DE2912105C2 - Neue carbostyrilderivate, verfahren zu deren herstellung und diese enthaltende mittel - Google Patents

Neue carbostyrilderivate, verfahren zu deren herstellung und diese enthaltende mittel

Info

Publication number: DE2912105C2
Authority: DE; Germany
Prior art keywords: crystals; group; propoxy; colorless; dihydrocarbostyril
Prior art date: 1978-03-30
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

DE2912105A

Other languages

German (de)

English (en)

Other versions

DE2912105A1 (de

Inventor

Kazuo Banno

Takafumi Fujioka

Kazuyuki Tokushima Nakagawa

Yasuo Oshiro

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.)

1978-03-30

Filing date

1979-03-27

Publication date

1985-08-29

1979-03-27 Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd

1979-10-11 Publication of DE2912105A1 publication Critical patent/DE2912105A1/de

1985-08-29 Application granted granted Critical

1985-08-29 Publication of DE2912105C2 publication Critical patent/DE2912105C2/de

Status Expired legal-status Critical Current

Links

LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims description 56
238000000034 method Methods 0.000 title claims description 45
238000004519 manufacturing process Methods 0.000 title description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 454
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 221
-1 3,4,5-trimethoxy benzoyloxy group Chemical group 0.000 claims description 141
150000001875 compounds Chemical class 0.000 claims description 101
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 69
239000003795 chemical substances by application Substances 0.000 claims description 40
125000004432 carbon atom Chemical group C* 0.000 claims description 29
125000005843 halogen group Chemical group 0.000 claims description 21
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 7
241001233037 catfish Species 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
230000002140 halogenating effect Effects 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
238000006467 substitution reaction Methods 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
101150065749 Churc1 gene Proteins 0.000 claims description 2
102100038239 Protein Churchill Human genes 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 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
241000272517 Anseriformes Species 0.000 claims 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
239000005977 Ethylene Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
125000000542 sulfonic acid group Chemical group 0.000 claims 1
239000013078 crystal Substances 0.000 description 455
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 198
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 148
238000002844 melting Methods 0.000 description 85
230000008018 melting Effects 0.000 description 85
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 72
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 71
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 67
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 62
239000000243 solution Substances 0.000 description 56
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 53
125000004193 piperazinyl group Chemical group 0.000 description 48
239000011541 reaction mixture Substances 0.000 description 48
238000006243 chemical reaction Methods 0.000 description 46
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
238000001914 filtration Methods 0.000 description 31
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
238000000354 decomposition reaction Methods 0.000 description 30
238000004821 distillation Methods 0.000 description 27
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 27
238000010992 reflux Methods 0.000 description 24
230000000694 effects Effects 0.000 description 22
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 20
238000001953 recrystallisation Methods 0.000 description 20
241000699670 Mus sp. Species 0.000 description 17
TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 16
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 16
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
235000017557 sodium bicarbonate Nutrition 0.000 description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
235000011121 sodium hydroxide Nutrition 0.000 description 13
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
150000007514 bases Chemical class 0.000 description 12
238000001816 cooling Methods 0.000 description 12
239000010410 layer Substances 0.000 description 12
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 11
239000002904 solvent Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 10
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 10
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 10
229940086542 triethylamine Drugs 0.000 description 10
241000699666 Mus <mouse, genus> Species 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 9
239000012442 inert solvent Substances 0.000 description 9
150000004682 monohydrates Chemical class 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
235000009518 sodium iodide Nutrition 0.000 description 9
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
239000008096 xylene Substances 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
235000011181 potassium carbonates Nutrition 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
235000017550 sodium carbonate Nutrition 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
210000003169 central nervous system Anatomy 0.000 description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
238000005303 weighing Methods 0.000 description 6
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 4
IEMFRASHQUBMQP-UHFFFAOYSA-N 6-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCC(O)CN(CC1)CCN1C1=CC=CC=C1 IEMFRASHQUBMQP-UHFFFAOYSA-N 0.000 description 4
QBLRMOJWUWFFOU-UHFFFAOYSA-N 6-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCC(O)CN(CC1)CCN1C1=CC=CC=C1 QBLRMOJWUWFFOU-UHFFFAOYSA-N 0.000 description 4
244000215068 Acacia senegal Species 0.000 description 4
206010002091 Anaesthesia Diseases 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
229920000084 Gum arabic Polymers 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000000205 acacia gum Substances 0.000 description 4
235000010489 acacia gum Nutrition 0.000 description 4
230000037396 body weight Effects 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
150000004683 dihydrates Chemical class 0.000 description 4
239000003814 drug Substances 0.000 description 4
AWISGSJZNFRYNE-UHFFFAOYSA-N ethanol;dihydrochloride Chemical compound Cl.Cl.CCO AWISGSJZNFRYNE-UHFFFAOYSA-N 0.000 description 4
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
229960003878 haloperidol Drugs 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
210000003405 ileum Anatomy 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
CIZJPPDMQJRHQT-UHFFFAOYSA-N 1-benzyl-7-[3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydroquinolin-2-one Chemical compound C1=C2N(CC=3C=CC=CC=3)C(=O)CCC2=CC=C1OCCCN(CC1)CCN1C1=CC=CC=C1 CIZJPPDMQJRHQT-UHFFFAOYSA-N 0.000 description 3
ZUGRYLJRHKHZLR-UHFFFAOYSA-N 1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)C=CC2=C1 ZUGRYLJRHKHZLR-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 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
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
RRBYJBJQLCHSIT-UHFFFAOYSA-N 7-[3-(4-benzylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2NC(=O)CCC2=CC=C1OCCCN(CC1)CCN1CC1=CC=CC=C1 RRBYJBJQLCHSIT-UHFFFAOYSA-N 0.000 description 3
MWBDVKHHXQNPOO-UHFFFAOYSA-N 8-[3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=12NC(=O)CCC2=CC=CC=1OCCCN(CC1)CCN1C1=CC=CC=C1 MWBDVKHHXQNPOO-UHFFFAOYSA-N 0.000 description 3
LTUWYBFZTRXBPB-UHFFFAOYSA-N 8-bromo-6-chloro-7-[3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound ClC1=CC=2CCC(=O)NC=2C(Br)=C1OCCCN(CC1)CCN1C1=CC=CC=C1 LTUWYBFZTRXBPB-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
230000037005 anaesthesia Effects 0.000 description 3
230000003444 anaesthetic effect Effects 0.000 description 3
230000000202 analgesic effect Effects 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
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
229940079593 drug Drugs 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
229960003132 halothane Drugs 0.000 description 3
BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
YZGRCIMYJXKBAW-UHFFFAOYSA-N 1-hexyl-7-[3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydroquinolin-2-one Chemical compound C1=C2N(CCCCCC)C(=O)CCC2=CC=C1OCCCN(CC1)CCN1C1=CC=CC=C1 YZGRCIMYJXKBAW-UHFFFAOYSA-N 0.000 description 2
125000005999 2-bromoethyl group Chemical group 0.000 description 2
ZDMQTPPAJCUOQG-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2NC(=O)CCC2=C1 ZDMQTPPAJCUOQG-UHFFFAOYSA-N 0.000 description 2
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
HKTZKESTBBPIET-UHFFFAOYSA-N 5-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=CC=2NC(=O)CCC=2C=1OCC(O)CN(CC1)CCN1C1=CC=CC=C1 HKTZKESTBBPIET-UHFFFAOYSA-N 0.000 description 2
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000036640 muscle relaxation Effects 0.000 description 1
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229960002748 norepinephrine Drugs 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
229960001412 pentobarbital Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000002504 physiological saline solution Substances 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
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
239000012495 reaction gas Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
230000004622 sleep time Effects 0.000 description 1
230000004623 sleep-prolonging effect Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid 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
150000003512 tertiary amines Chemical class 0.000 description 1
239000010409 thin film Substances 0.000 description 1
230000035922 thirst Effects 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 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
230000008673 vomiting Effects 0.000 description 1
230000002618 waking effect Effects 0.000 description 1
239000000080 wetting agent Substances 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
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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
- 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
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Immunology (AREA)
Anesthesiology (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DE2912105A 1978-03-30 1979-03-27 Neue carbostyrilderivate, verfahren zu deren herstellung und diese enthaltende mittel Expired DE2912105C2 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3778378A JPS54130587A (en)	1978-03-30	1978-03-30	Carbostyryl derivative

