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Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma

  • US 6,989,445 B2
  • Filed: 12/14/2004
  • Issued: 01/24/2006
  • Est. Priority Date: 12/15/2003
  • Status: Expired due to Fees
First Claim
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1. A compound of the formula embedded imagewhereinR1 and R2 are independently hydrogen or C1-4alkyl;

  • R3 is hydrogen or C1-4alkyl, or R2 and R3 together can complete a pyrrolidine or piperidine ring, which can be substituted with C1-4alkyl;

    R4 is hydrogen, halogen, or C1-4alkyl;

    R5 and R6 are independently hydrogen, halogen, C1-6alkyl, C1-6alkylthio, C1-6alkylsulfonyl, C1-6alkylsulfoxide, nitrile, or C1-6alkyl substituted with halogen;

    R7 is hydrogen, C═

    OR9, ═

    O, C1-6alkyl, or substituted C1-6alkyl wherein the substituent is at least one of hydroxyl, C1-6alkoxy, NR12R13, CO2H, CO2C1-6alkyl, C(═

    O)NR12R13, S(O)mNR12R13, and a saturated or unsaturated 5 or 6-membered heteroaryl ring which can contain 1–

    4 heteroatoms selected from N, O, or S and can be unsubstituted or substituted with C1-4alkyl or phenyl;

    R8 is hydrogen, C1-6alkyl, or substituted C1-6alkyl wherein the substituent is at least one of hydroxyl, C1-6alkoxy, NR12R13, CO2H, CO2C1-6alkyl and C(═

    O)NR12R13;

    R9 is hydroxyl, C1-6alkoxy, NR14R15, C1-6alkyl, or substituted C2-6 alkyl wherein the substituent is at least one of hydroxyl, C1-6alkoxy, NR12R13, CO2H, CO2C1-6alkyl, S(O)mNR12R13, halogen, and a heterocyclic ring selected from pyrrolidin-2-yl, imidazo-2-yl, imidazo-4-yl, morpholin-3-yl, oxazolyl, isoxazolyl, thiazolyl, or tetrazolyl, which can be unsubstituted or substituted with C1-4alkyl;

    R12 and R13 are independently hydrogen, C1-6alkyl, or substituted C2-6alkyl wherein the substituent is at least one of hydroxyl, C1-6alkoxy, and halogen, or R12, R13, and the intervening nitrogen atom together can form a heterocyclic ring selected from morpholine, thiomorpholine, thiomorpholine 1-oxide, thiomorpholine 1,1-dioxide, azetidine, pyrrolidine, piperidine, piperazine, unsubstituted or substituted with C1-4alkyl, or C1-4alkyl substituted with hydroxy or C1-4alkoxy;

    R14 and R15 are independently hydrogen, C1-6alkyl, hydroxyl, C1-6alkoxy, or substituted C2-6alkyl wherein the substituent is at least one of hydroxyl, C1-6alkoxy, halogen and a heterocyclic ring selected from pyrrolidin-2-yl, imidazo-2-yl, imidazo-4-yl, morpholin-3-yl, oxazolyl, isoxazolyl, thiazolyl, tetrazolyl, which can be unsubstituted or substituted with C1-4alkyl, or R14, R15, and the intervening nitrogen atom together can form a heterocyclic ring selected from morpholine, thiomorpholine, thiomorpholine 1-oxide, thiomorpholine 1,1-dioxide, azetidine, pyrrolidine, piperidine, piperazine, unsubstituted or substituted with C1-4alkyl or C1-4alkyl substituted with hydroxy or C1-4alkoxy;

    A is N or CH;

    X and Y are either N or C, provided that X and Y cannot be the same;

    and the dashed bonds denote a single or double bond.

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