JP2005529180A5 - - Google Patents
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- Publication number
- JP2005529180A5 JP2005529180A5 JP2004513236A JP2004513236A JP2005529180A5 JP 2005529180 A5 JP2005529180 A5 JP 2005529180A5 JP 2004513236 A JP2004513236 A JP 2004513236A JP 2004513236 A JP2004513236 A JP 2004513236A JP 2005529180 A5 JP2005529180 A5 JP 2005529180A5
- Authority
- JP
- Japan
- Prior art keywords
- naphthoyl
- phenylalanine
- aryl
- alkyl
- substituted
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 30
- -1 hydroxy, amino Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 26
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 239000003814 drug Substances 0.000 claims 12
- 230000002265 prevention Effects 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical class C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 108091006335 Prostaglandin I receptors Proteins 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 239000002464 receptor antagonist Substances 0.000 claims 6
- 229940044551 receptor antagonist Drugs 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 241001465754 Metazoa Species 0.000 claims 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 208000014001 urinary system disease Diseases 0.000 claims 4
- 208000031220 Hemophilia Diseases 0.000 claims 3
- 208000009292 Hemophilia A Diseases 0.000 claims 3
- 208000032843 Hemorrhage Diseases 0.000 claims 3
- 208000001953 Hypotension Diseases 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 208000034158 bleeding Diseases 0.000 claims 3
- 230000000740 bleeding effect Effects 0.000 claims 3
- 230000036543 hypotension Effects 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- BUHUSYHVRVAOGE-SANMLTNESA-N (2S)-3-(4-hydroxyphenyl)-2-[methyl-(6-phenylmethoxynaphthalene-2-carbonyl)oxyamino]propanoic acid Chemical compound C(C1=CC=CC=C1)OC=1C=C2C=CC(=CC2=CC=1)C(=O)ON([C@@H](CC1=CC=C(C=C1)O)C(=O)O)C BUHUSYHVRVAOGE-SANMLTNESA-N 0.000 claims 1
- YTORALQOHQBKLD-VWLOTQADSA-N (2s)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]-3-[3-(trifluoromethyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=CC(C(F)(F)F)=C1 YTORALQOHQBKLD-VWLOTQADSA-N 0.000 claims 1
- FEEQKVHOBXISEA-VWLOTQADSA-N (2s)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]-3-[4-(trifluoromethyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=C(C(F)(F)F)C=C1 FEEQKVHOBXISEA-VWLOTQADSA-N 0.000 claims 1
- JUZSLGLIOKYLRR-DEOSSOPVSA-N (2s)-2-[[6-[(2,3-dichlorophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C(=C(Cl)C=CC=3)Cl)=CC2=CC=1)C1=CC=CC=C1 JUZSLGLIOKYLRR-DEOSSOPVSA-N 0.000 claims 1
- YRJJGRFTKMSZFX-VWLOTQADSA-N (2s)-2-[[6-[(2-bromophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C(=CC=CC=3)Br)=CC2=CC=1)C1=CC=CC=C1 YRJJGRFTKMSZFX-VWLOTQADSA-N 0.000 claims 1
- CQNXPOBQDKDAPX-VWLOTQADSA-N (2s)-2-[[6-[(2-chlorophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C(=CC=CC=3)Cl)=CC2=CC=1)C1=CC=CC=C1 CQNXPOBQDKDAPX-VWLOTQADSA-N 0.000 claims 1
- FIIPDONVDRHDOP-VWLOTQADSA-N (2s)-2-[[6-[(2-fluorophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C(=CC=CC=3)F)=CC2=CC=1)C1=CC=CC=C1 FIIPDONVDRHDOP-VWLOTQADSA-N 0.000 claims 1
