137622-85-6

Upstream product

• 93-10-7 quinoline-2-carboxylic acid 
• 137431-06-2 2-[3(S)-[(L-asparaginyl)-amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 136465-98-0 (2S)-2-[(quinoline-2-carbonyl)-amino]-succinamic acid 
• 136522-17-3 cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 136465-99-1 2,5-dioxopyrrolidin-1-ylquinoline-2-carboxylate 
• 63-91-2 L-phenylalanine 
• 128019-40-9 (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide 
• 162221-36-5 (4S,5S)-4-benzyl-2-oxo-oxazolidine-5-carboxylic acid methyl ether 
• 136465-80-0 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane 
• 136465-82-2 1-Hydroxy-4-phenyl-3(S)-phthalimido-2-butanone 
• 136465-78-6 N-tert-Butyldecahydro-2-(2(R)-hydroxy-4-phenyl-3(S)phthalimidobutyl)-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 136522-18-4 2-<3(S)-<amino>-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 162221-28-5 4-Nitro-benzenesulfonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester 
• 178680-13-2 [(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid methyl ester 

Downstream Products

• 149845-06-7 invirase 

Relevant academic research and scientific papers

NOVEL POLYMORPHS OF SAQUINAVIR

The present invention provides novel polymorphs of saquinavir, processes for their preparation and pharmaceutical compositions comprising them. The present invention also provides a process for purification of saquinavir. The present invention further provides a novel process for preparation of known saquinavir crystalline form I.

NOVEL POLYMORPHS OF SAQUINAVIR

The present invention provides novel polymorphs of saquinavir, processes for their preparation and pharmaceutical compositions comprising them. The present invention also provides a process for purification of saquinavir. The present invention further provides a novel process for preparation of known saquinavir crystalline form I.

Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir

A general enantioselective synthesis of new syn-hydroxyethylamine isosteres has been developed. The approach, based on the controlled opening of functionalized optically active 2,3-epoxy amines, can be conveniently used for the preparation of new peptidom

A PROCESS FOR THE PREPARATION OF SAQUINAVIR USING NOVEL INTERMEDIATE

The present invention provides a commercially viable process for preparing saquinavir and pharmaceutically acceptable acid addition salts thereof using novel intermediate. Thus, for example, N?2?-(2-quinolinylcarbonyl)-L-asparagine is reacted with pivaloyl chloride in methylene chloride in presence of triethyl amine to give pivaloyl N?2?-(2-quinolinylcarbonyl)-L-asparaginate, which is then condensed with [3S,4aS,8aS]-2-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-(1,1-dimethylethyl)decahydro-3-isoquinoline carboxamide to give saquinavir, followed by treatment with methanesulfonic acid to give saquinavir mesylate.

Oral dosage forms of water insoluble drugs and methods of making the same

A method of making an oral dosage form of a water insoluble drug such as Saquinavir or Cyclosporine or Paclitaxel is carried out by: (a) providing a single phase working Solution comprising or consisting essentially of an active agent, water, a water-soluble polymer, and a solvent, said solvent selected from the group consisting of alcohol, acetone, and mixtures thereof; and may or may not contain a surfactant and pH of the said working solution may or may not be adjusted (b) providing particles formed from a pharmaceutically acceptable core material; (c) combining, preferably by spraying, said working solution with said particles to produce active agent-coated particles; such drug loaded particles may contain an external coat (d) drying said active agent-coated particles; and (e) forming said dried particles into an oral dosage form. Dried particles produced by the process, oral dosage forms containing such particles, and methods of treatment therewith are also described.

Synthesis of the HIV-proteinase inhibitor Saquinavir: A challenge for process research

The task of process research, namely developing efficient, economically and technically as well as ecologically feasible syntheses in time, is demonstrated on the HIV-proteinase inhibitor Saquinavir (1), a complex molecule comprising six stereo-centres. Based on the first 26-step research synthesis furnishing a 10% overall yield, process research established a new, short 11-step synthesis affording a 50% overall yield.

Studies toward the Large-Scale Synthesis of the HIV Proteinase Inhibitor Ro 31-8959

Ro 31-8959 (1), a potent and selective inhibitor of HIV proteinase, is currently in phase III clinical trials.Six approaches for the large-scale synthesis of this compound have been studied.All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5.They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and develop chirality from L-phenylalanine, dimethyl D-tartrate, or a Sharpless epoxidation.The preferred route starts from N-phthaloyl-L-phenylalaninyl chloride and uses tris((trimethylsilyl)oxy)ethene to effect homologation to hydroxy ketone 30, which is elaborated in a five-step two-pot procedure to N-phthaloyl epoxide 33 and hence 1.Kilogram quantities of Ro 31-8959 have been prepared using this route.