Generated: May 27, 2017
|Title:||Synthesis of UDP-Glucose: N-acylsphingosine glucosyl transferase inhibitors|
|Abstract:||Disclosed is a novel enantiomeric synthesis ceramide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.|
|Inventor(s):||Hirth; Bradford H. (Littleton, MA), Siegel; Craig (Woburn, MA)|
|Assignee:||Genzyme Corporation (Cambridge, MA)|
|Filing Date:||Mar 14, 2012|
|Claims:||1. A method of preparing a sphingosine-like compound represented by the following structural formula: ##STR00032## said method comprising the stop of reacting a cyclic starting material with HNR.sub.2R.sub.3,said starting material represented by the following structural formula: ##STR00033## thereby forming an intermediate represented by the following structural formula: ##STR00034## and hydrolyzing the amino acetal group of the intermediate, thereby forming an acyclic compound represented by the following structural formula: ##STR00035## reacting the acyclic compound with an amide reducing agent, thereby forming an amine compound represented by the following structural formula: ##STR00036## debenzylating the --NHCH(--CH.sub.2OH)R.sub.5 group of the amine compound, thereby forming a sphingosine-like compound represented by the following structural formula: ##STR00037## wherein: R.sub.1 is a substituted or unsubstituted aromatic group; R.sub.2 and R.sub.3 are independently --H, a substituted or unsubstituted aliphatic group or, taken together with the nitrogen atom to which they art bonded, are a substituted or unsubstituted non-aromatic heterocyclie ring; and R.sub.5 is a substituted or unsubstituted aromatic group. |
2. The method of claim 1 wherein the amine compound is debenzylated by hydrogenation.
3. The method of claim 2 wherein the amine compound is debenzylated by hydrogenation under a hydrogen atmosphere with a catalytic amount of a hydrogenation catalyst.
Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.