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US 9,518,033 B2Granted
(4E)-4-(4-substituted benzylideneamino)-2,3-dihydro-3-substituted-2-thioxothiazole-5-carbonitriles as A2AR antagonist and process for preparation thereof
AssigneeCouncil of Scientific and Industrial Research
InventorsPratibha Mehta Luthra, Chandrabhushan Mishra
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Abstract
The present invention provides (4E)-4-(4-substituted benzylideneamino)-2,3-dihydro-3-substituted-2-thioxothiazole-5-carbonitriles of general formula A, below, and a process for the preparation thereof. The compounds of present invention are useful in the treatment of central nervous disorders including, Parkinson disease, Huntington's disease, attention disorder, cognition, Alzheimer disease, depression and hypertension.
Claims7
A compound of formula A and pharmaceutically acceptable salts thereof,
- wherein R is selected from the group consisting of hydrogen, alkyl having carbon numbers up to 10, cycloalkyl, aromatic, aromatics having substituents selected from the group consisting of halogen, OH, COOH, OCH3, and alkyl, and substituted heterocyclics including heteroaromatics compounds having up to seven members;
- R1 is selected from nucleophiles selected from the group consisting of halides, O along with a substituent selected from the group consisting of hydrogen, alkyl having carbon numbers up to 10, cycloalkyl, aromatic, aromatics having substituents selected from the group consisting of halogen, OH, COOH, OCH3, and alkyl, and substituted heterocyclics including heteroaromatics compounds having up to seven members, S along with a substituent selected from the group consisting of hydrogen, alkyl having carbon numbers up to 10, cycloalkyl, aromatic, aromatics having substituents selected from the group consisting of halogen, OH, COOH, OCH3, and alkyl, and substituted heterocyclics including heteroaromatics compounds having up to seven members, COO along with a substituent selected from the group consisting of hydrogen, alkyl having carbon numbers up to 10, cycloalkyl, aromatic, aromatics having substituents selected from the group consisting of halogen, OH, COOH, OCH3, and alkyl, and substituted heterocyclics including heteroaromatics compounds having up to seven members, NR2R3 wherein R2 and R3 are selected from the group consisting of hydrogen, alkyl having carbon numbers up to 10, cycloalkyl, aromatic, aromatics having substituents selected from the group consisting of halogen, OH, COOH, OCH3, and alkyl, substituted heterocyclics including heteroaromatics compounds having up to seven members and substituted amino, and alkyl having up to five carbon chain.
A pharmaceutical compound selected from the group consisting of:
- a. 4E)-4-(4-fluorobenzylideneamino)-3-ethyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- b. (4E)4-(4-fluorobenzylideneamino)-3-propyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- c. (4E)-4-fluorobenzylideneamino)-3-butyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- d. (4E)-4-(4-fluorobenzylideneamino)-3-phenylethyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- e. (4E)-4-(4-fluorobenzylideneamino)-3-phenyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- f (4E)-4-(4-chlorobenzylideneamino)-3-ethyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- g. (4E)4-(4-chlorobenzylideneamino)-3-propyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- h. (4E)-4-(chlorobenzylideneamino)-3-butyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- i. (4E)4-(4-chlorobenzylideneamino)-3-phenyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile
- j. (4E)-4-(4-Bromobenzylideneamino)-3-ethyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- k. (4E)4-(4-bromobenzylideneamino)-3-propyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- l. (4E)-4-(4-bromobenzylideneamino)-3-butyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile,
- m. (4E)4-(4-bromobenzylideneamino)-3-phenylethyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile, and
- n. (4E)4-(4-bromobenzylideneamino)-3-phenyl-2,3-dihydro-2-thioxothiazole-5-carbonitrile.
11 more elements
Dependencies are inferred from the claim text.