GB684111A - Improvements in or relating to anthelmintic drugs - Google Patents
Improvements in or relating to anthelmintic drugsInfo
- Publication number
- GB684111A GB684111A GB16170/51D GB1617051D GB684111A GB 684111 A GB684111 A GB 684111A GB 16170/51 D GB16170/51 D GB 16170/51D GB 1617051 D GB1617051 D GB 1617051D GB 684111 A GB684111 A GB 684111A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acids
- ketobutyric
- isopropylphenyl
- substituted
- pseudocumyl
- 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
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises lactones of the formula <FORM:0684111/IV (b)/1> where Ph is a substituted phenyl group containing either two or more alkyl groups or at least one alkyl group of two or more carbon atoms. These are made from the corresponding g -phenyl-g -ketobutyric acids by (1) reduction to hydroxy-acids and dehydration or (2) dehydration of the enolic forms to give substituted crotonolactones which are then hydrogenated. Salts or esters of the acids may be used, these being hydrolysed before ring closure. Reduction may be by nascent hydrogen (sodium amalgam or zinc), catalytic hydrogenation (nickel or palladium) or the Meerwein-Ponndorf reaction (isopropanol). In the examples, the following g -substituted g -ketobutyric acids are converted into hydroxy-acids and ring-closed: 4-ethylphenyl, 3 : 4-dimethylphenyl, 4 - propylphenyl, 4 - isopropylphenyl, cymyl (mixture of 2 isomers), 4-butylphenyl, 4-isobutylphenyl, 4-isoamylphenyl, 4-n-hexylphenyl and pseudocumyl. g -4-Isopropylphenyl-g -ketobutyric ethyl ester is also reduced to the hydroxyester which is then hydrolysed to the free acid before ring-closure. In a further example, g -4-isopropylphenyl-g -ketobutyric acid is heated with acetic anhydride to yield g -4-isopropylphenyl-crotonolactone, which is then hydrogenated. g - Pseudocumyl - g - ketobutyric acid is obtained from pseudocumene, succinic anhydride and aluminium chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE684111X | 1949-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB684111A true GB684111A (en) | 1952-12-10 |
Family
ID=6597526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16170/51D Expired GB684111A (en) | 1949-06-30 | 1950-06-28 | Improvements in or relating to anthelmintic drugs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB684111A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0069409A1 (en) * | 1981-07-02 | 1983-01-12 | Stamicarbon B.V. | Process for the preparation of a 5-alkyl-butyrolactone |
-
1950
- 1950-06-28 GB GB16170/51D patent/GB684111A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0069409A1 (en) * | 1981-07-02 | 1983-01-12 | Stamicarbon B.V. | Process for the preparation of a 5-alkyl-butyrolactone |
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