Home Fluorides 875446-37-0
875446-37-0,MFCD16294903
Catalog No.:AA00394L

875446-37-0 | (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-({2-[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]-5-(trifluoromethyl)phenyl}methyl)-4-methyl-1,3-oxazolidin-2-one

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1mg
98+%
in stock  
$6.00   $4.00
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2mg
98+%
in stock  
$7.00   $5.00
- +
5mg
98+%
in stock  
$9.00   $7.00
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10mg
98+%
in stock  
$12.00   $8.00
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25mg
98+%
in stock  
$15.00   $11.00
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50mg
98+%
in stock  
$23.00   $16.00
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1g
98%
in stock  
$328.00   $230.00
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5g
98%
in stock  
$976.00   $683.00
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10g
98%
in stock  
$1,692.00   $1,184.00
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25g
98%
in stock  
$3,070.00   $2,149.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00394L
Chemical Name:
(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-({2-[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]-5-(trifluoromethyl)phenyl}methyl)-4-methyl-1,3-oxazolidin-2-one
CAS Number:
875446-37-0
Molecular Formula:
C30H25F10NO3
Molecular Weight:
637.5084
MDL Number:
MFCD16294903
SMILES:
COc1cc(F)c(cc1c1ccc(cc1CN1C(=O)O[C@@H]([C@@H]1C)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C(F)(F)F)C(C)C
Properties
Computed Properties
 
Complexity:
964  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
44  
Hydrogen Bond Acceptor Count:
13  
Rotatable Bond Count:
6  
XLogP3:
8.8  

Downstream Synthesis Route

[1]Patent:WO2006/14357,2006,A1.Locationinpatent:Page/Pagecolumn80

[2]Patent:WO2006/14357,2006,A1.Locationinpatent:Page/Pagecolumn80-81

[1]CurrentPatentAssignee:CONCERTPHARMACEUTICALSINC-US2008/242711,2008,A1Locationinpatent:Page/Pagecolumn15-16

[1]CurrentPatentAssignee:MERCK&COINC-WO2010/39474,2010,A1Locationinpatent:Page/Pagecolumn11

C34H29F10NO8(2-)*2Na(1+) 
  875446-37-0 

[1]CurrentPatentAssignee:MERCK&COINC-WO2010/39474,2010,A1Locationinpatent:Page/Pagecolumn43

(4S,5R)-5-3,5-bis(trifluoromethyl)phenyl-4-methyl-1,3-oxazolidin-2-one 
 
2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl 
  875446-37-0 

[1]CurrentPatentAssignee:MERCK&COINC-WO2007/5572,2007,A1Locationinpatent:Page/Pagecolumn11-12

Literature

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Title: Anacetrapib as lipid-modifying therapy in patients with heterozygous familial hypercholesterolaemia (REALIZE): a randomised, double-blind, placebo-controlled, phase 3 study.

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Title: Cholesteryl ester transfer protein inhibition as a strategy to reduce cardiovascular risk.

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Title: Rationale for cholesteryl ester transfer protein inhibition.

Journal: Current opinion in lipidology 20120801

Title: HDL and CETP Inhibition: Will This DEFINE the Future?

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Title: Safety of inhibition of cholesteryl ester transfer protein with anacetrapib: the DEFINE study.

Journal: Expert review of cardiovascular therapy 20120801

Title: Lack of a meaningful effect of anacetrapib on the pharmacokinetics and pharmacodynamics of warfarin in healthy subjects.

Journal: British journal of clinical pharmacology 20120701

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Journal: European heart journal 20120701

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Title: On- and off-target pharmacology of torcetrapib: current understanding and implications for the structure activity relationships (SAR), discovery and development of cholesteryl ester-transfer protein (CETP) inhibitors.

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Journal: Expert opinion on investigational drugs 20120101

Title: Lipid exchange mechanism of the cholesteryl ester transfer protein clarified by atomistic and coarse-grained simulations.

Journal: PLoS computational biology 20120101

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Journal: Vascular health and risk management 20120101

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Journal: Core evidence 20120101

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Journal: Vascular health and risk management 20120101

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Journal: MMW Fortschritte der Medizin 20111208

Title: Cholesteryl ester transfer protein inhibition in cardiovascular risk management: ongoing trials will end the confusion.

Journal: Cardiovascular therapeutics 20111201

Title: Familial hypercholesterolemia: present and future management.

Journal: Current cardiology reports 20111201

Title: Multidimensional profiling of plasma lipoproteins by size exclusion chromatography followed by reverse-phase protein arrays.

Journal: Journal of lipid research 20111201

Title: Lack of an effect of anacetrapib on the pharmacokinetics of digoxin in healthy subjects.

Journal: Biopharmaceutics & drug disposition 20111201

Title: Cholesteryl ester transfer protein inhibition to reduce cardiovascular risk: Where are we now?

