Dihydrobenzo(B)thiophenes and pharmaceutical compositions thereof useful as antifungals
AssigneeSchering Corporation
InventorsDinanath F. Rane, Russell E. Pike
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Abstract
2-Alkyl-, 2-alkenyl- and 2-alkynyl-2,3-dihydro-2-(1H-azolyl(C.sub.1 -C.sub.2)alkyl)benzo[b]thiophenes especially 2-alkyl-, 2-alkenyl- and 2-alkynyl-2,3-dihydro-3-hydroxy-2-(1H-1-imidazolylmethyl)-4-,5-,6- and 7-halobenzo[b]thiophenes and related derivatives having antifungal activity are disclosed. Pharmaceutical compositions comprising compounds of the invention and their use in treating fungal infections in susceptible hosts such as humans are also disclosed.
Claims21
A compound represented by the formula I ##STR13## in racemic or optically active form, or a pharmaceutically acceptable salt thereof wherein
- X is one or more groups selected independently from halogen, (lower)alkyl, halo(lower)alkyl, cyano, nitro, substituted and unsubstituted phenyl or substituted and unsubstituted phenyl(lower)alkyl, said phenyl and phenyl(lower)alkyl substituents being one to four of one or more groups independently selected from halogen, nitro, --NR.sub.4 R.sub.5, (lower)alkanoyl, (lower)alkyl or halo(lower)alkyl;
- Y is substituted or unsubstituted imidazolyl or 1,2,4-triazolyl, said substituents being one or more groups selected independently from (lower) alkyl, substituted and unsubstituted phenyl or substituted and unsubstituted phenyl(lower)alkyl, said substituents being as described hereinabove;
- R.sub.1 and R.sub.2 are independently hydrogen, --CH.sub.2 NR.sub.4 R.sub.5, --NR.sub.4 R.sub.5, --OR.sub.4, --SR.sub.5, (lower)alkyl, (lower)alkenyl, halogen, substituted or unsubstituted phenyl or phenyl(lower)alkyl, said phenyl and phenyl(lower)alkyl substituents being as described hereinabove, or R.sub.1 or R.sub.2 taken together with the carbon in the 3 position form carbonyl, thiocarbonyl, >C.dbd.N--R.sub.4, ##STR14## and R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are independently hydrogen, (lower)alkyl, substituted or unsubstituted phenyl or phenyl(lower)alkyl, said phenyl or phenyl(lower)alkyl substituents being as described hereinabove, or substituted or unsubstituted five or six membered heterocyclyl ring systems containing carbon and one to four heterto atoms chosen from N, O and S, said heterocyclyl substituents being halogen, lower(alkyl), (lower)alkanoyl, substituted and unsubstituted phenyl or substituted and unsubstituted phenyl(lower alkyl), said phenyl and phenyl(lower)alkyl substituents being asd described hereinabove;
- R.sub.4 and R.sub.5 are independently hydrogen, lower(alkyl), (lower)alkenyl, N,N-di(lower)alkylcarbamoyl, N,N-di(lower)alkylthiocarbamoyl, substituted and unsubstituted phenylcarbonyl or substituted and unsubstituted phenyl(lower)alkylcarbonyl, substituted or unsubstituted phenyl and phenyl(lower)alkyl, said phenyl and phenyl(lower)alkyl substituents being as described hereinabove, or R.sub.4 and R.sub.5 taken together with the nitrogen atom in NR.sub.4 R.sub.5 and --CH.sub.2 --NR.sub.4 R.sub.5 form substituted or unsubstituted five or six membered heterocyclyl ring systems containing carbon and one to four heteroatoms chosen from N, O and S, said heterocyclyl substituents being as described hereinabove;
- Z is O, S or NR.sub.5 ;
- N=1 or 2;
- and
- m=1, 2, 3 or 4.
Dependencies are inferred from the claim text.