Publications (2)

Publication Number	Publication Date
DE2912105A1 DE2912105A1 (de)	1979-10-11
DE2912105C2 true DE2912105C2 (de)	1985-08-29

Family

ID=12507080

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DE2912105A Expired DE2912105C2 (de)	1978-03-30	1979-03-27	Neue carbostyrilderivate, verfahren zu deren herstellung und diese enthaltende mittel
DE2953723A Expired DE2953723C2 (de)	1978-03-30	1979-03-27	Neue carbostyrilderivate, verfahren zu deren herstellung und diese enthaltende mittel

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DE2953723A Expired DE2953723C2 (de)	1978-03-30	1979-03-27	Neue carbostyrilderivate, verfahren zu deren herstellung und diese enthaltende mittel

Country Status (21)

Country	Link
US (2)	US4734416A (2)
JP (1)	JPS54130587A (2)
AT (1)	AT376432B (2)
AU (1)	AU515531B2 (2)
BE (1)	BE875174A (2)
CA (1)	CA1117110A (2)
CH (2)	CH641455A5 (2)
DE (2)	DE2912105C2 (2)
DK (1)	DK158225C (2)
ES (4)	ES479134A1 (2)
FI (1)	FI70704C (2)
FR (1)	FR2421174A1 (2)
GB (1)	GB2017701B (2)
IT (1)	IT1119284B (2)
MX (1)	MX5862E (2)
NL (1)	NL183189C (2)
NO (1)	NO151321C (2)
PT (1)	PT69422A (2)
SE (1)	SE434945B (2)
SU (2)	SU1140687A3 (2)
ZA (1)	ZA791516B (2)

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1978
- 1978-03-30 JP JP3778378A patent/JPS54130587A/ja active Granted
1979
- 1979-03-27 DE DE2912105A patent/DE2912105C2/de not_active Expired
- 1979-03-27 DE DE2953723A patent/DE2953723C2/de not_active Expired
- 1979-03-27 CA CA000324227A patent/CA1117110A/en not_active Expired
- 1979-03-28 AU AU45480/79A patent/AU515531B2/en not_active Expired
- 1979-03-28 US US06/024,602 patent/US4734416A/en not_active Expired - Lifetime
- 1979-03-28 FI FI791034A patent/FI70704C/fi not_active IP Right Cessation
- 1979-03-29 NO NO791049A patent/NO151321C/no unknown
- 1979-03-29 CH CH295379A patent/CH641455A5/de not_active IP Right Cessation
- 1979-03-29 DK DK128679A patent/DK158225C/da not_active IP Right Cessation
- 1979-03-29 BE BE0/194281A patent/BE875174A/xx not_active IP Right Cessation
- 1979-03-29 AT AT0235179A patent/AT376432B/de not_active IP Right Cessation
- 1979-03-29 SE SE7902794A patent/SE434945B/sv not_active IP Right Cessation
- 1979-03-29 FR FR7907863A patent/FR2421174A1/fr active Granted
- 1979-03-29 SU SU792745704A patent/SU1140687A3/ru active
- 1979-03-30 ZA ZA791516A patent/ZA791516B/xx unknown
- 1979-03-30 PT PT69422A patent/PT69422A/pt unknown
- 1979-03-30 NL NLAANVRAGE7902514,A patent/NL183189C/xx not_active IP Right Cessation
- 1979-03-30 ES ES479134A patent/ES479134A1/es not_active Expired
- 1979-03-30 GB GB7911155A patent/GB2017701B/en not_active Expired
- 1979-03-30 IT IT67674/79A patent/IT1119284B/it active
- 1979-03-30 MX MX797848U patent/MX5862E/es unknown
- 1979-12-17 ES ES486990A patent/ES486990A1/es not_active Expired
- 1979-12-17 ES ES486992A patent/ES486992A1/es not_active Expired
- 1979-12-17 ES ES486991A patent/ES486991A1/es not_active Expired
1981
- 1981-09-08 SU SU813328599A patent/SU1232144A3/ru active
1982
- 1982-03-26 CH CH190082A patent/CH641350A5/de not_active IP Right Cessation
1987
- 1987-03-12 US US07/025,193 patent/US4824840A/en not_active Expired - Lifetime

