Compositions containing and methods of using 1-aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives
AssigneeTeva Pharmaceutical Industries Ltd.
InventorsBenjamin Sklarz, Ramy Lidor, Eliezer Bahar, Yaacov Herzig, Jeff Sterling, Alex Veinberg
Life of this patent
Estimating the term…
Abstract
Novel derivatives of 1-aminoindan and their salts are described. Optically active 1-aminoindan derivatives are prepared by reacting a N-benzyl analog of the desired compound with an enantiomer of mandelic acid. Parkinson's disease, dementia, epilepsy, convulsions, or seizures are treated by administering a compound of the formula:
Claims21
A compound of the formula:
- wherein n is 0 or 1;
- each of R1 and R2 are independently hydrogen, substituted or unsubstituted C1-C4 alkyl, or halogen;
- R3 is hydrogen, substituted or unsubstituted C1-C4 alkyl, hydroxy, or substituted or unsubstituted C1-C4 alkoxy;
- R4 is hydrogen, or substituted or unsubstituted C1-C12 alkyl;
- and
- R5 is —C(O)—R6, —Y—(O)—NR9R10 or Y—(SO2)NR9R10,
- wherein R6 is substituted C1-C12 alkyl, substituted C6-C14 aryl, substituted or unsubstituted C7-C12 aralkyl, or A—N—R11Rl2,
- wherein A is substituted or unsubstituted C1-C12alkylene, and
- each of R11 and R12 are independently substituted or unsubstituted C1-C12 alkyl, substituted or
- unsubstituted C6-C12 aryl, or substituted or unsubstituted C7-C12 aralkyl, or indanyl,
- Y is substituted or unsubstituted C1-C12 alkylene, and each of R9 and R10, are independently hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 aryl, substituted or unsubstituted C7-C12 aralkyl or indanyl, provided that when R9 is hydrogen
- and R10 is phenyl, R3 is not dimethyl;
- and racemic mixtures, enantiomers, and salts thereof.
A compound of selected from the group consisting of N-(4-aminobutanoyl)-1-aminoindan, N-(2-aminoacetyl)-1-aminoindan, N,N′-bis-(1-indanyl)adipamide, N,N′-bis-(R)-(1-indanyl)adipamide, N,N′-bis-(R)-(1-indanyl)succinamide and racemic mixture, enantiomers, and salts thereof.
A compound of the formula:
- wherein n is 0 or 1;
- R1 is hydrogen, substituted or unsubstituted C1-C4 alkyl, or halogen;
- R2 is substituted or unsubstituted C1-C4 alkyl, or halogen;
- R3 is hydrogen, substituted or unsubstituted C1-C4 alkyl, hydroxy, or substituted or unsubstituted C1-C4 alkoxy;
- R4 is hydrogen, or substituted or unsubstituted C1-C12 alkyl;
- and
- R5 is —C(O)—R6, —Y—C(O)—NR11R12 or Y—(SO2)NR9R10,
- wherein R6 is substituted C1-C12 alkyl, substituted C6-C12 aryl, substituted or unsubstituted C7-C12 aralkyl, or A—N—R9R10,
- wherein A is substituted or unsubstituted C1-C12 alkylene, and
- each of R9 and R10 are independently hydrogen,
- substituted or unsubstituted C1-C12 alkyl,
- substituted or unsubstituted C6-C12 aryl, or
- substituted or unsubstituted C7-C12 aralkyl, or
- indanyl,
- Y is substituted or unsubstituted C1-C12 alkylene, and each of R11 and R12 are independently substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted
- C6-C12 aryl, or substituted or unsubstituted C7-C12 aralkyl;
- and racemic mixtures, enantiomers, and salts thereof.
Dependencies are inferred from the claim text.