Chromane-like cyclic prenylflavonoids for the medical intervention in neurological disorders

A method of treating or preventing a neurological disorder, the method comprising the administration of a compound of one of the following formulae (I), (II) or (III) or a pharmaceutically acceptable salt or solvate thereof to a subject in need of such a treatment or prevention,

• 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, —COON, —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;
• 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;
• B 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, —COON, —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;
• X is selected from O, S, N(H), N(C1-6 alkyl), or C(═N—OH);
• R21 and R22 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 R23 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;
• R24 is 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;
• R25 is O, S or N(—OH);
• m is 0, 1, 2 or 3;
• each in formula (II) is independently a single bond or a double bond, provided that at least one of the two adjacent bonds is a single bond;
• C 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, —COON, —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;
• Y is selected from O, S, N(H), N(C1-6 alkyl), or C(═N—OH);
• R31 is 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;
• R32 is 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 R33 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;
• R34 is O, S or N(—OH);
• p is 0, 1, 2 or 3;
• and
• each in formula (III) is independently a single bond or a double bond, provided that at least one of the two adjacent bonds is a single bond.