DE3204892C2 - - Google Patents
Info
- Publication number
- DE3204892C2 DE3204892C2 DE3204892A DE3204892A DE3204892C2 DE 3204892 C2 DE3204892 C2 DE 3204892C2 DE 3204892 A DE3204892 A DE 3204892A DE 3204892 A DE3204892 A DE 3204892A DE 3204892 C2 DE3204892 C2 DE 3204892C2
- Authority
- DE
- Germany
- Prior art keywords
- group
- piperazinylcarbonyl
- dihydrocarbostyril
- crystals
- carbostyril
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 morpholino, 1-piperidyl group Chemical group 0.000 claims description 428
- 150000001875 compounds Chemical class 0.000 claims description 64
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 10
- UQYCHNFDTXIQMM-UHFFFAOYSA-N 6-(4-benzylpiperazine-1-carbonyl)-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1C(=O)N(CC1)CCN1CC1=CC=CC=C1 UQYCHNFDTXIQMM-UHFFFAOYSA-N 0.000 claims description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- HIMAPQCWSZVHEJ-UHFFFAOYSA-N 6-[4-(2-phenoxyethyl)piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1C(=O)N(CC1)CCN1CCOC1=CC=CC=C1 HIMAPQCWSZVHEJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 239000000496 cardiotonic agent Substances 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- BRTSRAFGNVSHJV-UHFFFAOYSA-N 6-[4-(2-methylpropyl)piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CN(CC(C)C)CCN1C(=O)C1=CC=C(NC(=O)CC2)C2=C1 BRTSRAFGNVSHJV-UHFFFAOYSA-N 0.000 claims 1
- ZBRWSODNRGCQMV-UHFFFAOYSA-N 6-[4-(2-phenoxyethyl)piperazine-1-carbonyl]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1C(=O)N(CC1)CCN1CCOC1=CC=CC=C1 ZBRWSODNRGCQMV-UHFFFAOYSA-N 0.000 claims 1
- MXCARJQEMVOHAU-UHFFFAOYSA-N 6-[4-(3-oxo-3-phenylpropyl)piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CN(C(=O)C=2C=C3CCC(=O)NC3=CC=2)CCN1CCC(=O)C1=CC=CC=C1 MXCARJQEMVOHAU-UHFFFAOYSA-N 0.000 claims 1
- CDRWBUGLZBPPCL-UHFFFAOYSA-N 6-[4-(3-phenylpropyl)piperazine-1-carbonyl]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1C(=O)N(CC1)CCN1CCCC1=CC=CC=C1 CDRWBUGLZBPPCL-UHFFFAOYSA-N 0.000 claims 1
- MMPBSPPVURMDBU-UHFFFAOYSA-N 6-[4-[(4-methoxyphenyl)methyl]piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC(OC)=CC=C1CN1CCN(C(=O)C=2C=C3CCC(=O)NC3=CC=2)CC1 MMPBSPPVURMDBU-UHFFFAOYSA-N 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 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 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 239000013078 crystal Substances 0.000 description 191
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 124
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- 239000000243 solution Substances 0.000 description 61
- 238000000354 decomposition reaction Methods 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
- 239000011541 reaction mixture Substances 0.000 description 47
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000203 mixture Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 229920006395 saturated elastomer Polymers 0.000 description 23
- 239000007858 starting material Substances 0.000 description 22
- 235000002639 sodium chloride Nutrition 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 239000011780 sodium chloride Substances 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- 241000282472 Canis lupus familiaris Species 0.000 description 11
