophenyl]propanoic acid Chemical compound FC1=C(F)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 FDFQQNSLHSNPIY-UHFFFAOYSA-N 0.000 claims 1
- NVVUWDZMINEZQB-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-(trifluoromethyl)phenyl]propanoic acid Chemical compound C1=C(C(F)(F)F)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 NVVUWDZMINEZQB-UHFFFAOYSA-N 0.000 claims 1
- QGFMLALVUBXMBI-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-fluorophenyl]propanoic acid Chemical compound C1=C(F)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 QGFMLALVUBXMBI-UHFFFAOYSA-N 0.000 claims 1
- YQTJDLBNHWNLGS-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(CC(N)C(O)=O)C(C)=CC(OC=2C=CC(CC3C(NC(=O)O3)=O)=CC=2)=C1 YQTJDLBNHWNLGS-UHFFFAOYSA-N 0.000 claims 1
- KXYQJQLFJFOCTB-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-nitrophenyl]propanoic acid Chemical compound C1=C([N+]([O-])=O)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 KXYQJQLFJFOCTB-UHFFFAOYSA-N 0.000 claims 1
- XPPLRZCCIPXNDA-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-3,5-difluorophenyl]propanoic acid Chemical compound FC1=CC(CC(N)C(O)=O)=CC(F)=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 XPPLRZCCIPXNDA-UHFFFAOYSA-N 0.000 claims 1
- UMVUKMXAGFOOJS-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-3-(trifluoromethyl)phenyl]propanoic acid Chemical compound FC(F)(F)C1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 UMVUKMXAGFOOJS-UHFFFAOYSA-N 0.000 claims 1
- BDENRQFNAYEAPJ-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-3-fluorophenyl]propanoic acid Chemical compound FC1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 BDENRQFNAYEAPJ-UHFFFAOYSA-N 0.000 claims 1
- GYWZNBVJXWDKRK-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 GYWZNBVJXWDKRK-UHFFFAOYSA-N 0.000 claims 1
- AVUOWMAFTPQQOK-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2,3-difluorophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1F)F)=CC=C1C=C1C(=O)NC(=O)O1 AVUOWMAFTPQQOK-UHFFFAOYSA-N 0.000 claims 1
- ZLDNXHXUZHMCMY-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)O1 ZLDNXHXUZHMCMY-UHFFFAOYSA-N 0.000 claims 1
- GYTMUFHRSBCKPE-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2-fluorophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1)F)=CC=C1C=C1C(=O)NC(=O)O1 GYTMUFHRSBCKPE-UHFFFAOYSA-N 0.000 claims 1
- PJZSYFCRIHVTFG-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2-methylphenoxy]phenyl]propanoic acid Chemical compound C=1C=C(OC=2C=CC(CC(N)C(O)=O)=CC=2)C(C)=CC=1C=C1OC(=O)NC1=O PJZSYFCRIHVTFG-UHFFFAOYSA-N 0.000 claims 1
- SSEWGMLIMPKJMP-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2-nitrophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1)[N+]([O-])=O)=CC=C1C=C1C(=O)NC(=O)O1 SSEWGMLIMPKJMP-UHFFFAOYSA-N 0.000 claims 1
- YNUUBCYPJHRCPB-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-3,5-difluorophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1F)=CC(F)=C1C=C1C(=O)NC(=O)O1 YNUUBCYPJHRCPB-UHFFFAOYSA-N 0.000 claims 1
- JYYLIYMBAQWOHZ-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-3-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)O1 JYYLIYMBAQWOHZ-UHFFFAOYSA-N 0.000 claims 1
- OFGCOUNCKJLOHT-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-3-fluorophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1F)=CC=C1C=C1C(=O)NC(=O)O1 OFGCOUNCKJLOHT-UHFFFAOYSA-N 0.000 claims 1
- AZQWPPHHHRHWSZ-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2,3-difluorophenyl]propanoic acid Chemical compound FC1=C(F)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 AZQWPPHHHRHWSZ-UHFFFAOYSA-N 0.000 claims 1