Journal: Trends in pharmacological sciences 20111201

Title: Update on therapies targeting HDL: the mystery continues.

Journal: Current opinion in lipidology 20111201

Title: Leoligin, the major lignan from Edelweiss, activates cholesteryl ester transfer protein.

Journal: Atherosclerosis 20111101

Title: Anacetrapib promotes reverse cholesterol transport and bulk cholesterol excretion in Syrian golden hamsters.

Journal: Journal of lipid research 20111101

Title: Investigational CETP antagonists for hyperlipidemia and atherosclerosis prevention.

Journal: Expert opinion on investigational drugs 20111101

Title: Anacetrapib: a new weapon against dyslipidemia.

Journal: Current clinical pharmacology 20111101

Title: Anacetrapib: hope for CETP inhibitors?

Journal: Cardiovascular therapeutics 20111001

Title: Efficacy and safety after cessation of treatment with the cholesteryl ester transfer protein inhibitor anacetrapib (MK-0859) in patients with primary hypercholesterolemia or mixed hyperlipidemia.

Journal: American heart journal 20111001

Title: Different effects of compounds decreasing cholesteryl ester transfer protein activity on lipoprotein metabolism.

Journal: Current opinion in lipidology 20110801

Title: Biphenyl-substituted oxazolidinones as cholesteryl ester transfer protein inhibitors: modifications of the oxazolidinone ring leading to the discovery of anacetrapib.

Journal: Journal of medicinal chemistry 20110714

Title: Model-based development of anacetrapib, a novel cholesteryl ester transfer protein inhibitor.

Journal: The AAPS journal 20110601

Title: Triglyceride-rich lipoproteins and high-density lipoprotein cholesterol in patients at high risk of cardiovascular disease: evidence and guidance for management.

Journal: European heart journal 20110601

Title: The cholesterol ester transfer protein inhibitor, anacetrapib.

Journal: Current opinion in lipidology 20110601

Title: [Cholesteryl ester transfer protein inhibition in the management of atherosclerotic cardiovascular disease: second act 'A rebirth of hope'].

Journal: Revista medica de Chile 20110601

Title: A bivariate genome-wide approach to metabolic syndrome: STAMPEED consortium.

Journal: Diabetes 20110401

Title: Preparative scale synthesis of the biaryl core of anacetrapib via a ruthenium-catalyzed direct arylation reaction: unexpected effect of solvent impurity on the arylation reaction.

Journal: The Journal of organic chemistry 20110304

Title: Effect of diltiazem, a moderate CYP3A inhibitor, on the pharmacokinetics of anacetrapib, a potent cholesteryl ester transfer protein inhibitor, in healthy subjects.

Journal: Journal of clinical pharmacology 20110301

Title: The DEFINE study: a bright future for CETP inhibitors?

Journal: Expert opinion on investigational drugs 20110301

Title: Clinical Trials Update AHA Congress 2010.

Journal: Cardiovascular drugs and therapy 20110201

Title: CETP inhibition shows promise as way to reduce cardiovascular disease risk.

Journal: JAMA 20110112

Title: Trial watch: hope renewed for strategy to raise HDL cholesterol.

Journal: Nature reviews. Drug discovery 20110101

Title: Anacetrapib and dalcetrapib: two novel cholesteryl ester transfer protein inhibitors.

Journal: The Annals of pharmacotherapy 20110101

Title: [Novel therapy for atherosclerosis and inflammatory vascular disease].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20110101

Title: Cardiovascular disease and dyslipidemia: beyond LDL.

Journal: Current pharmaceutical design 20110101

Title: Analysis of in vitro bioactivity data extracted from drug discovery literature and patents: Ranking 1654 human protein targets by assayed compounds and molecular scaffolds.

Journal: Journal of cheminformatics 20110101

Title: Dyslipidaemia of obesity, metabolic syndrome and type 2 diabetes mellitus: the case for residual risk reduction after statin treatment.

Journal: The open cardiovascular medicine journal 20110101

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Title: New insights into the mechanism of low high-density lipoprotein cholesterol in obesity.

Journal: Lipids in health and disease 20110101

Title: Medical angioplasty - hope and expectations: an optimistic overview.

Journal: Journal of family & community medicine 20110101

Title: Safety of anacetrapib in patients with or at high risk for coronary heart disease.

Journal: The New England journal of medicine 20101216

Title: Modulating cholesteryl ester transfer protein activity maintains efficient pre-β-HDL formation and increases reverse cholesterol transport.

Journal: Journal of lipid research 20101201

Title: Good news for 'good' cholesterol.

Journal: Nature 20101118

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Journal: Expert opinion on emerging drugs 20100901

Title: Biochemical characterization of cholesteryl ester transfer protein inhibitors.

