Method for treating glaucoma VI

A method of decreasing intraocular pressure in an animal, including a human, comprising administering an intraocular pressure decreasing amount of a compound of the formula I:

• wherein:
• a. W and Y are independently N or, respectively, CRW or CRY;
• b. Z is O, S or NRZ;
• c. Q is —CH2— or —(CO)—CH2—, where the methylene is bonded to a ring nitrogen;
• d. RW and RY are independently hydrogen, alkyl, —C≡CRE, —CH2—C≡CRP, alkenyl, aryl, arylalkyl, aryloxy, arylthio, amino, alkylamino, arylamino, dialkylamino, diarylamino, CH3C(O)NH—, fluoroalkyl, perfluoroaryl, hydroxyalkyl, C(O)NH2, and S(O)2NH2 or, together with their ring carbon atoms form a fused 6-membered aromatic or heteroaromatic ring, wherein RE or RP is alkyl, hydrogen, hydroxyalkyl or aryl;
• e. RZ is alkyl, —CH2—C≡CRP, aryl, arylalkyl, or aroylalkyl;
• f. R1 and R2 are independently hydrogen, alkyl or hydroxymethyl;
• g. R3 is hydrogen or methyl;
• h. R1 is acetamido, hydrogen, methyl, amino, —C≡CRE, —CH2—C≡CRP alkylthio, fluoromethyl, difluoromethyl, trifluoromethyl, cyanomethyl, hydroxyalkyl, alkoxycarbonyl-methyl, 1-(alkoxycarbonyl)-1-hydroxyalkyl or aminocarbonylmethyl;
• i. Ar, or aryl, refers to a C6 or C10 aromatic ring, optionally substituted as set forth below, or a 5- or 6-membered heteroaromatic (heteroaryl) ring containing at least one and up to three atoms of N for the 6-membered heteroaryl ring and from one to three atoms of N or one atom of O or S and zero to two atoms of N for the 5-membered heteroaryl ring;
• each heteroaromatic ring can be substituted with up to two amino-, dialkylamino-, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, thiamorpholin-4-yl, 4-(aryl)piperidin-1-yl, 4-(aryl)piperazin-1-yl-(said aryl group optionally substituted as described below), halo (particularly fluoro) or alkylenedioxy groups, or fused to a substituted benzene, pyridine, pyrimidine, pyridazine or triazine ring, and wherein C6 or C10 aromatic and heteroaromatic rings can be additionally substituted;
• j. C6 or C10 aromatic rings can be additionally substituted with acylamino, acyloxyalkyl, alkanoyl, alkanoylalkyl, alkenyl, alkoxy, alkoxycarbonyl, alkoxycarbonylalkyl, alkyl, alkylamino, (C1-C3)-alkylenedioxy, alkylsulfonyl, alkylthio, allyl, amino, benzoyl, carboxy, carboxyalkyl, cyano, cycloalkyl, dialkylamino, halo, fluoromethyl, difluoromethyl, trifluoromethyl, hydroxy, (C1-C6)-hydroxyalkyl, mercapto, nitro, phenoxy, phenyl, phenylalkyl, sulfamoyl, sulfo (—SO3H), aminosulfonyl (H2NSO2—), phenylsulfonyl, or phenylsulfinyl;
• k. heteroaromatic rings can be additionally substituted with acylamino, alkanoyl, alkoxy, alkoxycarbonyl, alkoxycarbonylalkyl, alkyl, alkylamino, alkylsulfonyl, alkylthio, amino, arylsulfonyl, aryl sulfonyl, benzoyl, carboxy, cyano, dialkylamino, halo, fluoralkyl, hydroxy, mercapto, nitro, phenyl, phenoxy, pyrrolidin-1-yl, piperidin-1-yl, 4-arylpiperidin-1-yl, morpholin-4-yl, 4-arylpiperazin-1-yl, sulfamoyl, fluoromethyl, difluoromethyl, or trifluoromethyl;
• l. the halo atoms can be fluoro, chloro, bromo or iodo;
• and
• m. X− is a pharmaceutically acceptable anion;
• and pharmaceutically acceptable acid addition salts of said compounds.