cas 206361-99-1, Darunavir | Articles data

Articles about 206361-99-1Total 30 be found

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The Chiron Approach to (3 R,3 aS,6 aR)-Hexahydrofuro[2,3- b]furan-3-ol, a Key Subunit of HIV-1 Protease Inhibitor Drug, Darunavir
We describe an enantioselective synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol which is a key subunit of darunavir, a widely used HIV-1 protease inhibitor drug for the treatment of HIV/AIDS patients. The synthesis was achieved in optically pure form utilizing commercially available sugar derivatives as the starting material. The key steps involve a highly stereoselective substrate-controlled hydrogenation, a Lewis acid catalyzed anomeric reduction of a 1,2-O-isopropylidene-protected glycofuranoside, and a Baeyer-Villiger oxidation of a tetrahydrofuranyl-2-aldehyde derivative. This optically active ligand alcohol was converted to darunavir efficiently.
Ghosh, Arun K.,Markad, Shivaji B.,Robinson, William L.
p. 1216 - 1222
(2020/12/22)

An improved and robust scale-up process aided with identification and control of critical process impurities in darunavir ethanolate
A robust and safe industrial process, including five isolations and drying steps for widely prescribed anti-HIV (protease inhibitor) drug darunavir ethanolate 2, has been developed. A salient feature of this process is the development of procedures enabling the efficient synthesis of multi-kilogram quantity of darunavir ethanolate, and process demonstrations through plant scale preparation are offered where darunavir molecule has been prepared with overall > 70% chemical yield and > 99.8% purity without involving any purification procedure(s), with all possible process impurities below than the desired limit (not more than 0.08%) were isolated, synthesized and characterized. The developed process is entirely robust, very efficient and demonstrated up to kilograms scale.
Girigani, Sathyanarayana,Singh, Harnam,Kola, Sankar Rao,Dayanand Yelmeli, Vijayalaxmi,Regula, Venu Gopal,Shah, Sakshi,Jain, Neelu,Kumar, Pramod
p. 267 - 281
(2019/08/26)

A NOVEL PROCESS FOR THE PREPARATION OF HIV PROTEASE INHIBITOR AND INTERMEDIATES THEREOF
The present invention relates to process for the preparation of Darunavir or a solvate thereof of Formula (I) using a novel intermediate (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2S,3R)-4-(4-(1,3-dioxoisoindolin-2-yl)-N-isobutylphenylsulfonamido)-3 -hydroxy- 1 -phenylbutan-2- ylcarbamate Compound of formula (II): The present invention also relates to the process for the preparation of novel intermediates (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2S,3R)-4-(4-(l,3-dioxo iso indolin-2-yl)-N-isobutylphenylsulfonamido)-3 -hydroxy-1-phenylbutan-2-ylcarbamate Compound of formula (II). Darunavir or its solvate of formula (I) are useful therapeutic agent and used in treatment of antiviral diseases.
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(2018/02/16)

A SIMPLIFIED PROCEDURE FOR THE PREPARATION OF DARUNAVIR
The present invention relates to an improved process for preparing [(1S,2R)-3-[[(4-aminophenyl)-sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)-propyl]-carbamic acid (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester – which compound is also kno
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Page/Page column 10

(2018/06/06)

Practical synthesis of the bicyclic darunavir side chain: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol from monopotassium isocitrate
A practical synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol?a key intermediate in the synthesis of darunavir?from monopotassium isocitrate is described. The isocitric acid salt, obtained from a high-yielding fermentation fed by sunflower oil, was converted in several steps to a tertiary amide. This amide, along with the compound's ester functionalities, was reduced with lithium aluminum hydride to give, on acidic workup, a transient aminal-triol. This was converted in situ to the title compound, the bicyclic acetal furofuranol side chain of darunavir, a protease inhibitor used in treatment of HIV/AIDS. Key to the success of this process was identifying an optimal amide that allowed for complete reaction and successful product isolation. N-Methyl aniline amide was identified as the most suitable substrate for the reduction and the subsequent cyclization to the desired product. Thus, the side chain is produced in 55% overall yield from monopotassium isocitrate.
Moore, Gary L.,Stringham, Rodger W.,Teager, David S.,Yue, Tai-Yuen
p. 98 - 106
(2017/11/30)

PROCESS FOR THE PREPARATION OF DARUNAVIR
The present invention provides a cost effective and industrially feasible process for preparation of Darunavir (I). Also described is the novel salt of intermediate 4-Amino-N- ((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzene sulfonamide acid salt (VIII) and its use in the preparation of Darunavir. Formula (I) and (VII).
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(2016/12/22)

