KR20010020386A - 포스포디에스테라제 4를 억제하는 디아제피노인돌론 - Google Patents
포스포디에스테라제 4를 억제하는 디아제피노인돌론 Download PDFInfo
- Publication number
- KR20010020386A KR20010020386A KR1019997010008A KR19997010008A KR20010020386A KR 20010020386 A KR20010020386 A KR 20010020386A KR 1019997010008 A KR1019997010008 A KR 1019997010008A KR 19997010008 A KR19997010008 A KR 19997010008A KR 20010020386 A KR20010020386 A KR 20010020386A
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- KR
- South Korea
- Prior art keywords
- oxo
- methyl
- phenyl
- dihydro
- quinazolin
- 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.)
- Ceased
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- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title description 8
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- 238000000034 method Methods 0.000 claims abstract description 135
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 208000006673 asthma Diseases 0.000 claims abstract description 10
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 3
- 230000036303 septic shock Effects 0.000 claims abstract description 3
- -1 2,5-dimethyl-4-oxo-4H-quinazolin-3-yl Chemical group 0.000 claims description 115
- 239000000203 mixture Substances 0.000 claims description 101
- 239000000460 chlorine Substances 0.000 claims description 95
- 239000000543 intermediate Substances 0.000 claims description 70
- 239000002904 solvent Substances 0.000 claims description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
- 150000001412 amines Chemical class 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- KCKIKSJECTZLJA-UHFFFAOYSA-N indol-4-one Chemical compound O=C1C=CC=C2N=CC=C12 KCKIKSJECTZLJA-UHFFFAOYSA-N 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000002609 medium Substances 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- GSXVPNLAOHBBKA-UHFFFAOYSA-N 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carboxylic acid Chemical compound C=1C(C)=CC=2CCN(C(C(N=3)N4C(C5=CC=C(C=C5N=C4C)C(O)=O)=O)=O)C=2C=1C=3C1=CC=CC=C1 GSXVPNLAOHBBKA-UHFFFAOYSA-N 0.000 claims description 11
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 11
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 claims description 9
- 230000009435 amidation Effects 0.000 claims description 9
- 238000007112 amidation reaction Methods 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- RTDDGJVVKVRATF-UHFFFAOYSA-N 1,10-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7,9-pentaen-12-one Chemical group O=C1CN=Cc2cccc3ccn1c23 RTDDGJVVKVRATF-UHFFFAOYSA-N 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002466 imines Chemical class 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 5
- 229910052987 metal hydride Inorganic materials 0.000 claims description 5
- 150000004681 metal hydrides Chemical class 0.000 claims description 5
- DAJBLWXUFLHGGH-DEOSSOPVSA-N (11S)-11-(2-methyl-4-oxoquinazolin-3-yl)-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound N([C@H](C(N1CCC=2C=CC=C3C1=2)=O)N1C(=O)C2=CC=CC=C2N=C1C)=C3C1=CC=CC=C1 DAJBLWXUFLHGGH-DEOSSOPVSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 239000004472 Lysine Substances 0.000 claims description 4
- 230000006181 N-acylation Effects 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 4
