ChemicalBook > CAS DataBase List > Vorapaxar Sulfate

Vorapaxar Sulfate

Product Name
Vorapaxar Sulfate
CAS No.
705260-08-8
Chemical Name
Vorapaxar Sulfate
Synonyms
Zontivity;Sch 530348;Vorapaxar-d5;Vorapaxar Sulfate;SCH 530348 sulfate;SCH-530348;SCH530348;vorapaxar impurity A;vorapaxar monosulfate;Vorapaxar Sulfate API;SCH 530348 (H2SO4 Salt)
CBNumber
CB92545858
Molecular Formula
C29H35FN2O8S
Formula Weight
590.66
MOL File
705260-08-8.mol
More
Less

Vorapaxar Sulfate Property

storage temp. 
4°C, away from moisture
solubility 
DMSO : 125 mg/mL (211.63 mM; Need ultrasonic)| (insoluble)
form 
Solid
color 
White to off-white
Water Solubility 
Water : < 0.1 mg/mL (ultrasonic;warming;heat to 60°C)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H320Causes eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

TRC
Product number
V758200
Product name
VorapaxarSulfate
Packaging
100mg
Price
$580
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0014130
Product name
SCH-530348 SULPHATE
Purity
95.00%
Packaging
5MG
Price
$500.42
Updated
2021/12/16
DC Chemicals
Product number
DC8229
Product name
VorapaxarSulfate(SCH530348)
Purity
>98%
Packaging
100mg
Price
$550
Updated
2021/12/16
Crysdot
Product number
CD11069485
Product name
VorapaxarSulfate
Purity
97%
Packaging
250mg
Price
$456
Updated
2021/12/16
DC Chemicals
Product number
DC8229
Product name
VorapaxarSulfate(SCH530348)
Purity
>98%
Packaging
250mg
Price
$950
Updated
2021/12/16
More
Less

Vorapaxar Sulfate Chemical Properties,Usage,Production

Description

Merck Sharp & Dohme successfully obtained approval in the EU in 2014 for vorapaxar sulfate, marketed as Zontivity®. The drug is a first-in-class thrombin receptor (also referred to as a protease-activated or PAR-1) antagonist which, when used in conjunction with antiplatelet therapy, has been shown to reduce the chance of myocardial infarction and stroke, particularly in patients with a history of cardiac events. Antagonism of PAR-1 allows for thrombin-mediated fibrin deposition while blocking thrombinmediated platelet activation.

Uses

SCH-530348 is a novel antiplatelet agent undergoing development by Schering-Plough Corp for the treatment and prevention of atherothrombosis. acute coronary syndrome (unstable angina/non-ST segment elevation myocardial infarction) and secondary prevention of cardiovascular events in high-risk patients.

Definition

ChEBI: An organic sulfate salt obtained by combining vorapaxar with one molar equivalent of sulfuric acid. A protease-activated receptor-1 antagonist used for the reduction of thrombotic cardiovascular events in patients with a history of myocardial infarction (M ) or with peripheral arterial disease. It has been shown to reduce the rate of a combined endpoint of cardiovascular death, MI, stroke and urgent coronary revascularisation.

Synthesis

Although a variety of papers and patents describe the synthesis of vorapaxar sulfate (XXXVII), a combination of two patents describe the largest-scale synthesis reported in the literature. Retrosynthetically, the drug can be divided into olefination partners 306 and 305. Lactone 305 is further derived from synthons 300 and 299, which are readily prepared from commercially available starting materials. Dienyl acid 300 was constructed in two steps starting from commercial vinyl bromide 307, which first undergoes a Heck reaction with methacrylate (308) followed by saponification of the ester to afford the desired acid 300 in 71% over two steps.
The synthesis of alcohol 299 begins with tetrahydropyranyl (THP) protection of enantioenriched alcohol 295 to afford butyne 297 . Lithiation of this system followed by trapping with (benzyloxy)chloroformate and Dowex work-up to remove the protective functionality provided acetyl ester 298. Hydrogenation of the alkyne with Lindlar?ˉs catalyst delivered cis-allylic alcohol 299 in 93% yield. Acid 300 was then esterified with alcohol 299 by way of a 1,3-dicyclohexylcarbodiimide (DCC) coupling and, upon heating in refluxing xylenes, an intramolecular Diels¨C Alder reaction occurred. Subsequent subjection to DBU secured the tricyclic system 301 in 38% over three steps as a single enantiomer. Diastereoselective hydrogenation reduced the olefin with concomitant benzyl removal to give key fragment 302. Next, acidic revelation of the ketone followed by reductive amination with ammonium formate delivered primary amines 303a/303b as a mixture of diastereomers. These amines were then converted to the corresponding carbamates, and resolution by means of recrystallization yielded 50% of 304 as the desired diastereomer. Acid 304 was treated with oxalyl chloride and the resulting acid chloride was reduced to aldehyde 305 in 66% overall yield. Finally, deprotonation of phosphonate ester 306 followed by careful addition of 305 and acidic quench delivered vorapaxar sulfate (XXXVII) in excellent yield over the two-step protocol.
The preparation of vorapaxar phosponate ester 306 commenced from commercial sources of 5-(3-fluorophenyl)-2- methylpyridine (310). Removal of the methyl proton with LDA followed by quench with diethyl chlorophosphonate resulted in phosponate ester 306.

Vorapaxar Sulfate Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Vorapaxar Sulfate Suppliers

Toronto Research Chemicals
Tel
--
Fax
--
Email
info@trc-canada.com
Country
Canada
ProdList
6038
Advantage
71
More
Less

View Lastest Price from Vorapaxar Sulfate manufacturers

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Vorapaxar Sulfate 705260-08-8
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-10-09
Hebei Best Biological Technology Co., Ltd
Product
Vorapaxar sulfate 705260-08-8
Price
US $200.00/g
Min. Order
10g
Purity
99%
Supply Ability
1000t/month
Release date
2022-11-30
Hebei Mingeng Biotechnology Co., Ltd
Product
Vorapaxar Sulfate 705260-08-8
Price
US $200.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg/Month
Release date
2022-11-23

705260-08-8, Vorapaxar SulfateRelated Search:


  • Vorapaxar Sulfate
  • N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(1E)-2-[5-(3-Fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1-Methyl-3-oxonaphtho[2,3-c]furan-6-yl]carbaMic Acid Ethyl Ester Sulfate
  • Sch 530348
  • SCH 530348 (H2SO4 Salt)
  • vorapaxar impurity A
  • Carbamic acid, N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(1E)-2-[5-(3-fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1-methyl-3-oxonaphtho[2,3-c]furan-6-yl]-, ethyl ester, sulfate (1:1)
  • SCH-530348;SCH530348
  • Vorapaxar Sulfate (SCH 530348)
  • Vorapaxar-d5
  • SCH 530348 sulfate
  • vorapaxar monosulfate
  • Zontivity
  • Vorapaxar sulfateQ: What is Vorapaxar sulfate Q: What is the CAS Number of Vorapaxar sulfate Q: What is the storage condition of Vorapaxar sulfate Q: What are the applications of Vorapaxar sulfate
  • Vorapaxar Sulfate API
  • Ethyl ((1R,3aR,4aR,6R,8aR,9S,9aS)-9-((E)-2-(5-(3-fluorophenyl)pyridin-2-yl)vinyl)-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl)carbamate sulfate
  • 705260-08-8
  • C29H33FN2O4H2SO4
  • C29H35FN2O8S
  • Aromatics
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals