US 9,790,171 B2 · Synthesis intermediates for obtaining derivatives of sphingosines, ceramides and sphingomyelins with good yields

Abstract

The subject matter of the present invention is the novel molecules of formulae E, E′ and F. These molecules prove to be synthesis intermediates that are very advantageous for the manufacture of derivatives of sphingosine or of ceramides functionalized in position 1, with good yields, in which R1 and R2 are fatty chains, R3 is an alkyl group and R4 is a protective group for alcohol functions. Another subject of the invention is the use of the intermediates of type F for converting same into intermediates of type G, by means of reduction in the presence of lithium borohydride. The G molecules are precursors that are known to make it possible to obtain sphingolipids or sphingomyelin.

Claims20

Dependent claims

Synthesis intermediates E′ and F to access derivatives of sphingosine or ceramides, of general formulas:

wherein
R1 is a straight-chain or branched aliphatic chain of general formula CpH2p+1Or, where p is an integer of between 8 and 35, and r is an integer of between 0 and 2;
R2 is an aliphatic fatty chain of general formula CnH2n+1, n being an integer greater than or equal to 8 and less than or equal to 35;
R3 is a radical having at least 1 carbon atom of alkyl, aryl, alkyl-aryl type optionally substituted;
and
R4 is a protective group of the alcohol functions, wherein, the protective group is selected from the group consisting of benzyl, trityl, benzoyl, methoxymethyl, methoxyethyl, tetrahydropyryl, tri-alkyl silyl and alkyl-aryl silyl radical.

3 more elements

Dependencies are inferred from the claim text.

Facts

Application

14/760,561Filed 14 Jan 2014

Priority

FR 13 0006314 Jan 2013

Published

US 2016/0083335 A124 Mar 2016

Granted

17 Oct 2017

Term ends

Not estimatedThe source records don’t support an estimate.

Classification10 codes

C07C 233/31
Having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound…:…
C07C 229/08
Having only one amino and one carboxyl group bound to the carbon skeleton: the nitrogen atom of the amino group being further bound to hydrogen atoms
C07C 231/02
Preparation of carboxylic acid amides: from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
C07C 231/12
Preparation of carboxylic acid amides: by reactions not involving the formation of carboxamide groups

Synthesis intermediates for obtaining derivatives of sphingosines, ceramides and sphingomyelins with good yields

Life of this patent

Synthesis intermediates for obtaining derivatives of sphingosines, ceramides and sphingomyelins with good yields

Life of this patent

Abstract

Claims20