Chromane-like cyclic prenylflavonoids for the medical intervention in neurological disorders
AssigneesLudwig Aigner, Sébastien Couillard-Despres
InventorsLudwig Aigner, Eleni Priglinger, Sébastien Couillard-Despres, Francisco Javier Rivera, Herbert Riepl, Corinna Urmann, Martin Biendl
Life of this patent
Estimating the term…
Abstract
The present invention relates to certain chromane-like cyclic prenylflavonoids, in particular the compounds of formulae (I), (II) and (III) as described and defined herein, for use in the treatment or prevention of a neurological disorder, as well as their use in promoting neuronal differentiation, neurite outgrowth and neuroprotection.
Claims17
A method of treating a neurological disorder selected from the group consisting of a spinal cord injury and a peripheral nerves injury, the method comprising the administration of a compound of the following formula (I) or a pharmaceutically acceptable salt or solvate of said compound to a subject in need of such a treatment,
- wherein:
- A is aryl or heteroaryl, wherein said aryl or said heteroaryl is optionally substituted with one or more groups independently selected from C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, —OH, —O(C1-6 alkyl), —SH, —S(C1-6 alkyl), —NH2, —NH(C1-6 alkyl), —N(C1-6 alkyl)(C1-6 alkyl), —O—CO—C1-6 alkyl, —O—CO-phenyl, —O—CO—(C1-6 alkylene)-phenyl, —O—CO—O(C1-6 alkyl), —CO—C1-6 alkyl, —COOH, —CO—O(C1-6 alkyl), —CO—NH2, —CO—NH—(C1-6 alkyl), —CO—N(C1-6 alkyl)(C1-6 alkyl), —O—CO—NH2, —O—CO—NH—(C1-6 alkyl), —O—CO—N(C1-6 alkyl)(C1-6 alkyl), —NH—CO—(C1-6 alkyl), —N(C1-6 alkyl)-CO—(C1-6 alkyl), —NH—CO—O(C1-6 alkyl), —N(C1-6 alkyl)-CO—O(C1-6 alkyl), —NH—CO—NH2, —N(C1-6 alkyl)-CO—NH2, —NH—CO—NH(C1-6 alkyl), —N(C1-6 alkyl)-CO—NH(C1-6 alkyl), —NH—CO—N(C1-6 alkyl)(C1-6 alkyl), —N(C1-6 alkyl)-CO—N(C1-6 alkyl)(C1-6 alkyl), halogen, —CF3, or —CN;
- R10 is —OH, —O(C1-6 alkyl), —SH, —S(C1-6 alkyl), —NH2, —NH(C1-6 alkyl), —N(C1-6 alkyl)(C1-6 alkyl), hydrogen, or C1-6 alkyl;
- R11 and R12 are each independently selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, —OH, —O(C1-6 alkyl), —SH, —S(C1-6 alkyl), —NH2, —NH(C1-6 alkyl), —N(C1-6 alkyl)(C1-6 alkyl), —O—CO—C1-6 alkyl, —O—CO-phenyl, —O—CO—(C1-6 alkylene)-phenyl, —O—CO—O(C1-6 alkyl), —CO—C1-6 alkyl, —CO—NH2, —CO—NH—(C1-6 alkyl), —CO—N(C1-6 alkyl)(C1-6 alkyl), —O—CO—NH2, —O—CO—NH—(C1-6 alkyl), —O—CO—N(C1-6 alkyl)(C1-6 alkyl), —NH—CO—(C1-6 alkyl), —N(C1-6 alkyl)-CO—(C1-6 alkyl), —NH—CO—O(C1-6 alkyl), —N(C1-6 alkyl)-CO—O(C1-6 alkyl), —NH—CO—NH2, —N(C1-6 alkyl)-CO—NH2, —NH—CO—NH(C1-6 alkyl), —N(C1-6 alkyl)-CO—NH(C1-6 alkyl), —NH—CO—N(C1-6 alkyl)(C1-6 alkyl), —N(C1-6 alkyl)-CO—N(C1-6 alkyl)(C1-6 alkyl), halogen, —CF3, or —CN;
- each R13 is independently selected from C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, —OH, —O(C1-6 alkyl), —SH, —S(C1-6 alkyl), —NH2, —NH(C1-6 alkyl), —N(C1-6 alkyl)(C1-6 alkyl), —O—CO—C1-6 alkyl, —O—CO-phenyl, —O—CO—(C1-6 alkylene)-phenyl, —O—CO—O(C1-6 alkyl), —CO—C1-6 alkyl, —CO—NH2, —CO—NH—(C1-6 alkyl), —CO—N(C1-6 alkyl)(C1-6 alkyl), —O—CO—NH2, —O—CO—NH—(C1-6 alkyl), —O—CO—N(C1-6 alkyl)(C1-6 alkyl), —NH—CO—(C1-6 alkyl), —N(C1-6 alkyl)-CO—(C1-6 alkyl), —NH—CO—O(C1-6 alkyl), —N(C1-6 alkyl)-CO—O(C1-6 alkyl), —NH—CO—NH2, —N(C1-6 alkyl)-CO—NH2, —NH—CO—NH(C1-6 alkyl), —N(C1-6 alkyl)-CO—NH(C1-6 alkyl), —NH—CO—N(C1-6 alkyl)(C1-6 alkyl), —N(C1-6 alkyl)-CO—N(C1-6 alkyl)(C1-6 alkyl), halogen, —CF3, or —CN;
- R14 and R15 are each independently selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, —OH, —O(C1-6 alkyl), —SH, —S(C1-6 alkyl), —NH2, —NH(C1-6 alkyl), —N(C1-6 alkyl)(C1-6 alkyl), —O—CO—C1-6 alkyl, —O—CO-phenyl, —O—CO—(C1-6 alkylene)-phenyl, —O—CO—O(C1-6 alkyl), —CO—C1-6 alkyl, —CO—NH2, —CO—NH—(C1-6 alkyl), —CO—N(C1-6 alkyl)(C1-6 alkyl), —O—CO—NH2, —O—CO—NH—(C1-6 alkyl), —O—CO—N(C1-6 alkyl)(C1-6 alkyl), —NH—CO—(C1-6 alkyl), —N(C1-6 alkyl)-CO—(C1-6 alkyl), —NH—CO—O(C1-6 alkyl), —N(C1-6 alkyl)-CO—O(C1-6 alkyl), —NH—CO—NH2, —N(C1-6 alkyl)-CO—NH2, —NH—CO—NH(C1-6 alkyl), —N(C1-6 alkyl)-CO—NH(C1-6 alkyl), —NH—CO—N(C1-6 alkyl)(C1-6 alkyl), —N(C1-6 alkyl)-CO—N(C1-6 alkyl)(C1-6 alkyl), halogen, —CF3, or —CN;
- R16 is O, S or N(—OH);
- n is 0, 1, 2 or 3;
- and
- each in formula (I) is independently a single bond or a double bond, provided that at least one of the two adjacent bonds is a single bond.
Dependencies are inferred from the claim text.