DE3034237C2 - - Google Patents
Info
- Publication number
- DE3034237C2 DE3034237C2 DE3034237A DE3034237A DE3034237C2 DE 3034237 C2 DE3034237 C2 DE 3034237C2 DE 3034237 A DE3034237 A DE 3034237A DE 3034237 A DE3034237 A DE 3034237A DE 3034237 C2 DE3034237 C2 DE 3034237C2
- Authority
- DE
- Germany
- Prior art keywords
- propoxy
- piperidyl
- dihydrocarbostyril
- general formula
- group
- 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
- 150000001875 compounds Chemical class 0.000 claims description 52
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 41
- -1 hydroxycarbostyril compound Chemical class 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 30
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000000739 antihistaminic agent Substances 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- OSBIUPYCASTLMN-UHFFFAOYSA-N 1-benzyl-5-[3-(4-benzylpiperidin-1-yl)-2-hydroxypropoxy]-3,4-dihydroquinolin-2-one Chemical compound C1CC(CC=2C=CC=CC=2)CCN1CC(O)COC(C=1CCC2=O)=CC=CC=1N2CC1=CC=CC=C1 OSBIUPYCASTLMN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- CPXJWPACAUOGMV-UHFFFAOYSA-N 7-[2-hydroxy-3-(4-phenylpiperidin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2CCC(=O)NC2=CC=1OCC(O)CN(CC1)CCC1C1=CC=CC=C1 CPXJWPACAUOGMV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003053 piperidines Chemical class 0.000 claims 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- HTDQENYSJWXFDB-UHFFFAOYSA-N 5-[3-(4-benzylpiperidin-1-yl)-2-hydroxypropoxy]-1-ethyl-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(CC)C(=O)CCC2=C1OCC(O)CN(CC1)CCC1CC1=CC=CC=C1 HTDQENYSJWXFDB-UHFFFAOYSA-N 0.000 claims 1
- WPDWZOVFEUABEB-UHFFFAOYSA-N 5-[3-(4-benzylpiperidin-1-yl)propoxy]-1-methyl-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(C)C(=O)CCC2=C1OCCCN(CC1)CCC1CC1=CC=CC=C1 WPDWZOVFEUABEB-UHFFFAOYSA-N 0.000 claims 1
- GUXWIKFZXZAIRK-UHFFFAOYSA-N 7-[3-(4-benzylpiperidin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2NC(=O)CCC2=CC=C1OCCCN(CC1)CCC1CC1=CC=CC=C1 GUXWIKFZXZAIRK-UHFFFAOYSA-N 0.000 claims 1
- OUWSDTRQZKYREJ-UHFFFAOYSA-N 7-[3-(4-phenylpiperidin-1-yl)propoxy]-1-(3-phenylpropyl)-3,4-dihydroquinolin-2-one Chemical compound C1=C2N(CCCC=3C=CC=CC=3)C(=O)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC=C1 OUWSDTRQZKYREJ-UHFFFAOYSA-N 0.000 claims 1
- DCEHMYOYSWLMFZ-UHFFFAOYSA-N 7-[3-(4-phenylpiperidin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2NC(=O)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC=C1 DCEHMYOYSWLMFZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 description 133
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 123
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 90
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 46
- 239000000203 mixture Substances 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 230000001387 anti-histamine Effects 0.000 description 9
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 7
- ABGXADJDTPFFSZ-UHFFFAOYSA-N 4-benzylpiperidine Chemical compound C=1C=CC=CC=1CC1CCNCC1 ABGXADJDTPFFSZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- BLHINBOCRRLTEO-UHFFFAOYSA-N 5-[3-(4-benzylpiperidin-1-yl)-2-hydroxypropoxy]-1-methyl-3,4-dihydroquinolin-2-one;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC=C2N(C)C(=O)CCC2=C1OCC(O)CN(CC1)CCC1CC1=CC=CC=C1 BLHINBOCRRLTEO-UHFFFAOYSA-N 0.000 description 5