A Concise One-Pot Organo- and Biocatalyzed Preparation of Enantiopure Hexahydrofuro[2,3-b]furan-3-ol: An Approach to the Synthesis of HIV Protease Inhibitors
A simple and efficient one-pot synthesis of enantiopure hexahydrofuro[2,3-b]furan-3-ol, a crucial component of HIV-1 protease inhibitors, was developed. The one-pot process involves an organocatalytic condensation followed by an enzymatic optical resolution. The condensation of 1,2-dihydrofuran and glycolaldehyde was achieved using Schreiner's thiourea catalyst (1 mol-%). A subsequent lipase-catalyzed kinetic resolution gave the target alcohol with >99 % ee. To demonstrate the practicality of this method, Darunavir, an HIV-1 protease inhibitor used to treat multi-drug-resistant HIV, was synthesized.
Kanemitsu, Takuya,Inoue, Mizuho,Yoshimura, Nono,Yoneyama, Kazutoshi,Watarai, Rie,Miyazaki, Michiko,Odanaka, Yuki,Nagata, Kazuhiro,Itoh, Takashi
p. 1874 - 1880
(2016/05/09)

PROCESS FOR THE PREPARATION OF [(1 S,2R)-3-[[(4-AMINOPHENYL)SULFONYL] (2-METHYLPROPYL)AMINO]-2-HYDROXY-1 -(PHENYLMETHYL)PROPYL]-CARBAMIC ACID (3R,3AS,6AR)HEXAHYDRO FURO[2,3-B]FURAN-3-YL ESTER AND ITS AMORPHOUS FORM
The present invention relates to an improved process for the preparation of [(1 S,2R)-3-[ [(4-aminophenyl)sulfonyl] (2-methylpropyl)amino]-2-hydroxy- 1 -(phenylmethyl)propyl] - carbamic acid (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl ester compound of formula- 1 represented by the following structural formula:
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(2017/04/21)

Process for preparation of Darunavir
Provided are a process for preparation of darunavir or solvates or a pharmaceutically acceptable salt thereof substantially free of bisfuranyl impurities and a process for preparation of amorphous darunavir using the darunavir propionate solvate.
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(2016/11/14)

PROCESS FOR PREPARATION OF DARUNAVIR
Provided are a process for preparation of darunavir or solvates or a pharmaceutically acceptable salt thereof substantially free of bisfuranyl impurities and a process for preparation of amorphous darunavir using the darunavir propionate solvate.
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Paragraph 0174; 0175; 0176; 0177; 0178

(2015/07/27)

NOVEL SOLVATES OF DARUNAVIR
The present invention relates to novel solvates of Darunavir of Formula I.
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(2015/05/26)

Crystalline Darunavir
The present invention relates to a non-solvated crystalline Darunavir, process for its preparation and pharmaceutical composition comprising it. The present invention also relates to a process for the preparation of amorphous Darunavir from a non-solvated crystalline Darunavir.
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(2014/12/09)

CRYSTALLINE DARUNAVIR
The present invention relates to a non-solvated crystalline Darunavir, process for its preparation and pharmaceutical composition comprising it. The present invention also relates to a process for the preparation of amorphous Darunavir from a non-solvated crystalline Darunavir.
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(2013/08/15)

NOVEL SOLVATES OF DARUNAVIR
The present invention relates to novel solvates of Darunavir of Formula (I).
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Page/Page column 18

(2013/07/31)

Liquid chromatographic separation of darunavir enantiomers on coated and immobilized amylose tris(3, 5-dimethylphenylcarbamate) chiral stationary phases
Liquid chromatographic separation of darunavir enantiomers on covalently bonded and physically adsorbed polysaccharide chiral stationary phases was studied at different temperatures. The separations were accomplished under normal-phase conditions by using
Rao, Ramisetti Nageswara,Kumar, Kandukuri Nagesh,Naidu, Challa Gangu
experimental part
p. 652 - 660
(2012/10/18)

First stereoselective total synthesis of (3R, 3aS, 6aR)-hexahydrofuro[2,3- b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutyl phenylsulfonamido)-3-hydroxy-1- phenylbutan-2-yl-carbamate (diastereomer of Darunavir)
The stereoselective novel synthesis of (3R,3aS,6aR)-hexahydrofuro [2,3-b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutyl phenyl sulfonamido)-3-hydroxy-1- phenylbutan-2-yl-carbamate, has been accomplished in situ from the intermediate 4- amino-N-((2S,3R)-3-amino-
Babu, Kilaru Ravendra,Rao, Valasani Koteswara,Sudhakar, Yellapu,Raju, Chamarthi Naga
p. 849 - 854
(2012/09/21)

PROCESS FOR THE PREPARATION OF DARUNAVIR
A process for the preparation of Darunavir comprises the reacting of 4-amino-N-(2R,3S) (3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide with (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol derivative in N-methyl-2-pyrrolidinone and isolating the resulting Darunavir. The process yields Darunavir with a very low level of the difuranyl impurity.
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(2012/10/08)

