GB1424572A - 3,4-dihydrocarbostyril derivatives and their preparation - Google Patents

3,4-dihydrocarbostyril derivatives and their preparation

Info

Publication number
GB1424572A
GB1424572A GB3417075A GB3417075A GB1424572A GB 1424572 A GB1424572 A GB 1424572A GB 3417075 A GB3417075 A GB 3417075A GB 3417075 A GB3417075 A GB 3417075A GB 1424572 A GB1424572 A GB 1424572A
Authority
GB
United Kingdom
Prior art keywords
formula
reacting
prepared
dihydrocarbostyril
compound
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
Application number
GB3417075A
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.)
Filing date
Publication date
Priority claimed from JP9255772A external-priority patent/JPS5324431B2/ja
Priority claimed from JP47092560A external-priority patent/JPS5246231B2/ja
Priority claimed from JP47092558A external-priority patent/JPS5241268B2/ja
Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd
Publication of GB1424572A publication Critical patent/GB1424572A/en
Expired legal-status Critical Current

Links

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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Quinoline Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1424572 3,4-Dihydrocarbostyril derivatives OTSUKA PHARMACEUTICAL CO Ltd 22 Jan 1973 [13 April 1972 (2) 14 Sept 1972 (3) 2 Dec 1972 21 Dec 1972] 34170/75 Divided out of 1424571 Heading C2C The invention comprises 3,4-dihydrocarbostyril derivatives of Formula (I) in which R<SP>1</SP> is hydrogen, a C 1 -C 4 alkyl group, an aralkyl group or a C 2 -C 4 alkenyl group and Z represents (a) or (b) -CHOH-CH 2 X where X is a halogen atom. They may be prepared by reacting a 5-, 6-, 7- or 8-hydroxy-3,4-dihydrocarbostyril derivative of Formula II with an epihalohydrin of Formula III in the presence of a basic compound. The compounds of Formula II may be prepared by reacting a 3,4,5,6,7,8-hexahydrocarbostyril-5- one of Formula VI with a brominating agent to get an 8- (or 6-) -bromo derivative and heating this to remove bromine and dehydrogenate the ring. The proportion of the two products having groups (a) and (b) obtained depends on the reaction conditions. The compounds in which Z is the group (b) may also be prepared by reacting a compound of Formula (VI) above with a compound of formula CH 2 OH.CHOH.CH 2 X (X is a halogen) in the presence of a brominating agent.
GB3417075A 1972-04-13 1973-01-22 3,4-dihydrocarbostyril derivatives and their preparation Expired GB1424572A (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP47037182A JPS48103590A (en) 1972-04-13 1972-04-13
JP47037181A JPS517672B2 (en) 1972-04-13 1972-04-13
JP9255772A JPS5324431B2 (en) 1972-09-14 1972-09-14
JP47092560A JPS5246231B2 (en) 1972-09-14 1972-09-14
JP47092558A JPS5241268B2 (en) 1972-09-14 1972-09-14
JP47120953A JPS5229745B2 (en) 1972-04-13 1972-12-02
JP47125858A JPS5239036B2 (en) 1972-04-13 1972-12-14
JP47128972A JPS5241269B2 (en) 1972-04-13 1972-12-21

Publications (1)

Publication Number Publication Date
GB1424572A true GB1424572A (en) 1976-02-11

Family

ID=27572212

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3417075A Expired GB1424572A (en) 1972-04-13 1973-01-22 3,4-dihydrocarbostyril derivatives and their preparation
GB325173A Expired GB1424571A (en) 1972-04-13 1973-01-22 3,4-dihydrocarbostyril derivatives their preparation and pharmaceutical compositions thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB325173A Expired GB1424571A (en) 1972-04-13 1973-01-22 3,4-dihydrocarbostyril derivatives their preparation and pharmaceutical compositions thereof

Country Status (17)

