HUP0105477A2 - Metalloproteináz mátrixok reverz hidroxamát inhibitorai és alkalmazásuk gyógyszerkészítmények előállítására - Google Patents
Metalloproteináz mátrixok reverz hidroxamát inhibitorai és alkalmazásuk gyógyszerkészítmények előállítására Download PDFInfo
- Publication number
- HUP0105477A2 HUP0105477A2 HU0105477A HUP0105477A HUP0105477A2 HU P0105477 A2 HUP0105477 A2 HU P0105477A2 HU 0105477 A HU0105477 A HU 0105477A HU P0105477 A HUP0105477 A HU P0105477A HU P0105477 A2 HUP0105477 A2 HU P0105477A2
- Authority
- HU
- Hungary
- Prior art keywords
- propionic acid
- acetylamino
- ylamino
- nitrophenyl
- methylpyridin
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
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- 108010000684 Matrix Metalloproteinases Proteins 0.000 title abstract 2
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- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 108010044426 integrins Proteins 0.000 claims description 80
- 102000006495 integrins Human genes 0.000 claims description 80
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- YYZIYTNXNDEEJN-UHFFFAOYSA-N 3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(3-nitrophenyl)propanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC(O)=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 YYZIYTNXNDEEJN-UHFFFAOYSA-N 0.000 claims description 11
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- KKDCLXHJKZLXTA-UHFFFAOYSA-N 3-(4-chloro-3-nitrophenyl)-3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]propanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=NC(NCCCCC(=O)NCC(=O)NC(CC(O)=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 KKDCLXHJKZLXTA-UHFFFAOYSA-N 0.000 claims description 10
- XYTIMKXICDYNHJ-UHFFFAOYSA-N 3-(4-methyl-3-nitrophenyl)-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC(O)=O)C=2C=C(C(C)=CC=2)[N+]([O-])=O)=C1 XYTIMKXICDYNHJ-UHFFFAOYSA-N 0.000 claims description 10
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- WHBCNNHVVDCHQZ-UHFFFAOYSA-N methyl 3-(4-methyl-3-nitrophenyl)-3-[[2-[4-(pyrimidin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C)C([N+]([O-])=O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=NC=CC=N1 WHBCNNHVVDCHQZ-UHFFFAOYSA-N 0.000 description 1
- XLSHNOANTAMNLG-UHFFFAOYSA-N methyl 3-(4-methyl-3-nitrophenyl)-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C)C([N+]([O-])=O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 XLSHNOANTAMNLG-UHFFFAOYSA-N 0.000 description 1
- HIEIVXFDFAHHIQ-UHFFFAOYSA-N methyl 3-(4-methyl-3-nitrophenyl)-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C)C([N+]([O-])=O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 HIEIVXFDFAHHIQ-UHFFFAOYSA-N 0.000 description 1
- JBUWDJCNZJWZQN-UHFFFAOYSA-N methyl 3-(4-methyl-3-nitrophenyl)-3-[[2-[5-[(6-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C)C([N+]([O-])=O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC(C)=N1 JBUWDJCNZJWZQN-UHFFFAOYSA-N 0.000 description 1
- ACMCNOGMGHJTQF-UHFFFAOYSA-N methyl 3-(4-methyl-3-nitrophenyl)-3-[[2-[6-[(4-methylpyridin-2-yl)amino]hexanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C)C([N+]([O-])=O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCCNC1=CC(C)=CC=N1 ACMCNOGMGHJTQF-UHFFFAOYSA-N 0.000 description 1
- ROSQUNOENZRPFX-UHFFFAOYSA-N methyl 3-(4-naphthalen-1-ylphenyl)-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C3=CC=CC=C3C=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC=CC=N1 ROSQUNOENZRPFX-UHFFFAOYSA-N 0.000 description 1
- UADFHEXIXAYOKD-UHFFFAOYSA-N methyl 3-(4-naphthalen-1-ylphenyl)-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C3=CC=CC=C3C=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 UADFHEXIXAYOKD-UHFFFAOYSA-N 0.000 description 1
- BDSLAEMOKMXMDT-UHFFFAOYSA-N methyl 3-(4-naphthalen-2-ylphenyl)-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=C3C=CC=CC3=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 BDSLAEMOKMXMDT-UHFFFAOYSA-N 0.000 description 1