NOVEL PROCESS FOR PREPARATION OF DARUNAVIR AND DARUNAVIR ETHANOLATE OF FINE PARTICLE SIZE
The present invention provides a novel process for preparation of darunavir that involves reduction of [(1S,2R)-3-[[(4-nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy -1-(phenylmethyl)propyl]carbamic acid (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester, of formula (5). The present invention also provides darunavir ethanolate of particle size wherein d0.9 is less than 130 μm, d0.5 is less than 30 μm, d0.1 is less than 10 μm and process for its preparation.
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Page/Page column 5

(2012/09/25)

PROCESS FOR THE PREPARATION OF DARUNAVIR AND DARUNAVIR INTERMEDIATES
The present invention relates to a process for the preparation of darunavir, a nonpeptide protease inhibitor (PI), useful for the treatment of HIV/AIDS patients harboring multidrug-resistant HIV-1 variants that do not respond to previously existing HAART regimens. The present invention further relates to processes for the stereo-directed preparation of darunavir intermediates, in particular (3R,3aS,6aR)-hexahydrofuro [2,3-b] furan-3-ol and to certain novel intermediates obtained by such processes.
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(2011/08/21)

AN IMPROVED PROCESS FOR THE PREPARATION OF DARUNAVIR
The present invention relates to the process for the preparation of Darunavir, solvates or pharmaceutically acceptable salts with improved yield and quality having the difuranyl impurity of formula (1) less than 0.1%. The present invention also relates to provide processes for the preparation of amorphous Darunavir. Further, the present invention also relates to pharmaceutical composition of crystalline or amorphous Darunavir, solvates or pharmaceutically acceptable salts having the difuranyl impurity of formula (1) less than 0.1%.
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(2011/05/06)

POLYMORPHS OF DARUNAVIR
The present invention provides novel solvated forms of darunavir and processes for there preparation. The present invention also provides novel process for preparation of darunavir amorphous form and pharmaceutical composition comprising it. Thus, for exa
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Page/Page column 5-6

(2011/07/07)

CRYSTALLINE HYDROCHLORIDE SALT OF DARUNAVIR
The present invention provides novel crystalline hydrochloride salt of darunavir, process for its preparation and to pharmaceutical composition comprising it. The present invention also provides novel process for preparation of darunavir amorphous form an
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Page/Page column 9

(2011/12/04)

DARUNAVIR POLYMORPH AND PROCESS FOR PREPARATION THEREOF
There is disclosed crystalline darunavir hydrate substantially free of any non-aqueous solvent.
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Page/Page column 6

(2011/08/03)

A NOVEL PROCESS FOR PREPARATION OF DARUNAVIR AND DARUNAVIR ETHANOLATE OF FINE PARTICLE SIZE
The present invention provides a novel process for preparation of darunavir that involves reduction of [(1S,2R)-3-[[(4-nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy -1-(phenylmethyl) propyl] carbamic acid (3R,3aS,6aR)-hexahydrofuro [2,3-b]furan-3-yl ester, of formula (5). The present invention also provides darunavir ethanolate of particle size wherein d0.9 is less than 130 μm, d0.5 is less than 30 μm, d0.1 is less than 10 μm and process for its preparation.
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Page/Page column 13

(2011/05/11)

PROCESS FOR THE PREPARATION OF (3R,3AS,6AR)-HEXAHYDROFURO [2,3-B] FURAN-3-YL (1S,2R)-3-[[(4-AMINOPHENYL) SULFONYL] (ISOBUTYL) AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE
The present invention relates to a process for the preparation of (3R,3a S,6aR)-hexa-hydrofuro [2,3-b] furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate as well as novel intermediates for use in said process. (3R,3a S,6aR)-hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate is particularly useful as an HIV protease inhibitor.
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Page/Page column 31-32

(2010/04/06)

METHOD AND COMPOSITIONS FOR TREATING HIV INFECTIONS
Described herein are compounds and compositions that are useful in the treatment of HIV, AIDS, and AIDS-related diseases. In addition, compounds are described herein that are capable of inhibiting the dimerization of HIV proteases.
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(2008/12/08)

PROCESS FOR THE PREPARATION OF (3R,3AS,6AR)-HEXAHYDROFURO [2,3-B] FURAN-3-YL (1S,2R)-3-[[(4-AMINOPHENYL) SULFONYL] (ISOBUTYL) AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE
The present invention relates to a process for the preparation of (3R,3aS,6aR)--hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate as well as intermediates for use in said process. More in particular the invention relates to processes for the preparation of (3R,3aS,6aR)-hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate which make use of 4-amino-N- ((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-(isobutyl)benzene sulfonamide intermediate, and to processes amenable to industrial scaling up. (3R,3aS,6aR)-hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate is particularly useful as HIV protease inhibitors.
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Page/Page column 27-28

