GB969977A - Substituted 1,3-diphenyl-propyl amines and imines - Google Patents

Substituted 1,3-diphenyl-propyl amines and imines

Info

Publication number
GB969977A
GB969977A GB23490/62A GB2349062A GB969977A GB 969977 A GB969977 A GB 969977A GB 23490/62 A GB23490/62 A GB 23490/62A GB 2349062 A GB2349062 A GB 2349062A GB 969977 A GB969977 A GB 969977A
Authority
GB
United Kingdom
Prior art keywords
product
compounds
ketone
alkyl
alkyl amine
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
GB23490/62A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB969977A publication Critical patent/GB969977A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • 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
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises (1) the preparation of compounds of general formula <FORM:0969977/C1/1> wherein S1 denotes substitution with from one to three methoxy groups and S2 denotes substitution with from one to three substituents drawn from fluoro, chloro, bromo and nitro, and acid addition salts thereof, which comprises condensing a ketone of formula: <FORM:0969977/C1/2> (the broken line denotes the attached substituents are optional) with ammonia or an alkyl amine or a dialkyl amine under hydrogenation conditions and, when ammonia or an alkyl amine is used, alkylating the condensation product, nitrating the dialkyl amine product where it is desired to have a nitro substituent in the ultimate product but this is not contained in the starting ketone and, if desired, converting the product into an acid addition salt; (2) the preparation which comprises condensing said ketone with an alkyl amine under non-hydrogenation conditions and reducing the Schiff's base at the carbon-nitrogen double bond before or after alkylation; (3) the additional step of separating intermediate amines or alkylamines or final dialkylamines into their optical antipodes; and (4) the compounds of general formulae <FORM:0969977/C1/3> <FORM:0969977/C1/4> <FORM:0969977/C1/5> Ketones of the general Formula II above may be prepared by Friedel-Crafts reaction of an alkyl-benzene with an o -phenyl-propionyl halide or with an acetyl halide followed by condensation with a benzaldehyde and subsequent reduction. Pharmaceutical preparations containing amines I above for enteral or parenteral administration (tablets, dragees, capsules, suppositories, solutions, suspensions, emulsions) are mentioned. The compounds are analgesics, spasmolytics, antitussives and blood-pressure lowering agents. Specification 969,077 is referred to.
GB23490/62A 1961-06-20 1962-06-19 Substituted 1,3-diphenyl-propyl amines and imines Expired GB969977A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH720261A CH410974A (en) 1961-06-20 1961-06-20 Process for the preparation of substituted benzylamines

Publications (1)

Publication Number Publication Date
GB969977A true GB969977A (en) 1964-09-16

Family

ID=4321459

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23490/62A Expired GB969977A (en) 1961-06-20 1962-06-19 Substituted 1,3-diphenyl-propyl amines and imines

Country Status (4)

Country Link
BE (1) BE619196A (en)
CH (1) CH410974A (en)
ES (1) ES278485A1 (en)
GB (1) GB969977A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4855502A (en) * 1978-10-05 1989-08-08 Hoechst-Roussel Pharmaceuticals, Inc. α-(2-nitro-phenylmethyl)-benzylamines
US4933493A (en) * 1978-10-05 1990-06-12 Hoechst-Roussel Pharmaceuticals Inc. Intermediates for the preparation of 4-phenyl-1,3-benzodiazepines
US6462236B2 (en) 2000-10-27 2002-10-08 Basf Aktiengesellschaft Preparation of amines
US7323599B2 (en) 2005-10-01 2008-01-29 Clariant Speciality Fine Chemicals (Deutschland) Gmbh Process for reductively aminating ketones and aldehydes with aqueous amines and catalysts suitable therefor

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4855502A (en) * 1978-10-05 1989-08-08 Hoechst-Roussel Pharmaceuticals, Inc. α-(2-nitro-phenylmethyl)-benzylamines
US4933493A (en) * 1978-10-05 1990-06-12 Hoechst-Roussel Pharmaceuticals Inc. Intermediates for the preparation of 4-phenyl-1,3-benzodiazepines
US6462236B2 (en) 2000-10-27 2002-10-08 Basf Aktiengesellschaft Preparation of amines
US7323599B2 (en) 2005-10-01 2008-01-29 Clariant Speciality Fine Chemicals (Deutschland) Gmbh Process for reductively aminating ketones and aldehydes with aqueous amines and catalysts suitable therefor

Also Published As

Publication number Publication date
BE619196A (en) 1962-12-20
ES278485A1 (en) 1962-12-01
CH410974A (en) 1966-04-15

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