JPS6325585B2 - - Google Patents

Info

Publication number: JPS6325585B2
Authority: JP; Japan
Prior art keywords: group; dihydrocarbostyryl; piperazinyl; butyl; oxo
Prior art date: 1980-03-06
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

Application number

JP55028805A

Other languages

English (en)

Japanese (ja)

Other versions

JPS56125370A (en

Inventor

Kazuhisa Sakano

Takafumi Fujioka

Masaaki Oosaki

Kazuyuki Nakagawa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Otsuka Pharmaceutical Co Ltd

Original Assignee

Otsuka Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1980-03-06

Filing date

1980-03-06

Publication date

1988-05-26

1980-03-06 Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd

1980-03-06 Priority to JP2880580A priority Critical patent/JPS56125370A/ja

1981-02-25 Priority to PH25264A priority patent/PH17194A/en

1981-02-27 Priority to DE19813107601 priority patent/DE3107601A1/de

1981-02-27 Priority to CA000371904A priority patent/CA1155119A/en

1981-02-27 Priority to DE3152880A priority patent/DE3152880C2/de

1981-03-02 Priority to AU67973/81A priority patent/AU523005B2/en

1981-03-03 Priority to FI810669A priority patent/FI76323C/fi

1981-03-03 Priority to AT0098481A priority patent/AT381307B/de

1981-03-04 Priority to CH1446/81A priority patent/CH647775A5/de

1981-03-04 Priority to SU813257001A priority patent/SU1367857A3/ru

1981-03-04 Priority to FR8104311A priority patent/FR2477542A1/fr

1981-03-04 Priority to ZA00811438A priority patent/ZA811438B/xx

1981-03-05 Priority to ES500137A priority patent/ES8301962A1/es

1981-03-05 Priority to PT72622A priority patent/PT72622B/pt

1981-03-05 Priority to DK099781A priority patent/DK155282C/da

1981-03-05 Priority to IT67311/81A priority patent/IT1144315B/it

1981-03-05 Priority to NO810765A priority patent/NO159531C/no

1981-03-05 Priority to BE0/204016A priority patent/BE887800A/fr

1981-03-05 Priority to SE8101409A priority patent/SE447255B/sv

1981-03-06 Priority to NLAANVRAGE8101099,A priority patent/NL184364C/xx

1981-03-06 Priority to MX819337U priority patent/MX6980E/es

1981-03-06 Priority to GB8107036A priority patent/GB2071094B/en

1981-10-01 Publication of JPS56125370A publication Critical patent/JPS56125370A/ja

1982-02-16 Priority to ES509659A priority patent/ES509659A0/es

1982-02-16 Priority to ES509658A priority patent/ES8305356A1/es

1982-03-18 Priority to SU823406699A priority patent/RU1779249C/ru

1982-04-07 Priority to US06/366,336 priority patent/US4567187A/en

1982-04-07 Priority to US06/366,335 priority patent/US4455422A/en

1982-04-07 Priority to US06/366,337 priority patent/US4460593A/en

1982-12-29 Priority to ES518667A priority patent/ES8405782A1/es

1983-03-09 Priority to US06/473,641 priority patent/US4619932A/en

1984-02-17 Priority to AT0054184A priority patent/AT387215B/de

1988-05-26 Publication of JPS6325585B2 publication Critical patent/JPS6325585B2/ja