- JEEIEYSQMONFKW-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-(trifluoromethyl)phenyl]propanoic acid Chemical compound C1=C(C(F)(F)F)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 JEEIEYSQMONFKW-UHFFFAOYSA-N 0.000 claims 1
- RHMBFOVZDVRNQR-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-fluorophenyl]propanoic acid Chemical compound C1=C(F)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 RHMBFOVZDVRNQR-UHFFFAOYSA-N 0.000 claims 1
- HBRDRPOCPQEDNA-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(CC(N)C(O)=O)C(C)=CC(OC=2C=CC(C=C3C(NC(=O)O3)=O)=CC=2)=C1 HBRDRPOCPQEDNA-UHFFFAOYSA-N 0.000 claims 1
- WKVDSJDRVPZBAW-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-nitrophenyl]propanoic acid Chemical compound C1=C([N+]([O-])=O)C(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 WKVDSJDRVPZBAW-UHFFFAOYSA-N 0.000 claims 1
- TWKGCJHFSSPQSO-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-3,5-difluorophenyl]propanoic acid Chemical compound FC1=CC(CC(N)C(O)=O)=CC(F)=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 TWKGCJHFSSPQSO-UHFFFAOYSA-N 0.000 claims 1
- SQJFMLMQZDCLCO-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-3-(trifluoromethyl)phenyl]propanoic acid Chemical compound FC(F)(F)C1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 SQJFMLMQZDCLCO-UHFFFAOYSA-N 0.000 claims 1
- MBVYXVIJWPACPJ-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-3-fluorophenyl]propanoic acid Chemical compound FC1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 MBVYXVIJWPACPJ-UHFFFAOYSA-N 0.000 claims 1
- OEJFIAPYBGLJHI-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 OEJFIAPYBGLJHI-UHFFFAOYSA-N 0.000 claims 1
- CJROKHCWPDOALK-UHFFFAOYSA-N 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2,3-difluorophenoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(N)C(O)=O)=CC=C1OC(C(=C1F)F)=CC=C1CC1C(=O)NC(=O)S1 CJROKHCWPDOALK-UHFFFAOYSA-N 0.000 claims 1
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- KEJMBMOGVKCCEB-UHFFFAOYSA-N methyl 2-amino-3-[2-amino-4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]phenyl]propanoate Chemical compound C1=C(N)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 KEJMBMOGVKCCEB-UHFFFAOYSA-N 0.000 claims 1
- UWAQIWSTYCXHBJ-UHFFFAOYSA-N methyl 2-amino-3-[2-amino-4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate Chemical compound C1=C(N)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 UWAQIWSTYCXHBJ-UHFFFAOYSA-N 0.000 claims 1
- WCOQWNANGBUHBJ-UHFFFAOYSA-N methyl 2-amino-3-[2-amino-4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]propanoate Chemical compound C1=C(N)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 WCOQWNANGBUHBJ-UHFFFAOYSA-N 0.000 claims 1
- FQIIXGSPXRWIMH-UHFFFAOYSA-N methyl 2-amino-3-[2-amino-4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate Chemical compound C1=C(N)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 FQIIXGSPXRWIMH-UHFFFAOYSA-N 0.000 claims 1
- VSEVDYVECLOBAX-UHFFFAOYSA-N methyl 2-amino-3-[4-[2-amino-4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)N)=CC=C1CC1C(=O)NC(=O)O1 VSEVDYVECLOBAX-UHFFFAOYSA-N 0.000 claims 1
- KFSLNLHYAVSSEU-UHFFFAOYSA-N methyl 2-amino-3-[4-[2-amino-4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)N)=CC=C1C=C1C(=O)NC(=O)O1 KFSLNLHYAVSSEU-UHFFFAOYSA-N 0.000 claims 1
- DTTSMAZTBFTAII-UHFFFAOYSA-N methyl 2-amino-3-[4-[2-amino-4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)N)=CC=C1CC1C(=O)NC(=O)S1 DTTSMAZTBFTAII-UHFFFAOYSA-N 0.000 claims 1
- NZZZCISRMPONHJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[2-amino-4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)N)=CC=C1C=C1C(=O)NC(=O)S1 NZZZCISRMPONHJ-UHFFFAOYSA-N 0.000 claims 1
- LQTXFKOPAKSRPR-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2,3-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1F)F)=CC=C1CC1C(=O)NC(=O)O1 LQTXFKOPAKSRPR-UHFFFAOYSA-N 0.000 claims 1
- MNGYHHXEAHLKIC-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1CC1C(=O)NC(=O)O1 MNGYHHXEAHLKIC-UHFFFAOYSA-N 0.000 claims 1
- LJCQEOGRMPCFTI-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)F)=CC=C1CC1C(=O)NC(=O)O1 LJCQEOGRMPCFTI-UHFFFAOYSA-N 0.000 claims 1
- CODCYMHHTBNREB-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-methylphenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C)=CC=C1CC1C(=O)NC(=O)O1 CODCYMHHTBNREB-UHFFFAOYSA-N 0.000 claims 1
- PGUVBVMVOHNTGJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-nitrophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)[N+]([O-])=O)=CC=C1CC1C(=O)NC(=O)O1 PGUVBVMVOHNTGJ-UHFFFAOYSA-N 0.000 claims 1
- XMJVDOJWDCSGAM-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-3,5-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC(F)=C1CC1C(=O)NC(=O)O1 XMJVDOJWDCSGAM-UHFFFAOYSA-N 0.000 claims 1
- TVPMPZYCRJLAFW-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-3-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1C(F)(F)F)=CC=C1CC1C(=O)NC(=O)O1 TVPMPZYCRJLAFW-UHFFFAOYSA-N 0.000 claims 1
- PLFGIUSCVHVKOS-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-3-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC=C1CC1C(=O)NC(=O)O1 PLFGIUSCVHVKOS-UHFFFAOYSA-N 0.000 claims 1
- MROIPHQFYPGLMQ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2,3-difluorophenyl]propanoate Chemical compound FC1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 MROIPHQFYPGLMQ-UHFFFAOYSA-N 0.000 claims 1
- GPQMLUWMSJGVKH-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 GPQMLUWMSJGVKH-UHFFFAOYSA-N 0.000 claims 1
- FCXZYYNRFATUSJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-fluorophenyl]propanoate Chemical compound C1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 FCXZYYNRFATUSJ-UHFFFAOYSA-N 0.000 claims 1
- WXOLLQHWOZXMKM-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 WXOLLQHWOZXMKM-UHFFFAOYSA-N 0.000 claims 1
- OMPJEKQAPFHGLL-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-nitrophenyl]propanoate Chemical compound C1=C([N+]([O-])=O)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 OMPJEKQAPFHGLL-UHFFFAOYSA-N 0.000 claims 1
- HYQIZYXZQSYDCJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-3,5-difluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC(F)=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 HYQIZYXZQSYDCJ-UHFFFAOYSA-N 0.000 claims 1
- MPFQVGALPSRHIA-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-3-(trifluoromethyl)phenyl]propanoate Chemical compound FC(F)(F)C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 MPFQVGALPSRHIA-UHFFFAOYSA-N 0.000 claims 1
- CORWUWCGIXKJFS-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-3-fluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 CORWUWCGIXKJFS-UHFFFAOYSA-N 0.000 claims 1
- OOAGJTGMKGAQOI-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 OOAGJTGMKGAQOI-UHFFFAOYSA-N 0.000 claims 1
- WQTSSWGQDUMQBL-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2,3-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1F)F)=CC=C1C=C1C(=O)NC(=O)O1 WQTSSWGQDUMQBL-UHFFFAOYSA-N 0.000 claims 1
