Substituted aromatic sulfonamides as antiglaucoma agents

A compound of structural formula:

• ##STR145## or a pharmaceutically acceptable salt thereof X is --S--,
• m is 1 or 2;
• n is 0, 1 or 2;
• Z is
• 1) hydrogen,
• 2) --OR.sup.4 wherein R.sup.4 is
• a) hydrogen, or
• b) C.sub.1-5 alkyl, either unsubstituted or substituted with
• i) --OH, or
• ii) --NR.sup.6 R.sup.7 wherein R.sup.6 and R.sup.7 are independently hydrogen, C.sub.1-3 alkyl, --CO--C.sub.1-3 alkyl,
• 3) .dbd.O, or
• 4) --NRR.sup.1 ;
• R is hydrogen or R.sup.1 ;
• R.sup.1 is
• 1) C.sub.2-7 alkenyl,
• 2) C.sub.2-7 alkynyl, or
• 3) C.sub.1-6 alkyl, straight, branched or cyclic, either unsubstituted or substituted with 1, 2 or 3 substituents wherein the substituents are independently:
• a) halogen;
• b) hydroxy;
• c) C.sub.1-3 alkoxy;
• d) --NR.sup.6 R.sup.7 ;
• ##STR146## f) --CN;
• R.sup.2 is hydrogen or C.sub.1-5 alkyl;
• R.sup.3 is
• 1) --C.sub.1-5 alkyl substituted with one or more of
• a) hydroxy,
• b) --NR.sup.8 R.sup.9, wherein R.sup.8 is
• i) hydrogen, or
• ii) C.sub.1-3 alkyl;
• and
• R.sup.9 is
• i) C.sub.1-3 alkoxy-C.sub.1-3 alkyl,
• ii) hydroxy-C.sub.1-3 alkyl,
• iii) benzyl either unsubstituted or substituted on the phenyl group with up to three of halo, hydroxy, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, --CH.sub.2 NR.sup.10 R.sup.11 or --NR.sup.10 R.sup.11 wherein R.sup.10 and R.sup.11 are independently hydrogen, C.sub.1-3 alkyl, or C.sub.1-3 alkoxy-C.sub.1-3 alkyl, or
• iv) --CO--C.sub.1-6 alkyl;
• c) C.sub.1-5 alkoxy, either unsubstituted or substituted with one or more of:
• i) hydroxy,
• ii) C.sub.1-3 alkoxy,
• iii) NR.sup.10 R.sup.11,
• iv) --CN,
• v) phenyl, either unsubstituted or substituted with one or more of
• A) hydroxy,
• B) C.sub.1-3 alkoxy,
• C) C.sub.1-5 alkyl-NR.sup.10 R.sup.11, or
• D) halo,
• d) --SH,
• e) --CN, ##STR147## g) phenyl, either unsubstituted or substituted with up to three of i) hydroxy,
• ii) C.sub.1-3 alkoxy, or
• iii) C.sub.1-5 alkyl-NR.sup.10 R.sup.11,
• h) COR.sup.14 wherein R.sup.14 is
• i) hydroxy,
• ii) --NH.sub.2, or
• iii) C.sub.1-5 alkoxy, or
• iv) --NR.sup.12 R.sup.13 or
• i) C.sub.2-5 alkenyloxy;
• and ##STR148##