Lapaquistat acetate

Base Information

Chemical Name:Lapaquistat acetate
CAS No.:189060-13-7
Molecular Formula:C₃₃H₄₁ClN₂O₉
Molecular Weight:645.15
Hs Code.:
UNII:IUH3AY74O3
DSSTox Substance ID:DTXSID50432130
Nikkaji Number:J2.565.621K
Wikidata:Q27280898
NCI Thesaurus Code:C81535
Pharos Ligand ID:UBA3PCNLGZJX
ChEMBL ID:CHEMBL435224
Mol file:189060-13-7.mol

Synonyms:(1-(2-(1-(2-carboxyoxy-1,1-dimethylethyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydrobenzo(e)(1,4)oxazepin-3-yl)acetyl)piperidin-4-yl)acetic acid;1-((1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl)acetyl)piperidine-4-acetic acid;lapaquistat;TAK 475;TAK-475;TAK475

Suppliers and Price of Lapaquistat acetate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
LapaquistatAcetate
25mg
$ 10725.00

Sigma-Aldrich
TAK-475 ≥98% (HPLC)
5 mg
$ 129.00

Sigma-Aldrich
TAK-475 ≥98% (HPLC)
25 mg
$ 505.00

ChemScene
Lapaquistatacetate >99.0%
5mg
$ 480.00

ChemScene
Lapaquistatacetate >99.0%
1mg
$ 160.00

American Custom Chemicals Corporation
LAPAQUISTAT ACETATE 95.00%
25MG
$ 12370.05

American Custom Chemicals Corporation
LAPAQUISTAT ACETATE 95.00%
10MG
$ 7230.30

Total 13 raw suppliers

Chemical Property of Lapaquistat acetate

Chemical Property:

Melting Point:194-196℃
Boiling Point:826.4±65.0 °C(Predicted)
PKA:4.66±0.10(Predicted)
PSA：131.91000
Density:1.246±0.06 g/cm3(Predicted)
LogP:4.87400
Solubility.:Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:12
Exact Mass:644.2500586
Heavy Atom Count:45
Complexity:1050

Purity/Quality:

99%, ^*data from raw suppliers

LapaquistatAcetate ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(=O)OCC(C)(C)CN1C2=C(C=C(C=C2)Cl)C(OC(C1=O)CC(=O)N3CCC(CC3)CC(=O)O)C4=C(C(=CC=C4)OC)OC
Isomeric SMILES:CC(=O)OCC(C)(C)CN1C2=C(C=C(C=C2)Cl)[C@H](O[C@@H](C1=O)CC(=O)N3CCC(CC3)CC(=O)O)C4=C(C(=CC=C4)OC)OC
Recent ClinicalTrials:Effect of Lapaquistat Acetate on Blood Cholesterol Levels in Subjects With Elevated Cholesterol
Recent EU Clinical Trials:A Double-Blind, Randomized Study to Evaluate the Efficacy and Safety of Lapaquistat Acetate 50 mg versus Placebo in Subjects with Hypercholesterolemia, With an Optional Open-Label Extension
Uses A novel squalene synthase inhibitor A novel squalene synthase inhibitor. Lapaquistat acetate decreased plasma cholesterol and triglyceride levels, by lowering lipoproteins containing apoB100. Treatment with Lapaquistat acetate increased collagen concentration and transformed coronary plaques into fibromuscular plaques. Lapaquistat acetate also suppressed the expression of matrix metalloproteinase-1 and plasminogen activator inhibitor-1 in the plaque and increased peripheral coenzyme Q10 levels.Antiarteriosclerotics.

Technology Process of Lapaquistat acetate

There total 11 articles about Lapaquistat acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

: 383661-55-0
2-[(3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetic acid

: 73415-84-6
2-(piperidin-4-yl)acetic acid hydrochloride

: 189060-13-7
(1-{2-[(3R,5S)-1-(3-Acetoxy-2,2-dimethyl-propyl)-7-chloro-5-(2,3-dimethoxy-phenyl)-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]oxazepin-3-yl]-acetyl}-piperidin-4-yl)-acetic acid

Guidance literature:: 2-[(3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetic acid; With pivaloyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 2h;

2-(piperidin-4-yl)acetic acid hydrochloride; In acetonitrile; Product distribution / selectivity;

Reference yield: 77.0%

: 108-24-7
acetic anhydride

: 189059-71-0
N-[[(3R,5S)-1-(3-hydroxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetic acid

: 189060-13-7
(1-{2-[(3R,5S)-1-(3-Acetoxy-2,2-dimethyl-propyl)-7-chloro-5-(2,3-dimethoxy-phenyl)-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]oxazepin-3-yl]-acetyl}-piperidin-4-yl)-acetic acid

Guidance literature:: With pyridine; dmap; at 20 ℃; for 1h;
DOI:10.1021/jm020234o

Reference yield:

: 597-31-9
2,2-dimethyl-3-hydroxypropionaldehyde

: 189060-13-7
(1-{2-[(3R,5S)-1-(3-Acetoxy-2,2-dimethyl-propyl)-7-chloro-5-(2,3-dimethoxy-phenyl)-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]oxazepin-3-yl]-acetyl}-piperidin-4-yl)-acetic acid

Guidance literature:: Multi-step reaction with 8 steps

1: AcOH / methanol / 1 h / 60 °C

2: NaBH₃CN / methanol / 2 h / 60 °C

3: 100 percent / NaHCO₃ / ethyl acetate / 0.5 h / 20 °C

4: 79 percent / K₂CO₃ / ethanol / 20 °C

5: 94 percent / aq. NaOH / ethanol / 2 h / 60 °C

6: 57 percent / diethylphosphoryl cyanide; Et₃N / dimethylformamide / 0.5 h / 20 °C

7: 70 percent / 1N aq. NaOH / ethanol / 0.5 h / 60 °C

8: 77 percent / DMAP; pyridine / 1 h / 20 °C

With pyridine; dmap; sodium hydroxide; diethylphosphoryl cyanide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; In methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm020234o