- GNZVCOIVVWGANG-UHFFFAOYSA-N methyl 3-(4-phenylphenyl)-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC=CC=N1 GNZVCOIVVWGANG-UHFFFAOYSA-N 0.000 description 1
- GTVRBOYQRBAAEE-UHFFFAOYSA-N methyl 3-(4-phenylphenyl)-3-[[2-[4-(pyrimidin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=NC=CC=N1 GTVRBOYQRBAAEE-UHFFFAOYSA-N 0.000 description 1
- YQSJYWFGXRQIBT-UHFFFAOYSA-N methyl 3-(4-phenylphenyl)-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 YQSJYWFGXRQIBT-UHFFFAOYSA-N 0.000 description 1
- UWKXOKZNYYVCPK-UHFFFAOYSA-N methyl 3-(4-phenylphenyl)-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 UWKXOKZNYYVCPK-UHFFFAOYSA-N 0.000 description 1
- WOMQGDZKCHVMBP-UHFFFAOYSA-N methyl 3-(4-phenylphenyl)-3-[[2-[5-(pyrimidin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=NC=CC=N1 WOMQGDZKCHVMBP-UHFFFAOYSA-N 0.000 description 1
- IOONBLJHGZHSEW-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-(2-hydroxy-3-nitrophenyl)propanoate;hydrochloride Chemical compound Cl.COC(=O)CC(NC(=O)CN)C1=CC=CC([N+]([O-])=O)=C1O IOONBLJHGZHSEW-UHFFFAOYSA-N 0.000 description 1
- PSPMXXGHNOFUKD-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-(2-hydroxy-4-naphthalen-1-ylphenyl)propanoate;hydrochloride Chemical compound Cl.C1=C(O)C(C(NC(=O)CN)CC(=O)OC)=CC=C1C1=CC=CC2=CC=CC=C12 PSPMXXGHNOFUKD-UHFFFAOYSA-N 0.000 description 1
- MDGHMASNIIFSKM-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-(4-nitrophenyl)propanoate;hydrochloride Chemical compound Cl.COC(=O)CC(NC(=O)CN)C1=CC=C([N+]([O-])=O)C=C1 MDGHMASNIIFSKM-UHFFFAOYSA-N 0.000 description 1
- RGOKMLMUUWVSPC-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-(5-bromo-2-hydroxy-3-nitrophenyl)propanoate;hydrochloride Chemical compound Cl.COC(=O)CC(NC(=O)CN)C1=CC(Br)=CC([N+]([O-])=O)=C1O RGOKMLMUUWVSPC-UHFFFAOYSA-N 0.000 description 1
- KRWSWDRZHUJXRD-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-[4-(2-fluorophenyl)phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(C(NC(=O)CN)CC(=O)OC)=CC=C1C1=CC=CC=C1F KRWSWDRZHUJXRD-UHFFFAOYSA-N 0.000 description 1
- QQYISIZLLXWAIX-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-[4-(3-chloro-4-fluorophenyl)phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(C(NC(=O)CN)CC(=O)OC)=CC=C1C1=CC=C(F)C(Cl)=C1 QQYISIZLLXWAIX-UHFFFAOYSA-N 0.000 description 1
- BSPRHGLELYGBRE-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-[4-(3-chlorophenyl)phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(C(NC(=O)CN)CC(=O)OC)=CC=C1C1=CC=CC(Cl)=C1 BSPRHGLELYGBRE-UHFFFAOYSA-N 0.000 description 1
- KRVFPJFETZIUJC-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-[4-(3-fluorophenyl)phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(C(NC(=O)CN)CC(=O)OC)=CC=C1C1=CC=CC(F)=C1 KRVFPJFETZIUJC-UHFFFAOYSA-N 0.000 description 1
- QEQMCYAASDZNBW-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-[4-(4-chlorophenyl)phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(C(NC(=O)CN)CC(=O)OC)=CC=C1C1=CC=C(Cl)C=C1 QEQMCYAASDZNBW-UHFFFAOYSA-N 0.000 description 1
- UFYCEVSWGZUJEQ-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-[4-(4-fluoro-2-hydroxyphenyl)phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(C(NC(=O)CN)CC(=O)OC)=CC=C1C1=CC=C(F)C=C1O UFYCEVSWGZUJEQ-UHFFFAOYSA-N 0.000 description 1
- JNUQMZPZAAFQQV-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-[4-(4-fluorophenyl)-3-hydroxyphenyl]propanoate;hydrochloride Chemical compound Cl.OC1=CC(C(NC(=O)CN)CC(=O)OC)=CC=C1C1=CC=C(F)C=C1 JNUQMZPZAAFQQV-UHFFFAOYSA-N 0.000 description 1
- VSQNCPVLVXBADD-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-[4-(4-methylphenyl)phenyl]propanoate hydrochloride Chemical compound Cl.COC(=O)CC(NC(=O)CN)c1ccc(cc1)-c1ccc(C)cc1 VSQNCPVLVXBADD-UHFFFAOYSA-N 0.000 description 1
- JZSISVRVWMGYMM-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-[4-(trifluoromethoxy)phenyl]propanoate;hydrochloride Chemical compound Cl.COC(=O)CC(NC(=O)CN)C1=CC=C(OC(F)(F)F)C=C1 JZSISVRVWMGYMM-UHFFFAOYSA-N 0.000 description 1
- ZSRYVQCSTDWUJQ-UHFFFAOYSA-N methyl 3-[(2-aminoacetyl)amino]-3-[4-[4-(trifluoromethyl)phenyl]phenyl]propanoate hydrochloride Chemical compound Cl.COC(CC(C1=CC=C(C=C1)C1=CC=C(C=C1)C(F)(F)F)NC(CN)=O)=O ZSRYVQCSTDWUJQ-UHFFFAOYSA-N 0.000 description 1
