GB761799A - Benzilamide derivatives - Google Patents
Benzilamide derivativesInfo
- Publication number
- GB761799A GB761799A GB9294/54A GB929454A GB761799A GB 761799 A GB761799 A GB 761799A GB 9294/54 A GB9294/54 A GB 9294/54A GB 929454 A GB929454 A GB 929454A GB 761799 A GB761799 A GB 761799A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- methylbenzilamido
- methyl
- bromide
- chloride
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds having the general formula <FORM:0761799/IV(b)/1> wherein Y is lower alkylene of at least 2 carbon atoms, R and R1 are each lower alkyl or, together with N, form a heterocyclic ring, R11 is hydrogen, lower alkyl or aralkyl, and X is an anion. (The terms "lower alkyl" and "lower alkylene" are meant to denote branched as well as straight chain groups having two to six carbon atoms.) Such compounds, when they are hydrohalides, may be obtained by heating a diamine of the formula <FORM:0761799/IV(b)/2> with an a -halodiphenyl acetyl halide and then heating in the presence of dilute mineral acid or alkali. The free base can then be liberated and reacted with other acids to form salts (e.g. hydrochloride, hydrobromide, hydroiodide, sulphate, citrate or tartrate) or with, for example, methyl chloride or bromide, ethyl bromide, dimethyl sulphate, ethyl nitrate or benzyl chloride to form quaternary compounds. Alternatively the a -halodiphenyl acetyl halide is reacted with a methylaminoalkyl halide and the product is reacted with a secondary amine to give the aminoalkyl benzilamide or hydrohalide thereof. In examples: (1) N,N-diethylN1 - methylethylene diamine is reacted with a -chlorodiphenylacetyl chloride and the mixture refluxed, cooled and treated with water. Extraction with hydrochloric acid and heating the extract gives N-(2-diethylaminoethyl)-N-methyl benzilamide hydrochloride which on treatment with methyl chloride gives 2-(N-methylbenzilamido) ethyl diethyl methylammonium bromide; (2) and (3) the chloride and methosulphate are prepared similarly. In further examples there are prepared by generally similar methods: (4) 2-(N-methylbenzilamido) ethyl triethyl ammonium bromide; (5) N-2-(di-isopropylaminoethyl)-N-methylbenzilamide hydrochloride and the corresponding methobromide; (6) 2-(N-methylbenzilamido) ethyl trimethyl ammonium bromide; (7) 2-(N-methylbenzilamido) ethyl dimethyl ethylammonium bromide; (8) 3-(N-methylbenzilamido) propyl trimethylammonium bromide; (9) the corresponding ethyl dimethylammonium compounds; (15) N-(morpholinoethyl) - N - methyl benzilamide, its hydrochloride and methobromide; (16) 2-(N-methylbenzilamido) ethyl diethyl benzylammonium chloride. In Examples (11) to (14), hydrochlorides corresponding to the free bases subjected to quaternation in Examples (1), (6), (8) and (10) respectively are isolated. (10) 3-(N-methylbenzilamido) propyl methyl diethyl ammonium bromide. Starting materials. N,N - di - isopropyl - N1-methylethylenediamine is prepared by reacting 2-di-isopropylaminoethyl chloride hydrochloride with methylamine. N,N,N1-trimethyl ethylene diamine is prepared similarly. N,N,N1 - trimethyl - 1,3 - propanediamine is obtained by the reduction with lithium aluminium hydride of N,N-dimethyl-N1 - formyl - 1,3 - propanediamine, itself obtained by refluxing formic acid with dimethylaminopropylamine. Specification 438,659, [Group IV], is referred to.ALSO:A therapeutic composition comprises an antisecretory or antispasmodic compound of the general formula <FORM:0761799/VI/1> wherein Y is lower alkylene of at least 2 carbon atoms (preferably ethylene), R and R1 are each a lower alkyl radical (preferably of 1 to 3 carbon atoms) or, together with N, form a heterocyclic ring, R11 is hydrogen or (preferably) a lower alkyl or an aralkyl radical, and X is an anion (preferably chlorine, bromine, iodine or methosulphate), the terms "lower alkyl" and "lower alkylene" denoting branched as well as straight chain groups having two to six carbon atoms, together with a carrier, preferably solid but which may also be a liquid such as a syrup or aqueous-alcoholic medium. Tablets, powder packets, capsules or other dosage forms may be prepared and other active ingredients such as neutralizers and/or antacids may be incorporated. Lactose talc, stearic acid, magnesium stearate, carbomethoxycellulose and hydrated alumina are suitable excipients and starch is a suitable filler and disintegrator. One-piece gelatine capsules may contain the compounds mixed with corn oil. Typical formul for tablets contain 2-(N-methyl-benzilamido)-ethyl diethyl methyl ammonium bromide with (A) hydrated alumina, aqueous starch, stearic acid, magnesium stearate and cornstarch and (B) sodium carboxymethyl-cellulose, aqueous starch, magnesium stearate, isopropanol and cornstarch. Specification 438,659 [Group IV] is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US761799XA | 1953-04-09 | 1953-04-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB761799A true GB761799A (en) | 1956-11-21 |
Family
ID=22130432
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9294/54A Expired GB761799A (en) | 1953-04-09 | 1954-03-30 | Benzilamide derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB761799A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3373195A (en) * | 1967-03-07 | 1968-03-12 | Squibb & Sons Inc | 2-substituted aminomethylcyclooctyl amides of alkyl substituted acetic acid |
EP0098743A1 (en) * | 1982-06-30 | 1984-01-18 | Ruey J. Dr. Yu | Phenyl alpha-acyloxyacetamide derivates and their therapeutic use |
-
1954
- 1954-03-30 GB GB9294/54A patent/GB761799A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3373195A (en) * | 1967-03-07 | 1968-03-12 | Squibb & Sons Inc | 2-substituted aminomethylcyclooctyl amides of alkyl substituted acetic acid |
EP0098743A1 (en) * | 1982-06-30 | 1984-01-18 | Ruey J. Dr. Yu | Phenyl alpha-acyloxyacetamide derivates and their therapeutic use |
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