Invention Grant
- Patent Title: Process for synthesizing ergothioneine and related compounds
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Application No.: US15513237Application Date: 2015-09-22
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Publication No.: US09908854B2Publication Date: 2018-03-06
- Inventor: Moegamat Anwar Jardine , Lutete Peguy Khonde
- Applicant: University of Cape Town
- Applicant Address: ZA Cape Town
- Assignee: University of Cape Town
- Current Assignee: University of Cape Town
- Current Assignee Address: ZA Cape Town
- Agency: Andrus Intellectual Property Law, LLP
- Priority: GB1416678.9 20140922
- International Application: PCT/IB2015/001668 WO 20150922
- International Announcement: WO2016/046618 WO 20160331
- Main IPC: C07D233/84
- IPC: C07D233/84 ; A61K31/4164

Abstract:
The invention provides a process for synthesising a compound of formula V wherein: n is 0, 1 or 2; and R is H or or a physiologically acceptable salt, tautomer, stereoisomer or mixture of stereoisomers thereof. The process utilizes a N-benzyl protected histidine rather than the unprotected form of histidine. The process of the invention comprises the steps of: (a) deprotecting a N-benzyl protected histidine of formula 11 to form N-benzyl histidine of formula 12; (b) converting compound 12 to (S)-3-(1-benzyl-1H-imidazol-4-yl)-2-(dimethylamino)propanoic acid of formula 13; (c) converting compound 13 to (2S)-N,N,N-2-trimethylethanaminium-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid of formula 14; (d) brominating the imidazole ring of the compound of formula 14 to form 5-bromohercynine lactone (reactive intermediate); and (e) converting the 5-bromohercynine lactone of step (d) to (β-amino-β-carboxyethyl)ergothioneine sulfide of formula 15. The process optionally further includes one of steps (f) to (h): (f) converting the compound of formula 15 to a sulfoxide; (g) converting the compound of formula 15 to a sulfone; or (h) converting the compound of formula 15 to ergothioneine (ESH).
Public/Granted literature
- US20170305865A1 PROCESS FOR SYNTHESIZING ERGOTHIONEINE AND RELATED COMPOUNDS Public/Granted day:2017-10-26
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