Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-03-10
1996-12-31
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540545, 540546, C07D49822, A61K 3155, A61K 3138
Patent
active
055894720
DESCRIPTION:
BRIEF SUMMARY
SUMMARY OF THE INVENTION
The invention relates to compounds of the formula ##STR2## or pharmaceutically acceptable salts thereof, wherein X and Y are independently .dbd.O, .dbd.NH, (H,H) or (H,OH); or --CH.sub.3 ; ##STR3## S, SO, or SO.sub.2 : R.sub.3 is --H, --OH, --NH.sub.2, --C.sub.1 -C.sub.10 alkyl, ##STR4## --CH.sub.2 Ph, --Ar, heteroaromatic, --(CH.sub.2).sub.n CO.sub.2 H, --(CH.sub.2).sub.2 OH, --CH(CH.sub.2 OH).sub.2, --C(CH.sub.2 OH).sub.3, --CH.sub.2 CH.sub.2 (N(CH.sub.3).sub.2), --CH.sub.2 CH.sub.2 NH.sub.2, --NHCH.sub.3, aralkyl, --N(CH.sub.3).sub.2 ; ##STR5## --CH.sub.2 CH.sub.2 SH, CH.sub.2 CH.sub.2 SCH.sub.3, --CH.sub.2 CO.sub.2 CH.sub.3, --CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3, --CH.sub.2 CN; --CH.sub.2 CH.sub.2 N.sub.3 and ##STR6## n is 1 or 2; m is 0, 1, 2 or 3; selected from the group consisting of H, --(CH.sub.2).sub.p OH, --(CH.sub.2).sub.q NH.sub.2, --(CH.sub.2).sub.r NHCH.sub.3, --(CH.sub.2).sub.s N (CH.sub.3).sub.2, --(CH.sub.2).sub.t OCH.sub.3, --(CH.sub.2).sub.u CO.sub.2 CH.sub.3, --CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 CO.sub.2 tert-Bu., --CH.sub.2 CO.sub.2 tert-Bu., --CH.sub.2 CH.sub.2 CO.sub.2 t Bu., and --(CH.sub.2).sub.v CO.sub.2 H --(CH.sub.2).sub.w CONH.sub.2 ; ##STR7## S, or SO, R.sub.4 and R.sub.5 are both H.
Preferred are compounds of formula I wherein Z is N--R.sub.3. Among these are preferred compounds wherein R.sub.3 is aralkyl, or especially --(CH.sub.2).sub.n CO.sub.2 H, --(CH.sub.2).sub.2 OH, --CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2, --CH.sub.2 CH.sub.2 SH, --CH.sub.2 CH.sub.2 SCH.sub.3, --CH.sub.2 CO.sub.2 CH.sub.3, --CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3, or --CH.sub.2 CN. Also preferred are compounds of formula I wherein R.sub.3 is --H, --OH or --CH.sub.3. Also preferred are compounds of formula I wherein R.sub.3 is --CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2. Also preferred are compounds of formula I wherein Z is N--R.sub.3, X and Y are both O and R.sub.3 is --CH.sub.2 CH.sub.2 OH.
Also preferred are compounds of formula I wherein Z is S. Among these compounds wherein only one of X and Y is O, are especially preferred.
Also preferred are compounds of formula I wherein Z is SO.
Also preferred are compounds of formula I wherein Z is SO.sub.2.
Also preferred are compounds of formula I wherein Z is O.
Also preferred are compounds of formula I wherein X and Y are both O.
Also preferred are compounds of formula I wherein R.sub.1 and R.sub.2 are both H.
Also preferred are compounds of formula I wherein Z is SO.sub.2 and R.sub.4 and R.sub.5 are both H.
Exemplary of compounds of formula I of the invention are: ##STR8##
The most preferred compound of the invention is: ##STR9##
The invention also relates to a pharmaceutical composition comprising a therapeutically effective amount of a compound of formula I in combination with a pharmaceutically acceptable carrier.
The invention relates to a method of treating inflammation which comprises administering to a mammal in need of such treatment an anti-inflammatory effective amount of a compound of formula I for such purpose.
The invention also relates to a method of treating tumors which comprises administering to a mammal in need of such treatment an anti-tumor effective amount of a compound of formula I for such purpose.
The invention also relates to a method for treating psoriasis which comprises administering to a mammal in need of such treatment an anti-psoriatically effective amount of a compound of formula I for such purpose.
The invention also relates to a method for synthesizing compounds of formula I of the invention.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of formula I can exist in unsolvated as well as solvated forms, including hydrated forms, e.g. the hemihydrate. In general, the solvated forms, with pharmaceutically acceptable solvents such as water, ethanol, and the like are equivalent to the unsolvated forms for the purposes of the invention.
Certain compounds of the invention can exist in stereoisomeri
REFERENCES:
Liebigs Annalen Derchemie, No. 6, 1976 Weinhem pp. 1090-1102.
Fabre et al. Biorganic letters, vol. 2, No. 4, pp. 449-452, 1992.
5th Symposium Blackbury VA, Oct. 2, 1992.
Weinreb et al, Heterocycles, vol. 21, No. 1, 1984 pp. 309-316, 324.
Boxer Matthew
Maitner John J.
Shah Mukund J.
Sripada Pavanaram K.
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