- WXIWUPBVKGEPQB-UHFFFAOYSA-N methyl 3-[3-(4-fluorophenyl)phenyl]-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound C=1C=CC(C=2C=CC(F)=CC=2)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC=CC=N1 WXIWUPBVKGEPQB-UHFFFAOYSA-N 0.000 description 1
- BWZVONXABQFFLI-UHFFFAOYSA-N methyl 3-[3-(4-fluorophenyl)phenyl]-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound C=1C=CC(C=2C=CC(F)=CC=2)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 BWZVONXABQFFLI-UHFFFAOYSA-N 0.000 description 1
- MVQPGSCJMJRRNM-UHFFFAOYSA-N methyl 3-[3-(4-fluorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=CC(C=2C=CC(F)=CC=2)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 MVQPGSCJMJRRNM-UHFFFAOYSA-N 0.000 description 1
- UVYWDWSZZDPESI-UHFFFAOYSA-N methyl 3-[4-(3-chloro-4-fluorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=C(Cl)C(F)=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 UVYWDWSZZDPESI-UHFFFAOYSA-N 0.000 description 1
- JYMONYWNOLJBPE-UHFFFAOYSA-N methyl 3-[4-(3-chlorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=C(Cl)C=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 JYMONYWNOLJBPE-UHFFFAOYSA-N 0.000 description 1
- BCXZBAPVTFOGQJ-UHFFFAOYSA-N methyl 3-[4-(3-fluorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=C(F)C=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 BCXZBAPVTFOGQJ-UHFFFAOYSA-N 0.000 description 1
- XIQLXKDRSLEYMP-UHFFFAOYSA-N methyl 3-[4-(4-chlorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 XIQLXKDRSLEYMP-UHFFFAOYSA-N 0.000 description 1
- CRUPZBUWSWATIJ-UHFFFAOYSA-N methyl 3-[4-(4-fluoro-2-hydroxyphenyl)phenyl]-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C(=CC(F)=CC=2)O)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 CRUPZBUWSWATIJ-UHFFFAOYSA-N 0.000 description 1
- UHMMVOALUHUWIA-UHFFFAOYSA-N methyl 3-[4-(4-fluorophenyl)-3-hydroxyphenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=CC(F)=CC=2)C(O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 UHMMVOALUHUWIA-UHFFFAOYSA-N 0.000 description 1
- HUGCMKBMMKOJTQ-UHFFFAOYSA-N methyl 3-[4-(4-fluorophenyl)phenyl]-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=CC(F)=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 HUGCMKBMMKOJTQ-UHFFFAOYSA-N 0.000 description 1
- SLKJZLBLUDYNEZ-UHFFFAOYSA-N methyl 3-[4-(4-fluorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=CC(F)=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 SLKJZLBLUDYNEZ-UHFFFAOYSA-N 0.000 description 1
- NIZNOFPBRRNJTF-UHFFFAOYSA-N methyl 3-[4-(4-methylphenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound C=1C=C(C=2C=CC(C)=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 NIZNOFPBRRNJTF-UHFFFAOYSA-N 0.000 description 1
- UAFSMEDVWPBTGI-UHFFFAOYSA-N methyl 3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(3-nitrophenyl)propanoate Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 UAFSMEDVWPBTGI-UHFFFAOYSA-N 0.000 description 1
- IRUHDPNLTHRFJP-UHFFFAOYSA-N methyl 3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(3-nitrophenyl)propanoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=CC([N+]([O-])=O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 IRUHDPNLTHRFJP-UHFFFAOYSA-N 0.000 description 1
- ZJVSUOPNDJMROE-UHFFFAOYSA-N methyl 3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(4-naphthalen-1-ylphenyl)propanoate Chemical compound C=1C=C(C=2C3=CC=CC=C3C=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 ZJVSUOPNDJMROE-UHFFFAOYSA-N 0.000 description 1
- FVRSXDVBMBAUEL-UHFFFAOYSA-N methyl 3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(4-naphthalen-2-ylphenyl)propanoate Chemical compound C=1C=C(C=2C=C3C=CC=CC3=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 FVRSXDVBMBAUEL-UHFFFAOYSA-N 0.000 description 1
- MHHKSYYYWWFSFP-UHFFFAOYSA-N methyl 3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(4-nitrophenyl)propanoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 MHHKSYYYWWFSFP-UHFFFAOYSA-N 0.000 description 1
