GB880790A - Cyclohexene-carboxylic acid amides - Google Patents
Cyclohexene-carboxylic acid amidesInfo
- Publication number
- GB880790A GB880790A GB13460/58A GB1346058A GB880790A GB 880790 A GB880790 A GB 880790A GB 13460/58 A GB13460/58 A GB 13460/58A GB 1346058 A GB1346058 A GB 1346058A GB 880790 A GB880790 A GB 880790A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexene
- nitrile
- alkyl
- butyl
- carbon atoms
- 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
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises cyclohexene-carboxylic acid amides of the general formula <FORM:0880790/IV (b)/1> in which R represents an alkyl or alkenyl radical containing 2 to 5 carbon atoms. The products are employed in anti-convulsive preparations (see Group VI). The above compounds may be prepared by condensing the 1-alkali metal compound of cyclohexene-(3)-nitrile with an alkylating or alkenylating agent comprising a saturated alkyl halide, a mono-olefinic alkenyl halide or a dialkyl sulphate, the alkyl or alkenyl groups of which contain from 2 to 5 carbon atoms and hydrolysing the cyclohexene-(3)-nitrile alkylated or alkenylated in the 1- position so formed at temperatures between 50 DEG C. and 150 DEG C. by means of caustic alkali in the presence of an aliphatic alcohol. The alkali metal compounds of cyclohexene -(3)-nitrile may be reacted with the reactive esters in liquid ammonia or a mixture of the ester and cyclohexene-(3)-nitrile may be added to a suspension of sodamide in boiling benzene. Other hydrocarbon solvents may be employed. Examples are furnished relating to the preparation of 1-n-propyl-, -sec-butyl-, -alkyl-, -crotyl-, isobutyl, -ethyl and isoamyl-cyclohexene-(3)-nitrile-(1) and the hydrolysis thereof to the corresponding amides. Cyclohexene-(3)-nitrile is obtained by reacting butadiene with acrylonitrile. The sodium compound thereof is obtained by reacting the nitrile with sodium phenyl in the presence of aromatic hydrocarbons or with sodamide in liquid ammonia.ALSO:An anti-convulsive preparation suitable for oral administration comprises an amide of the general formula <FORM:0880790/VI/1> in which R represents an alkyl or alkenyl radical containing 2 to 5 carbon atoms (see Group IV (b)) in admixture with a pharmaceutical carrier material. Specific amides described are 1 - n - propyl -, 1 - sec - butyl, 1 - allyl -, 1 - crotyl -, 1 - isobutyl -, 1 - n - butyl -, and 1 - ethyl - cyclohexene - (3) - carboxylic acid amides-(1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1048575X | 1957-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB880790A true GB880790A (en) | 1961-10-25 |
Family
ID=6825159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13460/58A Expired GB880790A (en) | 1957-04-27 | 1958-04-28 | Cyclohexene-carboxylic acid amides |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1048575B (en) |
| FR (1) | FR1203847A (en) |
| GB (1) | GB880790A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH641756A5 (en) * | 1978-04-27 | 1984-03-15 | Sanofi Sa | COMPOUNDS DERIVED FROM CYCLOHEXYLCARBOXYLIC ACID, AND MEDICAMENTS CONTAINING THEM. |
| JPS57181032A (en) * | 1981-03-05 | 1982-11-08 | Hisamitsu Pharmaceut Co Inc | Novel cyclohexene derivative |
-
0
- DE DENDAT1048575D patent/DE1048575B/en active Pending
-
1958
- 1958-04-28 GB GB13460/58A patent/GB880790A/en not_active Expired
- 1958-04-28 FR FR1203847D patent/FR1203847A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1048575B (en) | 1959-01-15 |
| FR1203847A (en) | 1960-01-21 |
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