- Development of an Improved Route to a Human Immunodeficiency Virus Maturation Inhibitor by Chromium-Free Allylic Oxidation and an Efficient Asymmetric Henry Reaction
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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.
- Herkommer, Daniel,Hunter, Sarah,Lynn, Sean M.,Manley, David,Rushworth, Philip,Slater, Fiona,Strachan, John B.,Woods, Martin
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p. 288 - 298
(2022/02/17)
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- C-3 NOVEL TRITERPENONE WITH C-28 HETEROCYCLE DERIVATIVES AS HIV INHIBITORS
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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.
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Page/Page column 28
(2018/03/06)
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- C-3 NOVEL TRITERPENONE WITH C-28 AMIDE DERIVATIVES AS HIV INHIBITORS
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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).
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Paragraph 0200; 0201
(2018/09/12)
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- C-3 NOVEL TRITERPENONE WITH C-17 N-AMIDE DERIVATIVES AS HIV INHIBITORS
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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.
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Page/Page column 27; 28
(2018/03/06)
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- C-3 NOVEL TRITERPENONE WITH C-28 DIAMIDE DERIVATIVES AS HIV INHIBITORS
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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.
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Page/Page column 24
(2018/03/28)
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- C-3 NOVEL TRITERPENONE WITH C-17 REVERSE AMIDE DERIVATIVES AS HIV INHIBITORS
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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.
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Page/Page column 30
(2018/03/06)
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- C-3 NOVEL TRITERPENONE DERIVATIVES AS HIV INHIBITORS
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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.
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Page/Page column 36
(2017/07/31)
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- C-3 NOVEL TRITERPENONE WITH C-28 UREA DERIVATIVES AS HIV INHIBITORS
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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.
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Page/Page column 25; 26
(2017/05/02)
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- Discovery of a novel and potent class of anti-HIV-1 maturation inhibitors with improved virology profile against gag polymorphisms
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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.
- 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.
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p. 2689 - 2694
(2017/05/29)
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- C-3 NOVEL TRITERPENONE WITH C-28 REVERSE AMIDE DERIVATIVES AS HIV INHIBITORS
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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.
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Page/Page column 35; 36
(2016/11/21)
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- LUPANE TRITERPENOID DERIVATIVES AND PHARMACEUTICAL USE THEREOF
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The present invention relates to a lupane triterpenoid derivatives and pharmaceutical use thereof, specifically relates to a lupane triterpenoid derivatives of formula (I)?(III), a pharmaceutical composition and a combination preparation comprising a lupane triterpenoid derivatives or a pharmaceutically acceptable salt thereof in a therapeutically-effective dose, particularly relates to the use in preparation of a medicament for the treatment of HIV-1/AIDS.
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Paragraph 0142; 0146; 0147
(2015/02/18)
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- LUPANE TRITERPENOID DERIVATIVES AND PHARMACEUTICAL USE THEREOF
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Disclosed are lupane triterpenoid derivatives and pharmaceutical use thereof, specifically lupane triterpenoid derivatives of formulae (I)~(III), a pharmaceutical composition and a combination preparation comprising said lupane triterpenoid derivatives or a pharmaceutically acceptable salt thereof in a therapeutically-effective dose, particularly the use in preparation of a medicament for the treatment of HIV-1/AIDS.
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Page/Page column 25; 26
(2013/08/28)
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- CARBONYL DERIVATIVES OF BETULIN
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Disclosed are a compound characterized by the following formula I or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising said compound or a pharmaceutically acceptable salt thereof, wherein R3, L, and A are as described in the application. Said compounds are useful for the treatment of HIV.
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Paragraph 00105
(2013/03/26)
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- PROPENOATE DERIVATIVES OF BETULIN
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The present invention relates to a compound characterized by the following Formula I or a pharmaceutically acceptable salt thereof, wherein X, Y, and Z are as described herein. Compounds of the present invention are useful for the treatment of HIV.
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Paragraph 00103
(2013/07/05)
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- PROPENOATE DERIVATIVES OF BETULIN
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The present invention relates to a compound characterized by Formula (I); or a pharmaceutically acceptable salt thereof, wherein X, Y, and Z are as described herein. Compounds of the present invention are useful for the treatment of HIV.