- CVOUAUIACAZGNM-UHFFFAOYSA-N methyl 3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(4-phenylphenyl)propanoate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 CVOUAUIACAZGNM-UHFFFAOYSA-N 0.000 description 1
- QGSNSASDNIDAHV-UHFFFAOYSA-N methyl 3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-[3-(trifluoromethoxy)phenyl]propanoate Chemical compound C=1C=CC(OC(F)(F)F)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCNC1=CC(C)=CC=N1 QGSNSASDNIDAHV-UHFFFAOYSA-N 0.000 description 1
- DNKXIHDCFHQJIP-UHFFFAOYSA-N methyl 3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]-3-[4-[4-(trifluoromethyl)phenyl]phenyl]propanoate Chemical compound C=1C=C(C=2C=CC(=CC=2)C(F)(F)F)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 DNKXIHDCFHQJIP-UHFFFAOYSA-N 0.000 description 1
- VHVHIUPUHHFXRW-UHFFFAOYSA-N methyl 3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-(2-nitrophenyl)propanoate Chemical compound C=1C=CC=C([N+]([O-])=O)C=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC(C)=CC=N1 VHVHIUPUHHFXRW-UHFFFAOYSA-N 0.000 description 1
- HXNPPMNMLSZLLZ-UHFFFAOYSA-N methyl 3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-(3-nitrophenyl)propanoate Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC(C)=CC=N1 HXNPPMNMLSZLLZ-UHFFFAOYSA-N 0.000 description 1
- PNZGDGYVUFAMIG-UHFFFAOYSA-N methyl 3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-(4-naphthalen-2-ylphenyl)propanoate Chemical compound C=1C=C(C=2C=C3C=CC=CC3=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC(C)=CC=N1 PNZGDGYVUFAMIG-UHFFFAOYSA-N 0.000 description 1
- CGXMQXKKDBRUMR-UHFFFAOYSA-N methyl 3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-(4-phenylphenyl)propanoate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC(C)=CC=N1 CGXMQXKKDBRUMR-UHFFFAOYSA-N 0.000 description 1
- KPHTWQRIPDANPN-UHFFFAOYSA-N methyl 3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-(4-phenylphenyl)propanoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC(C)=CC=N1 KPHTWQRIPDANPN-UHFFFAOYSA-N 0.000 description 1
- LNIMVMBWHRKFIC-UHFFFAOYSA-N methyl 3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-[4-(trifluoromethoxy)phenyl]propanoate Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCNC1=CC(C)=CC=N1 LNIMVMBWHRKFIC-UHFFFAOYSA-N 0.000 description 1
- KCYHNNMTMGSSIA-UHFFFAOYSA-N methyl 3-[[2-[6-[(4-methylpyridin-2-yl)amino]hexanoylamino]acetyl]amino]-3-(3-nitrophenyl)propanoate Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCCNC1=CC(C)=CC=N1 KCYHNNMTMGSSIA-UHFFFAOYSA-N 0.000 description 1
- SUPMFMMJRXYOFI-UHFFFAOYSA-N methyl 3-[[2-[7-[(4-methylpyridin-2-yl)amino]heptanoylamino]acetyl]amino]-3-(3-nitrophenyl)propanoate Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(CC(=O)OC)NC(=O)CNC(=O)CCCCCCNC1=CC(C)=CC=N1 SUPMFMMJRXYOFI-UHFFFAOYSA-N 0.000 description 1
- WCYSVIMUYDWOPM-UHFFFAOYSA-N methyl 3-amino-3-(3-nitrophenyl)propanoate Chemical compound COC(=O)CC(N)C1=CC=CC([N+]([O-])=O)=C1 WCYSVIMUYDWOPM-UHFFFAOYSA-N 0.000 description 1
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
- OJVSEHLMRCLAFY-UHFFFAOYSA-N methyl propanoate;hydrochloride Chemical compound Cl.CCC(=O)OC OJVSEHLMRCLAFY-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 150000004250 monothioacetals Chemical class 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000001491 myopia Diseases 0.000 description 1
- 230000004379 myopia Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
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- ZGHKOLNGLRJTFT-UHFFFAOYSA-M sodium;3-(2-hydroxy-3-nitrophenyl)-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C(=C(C=CC=2)[N+]([O-])=O)O)=C1 ZGHKOLNGLRJTFT-UHFFFAOYSA-M 0.000 description 1
- ZTFAAVJKGVXFBY-UHFFFAOYSA-M sodium;3-(2-hydroxy-3-phenylphenyl)-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C(=C(C=CC=2)C=2C=CC=CC=2)O)=C1 ZTFAAVJKGVXFBY-UHFFFAOYSA-M 0.000 description 1
- SHFZAYIXLDBLMG-UHFFFAOYSA-M sodium;3-(2-hydroxy-4-naphthalen-1-ylphenyl)-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].OC1=CC(C=2C3=CC=CC=C3C=CC=2)=CC=C1C(CC([O-])=O)NC(=O)CNC(=O)CCCNC1=CC=CC=N1 SHFZAYIXLDBLMG-UHFFFAOYSA-M 0.000 description 1
