Patent EA-004768-B1 (EA)
Title: Pharmaceutical compositions containing oligosaccharides and preparation thereof
Inventor: MOURIER PIERRE
IPC: A61P25/02
Filed: 2001-03-26
Abstract: 1. A pharmaceutical composition containing as active principle an oligosaccharide of formula (I) in which n is an integer from 0 to 25, R1, R3, R4, R5 R6 and R8, identical or different, are a hydrogen atom or a SO3M radical, R2 and R7, identical or different are a hydrogen atom or a SO3M radical, or COCH3, and M is sodium, calcium, magnesium or potassium or a mixture of said oligosaccharides. 2. The pharmaceutical composition according to claim 1, comprising oligosaccharide of formula (I), in which R4 and R6 are a hydrogen atom or a mixture of said oligosaccharides. 3. The pharmaceutical composition according to claim 1 or 2, comprising oligosaccharide of formula (I), in which n is an integer from 0 to 10 or a mixture of said oligosaccharides. 4. The pharmaceutical composition according to claim 1 or 2, comprising oligosaccharide of formula (I), in which n is an integer from 0 to 6 or a mixture of said oligosaccharides. 5. The pharmaceutical composition according to claim 1 or 2, comprising oligosaccharide of formula (I), in which n is an integer from 0 to 6 or a mixture of said oligosaccharides. 6. The pharmaceutical composition according to claim 1, comprising oligosaccharide of formula (I), in which n is 0, R1, R7 and R8 are a SO3M radical, R6 is a hydrogen atom and M is sodium. 7. The pharmaceutical composition according to claim 1, comprising oligosaccharide of formula (I), in which n is 1, R1, R2, R3, R5, R7 and R8 are a SO3M radical, R4 and R6 are a hydrogen atom and M is sodium. 8. The pharmaceutical composition according to claim 1, comprising oligosaccharide of formula (I), in which n is 2, R1, R2, R3, R5, R7 and R8 are a SO3M radical, R4 and R6 are a hydrogen atom and M is sodium. 9. The pharmaceutical composition according to claim 1, comprising oligosaccharide of formula (I), in which n is 3, R1, R2, R3, R5, R7 and R8 are a SO3M radical, R4 and R6 are a hydrogen atom and M is sodium. 10. The pharmaceutical composition according to claim 1, comprising oligosaccharide of formula (I), in which n is 4, R1, R2, R3, R5, R7 and R8 are a SO3M radical, R4 and R6 are a hydrogen atom and M is sodium. 11. Oligosaccharide of the formula: in which n is an integer from 0 to 25, R1, R3, R4, R5 R6 and R8, identical or different, are a hydrogen atom or a SO3M radical, R2 and R7, identical or different are a hydrogen atom or a SO3M radical, or COCH3, and M is sodium, calcium, magnesium or potassium, except for compounds where n is 0, and either R1, R6 and R8 are hydrogen atoms, R7 is SO3M radical or COCH3 and M is sodium, or R1 and R6 a hydrogen atom, R7 is COCH3, R8 is SO3M, and M is sodium, or R6 is hydrogen, R1, R7 and R8 are SO3M, and M is sodium, or R6 and R7 are hydrogen atoms, R1and R8 are SO3M radical, and M is sodium, or R1, R6 and R7 are a hydrogen atom, R8 is SO3M radical, and M is sodium. 12. Oligosaccharide of formula (I) according to claim 11, in which R4 and R6 are a hydrogen atom. 13. Oligosaccharide of formula (I) according to one of claims 11 or 12, in which n is an integer from 0 to 10. 14. Oligosaccharide of formula (I) according to one of claims 11 or 12, in which n is an integer from 0 to 6. 15. Oligosaccharide of formula (I) according to one of claims 11 or 12, in which n is an integer from 1 to 6. 16. Oligosaccharide of formula (I), according to claim 11, in which n is 0, R1, R7 and R8 are a SO3M radical, R6 is a hydrogen atom and M is sodium. 17 Oligosaccharide of formula (I), according to claim 11, in which n is 1, R1, R2, R3, R5, R7 and R8 are a SO3M radical, R4 and R6 are a hydrogen atom and M is sodium. 18. Oligosaccharide of formula (I), according to claim 11, in which n is 2, R1, R2, R3, R5, R7 and R8 are a SO3M radical, R4 and R6 are a hydrogen atom and M is sodium. 19. Oligosaccharide of formula (I), according to claim 11, in which n is 3, R1, R2, R3, R5, R7 and R8 are a SO3M radical, R4 and R6 are a hydrogen atom and M is sodium. 20. Oligosaccharide of formula (I), according to claim 11, in which n is 4, R1, R2, R3, R5, R7 and R8 are a SO3M radical, R4 and R6 are a hydrogen atom and M is sodium. 21. A method for preparing oligosaccharides of formula (I) according to claim 11, wherein borohydride of alkali metals or quaternary ammonium reacts with oligosaccharides of the formula: in which n is an integer from 0 to 25, R1, R3, R4, R5 R6 and R8, identical or different, are a hydrogen atom or a SO3M radical, R2 and R7, identical or different are a hydrogen atom or a SO3M radical, or COCH3, and M is sodium, calcium, magnesium or potassium, and isolate oligosaccharides. 22. The method according to claim 21, wherein the reaction is carried out in aqueous medium at a temperature close to 25 degree C and pH between 7 to 10. 23. The method according to one of claims 21 and 22, wherein the reaction is carried out with pH between 9 to 10. 24. The method according to claims 21-23, wherein borohydride of alkali metals or quaternary ammonium is lithium, sodium, potassium or tetrabutylammonium boride. 25. Use of oligosaccharides of formula (I) in which n is an integer from 0 to 25, R1, R3, R4, R5 R6 and R8, identical or different, are a hydrogen atom or a SO3M radical, R2 and R7, identical or different, are a hydrogen atom or a SO3M radical, or COCH3, and M is sodium, calcium, magnesium or potassium or a mixture of said oligosaccharides for preparing of a medicament for preventing or treating inflammatory diseases involving sodium monoxide production. 26. Use of oligosaccharides of formula (I) according to claim 25 for preparing medicaments for use in preventing and treating cerebral, cardiac or peripheral vascular ischemias, osteoarthritis, traumas of central nervous system, craniocerebral and cerebrospinal traumas, disseminated sclerosis, neurotic pains and peripheric neuropathy, diseases of motoneurons, amyotrophic lateral sclerosis, neuro-ACID's, Alzheimer's disease, Parkinson's disease and Huntinton's chorea. 27. Use of oligosaccharides of formula (I) in which n is an integer from 0 to 25, R1, R3, R4, R5 R6 and R8, identical or different, are a hydrogen atom or a SO3M radical, R2 and R7, identical or different, are a hydrogen atom or a SO3M radical, or COCH3, and M is sodium, calcium, magnesium or potassium or a mixture of said oligosaccharides for preparing of a medicament for preventing or treating diseases related to survival and motoneurons growth.