GB926861A - ª -amino-ª -hydroxy carboxylic acid amides and process for preparing them - Google Patents

ª -amino-ª -hydroxy carboxylic acid amides and process for preparing them

Info

Publication number
GB926861A
GB926861A GB2810559A GB2810559A GB926861A GB 926861 A GB926861 A GB 926861A GB 2810559 A GB2810559 A GB 2810559A GB 2810559 A GB2810559 A GB 2810559A GB 926861 A GB926861 A GB 926861A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
product
reduction
conhr
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
GB2810559A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst 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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB926861A publication Critical patent/GB926861A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention comprises alpha-amino-beta-hydroxy-butyric acid amides substituted on the amido nitrogen atom by an aliphatic hydrocarbon radical R which is attached to the nitrogen atom by a tertiary carbon atom, and acid-addition salts thereof; and the preparation thereof by treating a compound of the formula CH3COCH2CONHR (prepared from diketene and the amines NH2R) with nitrous acid or reacting it with an aryl diazonium salt, and reducing the product. The products of the reaction with nitrous acid are a -isonitroso derivatives of the keto-amides of the above formula, and they may be reduced in stages, first by reduction with for example, nascent-hydrogen to a compound of the formula CH3COCH(NH2)CONHR and then to the required product with, for example, sodium or aluminium amalgam and an alcohol and sodium borohydride or by catalytic hydrogenation or electrolytically. Before this final reduction, the intermediate amine is desirably acylated to give a compound of the formula CH3COCH(NHAc) CONHR (wherein Ac is an acylating group such as an acetyl, propionyl, benzoyl or phenylacetyl group) which on reduction gives a compound of the formula CH3CH(OH) CH(NHAc)CONHR from which the required final product is obtained by hydrolysis. The products of the reaction with an aryl diazonium salt are a -arylazo derivatives of the keto-amide starting materials, which may then be reduced in stages by the same methods as are employed for the isonitroso compounds. Alternatively the reduction process of the invention may be effected in one stage, by catalytic hydrogenation, or electrolytically, or with nascent hydrogen or sodium borohydride. Detailed examples are given, one product being isolated in two isomeric forms. The amides of the invention, which have analgesic properties, may be incorporated in pharmaceutical compositions with the aid of suitable carriers. Specifications 816,225 and 828,694 are referred to.
GB2810559A 1958-08-16 1959-08-17 ª -amino-ª -hydroxy carboxylic acid amides and process for preparing them Expired GB926861A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF26416A DE1087616B (en) 1958-08-16 1958-08-16 Process for the preparation of ª ‡ -amino-ª ‰ -oxy-carboxylic acid amides with an analgesic effect

Publications (1)

Publication Number Publication Date
GB926861A true GB926861A (en) 1963-05-22

Family

ID=7092016

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2810559A Expired GB926861A (en) 1958-08-16 1959-08-17 ª -amino-ª -hydroxy carboxylic acid amides and process for preparing them

Country Status (4)

Country Link
CH (2) CH413855A (en)
DE (1) DE1087616B (en)
ES (1) ES251458A1 (en)
GB (1) GB926861A (en)

Also Published As

Publication number Publication date
CH413855A (en) 1966-05-31
DE1087616B (en) 1960-08-25
CH410977A (en) 1966-04-15
ES251458A1 (en) 1960-05-16

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