- NTIBRWDDIWXKJW-UHFFFAOYSA-M sodium;3-(2-hydroxy-4-naphthalen-1-ylphenyl)-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C(=CC(=CC=2)C=2C3=CC=CC=C3C=CC=2)O)=C1 NTIBRWDDIWXKJW-UHFFFAOYSA-M 0.000 description 1
- AHDLDKXLMAPRTE-UHFFFAOYSA-M sodium;3-(2-nitrophenyl)-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=CC=C([N+]([O-])=O)C=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCNC1=CC=CC=N1 AHDLDKXLMAPRTE-UHFFFAOYSA-M 0.000 description 1
- FOVMTAXYJJZDDT-UHFFFAOYSA-M sodium;3-(2-nitrophenyl)-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=CC=C([N+]([O-])=O)C=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 FOVMTAXYJJZDDT-UHFFFAOYSA-M 0.000 description 1
- GGQUTOOFLHJDKS-UHFFFAOYSA-M sodium;3-(3-hydroxy-4-phenylphenyl)-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].OC1=CC(C(CC([O-])=O)NC(=O)CNC(=O)CCCNC=2N=CC=CC=2)=CC=C1C1=CC=CC=C1 GGQUTOOFLHJDKS-UHFFFAOYSA-M 0.000 description 1
- KCPJSFFBPXUJMN-UHFFFAOYSA-M sodium;3-(3-nitrophenyl)-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=CC([N+]([O-])=O)=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCNC1=CC=CC=N1 KCPJSFFBPXUJMN-UHFFFAOYSA-M 0.000 description 1
- JSSXHDDOLJGSCO-UHFFFAOYSA-M sodium;3-(4-chloro-3-nitrophenyl)-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 JSSXHDDOLJGSCO-UHFFFAOYSA-M 0.000 description 1
- GMBUMNNYRIIOAK-UHFFFAOYSA-M sodium;3-(4-chloro-3-nitrophenyl)-3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 GMBUMNNYRIIOAK-UHFFFAOYSA-M 0.000 description 1
- HULOTBODQASEQM-UHFFFAOYSA-M sodium;3-(4-chloro-3-nitrophenyl)-3-[[2-[6-[(4-methylpyridin-2-yl)amino]hexanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 HULOTBODQASEQM-UHFFFAOYSA-M 0.000 description 1
- PXXSYQLFQQQLIL-UHFFFAOYSA-M sodium;3-(4-methyl-3-nitrophenyl)-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C)=CC=C1C(CC([O-])=O)NC(=O)CNC(=O)CCCNC1=CC=CC=N1 PXXSYQLFQQQLIL-UHFFFAOYSA-M 0.000 description 1
- IKXDQMOQBGUDRG-UHFFFAOYSA-M sodium;3-(4-methyl-3-nitrophenyl)-3-[[2-[4-(pyrimidin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C)=CC=C1C(CC([O-])=O)NC(=O)CNC(=O)CCCNC1=NC=CC=N1 IKXDQMOQBGUDRG-UHFFFAOYSA-M 0.000 description 1
- YRRGDCLETADDSZ-UHFFFAOYSA-M sodium;3-(4-methyl-3-nitrophenyl)-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C(C)=CC=2)[N+]([O-])=O)=C1 YRRGDCLETADDSZ-UHFFFAOYSA-M 0.000 description 1
- OVUBRDFFUVZOEC-UHFFFAOYSA-M sodium;3-(4-methyl-3-nitrophenyl)-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C)=CC=C1C(CC([O-])=O)NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 OVUBRDFFUVZOEC-UHFFFAOYSA-M 0.000 description 1
- GFPPNYUWNWBELX-UHFFFAOYSA-M sodium;3-(4-methyl-3-nitrophenyl)-3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C(C)=CC=2)[N+]([O-])=O)=C1 GFPPNYUWNWBELX-UHFFFAOYSA-M 0.000 description 1
- NOMUEIYDBJTJQL-UHFFFAOYSA-M sodium;3-(4-methyl-3-nitrophenyl)-3-[[2-[5-[(6-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=CC(NCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C(C)=CC=2)[N+]([O-])=O)=N1 NOMUEIYDBJTJQL-UHFFFAOYSA-M 0.000 description 1
- KTOQHVMKDPAEQZ-UHFFFAOYSA-M sodium;3-(4-methyl-3-nitrophenyl)-3-[[2-[6-[(4-methylpyridin-2-yl)amino]hexanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C(C)=CC=2)[N+]([O-])=O)=C1 KTOQHVMKDPAEQZ-UHFFFAOYSA-M 0.000 description 1
- XXMDKMHAEBXWGA-UHFFFAOYSA-M sodium;3-(4-naphthalen-1-ylphenyl)-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C3=CC=CC=C3C=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCNC1=CC=CC=N1 XXMDKMHAEBXWGA-UHFFFAOYSA-M 0.000 description 1
- WGVVGVBMWDGHOL-UHFFFAOYSA-M sodium;3-(4-naphthalen-1-ylphenyl)-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C3=CC=CC=C3C=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 WGVVGVBMWDGHOL-UHFFFAOYSA-M 0.000 description 1
- ZMNJRCFQQRFGRP-UHFFFAOYSA-M sodium;3-(4-naphthalen-2-ylphenyl)-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C=C3C=CC=CC3=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 ZMNJRCFQQRFGRP-UHFFFAOYSA-M 0.000 description 1
