136465-89-9Relevant academic research and scientific papers
PROCESS FOR SYNTHESIS OF SYN AZIDO EPOXIDE AND ITS USE AS INTERMEDIATE FOR THE SYNTHESIS OF AMPRENAVIR and SAQUINAVIR
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Paragraph 0080-0081, (2015/02/18)
Disclosed herein is a novel route of synthesis of syn azide epoxide of formula 5, which is used as a common intermediate for asymmetric synthesis of HIV protease inhibitors such as Amprenavir, Fosamprenavir, Saquinavir and formal synthesis of Darunavir an
A PROCESS FOR SYNTHESIS OF SYN AZIDO EPOXIDE AND ITS USE AS INTERMEDIATE THE SYNTHESIS OF AMPRENAVIR and SAQUINAVIR
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Page/Page column 22, (2013/07/25)
Disclosed herein is a novel route of synthesis of syn azide epoxide of formu 5, which is used as a common intermdeiate for asymmetric synthesis of HIV protease inhibitors such as Amprenavir, Fosamprenavir, Saquinavir and formal synthesis of Darunavir and
Enantioselective synthesis of HIV protease inhibitor amprenavir via Co-catalyzed HKR of 2-(1-azido-2-phenylethyl)oxirane
Gadakh, Sunita K.,Santhosh Reddy,Sudalai, Arumugam
, p. 898 - 903 (2012/09/22)
A short and efficient enantioselective synthesis of the HIV protease inhibitor amprenavir 1 (99% ee) as well as a formal synthesis of saquinavir 3 have been achieved in high enantiomeric purity starting from commercially available materials. Our strategy mainly comprises a Co-catalyzed two-stereocentred hydrolytic kinetic resolution (HKR) of racemic 2-(1-azido-2-phenylethyl)oxirane as the chirality inducing step. Also presented is a concise synthesis of (S)-3-hydroxytetrahydrofuran 4, the key structural feature, in high enantiomeric purity (98% ee).
A simple and inexpensive procedure for low valent copper mediated benzylation of aldehydes in wet medium
Dubey, Akhil Kr.,Goswami, Dibakar,Chattopadhyay, Angshuman
experimental part, p. 137 - 145 (2010/10/02)
An operationally simple, inexpensive and efficient procedure for benzylation of aldehydes in wet medium has been developed that was mediated with low valent copper, prepared in situ through spontaneous reduction of CuCl 2-2H2O with magnesium in situ. Notably, copper mediated benzylation of 3h took place with good syn selectivity that was opposite to that for the corresponding Grignard addition. Finally, homobenzyl alcohol 5a was elegantly transformed into a known protease inhibitor synthon I. ARKAT USA, Inc.
FITNESS ASSAY AND ASSOCIATED METHODS
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Page/Page column 17, (2010/11/30)
The present invention provides an assay for determining the biochemical fitness of a biochemical species in a mutant replicating biological entity relative to its predecessor. The present invention further provides a continuous fluorogenic assay for measuring the anti-HIV protease activity of protease inhibitor. The present invention also provides a method of administering a therapeutic compound that reduces the chances of the emergence of drug resistance in therapy. The present invention also provides a compound of formula (I) or a pharmaceutically acceptable salt, a prodrug, a composition, or an ester thereof, wherein A is a group of formulas (A), (B), (C) or (D); R1, R2, R3, R5 or R6 is H, or an optionally substituted and/or heteroatom-bearing alkyl, alkenyl, alkynyl, or cyclic group; Y and/or Z are CH2, O, S, SO, SO2, amino, amides, carbamates, ureas, or thiocarbonyl derivatives thereof, optionally substituted with an alkyl, alkenyl, or alkynyl group; n is from 1 to 5; X is a bond, an optionally substituted methylene or ethylene, an amino, O or S; Q is C(O), C(S), or SO2; m is from 0 to 6; R4 is OH, ═O (keto), NH2, or alkylamino, including esters, amides, and salts thereof; and W is C(O), C(S), S(O), or SO2. Optionally, R5 and R6, together with the N—W bond of formula (I), comprise a macrocyclic ring.
NOVEL GAMMA-LACTAMS AS BETA-SECRETASE INHIBITORS
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Page 52-53, (2008/06/13)
There is provided a series of novel substituted gamma-lactams of Formula (I) wherein R1, R2, R3, R4 and R5 are defined herein, their pharmaceutical compositions and methods of use. These novel compounds inhibit the processing of amyloid precursor protein (APP) by β-secretase and, more specifically, inhibit the production of aβ-peptide. The present invention is directed to compounds useful in the treatment of neurological disorders related to β-amyloid production, such as Alzheimer's disease and other conditions affected by anti-amyloid activity.
Synthesis of conformationally restricted mimetics of γ-turns and incorporation into desmopressin, an analogue of the peptide hormone vasopressin
Brickmann, Kay,Yuan, ZhongQing,Sethson, Ingmar,Somfai, Peter,Kihlberg, Jan
, p. 2241 - 2253 (2007/10/03)
Mimetics of tripeptides adopting inverse and classical γ-turn conformations have been designed and synthesized by an enantioselective approach and then incorporated in an analogue of the hormone vasopressin. In the mimetics one of the amide bonds of the γ
A Concise, General Enantioselective Synthetic Route to 2(R)- and 2(S)-oxirane and Related Epoxides
Bennett, Frank,Girijavallabhan, Viyyoor M.,Patel, Naginbhai
, p. 737 - 738 (2007/10/02)
The title oxiranes were constructed in >95percent enantiomeric excess (e.e.) utilizing a Sharpless asymmetric epoxidation followed by regioselective azide displacement with i)2(N3)2> as the key steps.
Potent HIV Protease Inhibitors: The Development of Tetrahydrofuranylglycines as Novel P2 Ligands and Pyrazine Amides as P3-Ligands
Ghosh, Arun K.,Thompson, Wayne J.,Holloway, M. Katharine,McKee, Sean P.,Duong, Tien T.,et al.
, p. 2300 - 2310 (2007/10/02)
A series of protease inhibitors bearing constrained unnaturel amino acids at the P2-position and novel heterocycles at the P3-position of compound 1 (Ro 31-8959) were synthesized, and their in vitro enzyme inhibitory and antiviral ac