(2008/06/13)

Discovery and selection of TMC114, a next generation HIV-1 protease inhibitor
The screening of known HIV-1 protease inhibitors against a panel of multi-drug-resistant viruses revealed the potent activity of TMC126 on drug-resistant mutants. In comparison to amprenavir, the improved affinity of TMC126 is largely the result of one extra hydrogen bond to the backbone of the protein in the P2 pocket. Modification of the substitution pattern on the phenylsulfonamide P2′ substituent of TMC126 created an interesting SAR, with the close analogue TMC114 being found to have a similar antiviral activity against the mutant and the wild-type viruses. X-ray and thermodynamic studies on both wild-type and mutant enzymes showed an extremely high enthalpy driven affinity of TMC114 for HIV-1 protease. In vitro selection of mutants resistant to TMC114 starting from wild-type virus proved to be extremely difficult; this was not the case for other close analogues. Therefore, the extra H-bond to the backbone in the P2 pocket cannot be the only explanation for the interesting antiviral profile of TMC114. Absorption studies in animals indicated that TMC114 has pharmacokinetic properties comparable to currently approved HIV-1 protease inhibitors.
Surleraux, Dominique L. N. G.,Tahri, Abdellah,Verschueren, Wim G.,Pille, Geert M. E.,De Kock, Herman A.,Jonckers, Tim H. M.,Peeters, Anik,De Meyer, Sandra,Azijn, Hilde,Pauwels, Rudi,De Bethune, Marie-Pierre,King, Nancy M.,Prabu-Jeyabalan, Moses,Schiffer, Celia A.,Wigerinck, Piet B. T. P.
p. 1813 - 1822
(2007/10/03)

Stereoselective photochemical 1,3-dioxolane addition to 5-alkoxymethyl-2(5H)-furanone: Synthesis of bis-tetrahydrofuranyl ligand for HIV protease inhibitor UIC-94017 (TMC-114)
A convenient synthesis of (3R,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan, a high-affinity non-peptidal ligand for HIV protease inhibitor UIC-94017, is described. This inhibitor is undergoing advanced clinical trials. The synthesis utilizes a novel stereoselective photochemical 1,3-dioxolane addition to 5(S)-benzyloxymethyl-2(5H)-furanone as the key step. The requisite furanone derivative was prepared in high enantiomeric excess by an immobilized lipase-catalyzed selective acylation of (±)-1-(benzyloxy)-3-buten-2-ol and a ring-closing olefin metathesis with Grubbs' catalyst. Optically active bis-THF was converted to protease inhibitor 2 (UIC-94017).
Ghosh, Arun K.,Leshchenko, Sofiya,Noetzel, Marcus
p. 7822 - 7829
(2007/10/03)

Potent HIV protease inhibitors incorporating high-affinity P2-ligands and (R)-(hydroxyethylamino)sulfonamide isostere
Design and synthesis of a series of very potent nonpeptide HIV protease inhibitors are described. The inhibitors are derived from novel high affinity P2-ligands and (R)-(hydroxyethylamino)sulfonamide isostere.
Ghosh, Arun K.,Kincaid, John F.,Cho, Wonhwa,Walters, D. Eric,Krishnan,Hussain, Khaja Azhar,Koo, Yumee,Cho, Hanna,Rudall, Clare,Holland, Louis,Buthod, Jim
p. 687 - 690
(2007/10/03)

Chemical Properties

Appearance/Colour :White amorphous solid
Melting Point: 74-76 °C
Density: 1.34 g/cm³
Solubility:Soluble in DMSO (>25 mg/ml)
Storage Temp.:-20°C Freezer
Refractive Index: 1.62
PKA: 11.43±0.46(Predicted)
PSA: 148.80000
LogP: 4.42820

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206361-99-1

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Chemical Properties

Appearance/Colour :White amorphous solid

Melting Point: 74-76 °C

Density: 1.34 g/cm³

Solubility:Soluble in DMSO (>25 mg/ml)

Storage Temp.:-20°C Freezer

Refractive Index: 1.62

PKA: 11.43±0.46(Predicted)

PSA: 148.80000

LogP: 4.42820

Global suppliers and manufacturers of 206361-99-1total 158 suppliers on LookChem

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206361-99-1

Articles about 206361-99-1Total 30 be found

More Articles about upstream products of 206361-99-1

Chemical Properties

Appearance/Colour :White amorphous solid

Melting Point: 74-76 °C

Density: 1.34 g/cm3

Solubility:Soluble in DMSO (>25 mg/ml)

Storage Temp.:-20°C Freezer

Refractive Index: 1.62

PKA: 11.43±0.46(Predicted)

PSA: 148.80000

LogP: 4.42820

Global suppliers and manufacturers of 206361-99-1total 158 suppliers on LookChem

Density: 1.34 g/cm³