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229975-97-7

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229975-97-7 Usage

Description

Atazanavir (BMS-232632, III), an azapeptide HIV protease inhibitor, has been developed and launched by Bristol-Myers Squibb (BMS), under worldwide license from Novartis, for the treatment of HIV infection. Atazanavir was launched in the US as Reyataz? in July 2003.

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 229975-97-7 differently. You can refer to the following data:
1. Atazanavir is a HIV protease inhibitor with Ki of 2.66 nM
2. Atazanavir Sulfate is an intermediate of Atazanavir(A790051) which is a novel azapeptide HIV protease Inhbitor. Antiviral.

Synthesis

The synthesis of atazanavir (III) appeared in several reports. The synthetic route depicted in the scheme was one of the best routes which was suitable for large scale production. The commercially available chiral diol 25 was converted to its silyl mesylate 26 in one pot via selective silylation and subsequent mesylation. This oily intermediate 26 was carried into the next step without further purification. The desilylation of 26 was achieved by using inexpensive ammonium fluoride. The resulting solid product 27 was readily isolated and further purified through recrystallization from IPA/H2O in 80% yield. The epoxide formation from 27 was affected by KOtBu in THF/IPA to provide enantiomerically pure epoxide 28 in 88% yield. Suzuki coupling of boronic acid 29 with bromopyridine (30) provided pyridyl benzaldehyde 31 in 80% yield after crystallization. The subsequent condensation of aldehyde 31 with t-butylcarbamate was carried out by refluxing in toluene/IPA and Shiff base 32 was collected by filtration upon cooling. Reduction of hydrazone 32 to hydrazine 33 was accomplished by employing a catalytic phase-transfer hydrogenation protocol (Pd/C, HCOONa) to furnish hydrazine 33 in 78% yield after crystallization. Coupling of the hydrazinocarbamate 33 with epoxide 28 was performed in refluxing IPA, followed by the addition of water to precipitate the crude product. Subsequent recrystallization from MeCN/H2O furnished 34 in 85% yield. Treatment of 34 with concentrated HCl in THF at 50oC removed the two Boc groups in 34 to give the product as an oil, which was then dissolved in a mixture of DCM/DIPEA and slowly transferred into a premixed solution of N-methoxycarbonyl- L-tert-leucine (35), HOBT, and WSC in DCM. After removal of the solvent the crude product was crystallized from IPA/EtOH to furnish the freebase 36 in 82% yield. The sulfate III was obtained by stirring the free base 36 with concentrated H2SO4 in EtOH at ambient temperature. Direct crystallization by addition of n-heptane provided the sulfate salt III as an easily filterable solid in 85% yield.

Check Digit Verification of cas no

The CAS Registry Mumber 229975-97-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,2,9,9,7 and 5 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 229975-97:
(8*2)+(7*2)+(6*9)+(5*9)+(4*7)+(3*5)+(2*9)+(1*7)=197
197 % 10 = 7
So 229975-97-7 is a valid CAS Registry Number.
InChI:InChI=1/C38H52N6O7.H2O4S/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28;1-5(2,3)4/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47);(H2,1,2,3,4)/t29-,30-,31+,32+;/m0./s1

229975-97-7 Well-known Company Product Price

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  • USP

  • (1044334)  Atazanavir sulfate  United States Pharmacopeia (USP) Reference Standard

  • 229975-97-7

  • 1044334-200MG

  • 4,647.24CNY

  • Detail

229975-97-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name atazanavir sulfate

1.2 Other means of identification

Product number -
Other names Atazanavir Bisulfate Salt

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:229975-97-7 SDS

229975-97-7Downstream Products

229975-97-7Relevant articles and documents

TABLETED COMPOSITIONS CONTAINING ATAZANAVIR

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, (2018/06/01)

Disclosed are compressed tablets containing atazanavir sulfate, optionally with another active agents, e.g., anti-HIV agents, granules that contain atazanavir sulfate and an intragranular lubricant that can be used to make the tablets, compositions comprising a plurality of the granules, processes for making the granules and tablets, and methods of treating HIV.

A process for preparing a sulfuric acid Atazanavir method (by machine translation)

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Paragraph 0018; 0019; 0020; 0021, (2017/08/29)

A is applied to the technical field of drug synthesis in the puma monomer as the raw material to prepare sulfuric acid Atazanavir method, the preparation method comprises the following steps: the puma monomer uses ethanol to dissolve after the dilution, t

PROCESS FOR THE PREPARATION OF ATAZANAVIR BISULFATE

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Paragraph 0086; 0087, (2015/07/15)

The present invention relates to an improved process for the preparation of Atazanavir bisulfate Form A. The present invention also relates to a pharmaceutical composition using the Atazanavir bisulfate Form A of the invention.

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