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21. 发明授权

US5977385A Method for the preparation of (+)-calanolide A and analogues thereof 失效
公开(公告)号：US5977385A
公开(公告)日：1999-11-02
申请号：US115984
申请日：1998-07-15
申请人： Michael T. Flavin , Ze-Qi Xu , Albert Khilevich , David Zembower , John D. Rizzo , Shuyuan Liao , Aye Mar , Lin Lin , Vilayphone Vilaychack , Darko Brankovic , Sergey Dzekhster , Jinjun Liu
发明人： Michael T. Flavin , Ze-Qi Xu , Albert Khilevich , David Zembower , John D. Rizzo , Shuyuan Liao , Aye Mar , Lin Lin , Vilayphone Vilaychack , Darko Brankovic , Sergey Dzekhster , Jinjun Liu
IPC分类号： A61K45/06 , C07D311/16 , C07D493/04 , C07D493/14 , C07D493/00
CPC分类号： C07D493/04 , A61K45/06 , C07D311/16 , C07D493/14
摘要： A method of preparing (+)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. According to the disclosed method, chromene 4 intermediate was subjected to a chlorotitanium-mediated aldol reaction with acetaldehyde to selectively produce (.+-.)-8a. Separation and enzyme-mediated resolution of (.+-.)-8a produced (+)-8a. Cyclization of (+)-8a under neutral Mitsunobu conditions followed by Luche reduction of (+)-7 produced (+)-calanolide A in high yield and enantiomeric purity. The method of the invention has been extended to produce potent antiviral calanolide A analogues.

22. 发明授权

US5859050A Method for the preparation of (+)-calanolide A and analogues thereof 失效
公开(公告)号：US5859050A
公开(公告)日：1999-01-12
申请号：US926307
申请日：1997-09-05
申请人： Michael T. Flavin , Ze-Qi Xu , Albert Khilevich , David Zembower , John D. Rizzo , Lin Lin
发明人： Michael T. Flavin , Ze-Qi Xu , Albert Khilevich , David Zembower , John D. Rizzo , Lin Lin
IPC分类号： A61K45/06 , C07D311/16 , C07D493/04 , C07D493/14 , A61K31/35
CPC分类号： C07D493/04 , A61K45/06 , C07D311/16 , C07D493/14
摘要： A method of preparing (+)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. According to the disclosed method, chromene 4 intermediate was subjected to a chlorotitanium-mediated aldol reaction with acetaldehyde to selectively produce (.+-.)-8a. Separation and enzyme-mediated resolution of (.+-.)-8a produced (+)-8a. Cyclization of (+)-8a under neutral Mitsunobu conditions followed by Luche reduction of (+)-7 produced (+)-calanolide A in high yield and enantiomeric purity. The method of the invention has been extended to produce potent antiviral calanolide A analogues.

23. 发明授权

US5840921A Method for the preparation of aldol product 7B 失效
标题翻译：醛醇产品7B的制备方法
公开(公告)号：US5840921A
公开(公告)日：1998-11-24
申请号：US925992
申请日：1997-09-09
申请人： Michael T. Flavin , Ze-Qi Xu , John D. Rizzo , Albert Khilevich
发明人： Michael T. Flavin , Ze-Qi Xu , John D. Rizzo , Albert Khilevich
IPC分类号： C07D311/58 , A61K31/365 , A61K45/06 , A61P31/12 , A61P37/04 , C07D311/16 , C07D493/04 , C07D493/14 , C07D493/00
CPC分类号： C07D493/04 , A61K45/06 , C07D311/16 , C07D493/14
摘要： A method of preparing (.+-.)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. Useful intermediates for preparing (+)-calanolide A and its derivatives are also provided. According to the disclosed method, chromene 4 intermediate was reacted with acetaldehyde diethyl acetal or paraldehyde in the presence of an acid catalyst with heating, or a two-step reaction including an aldol reaction with acetaldehyde and cyclization either under acidic conditions or neutral Mitsunobu conditions, to produce chromanone 7. Reduction of chromanone 7 with sodium borohydride, in the presence of cerium trichloride, produced (.+-.)-calanolide A. A method for resolving (.+-.)-calanolide A into its optically active forms by a chiral HPLC system or by enzymatic acylation and hydrolysis is also disclosed. Finally, a method for treating or preventing viral infections using (.+-.)-calanolide A or (-)-calanolide A is provided.
摘要翻译：提供了从色烯4制备（+/-） - 丙内酰脲A，1，一种有效的HIV逆转录酶抑制剂的方法。还提供了制备（+） - 蒎烯内酯A及其衍生物的有用的中间体。根据所公开的方法，在酸催化剂的存在下，将色烯4中间体与乙醛二乙基缩醛或对甲醛反应，或者在酸性条件或中性Mitsunobu条件下，包括醛醇与乙醛反应和醛化反应的两步反应，产生苯并二氢吡喃酮7.在三氯化铈的存在下，用硼氢化钠还原色酮7.产生（+/-） - 甘露糖苷A。一种通过手性拆分（+/-） - 卡立拉内酯A至其光学活性形式的方法还公开了HPLC系统或通过酶酰化和水解。最后，提供了一种使用（+/-） - 蒎烯内酰胺A或（ - ） - cal醇酯A治疗或预防病毒感染的方法。

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