1,3,4-thiadiazoles useful for the treatment of CMV infections

A compound of formula I ##STR16## or pharmaceutically acceptable salts thereof wherein:

• Y is
• a) --NHR.sub.1, or ##STR17## X is a) --O--,
• b) --S(.dbd.O).sub.h --,
• c) --CH.sub.2 --, or
• d) --NR.sub.2 --;
• R.sub.1 is
• a) C.sub.4-12 alkyl,
• b) --(CH.sub.2).sub.i -C.sub.3-7 cycloalkyl,
• c) 6,6-dimethylbicyclo[3.1.1]-2-heptyl,
• d) --(CH.sub.2).sub.j -M,
• e) --(CH.sub.2).sub.j -W,
• f) --(CH.sub.2).sub.k aryl, wherein aryl may be substituted with one to three R.sub.3,
• g) --(CH.sub.2).sub.k -het, wherein het may be substituted with one to three R.sub.3, or
• h) --(CH.sub.2).sub.k -Q, wherein Q may be substituted with one to three R.sub.3 ;
• R.sub.2 is
• a) H,
• b) C.sub.1-4 alkyl,
• c) --C(.dbd.O)C.sub.1-4 alkyl,
• d) --S(.dbd.O)C.sub.1-4 alkyl,
• e) --CO.sub.2 C.sub.1-4 alkyl, or
• f) --CO.sub.2 CH.sub.2 phenyl;
• R.sub.3 is
• a) halo,
• b) C.sub.1-4 alkyl,
• c) C.sub.1-4 alkoxy,
• d) benzyl,
• e) --CN,
• f) --SO.sub.2 F,
• g) --SO.sub.2 NH.sub.2,
• h) --CF.sub.3,
• i) --NO.sub.2,
• j) --OCH.sub.2 O--,
• k) --CO.sub.2 (C.sub.1-4 alkyl),
• l) --C(.dbd.O)C.sub.1-4 alkyl,
• m) --C(.dbd.O)NH.sub.2,
• n) --NHCO.sub.2 (C.sub.1-4 alkyl), or
• o) --C(.dbd.O)--O--C(.dbd.O)--;
• M is
• a) --CN,
• b) halo,
• c) --CO.sub.2 C.sub.1-4 alkyl,
• d) --CH(phenyl).sub.2, ##STR18## W is a) --OR.sub.4,
• b) --SR.sub.4,
• c) --NHR.sub.5, or
• d) --NR.sub.6 R.sub.7 ;
• R.sub.4 is
• a) C.sub.1-4 alkyl,
• b) C.sub.3-7 cycloalkyl, or
• c) aryl;
• R.sub.5 is
• a) C.sub.1-4 alkyl,
• b) C.sub.3-7 cycloalkyl,
• c) aryl, or
• d) --C(.dbd.O)C.sub.1-4 alkyl;
• R.sub.6 and R.sub.7 are independently
• a) C.sub.1-4 alkyl, or
• b) R.sub.6 and R.sub.7 together with nitrogen form azetidinyl, pyrrolidinyl, piperdinyl, piperazinyl, 4-methyl-1-piperazinyl, hydantoin, 4-morpholinyl, thiomorpholinyl, or 2-oxo-1-pyrrolidinyl;
• R.sub.1 is
• a) C.sub.1-18 alkyl,
• b) C.sub.2-18 alkenyl,
• c) C.sub.2-18 alkynyl,
• d) C.sub.2-6 alkyl substituted with one to three halo, C.sub.1-3 alkoxy, --OH, --SH, or --CO.sub.2 H,
• e) C.sub.2-6 alkenyl substituted with aryl, wherein the aryl may be in turn substituted with one to three R.sub.2,
• f) --(CH.sub.2).sub.i aryl, wherein aryl may be substituted with one to three R.sub.3,
• g) --(CH.sub.2).sub.i -Q, wherein Q may be substituted with one to three R.sub.3, or
• h) --(CH.sub.2).sub.i -U, wherein U may be substituted with one to three R.sub.3 ;
• aryl is phenyl or naphthyl;
• het is
• a) furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
• b) pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyranyl,
• c) indazolyl, benzothiazolyl, benzoimidazolyl, benzofuryl, isobenzofuryl, benzothiazole, benzoisoxazole, benzothienyl, indolyl, isoindolyl, or
• d) quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl or cinnolinyl;
• U is
• a) furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
• b) pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyranyl, or
• c) indazolyl, benzothiazolyl, benzoimidazolyl, benzofuryl, isobenzofuryl, benzothiazole, benzoisoxazole, benzothienyl, indolyl, isoindolyl;
• Q is
• a) 2-, 3-, or 4-piperidinyl,
• b) 1-, or 2-pyrrolidinyl,
• wherein the nitrogen atom in a) and b) may be substituted with C.sub.1-4 alkyl, phenyl, benzyl, or --C(.dbd.O)C.sub.1-4 alkyl,
• c) morpholinyl,
• d) thiomorpholinyl,
• e) dioxolanyl,
• f) imidazolidinyl,
• g) oxathiolanyl,
• h) oxazolidinyl,
• i) tetrahydrofuryl, or
• j) 2-oxo-1-pyrrolidinyl.
• h is 0, 1, or 2;
• i is 0, 1, 2, 3, or 4;
• j is 2, 3, or 4;
• k is 0, 1, 2, 3, 4, 5, or 6;
• and with the following provisos:
• a) where R.sub.3 is phenyl or 4-methoxyphenyl, R.sub.1 is other than phenyl, 4-methoxyphenyl, or 4-chlorophenyl;
• b) where R.sub.3 is --CH.sub.2 phenyl, R.sub.1 is other than phenyl or --CH.sub.2 phenyl;
• c) where R.sub.3 is H, substituted or unsubstituted alkyl or phenyl, R.sub.1 is other than unsubstituted alkyl or phenyl.