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 4
- 239000004220 glutamic acid Substances 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 4
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 4
- PKVZSJLYYVGXRM-QHCPKHFHSA-N (11S)-11-(2-methyl-4-oxopyrido[3,4-d]pyrimidin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound N([C@H](C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N1C(=O)C2=CC=NC=C2N=C1C)=C3C1=CC=CC=C1 PKVZSJLYYVGXRM-QHCPKHFHSA-N 0.000 claims description 3
- GCQYMZYZLNYUSY-VWLOTQADSA-N (11S)-11-(5-fluoro-2-methyl-4-oxoquinazolin-3-yl)-6-methyl-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound C=1C(C)=CC=2CCN(C([C@@H](N=3)N4C(C5=C(F)C=CC=C5N=C4C)=O)=O)C=2C=1C=3C1=CC=CC=C1 GCQYMZYZLNYUSY-VWLOTQADSA-N 0.000 claims description 3
- YJLSARIGMMOOGK-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carboxylate Chemical compound C=1C(C)=CC=2CCN(C3=O)C=2C=1C(C=1C=CC=CC=1)=NC3N(C(C1=CC=2)=O)C(C)=NC1=CC=2C(=O)OC1=C(F)C(F)=C(F)C(F)=C1F YJLSARIGMMOOGK-UHFFFAOYSA-N 0.000 claims description 3
- UQPGREVGZRHTAK-UHFFFAOYSA-N 11-(2,5-dimethyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=NC2=CC=CC(C)=C2C(=O)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 UQPGREVGZRHTAK-UHFFFAOYSA-N 0.000 claims description 3
- FKMLEKVIYSANCY-UHFFFAOYSA-N 11-(2,6-dimethyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound O=C1C2=CC(C)=CC=C2N=C(C)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 FKMLEKVIYSANCY-UHFFFAOYSA-N 0.000 claims description 3
- PNFWYEXLXYPSPZ-UHFFFAOYSA-N 11-(2,7-dimethyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound C=1C(C)=CC=C(C2=O)C=1N=C(C)N2C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 PNFWYEXLXYPSPZ-UHFFFAOYSA-N 0.000 claims description 3
- LUQNQFIQFJBKRV-UHFFFAOYSA-N 11-(2,8-dimethyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=NC2=C(C)C=CC=C2C(=O)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 LUQNQFIQFJBKRV-UHFFFAOYSA-N 0.000 claims description 3
- RGERZKVLIURXPY-UHFFFAOYSA-N 11-(2-methyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=NC2=CC=CC=C2C(=O)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 RGERZKVLIURXPY-UHFFFAOYSA-N 0.000 claims description 3
- AZQNANWJQLZKCT-UHFFFAOYSA-N 11-(5-chloro-2-methyl-4-oxoquinazolin-3-yl)-6-methyl-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound C=1C(C)=CC=2CCN(C(C(N=3)N4C(C5=C(Cl)C=CC=C5N=C4C)=O)=O)C=2C=1C=3C1=CC=CC=C1 AZQNANWJQLZKCT-UHFFFAOYSA-N 0.000 claims description 3
- HXSPYSYFRCKEPX-UHFFFAOYSA-N 11-(5-chloro-2-methyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=NC2=CC=CC(Cl)=C2C(=O)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 HXSPYSYFRCKEPX-UHFFFAOYSA-N 0.000 claims description 3
- FGVLFFGUYNXWKT-UHFFFAOYSA-N 11-[2-(methoxymethyl)-4-oxoquinazolin-3-yl]-6-methyl-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound COCC1=NC2=CC=CC=C2C(=O)N1C(C(N1CCC=2C=C(C)C=C3C1=2)=O)N=C3C1=CC=CC=C1 FGVLFFGUYNXWKT-UHFFFAOYSA-N 0.000 claims description 3
- MEULVEMAASHPAZ-UHFFFAOYSA-N 2-acetyloxyethyl 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carboxylate Chemical compound C=1C(C(=O)OCCOC(=O)C)=CC=C(C2=O)C=1N=C(C)N2C(C(N1CCC=2C=C(C)C=C3C1=2)=O)N=C3C1=CC=CC=C1 MEULVEMAASHPAZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- IFMSCYUQRZNAFK-UHFFFAOYSA-N 2-methoxyethyl 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carboxylate Chemical compound C=1C(C(=O)OCCOC)=CC=C(C2=O)C=1N=C(C)N2C(C(N1CCC=2C=C(C)C=C3C1=2)=O)N=C3C1=CC=CC=C1 IFMSCYUQRZNAFK-UHFFFAOYSA-N 0.000 claims description 3