Country Link
JP (5) JPS517672B2 (en)
AR (1) AR209575A1 (en)
AU (1) AU475964B2 (en)
BE (1) BE794669A (en)
CA (1) CA1025447A (en)
CH (1) CH575929A5 (en)
DD (2) DD112446A5 (en)
DE (1) DE2302027C2 (en)
DK (1) DK141603B (en)
FI (1) FI53703C (en)
FR (1) FR2179715B1 (en)
GB (2) GB1424572A (en)
HK (1) HK19481A (en)
NL (1) NL158176B (en)
NO (1) NO140589C (en)
SE (1) SE380018B (en)
YU (1) YU41187B (en)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5082218A (en) * 1973-11-10 1975-07-03
US4022784A (en) * 1974-01-31 1977-05-10 Otsuka Pharmaceutical Company Limited 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-substituted-carbostyril and -3,4-dihydrocarbostyril derivatives
US4137331A (en) 1974-06-19 1979-01-30 Sandoz Ltd. 3-Piperidino-2-hydroxypropoxy substituted-2-indolinones
JPS516971A (en) * 1974-07-08 1976-01-20 Otsuka Pharma Co Ltd Nitoro 3*44 jihidorokarubosuchirirujudotaino seizoho
JPS5129486A (en) * 1974-09-02 1976-03-12 Otsuka Pharma Co Ltd * 33 arukiruamino 22 hidorokishi * purohokishi 3 44 jihidorokarubosuchirirujudotai no seizoho
JPS5148674A (en) * 1974-10-17 1976-04-26 Otsuka Pharma Co Ltd 3 44 jihidorokarubosuchirirujudotaino seizoho
JPS5152178A (en) * 1974-10-31 1976-05-08 Otsuka Pharma Co Ltd KARUBOSUCHIRIRU JUDOTAINO SEIZOHO
JPS5152179A (en) * 1974-10-31 1976-05-08 Otsuka Pharma Co Ltd KARUBOSUCHIRIRU JUDOTAINO SEIZOHO
JPS5152180A (en) * 1974-10-31 1976-05-08 Otsuka Pharma Co Ltd KARUBOSUCHIRIRU JUDOTAINO SEIZOHO
FI58329C (en) * 1974-11-08 1981-01-12 Otsuka Pharma Co Ltd PROCEDURE FOR FRAMSTATION OF I 8-STATIONARY SUBSTITUTES 5- (3'-ALKYLAMINO-2'-HYDROXY) PROPOXI-3,4-DIHYDROCARBOSTYRILDER
US4081447A (en) * 1975-04-09 1978-03-28 Abbott Laboratories 5-[2-Hydroxy-3-(3,4-dimethoxy phenethylamino)]-propoxy-3,4-dihydro carbostyril and pharmaceutically acceptable salts thereof
CH619453A5 (en) * 1976-03-17 1980-09-30 Otsuka Pharma Co Ltd
GB1574665A (en) * 1976-05-08 1980-09-10 Otsuka Pharma Co Ltd 3,4-dihydrocarbostyril derivatives and process for preparing the same
US4146630A (en) * 1976-11-12 1979-03-27 Boehringer Mannheim Gmbh Blood pressure lowering and adrenergic β-receptor inhibiting 3-(4-phenoxymethylpiperidino)-propyl-phenyl ethers
JPS54130587A (en) * 1978-03-30 1979-10-09 Otsuka Pharmaceut Co Ltd Carbostyryl derivative
DE2960178D1 (en) * 1978-06-06 1981-04-09 Hoechst Ag New substituted phenylpiperazine derivatives, pharmaceutical compositions containing them and process for their preparation
DE2827566A1 (en) * 1978-06-23 1980-01-10 Boehringer Mannheim Gmbh 1,2-DIHYDRO-CHINOLIN-2-ON DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF
AU518814B2 (en) * 1979-01-30 1981-10-22 Otsuka Pharamaceutical Co. Glaucoma treatment
DE3034237A1 (en) * 1979-09-18 1981-04-16 Otsuka Pharmaceutical Co. Ltd., Tokyo CARBOSTYRIL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND ANTIHISTAMINICALLY ACTIVE AGENTS CONTAINING THESE COMPOUNDS
JPS56122356A (en) * 1980-02-29 1981-09-25 Otsuka Pharmaceut Co Ltd Carbostyril derivative
JPS58103343A (en) * 1981-12-15 1983-06-20 Ota Seiyaku Kk Preparation of propanolamine compound
JPS597186A (en) * 1982-07-02 1984-01-14 Ota Seiyaku Kk 1,3,2-dioxathiolane 2-oxide derivative
JPS63193086U (en) * 1987-05-30 1988-12-13
DE3808136A1 (en) * 1988-03-11 1989-09-21 Thomae Gmbh Dr K DRUGS CONTAINING CHINOLINE-2,5-DIONE, NEW CHINOLINE-2,5-DIONE AND METHOD OF PREPARING THEM
US5266577A (en) * 1988-08-10 1993-11-30 Otsuka Pharmaceutical Company Ltd. Method of treating congestive heart failure using carbostyril derivatives
DE68920797T2 (en) * 1988-08-10 1995-06-29 Otsuka Pharma Co Ltd Heart medication.
CA2093633A1 (en) * 1991-08-23 1993-02-24 Seiji Sato Carbostyril derivative and platelets aggregation inhibitory agent
ES2048108B1 (en) * 1992-07-17 1994-10-01 Lusochimica Spa PROCEDURE FOR THE PREPARATION OF 5- (3-TERC-BUTILAMINO-2-HIDROXIPROPOXI) -3,4-DIHIDROCARBOESTIRILO.
IT1264816B1 (en) * 1993-07-28 1996-10-10 Pergam Srl Process for the preparation of 3,4-dihydrocarbostyryl derivatives
CZ300351B6 (en) * 2005-05-26 2009-04-29 Zentiva, A. S. Process for preparing 7-hydroxy-3,4-dihydrocarbostyril

