GB1223527A - 3,4-dihydronaphthalenoneoxy-2-hydroxypropylamines - Google Patents

3,4-dihydronaphthalenoneoxy-2-hydroxypropylamines

Info

Publication number
GB1223527A
GB1223527A GB41987/69A GB4198769A GB1223527A GB 1223527 A GB1223527 A GB 1223527A GB 41987/69 A GB41987/69 A GB 41987/69A GB 4198769 A GB4198769 A GB 4198769A GB 1223527 A GB1223527 A GB 1223527A
Authority
GB
United Kingdom
Prior art keywords
tetralone
alkyl
prepared
reaction
aralkyl
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
GB41987/69A
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.)
Warner Lambert Co LLC
Original Assignee
Warner Lambert Pharmaceutical Co
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
Application filed by Warner Lambert Pharmaceutical Co filed Critical Warner Lambert Pharmaceutical Co
Publication of GB1223527A publication Critical patent/GB1223527A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/38—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • C07D303/26—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds having one or more free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Neurology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Epoxy Compounds (AREA)

Abstract

1,223,527. Tetralone derivatives. WARNERLAMBERT PHARMACEUTICAL CO. 22 Aug., 1969 [23 Sept., 1968], No. 41987/69. Heading C2C. Novel compounds I in which R 1 is H or 1-6 C alkyl; R 2 1-6 C alkyl, 2-6 C alkenyl, cycloalkyl or cycloalkylalkyl, each of up to 7 C or aralkyl (optionally substituted); R 3 and R 4 are H, halo, OH, NO 2 , NH 2 , acylamino, sulphonamido, 1-6 C alkyl, or OR 7 (R 7 is 1-6 C alkyl, 2-6 C alkenyl or optionally substituted aralkyl); R 5 and R 6 are H, 1-6 C alkyl, or aralkyl and the propanolamine side chain being in the 5, 6 or 7 position and their salts, O-esters, oximes, semicarbazides, thiosemicarbazides, hydrazones, and oxazolidine and oxazolidinone derivatives are prepared by reaction of compounds II with XCH 2 CHOHCH 2 X or the epoxide of XCH 2 -CH=CH 2 wherein X is halo, followed by reaction with HNR 1 R 2 . Intermediates isolated are 2,2-dimethyl-6- methoxy-1-tetralone (A) prepared from 6-methoxy-1-tetralone and CH 3 I/NaH; 2,2-dimethyl-6- hydroxy - 1 - tetralone prepared from (A) by reaction with HBr/Acetic acid; and the 1-cyclo hexylimino derivative of 5-(3-cyclohexylamino-2- hydroxy - 1 - propyloxy - 1 - tetralone hydrochloride prepared from 5-(2,3-epoxy-1-propyloxy)-1-tetralone and hexylamine. Pharmaceutical compositions comprise a compound I together with a suitable carrier, are administered orally or parenterally and are #-adrenergic blocking agents.
GB41987/69A 1968-09-23 1969-08-22 3,4-dihydronaphthalenoneoxy-2-hydroxypropylamines Expired GB1223527A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US76185768A 1968-09-23 1968-09-23

Publications (1)

Publication Number Publication Date
GB1223527A true GB1223527A (en) 1971-02-24

Family

ID=25063434

Family Applications (1)

Application Number Title Priority Date Filing Date
GB41987/69A Expired GB1223527A (en) 1968-09-23 1969-08-22 3,4-dihydronaphthalenoneoxy-2-hydroxypropylamines

Country Status (15)

