GB877306A - Halogenated derivatives of tetrahydro-1-naphthyl cyclic amidines - Google Patents

Halogenated derivatives of tetrahydro-1-naphthyl cyclic amidines

Info

Publication number
GB877306A
GB877306A GB12594/59A GB1259459A GB877306A GB 877306 A GB877306 A GB 877306A GB 12594/59 A GB12594/59 A GB 12594/59A GB 1259459 A GB1259459 A GB 1259459A GB 877306 A GB877306 A GB 877306A
Authority
GB
United Kingdom
Prior art keywords
halogenated
tetrahydro
produce
acid
phenyl
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
GB12594/59A
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.)
Pfizer Inc
Original Assignee
Pfizer Inc
Charles Pfizer and Co Inc
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 Pfizer Inc, Charles Pfizer and Co Inc filed Critical Pfizer Inc
Publication of GB877306A publication Critical patent/GB877306A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0877306/IV (b)/1> wherein X represents at least one halogen atom, R is a hydrogen atom or a C1-C5 alkyl or C2-C5 alkenyl radical, and n is 2 or 3, and acid addition salts thereof, and the preparation thereof by alcoholysing a halogenatedphenylacetonitrile to an alkyl halogenated-phenylacetate and adding an alkyl acrylate to produce a dialkyl alpha-(halogenated-phenyl)-glutarate and hydrolysing the glutarate to produce an alpha-(halogenated-phenyl)-glutaric acid and dehydrating the acid to produce an alpha-(halogenated-phenyl)-glutaric anhydride and cyclizing this to a halogenated-4-keto 1,2,3,4-tetrahydro-1-naphthoic acid and reducing this to a halogenated-1,2,3,4-tetrahydro-1-naphthoic acid and amidating this to a halogenated - 1,2,3,4 - tetrahydro - 1 - naphthoamide and dehydrating the amide to produce a halogenated 1,2,3,4-tetrahydro-1-naphthonitrile and condensing the nitrile with an unsubstituted or mono-N-substituted ethylene diamine or 1,3-diaminopropane; and, if desired, converting the products into their acid addition salts. The products have depressor, blood pressure lowering, adrenergic blocking or cardiac rate decreasing properties depending upon their molecular structures. o-Chlorophenyl-acetonitrile and o-bromophenyl-acetonitrile are prepared by treating the corresponding o-halogenobenzyl halides with potassium cyanide.
GB12594/59A 1958-04-21 1959-04-14 Halogenated derivatives of tetrahydro-1-naphthyl cyclic amidines Expired GB877306A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US877306XA 1958-04-21 1958-04-21

Publications (1)

Publication Number Publication Date
GB877306A true GB877306A (en) 1961-09-13

Family

ID=22206915

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12594/59A Expired GB877306A (en) 1958-04-21 1959-04-14 Halogenated derivatives of tetrahydro-1-naphthyl cyclic amidines

Country Status (1)

Country Link
GB (1) GB877306A (en)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2312244A1 (en) * 1975-05-30 1976-12-24 Scherico Ltd Hypoglycaemic 2-imidazolines - e.g. (2-(6-fluoro 1,2,3,4-tetrahydro 1-naphthyl methyl) imidazoline
US4002626A (en) * 1976-03-15 1977-01-11 Morton-Norwich Products, Inc. 1-(2-Naphthylmethyl)-3,4,5,6-tetrahydro-2(1H)pyrimidone
US4634705A (en) * 1984-06-06 1987-01-06 Abbott Laboratories Adrenergic amidines
WO2007085558A1 (en) * 2006-01-27 2007-08-02 F. Hoffmann-La Roche Ag Use of 2-imidazoles for the treatment of cns disorders
US7652055B2 (en) 2007-07-02 2010-01-26 Hoffman-La Roche Inc. 2-imidazolines
US7812047B2 (en) 2007-07-03 2010-10-12 Hoffman-La Roche Inc. 4-imidazolines
US7834044B2 (en) 2006-11-02 2010-11-16 Hoffman-Laroche Inc. Substituted-2-imidazoles
US7858652B2 (en) 2006-11-16 2010-12-28 Hoffmann-La Roche Inc. Substituted 4-imidazoles
US7858653B2 (en) 2006-12-13 2010-12-28 Hoffman-La Roche Inc. 2-imidazoles
US7902238B2 (en) 2007-02-15 2011-03-08 Hoffmann-La Roche Inc. 2-aminooxazolines as TAAR1 ligands
US8008305B2 (en) 2007-08-03 2011-08-30 Hoffmann-La Roche Inc. TAAR1 ligands
US8242153B2 (en) 2008-07-24 2012-08-14 Hoffmann-La Roche Inc. 4,5-dihydro-oxazol-2YL derivatives
US8354441B2 (en) 2009-11-11 2013-01-15 Hoffmann-La Roche Inc. Oxazoline derivatives
US8389507B2 (en) 2007-07-27 2013-03-05 Hoffmann-La Roche Inc. 2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as TAAR-ligands
US8399463B2 (en) 2006-12-18 2013-03-19 Hoffmann-La Roche Inc. Imidazole derivatives
US8586617B2 (en) 2006-10-19 2013-11-19 Hoffmann-La Roche Inc. Aminomethyl-4-imidazoles
US8604061B2 (en) 2007-02-02 2013-12-10 Hoffmann-La Roche Inc. 2-aminooxazolines as TAAR1 ligands
US9452980B2 (en) 2009-12-22 2016-09-27 Hoffmann-La Roche Inc. Substituted benzamides
US10508107B2 (en) 2016-03-17 2019-12-17 Hoffmann-La Roche Inc. Morpholine derivative

