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 |
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| US44077203P | 2003-01-17 | 2003-01-17 | |
| US60/440,772 | 2003-01-17 | ||
| US10/356,113 | 2003-01-31 | ||
| US10/356,113 US6794401B2 (en) | 2003-01-17 | 2003-01-31 | Amino acid phenoxy ethers |
| 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)
| Application Number | Title | Priority Date | Filing Date |
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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 |
| EP1858845A2 (en) * | 2005-03-18 | 2007-11-28 | Orchid Chemicals and Pharmaceuticals Limited | Novel tyrosine derivatives |
| US20090203744A1 (en) * | 2005-07-29 | 2009-08-13 | Pande Y Surendrakumar Satyanarayan | Novel pyridine derivatives |
| EP2066800A2 (en) * | 2006-08-04 | 2009-06-10 | Decode Genetics EHF | Aryl amino acid derivatives as inhibitors of lta4h (leukotriene a4 hydrolase) for treating inflammation |
| EP2170306A1 (en) * | 2007-06-26 | 2010-04-07 | Lexicon Pharmaceuticals, Inc. | Methods of treating serotonin-mediated diseases and disorders |
| US7875622B2 (en) | 2007-07-11 | 2011-01-25 | Lexicon Pharmaceuticals, Inc. | Methods and compositions for treating pulmonary hypertension and related diseases and disorders |
| WO2009030968A1 (en) * | 2007-09-05 | 2009-03-12 | Orchid Research Laboratories Limited | Mao a inhibitors with a diphenyl ether-substructure. |
| WO2009143041A1 (en) | 2008-05-20 | 2009-11-26 | Merck & Co., Inc. | Efficient production of heterologous proteins using mannosyl transferase inhibitors |
| CN103108634B (zh) | 2010-07-28 | 2015-08-12 | 幽兰化学医药有限公司 | 用于治疗肝病、肺病、糖尿病并发症和心血管疾病的二苯醚化合物 |
| US9056862B2 (en) | 2011-05-10 | 2015-06-16 | National University Corporation Kobe University | Thioxothiazolidine derivative having Ras function inhibitory effect |
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 |
| ES2139633T3 (es) * | 1992-08-31 | 2000-02-16 | Sankyo Co | Derivados de oxazolidina con propiedades anti-diabetica y anti-obesidad, su preparacion y su utilizacion terapeutica. |
| TW268952B (https=) * | 1993-02-26 | 1996-01-21 | Takeda Pharm Industry Co Ltd | |
| NZ274346A (en) * | 1993-09-15 | 1997-06-24 | Sankyo Co | Use of various thiazolidine-2,4-dione and oxazolidine-2,4-dione derivatives to prevent or delay onset of non-insulin dependent diabetes mellitus |
| 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 |
| ATE271128T1 (de) | 1995-05-11 | 2004-07-15 | Applied Research Systems | Inhibitoren der il-6 aktivitaet |
| IL118474A (en) * | 1995-06-01 | 2001-08-08 | Sankyo Co | Benzimideol derivatives and pharmaceutical preparations containing them |
| 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 |
| WO1999064417A2 (en) * | 1998-06-05 | 1999-12-16 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| US6664281B1 (en) * | 1998-08-27 | 2003-12-16 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| YU72201A (sh) | 1999-04-28 | 2005-07-19 | Aventis Pharma Deutschland Gmbh. | Derivati di-aril kiseline kao ppar receptorski ligandi |
| 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 |
| KR20010099634A (ko) | 1999-07-01 | 2001-11-09 | 할리 켈빈 비. | 텔로머라제 저해제 및 그 사용 방법 |
| CN1155586C (zh) * | 1999-08-23 | 2004-06-30 | 杏林制药株式会社 | 取代的苄基噻唑烷-2,4-二酮衍生物 |
| JP2003508391A (ja) * | 1999-08-31 | 2003-03-04 | マキシア・ファーマシューティカルズ・インコーポレイテッド | ベンジリデン−チアゾリジンジオン類およびアナログ類ならびに糖尿病の治療におけるその使用 |
| 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 |
| EP1148054B1 (en) | 2000-04-21 | 2005-11-23 | Pfizer Products Inc. | Thyroid receptor ligands |
| 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 KR KR1020057013193A patent/KR101085315B1/ko not_active Expired - Fee Related
- 2004-01-13 EP EP04701752A patent/EP1583529B9/en not_active Expired - Lifetime
- 2004-01-13 ES ES04701752T patent/ES2374724T3/es not_active Expired - Lifetime
- 2004-01-13 JP JP2006536536A patent/JP4833072B2/ja not_active Expired - Fee Related
- 2004-01-13 DK DK04701752.0T patent/DK1583529T3/da active
- 2004-01-13 CA CA2513496A patent/CA2513496C/en not_active Expired - Fee Related
- 2004-01-13 MX MXPA05007684A patent/MXPA05007684A/es active IP Right Grant
- 2004-01-13 PT PT04701752T patent/PT1583529E/pt unknown
- 2004-01-13 NZ NZ541328A patent/NZ541328A/en not_active IP Right Cessation
- 2004-01-13 AT AT04701752T patent/ATE532510T1/de active
- 2004-01-13 EA EA200501078A patent/EA200501078A1/ru unknown
- 2004-01-13 SI SI200431804T patent/SI1583529T1/sl unknown
- 2004-01-13 AU AU2004207449A patent/AU2004207449A1/en not_active Abandoned
- 2004-01-13 BR BRPI0406772A patent/BRPI0406772B1/pt not_active IP Right Cessation
- 2004-01-13 WO PCT/US2004/000790 patent/WO2004066964A2/en not_active Ceased
- 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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