- 230000000144 pharmacologic effect Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000012452 mother liquor Substances 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 7
- UKRYUVLBWGYQBY-UHFFFAOYSA-N 6-(piperazine-1-carbonyl)-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1C(=O)N1CCNCC1 UKRYUVLBWGYQBY-UHFFFAOYSA-N 0.000 description 7
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 6
- DUFYYKGNRAMGNG-UHFFFAOYSA-N 2-oxo-3,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound N1C(=O)CCC2=CC(C(=O)O)=CC=C21 DUFYYKGNRAMGNG-UHFFFAOYSA-N 0.000 description 6
- GCHAVGULYPPIHQ-UHFFFAOYSA-N 6-[4-(3,4-dimethoxybenzoyl)piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)N1CCN(C(=O)C=2C=C3CCC(=O)NC3=CC=2)CC1 GCHAVGULYPPIHQ-UHFFFAOYSA-N 0.000 description 6
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000017531 blood circulation Effects 0.000 description 6
- 239000002026 chloroform extract Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000001990 intravenous administration Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 5
- DRMRWGJNMPRBIO-UHFFFAOYSA-N 6-(piperazine-1-carbonyl)-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C=1C=C2NC(=O)C=CC2=CC=1C(=O)N1CCNCC1 DRMRWGJNMPRBIO-UHFFFAOYSA-N 0.000 description 5
- 229960001412 pentobarbital Drugs 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- DIVNUTGTTIRPQA-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1OC DIVNUTGTTIRPQA-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ZUGRYLJRHKHZLR-UHFFFAOYSA-N 1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)C=CC2=C1 ZUGRYLJRHKHZLR-UHFFFAOYSA-N 0.000 description 4
- ZJNIZXCCXHUGPO-UHFFFAOYSA-N 2-oxo-3,4-dihydro-1h-quinoline-6-carboxylic acid;pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1.N1C(=O)CCC2=CC(C(=O)O)=CC=C21 ZJNIZXCCXHUGPO-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 210000001367 artery Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 4
- 229920000669 heparin Polymers 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 150000002780 morpholines Chemical class 0.000 description 4
- 230000009090 positive inotropic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- DAUAQNGYDSHRET-UHFFFAOYSA-N 3,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1OC DAUAQNGYDSHRET-UHFFFAOYSA-N 0.000 description 3
- AIAGSFMDZZSAQY-UHFFFAOYSA-N 6-[4-(2-hydroxypropyl)piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CN(CC(O)C)CCN1C(=O)C1=CC=C(NC(=O)CC2)C2=C1 AIAGSFMDZZSAQY-UHFFFAOYSA-N 0.000 description 3
- NOTNUVGFGVOYCH-UHFFFAOYSA-N 6-[4-[(3,4-dimethoxyphenyl)methyl]piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CN1CCN(C(=O)C=2C=C3CCC(=O)NC3=CC=2)CC1 NOTNUVGFGVOYCH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- GPVDHNVGGIAOQT-UHFFFAOYSA-N Veratric acid Natural products COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 229940125715 antihistaminic agent Drugs 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 210000003540 papillary muscle Anatomy 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 210000005245 right atrium Anatomy 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 2