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Paragraph 00101; 00104
(2013/07/05)
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- DERIVATIVES OF BETULIN
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The present invention relates to compounds characterized by having a structure according to the following Formula I: (I), or a pharmaceutically acceptable salt thereof. Compounds of the present invention are useful for the treatment or prevention of HIV.
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Paragraph 000192; 00195
(2013/07/05)
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- NOVEL C-21-KETO LUPANE DERIVATIVES PREPARATION AND USE THEREOF
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The invention relates to 21-keto triterpene compounds of formula (I): wherein R1, X and Y are as defined herein, and pharmaceutically acceptable salts and solvates thereof. These compounds exhibit significant anti-HIV activity. Thus, the invention also relates to methods for prevention or treatment of HIV infections by administering therapeutically effective amounts of a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof to a subject in need of such treatment.
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Page/Page column 14
(2011/04/19)
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- NOVEL LUPANE DERIVATIVES
-
The invention relates to 21-keto triterpene compounds of formula (I): wherein R1, X, and Y are as defined herein, and pharmaceutically acceptable salts and solvates thereof. These compounds exhibit significant anti-HIV activity. Thus, the invention also relates to methods for prevention or treatment of HIV infections by administering therapeutically effective amounts of a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof to a subject in need of such treatment.
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Page/Page column 16; 17
(2011/04/19)
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- DERIVATIVES OF BETULIN
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The present invention relates to a compound characterized by Formula I or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, X, and Y are as described herein. Compounds of the present invention are useful for the treatment of HIV-1.
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Page/Page column 9
(2011/09/15)
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- NOVEL C-21-KETO LUPANE DERIVATIVES PREPARATION AND USE THEREOF
-
The invention relates to 21 -keto triterpene compounds of formula (I): wherein R1, X and Y are as defined herein, and pharmaceutically acceptable salts and solvates thereof. These compounds exhibit significant anti-HIV activity. Thus, the invention also relates to methods for prevention or treatment of HIV infections by administering therapeutically effective amounts of a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof to a subject in need of such treatment.
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Page/Page column 37; 38
(2009/08/14)
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- NOVEL LUPANE DERIVATIVES
-
The invention relates to 21-keto triterpene compounds of formula (I): wherein R1, X, and Y are as defined herein, and pharmaceutically acceptable salts and solvates thereof. These compounds exhibit significant anti-HIV activity. Thus, the invention also relates to methods for prevention or treatment of HIV infections by administering therapeutically effective amounts of a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof to a subject in need of such treatment.
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Page/Page column 52; 53
(2009/08/14)
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- Reaction of 18β,19β-epoxylupan-21-one derivatives with acids: A way to 21,22-disubstituted lup-18-ene triterpenoids
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Depending on the conditions and the acid employed, 18β,19β-epoxy-28-hydroxy-21-oxolupan-3β-yl acetate (2a) and 18β,19β-epoxy-21-oxolupane-3β,28-diyl diacetate (2b) on treatment with acid gave three types of products: (i) 28-nor derivatives: 21-oxo28-norlu
- Klinotova, Eva,Cermakova, Jitka,Rejzek, Martin,Krecek, Vaclav,Sejbal, Jan,Olsovsky, Petr,Klinot, Jiri
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p. 329 - 347
(2007/10/03)
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- FUNCTIONALIZATION OF 3β,28-LUPANEDIOL DIACETATE WITH CHROMIUM(VI) OXIDE
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The oxidation of 3β,28-lupanediol diacetate (I) with chromium (VI) oxide gives low yields of products with functional groups in the ring E as products of hydroxylation at the 19β position (IV, VI, and IX) and the 11-ketone VII which has been transformed into other lupane derivatives with an oxygen functional group at 11 position (VIII, XIII - XV) or with a 9(11)-double bond (XVI, XVII).Structure of the compounds prepared has been verified by their 1H and 13C NMR spectra as well as by their mass spectra.
- Sejbal, Jan,Klinot, Jiri,Budesinsky, Milos,Protiva, Jiri
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p. 2936 - 2949
(2007/10/02)
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