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US8703773B2 (en)	2001-09-25	2014-04-22	Otsuka Pharmaceutical Co., Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation thereof
US8703772B2 (en)	2001-09-25	2014-04-22	Otsuka Pharmaceutical Co., Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation thereof
US8642760B2 (en)	2001-09-25	2014-02-04	Otsuka Pharmaceutical Co., Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation thereof
US8901303B2 (en)	2001-09-25	2014-12-02	Otsuka Pharmaceutical Co., Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation thereof
US8901130B2 (en)	2001-09-25	2014-12-02	Ostuka Pharmaceutical Co., Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation
US8993761B2 (en)	2001-09-25	2015-03-31	Otsuka Pharamceutical Co. Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation thereof
US7910589B2 (en)	2001-09-25	2011-03-22	Otsuka Pharmaceutical Co., Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation thereof
US8399469B2 (en)	2001-09-25	2013-03-19	Otsuka Pharmaceutical Co., Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation thereof
US9359302B2 (en)	2001-09-25	2016-06-07	Otsuka Pharmaceutical Co., Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation thereof
US8017615B2 (en)	2001-09-25	2011-09-13	Otsuka Pharmaceutical Co., Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation thereof
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Also Published As

Publication number	Publication date
ES486991A1 (es)	1980-10-01
MX5862E (es)	1984-08-13
FR2421174B1 (2)	1982-11-19
SU1140687A3 (ru)	1985-02-15
SE434945B (sv)	1984-08-27
NO791049L (no)	1979-10-02
AT376432B (de)	1984-11-26
SE7902794L (sv)	1979-10-01
AU515531B2 (en)	1981-04-09
FI70704B (fi)	1986-06-26
CH641455A5 (de)	1984-02-29
SU1232144A3 (ru)	1986-05-15
NL7902514A (nl)	1979-10-02
ZA791516B (en)	1980-04-30
FI791034A7 (fi)	1979-10-01
DK158225C (da)	1990-09-17
DK128679A (da)	1979-10-26
US4734416A (en)	1988-03-29
DK158225B (da)	1990-04-16
NL183189C (nl)	1988-08-16
ES486992A1 (es)	1980-10-01
CA1117110A (en)	1982-01-26
JPS6223750B2 (2)	1987-05-25
GB2017701B (en)	1983-03-16
ES479134A1 (es)	1980-06-16
JPS54130587A (en)	1979-10-09
BE875174A (fr)	1979-10-01
FI70704C (fi)	1986-10-06
PT69422A (en)	1979-04-01
GB2017701A (en)	1979-10-10
IT7967674A0 (it)	1979-03-30
ES486990A1 (es)	1980-10-01
ATA235179A (de)	1984-04-15
FR2421174A1 (fr)	1979-10-26
AU4548079A (en)	1979-10-04
CH641350A5 (de)	1984-02-29
IT1119284B (it)	1986-03-10
DE2953723C2 (de)	1989-01-12
NO151321C (no)	1985-03-20
NO151321B (no)	1984-12-10
US4824840A (en)	1989-04-25
DE2912105A1 (de)	1979-10-11

Legal Events

Date	Code	Title	Description
1979-10-11	OAP	Request for examination filed
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