- BAAZBUVOUCRIBR-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)O1 BAAZBUVOUCRIBR-UHFFFAOYSA-N 0.000 claims 1
- XVINYCICGTVTNH-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2-methylphenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C)=CC=C1C=C1C(=O)NC(=O)O1 XVINYCICGTVTNH-UHFFFAOYSA-N 0.000 claims 1
- GFYDLBXGLDJUNT-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2-nitrophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)[N+]([O-])=O)=CC=C1C=C1C(=O)NC(=O)O1 GFYDLBXGLDJUNT-UHFFFAOYSA-N 0.000 claims 1
- JPSREXAVJGNSTI-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-3,5-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC(F)=C1C=C1C(=O)NC(=O)O1 JPSREXAVJGNSTI-UHFFFAOYSA-N 0.000 claims 1
- GKBHJRWEZJZORU-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-3-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)O1 GKBHJRWEZJZORU-UHFFFAOYSA-N 0.000 claims 1
- YLEDUEGAAOPBIF-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-3-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC=C1C=C1C(=O)NC(=O)O1 YLEDUEGAAOPBIF-UHFFFAOYSA-N 0.000 claims 1
- JETAGVVACKUJMX-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2,3-difluorophenyl]propanoate Chemical compound FC1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 JETAGVVACKUJMX-UHFFFAOYSA-N 0.000 claims 1
- NXBIIHZISQJJRE-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 NXBIIHZISQJJRE-UHFFFAOYSA-N 0.000 claims 1
- CMNZTOYBERNPGD-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-fluorophenyl]propanoate Chemical compound C1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 CMNZTOYBERNPGD-UHFFFAOYSA-N 0.000 claims 1
- FSCABNWMGYWGCG-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 FSCABNWMGYWGCG-UHFFFAOYSA-N 0.000 claims 1
- KKVBUVXERMHOBV-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-nitrophenyl]propanoate Chemical compound C1=C([N+]([O-])=O)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 KKVBUVXERMHOBV-UHFFFAOYSA-N 0.000 claims 1
- AVYQFTIBNBIACA-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-3,5-difluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC(F)=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 AVYQFTIBNBIACA-UHFFFAOYSA-N 0.000 claims 1
- PBKXJYGUFLXAJS-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-3-(trifluoromethyl)phenyl]propanoate Chemical compound FC(F)(F)C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 PBKXJYGUFLXAJS-UHFFFAOYSA-N 0.000 claims 1
- UVDFUWKKHVEMSJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-3-fluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 UVDFUWKKHVEMSJ-UHFFFAOYSA-N 0.000 claims 1
- GAQWTIWBVKFNNE-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 GAQWTIWBVKFNNE-UHFFFAOYSA-N 0.000 claims 1
- GEYHSNPJQXXUTH-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2,3-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1F)F)=CC=C1CC1C(=O)NC(=O)S1 GEYHSNPJQXXUTH-UHFFFAOYSA-N 0.000 claims 1
- BWVSFAQOCHIQKO-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1CC1C(=O)NC(=O)S1 BWVSFAQOCHIQKO-UHFFFAOYSA-N 0.000 claims 1
- OHRGYUROFCVMNL-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)F)=CC=C1CC1C(=O)NC(=O)S1 OHRGYUROFCVMNL-UHFFFAOYSA-N 0.000 claims 1
- JJBYDFLJMUHEMF-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methylphenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C)=CC=C1CC1C(=O)NC(=O)S1 JJBYDFLJMUHEMF-UHFFFAOYSA-N 0.000 claims 1
- LQOFRSDZPNFATG-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-nitrophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)[N+]([O-])=O)=CC=C1CC1C(=O)NC(=O)S1 LQOFRSDZPNFATG-UHFFFAOYSA-N 0.000 claims 1
