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Tricyclic pyrazole derivatives as cannabinoid receptor modulators

a technology of cannabinoid receptor and tricyclic pyrazole, which is applied in the direction of heterocyclic compound active ingredients, biocide, drug compositions, etc., can solve the problem of few medicines availabl

Inactive Publication Date: 2010-10-28
CADILA HEALTHCARE LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention describes new compounds that can mimic the effects of cannabinoids, which are used to treat various symptoms in humans and other mammals. These compounds can act as antagonists of the cannabis CBI-receptor, which is the target of cannabinoids. The invention provides methods for preparing and using these compounds for treating diseases that can be treated with cannabis or its derivatives. The technical effects of the invention include providing new tools for research and development of cannabinoid-based medicines and treating diseases with these compounds.

Problems solved by technology

Though research in the area of cannabinoids have been going on for more than a decade there are only few medicines available which modulate the cannabinoid receptors and fewer with minor side effects.

Method used

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  • Tricyclic pyrazole derivatives as cannabinoid receptor modulators
  • Tricyclic pyrazole derivatives as cannabinoid receptor modulators
  • Tricyclic pyrazole derivatives as cannabinoid receptor modulators

Examples

Experimental program
Comparison scheme
Effect test

example 1

4-Chloro-N-{[8-chloro-1-(2,4-dichloro-phenyl)-1,4,5,6-tetrahydro-1,2-diaza-benzo[e]azulene-3-yl]methylamino-methylene)-benzenesulfonamide

[0103]8-chloro-1-(2,4-dichloro-phenyl)-1,4,5,6-tetrahydro-1,2-diaza-benzo[e]azulene-3-carboxylic acid was prepared by suitable modifications of similar techniques and processes known in the art.

Step A

4-Chloro-N (8-chloro-1-(2,4-dichloro-phenyl)-1,4,5,6-tetrahydro-1,2-diaza-benzo[e]azulene-3-carbonyl)-benzene-sulfonamide

[0104]8-Chloro-1-(2,4-dichloro-phenyl)-1,4,5,6-tetrahydro-1,2-diaza-benzo[e]azulene-3-carboxylic acid (4.3 g, 10.55 mmol) was converted into acid chloride using thionyl chloride (2.31 mL, 31.66 mmol) in toluene by refluxing at ca. 110° C. over a period of 1 h.

[0105]The solvents were evaporated under reduced pressure. The residue obtained was taken in dichloromethane (20 mL) and the resulting solution was added to the cooled suspension of 4-chloro benzene sulfonamide (2.7 g, 4.137 mmol) and TEA (1.97 mL, 14.137 mmol) in dichloromethan...

example 2

Hydrochloride salt of 8-chloro-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-6-oxa-1,2-diaza-benzo[e]azulene-3-carboxylic acid piperidin-1-ylamide

[0110]a) 8-Chloro-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-6-oxa1,2-diaza benzo[e]azulene-3-carboxylic acid by suitable modifications of similar techniques and processes known in the art.

[0111]b) Hydrochloride salt of 8-Chloro-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-6-oxa 1,2-diaza benzo[e]azulene-3-carboxylic acid piperidin-1-yl-amide (Compound 2). 8-chloro-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-6-oxa 1,2-diaza-benzo[e]azulene-3-carboxylic acid (0.500 g, 1.221 mmol) was coupled with 1-amino-piperidine (0.197 mL, 1.832 mmol) in presence of 1-Hydroxy-benzotriazole monohydrate (HOBt. H2O), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC-HCl) and TEA in dichloromethane (25 mL) at ca. 27° C. over a period of 25-30 min. The reaction was diluted with H2O (30 mL) and extracted with dichloromethane. The dichloromethane layer was separated, ...

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Abstract

The present invention relates to novel compounds of general formula (I),their regioisomers, tautomeric forms, novel intermediates involved in their synthesis. The present invention also relates to a process of preparing compounds of general formula (I), their regioisomers, their tautomeric forms, their pharmaceutically acceptable salts, pharmaceutical compositions containing them, and novel intermediates involved in their synthesis.

Description

FIELD OF INVENTION[0001]The present invention relates to novel compounds of general formula (I), their regioisomers, tautomeric forms, novel intermediates involved in their synthesis, their pharmaceutically acceptable salts and pharmaceutical compositions containing them. The present invention also relates to a process of preparing compounds of general formula (I), their regioisomers, their tautomeric forms, their pharmaceutically acceptable salts, pharmaceutical compositions containing them, and novel intermediates involved in their synthesis.BACKGROUND AND PRIOR ART[0002]Cannabinoids are present in Indian hemp Cannabis saliva and have been well known for their medicinal properties for ages. Cannabinoids as a therapeutic agents is however a recent phenomenon. (Williamson E. M. & Evans E. J. Drugs 2000 December; 60(6): 1303-14) Research in this area over the last decade have provided very important information on the cannabinoid receptors and their agonists and antagonists. Developm...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/416C07D231/54C07D491/044C07D495/04A61K31/454A61K31/4162A61K31/5377A61K31/496C07C69/738C07D313/08C07D337/08
CPCC07D495/14C07D495/04A61P43/00C07D231/54A61K31/416A61K31/4162
Inventor LOHRAY, BRAJ BHUSHANLOHRAY, VIDYA BHUSHANSRIVASTAVA, BRIJESH
Owner CADILA HEALTHCARE LTD
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