- NDMWOLQBUGJNOJ-VWLOTQADSA-N (2s)-2-[[6-[(2-methoxyphenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound COC1=CC=CC=C1COC1=CC=C(C=C(C=C2)C(=O)N[C@@H](CC=3C=CC=CC=3)C(O)=O)C2=C1 NDMWOLQBUGJNOJ-VWLOTQADSA-N 0.000 claims 1
- HZPCJFLXEZXILW-SANMLTNESA-N (2s)-2-[[6-[(2-methylphenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound CC1=CC=CC=C1COC1=CC=C(C=C(C=C2)C(=O)N[C@@H](CC=3C=CC=CC=3)C(O)=O)C2=C1 HZPCJFLXEZXILW-SANMLTNESA-N 0.000 claims 1
- GSZVZJQVUZHDMQ-VWLOTQADSA-N (2s)-2-[[6-[(3,4-difluorophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=C(F)C(F)=CC=3)=CC2=CC=1)C1=CC=CC=C1 GSZVZJQVUZHDMQ-VWLOTQADSA-N 0.000 claims 1
- PIJJEXAHJYGQEH-VWLOTQADSA-N (2s)-2-[[6-[(3,5-dichlorophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=C(Cl)C=C(Cl)C=3)=CC2=CC=1)C1=CC=CC=C1 PIJJEXAHJYGQEH-VWLOTQADSA-N 0.000 claims 1
- LYESCKDBXYIXTA-MHZLTWQESA-N (2s)-2-[[6-[(3,5-dimethoxyphenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound COC1=CC(OC)=CC(COC=2C=C3C=CC(=CC3=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)=C1 LYESCKDBXYIXTA-MHZLTWQESA-N 0.000 claims 1
- IMACPGAIZDCBAX-VWLOTQADSA-N (2s)-2-[[6-[(3-bromophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=C(Br)C=CC=3)=CC2=CC=1)C1=CC=CC=C1 IMACPGAIZDCBAX-VWLOTQADSA-N 0.000 claims 1
- TUUOKJHZBYYXCA-VWLOTQADSA-N (2s)-2-[[6-[(3-chlorophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=C(Cl)C=CC=3)=CC2=CC=1)C1=CC=CC=C1 TUUOKJHZBYYXCA-VWLOTQADSA-N 0.000 claims 1
- IKKLSGXYXFHLRY-MHZLTWQESA-N (2s)-2-[[6-[(3-ethoxyphenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound CCOC1=CC=CC(COC=2C=C3C=CC(=CC3=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)=C1 IKKLSGXYXFHLRY-MHZLTWQESA-N 0.000 claims 1
- VWNCUHBPKPFXLU-VWLOTQADSA-N (2s)-2-[[6-[(3-fluorophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=C(F)C=CC=3)=CC2=CC=1)C1=CC=CC=C1 VWNCUHBPKPFXLU-VWLOTQADSA-N 0.000 claims 1
- CCDBMEARNCXPRZ-SANMLTNESA-N (2s)-2-[[6-[(3-methoxyphenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound COC1=CC=CC(COC=2C=C3C=CC(=CC3=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)=C1 CCDBMEARNCXPRZ-SANMLTNESA-N 0.000 claims 1
- CGOZGVCTZMCIJM-SANMLTNESA-N (2s)-2-[[6-[(3-methylphenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound CC1=CC=CC(COC=2C=C3C=CC(=CC3=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)=C1 CGOZGVCTZMCIJM-SANMLTNESA-N 0.000 claims 1
- MECDMTZYFIVTIY-VWLOTQADSA-N (2s)-2-[[6-[(3-nitrophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=C(C=CC=3)[N+]([O-])=O)=CC2=CC=1)C1=CC=CC=C1 MECDMTZYFIVTIY-VWLOTQADSA-N 0.000 claims 1
- CFMKLTVMOUBFCX-VWLOTQADSA-N (2s)-2-[[6-[(4-fluorophenyl)methoxy]naphthalene-2-carbonyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC(F)=CC=3)=CC2=CC=1)C1=CC=CC=C1 CFMKLTVMOUBFCX-VWLOTQADSA-N 0.000 claims 1
- SQVFFVMPPQLWJC-VWLOTQADSA-N (2s)-3-(2-fluorophenyl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=CC=C1F SQVFFVMPPQLWJC-VWLOTQADSA-N 0.000 claims 1
- MLRHCNKXXXZKQK-VWLOTQADSA-N (2s)-3-(3-fluorophenyl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=CC(F)=C1 MLRHCNKXXXZKQK-VWLOTQADSA-N 0.000 claims 1