- LNXIYYYEFBIJMP-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-3,5-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC(F)=C1CC1C(=O)NC(=O)S1 LNXIYYYEFBIJMP-UHFFFAOYSA-N 0.000 claims 1
- GUPWMRKXFIBJSD-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-3-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1C(F)(F)F)=CC=C1CC1C(=O)NC(=O)S1 GUPWMRKXFIBJSD-UHFFFAOYSA-N 0.000 claims 1
- SJIUIVVHNVNIEV-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-3-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC=C1CC1C(=O)NC(=O)S1 SJIUIVVHNVNIEV-UHFFFAOYSA-N 0.000 claims 1
- GJGYTLHGCWICCL-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 GJGYTLHGCWICCL-UHFFFAOYSA-N 0.000 claims 1
- ZIIYOFPXXRQIEA-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-2-fluorophenyl]propanoate Chemical compound C1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 ZIIYOFPXXRQIEA-UHFFFAOYSA-N 0.000 claims 1
- OFULTZRBCZWYBV-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 OFULTZRBCZWYBV-UHFFFAOYSA-N 0.000 claims 1
- MBSYURHGUNCPQY-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-2-nitrophenyl]propanoate Chemical compound C1=C([N+]([O-])=O)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 MBSYURHGUNCPQY-UHFFFAOYSA-N 0.000 claims 1
- SDZHNZRFCJBBOX-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-3,5-difluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC(F)=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 SDZHNZRFCJBBOX-UHFFFAOYSA-N 0.000 claims 1
- MUOWZEKPCFZMCB-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-3-(trifluoromethyl)phenyl]propanoate Chemical compound FC(F)(F)C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 MUOWZEKPCFZMCB-UHFFFAOYSA-N 0.000 claims 1
- DMBCGKJRKLTRTJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-3-fluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 DMBCGKJRKLTRTJ-UHFFFAOYSA-N 0.000 claims 1
- OGXRFCWCSMPYKS-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 OGXRFCWCSMPYKS-UHFFFAOYSA-N 0.000 claims 1
- GHCFECFAIHVFKI-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2,3-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1F)F)=CC=C1C=C1C(=O)NC(=O)S1 GHCFECFAIHVFKI-UHFFFAOYSA-N 0.000 claims 1
- SPSPQVIEQWMMAM-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)S1 SPSPQVIEQWMMAM-UHFFFAOYSA-N 0.000 claims 1
- IGONZXKWPXGJJN-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)F)=CC=C1C=C1C(=O)NC(=O)S1 IGONZXKWPXGJJN-UHFFFAOYSA-N 0.000 claims 1
- DQOCRTXCKGTRGM-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-methylphenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C)=CC=C1C=C1C(=O)NC(=O)S1 DQOCRTXCKGTRGM-UHFFFAOYSA-N 0.000 claims 1
- SSSCNHINVDTLTF-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-nitrophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)[N+]([O-])=O)=CC=C1C=C1C(=O)NC(=O)S1 SSSCNHINVDTLTF-UHFFFAOYSA-N 0.000 claims 1
- WJHASNZHBNHDLG-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-3,5-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC(F)=C1C=C1C(=O)NC(=O)S1 WJHASNZHBNHDLG-UHFFFAOYSA-N 0.000 claims 1
- RQJHTLOJRHUWAP-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-3-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)S1 RQJHTLOJRHUWAP-UHFFFAOYSA-N 0.000 claims 1
- VCSWLAKPJQFFCL-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-3-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC=C1C=C1C(=O)NC(=O)S1 VCSWLAKPJQFFCL-UHFFFAOYSA-N 0.000 claims 1