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2312244A1 (en) * 1975-05-30 1976-12-24 Scherico Ltd Hypoglycaemic 2-imidazolines - e.g. (2-(6-fluoro 1,2,3,4-tetrahydro 1-naphthyl methyl) imidazoline
US4002626A (en) * 1976-03-15 1977-01-11 Morton-Norwich Products, Inc. 1-(2-Naphthylmethyl)-3,4,5,6-tetrahydro-2(1H)pyrimidone
US4634705A (en) * 1984-06-06 1987-01-06 Abbott Laboratories Adrenergic amidines
WO2007085558A1 (en) * 2006-01-27 2007-08-02 F. Hoffmann-La Roche Ag Use of 2-imidazoles for the treatment of cns disorders
US8586617B2 (en) 2006-10-19 2013-11-19 Hoffmann-La Roche Inc. Aminomethyl-4-imidazoles
US7834044B2 (en) 2006-11-02 2010-11-16 Hoffman-Laroche Inc. Substituted-2-imidazoles
US7858652B2 (en) 2006-11-16 2010-12-28 Hoffmann-La Roche Inc. Substituted 4-imidazoles
US7858653B2 (en) 2006-12-13 2010-12-28 Hoffman-La Roche Inc. 2-imidazoles
US8399463B2 (en) 2006-12-18 2013-03-19 Hoffmann-La Roche Inc. Imidazole derivatives
US8604061B2 (en) 2007-02-02 2013-12-10 Hoffmann-La Roche Inc. 2-aminooxazolines as TAAR1 ligands
US7902238B2 (en) 2007-02-15 2011-03-08 Hoffmann-La Roche Inc. 2-aminooxazolines as TAAR1 ligands
US7652055B2 (en) 2007-07-02 2010-01-26 Hoffman-La Roche Inc. 2-imidazolines
US7812047B2 (en) 2007-07-03 2010-10-12 Hoffman-La Roche Inc. 4-imidazolines
US8389507B2 (en) 2007-07-27 2013-03-05 Hoffmann-La Roche Inc. 2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as TAAR-ligands
US8008305B2 (en) 2007-08-03 2011-08-30 Hoffmann-La Roche Inc. TAAR1 ligands
US8242153B2 (en) 2008-07-24 2012-08-14 Hoffmann-La Roche Inc. 4,5-dihydro-oxazol-2YL derivatives
US8729113B2 (en) 2008-07-24 2014-05-20 Hoffmann-La Roche Inc. 4,5-dihydro-oxazol-2yl derivatives
US8354441B2 (en) 2009-11-11 2013-01-15 Hoffmann-La Roche Inc. Oxazoline derivatives
US9452980B2 (en) 2009-12-22 2016-09-27 Hoffmann-La Roche Inc. Substituted benzamides
US10508107B2 (en) 2016-03-17 2019-12-17 Hoffmann-La Roche Inc. Morpholine derivative
US11312711B2 (en) 2016-03-17 2022-04-26 Hoffmann-La Roche Inc. Morpholine derivative

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