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The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Patent No.:

US 10995093 B1

PDFFull Text
Date of Patent:
May. 04, 2021

Filed:

Nov. 29, 2019

Synthesis of 2'-fluoro-6′-methylene-carbocyclic adenosine (fmca) and 2′-fluoro-6′methylene-carbocyclic guanosine (fmcg)

Applicant:

University of Georgia Research Foundation, Inc., Athens, GA (US);

Inventors:

Chung K. Chu, Stratham, GA (US);

Varughese Alexander Mulamootttil, Athens, GA (US);

Ram C. Mishra, Conyers, GA (US);

Uma Sharan Singh, Athens, GA (US);

Assignee:

UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC., Atlanta, GA (US);

Attorneys:

Henry D. Coleman

R. Neil Sudol

Primary Examiner:

Jeffrey H Murray

Int. Cl.
CPC ...
C07D 473/18 (2006.01); C07D 473/34 (2006.01); C07D 317/44 (2006.01); C07F 9/6561 (2006.01); C07D 473/40 (2006.01); C07D 473/26 (2006.01); C07C 41/30 (2006.01); C07C 41/26 (2006.01); C07C 41/28 (2006.01); A61P 31/20 (2006.01); C07C 43/196 (2006.01);
U.S. Cl.
CPC ...
C07D 473/34 (2013.01); C07C 41/26 (2013.01); C07C 41/28 (2013.01); C07C 41/30 (2013.01); C07D 317/44 (2013.01); C07D 473/18 (2013.01); C07D 473/26 (2013.01); C07D 473/40 (2013.01); C07F 9/65616 (2013.01); A61P 31/20 (2018.01); C07C 43/196 (2013.01); C07C 2601/08 (2017.05);
Abstract

The invention provides a new convergent approach for the synthesis of 2'-fluoro-6′-methylene-carbocyclic adenosine (FMCA) and 2′-fluoro-6′-methylene-carbocyclic guanosine (FMCG) from a readily available starting material in eight steps. An efficient and practical methodology for stereospecific preparation of a versatile carbocyclic key intermediate, (1S,3R, 4R)-3-tert-butoxy-4-(tert-butoxymethyl)-2-fluoro-5-methylenecyclopentanol (compound 8 of scheme 1A or a) in only six (6) steps is also provided. Prodrugs of these compounds are also prepared.

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