Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof

US6696442B2 · kind B2 · utility

Assignee

• Euro-Celtique S.A. · LU

Inventors

• Yan Wang · San Diego, US
• Sui Xiong Cai · San Diego, US
• Nancy C. Lan · Altadena, US
• John F. W. Keana · Eugene, US
• Victor I. Ilyin · Montgomery, US

Key dates

• Filing date: Jun 25, 2002
• Grant date: Feb 24, 2004
• Expiry date: Jun 25, 2022

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2601/14
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

This invention is related to carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones represented by Formula I: or a pharmaceutically acceptable salt or prodrug thereof, wherein:Y is oxygen or sulfur; R1, R21, R22 and R23 are independently hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, aryl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or carboxyalkyl-82-; or R22 and R23, together with the N, form a heterocycle; A1 and A2 are independently aryl, heteroaryl, saturated or partially unsaturated carbocycle or saturated or partially unsaturated heterocycle, any of which is optionally substituted; X is one or O, S, NR24, CR25R26, C(O), NR24C(O), C(O)NR24, SO, SO2 or a covalent bond; where R24, R25 and R26 are independently hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, aryl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or carboxyalkyl. The invention also is directed to the use of carbocycle and heterocycle substituted semicarbazones and thiosemicarbazones for the treatment of neuronal damage following global and focal ischemia, for the treatment or prevention of neurodegenerative conditions such as amyotrophic lateral sclerosis (ALS), for the treatment and p…