Alkyl-, alkenyl- and alkynylcarbamate derivatives, their preparation and their application in therapeutics

Abstract

The invention relates to a compound of formula (I): Wherein R 1 , R 2 , R 3 and R 4 are as defined herein. The invention also relates to methods of preparation of compounds of formula (I) as well as to their therapeutic application.

1 . A method of treating a disease in a patient, said disease selected from the group consisting of acute or chronic pain, dizziness, vomiting, nausea, eating disorder, neurological or psychiatric pathology, acute or chronic neurodegenerative disease, epilepsy, sleep disorder, cardiovascular disease, renal ischemia, disorders of the immune system, allergic disease, parasitic, viral or bacterial infectious disease, inflammatory disease, osteoporosis, gastrointestinal disease and urinary incontinence, comprising administering to said patient a therapeutically effective amount of a compound of formula (I) or a hydrate or a solvate thereof: 
     
       
         
         
             
             
         
       
     
     in which
 R 1  represents a C 5-26 -alkyl, C 5-26 -alkenyl or C 5-26 -alkynyl group or a polyunsaturated aliphatic carbon group comprising between 5 and 26 carbon atoms and comprising at least two unsaturations chosen from double and triple bonds; 
 R 2  represents a hydrogen atom or a C 1-6 -alkyl group; 
 R 3  represents a hydrogen atom or a C 1-3 -alkyl group; and 
 R 4  represents a hydrogen atom or a C 1-4 -alkyl, C 3-7 -cycloalkyl or C 3-7 -cycloalkyl-C 1-3 -alkyl group. 
 
   
   
       2 . The method according to  claim 1 , wherein:
 R 1  represents a C 5-26 -alkyl group, a C 5-26 -alkenyl group or a polyunsaturated aliphatic carbon group comprising between 5 and 26 carbon atoms and comprising at least two unsaturations chosen from double bonds;   R 2  represents a hydrogen atom or a C 1-6 -alkyl group;   R 3  represents a hydrogen atom or a C 1-3 -alkyl group; and   represents a hydrogen atom or a C 1-4 -alkyl, C 3-7 -cycloalkyl or C 3-7 -cycloalkyl-C 1-3 -alkyl group.   
   
   
       3 . The method according to  claim 1 , wherein:
 R 3  represents a hydrogen atom or a C 1-3 -alkyl group; and   R 4  represents a hydrogen atom or a C 1-4 -alkyl group.   
   
   
       4 . The method according to  claim 1 , wherein:
 R 1  represents a C 10-20 -alkyl, C 10-20 -alkenyl or C 10-20 -alkynyl group or a polyunsaturated aliphatic carbon group comprising between 10 and 20 carbon atoms and comprising at least two unsaturations chosen from double and triple bonds;   R 2  represents a hydrogen atom or a C 1-6 -alkyl group;   R 3  represents a hydrogen atom or a C 1-3 -alkyl group; and   R 4  represents a hydrogen atom or a C 1-4 -alkyl, C 3-7 -cycloalkyl or C 3-7 -cycloalkyl-C 1-3 -alkyl group.   
   
   
       5 . The method according to  claim 1 , wherein:
 R 1  represents a C 10-20 -alkyl group, a C 10-20 -alkenyl group or a polyunsaturated aliphatic carbon group comprising between 10 and 20 carbon atoms and comprising at least two unsaturations chosen from double bonds;   R 2  represents a hydrogen atom or a C 10-20 -alkyl group;   R 3  represents a hydrogen atom or a C 1-3 -alkyl group; and   R 4  represents a hydrogen atom or a C 1-4 -alkyl group.   
   
   
       6 . The method according to  claim 1 , wherein the disease is neurological or psychiatric pathology. 
   
   
       7 . The method according to  claim 6 , wherein said neurological or psychiatric pathology is selected from tremor, dyskinesia, dystonia, spasticity, obsessive-compulsive behavior, Tourette's syndrome, depression and anxiety. 
   
   
       8 . The method according to  claim 7 , wherein said neurological or psychiatric pathology is selected from depression or anxiety. 
   
   
       9 . The method according to  claim 1 , wherein the disease is acute or chronic neurodegenerative disease. 
   
   
       10 . The method according to  claim 9 , wherein said acute or chronic neurodegenerative disease is selected from Parkinson's disease, Alzheimer's disease, senile dementia, Huntington's chorea and lesions related to cerebral ischemia, cranial and medullary trauma. 
   
   
       11 . The method according to  claim 1 , wherein the disease is epilepsy. 
   
   
       12 . The method according to  claim 1 , wherein the disease is sleep disorder.