- AJGTXMYFYOYFFV-UHFFFAOYSA-N 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-5-carboxylic acid Chemical compound C=1C(C)=CC=2CCN(C(C(N=3)N4C(C5=C(C(O)=O)C=CC=C5N=C4C)=O)=O)C=2C=1C=3C1=CC=CC=C1 AJGTXMYFYOYFFV-UHFFFAOYSA-N 0.000 claims description 3
- WPSKYVMJHNFMOZ-UHFFFAOYSA-N 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carbonitrile Chemical compound C=1C(C)=CC=2CCN(C(C(N=3)N4C(C5=CC=C(C=C5N=C4C)C#N)=O)=O)C=2C=1C=3C1=CC=CC=C1 WPSKYVMJHNFMOZ-UHFFFAOYSA-N 0.000 claims description 3
- WWCKONRFPLGFIA-UHFFFAOYSA-N 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carboxamide Chemical compound C=1C(C)=CC=2CCN(C(C(N=3)N4C(C5=CC=C(C=C5N=C4C)C(N)=O)=O)=O)C=2C=1C=3C1=CC=CC=C1 WWCKONRFPLGFIA-UHFFFAOYSA-N 0.000 claims description 3
- MNGFGZLQQZOPHM-UHFFFAOYSA-N 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-N-(2-morpholin-4-ylethyl)-4-oxoquinazoline-7-carboxamide Chemical compound C=1C(C)=CC=2CCN(C3=O)C=2C=1C(C=1C=CC=CC=1)=NC3N(C(C1=CC=2)=O)C(C)=NC1=CC=2C(=O)NCCN1CCOCC1 MNGFGZLQQZOPHM-UHFFFAOYSA-N 0.000 claims description 3
- GSXVPNLAOHBBKA-RUZDIDTESA-N 2-methyl-3-[(11R)-6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl]-4-oxoquinazoline-7-carboxylic acid Chemical compound C=1C(C)=CC=2CCN(C([C@H](N=3)N4C(C5=CC=C(C=C5N=C4C)C(O)=O)=O)=O)C=2C=1C=3C1=CC=CC=C1 GSXVPNLAOHBBKA-RUZDIDTESA-N 0.000 claims description 3
- GSXVPNLAOHBBKA-VWLOTQADSA-N 2-methyl-3-[(11S)-6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl]-4-oxoquinazoline-7-carboxylic acid Chemical compound C=1C(C)=CC=2CCN(C([C@@H](N=3)N4C(C5=CC=C(C=C5N=C4C)C(O)=O)=O)=O)C=2C=1C=3C1=CC=CC=C1 GSXVPNLAOHBBKA-VWLOTQADSA-N 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- LQAPQOZOEQHAPS-UHFFFAOYSA-N 3-(6-amino-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-2-methyl-4-oxoquinazoline-7-carboxylic acid Chemical compound CC1=NC2=CC(C(O)=O)=CC=C2C(=O)N1C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 LQAPQOZOEQHAPS-UHFFFAOYSA-N 0.000 claims description 3
- QDPBNMRFDOTINQ-UHFFFAOYSA-N 3-(6-methoxy-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-2-methyl-4-oxoquinazoline-7-carboxylic acid Chemical compound C=1C(OC)=CC=2CCN(C(C(N=3)N4C(C5=CC=C(C=C5N=C4C)C(O)=O)=O)=O)C=2C=1C=3C1=CC=CC=C1 QDPBNMRFDOTINQ-UHFFFAOYSA-N 0.000 claims description 3
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 3
- ZCGHSRSNETYNGK-UHFFFAOYSA-N 6-amino-11-(2,5-dimethyl-4-oxoquinazolin-3-yl)-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(C)N1C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 ZCGHSRSNETYNGK-UHFFFAOYSA-N 0.000 claims description 3
- MAFQVPGPTOTYMX-UHFFFAOYSA-N 6-amino-11-(2,6-dimethyl-4-oxoquinazolin-3-yl)-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound O=C1C2=CC(C)=CC=C2N=C(C)N1C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 MAFQVPGPTOTYMX-UHFFFAOYSA-N 0.000 claims description 3
- OTCUEKHKDLNSDY-UHFFFAOYSA-N 6-amino-11-(2,8-dimethyl-4-oxoquinazolin-3-yl)-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=CC=CC(C2=O)=C1N=C(C)N2C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 OTCUEKHKDLNSDY-UHFFFAOYSA-N 0.000 claims description 3
