Substituted semicarbazides and the use thereof

Details Substituted semicarbazides and the use thereof Substituted semicarbazides and the use thereof

C - Chemistry, Metallurgy

07

C

C07C 281/06 (2006.01) A61K 31/175 (2006.01) A61K 31/40 (2006.01) A61K 31/47 (2006.01) A61K 31/535 (2006.01) C07D 207/04 (2006.01) C07D 207/08 (2006.01) C07D 211/70 (2006.01) C07D 215/16 (2006.01) C07D 215/38 (2006.01) C07D 251/00 (2006.01) C07D 265/30 (2006.01) C07D 307/02 (2006.01) C07D 315/00 (2006.01) C07D 401/00 (2006.01) C07D 413/00 (2006.01)

Patent

CA 2319484

This invention is related to substituted semicarbazides represented by Formula (I) or a pharmaceutically acceptable salt or prodrug thereof, wherein: R1 and R2 are independently hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, aryl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or carboxyalkyl; R3, R4, R5 and R6 are independently hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, aryl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or carboxyalkyl, or R3 and R4 is defined as above, and R5 and R6 together with the nitrogen atom to which they are attached form a heterocycle, including piperidine, piperazine, morpholine; A1 and A2 are independently aryl, heteroaryl, saturated or partially unsaturated carbocycle or satured or partially unsaturated heterocycle, any of which is optionally substituted; X is one of O, S, NR7, CH2, C(O), NR7C(O), C(O)NR7, SO, SO2 or a covalent bond; where R7 is hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, aryl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or carboxyalkyl; n is 0, 1, 2 or 3. m is 0, 1, 2 or 3. The invention also is directed to the use of substituted semicarbazides 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), and for the treatment, prevention or amelioration of both acute or chronic pain, as anticonvulsants, and as antimanic depressants, as anti-migraine agents, as local anesthetics, as antiarrhythmics and for the treatment or prevention of diabetic neuropathy.

L'invention concerne des semicarbazides substitués représentés par la formule (I), un sel pharmaceutiquement acceptable ou un promédicament de ceux-ci. Dans cette formule, R¿1? et R¿2? représentent chacun indépendamment hydrogène, alkyle, cycloalkyle, alcényle, alcynyle, haloalkyle, aryle, aminoalkyle, hydroxyalkyle, alcoxyalkyle ou carboxyalkyle; R¿3?, R¿4?, R¿5? et R¿6? sont indépendamment hydrogène, alkyle, cycloalkyle, alcényle, alcynyle, haloalkyle, aryle, aminoalkyle, hydroxyalkyle, alcoxyalkyle ou carboxyalkyle; ou R¿3? et R¿4? sont définis comme susmentionnés, et R¿5? et R¿6? forment ensemble avec l'atome d'azote auquel ils sont attachés un hétérocycle comprenant pipéridine, pipérazine, morpholine; A¿1? et A¿2? représentent indépendamment aryle, hétéroaryle, cyclocarbone saturé ou partiellement non saturé ou hétérocycle saturé ou partiellement non saturé, l'un quelconque étant éventuellement substitué. X représente l'un de O, S, NR¿7?, CH¿2?, C(O), NR¿7?C(O), C(O)NR¿7?, SO, SO¿2? ou une liaison covalente; où R¿7? est hydrogène, alkyle, cycloalkyle, alcényle, alcynyle, haloalkyle, aryle, aminoalkyle, hydroxyalkyle, alcoxyalkyle ou carboxyalkyle; n est 0, 1, 2 ou 3. m est 0, 1, 2 ou 3. L'invention concerne également l'utilisation des semicarbazides substitués pour traiter les lésions neuronales consécutives à une ischémie globale ou focale, pour traiter ou prévenir des états neurodégénératifs tels que la sclérose latérale amyotrophique (ALS), pour traiter, prévenir ou améliorer une douleur chronique ou aiguë et pour traiter ou prévenir la neuropathie diabétique. Ces semicarbazides sont notamment des anesthésiques locaux, des dépresseurs anti-maniaco-dépressifs, des médicaments antimigraineux, des anesthésiques locaux, des antiarythmiques.

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