- VBDQGQHFWKCKLW-UHFFFAOYSA-N 6-[2-hydroxy-3-[4-(3,4,5-trimethoxyphenyl)piperidin-1-yl]propoxy]-1-(3-methylbutyl)-3,4-dihydroquinolin-2-one;oxalic acid Chemical compound OC(=O)C(O)=O.COC1=C(OC)C(OC)=CC(C2CCN(CC(O)COC=3C=C4CCC(=O)N(CCC(C)C)C4=CC=3)CC2)=C1 VBDQGQHFWKCKLW-UHFFFAOYSA-N 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- 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 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 229960003132 halothane Drugs 0.000 description 5
- 229960001340 histamine Drugs 0.000 description 5
- 210000003405 ileum Anatomy 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- ZSHZOONYRBYGNV-UHFFFAOYSA-N 5-[3-(4-benzylpiperidin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=CC=C2OCCCN(CC1)CCC1CC1=CC=CC=C1 ZSHZOONYRBYGNV-UHFFFAOYSA-N 0.000 description 4
- WEFCOUPECCVVSW-UHFFFAOYSA-N 6-[3-(4-benzylpiperidin-1-yl)propoxy]-4-methyl-1h-quinolin-2-one Chemical compound C1=C2C(C)=CC(=O)NC2=CC=C1OCCCN(CC1)CCC1CC1=CC=CC=C1 WEFCOUPECCVVSW-UHFFFAOYSA-N 0.000 description 4
- IFVGTHFTVSWJLP-UHFFFAOYSA-N 7-[3-(4-benzylpiperidin-1-yl)propoxy]-1-methyl-3,4-dihydroquinolin-2-one;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C2N(C)C(=O)CCC2=CC=C1OCCCN(CC1)CCC1CC1=CC=CC=C1 IFVGTHFTVSWJLP-UHFFFAOYSA-N 0.000 description 4
- 206010002091 Anaesthesia Diseases 0.000 description 4
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- PBWNNMXPKXZYAH-UHFFFAOYSA-N 4-methyl-6-[3-[4-(4-methylphenyl)piperidin-1-yl]propoxy]-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C1CCN(CCCOC=2C=C3C(C)=CC(=O)NC3=CC=2)CC1 PBWNNMXPKXZYAH-UHFFFAOYSA-N 0.000 description 3
- KVMMIMBZTYFQKN-UHFFFAOYSA-N 5-[3-(4-benzylpiperidin-1-yl)-2-hydroxypropoxy]-1-ethyl-3,4-dihydroquinolin-2-one;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC=C2N(CC)C(=O)CCC2=C1OCC(O)CN(CC1)CCC1CC1=CC=CC=C1 KVMMIMBZTYFQKN-UHFFFAOYSA-N 0.000 description 3
- XALBZKXYPFIRGO-UHFFFAOYSA-N 5-[3-(4-benzylpiperidin-1-yl)propoxy]-1-methyl-3,4-dihydroquinolin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2N(C)C(=O)CCC2=C1OCCCN(CC1)CCC1CC1=CC=CC=C1 XALBZKXYPFIRGO-UHFFFAOYSA-N 0.000 description 3
- JEPCGFOIQPTXTL-UHFFFAOYSA-N 5-[3-(4-benzylpiperidin-1-yl)propoxy]-1-prop-2-ynyl-3,4-dihydroquinolin-2-one;hydrate;hydrochloride Chemical compound O.Cl.C1=CC=C2N(CC#C)C(=O)CCC2=C1OCCCN(CC1)CCC1CC1=CC=CC=C1 JEPCGFOIQPTXTL-UHFFFAOYSA-N 0.000 description 3
- UTTJAIFHRUAFED-UHFFFAOYSA-N 5-hydroxy-3,4-dihydro-2(1h)-quinolinone Chemical compound N1C(=O)CCC2=C1C=CC=C2O UTTJAIFHRUAFED-UHFFFAOYSA-N 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 229920000084 Gum arabic Polymers 0.000 description 3
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000000205 acacia gum Substances 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- 230000001800 adrenalinergic effect Effects 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 210000005036 nerve Anatomy 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- WWNUOEHSLVYAIK-UHFFFAOYSA-N oxalic acid;7-[3-(4-phenylpiperidin-1-yl)propoxy]-1-(3-phenylpropyl)-3,4-dihydroquinolin-2-one Chemical compound OC(=O)C(O)=O.C1=C2N(CCCC=3C=CC=CC=3)C(=O)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC=C1 WWNUOEHSLVYAIK-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- XWUYPTBLYBFMST-UHFFFAOYSA-N (2-oxo-3,4-dihydro-1h-quinolin-5-yl) acetate Chemical compound N1C(=O)CCC2=C1C=CC=C2OC(=O)C XWUYPTBLYBFMST-UHFFFAOYSA-N 0.000 description 2