- UPZQLUGOLBVHKF-UHFFFAOYSA-N 6-amino-11-(2-methyl-4-oxoquinazolin-3-yl)-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=NC2=CC=CC=C2C(=O)N1C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 UPZQLUGOLBVHKF-UHFFFAOYSA-N 0.000 claims description 3
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- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- 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
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9705422A FR2762841B1 (fr) | 1997-04-30 | 1997-04-30 | Diazepino-indolones inhibitrices de phosphodiesterases iv |
| FR97/05422 | 1997-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20010020386A true KR20010020386A (ko) | 2001-03-15 |
Family
ID=9506517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019997010008A Ceased KR20010020386A (ko) | 1997-04-30 | 1998-04-30 | 포스포디에스테라제 4를 억제하는 디아제피노인돌론 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6239130B1 (enExample) |
| EP (1) | EP0980374B1 (enExample) |
| JP (1) | JP2001522367A (enExample) |
| KR (1) | KR20010020386A (enExample) |
| AT (1) | ATE232534T1 (enExample) |
| AU (1) | AU729495B2 (enExample) |
| BR (1) | BR9809429A (enExample) |
| CA (1) | CA2278217A1 (enExample) |
| DE (1) | DE69811360T2 (enExample) |
| DK (1) | DK0980374T3 (enExample) |
| ES (1) | ES2190083T3 (enExample) |
| FR (1) | FR2762841B1 (enExample) |
| HR (1) | HRP980231B1 (enExample) |
| MX (1) | MXPA99006979A (enExample) |
| NZ (1) | NZ337589A (enExample) |
| WO (1) | WO1998049169A1 (enExample) |
| ZA (1) | ZA983704B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2795731B1 (fr) * | 1999-07-02 | 2001-09-07 | Warner Lambert Co | PROCEDE DE PREPARATION DE [1,4] DIAZEPINO [6,7,1-hi] INDOL-4-ONES SUBSTITUEES |
| AU3217501A (en) * | 2000-03-03 | 2001-09-12 | Pfizer Prod Inc | Pyrazole ether derivatives as anti-inflammatory/analgesic agents |
| EP1161949A1 (en) | 2000-06-09 | 2001-12-12 | Warner-Lambert Company | Use od diazepinoindoles for the treatment of chronic obstructive pulmonary disease |
| EP1188438A1 (en) * | 2000-09-15 | 2002-03-20 | Warner-Lambert Company | Pharmaceutical composition for preventing or treating a disease associated with an excess of Il-12 production |
| EP1199074A1 (en) * | 2000-09-15 | 2002-04-24 | Warner-Lambert Company | Pharmaceutical composition for preventing or treating a disease associated with an excess of il-12 production |
| EP1389467B1 (en) | 2001-05-23 | 2013-07-03 | Mitsubishi Tanabe Pharma Corporation | Therapeutic composition for the regenerative treatment of cartilage diseases |
| WO2002094321A1 (en) | 2001-05-23 | 2002-11-28 | Tanabe Seiyaku Co., Ltd. | Compositions for promoting healing of bone fracture |
| AU2002317377A1 (en) * | 2001-07-20 | 2003-03-03 | Cancer Research Technology Limited | Biphenyl apurinic/apyrimidinic site endonuclease inhibitors to treat cancer |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| US20050187278A1 (en) * | 2003-08-28 | 2005-08-25 | Pharmacia Corporation | Treatment or prevention of vascular disorders with Cox-2 inhibitors in combination with cyclic AMP-specific phosphodiesterase inhibitors |
| US20090042951A1 (en) * | 2004-02-20 | 2009-02-12 | Robert Danziger | Blood Pressure Reduction in Salt-Sensitive Hypertension |
