CA2489286A1 - 2-naphtamide derivatives - Google Patents
2-naphtamide derivatives Download PDFInfo
- Publication number
- CA2489286A1 CA2489286A1 CA002489286A CA2489286A CA2489286A1 CA 2489286 A1 CA2489286 A1 CA 2489286A1 CA 002489286 A CA002489286 A CA 002489286A CA 2489286 A CA2489286 A CA 2489286A CA 2489286 A1 CA2489286 A1 CA 2489286A1
- Authority
- CA
- Canada
- Prior art keywords
- naphthoyl
- optionally substituted
- phenylalanine
- aryl
- benzyloxy
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 108091006335 Prostaglandin I receptors Proteins 0.000 claims abstract description 30
- 238000011282 treatment Methods 0.000 claims abstract description 29
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical class C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000011321 prophylaxis Methods 0.000 claims abstract description 15
- 208000002193 Pain Diseases 0.000 claims abstract description 13
- 239000004480 active ingredient Substances 0.000 claims abstract description 12
- 239000002464 receptor antagonist Substances 0.000 claims abstract description 11
- 229940044551 receptor antagonist Drugs 0.000 claims abstract description 11
- 208000014001 urinary system disease Diseases 0.000 claims abstract description 10
- 208000001953 Hypotension Diseases 0.000 claims abstract description 9
- 206010061218 Inflammation Diseases 0.000 claims abstract description 9
- 230000036543 hypotension Effects 0.000 claims abstract description 9
- 230000004054 inflammatory process Effects 0.000 claims abstract description 9
- 208000032843 Hemorrhage Diseases 0.000 claims abstract description 8
- 208000031220 Hemophilia Diseases 0.000 claims abstract description 7
- 208000009292 Hemophilia A Diseases 0.000 claims abstract description 7
- 208000012931 Urologic disease Diseases 0.000 claims abstract description 4
- -1 hydroxy, amino Chemical group 0.000 claims description 79
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 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 description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 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 description 2
- XUUANZMLUUXACE-VWLOTQADSA-N (2s)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]-3-(1h-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CN=C2NC=1)C(=O)O)C(=O)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=CC=C1 XUUANZMLUUXACE-VWLOTQADSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- RXCMAMXNOXRSCD-QHCPKHFHSA-N (2s)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]-3-thiophen-2-ylpropanoic 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=CS1 RXCMAMXNOXRSCD-QHCPKHFHSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- WQRBBDJTEIFTTF-MHZLTWQESA-N (2s)-3-(1h-indol-3-yl)-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=CC=C1 WQRBBDJTEIFTTF-MHZLTWQESA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- QSVZEIDNWDHYMU-LJAQVGFWSA-N (2s)-3-naphthalen-1-yl-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2C=CC=1)C(=O)O)C(=O)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=CC=C1 QSVZEIDNWDHYMU-LJAQVGFWSA-N 0.000 claims description 2
- GOJWFDAPERTPAZ-LJAQVGFWSA-N (2s)-3-naphthalen-2-yl-2-[(6-phenylmethoxynaphthalene-2-carbonyl)amino]propanoic acid Chemical compound N([C@@H](CC=1C=C2C=CC=CC2=CC=1)C(=O)O)C(=O)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=CC=C1 GOJWFDAPERTPAZ-LJAQVGFWSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 21
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 abstract description 20
- 230000000694 effects Effects 0.000 abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 13
- 206010020853 Hypertonic bladder Diseases 0.000 abstract description 11
- 201000010099 disease Diseases 0.000 abstract description 11
- 208000009722 Overactive Urinary Bladder Diseases 0.000 abstract description 7
- 208000020629 overactive bladder Diseases 0.000 abstract description 7
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 abstract description 6
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- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/66—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and singly-bound oxygen atoms, bound to the same carbon skeleton
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0213488A GB2389580A (en) | 2002-06-12 | 2002-06-12 | 2-Naphthamide PGI2 antagonists |
| GB0213488.0 | 2002-06-12 | ||
| PCT/EP2003/005705 WO2003106402A1 (en) | 2002-06-12 | 2003-05-30 | 2-naphtamide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2489286A1 true CA2489286A1 (en) | 2003-12-24 |
Family
ID=9938442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002489286A Abandoned CA2489286A1 (en) | 2002-06-12 | 2003-05-30 | 2-naphtamide derivatives |
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 |
| WO2008059370A2 (en) | 2006-11-17 | 2008-05-22 | Pfizer Japan 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 |
| AU6894800A (en) * | 1999-08-06 | 2001-03-05 | Vertex Pharmaceuticals Incorporated | Caspase inhibitors and uses thereof |
| MXPA02008931A (es) * | 2000-03-16 | 2003-02-10 | Hoffmann La Roche | Derivados de acido carboxilico como antagonistas ip. |
| US7179817B2 (en) * | 2001-05-10 | 2007-02-20 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| 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 AU AU2003238180A patent/AU2003238180A1/en not_active Abandoned
- 2003-05-30 US US10/517,677 patent/US20060166989A1/en not_active Abandoned
- 2003-05-30 CA CA002489286A patent/CA2489286A1/en not_active Abandoned
- 2003-05-30 WO PCT/EP2003/005705 patent/WO2003106402A1/en not_active Ceased
- 2003-05-30 EP EP03735507A patent/EP1515941A1/en not_active Withdrawn
- 2003-05-30 JP JP2004513236A patent/JP2005529180A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB0213488D0 (en) | 2002-07-24 |
| GB2389580A (en) | 2003-12-17 |
| JP2005529180A (ja) | 2005-09-29 |
| AU2003238180A1 (en) | 2003-12-31 |
| EP1515941A1 (en) | 2005-03-23 |
| WO2003106402A1 (en) | 2003-12-24 |
| US20060166989A1 (en) | 2006-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |