IE49401B1 - N,n-dimethyl-(3-(2-benzyl-2h-indazole-3-yl)propionic acid amide - Google Patents
N,n-dimethyl-(3-(2-benzyl-2h-indazole-3-yl)propionic acid amideInfo
- Publication number
- IE49401B1 IE49401B1 IE239680A IE239680A IE49401B1 IE 49401 B1 IE49401 B1 IE 49401B1 IE 239680 A IE239680 A IE 239680A IE 239680 A IE239680 A IE 239680A IE 49401 B1 IE49401 B1 IE 49401B1
- Authority
- IE
- Ireland
- Prior art keywords
- benzyl
- dimethyl
- indazole
- propionic acid
- acid amide
- Prior art date
Links
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
The Pharmacological studies carried out on laboratory animals have shown that the above compounds possess an anti-inflamatory activity, which manifests itself both through the topical and the systemic route, as well as a local anaesthetic activity and a disinfectant action which manifest themselves only after topical application.
The above compound (I) may be prepared by a variety of routes including the reaction of the anion of 2-benzylindazolin-3-thione (IV) with 3-chloro-N,N-dimethylprop10 anamide followed by reduction of the amide (IX) with a suitable reducing agent e.g. a metal hydride such as, for example, lithium aluminum hydride:
IV
H.AlIi ? I
- 4 The amide (IX) is the novel intermediate of the present invention. As indicated it is prepared by the action of 3-chloro-N,N-dimethyl-propanamide on the anion of the 2benzyl-indazolin-3-thione (IV) in both polar and non-polar solvents.
The preparation of the compound of this invention is illustrated by the following Example.
EXAMPLE
7.6g (0.06 mols) of 3-chloro-propionyl chloride are added dropwise, with stirring, into 60 ml of a 10? solution of dimethyl-amine (0.12 mols) in toluene while cooling with an ice-water mixture. After stirring for 1 hour, while continuously cooling the mixture with ice and water, the solution is filtered (solution A).
To a suspension of 13.15 g (0.05 mols) of the sodium salt of 2-benzyl-indazolin-3-thione in 100 ml of toluene, brought to the boiling point, there is added dropwise, over a period of one half hour, the solution A. The mixture is refluxed for 5.5 additional hours and is then cooled and washed with water. After removal of the solvent, the residue (16.6 g; yield: 89?)shows an NMR spectrum which is in good accordance with the structure (IX)·
Claims (2)
1. The Ν,Ν-dimethylamide of 3-(2-benzyl-2H-indazol-3yl) thiopropionic acid. oL claim i
2. A compoundjSubstantially as hereinbefore described 5 with reference to the Example . Dated this 18th day of February 1980 VA/CRUfOKSHTOK & CO. Β Y = * Γ C EXE C UTIV E 1 ===»—s«==r Agents for the Applicants,
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20305/79A IT1110282B (en) | 1979-02-19 | 1979-02-19 | BASIC THIO-INDAZOLS |
| IE296/80A IE49399B1 (en) | 1979-02-19 | 1980-02-18 | Basic thio-indazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IE49401B1 true IE49401B1 (en) | 1985-10-02 |
Family
ID=26318851
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE239680A IE49401B1 (en) | 1979-02-19 | 1980-02-18 | N,n-dimethyl-(3-(2-benzyl-2h-indazole-3-yl)propionic acid amide |
| IE239583A IE49400B1 (en) | 1979-02-19 | 1980-02-18 | 2-benzyl-3-(-3-chloro or hydroxy propylithio)-indazole,their corresponding sulfoxides and sulfones and process for their preparation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE239583A IE49400B1 (en) | 1979-02-19 | 1980-02-18 | 2-benzyl-3-(-3-chloro or hydroxy propylithio)-indazole,their corresponding sulfoxides and sulfones and process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| IE (2) | IE49401B1 (en) |
-
1980
- 1980-02-18 IE IE239680A patent/IE49401B1/en unknown
- 1980-02-18 IE IE239583A patent/IE49400B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE49400B1 (en) | 1985-10-02 |
| IE832395L (en) | 1980-08-19 |
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