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US 6,486,148 B2Granted
Steroid derived antibiotics
AssigneeBrigham Young University
InventorsPaul B. Savage, Chunhong Li
Life of this patent
Estimating the term…
Abstract
A series of novel steroid derivatives are described. The steroid derivatives are antibacterial agents. The steroid derivatives also act to sensitize bacteria to other antibiotics including erythromycin and novobiocin.
Claims10
A method of treating a microbial infection of a host by administering to the host an effective amount of an anti-microbial composition comprising a compound according to formula I:
- wherein:
- fused rings A, B, C, and D are independently saturated or fully or partially unsaturated;
- and
- R1 through R4, R6, R7, R11, R12, R15, R16, and R17 is each independently selected from the group consisting of hydrogen, hydroxyl, a substituted or unsubstituted (C1-C10) alkyl, (C1-C10) hydroxyalkyl, (C1-C10) alkyloxy-(C1-C10) alkyl, (C1-C10) alkylamino-(C1-C10) alkyl, a substituted or unsubstituted (C1-C10) aminoalkyl, a substituted or unsubstituted aryl, C1-C10 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, oxo, a linking group attached to a second steroid, a substituted or unsubstituted (C1-C10) aminoalkyloxy, a substituted or unsubstituted (C1-C10) aminoalkylcarboxy, a substituted or unsubstituted (C1-C10) aminoalkylaminocarbonyl, a substituted or unsubstituted (C1-C10) aminoalkylcarboxamido, H2N-HC(Q5)-C(O)-O—, H2N-HC(Q5)-C(O)-N(H)—, (C1-C10) azidoalkyloxy, (C1-C10) cyanoalkyloxy, P.G.-HN-CH(Q5)-C(O)-O—, (C1-C10) guanidinoalkyloxy, and (C1-C10) guanidinoalkyl carboxy, where Q5 is a side chain of any amino acid, P.G. is an amino protecting group, and
- R5, R8, R9, R10, R13, and R14 is each independently:
- deleted when one of fused rings A, B, C, or D is unsaturated so as to complete the valency of the carbon atom at that site, or
- selected from the group consisting of hydrogen, hydroxyl, a substituted or unsubstituted (C1-C10) alkyl, (C1-C10) hydroxyalkyl, (C1-C10) alkyloxy-(C1-C10) alkyl, a substituted or unsubstituted (C1-C10) aminoalkyl, a substituted or unsubstituted aryl, C1-C10 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, oxo, a linking group attached to a second steroid, a substituted or unsubstituted (C1-C10) aminoalkyloxy, a substituted or unsubstituted (C1-C10) aminoalkylcarboxy, a substituted or unsubstituted (C1-C10) aminoalkylaminocarbonyl, H2N- HC(Q5)-C(O) O—, H2N- C(Q5)-C(O)-N(H)—, (C1-C10) azidoalkyloxy, (C1-C10) cyanoalkyloxy, P.G.-HN-CH(Q5)-C(O)—O—, (C1-C10) guanidinoalkyloxy, and (C1-C10) guanidinoalkylcarboxy, where Q5 is a side chain of any amino acid, P.G. is an amino protecting group, and
- provided that at least two of R1 through R14 are independently selected from the group consisting of a substituted or unsubstituted (C1-C10) aminoalkyloxy, a substituted or unsubstituted (C1-C10) aminoalkylcarboxy, a substituted or unsubstituted (C1-C10) aminoalkylaminocarbonyl, a substituted or unsubstituted (C1-C10) aminoalkylcarboxamido, H2N—HC(Q5)-C(O)-O—, H2N-HC(Q5)-C(O)-N(H)—, (C1-C10) azidoalkyloxy, (C1-C10) cyanoalkyloxy, P.G.-HN-CH(Q5)-C(O)-O—, (C1-C10) guanidinoalkyloxy, and (C1-C10) guanidinoalkylcarboxy;
- or a pharmaceutically acceptable salt thereof.
6 more elements
A method of microbial growth control comprising contacting a microbe with an effective amount of anti-microbial composition comprising a compound according to formula I:
- wherein:
- fused rings A, B, C, and D are independently saturated or fully or partially unsaturated;
- and
- R1 through R4, R6, R7, R11, R12, R15, R16, and R17 is each independently selected from the group consisting of hydrogen, hydroxyl, a substituted or unsubstituted (C1-C10) alkyl, (C1-C10) hydroxyalkyl, (C1-C10) alkyloxy-(C1-C10) alkyl, (C1-C10) alkylamino-(C1-C10) alkyl, a substituted or unsubstituted (C1-C10) aminoalkyl, a substituted or unsubstituted aryl, C1-C10 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, oxo, a linking group attached to a second steroid, a substituted or unsubstituted (C1-C10) aminoalkyloxy, a substituted or unsubstituted (C1-C10) aminoalkylcarboxy, a substituted or unsubstituted (C1-C10) aminoalkylaminocarbonyl, a substituted or unsubstituted (C1-C10) aminoalkylcarboxamido, H2N—HC(Q5)-C(O)-O—, H2N-HC(Q5)-C(O)-N(H)—, (C1-C10) azidoalkyloxy, (C1-C10) cyanoalkyloxy, P.G.-HN-CH(Q5)-C(O)-O—, (C1-C10) guanidinoalkyloxy, and (C1-C10) guanidinoalkyl carboxy, where Q5 is a side chain of any amino acid, P.G. is an amino protecting group, and
- R5, R8, R9, R10, R13, and R14 is each independently:
- deleted when one of fused rings A, B, C, or D is unsaturated so as to complete the valency of the carbon atom at that site, or
- selected from the group consisting of hydrogen, hydroxyl, a substituted or unsubstituted (C1-C10) alkyl, (C1-C10) hydroxyalkyl, (C1-C10) alkyloxy-(C1-C10) alkyl, a substituted or unsubstituted (C1-C10) aminoalkyl, a substituted or unsubstituted aryl, C1-C10 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, oxo, a linking group attached to a second steroid, a substituted or unsubstituted (C1-C10) aminoalkyloxy, a substituted or unsubstituted (C1-C10) aminoalkylcarboxy, a substituted or unsubstituted (C1-C10) aminoalkylaminocarbonyl, H2N-HC(Q5)-C(O)-O—, H2N-HC(Q5)-C(O)-N(H)—, (C1-C10) azidoalkyloxy, (C1-C10) cyanoalkyloxy, P.G.-HN-CH(Q5)-C(O)-O—, (C1-C10) guanidinoalkyloxy, and (C1-C10) guanidinoalkylcarboxy, where Q5 is a side chain of any amino acid, P.G. is an amino protecting group, and
- provided that at least two of R1 through R14 are independently selected from the group consisting of a substituted or unsubstituted (C1-C10) aminoalkyloxy, a substituted or unsubstituted (C1-C10) aminoalkylcarboxy, a substituted or unsubstituted (C1-C10) aminoalkylaminocarbonyl, a substituted or unsubstituted (C1-C10) aminoalkylcarboxamido, H2N-HC(Q5)-C(O)-O—, H2N-HC(Q5)-C(O)-N(H)—, (C1-C10) azidoalkyloxy, (C1-C10) cyanoalkyloxy, P.G.-HN-CH(Q5)-C(O)-O—, (C1-C10) guanidinoalkyloxy, and (C1-C10) guanidinoalkylcarboxy;
- or a pharmaceutically acceptable salt thereof.
6 more elements
Dependencies are inferred from the claim text.