1988-09-09 Priority to NLAANVRAGE8802223,A priority patent/NL187209C/xx

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 221
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 33
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 28
238000000034 method Methods 0.000 claims description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
125000005606 carbostyryl group Chemical group 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000005530 alkylenedioxy group Chemical group 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 7
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
229910052796 boron Inorganic materials 0.000 claims description 3
150000004885 piperazines Chemical class 0.000 claims description 2
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
125000004193 piperazinyl group Chemical group 0.000 description 372
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 301
238000002844 melting Methods 0.000 description 147
230000008018 melting Effects 0.000 description 147
239000013078 crystal Substances 0.000 description 130
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 123
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 117
-1 4-phenylbutyl Chemical group 0.000 description 112
238000006243 chemical reaction Methods 0.000 description 100
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 88
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 78
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
235000019441 ethanol Nutrition 0.000 description 50
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 42
239000000047 product Substances 0.000 description 39
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
101710088194 Dehydrogenase Proteins 0.000 description 33
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 28
238000000354 decomposition reaction Methods 0.000 description 27
238000003756 stirring Methods 0.000 description 27
238000006356 dehydrogenation reaction Methods 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
239000000843 powder Substances 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
239000003795 chemical substances by application Substances 0.000 description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
241000699670 Mus sp. Species 0.000 description 17
238000000921 elemental analysis Methods 0.000 description 17
239000007858 starting material Substances 0.000 description 17
239000012442 inert solvent Substances 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
239000002904 solvent Substances 0.000 description 16
239000000203 mixture Substances 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
239000010410 layer Substances 0.000 description 14
239000000739 antihistaminic agent Substances 0.000 description 13
239000003826 tablet Substances 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
239000003814 drug Substances 0.000 description 12
230000000694 effects Effects 0.000 description 12
238000006722 reduction reaction Methods 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
239000012279 sodium borohydride Substances 0.000 description 12
229910000033 sodium borohydride Inorganic materials 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 11
239000003874 central nervous system depressant Substances 0.000 description 11
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
238000010531 catalytic reduction reaction Methods 0.000 description 10
239000012141 concentrate Substances 0.000 description 10
235000008504 concentrate Nutrition 0.000 description 10
235000011121 sodium hydroxide Nutrition 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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 9
230000001387 anti-histamine Effects 0.000 description 9
238000010992 reflux Methods 0.000 description 9
235000002639 sodium chloride Nutrition 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 8
229940079593 drug Drugs 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
235000011181 potassium carbonates Nutrition 0.000 description 8
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 7
229920002472 Starch Polymers 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
239000003638 chemical reducing agent Substances 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 7
WGXZDYPGLJYBJW-UHFFFAOYSA-N chloroform;propan-2-ol Chemical compound CC(C)O.ClC(Cl)Cl WGXZDYPGLJYBJW-UHFFFAOYSA-N 0.000 description 7
150000002170 ethers Chemical class 0.000 description 7
239000008101 lactose Substances 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
235000009518 sodium iodide Nutrition 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
239000008107 starch Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
150000007514 bases Chemical class 0.000 description 6
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 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
230000001603 reducing effect Effects 0.000 description 6
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 5
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
229920000084 Gum arabic Polymers 0.000 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
235000010489 acacia gum Nutrition 0.000 description 5
239000000205 acacia gum Substances 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
235000001727 glucose Nutrition 0.000 description 5
239000008103 glucose Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
229960001252 methamphetamine Drugs 0.000 description 5
239000012452 mother liquor Substances 0.000 description 5
238000012746 preparative thin layer chromatography Methods 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
235000017550 sodium carbonate Nutrition 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
239000008096 xylene Substances 0.000 description 5
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 4
229930182837 (R)-adrenaline Natural products 0.000 description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
244000215068 Acacia senegal Species 0.000 description 4
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
229940125715 antihistaminic agent Drugs 0.000 description 4
230000006399 behavior Effects 0.000 description 4
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
239000000969 carrier Substances 0.000 description 4
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
229960005139 epinephrine Drugs 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
230000001939 inductive effect Effects 0.000 description 4
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 4
239000006187 pill Substances 0.000 description 4
239000011736 potassium bicarbonate Substances 0.000 description 4
235000015497 potassium bicarbonate Nutrition 0.000 description 4
229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
229940086066 potassium hydrogencarbonate Drugs 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
238000005303 weighing Methods 0.000 description 4
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 description 3
WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
206010002091 Anaesthesia Diseases 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
208000003251 Pruritus Diseases 0.000 description 3
241000700159 Rattus Species 0.000 description 3
239000002262 Schiff base Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
230000037005 anaesthesia Effects 0.000 description 3
150000001448 anilines Chemical class 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
239000008120 corn starch Substances 0.000 description 3
229940099112 cornstarch Drugs 0.000 description 3
238000006264 debenzylation reaction Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
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UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
230000000881 depressing effect Effects 0.000 description 1
229940039227 diagnostic agent Drugs 0.000 description 1
239000000032 diagnostic agent Substances 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
GUBNMFJOJGDCEL-UHFFFAOYSA-N dicyclomine hydrochloride Chemical group [Cl-].C1CCCCC1C1(C(=O)OCC[NH+](CC)CC)CCCCC1 GUBNMFJOJGDCEL-UHFFFAOYSA-N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000036267 drug metabolism Effects 0.000 description 1
230000002497 edematous effect Effects 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
239000002662 enteric coated tablet Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000010931 ester hydrolysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
239000003906 humectant Substances 0.000 description 1
239000008172 hydrogenated vegetable oil Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
230000007803 itching Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000006742 locomotor activity Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
229960003511 macrogol Drugs 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
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
XNOQMJHXLYCQKI-UHFFFAOYSA-N n-(4-bromophenyl)nitramide Chemical compound [O-][N+](=O)NC1=CC=C(Br)C=C1 XNOQMJHXLYCQKI-UHFFFAOYSA-N 0.000 description 1
208000010753 nasal discharge Diseases 0.000 description 1
239000002547 new drug Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
229940043274 prophylactic drug Drugs 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000028527 righting reflex Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
206010040400 serum sickness Diseases 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
235000020374 simple syrup Nutrition 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
230000004627 sleep-enhancing effect Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000003419 tautomerization reaction Methods 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
229940126585 therapeutic drug Drugs 0.000 description 1
230000035922 thirst Effects 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
239000000080 wetting agent Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