- MGGPPWUZJGYEMN-UHFFFAOYSA-N (8-bromo-2-oxo-3,4-dihydro-1h-quinolin-5-yl) acetate Chemical compound N1C(=O)CCC2=C1C(Br)=CC=C2OC(=O)C MGGPPWUZJGYEMN-UHFFFAOYSA-N 0.000 description 2
- GIGAGYBTGDSYMQ-UHFFFAOYSA-N 1-(3-chloro-2-methylpropyl)-4-phenylpiperidine Chemical compound C1CN(CC(CCl)C)CCC1C1=CC=CC=C1 GIGAGYBTGDSYMQ-UHFFFAOYSA-N 0.000 description 2
- PEXVQAFFEHJDBW-UHFFFAOYSA-N 1-(3-chloropropyl)-4-phenylpiperidine Chemical compound C1CN(CCCCl)CCC1C1=CC=CC=C1 PEXVQAFFEHJDBW-UHFFFAOYSA-N 0.000 description 2
- RKHWHRHOEKYEJW-UHFFFAOYSA-N 1-(4-phenylpiperidin-4-yl)ethanone Chemical compound C=1C=CC=CC=1C1(C(=O)C)CCNCC1 RKHWHRHOEKYEJW-UHFFFAOYSA-N 0.000 description 2
- IBPZEOLEURCSJU-UHFFFAOYSA-N 1-benzyl-5-[3-(4-benzylpiperidin-1-yl)-2-hydroxypropoxy]-3,4-dihydroquinolin-2-one;oxalic acid Chemical compound OC(=O)C(O)=O.C1CC(CC=2C=CC=CC=2)CCN1CC(O)COC(C=1CCC2=O)=CC=CC=1N2CC1=CC=CC=C1 IBPZEOLEURCSJU-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- ZIUFOCSWSPYALC-UHFFFAOYSA-N 4-phenyl-7-[3-(4-phenylpiperidin-1-yl)propoxy]-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C12=CC=C(OCCCN3CCC(CC3)C=3C=CC=CC=3)C=C2NC(=O)C=C1C1=CC=CC=C1 ZIUFOCSWSPYALC-UHFFFAOYSA-N 0.000 description 2
- KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 description 2
- JHWVAWUKMRXHCM-UHFFFAOYSA-N 5-(3-chloropropoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=CC=C2OCCCCl JHWVAWUKMRXHCM-UHFFFAOYSA-N 0.000 description 2
- BZEYZBGSCGYVKC-UHFFFAOYSA-N 5-[3-(4-acetyl-4-phenylpiperidin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CN(CCCOC=2C=3CCC(=O)NC=3C=CC=2)CCC1(C(=O)C)C1=CC=CC=C1 BZEYZBGSCGYVKC-UHFFFAOYSA-N 0.000 description 2
- BSPWGWDCIBOTLB-UHFFFAOYSA-N 5-[3-(4-benzylpiperidin-1-yl)-2-hydroxypropoxy]-1-prop-2-enyl-3,4-dihydroquinolin-2-one;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=CC=2N(CC=C)C(=O)CCC=2C=1OCC(O)CN(CC1)CCC1CC1=CC=CC=C1 BSPWGWDCIBOTLB-UHFFFAOYSA-N 0.000 description 2
- APZRSBHFLLLLKA-UHFFFAOYSA-N 5-[3-(4-benzylpiperidin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one;hydrochloride Chemical compound Cl.N1C(=O)CCC2=C1C=CC=C2OCCCN(CC1)CCC1CC1=CC=CC=C1 APZRSBHFLLLLKA-UHFFFAOYSA-N 0.000 description 2
- BFEQDZNCCKMXOP-UHFFFAOYSA-N 5-[3-(4-hydroxy-4-phenylpiperidin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CN(CCCOC=2C=3CCC(=O)NC=3C=CC=2)CCC1(O)C1=CC=CC=C1 BFEQDZNCCKMXOP-UHFFFAOYSA-N 0.000 description 2
- OGHVHWURQPBPBZ-UHFFFAOYSA-N 6,8-dichloro-5-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C(Cl)=CC(Cl)=C2O OGHVHWURQPBPBZ-UHFFFAOYSA-N 0.000 description 2
- FQZYZCHCPYTUFS-UHFFFAOYSA-N 6-[2-(4-acetyl-4-phenylpiperidin-1-yl)ethoxy]-1-methyl-3,4-dihydroquinolin-2-one Chemical compound C=1C=C2N(C)C(=O)CCC2=CC=1OCCN(CC1)CCC1(C(C)=O)C1=CC=CC=C1 FQZYZCHCPYTUFS-UHFFFAOYSA-N 0.000 description 2