- JTZMXMAIDOUOQJ-UHFFFAOYSA-M sodium;3-(4-phenylphenyl)-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCNC1=CC=CC=N1 JTZMXMAIDOUOQJ-UHFFFAOYSA-M 0.000 description 1
- XAQDYEKRUSJKMD-UHFFFAOYSA-M sodium;3-(4-phenylphenyl)-3-[[2-[4-(pyrimidin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCNC1=NC=CC=N1 XAQDYEKRUSJKMD-UHFFFAOYSA-M 0.000 description 1
- BYBHKNOTIFRHFM-UHFFFAOYSA-M sodium;3-(4-phenylphenyl)-3-[[2-[5-(pyrimidin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=NC=CC=N1 BYBHKNOTIFRHFM-UHFFFAOYSA-M 0.000 description 1
- OIEHVRPCRHGIPN-UHFFFAOYSA-M sodium;3-(5-bromo-2-hydroxy-3-nitrophenyl)-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C(=C(C=C(Br)C=2)[N+]([O-])=O)O)=C1 OIEHVRPCRHGIPN-UHFFFAOYSA-M 0.000 description 1
- XHHWXESWLNCSMI-UHFFFAOYSA-M sodium;3-[3-(4-fluoro-2-hydroxyphenyl)phenyl]-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C=CC=2)C=2C(=CC(F)=CC=2)O)=C1 XHHWXESWLNCSMI-UHFFFAOYSA-M 0.000 description 1
- FBEZOILHGVRHJS-UHFFFAOYSA-M sodium;3-[3-(4-fluorophenyl)phenyl]-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=CC(C=2C=CC(F)=CC=2)=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCNC1=CC=CC=N1 FBEZOILHGVRHJS-UHFFFAOYSA-M 0.000 description 1
- HPRXXHFCAGASRG-UHFFFAOYSA-M sodium;3-[3-(4-fluorophenyl)phenyl]-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C=CC=2)C=2C=CC(F)=CC=2)=C1 HPRXXHFCAGASRG-UHFFFAOYSA-M 0.000 description 1
- HMTWUEPTRHYGRZ-UHFFFAOYSA-M sodium;3-[3-(4-fluorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=CC(C=2C=CC(F)=CC=2)=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 HMTWUEPTRHYGRZ-UHFFFAOYSA-M 0.000 description 1
- IUIUDENPRDFLPE-UHFFFAOYSA-M sodium;3-[4-(2-fluorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C(=CC=CC=2)F)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 IUIUDENPRDFLPE-UHFFFAOYSA-M 0.000 description 1
- DWAJEDKDLXYBRK-UHFFFAOYSA-M sodium;3-[4-(3-chloro-4-fluorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C=C(Cl)C(F)=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 DWAJEDKDLXYBRK-UHFFFAOYSA-M 0.000 description 1
- XSJADWBSPFRREV-UHFFFAOYSA-M sodium;3-[4-(3-chlorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C=C(Cl)C=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 XSJADWBSPFRREV-UHFFFAOYSA-M 0.000 description 1
- WVEMOVYXOIKJOJ-UHFFFAOYSA-M sodium;3-[4-(3-fluorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C=C(F)C=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 WVEMOVYXOIKJOJ-UHFFFAOYSA-M 0.000 description 1
- HYJQCVQRFICAFY-UHFFFAOYSA-M sodium;3-[4-(4-chlorophenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 HYJQCVQRFICAFY-UHFFFAOYSA-M 0.000 description 1
- JUBZYUAOLRAUHH-UHFFFAOYSA-M sodium;3-[4-(4-fluoro-2-hydroxyphenyl)phenyl]-3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=CC(=CC=2)C=2C(=CC(F)=CC=2)O)=C1 JUBZYUAOLRAUHH-UHFFFAOYSA-M 0.000 description 1
- SHBDWZSATBLHGF-UHFFFAOYSA-M sodium;3-[4-(4-fluorophenyl)-3-hydroxyphenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].OC1=CC(C(CC([O-])=O)NC(=O)CNC(=O)CCCCNC=2N=CC=CC=2)=CC=C1C1=CC=C(F)C=C1 SHBDWZSATBLHGF-UHFFFAOYSA-M 0.000 description 1
- LKOBPVDYNNLOMC-UHFFFAOYSA-M sodium;3-[4-(4-fluorophenyl)phenyl]-3-[[2-[4-(pyridin-2-ylamino)butanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C=1C=C(C=2C=CC(F)=CC=2)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCNC1=CC=CC=N1 LKOBPVDYNNLOMC-UHFFFAOYSA-M 0.000 description 1
- BZAPCUFXNXPALU-UHFFFAOYSA-M sodium;3-[4-(4-methylphenyl)phenyl]-3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoate Chemical compound [Na+].C1=CC(C)=CC=C1C1=CC=C(C(CC([O-])=O)NC(=O)CNC(=O)CCCCNC=2N=CC=CC=2)C=C1 BZAPCUFXNXPALU-UHFFFAOYSA-M 0.000 description 1
- JGEDDEPQDDYBGK-UHFFFAOYSA-M sodium;3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(3-nitrophenyl)propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 JGEDDEPQDDYBGK-UHFFFAOYSA-M 0.000 description 1
- DNGIMJFCTVZMAR-UHFFFAOYSA-M sodium;3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(4-naphthalen-1-ylphenyl)propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=CC(=CC=2)C=2C3=CC=CC=C3C=CC=2)=C1 DNGIMJFCTVZMAR-UHFFFAOYSA-M 0.000 description 1
