857904-02-0Relevant articles and documents
Method for synthesis of atazanavir
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Paragraph 0045; 0046; 0048, (2018/04/01)
The invention discloses a method for synthesis of atazanavir. The method comprises that a compound methyl (S)-1-((S)-2-ethoxyethyl-1-phenylethane-2-yl-amino)-3, 3-dimethyl-1-carbonylbutane-2-yl-carbamate shown in the formula V and a compound N-1-[N-(methoxycarbonyl)-L-tertiary leucine]-N-2-[4-(2-pyridyl)-benzyl]hydrazine shown in the formula VIII undergo a nucleophilic substitution reaction in anorganic solvent to produce a compound 1-[4-(2-pyridyl)phenyl]-5(S)-2, 5-bis{[N-(methoxycarbonyl)-L-tertiary leucine]amino}-4(S)-hydroxy-6-phenyl-2-azahexane VIII shown in the formula IX, wherein the compound shown in the formula IX is atazanavir. The method utilizes raw materials having a wide raw material source, the product is easy to purify, a cost is low, the synthesis processes are simple, the operation is simple, the process is simple, special requirement on equipment is avoided and large-scale production feasibility is realized.
PROTEASE INHIBITORS HAVING ENHANCED FEATURES
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, (2017/02/28)
Provided herein (among other things) are protease inhibitor compounds having enhanced features, along with methods for administering such compounds. For example, the subject compounds can be administered without concomitant administration of a CYP3A4 inhibitor, have increased therapeutic index and/or increased potency, and are low-resistance inducing in nature.
Synthesis of P1′-functionalized macrocyclic transition-state mimicking HIV-1 protease inhibitors encompassing a tertiary alcohol
De Rosa, Maria,Unge, Johan,Motwani, Hitesh V.,Rosenquist, ?sa,Vrang, Lotta,Wallberg, Hans,Larhed, Mats
, p. 6444 - 6457 (2014/10/15)
Seven novel tertiary alcohol containing linear HIV-1 protease inhibitors (PIs), decorated at the para position of the benzyl group in the P1′ side with (hetero)aromatic moieties, were synthesized and biologically evaluated. To study the inhibition and antiviral activity effect of P1-P3 macrocyclization, 14-and 15-membered macrocyclic PIs were prepared by ring-closing metathesis of the corresponding linear PIs. The macrocycles were more active than the linear precursors and compound 10f, with a 2-thiazolyl group in the P1′ position, was the most potent PI of this new series (Ki 2.2 nM, EC 50 0.2 μM). Co-crystallized complexes of both linear and macrocyclic PIs with the HIV-1 protease enzyme were prepared and analyzed.
NOVEL AZA-PEPTIDES CONTAINING 2,2-DISUBSTITUTED CYCLOBUTYL AND/OR SUBSTITUTED ALKOXY BENZYL DERIVATIVES AS ANTIVIRALS
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, (2011/07/30)
The present invention relates to novel aza-peptides containing 2,2-disubstituted 5 cyclobutyl and/or substituted alkoxy benzyl derivatives of formula (I) and compositions for inhibiting Human Immunodeficiency Virus (HIV) and process for making the compounds.
Process for Synthesizing Atazanavir
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Page/Page column 19, (2009/10/31)
This invention relates to a process for synthesizing Atazanvir, including novel intermediates and novel steps to various intermediates along the synthetic pathway.
PROCESS FOR SYNTHESIZING ATAZANAVIR
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Page/Page column 41-42; 34, (2009/12/05)
This invention relates to a process for synthesizing Atazanavir, Formula (I), including novel intermediates and novel steps to various intermediates along the synthetic pathway.
An efficient and practical synthesis of the HIV protease inhibitor atazanavir via a highly diastereoselective reduction approach
Fan, Xing,Song, Yan-Li,Long, Ya-Qiu
, p. 69 - 75 (2012/12/31)
An efficient and practical synthesis of the HIV-1 protease inhibitor Atazanavir was developed by employing the diastereoselective reduction of ketomethylene aza-dipeptide isostere 10 as the key and final step. The high diastereoselectivity of the amino ketone reduction by lithium tri-iert-butoxyaluminum hydride in diethyl ether to afford the desired svn-1,2-amino alcohol structure was achieved by Felkin- Anh control as a result of the bulky and chiral N-(methoxycarbonyl)-L-tert-leucinyl moiety as the nitrogen protecting group. The coupling of the two key intermediates, N-(methoxycarbonyl)-L-tert-leucine acylated benzyl hydrazine 7 and chloromethyl ketone 9, via an SN2 reaction furnished the amino ketone 10 in high yield under our optimized conditions. Our new methodology features the late introduction of the S-hydroxyl group and the early acylation of benzyl hydrazine and chloromethyl ketone with N-(methoxycarbonyl)-L-tert-leucine, respectively, which confers high efficiency and easy purification.
Two-carbon-elongated HIV-1 protease inhibitors with a tertiary-alcohol- containing transition-state mimic
Wu, Xiongyu,?hrngren, Per,Ekegren, Jenny K.,Unge, Johan,Unge, Torsten,Wallberg, Hans,Samuelsson, Bertil,Hallberg, Anders,Larhed, Mats
, p. 1053 - 1057 (2008/09/20)
A new generation of HIV-1 protease inhibitors encompassing a tertiary-alcohol-based transition-state mimic has been developed. By elongation of the core structure of recently reported inhibitors with two carbon atoms and by varying the P1′ group of the co
ANTIVIRAL PROTEASE INHIBITORS
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Page/Page column 454; 510-511, (2008/06/13)
The invention is related to compounds of Formula I or a pharmaceutically acceptable salt, solvate, ester, and /or phosphonate thereof, compositions containing such compounds, and therapeutic methods that include the administration of such compounds.
A facile and efficient synthesis of d3-labelled Reyataz
Zhang, Huiping,Bonacorsi Jr., Samuel J.,Chen, Bang-Chi,Leith, Leslie W.,Rinehart, J. Kent,Balasubramanian, Balu,Barrish, Joel C.
, p. 1041 - 1047 (2007/10/03)
A facile and efficient synthesis of d3-labelled Reyataz is described. The key step of synthesis involved the coupling of N-(d 3-methoxycarbonyl)-L-tert-leucine 2b with an advanced chiral non-racemic building block 4. The latter was synthesized in 4 steps from the readily accessible hydrazine derivative 8. Copyright