- TWTCEUGQFPSLEC-VWLOTQADSA-N (2s)-3-(3-hydroxyphenyl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=CC(O)=C1 TWTCEUGQFPSLEC-VWLOTQADSA-N 0.000 claims 1
- PQWGNXROACCQPF-VWLOTQADSA-N (2s)-3-(4-bromophenyl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=C(Br)C=C1 PQWGNXROACCQPF-VWLOTQADSA-N 0.000 claims 1
- FAGVBFPPQBUBSB-VWLOTQADSA-N (2s)-3-(4-chlorophenyl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=C(Cl)C=C1 FAGVBFPPQBUBSB-VWLOTQADSA-N 0.000 claims 1
- IVOVPEZNMIAURR-DEOSSOPVSA-N (2s)-3-(4-hydroxy-3-methoxyphenyl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound C1=C(O)C(OC)=CC(C[C@H](NC(=O)C=2C=C3C=CC(OCC=4C=CC=CC=4)=CC3=CC=2)C(O)=O)=C1 IVOVPEZNMIAURR-DEOSSOPVSA-N 0.000 claims 1
- LPQLBDJBZRPRMM-VWLOTQADSA-N (2s)-3-(4-iodophenyl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=C(I)C=C1 LPQLBDJBZRPRMM-VWLOTQADSA-N 0.000 claims 1
- MVYCNGPCMKBZPB-VWLOTQADSA-N (2s)-3-(4-nitrophenyl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=C([N+]([O-])=O)C=C1 MVYCNGPCMKBZPB-VWLOTQADSA-N 0.000 claims 1
- XGOIIFMCHYBVEG-MHZLTWQESA-N (2s)-3-(5-fluoro-1h-indol-3-yl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound N([C@@H](CC=1C2=CC(F)=CC=C2NC=1)C(=O)O)C(=O)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=CC=C1 XGOIIFMCHYBVEG-MHZLTWQESA-N 0.000 claims 1
- YCQQEIMVQKRBCA-MHZLTWQESA-N (2s)-3-(5-hydroxy-1h-indol-3-yl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound N([C@@H](CC=1C2=CC(O)=CC=C2NC=1)C(=O)O)C(=O)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=CC=C1 YCQQEIMVQKRBCA-MHZLTWQESA-N 0.000 claims 1
- FMKUOTFTXJGBLH-SKCDSABHSA-N (2s)-3-hydroxy-3-phenyl-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound N([C@@H](C(O)C=1C=CC=CC=1)C(O)=O)C(=O)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=CC=C1 FMKUOTFTXJGBLH-SKCDSABHSA-N 0.000 claims 1
- ZXHMHVLLLYJHCA-VWLOTQADSA-N (2s)-3-phenyl-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=CC=C1 ZXHMHVLLLYJHCA-VWLOTQADSA-N 0.000 claims 1
- ZLGXZBDNOOKPFE-SANMLTNESA-N (2s)-3-phenyl-2-[[6-(2-phenylethoxy)naphthalene-2-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCCC=3C=CC=CC=3)=CC2=CC=1)C1=CC=CC=C1 ZLGXZBDNOOKPFE-SANMLTNESA-N 0.000 claims 1
- HJAFLBHHGUZWRV-OHMHCFLMSA-N (2s)-3-phenyl-2-[[6-(2-phenylpropoxy)naphthalene-2-carbonyl]amino]propanoic acid Chemical compound C([C@H](NC(=O)C1=CC2=CC=C(C=C2C=C1)OCC(C)C=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 HJAFLBHHGUZWRV-OHMHCFLMSA-N 0.000 claims 1
- AOSJDEUJANOATM-VWLOTQADSA-N (2s)-3-phenyl-2-[[6-(2-pyridin-4-ylethoxy)naphthalene-2-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCCC=3C=CN=CC=3)=CC2=CC=1)C1=CC=CC=C1 AOSJDEUJANOATM-VWLOTQADSA-N 0.000 claims 1
- ZLKIGNWQBDCHJL-DEOSSOPVSA-N (2s)-3-phenyl-2-[[6-(2-pyrrol-1-ylethoxy)naphthalene-2-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCCN3C=CC=C3)=CC2=CC=1)C1=CC=CC=C1 ZLKIGNWQBDCHJL-DEOSSOPVSA-N 0.000 claims 1
- RBADCINDQXFTRB-DEOSSOPVSA-N (2s)-3-phenyl-2-[[6-(pyridin-3-ylmethoxy)naphthalene-2-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=NC=CC=3)=CC2=CC=1)C1=CC=CC=C1 RBADCINDQXFTRB-DEOSSOPVSA-N 0.000 claims 1
- VOJXBFUXBWLQQV-DEOSSOPVSA-N (2s)-3-phenyl-2-[[6-(pyridin-4-ylmethoxy)naphthalene-2-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=C2C=CC(OCC=3C=CN=CC=3)=CC2=CC=1)C1=CC=CC=C1 VOJXBFUXBWLQQV-DEOSSOPVSA-N 0.000 claims 1
- VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 claims 1
- ZTXWIKHKNGFJAX-UHFFFAOYSA-N 1-hydroxynaphthalene-2-carboxamide Chemical class C1=CC=CC2=C(O)C(C(=O)N)=CC=C21 ZTXWIKHKNGFJAX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0213488A GB2389580A (en) | 2002-06-12 | 2002-06-12 | 2-Naphthamide PGI2 antagonists |
| PCT/EP2003/005705 WO2003106402A1 (en) | 2002-06-12 | 2003-05-30 | 2-naphtamide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005529180A JP2005529180A (ja) | 2005-09-29 |
| JP2005529180A5 true JP2005529180A5 (enExample) | 2006-07-13 |
Family
ID=9938442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004513236A Pending JP2005529180A (ja) | 2002-06-12 | 2003-05-30 | ２−ナフトアミド誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20060166989A1 (enExample) |
| EP (1) | EP1515941A1 (enExample) |
| JP (1) | JP2005529180A (enExample) |
| AU (1) | AU2003238180A1 (enExample) |
| CA (1) | CA2489286A1 (enExample) |
| GB (1) | GB2389580A (enExample) |
| WO (1) | WO2003106402A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1676834A1 (en) * | 2004-12-30 | 2006-07-05 | Sanofi-Aventis Deutschland GmbH | Fused bicyclic carboxamide derivates for use as CXCR2 inhibitors in the treatment of inflammation |
| US8607543B2 (en) | 2006-05-19 | 2013-12-17 | Bae Systems Plc | Millimetre-scale engine |
| US7964732B2 (en) | 2006-11-17 | 2011-06-21 | Pfizer Inc. | Substituted bicyclocarboxyamide compounds |
| WO2014086701A1 (en) * | 2012-12-06 | 2014-06-12 | F. Hoffmann-La Roche Ag | Substituted thiazole compounds |
| WO2014114603A1 (en) * | 2013-01-24 | 2014-07-31 | F. Hoffmann-La Roche Ag | Substituted thiazole compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5753700A (en) * | 1994-12-28 | 1998-05-19 | Ono Pharmaceutical Co., Ltd. | Naphthyloxyacetic acid derivatives |
| WO2000031045A1 (en) * | 1998-11-20 | 2000-06-02 | Torii Pharmaceutical Co., Ltd. | Naphthalene derivatives |
| DK1163208T3 (da) * | 1999-08-06 | 2004-08-16 | Vertex Pharma | Caspaseinhibitorer og anvendelser deraf |
| EP1265853A1 (en) * | 2000-03-16 | 2002-12-18 | F. Hoffmann-La Roche AG | Carboxylic acid derivatives as ip antagonists |
| ES2316613T3 (es) * | 2001-05-10 | 2009-04-16 | Ono Pharmaceutical Co., Ltd. | Derivados de acido crboxilico y composiciones farmaceuticas que contienen los mismos como ingrediente activo. |
| US6673791B2 (en) * | 2001-07-30 | 2004-01-06 | Boehringer Ingelheim (Canada) Ltd. | Non-nucleoside reverse transcriptase inhibitors |
-
2002
- 2002-06-12 GB GB0213488A patent/GB2389580A/en not_active Withdrawn
-
2003
- 2003-05-30 JP JP2004513236A patent/JP2005529180A/ja active Pending
- 2003-05-30 US US10/517,677 patent/US20060166989A1/en not_active Abandoned
- 2003-05-30 EP EP03735507A patent/EP1515941A1/en not_active Withdrawn
- 2003-05-30 CA CA002489286A patent/CA2489286A1/en not_active Abandoned
- 2003-05-30 AU AU2003238180A patent/AU2003238180A1/en not_active Abandoned
- 2003-05-30 WO PCT/EP2003/005705 patent/WO2003106402A1/en not_active Ceased
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