http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-2574586-T3

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filingDate 2008-01-02-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 2016-06-20-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_96525e93e8f40a823c0c5600e2f9f355
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_53324906a85202d570909eeef81306ea
publicationDate 2016-06-20-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber ES-2574586-T3
titleOfInvention Improved procedure for the preparation of oxidized phospholipids
abstract A process for preparing a compound having a glycerol backbone and at least one residue containing an oxidized fraction linked to the glycerol backbone via an ether bond, the compound having the general formula II: ** Formula ** where: A1 is selected from the group consisting of CH2 and C> = O; A2 is CH2; R1 is an alkyl having 1-30 carbon atoms; ** Formula ** R2 is while: X is an alkyl chain having 1-24 carbon atoms; Y is hydrogen; and Z is ** Formula ** Y R3 is selected from the group consisting of hydrogen, alkyl, aryl, phosphoric acid, phosphorylcholine, phosphorylethanolamine, phosphorylserine, phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, phosphorylcardiolphospoline, phosphorylcardiolphositol, phosphorylethanol, phosphorylpropanol, phosphorylbutanol, phosphorylethanolamine-N-lactose, phosphoethanolamine-N- [methoxy (propylene glycol)], phosphoinositol-4-phosphate, phosphoinositol-4,5-bisphosphonate, pyrophosphate, phosphoethanolamine-diethylene triamine-phosphoethanolamine-diethylene triamine , the process comprising: supplying a first compound having a glycerol backbone and at least one free hydroxyl group, said first compound having the general Formula I: ** Formula ** where A1 and R1 are as defined for Formula II, and R3 is selected from the group consisting of hydrogen, alkyl, and aryl; supplying a second compound having at least one unsaturated bond that can undergo oxidative cleavage, and at least one reaction group capable of forming an ether bond with said free hydroxyl group; reaction of said first compound and said second compound to thus obtain a third compound, said third compound having said glycerol backbone and a residue containing an unsaturated bond being linked to said glycerol backbone by means of an ether bond in the position sn-2; where when R3 of said first compound is hydrogen, the process further comprises, before the reaction of said first compound and said second compound, the protection of a free hydroxyl group in the sn-3 position of said glycerol backbone with a group protective, such that said compound comprises said protective group in said sn-3 position; collecting said third compound; supplying a solution of said third compound in a non-polar solvent, said non-polar solvent being selected such that said third compound is soluble therein when the impurities formed during said reaction are insoluble therein, thus providing a mixture that includes said solution of said third compound in said nonpolar solvent and insoluble impurities; removal of insoluble impurities; and removal of said non-polar solvent, to thereby obtain a third purified compound; reaction of said third purified compound with an oxidizing agent comprising a mixture of a periodate and a permanganate in such a way that said unsaturated bond is oxidized to form said Z, thus obtaining a fourth compound, said fourth compound having said glycerol backbone and a residue containing an oxidized fraction attached to said glycerol backbone by means of an ether bond in the sn- position and isolation of said fourth compound using phase separation to thus obtain a purified fourth compound, thus obtaining the compound having a glycerol backbone and at least one residue containing an oxidized fraction attached to said glycerol backbone by means of an ether bond, said isolation of said third compound and said isolation of said fourth compound devoid of column chromatography, where when the compound having a glycerol backbone and at least a residue containing an oxidized fraction attached to the glycerol backbone further comprises a phosphorous-containing fraction attached to the glycerol backbone, such that R3 is selected from the group consisting of phosphoric acid, phosphorylcholine, phosphorylethanolamine, phosphorylserine , Phosphatidylcholine, Phosphatidylethanolamine, Phosphatidylserine, Phosphatidylinositol, Phosphorylcardiolipine, Phosphorylinositol, Ethylphosphocholine, Phosphorylmethanol, Phosphorylethanol, Phosphorylpropanol, Phosphorylbutanol, Phosphorylethanolamine-N-ethanolactose, phosphorylethanolamine-N-ethanolactose, phosphorylethanolamine-4-methoollicinos-4 5-bisphosphonate, pyrophosphate, phosphoethanolamine-diethylenetriamine-pentaacetate, dinitrophenylphosphoethanolamine, phosphoethanolamine, phosphoglycerol, the process further comprises, after isolation of said fourth compound: supplying said fourth purified compound having a free hydroxyl group; reaction of said fourth purified compound with a phosphorous-containing reaction compound having a second reaction group and a third reaction group, said second reaction group being capable of reacting with said free hydroxyl group, to thereby provide said fourth purified compound having a phosphorous-containing reaction group attached to the glycerol backbone; and converting said phosphorous-containing reaction group to said phosphorus-containing fraction.
priorityDate 2007-01-09-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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