Derivatives of pyrimido[6,1-a]isoquinolin-4-one

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

Reexamination Certificate

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C544S249000, C540S548000, C546S081000, C546S084000

Reexamination Certificate

active

07105663

ABSTRACT:
Compounds of general formula (I) wherein each of R1and R2independently represents a C1-6alkyl or C2-7acyl group; R5represents a hydrogen atom or a C1-3alkyl, C2-3alkenyl or C2-3alkynyl group; R6represents a hydrogen atom or a C1-6alkyl, C2-6alkenyl, C2-6alkynyl, amino, C1-6alkylamino, di(C1-6)alkylamino or C2-7acylamino group, each of R7and R8independently represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C2-7acyl, C1-6alkythio, C1-6alkoxy, C3-6cycloalkyl; and R9represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C2-7acyl, C1-6alkythio, C1-6alkoxy or C3-6cycloalkyl group; X represents OCH2or a group CR3R4, wherein each of R3and R4independently represents a hydrogen atom or a C1-3alkyl group; each of R10and R11independently represents a hydrogen atom, a C1-3alkyl, C3-6cycloalkyl or phenyl group; y represents an oxygen atom or a group CHNO2, NCN, NH or NNO2, n is an integer from 2 to 4; or a salt thereof; are useful for treatment of respiratory disorders such as asthma. Compounds of the invention have a longer duration of action than the known compound trequinsin (9,10-dimethoxy-3-methyl-2-mesitylimino-2,3,6,7-tetrahydro-4H-pyrimido[6,1-a]-isoquinolin-4-one) and do not have trequinsin's very bitter taste.

REFERENCES:
patent: 4400506 (1983-08-01), Lal et al.
patent: 4581172 (1986-04-01), Kaiser et al.
patent: 5141936 (1992-08-01), Rupp et al.
patent: 1 597 717 (1981-09-01), None
De Souza, et al.,J. Med Chem, vol. 27, No. 11, pp. 1470-1480 (1984).

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