| KR20070007945A (ko) * | 2004-04-23 | 2007-01-16 | 셀진 코포레이션 | 폐 고혈압증의 치료 및 관리를 위한 ｐｄｅ4 조절인자의사용 방법 및 그를 포함하는 조성물 |
| EA016037B1 (ru) * | 2005-04-19 | 2012-01-30 | Никомед Гмбх | Рофлумиласт для лечения лёгочной гипертензии |
| MX2009003673A (es) * | 2006-10-04 | 2009-04-22 | Pfizer Prod Inc | Derivados de piridido[4,3-d]pirimidin-4(3h)-ona como antagonistas de los receptores de calcio. |
| US20090182035A1 (en) * | 2007-04-11 | 2009-07-16 | Alcon Research, Ltd. | Use of a combination of olopatadine and cilomilast to treat non-infectious rhinitis and allergic conjunctivitis |
| CN101641094A (zh) * | 2007-04-11 | 2010-02-03 | 爱尔康研究有限公司 | TNFα抑制剂联合抗组胺药治疗变应性鼻炎和变应性结膜炎的用途 |
| KR20100037047A (ko) * | 2007-06-26 | 2010-04-08 | 렉시컨 파마슈티컬스 인코퍼레이티드 | 세로토닌-매개 질환 및 장애의 치료 방법 |
| BR112012007091A2 (pt) * | 2009-10-01 | 2016-04-19 | Alcon Res Ltd | composições de olopatadina e seus usos |
| MX2021007938A (es) | 2018-12-28 | 2022-01-24 | Regeneron Pharma | Tratamiento de trastornos respiratorios con inhibidores de la araquidonato 15-lipooxigenasa (alox15). |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2725719B1 (fr) * | 1994-10-14 | 1996-12-06 | Jouveinal Inst Rech | Diazepino-indoles inhibiteurs de phosphodiesterases iv |
-
1997
- 1997-04-30 FR FR9705422A patent/FR2762841B1/fr not_active Expired - Fee Related
-
1998
- 1998-04-29 HR HR980231A patent/HRP980231B1/xx not_active IP Right Cessation
- 1998-04-30 NZ NZ337589A patent/NZ337589A/xx unknown
- 1998-04-30 ZA ZA9803704A patent/ZA983704B/xx unknown
- 1998-04-30 BR BR9809429-7A patent/BR9809429A/pt not_active IP Right Cessation
- 1998-04-30 ES ES98925598T patent/ES2190083T3/es not_active Expired - Lifetime
- 1998-04-30 KR KR1019997010008A patent/KR20010020386A/ko not_active Ceased
- 1998-04-30 DE DE69811360T patent/DE69811360T2/de not_active Expired - Fee Related
- 1998-04-30 EP EP98925598A patent/EP0980374B1/en not_active Expired - Lifetime
- 1998-04-30 WO PCT/EP1998/002827 patent/WO1998049169A1/en not_active Ceased
- 1998-04-30 DK DK98925598T patent/DK0980374T3/da active
- 1998-04-30 AU AU77652/98A patent/AU729495B2/en not_active Ceased
- 1998-04-30 JP JP54662498A patent/JP2001522367A/ja not_active Abandoned
- 1998-04-30 CA CA002278217A patent/CA2278217A1/en not_active Abandoned
- 1998-04-30 US US09/380,883 patent/US6239130B1/en not_active Expired - Fee Related
- 1998-04-30 AT AT98925598T patent/ATE232534T1/de not_active IP Right Cessation
- 1998-04-30 MX MXPA99006979A patent/MXPA99006979A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA99006979A (es) | 2005-04-19 |
| EP0980374B1 (en) | 2003-02-12 |
| FR2762841B1 (fr) | 1999-07-02 |
| DK0980374T3 (da) | 2003-05-05 |
| DE69811360T2 (de) | 2003-10-09 |
| ATE232534T1 (de) | 2003-02-15 |
| BR9809429A (pt) | 2000-06-13 |
| DE69811360D1 (de) | 2003-03-20 |
| AU7765298A (en) | 1998-11-24 |
| ZA983704B (en) | 1999-10-25 |
| JP2001522367A (ja) | 2001-11-13 |
| AU729495B2 (en) | 2001-02-01 |
| EP0980374A1 (en) | 2000-02-23 |
| WO1998049169A1 (en) | 1998-11-05 |
| HRP980231A2 (en) | 2000-04-30 |
| US6239130B1 (en) | 2001-05-29 |
| FR2762841A1 (fr) | 1998-11-06 |
| NZ337589A (en) | 2000-10-27 |
| CA2278217A1 (en) | 1998-11-05 |
| ES2190083T3 (es) | 2003-07-16 |
| HRP980231B1 (en) | 2002-06-30 |
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