ES2374724T3 - Fenoxi éteres de aminoácido, su preparación y usos. - Google Patents
Fenoxi éteres de aminoácido, su preparación y usos. Download PDFInfo
- Publication number
- ES2374724T3 ES2374724T3 ES04701752T ES04701752T ES2374724T3 ES 2374724 T3 ES2374724 T3 ES 2374724T3 ES 04701752 T ES04701752 T ES 04701752T ES 04701752 T ES04701752 T ES 04701752T ES 2374724 T3 ES2374724 T3 ES 2374724T3
- Authority
- ES
- Spain
- Prior art keywords
- amino
- salts
- 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.)
- Expired - Lifetime
Links
- -1 PHENOXY AMINO Chemical class 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims description 15
- 238000011282 treatment Methods 0.000 claims abstract description 33
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- 230000004054 inflammatory process Effects 0.000 claims abstract description 19
- 206010061218 Inflammation Diseases 0.000 claims abstract description 18
- 208000026278 immune system disease Diseases 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims description 346
- 150000001875 compounds Chemical class 0.000 claims description 151
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229940024606 amino acid Drugs 0.000 claims description 29
- 235000001014 amino acid Nutrition 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 150000001413 amino acids Chemical class 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 239000011593 sulfur Substances 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
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- 125000003277 amino group Chemical group 0.000 claims description 17
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
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- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 8
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004475 Arginine Substances 0.000 claims description 5
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 5
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- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 5
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- 125000005843 halogen group Chemical group 0.000 claims description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- SARPBCXOAPTYNU-UHFFFAOYSA-N methyl 3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-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)S1 SARPBCXOAPTYNU-UHFFFAOYSA-N 0.000 claims description 4
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- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 3
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
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- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 3
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- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 3
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- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 3
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- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 3
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- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000539 amino acid group Chemical group 0.000 claims description 3
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- 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 description 3
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- 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 description 2
- 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 description 2
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- 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 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 235000021588 free fatty acids Nutrition 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- XGVXRQUIWYNAJC-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-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)O1 XGVXRQUIWYNAJC-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- ILGUXHBABDWGAU-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-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)S1 ILGUXHBABDWGAU-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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Classifications
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
Landscapes
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Transplantation (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US356113 | 1999-07-16 | ||
| US44077203P | 2003-01-17 | 2003-01-17 | |
| US440772P | 2003-01-17 | ||
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| ES2374724T3 true ES2374724T3 (es) | 2012-02-21 |
Family
ID=32716922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04701752T Expired - Lifetime ES2374724T3 (es) | 2003-01-17 | 2004-01-13 | Fenoxi éteres de aminoácido, su preparación y usos. |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US6794401B2 (enExample) |
| EP (1) | EP1583529B9 (enExample) |
| JP (1) | JP4833072B2 (enExample) |
| KR (1) | KR101085315B1 (enExample) |
| AT (1) | ATE532510T1 (enExample) |
| AU (1) | AU2004207449A1 (enExample) |
| BR (1) | BRPI0406772B1 (enExample) |
| CA (1) | CA2513496C (enExample) |
| CY (1) | CY1112673T1 (enExample) |
