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Griseolic acid derivatives, and their use as enzyme inhibitors

  • US 4,634,706 A
  • Filed: 10/25/1984
  • Issued: 01/06/1987
  • Est. Priority Date: 10/28/1983
  • Status: Expired due to Fees
First Claim
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1. A griseolic acid compound of the formula:

  • ##STR9## wherein;

    A represents a group of formula;

    ##STR10## R1, R2, R5 and R6 are the same or different and each represents a hydrogen or halogen atom, the azido group, or a group of formula --OR9, --NR10 R11 or --SR9 ;

    R3 represents a hydrogen or halogen atom or a C1 -C20 aliphatic acyloxy or a (C6 -C20 aromatic)acyloxy or C1 -C6 alkoxy group;

    R4 represents a hydrogen or halogen atom;

    orR3 and R4 together represent an extra carbon-carbon bond between the carbon atoms to which they are attached;

    orR3 and R2 together represent an oxygen atom bridging the carbon atoms to which they are attached;

    R7 represents an optionally substituted C1 -C6 alkyl, C3 -C6 alkenyl or aralkyl group (wherein the alkyl moiety has from 1 to 6 carbon atoms), the substituents being selected from halogen atoms, C1 -C4 alkoxy groups, (C1 -C4 alkoxy)carbonyl groups and (where R7 is substituted aralkyl) C1 -C4 alkyl groups;

    R8 represents an oxygen or sulfur atom or the imino group;

    R9 represents hydrogen, a C1 -C6 alkyl group, a heterocyclic group (having 5 or 6 ring atoms, of which from 1 to 3 are oxygen, nitrogen or sulfur, and being unsubstituted or having from 1 to 3 C1 -C4 alkyl or alkoxy substituents), a tri(C1 -C4 alkyl)silyl group, an alkylsulfonyl group, a haloalkylsulfonyl group, a benzenesulphonyl optionally substituted with a C1 -C3 alkyl group, a C1 -C20 aliphatic acyl group or a C6 -C20 aromatic acyl group;

    R10 and R11 are the same or different and each represents hydrogen, hydroxy, a C1 -C6 alkyl group, a C1 -C6 hydroxyalkyl group, a C1 -C6 aminoalkyl group, an aralkyl group, an aryl group, a C1 -C6 alkoxy group, the amino group, a C1 -C20 aliphatic acyl group or a C6 -C20 aromatic acyl group;

    or R10 and R11, together with the nitrogen atom to which they are attached, represent a 5- or 6-membered heterocyclic group having at least one other hetero-atom selected from oxygen, and nitrogen atoms and optionally having one C1 -C4 alkyl substituent;

    and pharmaceutically acceptable salts and esters thereof;

    but excluding 7'"'"'(R)-griseolic acid itself and salts thereof.

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