Invention Grant
- Patent Title: Processes for stereoselective synthesis of trans ISATX247
- Patent Title (中): 用于立体选择性合成反式ISATX247的方法
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Application No.: US11572833Application Date: 2005-07-26
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Publication No.: US07799756B2Publication Date: 2010-09-21
- Inventor: Bruce F. Molino , Zhicai Yang , Jun-Ho Maeng , David D. Manning
- Applicant: Bruce F. Molino , Zhicai Yang , Jun-Ho Maeng , David D. Manning
- Applicant Address: US NY Albany
- Assignee: Albany Molecular Research, Inc.
- Current Assignee: Albany Molecular Research, Inc.
- Current Assignee Address: US NY Albany
- Agency: Nixon Peabody LLP
- International Application: PCT/US2005/026319 WO 20050726
- International Announcement: WO2006/014872 WO 20060209
- Main IPC: A61K38/13
- IPC: A61K38/13 ; A61K38/12

Abstract:
The present invention relates to a process for preparation of a trans ISATX247 compound of the formula: where R1═H or D; R2═H or D; and R3═H or D, by application of organozirconium chemistry. The process involves reacting an acetyl cyclosporin aldehyde with an organozirconium reagent to provide acetyl cyclosporin diene (the acetate of trans ISATX247) and deacetylating the acetyl cyclosporin diene to produce the trans-isomer of ISATX247. The present invention also relates to a process for preparing the same trans ISATX 247 compound, using olefin cross metathesis. The process involves: olefin cross metathesis of acetyl cyclosporin A to afford acetyl cyclosporin α,β-unsaturated aldehyde; Wittig reaction of the acetyl cyclosporin α,β-unsaturated aldehyde to provide acetyl cyclosporin diene; and deacetylation of the acetyl cyclosporin diene to produce the trans ISATX247 compound. Also disclosed are processes for preparing an acetyl cyclosporin α,β-unsaturated aldehyde compound and a cyclosporin triene analogue compound.
Public/Granted literature
- US20080021197A1 NOVEL PROCESSES FOR STEREOSELECTIVE SYNTHESIS OF TRANS ISATX247 Public/Granted day:2008-01-24
Information query
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