- JVDVDHKLAUQUCK-UHFFFAOYSA-N 1-[4-(2-oxo-3,4-dihydro-1h-quinoline-6-carbonyl)piperazin-1-yl]propan-2-yl acetate;hydrochloride Chemical compound Cl.C1CN(CC(C)OC(C)=O)CCN1C(=O)C1=CC=C(NC(=O)CC2)C2=C1 JVDVDHKLAUQUCK-UHFFFAOYSA-N 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- ZEGJLQZSCUPAPR-UHFFFAOYSA-N 2-oxo-1h-quinoline-6-carboxylic acid Chemical compound N1C(=O)C=CC2=CC(C(=O)O)=CC=C21 ZEGJLQZSCUPAPR-UHFFFAOYSA-N 0.000 description 2
- ORBGMTCJGXSBNO-UHFFFAOYSA-N 2-oxo-3,4-dihydro-1h-quinoline-5-carboxylic acid Chemical compound N1C(=O)CCC2=C1C=CC=C2C(=O)O ORBGMTCJGXSBNO-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 2
- YZMGOVZHTUYCIT-UHFFFAOYSA-N 3-(3-ethoxyprop-2-enoylamino)benzoic acid Chemical compound CCOC=CC(=O)NC1=CC=CC(C(O)=O)=C1 YZMGOVZHTUYCIT-UHFFFAOYSA-N 0.000 description 2
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- XBXGJWOWXZPSGV-UHFFFAOYSA-N 8-[4-(2-methylpropyl)piperazine-1-carbonyl]-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1CN(CC(C)C)CCN1C(=O)C1=CC=CC2=C1NC(=O)C=C2 XBXGJWOWXZPSGV-UHFFFAOYSA-N 0.000 description 1
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- AYYNUGSDPRDVCH-UHFFFAOYSA-N ethyl 3,4-dimethoxybenzoate Chemical compound CCOC(=O)C1=CC=C(OC)C(OC)=C1 AYYNUGSDPRDVCH-UHFFFAOYSA-N 0.000 description 1
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- ZSBYTZDMNFXERF-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-2-oxo-3,4-dihydro-1h-quinoline-6-carboxamide Chemical compound N1C(=O)CCC2=CC(C(=O)N(CCCl)CCCl)=CC=C21 ZSBYTZDMNFXERF-UHFFFAOYSA-N 0.000 description 1
- GUZWPGHACVQJLA-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)-2-oxo-3,4-dihydro-1h-quinoline-6-carboxamide Chemical compound N1C(=O)CCC2=CC(C(=O)N(CCO)CCO)=CC=C21 GUZWPGHACVQJLA-UHFFFAOYSA-N 0.000 description 1
- FJEVLIYCLTVMPM-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-n-methyl-2-oxo-3,4-dihydro-1h-quinoline-6-carboxamide Chemical compound N1C(=O)CCC2=CC(C(=O)N(CC=3C=C4OCOC4=CC=3)C)=CC=C21 FJEVLIYCLTVMPM-UHFFFAOYSA-N 0.000 description 1
- POVKLTHRUAHAHM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-n-methyl-2-oxo-3,4-dihydro-1h-quinoline-6-carboxamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1C(=O)N(C)CC1=CC=C(Cl)C=C1 POVKLTHRUAHAHM-UHFFFAOYSA-N 0.000 description 1
- HBUKVRTZBZARFA-UHFFFAOYSA-N n-[4-[3-[4-(2-oxo-3,4-dihydro-1h-quinoline-6-carbonyl)piperazin-1-yl]propanoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)CCN1CCN(C(=O)C=2C=C3CCC(=O)NC3=CC=2)CC1 HBUKVRTZBZARFA-UHFFFAOYSA-N 0.000 description 1
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- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
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- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000008337 systemic blood flow Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 210000000596 ventricular septum Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56022437A JPS57136517A (en) | 1981-02-17 | 1981-02-17 | Cardiotonic |
| JP56057732A JPS57171974A (en) | 1981-04-15 | 1981-04-15 | Carbostyril derivative |
| JP12714581A JPS5829766A (ja) | 1981-08-12 | 1981-08-12 | カルボスチリル誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3204892A1 DE3204892A1 (de) | 1982-09-23 |
| DE3204892C2 true DE3204892C2 (en, 2012) | 1988-03-24 |
Family
