Phenalenone derivatives, processes for preparation and use thereof
AssigneeSanofi-Aventis Deutschland GmbH
InventorsLaszlo Vertesy, Michael Kurz, Ziyu Li, Luigi Toti
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Abstract
The present invention provides novel phenalenone derivatives of formula (I) which are formed by the microorganism Penicillium herquei Bainer & Sartory, DSM 14142, during fermentation. A process for their preparation, their use as pharmaceutical compositions, and their use for the treatment or prophylaxis of bacterial infections, mycoses, oncoses and rheumatic diseases are also disclosed and claimed
Claims15
A compound of formula (I-A) or of formula (I-B),
- wherein:
- X is a group of formula (I-C) or of formula (I-D),
- wherein:
- R1 and, if present, R2 simultaneously are H, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, wherein said C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl substituents are optionally mono- or disubstituted by —OH, ═O, —O—C1-C6-alkyl, —O—C2-C6-alkenyl, —C6-C10-aryl, —NH—C1-C6-alkyl, —NH—C2-C6-alkenyl, —NH2, or halogen,
- wherein said —O—C1—C6—alkyl, —O—C2—C6—alkenyl, —C6—C10—aryl, —NH—C1—C6—alkyl,
- and —NH—C2—C2—C6—alkenyl substituents are optionally substituted by —CN, —NH—C(O)—(C1—C6—alkyl) or =NOH, or
- a stereoisomeric form of the compound of formula (I-A) or (I-B), or mixtures of the steroisomeric forms thereof in any ratio, or
- a pharmaceutically acceptable salt thereof, and
- with the proviso that when R1 is H, X is the group of formula (I-C) and
- with the proviso that both R1 and R2 are not simultaneously H.
A method for the treatment or prophylaxis of bacterial infections comprising administering to a patient in need of said treatment or prophylaxis an antibacterially effective amount of a compound of formula (I-A) or of formula (I-B),
- wherein:
- X is a group of formula (I-C) or of formula (I-D),
- wherein:
- R1 and, if present, R2 simultaneously are H, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, wherein said C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl substituents are optionally mono- or disubstituted by —OH, ═O, —O—C1-C6-alkyl, —O-C2-C6-alkenyl, —C6-C10-aryl, —NH—C1-C6-alkyl, —NH—C2-C6-alkenyl, —NH2, or halogen,
- wherein said —O—C1-C6-alkyl, —O—C2-C6-alkenyl, —C6-C10-aryl, —NH—C1-C6-alkyl, and —NH—C2-C6-alkenyl substituents are optionally substituted by —CN, —NH—C(O)—(C1-C6-alkyl) or ═NOH, or
- a stereoisomeric form of the compound of formula (I-A) or (I-B), or mixtures of the stereoisomeric forms thereof in any ratio, or
- a pharmaceutically acceptable salt thereof, and
- with the proviso that when R1 is H, X is the group of formula (I-C).
A method for the treatment or prophylaxis of mycoses comprising administering to a patient in need of said treatment or prophylaxis an antimycotically effective amount of a compound of formula (I-A) or of formula (I-B),
- wherein:
- X is a group of formula (I-C) or of formula (I-D),
- wherein:
- R1 and, if present, R2 simultaneously are H, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, wherein said C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl substituents are optionally mono- or disubstituted by —OH, ═O, —O—C1-C6-alkyl, —O—C2-C6-alkenyl, —C6-C10-aryl, —NH—C1-C6-alkyl, —NH—C2-C6-alkenyl, —NH2, or halogen,
- wherein said —O—C1-C6-alkyl, —O—C2-C6-alkenyl, —C6-C10-aryl, —NH—C1-C6-alkyl, and —NH—C2-C6-alkenyl substituents are optionally substituted by —CN, —NH—C(O)—(C1-C6-alkyl) or ═NOH, or
- a stereoisomeric form of the compound of formula (I-A) or (I-B), or mixtures of the stereoisomeric forms thereof in any ratio, or
- a pharmaceutically acceptable salt thereof, and
- with the proviso that when R1 is H, X is the group of formula (I-C).
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and an effective amount of the compound of formula (I-A) or of formula (I-B),
- wherein:
- X is a group of formula (I-C) or of formula (I-D),
- wherein:
- R1 and, if present, R2 simultaneously are H, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, wherein said C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl substituents are optionally mono- or disubstituted by −OH, ═O, —O—C1-C6-alkyl, —O—C2-C6-alkenyl, —C6-C10-aryl, —NH-C1-C6-alkyl, —NH—C2-C6-alkenyl, —NH2, or halogen,
- wherein said —O—C1-C6-alkyl, —O—C2-C6-alkenyl, —C6-C10-aryl, —NH—C1-C6-alkyl, and —NH—C2-C6-alkenyl substituents are optionally substituted by —CN, —NH—C(O)—(C1-C6-alkyl) or ═NOH, or
- a stereoisomeric form of the compound of formula (I-A) or (I-B), or mixtures of the stereoisomeric forms thereof in any ratio, or
- a pharmaceutically acceptable salt thereof, and
- with the proviso that when R1 is H, X is the group of formula (I-C).
A compound isolated from the strain, Penicillium herquei Bainer & Sartory, DSM 14142, said compound having the formula (II-A) or (II-B):
Dependencies are inferred from the claim text.