Pyranoindazoles and their use for the treatment of glaucoma

A compound represented by Formula I:

• 17
• wherein R1 and R2 are independently chosen from hydrogen or an alkyl group;
• R3 and R4 are independently hydrogen or an alkyl group or;
• R3 and R4 and the carbon atom to which they are attached form a cycloalkyl ring, or;
• R2 and R3 together form a saturated (CH2)m heterocycle;
• R5 is hydrogen, halogen, or a substituted or unsubstituted alkyl group;
• R6 and R7 are independently hydrogen, halogen, cyano, an alkylthio, or a substituted or unsubstituted alkyl group;
• R8 and R9 are independently hydrogen, hydroxyl, an alkyl group, an alkoxy, ═O, NR10R11, OC(═O)NR1R2, OC(O)C1-4alkyl, an alkylthiol, or an alkyl substituted with halogen, NR10R11, OR12, CO2R13, or CONR14R15, or R8 and R9 can be chosen from Z(CH2)m—NR10R11, Z(CH2)m—OR12, Z-(CH2)p—C(═O)OR13, or Z-(CH2)p—C(O)NR14R15;
• R10 and R11 are independently hydrogen, a substituted or unsubstituted alkyl group, C(═O)C4 alkyl, C(═O)OC1-4alkyl, or C(═O)NR1R2 or R10 and R11 together complete a saturated 5 or 6-membered heterocyclic ring, which optionally includes an additional heteroatom selected from N, O, or S when a 6-membered ring;
• R12 is hydrogen, C1-6alkyl, C(═O)C1-6alkyl, or C(═O)C1-6alkyl substituted with hydroxyl, C1-4alkoxide, or halide;
• R13 is hydrogen, C1-6alkyl, C1-6alkyl substituted with hydroxyl, C1-4alkoxy, or halide;
• R14 and R15 are independently chosen from hydrogen, hydroxyl, C1-4alkoxy, C1-6alkyl, C2-6alkyl substituted by hydroxyl, C1-4alkoxy, halide, or R14 and R15 can be combined to forma saturated heterocyclic ring selected from pyrrolidine, piperidine, piperazine, or morpholine;
• A is (CH2)n, C═O, or CHC1-4alkyl;
• B is either a single or a double bond, wherein when B is a double bond, R8 and R9 are selected from hydrogen, or a substituted or unsubstituted alkyl group;
• wherein when A is (CH2)n and n is 0, R8 is chosen from CO2R13, C1-6alkyl substituted with OR12, NR10R11, CO2R13 or CONR14R15 and R9 is selected from hydrogen or C1-2alkyl and B is a single bond;
• Z is O or S(O)n;
• m=2-4;
• n=0-2;
• p=1-2;
• X and Y are either N or C, wherein X and Y are different;
• and the dashed bonds denote a suitably appointed single and double bond;
• Or pharmaceutically acceptable salts, solvates or prodrugs thereof.