ID=27283844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823204892 Granted DE3204892A1 (de) | 1981-02-17 | 1982-02-12 | Carbostyrilderivate, verfahren zu deren herstellung und kardiotonische zusammensetzungen, welche diese enthalten |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US4487772A (en, 2012) |
| KR (1) | KR860001337B1 (en, 2012) |
| AT (1) | AT386198B (en, 2012) |
| AU (1) | AU530264B2 (en, 2012) |
| BE (1) | BE892148A (en, 2012) |
| CA (1) | CA1199915A (en, 2012) |
| CH (1) | CH651827A5 (en, 2012) |
| DE (1) | DE3204892A1 (en, 2012) |
| DK (1) | DK152287C (en, 2012) |
| ES (2) | ES509693A0 (en, 2012) |
| FI (1) | FI77852C (en, 2012) |
| FR (1) | FR2512818B1 (en, 2012) |
| GB (1) | GB2094789B (en, 2012) |
| IT (1) | IT1157002B (en, 2012) |
| MX (1) | MX156153A (en, 2012) |
| NL (1) | NL8200593A (en, 2012) |
| NO (1) | NO159446C (en, 2012) |
| PH (1) | PH18085A (en, 2012) |
| PT (1) | PT74440B (en, 2012) |
| SE (1) | SE445348B (en, 2012) |
| SU (1) | SU1331426A3 (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH17194A (en) * | 1980-03-06 | 1984-06-19 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives,and pharmaceutical composition containing the same |
| FI77852C (fi) * | 1981-02-17 | 1989-05-10 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av nya, saosom hjaertmediciner anvaendbara substituerade amid- och (maettad heterocykel)karbonylkarbostyrilderivat. |
| AU532361B2 (en) * | 1981-09-01 | 1983-09-29 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
| US4578381A (en) * | 1982-07-05 | 1986-03-25 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
| US4845100A (en) * | 1985-04-12 | 1989-07-04 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives and salts thereof, processes for preparing the same and cardiotonic composition containing the same |
| US4921862A (en) * | 1986-05-29 | 1990-05-01 | Syntex (U.S.A.) Inc. | Carbostyril derivatives as combined thromboxane synthetase and cyclic-amp phosphodiesterase inhibitors |
| US4792561A (en) * | 1986-05-29 | 1988-12-20 | Syntex (U.S.A.) Inc. | Carbostyril derivatives as combined thromboxane synthetase and cyclic-AMP phosphodiesterase inhibitors |
| DK397387A (da) * | 1986-07-31 | 1988-02-01 | Otsuka Pharma Co Ltd | Carbostyrilderivater og salte deraf samt fremgangsmaade til fremstilling af saadanne forbindelser |
| GB8709448D0 (en) * | 1987-04-21 | 1987-05-28 | Pfizer Ltd | Heterobicyclic quinoline derivatives |
| US5227381A (en) * | 1988-05-02 | 1993-07-13 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivative |
| DE3818830A1 (de) * | 1988-06-03 | 1989-12-14 | Boehringer Mannheim Gmbh | Bicyclische carboxamide, verfahren zu ihrer herstellung, deren vorstufen, und diese verbindungen enthaltende arzneimittel |
| JP2686887B2 (ja) * | 1992-08-11 | 1997-12-08 | キッセイ薬品工業株式会社 | ピペリジノ−３，４−ジヒドロカルボスチリル誘導体 |
| JPH06239858A (ja) * | 1993-02-16 | 1994-08-30 | Otsuka Pharmaceut Co Ltd | 末梢血管拡張剤 |
| CN1052224C (zh) * | 1993-04-07 | 2000-05-10 | 大塚制药株式会社 | 哌啶衍生物、含有它的外周血管舒张剂及其应用 |
| ES2128629T3 (es) * | 1994-10-31 | 1999-05-16 | Merck Patent Gmbh | Derivados de bencilpiperidina con afinidad elevada a puntos de enlace de receptores de aminoacidos. |
| US6589954B1 (en) * | 1998-05-22 | 2003-07-08 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| US6340685B1 (en) * | 1998-05-22 | 2002-01-22 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| US6867209B1 (en) | 1998-05-22 | 2005-03-15 | Scios, Inc. | Indole-type derivatives as inhibitors of p38 kinase |