JP2880580A 1980-03-06 1980-03-06 Carbostyril derivative Granted JPS56125370A (en)

Priority Applications (32)

Application Number	Priority Date	Filing Date	Title
JP2880580A JPS56125370A (en)	1980-03-06	1980-03-06	Carbostyril derivative
PH25264A PH17194A (en)	1980-03-06	1981-02-25	Novel carbostyril derivatives,and pharmaceutical composition containing the same
DE19813107601 DE3107601A1 (de)	1980-03-06	1981-02-27	Neue carbostyrilderivate, verfahren zu deren herstellung und pharmazeutische verbindungen, welche diese enthalten
CA000371904A CA1155119A (en)	1980-03-06	1981-02-27	Carbostyril derivatives, process for producing thereof and pharmaceutical composition containing the same
DE3152880A DE3152880C2 (no)	1980-03-06	1981-02-27
AU67973/81A AU523005B2 (en)	1980-03-06	1981-03-02	Carbostyril derivatives
FI810669A FI76323C (fi)	1980-03-06	1981-03-03	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara karbostyrilderivat.
AT0098481A AT381307B (de)	1980-03-06	1981-03-03	Verfahren zum herstellen neuer carbostyrilderivate und ihrer pharmazeutisch annehmbaren salze
CH1446/81A CH647775A5 (de)	1980-03-06	1981-03-04	Basisch substituierte carbostyrilderivate und diese enthaltende pharmazeutische zusammensetzungen.
SU813257001A SU1367857A3 (ru)	1980-03-06	1981-03-04	Способ получени карбостирильных производных
FR8104311A FR2477542A1 (fr)	1980-03-06	1981-03-04	Derives de carbostyrile, leurs procedes de preparation et leur application en therapeutique
ZA00811438A ZA811438B (en)	1980-03-06	1981-03-04	Carbostyril derivatives, process for producing thereof and pharmaceutica composition containing the same
BE0/204016A BE887800A (fr)	1980-03-06	1981-03-05	Derives de carbostyrile, leurs procedes de preparation et leur application en therapeutique
PT72622A PT72622B (en)	1980-03-06	1981-03-05	Novel carbostyril derivatives process for producing thereof and pharmaceutical composition containing the same
DK099781A DK155282C (da)	1980-03-06	1981-03-05	Analogifremgangsmaade til fremstilling af carbostyrilderivater
IT67311/81A IT1144315B (it)	1980-03-06	1981-03-05	Derivati carbostirilici procedimento per la loro preparazione e composizioni farmaceutiche contenenti tali derivati
NO810765A NO159531C (no)	1980-03-06	1981-03-05	Analogifremgangsmaate for fremstilling av farmasoeytisk aktive karbostyrilderivater.
ES500137A ES8301962A1 (es)	1980-03-06	1981-03-05	Un procedimiento para la produccion de un derivado de carboslivilo.
SE8101409A SE447255B (sv)	1980-03-06	1981-03-05	Karbostyrilderivat och forfarande for framstellning derav
NLAANVRAGE8101099,A NL184364C (nl)	1980-03-06	1981-03-06	Carbostyrilderivaten en zouten daarvan, alsmede gevormd farmaceutisch preparaat dat een of meer van dergelijke carbostyrilverbindingen bevat.
MX819337U MX6980E (es)	1980-03-06	1981-03-06	Procedimiento para la produccion de derivados de carboestirilo
GB8107036A GB2071094B (en)	1980-03-06	1981-03-06	Carbostyril derivatives processes for their production andpharmaceutical composition containing them
ES509658A ES8305356A1 (es)	1980-03-06	1982-02-16	Un procedimiento para la produccion de un derivado de carbostirilo
ES509659A ES509659A0 (es)	1980-03-06	1982-02-16	Un procedimiento para la produccion de un derivado de carbostirilo
SU823406699A RU1779249C (ru)	1980-03-06	1982-03-18	Способ получени карбостириловых производных (его вариант)
US06/366,336 US4567187A (en)	1980-03-06	1982-04-07	Carbostyril derivatives and antihistaminic agents containing the carbostyril derivatives
US06/366,335 US4455422A (en)	1980-03-06	1982-04-07	Carbostyril derivatives and pharmaceutical composition containing the same
US06/366,337 US4460593A (en)	1980-03-06	1982-04-07	Carbostyril derivatives, and central nervous system controlling agents containing the carbostyril derivatives
ES518667A ES8405782A1 (es)	1980-03-06	1982-12-29	Un procedimiento para la produccion de un derivado de carbostirilo.
US06/473,641 US4619932A (en)	1980-03-06	1983-03-09	Novel carbostyril derivatives, process for producing thereof and pharmaceutical composition containing the same
AT0054184A AT387215B (de)	1980-03-06	1984-02-17	Verfahren zum herstellen neuer carbostyrilderivate und ihrer salze
NLAANVRAGE8802223,A NL187209C (nl)	1980-03-06	1988-09-09	Carbostyrilderivaten, alsmede farmaceutisch preparaat dat een of meer van dergelijke carbostyrilderivaten bevat.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2880580A JPS56125370A (en)	1980-03-06	1980-03-06	Carbostyril derivative

