C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/315.05, 260/
C07D 235/02 (2006.01) C07D 311/22 (2006.01) C07D 471/10 (2006.01) C07D 491/10 (2006.01) C07D 495/10 (2006.01)
Patent
CA 1088945
ABSTRACT OF THE DISCLOSURE A series of spiro-hydantoin compounds of the formula Image ...I and the base salts thereof with pharmacologically acceptable cations, wherein A is Image , Image IV V Image , Image and Image , VI VII VIII wherein W is -(CH2)n-; X is hydrogen and X2 is fluorine, hydroxy or 6'-(lower alkoxy); or X and X2, when taken separately, are each lower alkoxy, and when taken together are -OCH2(CH2)nO-; X3 is hydrogen and X4 is fluorine, chlorine or bromine; or X3 and X4, when taken separately, are each chlorine, and when taken together are -OCH2(CH2)nO- X5 is hydrogen and X6 is fluorine, hydroxy or lower alkoxy; or X5 and X6, when taken separately, are each chlorine or lower alkoxy, and when taken together are -OCH2(CH2)nO-; X7 is hydrogen and X8 is hydrogen, fluorine, chlorine, bromine or lower alkoxy; or X7 and X8, when taken separately, are each chlorine or lower alkoxy, and when taken together are -OCH2(CH2)nO; Y is oxygen or sulfur; Q is -?- or Image ; and n is zero or one, has been prepared by condensing the appropriate carbonyl ring compound, such as the corresponding 1-indanone, 1-tetralone, 4-chromanone, thiochroman-4-one, 7,8-dihydroquinoline-5-(6H)-one, 6,7-dihydropyridin-5(5H)- one, thiodane-3-one-1,1-dioxide and 4-oxoisothiochroman- 2,2-dioxide, respectively, with potassium cyanide and ammonium carbonate. The resulting hydantoin derivatives are found to be useful in preventing or alleviating chronic diabetic complications. Preferred member compounds include spiro-[imidazolidine-4,1'-indan]-2,5-dione, 6-fluoro- spiro-[chroman-4'4-imiadazolidine]-2',5'-dione, 6-chloro- spiro-[chroman-4,4'-imidazolidine]-2',5'-dione, 6,7-di- chloro-spiro-[chroman-4,4'-imidazolidine]-2',5'-dione, 6,8-dichloro-spiro-chroman-4,4'-imidazolidine]-2',5'- dione, 6'-fluoro-spiro-[imidazolidine-4,4'-thiochroman]- 2,5-dione and 6',7'-dichloro-spiro-[imidazolidine-4,4'- thiochroman]-2,5-dione.
287868
Sarges Reinhard
Gowling Lafleur Henderson Llp
Limited Pfizer
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