- MDIYDSDXYIIHIU-UHFFFAOYSA-M sodium;3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(4-naphthalen-2-ylphenyl)propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=CC(=CC=2)C=2C=C3C=CC=CC3=CC=2)=C1 MDIYDSDXYIIHIU-UHFFFAOYSA-M 0.000 description 1
- CRNVQEOJZNSJBY-UHFFFAOYSA-M sodium;3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(4-nitrophenyl)propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 CRNVQEOJZNSJBY-UHFFFAOYSA-M 0.000 description 1
- UJVLEVQNKZMTFP-UHFFFAOYSA-M sodium;3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(4-phenylphenyl)propanoate Chemical compound [Na+].CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 UJVLEVQNKZMTFP-UHFFFAOYSA-M 0.000 description 1
- FWXSCXRVHGPXHE-UHFFFAOYSA-M sodium;3-[[2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]-3-[4-[4-(trifluoromethyl)phenyl]phenyl]propanoate Chemical compound [Na+].C=1C=C(C=2C=CC(=CC=2)C(F)(F)F)C=CC=1C(CC(=O)[O-])NC(=O)CNC(=O)CCCCNC1=CC=CC=N1 FWXSCXRVHGPXHE-UHFFFAOYSA-M 0.000 description 1
- SNEHRIUVQOWVAF-UHFFFAOYSA-M sodium;3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-(2-nitrophenyl)propanoate Chemical compound [Na+].CC1=CC=NC(NCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C(=CC=CC=2)[N+]([O-])=O)=C1 SNEHRIUVQOWVAF-UHFFFAOYSA-M 0.000 description 1
- SJXPOEVTSWNVQK-UHFFFAOYSA-M sodium;3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-(3-nitrophenyl)propanoate Chemical compound [Na+].CC1=CC=NC(NCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 SJXPOEVTSWNVQK-UHFFFAOYSA-M 0.000 description 1
- YHAAHNCDFVETEF-UHFFFAOYSA-M sodium;3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-(4-naphthalen-2-ylphenyl)propanoate Chemical compound [Na+].CC1=CC=NC(NCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=CC(=CC=2)C=2C=C3C=CC=CC3=CC=2)=C1 YHAAHNCDFVETEF-UHFFFAOYSA-M 0.000 description 1
- JGHVQLGEDMJFOT-UHFFFAOYSA-M sodium;3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-(4-phenylphenyl)propanoate Chemical compound [Na+].CC1=CC=NC(NCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 JGHVQLGEDMJFOT-UHFFFAOYSA-M 0.000 description 1
- LMRZAFMNMDTTTK-UHFFFAOYSA-M sodium;3-[[2-[5-[(4-methylpyridin-2-yl)amino]pentanoylamino]acetyl]amino]-3-[3-(trifluoromethoxy)phenyl]propanoate Chemical compound [Na+].CC1=CC=NC(NCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(OC(F)(F)F)C=CC=2)=C1 LMRZAFMNMDTTTK-UHFFFAOYSA-M 0.000 description 1
- IRJIEVUUHSWMDO-UHFFFAOYSA-M sodium;3-[[2-[6-[(4-methylpyridin-2-yl)amino]hexanoylamino]acetyl]amino]-3-(3-nitrophenyl)propanoate Chemical compound [Na+].CC1=CC=NC(NCCCCCC(=O)NCC(=O)NC(CC([O-])=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 IRJIEVUUHSWMDO-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- WVJYSMADLINZRV-UHFFFAOYSA-N tert-butyl 3-[[2-[4-[(4-methylpyridin-2-yl)amino]butanoylamino]acetyl]amino]-3-(3-nitrophenyl)propanoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=NC(NCCCC(=O)NCC(=O)NC(CC(=O)OC(C)(C)C)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 WVJYSMADLINZRV-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 108091006106 transcriptional activators Proteins 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 210000005167 vascular cell Anatomy 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23908799A | 1999-01-27 | 1999-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0105477A2 true HUP0105477A2 (hu) | 2002-05-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0105477A HUP0105477A2 (hu) | 1999-01-27 | 2000-01-27 | Metalloproteináz mátrixok reverz hidroxamát inhibitorai és alkalmazásuk gyógyszerkészítmények előállítására |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US20020007060A1 (enExample) |
| EP (1) | EP1147101B1 (enExample) |
| JP (1) | JP4718686B2 (enExample) |
| KR (1) | KR100748010B1 (enExample) |
| CN (1) | CN1222519C (enExample) |
| AR (1) | AR029329A1 (enExample) |
| AT (1) | ATE228122T1 (enExample) |
| AU (1) | AU764383B2 (enExample) |