- PQULEHSJUOJFFT-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-2,3-difluorophenyl]propanoate Chemical compound FC1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 PQULEHSJUOJFFT-UHFFFAOYSA-N 0.000 claims 1
- TWSFIKODCFHUIP-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 TWSFIKODCFHUIP-UHFFFAOYSA-N 0.000 claims 1
- FBCABQNGCOSCIR-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-2-fluorophenyl]propanoate Chemical compound C1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 FBCABQNGCOSCIR-UHFFFAOYSA-N 0.000 claims 1
- RIQOOPZWTDWYPS-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 RIQOOPZWTDWYPS-UHFFFAOYSA-N 0.000 claims 1
- FPOKHDJYQNVUQK-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-2-nitrophenyl]propanoate Chemical compound C1=C([N+]([O-])=O)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 FPOKHDJYQNVUQK-UHFFFAOYSA-N 0.000 claims 1
- JIFOUHKXLHEKOI-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-3,5-difluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC(F)=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 JIFOUHKXLHEKOI-UHFFFAOYSA-N 0.000 claims 1
- CGJPRWMVBLTWQM-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-3-(trifluoromethyl)phenyl]propanoate Chemical compound FC(F)(F)C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 CGJPRWMVBLTWQM-UHFFFAOYSA-N 0.000 claims 1
- NFBRNCTYXWMZOA-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-3-fluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 NFBRNCTYXWMZOA-UHFFFAOYSA-N 0.000 claims 1
- TWWVONQNEVLIIH-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 TWWVONQNEVLIIH-UHFFFAOYSA-N 0.000 claims 1
- USOQPLZEWYDGCA-UHFFFAOYSA-N methyl 3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=CC(CC(C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 USOQPLZEWYDGCA-UHFFFAOYSA-N 0.000 claims 1
- ZMEMSCVLZHHICN-UHFFFAOYSA-N methyl 3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=CC(CC(C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 ZMEMSCVLZHHICN-UHFFFAOYSA-N 0.000 claims 1
- AWKFWEAITGHEBY-UHFFFAOYSA-N methyl 3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=CC(CC(C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 AWKFWEAITGHEBY-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 229960003104 ornithine Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 125000002876 tyrosin-O(4)-yl group Chemical group [H]OC(=O)C(N([H])[H])C([H])([H])C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 150000003667 tyrosine derivatives Chemical class 0.000 claims 1
- 0 C[C@@](*C(N1)=O)(C(*)C2=C*(*)C=C(***)*(C)=*2*)C1=O Chemical compound C[C@@](*C(N1)=O)(C(*)C2=C*(*)C=C(***)*(C)=*2*)C1=O 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44077203P | 2003-01-17 | 2003-01-17 | |
| US60/440,772 | 2003-01-17 | ||
| US10/356,113 US6794401B2 (en) | 2003-01-17 | 2003-01-31 | Amino acid phenoxy ethers |
| US10/356,113 | 2003-01-31 | ||
| PCT/US2004/000790 WO2004066964A2 (en) | 2003-01-17 | 2004-01-13 | Amino acid phenoxy ethers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007501288A JP2007501288A (ja) | 2007-01-25 |
| JP2007501288A5 true JP2007501288A5 (https=) | 2008-12-11 |
| JP4833072B2 JP4833072B2 (ja) | 2011-12-07 |
Family
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Family Applications (1)
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|---|---|---|---|
| JP2006536536A Expired - Fee Related JP4833072B2 (ja) | 2003-01-17 | 2004-01-13 | アミノ酸フェノキシエーテル |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US6794401B2 (https=) |
| EP (1) | EP1583529B9 (https=) |
| JP (1) | JP4833072B2 (https=) |
| KR (1) | KR101085315B1 (https=) |