| US6448257B1 (en) | 1998-05-22 | 2002-09-10 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| IL146309A (en) | 1999-05-21 | 2008-03-20 | Scios Inc | Derivatives of the indole type and pharmaceutical preparations containing them as inhibitors of kinase p38 |
| WO2004014389A1 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | 3,4-dihydroquinolin-2-one, 5,6-fused oxazin-3-one, and 5,6-fused thiazin-3-one derivatives as matrix metalloproteinase inhibitors |
| CN1890225A (zh) * | 2003-12-10 | 2007-01-03 | 詹森药业有限公司 | 作为多聚(adp－核糖)聚合酶抑制剂的被取代的6－环己基烷基取代的2－喹啉酮和2－喹喔啉酮 |
| MY142362A (en) * | 2004-01-29 | 2010-11-30 | Otsuka Pharma Co Ltd | Pharmaceutical composition for promoting angiogenesis |
| EP2021340B1 (en) | 2006-04-21 | 2014-07-23 | The Government Of The United States, As Represented by The Secretary Of Health And Human Services | Beta-amyloid pet imaging agents |
| WO2010021681A2 (en) * | 2008-08-18 | 2010-02-25 | Combinatorx (Singapore) Pte. Ltd. | Compositions and methods for treatment of viral diseases |
| AU2010266018B2 (en) | 2009-06-25 | 2014-01-09 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| EP2566329B1 (en) | 2010-05-04 | 2020-09-09 | Alkermes Pharma Ireland Limited | Process for synthesizing oxidized lactam compounds |
| WO2011163594A2 (en) | 2010-06-24 | 2011-12-29 | Alkermes, Inc. | Prodrugs of nh-acidic compounds: ester, carbonate, carbamate and phosphonate derivatives |
| JP7269948B2 (ja) * | 2017-11-28 | 2023-05-09 | エフ． ホフマン－ラ ロシュ アーゲー | 新規複素環式化合物 |
| WO2019134985A1 (en) | 2018-01-08 | 2019-07-11 | F. Hoffmann-La Roche Ag | Octahydropyrido[1,2-alpha]pyrazines as magl inhibitors |
| CN109651285B (zh) * | 2019-01-30 | 2020-06-30 | 苏州大学 | 多溴代苯并[1,3]噁嗪衍生物的合成方法 |
| CA3190277A1 (en) | 2020-09-03 | 2022-03-10 | Joerg Benz | Heterocyclic compounds |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2997474A (en) * | 1959-10-12 | 1961-08-22 | Paul A J Janssen | 1-aryl-omega-(4-arylpiperazine) alkanols |
| US3555030A (en) * | 1964-11-25 | 1971-01-12 | Smith Kline French Lab | Muscle relaxant and analgesic compositions |
| US4115569A (en) * | 1971-11-19 | 1978-09-19 | Hoechst Aktiengesellschaft | Cyclic diamine derivatives |
| US4256890A (en) * | 1972-09-14 | 1981-03-17 | Otsukapharmaceutical Co., Ltd. | 3,4-Dihydrocarbostyril derivatives and process for producing the same |
| IT998326B (it) * | 1973-08-06 | 1976-01-20 | Montedison Spa | Derivati degli acidi chinolin 8 carbossilici ad attivita antiparas sitaria |
| US4026897A (en) * | 1974-01-31 | 1977-05-31 | Otsuka Pharmaceutical Company | 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxycarbostyril derivatives |
| US4022784A (en) * | 1974-01-31 | 1977-05-10 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-substituted-carbostyril and -3,4-dihydrocarbostyril derivatives |
| US4145542A (en) * | 1974-06-13 | 1979-03-20 | Otsuka Pharmaceutical Co., Ltd. | 5- 1-Hydroxy-2-(heterocyclic-amino)!alkyl-8-hydroxy-3,4-dihydrocarbostyril derivatives |
| FI59246C (fi) * | 1974-06-24 | 1981-07-10 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av benscykloamidderivat anvaendbara vid trombos- och emboliterapin |