| BG (1) | BG105782A (enExample) |
| BR (1) | BR0007278A (enExample) |
| CA (1) | CA2358951C (enExample) |
| CO (1) | CO5150194A1 (enExample) |
| CZ (1) | CZ20012591A3 (enExample) |
| DE (1) | DE60000819T2 (enExample) |
| DK (1) | DK1147101T3 (enExample) |
| ES (1) | ES2187443T3 (enExample) |
| HK (1) | HK1043115A1 (enExample) |
| HU (1) | HUP0105477A2 (enExample) |
| IL (1) | IL143713A0 (enExample) |
| NO (1) | NO20013669L (enExample) |
| NZ (1) | NZ512372A (enExample) |
| PL (1) | PL349771A1 (enExample) |
| PT (1) | PT1147101E (enExample) |
| SK (1) | SK10582001A3 (enExample) |
| TR (1) | TR200102159T2 (enExample) |
| TW (1) | TWI225486B (enExample) |
| WO (1) | WO2000044739A1 (enExample) |
| ZA (1) | ZA200104979B (enExample) |
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| GB9923078D0 (en) * | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| AU2001298065A1 (en) * | 2001-01-12 | 2003-09-02 | Abbott Laboratories | Process for the preparation of matrix metalloproteinase inhibitors |
| EP1431285B1 (en) | 2001-09-07 | 2009-01-07 | Kaken Pharmaceutical Co., Ltd. | Reverse hydroxamic acid derivatives |
| EP1896404B1 (en) * | 2005-06-27 | 2014-09-17 | Nabriva Therapeutics AG | Pleuromutilin derivatives containing a hydroxyamino- or acyloxyaminocycloalkyl group |
| US20110015158A1 (en) | 2007-12-11 | 2011-01-20 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
| WO2015107139A1 (en) | 2014-01-17 | 2015-07-23 | Proyecto De Biomedicina Cima, S.L. | Compounds for use as antifibrinolytic agents |
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| EP0780386B1 (en) * | 1995-12-20 | 2002-10-02 | F. Hoffmann-La Roche Ag | Matrix metalloprotease inhibitors |
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2000
- 2000-01-25 CO CO00003867A patent/CO5150194A1/es unknown
- 2000-01-26 AR ARP000100349A patent/AR029329A1/es not_active Application Discontinuation
- 2000-01-27 ES ES00905758T patent/ES2187443T3/es not_active Expired - Lifetime
- 2000-01-27 SK SK1058-2001A patent/SK10582001A3/sk unknown
- 2000-01-27 WO PCT/US2000/002038 patent/WO2000044739A1/en not_active Ceased
- 2000-01-27 CZ CZ20012591A patent/CZ20012591A3/cs unknown
- 2000-01-27 TR TR2001/02159T patent/TR200102159T2/xx unknown
- 2000-01-27 PT PT00905758T patent/PT1147101E/pt unknown
- 2000-01-27 NZ NZ512372A patent/NZ512372A/xx unknown
- 2000-01-27 AU AU27391/00A patent/AU764383B2/en not_active Ceased
- 2000-01-27 EP EP00905758A patent/EP1147101B1/en not_active Expired - Lifetime
- 2000-01-27 HK HK02102947.8A patent/HK1043115A1/zh unknown
- 2000-01-27 CA CA002358951A patent/CA2358951C/en not_active Expired - Fee Related
- 2000-01-27 CN CNB008032378A patent/CN1222519C/zh not_active Expired - Fee Related
- 2000-01-27 JP JP2000595995A patent/JP4718686B2/ja not_active Expired - Fee Related
- 2000-01-27 DK DK00905758T patent/DK1147101T3/da active
- 2000-01-27 HU HU0105477A patent/HUP0105477A2/hu unknown
- 2000-01-27 IL IL14371300A patent/IL143713A0/xx unknown
- 2000-01-27 KR KR1020017009393A patent/KR100748010B1/ko not_active Expired - Fee Related
- 2000-01-27 PL PL00349771A patent/PL349771A1/xx not_active Application Discontinuation
- 2000-01-27 DE DE60000819T patent/DE60000819T2/de not_active Expired - Lifetime
- 2000-01-27 AT AT00905758T patent/ATE228122T1/de not_active IP Right Cessation
- 2000-01-27 BR BR0007278-8A patent/BR0007278A/pt not_active Application Discontinuation
- 2000-02-25 TW TW089101383A patent/TWI225486B/zh not_active IP Right Cessation
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2001
- 2001-06-18 ZA ZA200104979A patent/ZA200104979B/en unknown
- 2001-07-16 US US09/905,242 patent/US20020007060A1/en not_active Abandoned
- 2001-07-26 NO NO20013669A patent/NO20013669L/no not_active Application Discontinuation
- 2001-08-03 BG BG105782A patent/BG105782A/xx unknown
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Legal Events
| Date | Code | Title | Description |
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| FD9A | Lapse of provisional protection due to non-payment of fees |