- FBJDKEMXPBWZGJ-UHFFFAOYSA-N 6-[3-(4-acetyl-4-phenylpiperidin-1-yl)propoxy]-1-methyl-3,4-dihydroquinolin-2-one Chemical compound C=1C=C2N(C)C(=O)CCC2=CC=1OCCCN(CC1)CCC1(C(C)=O)C1=CC=CC=C1 FBJDKEMXPBWZGJ-UHFFFAOYSA-N 0.000 description 2
- XNLAGCRQVZPJBO-UHFFFAOYSA-N 6-[3-(4-benzylpiperidin-1-yl)propoxy]-4-methyl-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1=C2C(C)=CC(=O)NC2=CC=C1OCCCN(CC1)CCC1CC1=CC=CC=C1 XNLAGCRQVZPJBO-UHFFFAOYSA-N 0.000 description 2
- SNDVPRXDWDJUFV-UHFFFAOYSA-N 6-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-4-methyl-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1=C2C(C)=CC(=O)NC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 SNDVPRXDWDJUFV-UHFFFAOYSA-N 0.000 description 2
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- 239000008103 glucose Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 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 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 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
- 239000006187 pill Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- AQLYZDRHNHZHIS-UHFFFAOYSA-N quinoline-2,6-diol Chemical compound N1C(=O)C=CC2=CC(O)=CC=C21 AQLYZDRHNHZHIS-UHFFFAOYSA-N 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 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
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 230000002618 waking effect Effects 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
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12045279A JPS5643280A (en) | 1979-09-18 | 1979-09-18 | Carbostyril derivative |
| JP12556579A JPS5649360A (en) | 1979-09-28 | 1979-09-28 | 2-oxoquinoline derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3034237A1 DE3034237A1 (de) | 1981-04-16 |
| DE3034237C2 true DE3034237C2 (en, 2012) | 1988-04-21 |
Family
ID=26458032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803034237 Granted DE3034237A1 (de) | 1979-09-18 | 1980-09-11 | Carbostyrilderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende, antihistaminisch wirkende mittel |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4482560A (en, 2012) |
| AR (2) | AR230280A1 (en, 2012) |
| AT (1) | AT376972B (en, 2012) |
| AU (1) | AU518144B2 (en, 2012) |
| CA (1) | CA1151172A (en, 2012) |
| CH (1) | CH645892A5 (en, 2012) |
| DE (1) | DE3034237A1 (en, 2012) |
| DK (1) | DK158984C (en, 2012) |
| ES (1) | ES495163A0 (en, 2012) |
| FI (1) | FI76322C (en, 2012) |
| FR (1) | FR2465732A1 (en, 2012) |
| GB (1) | GB2063869B (en, 2012) |
| IT (1) | IT1129263B (en, 2012) |
| MX (1) | MX6806E (en, 2012) |
| NL (1) | NL187912C (en, 2012) |
| NO (1) | NO154841C (en, 2012) |
| PT (1) | PT71810B (en, 2012) |
| SE (1) | SE439632B (en, 2012) |
| SU (1) | SU1091857A3 (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2901336A1 (de) | 1979-01-15 | 1980-07-24 | Boehringer Mannheim Gmbh | Neue arylether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
| CH655110A5 (de) * | 1982-09-03 | 1986-03-27 | Otsuka Pharma Co Ltd | Carbostyrilderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten. |
| GB8426584D0 (en) * | 1984-10-19 | 1984-11-28 | Beecham Group Plc | Compounds |
| US4704390A (en) * | 1986-02-13 | 1987-11-03 | Warner-Lambert Company | Phenyl and heterocyclic tetrahydropyridyl alkoxy-benzheterocyclic compounds as antipsychotic agents |
