GB858426A - Production of amido-alkylamides - Google Patents
Production of amido-alkylamidesInfo
- Publication number
- GB858426A GB858426A GB31414/57A GB3141457A GB858426A GB 858426 A GB858426 A GB 858426A GB 31414/57 A GB31414/57 A GB 31414/57A GB 3141457 A GB3141457 A GB 3141457A GB 858426 A GB858426 A GB 858426A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- glycine
- chloride
- give
- reacted
- 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
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen 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: R1-CO-NH-(CH2)n-Co-NR3R4 wherein R1 is a mono-or poly-lower alkoxy ring-substituted phenyl or styryl group, or a halophenyl group, n is 1 or 2, and R3 and R4 are lower alkyl groups, the lower alkyl and lower alkoxy groups each containing at most 4 carbon atoms ; and their preparation by the following processes (a) reacting an amido-ester of the formula R1-CO-NH-(CH2)n-COOR2, wherein R2 is an alkyl group, with hydrazine and then with nitrous acid to produce the corresponding azide and treating the latter with an amine NHR3R4, or treating the ester directly with this amine, the amido-ester starting material being prepared by reacting the amino-acid ester NH2-(CH2)n-COOR2 either with the acid halide R1-CO-Hal or with the acid R1-COOH in the presence of an N:N1-disubstituted carbodiimide; (b) treating a haloamide of the formula Hal-(CH2)-CONR3R4 (prepared from Hal-(CH2)n-COHal and the amine NHR3R4) with the amide R1-CO-NH2 in presence of an alkali metal hydride ; or (c) reacting the amino-amide NH2 (CH2)-CO-NR3R4 with the aroyl halide R1-CO-Hal. In examples (1) glycine ethyl ester and 3 : 4 : 5-trimethoxybenzoic acid give the 3 : 4 : 5-trimethoxybenzoic acid amide of glycine ethyl ester, this with hydrazine hydrate gives the hydrazide, and this is treated with nitrous acid and then with diethylamine as in (a) above ; (2) 3 : 4 : 5-trimethoxybenzoic acid and thionyl chloride give 3 : 4 : 5-trimethoxylbenzoyl chloride and this is treated with N : N-diethyl-b -alanine amide as in (c) above ; (3) p-chlorobenzoyl chloride and glycine ethyl ester hydrochloride give p-chlorobenzoylglycine ethyl ester and this is treated with diethylamine as in the alternative procedure of (a) above ; (4) 3 : 4 : 5-trimethoxycinnamic acid and thionyl chloride give 3 : 4 : 5-trimethoxycinramoyl chloride and this is reacted with glycine diethylamide as in (c) ; (5) anisic acid and thionyl chloride give p-anisoyl chloride and this is reacted with glycine diethylamide as in (c) ; (6) veratroyl chloride is prepared similarly and reacted with glycine diethylamide ; (7) 3 : 4 : 5-trimethoxy-benzamide and diethylchloroacetamide are reacted as in (b) above ; (8) the veratric acid amide of glycine hydrazide is prepared as in (1) and is then converted via the azide to the di-n-butylamide ; (9) dimethylamine replaces the diethylamine in the last stage of (1) ; (10) phthaloyl glycine acid chloride is heated with di-isopropylamine in pyridine to give phthaloyl glycine di-isopropylamide, this is heated with hydrazine hydrate in methanol to give glycine di-isopropylamide and this is reacted with 3 : 4 : 5-trimethoxybenzoyl chloride as in (c) ; and (11) 3 : 4 : 5-trimethoxy-benzoic acid is reacted with glycine diethylamide in presence of N : N1-dicyclohexylcarbodiimide to give the same product as in (1).ALSO:Pharmaceutical compositions comprise a compound of the formula R1-CO-NH-(CH2)nCO-NR3R4 wherein R1 is a mono-or polylower alkoxy ring substituted phenyl or styryl group, or a halophenyl group, n is 1 or 2, and R3 and R4 are lower alkyl groups, the lower alkyl and lower alkoxy groups each containing at most 4 carbon atoms, in admixture with suitable diluents. The compositions may take the form of solutions, tablets or capsules. An example describes a tablet containing 3:4:5 trimethoxy benzoylglycine diethylamide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US858426XA | 1956-10-15 | 1956-10-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB858426A true GB858426A (en) | 1961-01-11 |
Family
ID=22194310
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB31414/57A Expired GB858426A (en) | 1956-10-15 | 1957-10-08 | Production of amido-alkylamides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB858426A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0576941A1 (en) * | 1992-06-30 | 1994-01-05 | Nisshin Flour Milling Co., Ltd. | N-benzoylamino acid derivatives, pharmaceutical compositions containing them and process for preparing same |
-
1957
- 1957-10-08 GB GB31414/57A patent/GB858426A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0576941A1 (en) * | 1992-06-30 | 1994-01-05 | Nisshin Flour Milling Co., Ltd. | N-benzoylamino acid derivatives, pharmaceutical compositions containing them and process for preparing same |
US5705529A (en) * | 1992-06-30 | 1998-01-06 | Gyogyszerkutato Intezet Kft | N-benzoyl amino acid derivatives pharmaceutical compositions containing them and process for preparing same |
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