ES251458A1 - -amino- -hydroxy carboxylic acid amides and process for preparing them - Google Patents
-amino- -hydroxy carboxylic acid amides and process for preparing themInfo
- Publication number
- ES251458A1 ES251458A1 ES0251458A ES251458A ES251458A1 ES 251458 A1 ES251458 A1 ES 251458A1 ES 0251458 A ES0251458 A ES 0251458A ES 251458 A ES251458 A ES 251458A ES 251458 A1 ES251458 A1 ES 251458A1
- Authority
- ES
- Spain
- 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
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (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.
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 |
---|---|
ES251458A1 true ES251458A1 (en) | 1960-05-16 |
Family
ID=7092016
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES0251458A Expired ES251458A1 (en) | 1958-08-16 | 1959-08-14 | -amino- -hydroxy carboxylic acid amides and process for preparing them |
Country Status (4)
Country | Link |
---|---|
CH (2) | CH410977A (en) |
DE (1) | DE1087616B (en) |
ES (1) | ES251458A1 (en) |
GB (1) | GB926861A (en) |
-
1958
- 1958-08-16 DE DEF26416A patent/DE1087616B/en active Pending
-
1959
- 1959-08-14 ES ES0251458A patent/ES251458A1/en not_active Expired
- 1959-08-14 CH CH7697659A patent/CH410977A/en unknown
- 1959-08-14 CH CH241166A patent/CH413855A/en unknown
- 1959-08-17 GB GB2810559A patent/GB926861A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH413855A (en) | 1966-05-31 |
DE1087616B (en) | 1960-08-25 |
GB926861A (en) | 1963-05-22 |
CH410977A (en) | 1966-04-15 |
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