Substituted carbamic acid quinolin-6-yl esters useful as acetylcholinesterase inhibitors
AssigneeCouncil of Scientific and Industrial Research
InventorsNeeraj Shakya, Zeeshan Fatima, Chandishwar Nath, Anil Saxena
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Abstract
The present invention relates to new substituted carbamic acid quinoline-6-yl esters of formulae 1 and 2 where R1=alkyl, aryl; R2=H, alkyl, aralkyl useful as acetylcholinesterase inhibitors, and which show potent antiacetylcholinesterase activity and have potential therapeutic use for prevention or cure of acetylcholinesterase related disorders including peripheral as well as central nervous system.
Claims23
A substituted carbamic acid quinolinyl ester represented by formula 1 and 2 below:
- wherein R1=alkyl, aryl, R2=H, alkyl, aralkyl.
A compound as claimed in claim I wherein the substituted carbamic acid quinolinyl ester is selected from the group consisting of
- 1a. hexyl-carbamic acid quinolin-6-yl ester
- 1b. heptyl-carbamic acid quinolin-6-yl ester
- 1c. (2-chloro-phenyl)-carbamic acid quinolin-6-yl ester
- 1d. (3-bromo-phenyl)-carbamic acid quinolin-6-yl ester
- 2a. hexyl-carbamic acid 1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2b. heptyl-carbamic acid 1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2c. (3-bromo-phenyl)-carbamic acid 1,2,3,4-tetrahydro-quinolin-6-yl ester
- 2d. (2-chloro-phenyl)-carbamic acid 1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2e. (4-chloro-3-trifluoromethyl-phenyl)-carbamic acid 1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2f. (4-bromo-phenyl)-carbamic acid 1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2 g. heptyl-carbamic acid 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2 h. hexyl-carbamic acid 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2i. (2-chloro-phenyl)-carbamic acid 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2j. (3-bromo-phenyl)-carbamic acid 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2k. (4-chloro-3-trifluoromethyl-phenyl)-carbamic acid 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2l. (4-bromo-phenyl)-carbamic acid 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2m. hexyl-carbamic acid 1-methyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2n. heptyl-carbamic acid 1-methyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2o. (2-chloro-phenyl)-carbamic acid . -methyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2p. (3-bromo-phenyl)-carbamic acid 1-methyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2q. (4-chloro-3-trifluoromethyl-phenyl)-carbamic acid 1-methyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
- 2r. (4-bromo-phenyl)-carbamic acid 1-methyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester
A process for the synthesis of a quinoline derivative represented by formula 1 and 2 below:
- wherein R1=alkyl, aryl;
- R2=H, alkyl, aralkyl, the process comprising reacting a substituted phenol with an isocyanate in the presence of abase and at least one organic solvent using a base and at least one organic solvent to obtain the corresponding carbamic acid ester (carbamates) of formulae 1 or 2.
A method for treatment of hypofunctioning of cholinergic system in a subject, comprising administering a pharmaceutically effective amount of compound of formulae 1 or 2
- wherein R1=alkyl, aryl;
- R2=H, alkyl, aralkyl, to a subject suffering from hypofunctioning of cholinergic system
Dependencies are inferred from the claim text.