| 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 |
| FR2620704B1 (fr) * | 1987-09-17 | 1991-04-26 | Sanofi Sa | Derives de (benzyl-4 piperidino)-1 propanol-2, leur preparation, leur utilisation comme antimicrobiens et les produits les contenant |
| US5227381A (en) * | 1988-05-02 | 1993-07-13 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivative |
| US5082847A (en) * | 1990-07-18 | 1992-01-21 | Syntex (U.S.A.) Inc. | Carbostyril compounds connected via an oxyalkyl group with a piperidine ring and having pharmaceutical utility |
| 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 |
| IT1264816B1 (it) * | 1993-07-28 | 1996-10-10 | Pergam Srl | Procedimento per la preparazione di derivati del procedimento per la preparazione di derivati del 3,4-diidrocarbostirile 3,4-diidrocarbostirile |
| ZA9610736B (en) | 1995-12-22 | 1997-06-27 | Warner Lambert Co | 2-Substituted piperidine analogs and their use as subtypeselective nmda receptor antagonists |
| ZA9610745B (en) * | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
| ZA9610738B (en) | 1995-12-22 | 1997-06-24 | Warner Lambert Co | Subtype selective nmda receptor ligands and the use thereof |
| EP1283199A4 (en) * | 2000-05-16 | 2003-12-17 | Takeda Chemical Industries Ltd | MELANINE CONCENTRATING HORMONE ANTAGONISTS |
| DK1480953T4 (da) † | 2003-01-09 | 2010-11-15 | Otsuka Pharma Co Ltd | Fremgangsmåde til fremstilling af aripiprazol |
| DE102008022221A1 (de) | 2008-05-06 | 2009-11-12 | Universität des Saarlandes | Inhibitoren der humanen Aldosteronsynthase CYP11B2 |
| US8541404B2 (en) | 2009-11-09 | 2013-09-24 | Elexopharm Gmbh | Inhibitors of the human aldosterone synthase CYP11B2 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3629266A (en) * | 1969-03-03 | 1971-12-21 | Miles Lab | (phenyl piperidino alkyl)3 4-dihydrocarbostyrils |
| JPS48103590A (en, 2012) * | 1972-04-13 | 1973-12-25 | ||
| US3910924A (en) * | 1972-04-13 | 1975-10-07 | Otsuka Pharma Co Ltd | 3,4-Dihydrocarbostyril derivatives and a process for preparing the same |
| US4256890A (en) * | 1972-09-14 | 1981-03-17 | Otsukapharmaceutical Co., Ltd. | 3,4-Dihydrocarbostyril derivatives and process for producing the same |
| JPS5239035B2 (en, 2012) * | 1972-12-14 | 1977-10-03 | ||
| JPS5310986B2 (en, 2012) * | 1974-02-05 | 1978-04-18 | ||
| JPS5310989B2 (en, 2012) * | 1974-04-25 | 1978-04-18 | ||
| 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 |
| JPS5919541B2 (ja) * | 1976-03-17 | 1984-05-07 | 大塚製薬株式会社 | 新規３，４−ジヒドロカルボスチリル誘導体 |
| CH619453A5 (en, 2012) * | 1976-03-17 | 1980-09-30 | Otsuka Pharma Co Ltd | |
| JPS609501B2 (ja) * | 1976-05-07 | 1985-03-11 | 大塚製薬株式会社 | 新規３，４−ジヒドロカルボスチリル誘導体 |
| US4210753A (en) * | 1976-03-17 | 1980-07-01 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compounds |
| DE2719562C2 (de) * | 1976-05-08 | 1986-05-07 | Otsuka Pharmaceutical Co. Ltd., Tokio/Tokyo | 3, 4-Dihydrocarbostyrilderivate, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten |
| JPS6019295B2 (ja) * | 1977-03-04 | 1985-05-15 | 大塚製薬株式会社 | カルボスチリル誘導体及びその製造法 |
| JPS5416478A (en) * | 1977-07-08 | 1979-02-07 | Otsuka Pharmaceut Co Ltd | 3,4-dihydrocarbostyril herivative |
