Dupont Pharmaceuticals Company

Rodney Lawrence Parsons, Jr

Mona Patel

Joseph M Fortunak

Soo Sung Ko

Steven P Seitz

Anthony J Cocuzza

Michael Ernest Pierce

Lilian Alicia Radesca

Anusuya Choudhury

Abdul Ezaz Mutlib

Shelley R Rabel

David Donald Christ

Jay Andrew Markwalder

The present invention relates to benzoxazinones of formula I:

4,4-disubstituted-1,4-dihydro-2h-3,1-benzoxazin-2-ones useful as HIV reverse transcriptase inhibitors and intermediates and processes for making the same

The potent reverse transcriptase inhibitor (&minus;)-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-3,4-dihydro-2(1H)-quinazolinone is produced in solvate and crystalline form. These forms are designated Forms 1 and 2, and are characterized by x-ray powder diffraction and differential scanning calorimetry. Pharmaceutical compositions and methods are useful for the treatment of the human immunodeficiency virus (HIV).

Crystalline (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-3,4-dihydro-2(1H)-quinazolinone

The present invention relates to benzoxazinones of formula I: ##STR1## or stereoisomeric forms or mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HIV reverse transcriptase, and to pharmaceutical compositions and diagnostic kits comprising the same, methods of using the same for treating viral infection or as an assay standard or reagent, and intermediates and processes for making the same.

4,4-disubstituted-1,4-dihydro-2H-3,1-benzoxazin-2-ones useful as HIV

The present invention relates generally to novel methods for the synthesis of cyclopropylacetylene which is a reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one which is a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor.

Synthesis of cyclopropylacetylene

The present invention provides novel methods for the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1- benzoxazin-2-one of formula (VI-i) ##STR1## which is useful as a human immunodeficiency virus (HIV) reverse transcriptase inhibitor.

Asymmetric synthesis of benzoxazinones

4,4-disubstitued-1,4-dihydro-2H-3,1-benzoxazin-2-ones useful as HIV

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Wilmington, DE, United States of America

Rodney Lawrence Parsons, Jr