Country Link
US (1) US3641152A (en)
JP (1) JPS4843734B1 (en)
BE (1) BE739195A (en)
CH (1) CH525183A (en)
DE (2) DE1967162C3 (en)
DK (2) DK125588B (en)
ES (1) ES371737A1 (en)
FI (1) FI51936C (en)
FR (1) FR2018626B1 (en)
GB (1) GB1223527A (en)
IT (1) IT1033032B (en)
NL (1) NL139166B (en)
NO (1) NO128869B (en)
SE (1) SE362414B (en)
ZA (1) ZA695648B (en)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE755071A (en) * 1969-09-17 1971-02-22 Warner Lambert Pharmaceutical METHOD FOR RESOLVING DL-5- / 3- (TERBUTYLAMINO) -2- HYDROXY-PROPOXY / -3,4-DIHYDRO-1 (2H) NAPHTHALENONE
US3959486A (en) * 1970-05-27 1976-05-25 Imperial Chemical Industries Limited Method for producing β-adrenergic blockage with alkanolamine derivatives
DE2130393C3 (en) * 1970-06-22 1981-02-26 E.R. Squibb & Sons Inc., New York, N.Y. (V.St.A.) 6,7-dihydroxy -5,6,7,8-tetrahydronaphthyloxyaminopropanols and their salts with acids and their use in combating heart disease
FR2119843B1 (en) * 1970-12-28 1974-03-22 Laroche Navarro Labo
JPS5122737Y2 (en) * 1972-12-30 1976-06-11
US3966749A (en) * 1975-02-10 1976-06-29 Interx Research Corporation Novel synthesis of optically active m-acyloxy-α-[(methylamino)methyl]benzyl alcohols, the pharmaceutically acceptable acid addition salts thereof and intermediate useful in the preparation thereof
GB1493848A (en) * 1975-07-24 1977-11-30 Beecham Group Ltd Aryltetralins
CH621330A5 (en) * 1976-05-14 1981-01-30 Sandoz Ag
DE2810869A1 (en) * 1977-03-24 1978-09-28 Sandoz Ag 3-AMINO-2-HYDROXYPROPOXY DERIVATIVES, THEIR PRODUCTION AND USE
US4176183A (en) * 1977-05-02 1979-11-27 Merck & Co., Inc. Novel naphthyridines
US4270005A (en) * 1977-11-14 1981-05-26 Pfizer Inc. 1,9-Dihydroxyoctahydrophenanthrenes and intermediates therefor
CH641147A5 (en) * 1979-01-17 1984-02-15 Sandoz Ag 3-AMINO-2-HYDROXYPROPOXYARYL DERIVATIVE, ITS PREPARATION AND REMEDIES CONTAINING THEREOF.
DE2943406A1 (en) * 1979-10-26 1981-05-07 Basf Ag, 6700 Ludwigshafen AMINO DERIVATIVES OF 2-METHYL-5- (2-HYDROXYSTYRYL) -1,3,4-THIADIAZOL
FR2507181A1 (en) * 1981-06-05 1982-12-10 Sanofi Sa NOVEL ETHERS OF PHENOL ACTIVE ON THE CARDIOVASCULAR SYSTEM, PROCESS FOR PREPARING THEM AND USE THEREOF IN MEDICAMENTS
SE8801518D0 (en) * 1988-04-22 1988-04-22 Astra Pharma Prod A NOVEL PROCESS
US5225565A (en) * 1988-09-15 1993-07-06 The Upjohn Company Antibacterial 3-(fused-ring substituted)phenyl-5β-amidomethyloxazolidin-2-ones
ES2065278B1 (en) * 1993-06-24 1995-09-01 Medichem Sa LEVOBUNOLOL ENANTIOSELECTIVE PROCEDURE FOR OBTAINING.
ATE330633T1 (en) * 2000-07-27 2006-07-15 Pharmacia Corp EPOXY-STEROIDAL ALDOSTERONE ANTAGONIST AND BETA-ADRENERGIC ANTAGONIST COMBINATION THERAPY FOR THE TREATMENT OF CONGESTIVE HEART FAILURE

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1023214A (en) * 1962-12-17 1966-03-23 Ici Ltd Carbocyclic hydroxyamines

Also Published As

Publication number Publication date
DE1948144B2 (en) 1979-05-03
FI51936B (en) 1977-01-31
FI51936C (en) 1977-05-10
ES371737A1 (en) 1972-03-16
US3641152A (en) 1972-02-08
ZA695648B (en) 1971-03-31
DK125588B (en) 1973-03-12
NL6914077A (en) 1970-03-25
BE739195A (en) 1970-03-23
IT1033032B (en) 1979-07-10
NO128869B (en) 1974-01-21
CH525183A (en) 1972-07-15
FR2018626B1 (en) 1973-06-08
DE1967162C3 (en) 1981-03-19
SE362414B (en) 1973-12-10
NL139166B (en) 1973-06-15
FR2018626A1 (en) 1970-06-26
DE1948144A1 (en) 1970-03-26
JPS4843734B1 (en) 1973-12-20
DE1967162B1 (en) 1980-07-31
DE1948144C3 (en) 1980-01-17
DK128536B (en) 1974-05-20

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