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1058822A (en) * 1963-07-30 1967-02-15 Ici Ltd 3-amino-2-hydroxypropoxy heterocyclic derivatives
CH523899A (en) * 1968-07-05 1972-06-15 Cassella Farbwerke Mainkur Ag 2-oxo-1,2-dihydroquinoline derivs

Also Published As

Publication number Publication date
YU41187B (en) 1986-12-31
FI53703C (en) 1978-07-10
DK141603B (en) 1980-05-05
NL7302353A (en) 1973-10-16
JPS5239036B2 (en) 1977-10-03
DD108293A5 (en) 1974-09-12
JPS48103590A (en) 1973-12-25
JPS4976878A (en) 1974-07-24
AU475964B2 (en) 1976-09-09
AU5438673A (en) 1974-10-17
FI53703B (en) 1978-03-31
JPS4982673A (en) 1974-08-08
JPS517672B2 (en) 1976-03-10
FR2179715A1 (en) 1973-11-23
DE2302027A1 (en) 1973-12-06
FR2179715B1 (en) 1976-12-03
DD112446A5 (en) 1975-04-12
JPS5229745B2 (en) 1977-08-03
JPS48103589A (en) 1973-12-25
CA1025447A (en) 1978-01-31
NO140589B (en) 1979-06-25
SE380018B (en) 1975-10-27
DK141603C (en) 1980-10-06
JPS4981373A (en) 1974-08-06
JPS5241269B2 (en) 1977-10-17
BE794669A (en) 1973-05-16
DE2302027C2 (en) 1983-03-17
CH575929A5 (en) 1976-05-31
GB1424571A (en) 1976-02-11
HK19481A (en) 1981-05-22
YU254979A (en) 1982-10-31
NO140589C (en) 1979-10-03
NL158176B (en) 1978-10-16
AR209575A1 (en) 1977-05-13

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Legal Events

Date Code Title Description
PS Patent sealed
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
PE20 Patent expired after termination of 20 years

Effective date: 19930120