Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity

Claim 1

A compound of the formula ##STR11## where X is O; R is hydrogen or lower alkyl; A is thienyl or furyl; n is 0-4; and B is H, --COOH or a pharmaceutically acceptable salt thereof, or an ester thereof with a saturated aliphatic alcohol of ten or fewer carbon atoms, or with a cyclic or saturated aliphatic cyclic alcohol of 5 to 10 carbon atoms, or with phenol or with a lower alkylphenol, or an amide or a mono or di-substituted amide thereof, the substituents on the amide being selected from a group consisting of saturated aliphatic radicals of ten or fewer carbon atoms, cyclic or saturated aliphatic cyclic radicals of 5 to 10 carbon atoms, and phenyl or lower alkylphenyl radicals, or B is CH 2 OH or an ester derivative thereof derived from a saturated aliphatic acid of ten or fewer carbon atoms, or from a cyclic or saturated aliphatic cyclic acid of 5 to 10 carbon atoms, or from benzoic acid, or an ether derivative thereof derived from a saturated aliphatic radical of ten or fewer carbon atoms, or from a cyclic or saturated aliphatic cyclic radical of 5 to 10 carbon atoms, or from phenyl or lower alkylphenyl radical, or B is --CHO or a lower alkyl acetal derivative thereof, or an acetal derivative thereof formed with a lower alkyl, diol, or B is --COR 1 or a lower alkyl ketal derivative thereof, or a ketal derivative thereof formed with a lower alkyl diol, where R 1 is --(CH 2 ) m CH 3 where m is 0-4, or a pharmaceutically acceptable salt of the compound defined in said formula.

Claim 23

A method of treating psoriasis in a mammal which method comprises administering alone or in conjunction with a pharmaceutically acceptable excipient, a therapeutically effective amount of a compound of the formula ##STR13## where X is O; R is hydrogen or lower alkyl; A is thienyl, or furyl; n is 0-4; and B is H, --COOH or a pharmaceutically acceptable salt thereof, or an ester thereof with a saturated aliphatic alcohol of ten or fewer carbon atoms, or with a cyclic or saturated aliphatic cyclic alcohol of 5 to 10 carbon atoms, or with phenol or with a lower alkylphenol, or an amide or a mono or di-substituted amide thereof, the substituents on the amide being selected from a group consisting of saturated aliphatic radicals of ten or fewer carbon atoms, cyclic or saturated aliphatic cyclic radicals of 5 to 10 carbon atoms, and phenyl or lower alkylphenyl radicals, or B is CH 2 OH or an ester derivative thereof derived from a saturated aliphatic acid of ten or fewer carbon atoms, or from a cyclic or saturated aliphatic cyclic acid of 5 to 10 carbon atoms, or from benzoic acid, or an ether derivative thereof derived from a saturated aliphatic radical of ten or fewer carbon atoms, or from a cyclic or saturated aliphatic cyclic radical of 5 to 10 carbon atoms, or from phenyl or lower alkylphenyl radical, or B is --CHO or a lower alkyl acetal derivative thereof, or an acetal derivative thereof formed with a lower alkyl, diol, or B is --COR 1 or a lower alkyl ketal derivative thereof, or a ketal derivative thereof formed with a lower alkyl diol, where R 1 is --(CH 2 ) m CH 3 where m is 0-4, or a pharmaceutically acceptable salt of the compound defined in said formula.

Claim 24

A method of treating psoriasis in a mammal which method comprises administering alone or in conjunction with a pharmaceutically acceptable excipient, a therapeutically effective amount of a compound of the formula ##STR13## where X is O; R is hydrogen or lower alkyl; A is thienyl, or furyl; n is 0-4; and B is H, --COOH or a pharmaceutically acceptable salt thereof, or an ester thereof with a saturated aliphatic alcohol of ten or fewer carbon atoms, or with a cyclic or saturated aliphatic cyclic alcohol of 5 to 10 carbon atoms, or with phenol or with a lower alkylphenol, or an amide or a mono or di-substituted amide thereof, the substituents on the amide being selected from a group consisting of saturated aliphatic radicals of ten or fewer carbon atoms, cyclic or saturated aliphatic cyclic radicals of 5 to 10 carbon atoms, and phenyl or lower alkylphenyl radicals, or B is CH 2 OH or an ester derivative thereof derived from a saturated aliphatic acid of ten or fewer carbon atoms, or from a cyclic or saturated aliphatic cyclic acid of 5 to 10 carbon atoms, or from benzoic acid, or an ether derivative thereof derived from a saturated aliphatic radical of ten or fewer carbon atoms, or from a cyclic or saturated aliphatic cyclic radical of 5 to 10 carbon atoms, or from phenyl or lower alkylphenyl radical, or B is --CHO or a lower alkyl acetal derivative thereof, or an acetal derivative thereof formed with a lower alkyl, diol, or B is --COR 1 or a lower alkyl ketal derivative thereof, or a ketal derivative thereof formed with a lower alkyl diol, where R 1 is --(CH 2 ) m CH 3 where m is 0-4, or a pharmaceutically acceptable salt of the compound defined in said formula.