| AT (1) | ATE532510T1 (https=) |
| AU (1) | AU2004207449A1 (https=) |
| BR (1) | BRPI0406772B1 (https=) |
| CA (1) | CA2513496C (https=) |
| CY (1) | CY1112673T1 (https=) |
| DK (1) | DK1583529T3 (https=) |
| EA (1) | EA200501078A1 (https=) |
| ES (1) | ES2374724T3 (https=) |
| MA (1) | MA27658A1 (https=) |
| MX (1) | MXPA05007684A (https=) |
| NO (1) | NO330984B1 (https=) |
| NZ (1) | NZ541328A (https=) |
| PT (1) | PT1583529E (https=) |
| SI (1) | SI1583529T1 (https=) |
| TW (1) | TWI325420B (https=) |
| WO (1) | WO2004066964A2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7521465B2 (en) * | 2003-01-17 | 2009-04-21 | Bexel Pharmaceuticals, Inc. | Diphenyl ether derivatives |
| US7781464B2 (en) * | 2003-01-17 | 2010-08-24 | Bexel Pharmaceuticals, Inc. | Heterocyclic diphenyl ethers |
| US7087576B2 (en) * | 2003-10-07 | 2006-08-08 | Bexel Pharmaceuticals, Inc. | Dipeptide phenyl ethers |
| US7592486B2 (en) * | 2004-09-16 | 2009-09-22 | Board Of Regents Of The University Of Nebraska | Anhydrous fluoride salts and reagents and methods for their production |
| KR20080025662A (ko) * | 2005-03-18 | 2008-03-21 | 오키드 케미칼즈 앤드 파마수티컬즈 리미티드 | 신규 티로신 유도체 |
| US20090203744A1 (en) * | 2005-07-29 | 2009-08-13 | Pande Y Surendrakumar Satyanarayan | Novel pyridine derivatives |
| WO2008019306A2 (en) * | 2006-08-04 | 2008-02-14 | Decode Genetics Ehf | Aryl amino acid derivatives as inhibitors of lta4h (leukotriene a4 hydrolase) for treating inflammation |
| CN101784269A (zh) * | 2007-06-26 | 2010-07-21 | 莱西肯医药有限公司 | 治疗由5-羟色胺介导的疾病和病症的方法 |
| CN101815534A (zh) | 2007-07-11 | 2010-08-25 | 莱西肯医药有限公司 | 用于治疗肺动脉高压以及相关疾病和病症的方法和组合物 |
| WO2009030968A1 (en) * | 2007-09-05 | 2009-03-12 | Orchid Research Laboratories Limited | Mao a inhibitors with a diphenyl ether-substructure. |
| ATE536347T1 (de) | 2008-05-20 | 2011-12-15 | Merck Sharp & Dohme | Effiziente herstellung heterologer proteine unter verwendung von mannosyltransferaseinhibitoren |
| US20140187594A1 (en) | 2010-07-28 | 2014-07-03 | Orchid Chemicals And Pharmaceuticals Ltd | Diphenyl ether compounds for the treatment of liver, lung disorders, diabetic complications and cardiovascular diseases |
| JP6014816B2 (ja) | 2011-05-10 | 2016-10-26 | 国立大学法人神戸大学 | Ｒａｓ機能阻害作用を有するチオキソチアゾリジン誘導体 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020049240A1 (en) * | 1994-12-19 | 2002-04-25 | Beecham Group P.1.C. | Novel compounds |
| US5166137A (en) | 1991-03-27 | 1992-11-24 | Nobipols Forskningsstiftelse | Guluronic acid polymers and use of same for inhibition of cytokine production |
| US5441971A (en) * | 1991-04-11 | 1995-08-15 | The Upjohn Company | Thiazolidinedione derivatives, production and use thereof |
| ATE185564T1 (de) * | 1992-08-31 | 1999-10-15 | Sankyo Co | Oxazolidin-derivate mit antidiabetika und anti- fettleibigkeit-eigenschaften, ihre herstellung und therapeutische verwendung |
| TW268952B (https=) * | 1993-02-26 | 1996-01-21 | Takeda Pharm Industry Co Ltd | |
| AU679572B2 (en) * | 1993-09-15 | 1997-07-03 | Daiichi Sankyo Company, Limited | Use of thiazolidinediones to prevent or delay onset of NIDDM |
| US5527546A (en) | 1994-08-10 | 1996-06-18 | Bayer Corporation | Human interleukin 6 inhibitor |
| DE4432101A1 (de) * | 1994-09-09 | 1996-03-14 | Hoechst Ag | Aminosäure-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| JP4173539B2 (ja) | 1995-05-11 | 2008-10-29 | ラボラトアール・セローノ・ソシエテ・アノニム | Ｉｌ−６活性阻害剤 |
| CZ293016B6 (cs) * | 1995-06-01 | 2004-01-14 | Sankyo Company Limited | Benzimidazolové deriváty a farmaceutické prostředky s jejich obsahem |
