New benzisoselenazolones, process for producing the same and pharmaceutical preparations containing the same

Claim 2

B enzisoselenazolones having the general formula I wherein R 1 and R 2 which may be the same or different from each other, represent hydrogen, fluorine, chlorine, bromine, C 1 to 4 -alkyl, C 1 to 4 -alkoxy, hydroxy, trifluoromethyl, nitro, or R 1 and R 2 together represent the methylenedioxy group-O-CH 2 -O-, R 3 and R 4 which may be the same or different from each other, represent hydrogen, fluorine, chlorine, bromine, C 1 to 4 - alkyl, C 1 to 4 -alkoxy, hydroxy, trifluoromethyl, nitro, di-(C 1 to 4 -alkyl)-amino or, R 3 and R 4 together, represent the methylenedioxy group-O-CH 2 -O-or R 3 represents hydrogen with R 4 being -CN, -COOR 5 or wherein R 5 is hydrogen, an alkali metal ion or C 1 to 4 -alkyl and R 6 being hydrogen, methyl or ethyl, and n is 0 or an integer from 1 to 4, with the exclusion of the compounds of formula I, wherein n is 0, R 1 , R 2 and R 3 are hydrogen and R 4 is hydrogen or o-methyl or n is 1 and R 1 , R 2 , R 3 and R 4 are hydrogen.

Claim 3

2 . B enzisoselenazolones as claimed in claim 1 wherein in formula I n is 0 and either R 1 and R 2 or R 1 and R 3 represent hydrogen with the other substituents being fluorine, chlorine, bromine, hydroxy, methoxy, methyl, trifluoromethyl and/or nitro.

Claim 4

Benzisoselenazolones as claimed in claim 1 wherein in formula I n is 0 or an integer from 1 to 4, R 1 , R 2 and R 3 represent hydrogen and R 4 is -CN, -COOR 5 or R 5 being H, Na ⊕ , -CH 3 or -C 2 H 5 and R 6 being H, -CH 3 or -C 2 H 5 •

Claim 5

2-Methylseleno-benzamides having the general formula II wherein R 1 , R 2 , R 3 , R 4 and n have the same meaning as in formula I according to claims 1 to 3.

Claim 6

Process for the production of benzisoselenazolones according to claims 1 to 3 characterized in that a) a 2-methylseleno-benzoic acid having the general formula III wherein R 1 and R 2 have the same meaning as in formula I, is subjected to reaction with an inorganic acid chloride, the resulting benzoyl chloride having the general formula IV wherein R 1 and R 2 have the same meaning as in formula I, is subjected to reaction with an amine having the general formula V wherein R 31 R 4 and n have the same meaning as in formula I,under ring closure conditions to yield the benzisoselenazolones of the general formula I, or b) a 2-methylseleno-benzamide having the general formula II according to claim 4 is subjected to ring closure in the presence of an inorganic acid chloride to yield a 3-chloro-1.2-benzisoselenazolonium compound having the general formula VI wherein R 1 , R 2 , R 3 , R 4 and n have the same meaning as in formula I, and the compound of formula VI thereafter is subjected to hydrolysis to yield the corresponding benzisoselenazolone of formula I, or c) a 2-methylseleno-benzamide having the general formula II is subjected to reaction with bromine and thereafter heated, possibly in the presence of an organic acid or base, and the resulting benzisoselenazolone of formula I is separated from the reaction mixture.

Claim 7

Pharmaceutical preparations comprising a benzisoselenazolone according to any of claims 1 to 3 together with usual pharmaceutical diluents or carrier materials.