Journal: Journal of lipid research 20100901

Title: Drug off-target effects predicted using structural analysis in the context of a metabolic network model.

Journal: PLoS computational biology 20100901

Title: Dissociating HDL cholesterol from cardiovascular risk.

Journal: Lancet (London, England) 20100731

Title: Cholesterol efflux potential and antiinflammatory properties of high-density lipoprotein after treatment with niacin or anacetrapib.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20100701

Title: Dalcetrapib: a review of Phase II data.

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Title: [Recent advances in the research on HDL subfraction].

Journal: Rinsho byori. The Japanese journal of clinical pathology 20100601

Title: High-density lipoprotein-mediated anti-atherosclerotic and endothelial-protective effects: a potential novel therapeutic target in cardiovascular disease.

Journal: Current pharmaceutical design 20100501

Title: Pharmacokinetics, metabolism, and excretion of anacetrapib, a novel inhibitor of the cholesteryl ester transfer protein, in rats and rhesus monkeys.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100301

Title: Metabolism and excretion of anacetrapib, a novel inhibitor of the cholesteryl ester transfer protein, in humans.

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Title: Effects of fenofibrate on lipid profiles, cholesterol ester transfer activity, and in-stent intimal hyperplasia in patients after elective coronary stenting.

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Title: Update on CETP inhibition.

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Title: Triglycerides and HDL cholesterol: stars or second leads in diabetes?

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Title: Design of the DEFINE trial: determining the EFficacy and tolerability of CETP INhibition with AnacEtrapib.

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Title: Single-dose pharmacokinetics and pharmacodynamics of anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy subjects.

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Title: The end of the road for CETP inhibitors after torcetrapib?

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Title: Effect of cholesteryl ester transfer protein inhibitor on vitamin E transport should be studied.

Journal: American heart journal 20090701

Title: Drug discovery using chemical systems biology: identification of the protein-ligand binding network to explain the side effects of CETP inhibitors.

Journal: PLoS computational biology 20090501

Title: Assessment of a pharmacokinetic and pharmacodynamic interaction between simvastatin and anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy subjects.

Journal: British journal of clinical pharmacology 20090501

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20090401

Title: Efficacy and safety of the cholesteryl ester transfer protein inhibitor anacetrapib as monotherapy and coadministered with atorvastatin in dyslipidemic patients.

Journal: American heart journal 20090201

Title: Assessment of the CYP3A-mediated drug interaction potential of anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy volunteers.

Journal: Journal of clinical pharmacology 20090101

Title: High-density lipoprotein cholesterol: current perspective for clinicians.

Journal: Angiology 20090101

Title: Raising HDL cholesterol in women.

Journal: International journal of women's health 20090101

Title: Multiple-dose pharmacodynamics and pharmacokinetics of anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy subjects.

Journal: Clinical pharmacology and therapeutics 20081201

Title: JTT-705: is there still future for a CETP inhibitor after torcetrapib?

Journal: Expert opinion on investigational drugs 20081001

Title: The failure of torcetrapib: what have we learned?

Journal: British journal of pharmacology 20080801

Title: Torcetrapib-induced blood pressure elevation is independent of CETP inhibition and is accompanied by increased circulating levels of aldosterone.

Journal: British journal of pharmacology 20080801

Title: Anacetrapib: new hope for cholesteryl ester transfer protein inhibitors in the treatment of dyslipidemia.

Journal: Nature clinical practice. Cardiovascular medicine 20080601

Title: Treating high-density lipoprotein cholesterol: a return to inhibition of cholesteryl ester transfer protein?

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Title: Cholesteryl ester transfer protein inhibition and HDL increase: has the dream ended?

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Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20080301

Title: HDL metabolism and CETP inhibition.

Journal: Cardiology in review 20080101

Title: Effect of the cholesteryl ester transfer protein inhibitor, anacetrapib, on lipoproteins in patients with dyslipidaemia and on 24-h ambulatory blood pressure in healthy individuals: two double-blind, randomised placebo-controlled phase I studies.

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Title: Dong B, et al. CETP inhibitors downregulate hepatic LDL receptor and PCSK9 expression in vitro and in vivo through a SREBP2 dependent mechanism. Atherosclerosis. 2014 Aug;235(2):449-62.

Title: Tan EY, et al. Pharmacokinetics, metabolism, and excretion of anacetrapib, a novel inhibitor of the cholesteryl ester transfer protein, in rats and rhesus monkeys. Drug Metab Dispos. 2010, 38(3), 459-473.

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Tags:875446-37-0 Molecular Formula|875446-37-0 MDL|875446-37-0 SMILES|875446-37-0 (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-({2-[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]-5-(trifluoromethyl)phenyl}methyl)-4-methyl-1,3-oxazolidin-2-one