| DK (1) | DK1583529T3 (enExample) |
| EA (1) | EA200501078A1 (enExample) |
| ES (1) | ES2374724T3 (enExample) |
| MA (1) | MA27658A1 (enExample) |
| MX (1) | MXPA05007684A (enExample) |
| NO (1) | NO330984B1 (enExample) |
| NZ (1) | NZ541328A (enExample) |
| PT (1) | PT1583529E (enExample) |
| SI (1) | SI1583529T1 (enExample) |
| TW (1) | TWI325420B (enExample) |
| WO (1) | WO2004066964A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7781464B2 (en) * | 2003-01-17 | 2010-08-24 | Bexel Pharmaceuticals, Inc. | Heterocyclic diphenyl ethers |
| US7521465B2 (en) * | 2003-01-17 | 2009-04-21 | Bexel Pharmaceuticals, Inc. | Diphenyl ether derivatives |
| 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 |
| JP2008533122A (ja) * | 2005-03-18 | 2008-08-21 | オーキッド ケミカルズ アンド ファーマシューティカルズ リミテッド | 新規なチロシン誘導体 |
| WO2007029062A2 (en) * | 2005-07-29 | 2007-03-15 | Orchid Research Laboratories Limited | Novel pyridine derivatives |
| US7989480B2 (en) | 2006-08-04 | 2011-08-02 | Decode Genetics Ehf | Aryl amino acid derivatives as inhibitors for treating inflammation |
| KR20100037047A (ko) * | 2007-06-26 | 2010-04-08 | 렉시컨 파마슈티컬스 인코퍼레이티드 | 세로토닌-매개 질환 및 장애의 치료 방법 |
| AU2008275179B2 (en) | 2007-07-11 | 2013-09-12 | 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. |
| 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 |
| WO2012153775A1 (ja) | 2011-05-10 | 2012-11-15 | 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 (enExample) * | 1993-02-26 | 1996-01-21 | Takeda Pharm Industry Co Ltd | |
| CA2171827C (en) * | 1993-09-15 | 2004-06-29 | Jerrold Olefsky | 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 |
| WO1996035782A1 (en) * | 1995-05-11 | 1996-11-14 | Applied Research Systems | Il-6 activity inhibitor |
| IL118474A (en) * | 1995-06-01 | 2001-08-08 | Sankyo Co | Benzimideol derivatives and pharmaceutical preparations containing them |
| TW438587B (en) * | 1995-06-20 | 2001-06-07 | 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 |
| HUP0103082A3 (en) * | 1998-06-05 | 2002-12-28 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| KR100613175B1 (ko) * | 1998-08-27 | 2006-08-17 | 오노 야꾸힝 고교 가부시키가이샤 | 카르복실산 유도체 및 그 유도체를 유효 성분으로서함유하는 약제 |
| PT1177187E (pt) | 1999-04-28 | 2007-09-03 | Sanofi Aventis Deutschland | Derivados ácidos de di-arilo como ligados do receptor ppar. |
| 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 |
| WO2001002377A1 (en) | 1999-07-01 | 2001-01-11 | Geron Corporation | Telomerase inhibitors and methods of their use |
| AU778720B2 (en) * | 1999-08-23 | 2004-12-16 | Kyorin Pharmaceutical Co. Ltd. | Substituted benzylthiazolidine-2,4-dione derivatives |
| US6515003B1 (en) * | 1999-08-31 | 2003-02-04 | Maxia Pharmaceuticals, Inc. | Heterocyclic derivatives for the treatment of diabetes and other diseases |
| 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 |
| DE60115132T2 (de) | 2000-04-21 | 2006-07-06 | Pfizer Products Inc., Groton | 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 BR BRPI0406772A patent/BRPI0406772B1/pt not_active IP Right Cessation
- 2004-01-13 PT PT04701752T patent/PT1583529E/pt unknown
- 2004-01-13 MX MXPA05007684A patent/MXPA05007684A/es active IP Right Grant
- 2004-01-13 NZ NZ541328A patent/NZ541328A/en not_active IP Right Cessation
- 2004-01-13 SI SI200431804T patent/SI1583529T1/sl unknown
- 2004-01-13 ES ES04701752T patent/ES2374724T3/es not_active Expired - Lifetime
- 2004-01-13 AT AT04701752T patent/ATE532510T1/de active
- 2004-01-13 AU AU2004207449A patent/AU2004207449A1/en not_active Abandoned
- 2004-01-13 JP JP2006536536A patent/JP4833072B2/ja not_active Expired - Fee Related
- 2004-01-13 EP EP04701752A patent/EP1583529B9/en not_active Expired - Lifetime
- 2004-01-13 EA EA200501078A patent/EA200501078A1/ru unknown
- 2004-01-13 CA CA2513496A patent/CA2513496C/en not_active Expired - Fee Related
- 2004-01-13 DK DK04701752.0T patent/DK1583529T3/da active
- 2004-01-13 KR KR1020057013193A patent/KR101085315B1/ko not_active Expired - Fee Related
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| DK1583529T3 (da) | 2012-01-23 |
| KR101085315B1 (ko) | 2011-11-22 |
| NZ541328A (en) | 2008-11-28 |
| EP1583529A2 (en) | 2005-10-12 |
| WO2004066964A2 (en) | 2004-08-12 |
| BRPI0406772A (pt) | 2005-12-27 |
| ATE532510T1 (de) | 2011-11-15 |
| NO330984B1 (no) | 2011-08-29 |
| TWI325420B (en) | 2010-06-01 |
| KR20050092764A (ko) | 2005-09-22 |
| WO2004066964A9 (en) | 2004-09-02 |
| JP4833072B2 (ja) | 2011-12-07 |
| WO2004066964A3 (en) | 2005-02-24 |
| TW200418792A (en) | 2004-10-01 |
| US6794401B2 (en) | 2004-09-21 |
| NO20053714L (no) | 2005-10-11 |
| MXPA05007684A (es) | 2006-03-10 |
| MA27658A1 (fr) | 2005-12-01 |
| BRPI0406772B1 (pt) | 2016-08-23 |
| NO20053714D0 (no) | 2005-08-01 |
| JP2007501288A (ja) | 2007-01-25 |
| EP1583529A4 (en) | 2007-07-04 |
| PT1583529E (pt) | 2012-02-13 |
| SI1583529T1 (sl) | 2012-02-29 |
| EA200501078A1 (ru) | 2006-02-24 |
| CY1112673T1 (el) | 2016-02-10 |
| US20050096366A1 (en) | 2005-05-05 |
| CA2513496A1 (en) | 2004-08-12 |
| EP1583529B9 (en) | 2012-04-04 |
| AU2004207449A1 (en) | 2004-08-12 |
| EP1583529B1 (en) | 2011-11-09 |
| CA2513496C (en) | 2013-05-14 |
| US20040142991A1 (en) | 2004-07-22 |
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