| JPS54130587A (en) * | 1978-03-30 | 1979-10-09 | Otsuka Pharmaceut Co Ltd | Carbostyryl derivative |
| DE2827566A1 (de) * | 1978-06-23 | 1980-01-10 | Boehringer Mannheim Gmbh | 1,2-dihydro-chinolin-2-on-derivate und verfahren zu ihrer herstellung |
| JPS5589221A (en) * | 1978-12-28 | 1980-07-05 | Otsuka Pharmaceut Co Ltd | Antihistaminic agent |
| JPS5589222A (en) * | 1978-12-28 | 1980-07-05 | Otsuka Pharmaceut Co Ltd | Antihistaminic agent |
| DE2901336A1 (de) * | 1979-01-15 | 1980-07-24 | Boehringer Mannheim Gmbh | Neue arylether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
-
1980
- 1980-09-11 DE DE19803034237 patent/DE3034237A1/de active Granted
- 1980-09-12 AU AU62381/80A patent/AU518144B2/en not_active Ceased
- 1980-09-12 FR FR8019708A patent/FR2465732A1/fr active Granted
- 1980-09-16 FI FI802905A patent/FI76322C/fi not_active IP Right Cessation
- 1980-09-16 SU SU802982853A patent/SU1091857A3/ru active
- 1980-09-17 NO NO802762A patent/NO154841C/no unknown
- 1980-09-17 CA CA000360402A patent/CA1151172A/en not_active Expired
- 1980-09-17 DK DK394080A patent/DK158984C/da active
- 1980-09-17 AR AR282565A patent/AR230280A1/es active
- 1980-09-17 AT AT0465780A patent/AT376972B/de not_active IP Right Cessation
- 1980-09-17 PT PT71810A patent/PT71810B/pt unknown
- 1980-09-17 SE SE8006498A patent/SE439632B/sv not_active IP Right Cessation
- 1980-09-17 NL NLAANVRAGE8005188,A patent/NL187912C/xx not_active IP Right Cessation
- 1980-09-17 CH CH694080A patent/CH645892A5/de not_active IP Right Cessation
- 1980-09-18 IT IT68445/80A patent/IT1129263B/it active
- 1980-09-18 MX MX809034U patent/MX6806E/es unknown
- 1980-09-18 GB GB8030207A patent/GB2063869B/en not_active Expired
- 1980-09-18 ES ES495163A patent/ES495163A0/es active Granted
-
1982
- 1982-03-12 US US06/357,769 patent/US4482560A/en not_active Expired - Fee Related
- 1982-05-18 AR AR289431A patent/AR230059A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| MX6806E (es) | 1986-07-30 |
| US4482560A (en) | 1984-11-13 |
| NO154841B (no) | 1986-09-22 |
| AR230059A1 (es) | 1984-02-29 |
| DK394080A (da) | 1981-03-19 |
| PT71810A (en) | 1980-10-01 |
| GB2063869B (en) | 1983-05-25 |
| SU1091857A3 (ru) | 1984-05-07 |
| NL187912B (nl) | 1991-09-16 |
| FI802905A7 (fi) | 1981-03-19 |
| SE8006498L (sv) | 1981-03-19 |
| CH645892A5 (de) | 1984-10-31 |
| IT8068445A0 (it) | 1980-09-18 |
| NL8005188A (nl) | 1981-03-20 |
| ES8200679A1 (es) | 1981-11-16 |
| DK158984C (da) | 1991-01-14 |
| CA1151172A (en) | 1983-08-02 |
| NL187912C (nl) | 1992-02-17 |
| AU6238180A (en) | 1981-05-28 |
| AU518144B2 (en) | 1981-09-17 |
| AR230280A1 (es) | 1984-03-01 |
| DE3034237A1 (de) | 1981-04-16 |
| NO154841C (no) | 1987-01-07 |
| ES495163A0 (es) | 1981-11-16 |
| IT1129263B (it) | 1986-06-04 |
| SE439632B (sv) | 1985-06-24 |
| DK158984B (da) | 1990-08-13 |
| FR2465732A1 (fr) | 1981-03-27 |
| ATA465780A (de) | 1984-06-15 |
| FI76322B (fi) | 1988-06-30 |
| NO802762L (no) | 1981-03-19 |
| AT376972B (de) | 1985-01-25 |
| GB2063869A (en) | 1981-06-10 |
| PT71810B (en) | 1981-07-07 |
| FR2465732B1 (en, 2012) | 1983-06-24 |
| FI76322C (fi) | 1988-10-10 |
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