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Guanidino compounds as regulators of nitric oxide synthase

  • US 5,478,946 A
  • Filed: 11/30/1993
  • Issued: 12/26/1995
  • Est. Priority Date: 06/21/1989
  • Status: Expired due to Fees
First Claim
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1. A compound of the formula:

  • ##STR9## or a pharmaceutically-acceptable salt, ester, amide or prodrug thereof, wherein;

    R1 is selected from the group consisting of;

    (1) hydrogen;

    (2) C1 -C6 -alkyl;

    (3) C6 -C12 -aryl-C1 -C4 -alkyl;

    (4) substituted C6 -C12 -aryl-C1 -C4 -alkyl;

    (5) N-protecting group;

    (6) --CO--C1 -C6 -alkyl;

    (7) --CO--C6 -C12 -aryl;

    (8) --CO--substituted C6 -C12 -aryl;

    (9) --CO--(C6 -C12 -aryl-C1 -C4 -alkyl);

    (10) --CO--(substituted C6 -C12 -aryl-C1 -C4 -alkyl); and

    (11) --CO-Het;

    R2 is selected from the group consisting of;

    (1) hydrogen;

    (2) C1 -C6 -alkyl;

    (3) C6 -C12 -aryl-C1 -C4 -alkyl; and

    (4) substituted C6 -C12 -aryl-C1 -C4 -alkyl;

    R3 is selected from the group consisting of;

    (1) hydrogen;

    (2) C1 -C6 -alkyl;

    (3) C2 -C6 -alkenyl;

    (4) cyclo-C3 -C7 -alkyl;

    (5) C6 -C12 -aryl; and

    (6) substituted C6 -C12 -aryl;

    R4 is selected from the group consisting of;

    (1) hydroxy;

    (2) C1 -C6 -alkoxy;

    (3) C6 -C12 -aryloxy;

    (4) substituted C6 -C12 -aryloxy;

    (5) --O--(C1 -C6 -alkyl-C6 -C12 -aryl);

    (6) --O--(substituted C6 -C12 -aryl-C1 -C4 -alkyl); and

    (7) --NHR11, wherein R11 is hydrogen or C1 -C4 -alkyl;

    orR2 and R4 are linked together by a single bond to form a nitrogen-containing ring of the formula;

    ##STR10## wherein R1 and R3 are as defined above, R4 is O and R2 is --CR9 R10,wherein R9 is selected from the group consisting of;

    (1) hydrogen;

    (2) C1 -C6 -alkyl;

    (3) substituted C1 -C6 -alkyl;

    (4) C6 -C12 -aryl;

    (5) substituted C6 -C12 -aryl;

    (6) C2 -C6 -alkenyl;

    (7) carboxy;

    (8) C1 -C4 -alkoxycarbonyl, as defined below;

    (9) carboxamido; and

    (10) cyano;

    R10 is hydrogen or C1 -C6 -alkyl; and

    R12 is hydrogen or C1 -C 4 -alkyl;

    R5 and R6 are independently selected from the group consisting of;

    (1) hydrogen;

    (2) C1 -C4 -alkyl;

    (3) C6 -C12 -aryl-C1 -C6 -alkyl;

    (4) substituted C6 -C12 -aryl-C1 -C6 -alkyl;

    (5) halo-C1 -C2 -alkyl; and

    (6) halogen;

    R7 is selected from the group consisting of;

    (1) hydrogen;

    (2) C1 -C3 -alkyl;

    (3) cyano;

    (4) nitro;

    (5) hydroxy;

    (6) amino; and

    (7) --OR15, wherein R15 is a hydroxy-protecting group;

    R8 is hydrogen or C1 -C4 -alkyl; and

    * may be a chiral center.

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