| TWI238064B (en) * | 1995-06-20 | 2005-08-21 | Takeda Chemical Industries Ltd | A pharmaceutical composition for prophylaxis and treatment of diabetes |
| TW577875B (en) * | 1997-01-31 | 2004-03-01 | Shionogi & Co | Pyrrolidine derivatives with inhibitory activity for phospholipase A2 |
| JPH11124331A (ja) * | 1997-08-21 | 1999-05-11 | Takeda Chem Ind Ltd | 抗炎症剤 |
| US6331633B1 (en) | 1998-05-08 | 2001-12-18 | Calyx Therapeutics Inc. | Heterocyclic analogs of diphenylethylene compounds |
| US6699896B1 (en) * | 1998-05-12 | 2004-03-02 | Wyeth | Oxazole-aryl-carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
| TR200003595T2 (tr) * | 1998-06-05 | 2001-07-23 | Astrazeneca Ab | Kimyasal bileşikler |
| US6664281B1 (en) * | 1998-08-27 | 2003-12-16 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| NZ515086A (en) | 1999-04-28 | 2003-10-31 | Aventis Pharma Gmbh | Di-aryl acid derivatives as PPAR receptor ligands |
| TWI284533B (en) * | 1999-05-24 | 2007-08-01 | Sankyo Co | Pharmaceutical composition for treating hyperglycemia, impaired glucose tolerance, diabetes complications and for improving insulin resistant |
| EP1109796A1 (en) | 1999-07-01 | 2001-06-27 | Geron Corporation | Telomerase inhibitors and methods of their use |
| HUP0202520A3 (en) * | 1999-08-23 | 2004-11-29 | Kyorin Seiyaku Kk | Substituted benzylthiazolidine-2,4-dione derivatives and pharmaceutical compositions containing them |
| NZ517993A (en) * | 1999-08-31 | 2004-03-26 | Incyte San Diego Inc | Benzylidene-thiazolidinediones and analogues and their use in the treatment of diabetes |
| JP2001199888A (ja) * | 2000-01-24 | 2001-07-24 | Fujimoto Brothers:Kk | 糖尿病治療剤 |
| JP2001294537A (ja) * | 2000-02-10 | 2001-10-23 | Takeda Chem Ind Ltd | 併用医薬 |
| ATE310733T1 (de) | 2000-04-21 | 2005-12-15 | Pfizer Prod Inc | Thyroid-rezeptorliganden |
| US6680387B2 (en) * | 2000-04-24 | 2004-01-20 | Aryx Therapeutics | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
-
2003
- 2003-01-31 US US10/356,113 patent/US6794401B2/en not_active Expired - Lifetime
-
2004
- 2004-01-13 ES ES04701752T patent/ES2374724T3/es not_active Expired - Lifetime
- 2004-01-13 CA CA2513496A patent/CA2513496C/en not_active Expired - Fee Related
- 2004-01-13 EP EP04701752A patent/EP1583529B9/en not_active Expired - Lifetime
- 2004-01-13 AU AU2004207449A patent/AU2004207449A1/en not_active Abandoned
- 2004-01-13 SI SI200431804T patent/SI1583529T1/sl unknown
- 2004-01-13 KR KR1020057013193A patent/KR101085315B1/ko not_active Expired - Fee Related
- 2004-01-13 DK DK04701752.0T patent/DK1583529T3/da active
- 2004-01-13 AT AT04701752T patent/ATE532510T1/de active
- 2004-01-13 EA EA200501078A patent/EA200501078A1/ru unknown
- 2004-01-13 MX MXPA05007684A patent/MXPA05007684A/es active IP Right Grant
- 2004-01-13 PT PT04701752T patent/PT1583529E/pt unknown
- 2004-01-13 BR BRPI0406772A patent/BRPI0406772B1/pt not_active IP Right Cessation
- 2004-01-13 NZ NZ541328A patent/NZ541328A/en not_active IP Right Cessation
- 2004-01-13 WO PCT/US2004/000790 patent/WO2004066964A2/en not_active Ceased
- 2004-01-13 JP JP2006536536A patent/JP4833072B2/ja not_active Expired - Fee Related
- 2004-01-14 TW TW093100932A patent/TWI325420B/zh not_active IP Right Cessation
- 2004-09-21 US US10/947,047 patent/US20050096366A1/en not_active Abandoned
-
2005
- 2005-08-01 NO NO20053714A patent/NO330984B1/no not_active IP Right Cessation
- 2005-08-16 MA MA28444A patent/MA27658A1/fr unknown
-
2012
- 2012-02-09 CY CY20121100137T patent/CY1112673T1/el unknown
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