| JPS51118771A (en) * | 1975-04-09 | 1976-10-18 | Otsuka Pharmaceut Co Ltd | Method for preparing carbostyryl derivatives |
| US3994900A (en) * | 1976-01-23 | 1976-11-30 | E. R. Squibb & Sons, Inc. | 6-(Or 8)-[[(substituted amino)alkyl]oxy(or thio)]-3,4-dihydro-4-phenyl-2(1H)-quinolinones |
| US4210753A (en) * | 1976-03-17 | 1980-07-01 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compounds |
| GB1589871A (en) * | 1976-07-19 | 1981-05-20 | Conder Group Serv Ltd | Tank construction |
| JPS609713B2 (ja) * | 1976-10-08 | 1985-03-12 | 大塚製薬株式会社 | カルボスチリル誘導体 |
| IE46852B1 (en) * | 1977-06-10 | 1983-10-05 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives |
| JPS5416478A (en) * | 1977-07-08 | 1979-02-07 | Otsuka Pharmaceut Co Ltd | 3,4-dihydrocarbostyril herivative |
| DE2928583A1 (de) * | 1979-07-14 | 1981-01-29 | Thomae Gmbh Dr K | Verfahren zur herstellung von carbostyrilderivaten |
| PH17194A (en) * | 1980-03-06 | 1984-06-19 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives,and pharmaceutical composition containing the same |
| FI77852C (fi) * | 1981-02-17 | 1989-05-10 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av nya, saosom hjaertmediciner anvaendbara substituerade amid- och (maettad heterocykel)karbonylkarbostyrilderivat. |
-
1982
- 1982-02-03 FI FI820338A patent/FI77852C/fi not_active IP Right Cessation
- 1982-02-12 DE DE19823204892 patent/DE3204892A1/de active Granted
- 1982-02-15 BE BE0/207321A patent/BE892148A/fr not_active IP Right Cessation
- 1982-02-15 MX MX8210261A patent/MX156153A/es unknown
- 1982-02-15 PH PH26870A patent/PH18085A/en unknown
- 1982-02-15 SU SU823394100A patent/SU1331426A3/ru active
- 1982-02-16 SE SE8200916A patent/SE445348B/sv not_active IP Right Cessation
- 1982-02-16 FR FR8202479A patent/FR2512818B1/fr not_active Expired
- 1982-02-16 US US06/348,709 patent/US4487772A/en not_active Expired - Lifetime
- 1982-02-16 NL NL8200593A patent/NL8200593A/nl not_active Application Discontinuation
- 1982-02-16 PT PT74440A patent/PT74440B/pt not_active IP Right Cessation
- 1982-02-16 NO NO820479A patent/NO159446C/no unknown
- 1982-02-16 AT AT0059582A patent/AT386198B/de not_active IP Right Cessation
- 1982-02-16 CA CA000396327A patent/CA1199915A/en not_active Expired
- 1982-02-16 DK DK066582A patent/DK152287C/da active
- 1982-02-16 AU AU80528/82A patent/AU530264B2/en not_active Ceased
- 1982-02-16 KR KR8200668A patent/KR860001337B1/ko not_active Expired
- 1982-02-17 IT IT67177/82A patent/IT1157002B/it active
- 1982-02-17 ES ES509693A patent/ES509693A0/es active Granted
- 1982-02-17 GB GB8204581A patent/GB2094789B/en not_active Expired
- 1982-02-17 CH CH996/82A patent/CH651827A5/de not_active IP Right Cessation
- 1982-12-16 ES ES518303A patent/ES518303A0/es active Granted
-
1983
- 1983-08-22 US US06/525,812 patent/US4454130A/en not_active Expired - Lifetime
- 1983-08-22 US US06/525,284 patent/US4468402A/en not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
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| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8125 | Change of the main classification |
Ipc: C07D401/12 |
|
| 8126 | Change of the secondary classification |
Free format text: C07D215/22 A61K 31/495 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |