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.

Date of Patent:
Sep. 28, 1999

Filed:

Mar. 27, 1996
Applicant:
Inventors:

Gary P Kirschenheuter, Arvada, CO (US);

Bruce Eaton, Boulder, CO (US);

Assignee:

NeXstar Pharmaceuticals, Inc., Boulder, CO (US);

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07H / ;
U.S. Cl.
CPC ...
536 2626 ; 536 2534 ; 536 266 ; 536 268 ; 536 281 ; 536 282 ; 536 283 ; 536 284 ; 536 285 ; 536 2851 ; 536 2852 ; 536 2853 ; 536 2854 ; 536 2855 ; 435 23 ; 530300 ;
Abstract

Modified nucleosides and methods of making and using the nucleosides are disclosed. The compounds can be prepared by reacting nucleoside starting materials that contain a suitable leaving group at one or more of the carbon atoms in the purine or pyrimidine ring, with a vinylstannane, carbon monoxide, and a palladium catalyst to provide 1-ene-3-one intermediates. These intermediates are then reacted with suitably functionalized primary or secondary amines via a Michael reaction. When the intermediate is a 5-position modified pyrimidine ring, and the amine contains a second hydrogen, it can do a second Michael reaction with the ene-one or the ene-imine in the pyrimidine ring. Appropriate modification of the amine reactant can yield products with various bioactivities. The nucleosides can be used therapeutically as anti-cancer, anti-bacterial or anti-viral drugs. The nucleosides can also be used for diagnostic applications, for example, by incorporating a radiolabel or fluorescent label into the molecule. The nucleosides can be used to prepare oligonucleotides for use in various applications, either alone or in combination with other modified nucleosides and/or naturally occurring nucleosides.


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