Publications (2)

Publication Number	Publication Date
JPS56125370A JPS56125370A (en)	1981-10-01
JPS6325585B2 true JPS6325585B2 (no)	1988-05-26

Family

ID=12258630

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2880580A Granted JPS56125370A (en)	1980-03-06	1980-03-06	Carbostyril derivative

Country Status (2)

Country	Link
JP (1)	JPS56125370A (no)
ZA (1)	ZA811438B (no)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0249769A (ja) *	1989-06-26	1990-02-20	Otsuka Pharmaceut Co Ltd	カルボスチリル誘導体
GB0227240D0 (en) *	2002-11-21	2002-12-31	Glaxo Group Ltd	Compounds
CN106608875A (zh) *	2015-10-26	2017-05-03	江苏恩华药业股份有限公司	一种稠和杂环类衍生物合成及其应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5416478A (en) *	1977-07-08	1979-02-07	Otsuka Pharmaceut Co Ltd	3,4-dihydrocarbostyril herivative

1980
- 1980-03-06 JP JP2880580A patent/JPS56125370A/ja active Granted
1981
- 1981-03-04 ZA ZA00811438A patent/ZA811438B/xx unknown

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5416478A (en) *	1977-07-08	1979-02-07	Otsuka Pharmaceut Co Ltd	3,4-dihydrocarbostyril herivative

Also Published As

Publication number	Publication date
ZA811438B (en)	1982-03-31
JPS56125370A (en)	1981-10-01

Publication	Publication Date	Title
US4455422A (en)	1984-06-19	Carbostyril derivatives and pharmaceutical composition containing the same
JP2608788B2 (ja)	1997-05-14	精神***病治療剤
JPH0586391B2 (no)	1993-12-10
JPH0314308B2 (no)	1991-02-26
JPH0550512B2 (no)	1993-07-29
EP0257864B1 (en)	1990-12-05	Antiarrhythmic agents
JPS6320226B2 (no)	1988-04-26
JPH0568476B2 (no)	1993-09-29
JPH0314023B2 (no)	1991-02-25
SK1897A3 (en)	1997-08-06	Benzamidines, its preparation, pharmaceutical composition containing them and their use
JPH0212204B2 (no)	1990-03-19
KR900003650B1 (ko)	1990-05-28	(1h-테트라졸-5-일)-2(1h)-퀴놀리논, 나프티리디논 및 그의 제조방법
CA2735417A1 (en)	2010-03-18	Glucocorticoid receptor agonist comprising novel 1,2,3,4-tetrahydroquinoxaline derivatives containing phenyl group having sulfonic acid ester structure introduced therein as substituent
JPH0215537B2 (no)	1990-04-12
JPS6325585B2 (no)	1988-05-26
EP0083222A1 (en)	1983-07-06	New quinolylacetic acid compounds and pharmaceutical compositions containing them
US4798832A (en)	1989-01-17	Pyrido[1,2-a]pyrimidine compounds, corresponding intermediates and use as SRS-A antagonists
KR850000024B1 (ko)	1985-02-11	카르보스티릴 유도체의 제조방법
JPS6331445B2 (no)	1988-06-23
JPH0216299B2 (no)	1990-04-16
KR820002231B1 (ko)	1982-12-03	신규 카르보스티릴 유도체의 제조방법
JPS647968B2 (no)	1989-02-10
JPH0351687B2 (no)	1991-08-07
JPS6341387B2 (no)	1988-08-17
KR860001958B1 (ko)	1986-11-05	카보스티릴 화합물의 제조방법