139255-65-5Relevant academic research and scientific papers
Development of an Improved Route to a Human Immunodeficiency Virus Maturation Inhibitor by Chromium-Free Allylic Oxidation and an Efficient Asymmetric Henry Reaction
Herkommer, Daniel,Hunter, Sarah,Lynn, Sean M.,Manley, David,Rushworth, Philip,Slater, Fiona,Strachan, John B.,Woods, Martin
, p. 288 - 298 (2022/02/17)
Development of an improved route to a human immunodeficiency virus maturation inhibitor is described. Key features of the chemistry that was developed include avoidance of chromium reagents by use of a novel allylic oxidation with NBS/water and an aldehyde oxidation using either bleach/TEMPO under flow conditions or dichlorodimethylhydantoin in batch. It was demonstrated that an imine could be used for in situ protection of a labile aldehyde, and the mixed anhydride for the acetylation was optimized. A highly enantioselective Henry reaction was developed, and it was demonstrated that hazardous Raney nickel could be replaced by hydrogenation over platinum.
C-3 NOVEL TRITERPENONE WITH C-17 N-AMIDE DERIVATIVES AS HIV INHIBITORS
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, (2018/03/06)
The present invention relates to C-3 novel triterpenone with C-17 N-amide compounds of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6 and 'X' are as defined in formula (I). The invention also relates to compounds of formula (I), its related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.
C-3 NOVEL TRITERPENONE WITH C-28 HETEROCYCLE DERIVATIVES AS HIV INHIBITORS
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, (2018/03/06)
The present invention relates to C-3 novel triterpenone with C-28 heterocycle compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein R1, W, ring X and ring Y are as defined in formula (I). The present invention comprising compound of formula (I) and related compounds, compositions are useful for therapeutic treatment of viral diseases, particularly HIV mediated diseases.
C-3 NOVEL TRITERPENONE WITH C-28 DIAMIDE DERIVATIVES AS HIV INHIBITORS
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, (2018/03/28)
The present invention relates to C-3 novel triterpenone with C-28 diamide compounds of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6 and 'm' are as defined in formula (I). The present invention also relates to compounds of formula (I) and their related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.
C-3 NOVEL TRITERPENONE WITH C-17 REVERSE AMIDE DERIVATIVES AS HIV INHIBITORS
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, (2018/03/06)
The present invention relates to C-3 novel triterpenone with C-17 reverse amide compounds of Formula (I); and pharmaceutically acceptable salts thereof, wherein ring Formula (II), R1, R2, R3, R4, R5, R6, R7, 'n' and 'm' are as defined in Formula (I). The invention also relates to C-3 novel triterpenone with C-17 reverse amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.
C-3 NOVEL TRITERPENONE WITH C-28 AMIDE DERIVATIVES AS HIV INHIBITORS
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, (2018/09/12)
The invention relates to C-3 novel triterpenone with C-28 amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases (formula 1).
C-3 NOVEL TRITERPENONE WITH C-28 UREA DERIVATIVES AS HIV INHIBITORS
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, (2017/05/02)
The present invention relates to C-3 novel triterpenone with C-28 urea derivatives of formula (I); or pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable hydrates, tautomers, stereoisomers, prodrugs, compositions or combination thereof, wherein R1, R2, R3, W, J and X are as defined herein. The present invention also relates to pharmaceutical compositions comprising compounds of formula (I) useful for the treatment of viral diseases and particularly HIV mediated diseases.
Discovery of a novel and potent class of anti-HIV-1 maturation inhibitors with improved virology profile against gag polymorphisms
Tang, Jun,Jones, Stacey A.,Jeffrey, Jerry L.,Miranda, Sonia R.,Galardi, Cristin M.,Irlbeck, David M.,Brown, Kevin W.,McDanal, Charlene B.,Johns, Brian A.
, p. 2689 - 2694 (2017/05/29)
A new class of betulin-derived α-keto amides was identified as HIV-1 maturation inhibitors. Through lead optimization, GSK8999 was identified with IC50 values of 17?nM, 23?nM, 25?nM, and 8?nM for wild type, Q369H, V370A, and T371A respectively. When tested in a panel of 62 HIV-1 isolates covering a diversity of CA-SP1 genotypes including A, AE, B, C, and G using a PBMC based assay, GSK8999 was potent against 57 of 62 isolates demonstrating an improvement over the first generation maturation inhibitor BVM. The data disclosed here also demonstrated that the new α-keto amide GSK8999 has a mechanism of action consistent with inhibition of the proteolytic cleavage of CA-SP1.
C-3 NOVEL TRITERPENONE DERIVATIVES AS HIV INHIBITORS
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, (2017/07/31)
The present invention relates to C-3 novel triterpenone derivatives of formula (I); (I) or pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable hydrates, tautomers, stereoisomers, prodrugs, compositions or combination thereof, wherein R1, R2, R3, R4, R5, R6, R7, W, ?m ? and ?n ? are as defined herein. The present invention also relates to pharmaceutical compositions comprising compounds of formula (I) and process for preparing them, and their use for the treatment of viral diseases and particularly HIV mediated diseases.
C-3 NOVEL TRITERPENONE WITH C-28 REVERSE AMIDE DERIVATIVES AS HIV INHIBITORS
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, (2016/11/21)
Formula (I) The invention relates to C-3 novel triterpenone with C-28 reverse amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.
