Relacatib

Base Information

• Chemical Name: Relacatib
• CAS No.: 362505-84-8
• Molecular Formula: C27H32N4O6S
• Molecular Weight: 540.6312
• European Community (EC) Number: 838-013-6
• UNII: BL51M8CB8R
• DSSTox Substance ID: DTXSID30957639
• Nikkaji Number: J2.749.993G
• Wikidata: Q27088529
• NCI Thesaurus Code: C66512
• Pharos Ligand ID: 2XKVA83UNJQR
• Metabolomics Workbench ID: 149753
• ChEMBL ID: CHEMBL203665
• Mol file: 362505-84-8.mol

Synonyms:N-((1S)-3-methyl-1-((((4S,7R)-7-methyl-3-oxo-1-(2-pyridinylsulfonyl)hexahydro-1H-azepin-4-yl)amino)carbonyl)-butyl)-1-benzofuran-2-carboxamide;relacatib;SB 462795;SB-462795;SB462795

Chemical Property of Relacatib

Chemical Property:

• PSA: 147.06000
• Density: 1.34 g/cm³
• LogP: 4.69990
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 540.20425593
• Heavy Atom Count: 38
• Complexity: 967

Purity/Quality:

99% ^*data from raw suppliers

RELACATIB 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(=O)CN1S(=O)(=O)C2=CC=CC=N2)NC(=O)C(CC(C)C)NC(=O)C3=CC4=CC=CC=C4O3
• Isomeric SMILES: C[C@@H]1CC[C@@H](C(=O)CN1S(=O)(=O)C2=CC=CC=N2)NC(=O)[C@H](CC(C)C)NC(=O)C3=CC4=CC=CC=C4O3
• Recent ClinicalTrials: Study To Determine The Effects Of Doses Of Relacatib On The Metabolism Of Acetaminophen, Ibuprofen And Atorvastatin
• Recent EU Clinical Trials: A Phase II, randomized, double-blind, parallel group study to examine bone quality and bone mineral density changes following treatment with SB-462795 (40mg, 80mg, 120mg or 160mg), alendronate or placebo in postmenopausal women with osteoporosis.
• Uses: Treatment of osteoporosis.

Technology Process of Relacatib

There total 22 articles about Relacatib 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: 97.0%

benzofuran-2-carboxylic acid{(S)-1-[(3S,4S,7R)-3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide + Dess-Martin periodane (87413-09-0) → benzofuran-2-carboxylic acid{(S)-3-methyl-1-[(4S,7R)-7-methyl-3-oxo-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide (362505-84-8,362507-64-0)

Guidance literature:

In dichloromethane;

Reference yield: 85.0%

N-[(1S)-1-({[(3S,4S,7R)-3-hydroxy-7-methyl-1-(2-pyridinylsulfonyl)hexahydro-1H-azepin-4-yl]-amino}carbonyl)-3-methylbutyl]-1-benzofuran-2-carboxamide (362507-77-5) → Relacatib (362505-84-8,362507-64-0)

Guidance literature:

With acetic anhydride; In dimethyl sulfoxide; at 50 - 55 ℃; for 3h; Inert atmosphere; Large scale reaction;

DOI:10.1016/j.tet.2009.06.022

Reference yield: 32.0%

benzofuran-2-carboxylic acid {(S)-1-[3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)azepan-4-ylcarbamoyl]-3-methylbutyl}amide (403700-48-1) → Relacatib (362505-84-8,362507-64-0) + Benzofuran-2-carboxylic acid {(S)-3-methyl-1-[(4R,7S)-7-methyl-3-oxo-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide (362507-64-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1021/jm050915u

upstream raw materials:

benzofuran-2-carboxylic acid {(S)-1-[3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)azepan-4-ylcarbamoyl]-3-methylbutyl}amide

2-methyl-2,3,4,7-tetrahydro-azepine-1-carboxylic acid benzyl ester

allyl(1-methylpent-4-enyl)carbamic acid benzyl ester

[(S)-1-(3-hydroxy-7-methylazepan-4-ylcarbamoyl)-3-methylbutyl]carbamic acid tert-butyl ester

Refernces

• 1、 Wang, Huan,Matsuhashi, Hayao,Doan, Brian D.,Goodman, Steven N.,Ouyang, Xi,Clark Jr., William M.. "Large-scale synthesis of SB-462795, a cathepsin K inhibitor: the RCM-based approaches". experimental part. p. 6291 - 6303. Retrieved 2009/12/04.
• 2、 Yamashita, Dennis S.,Marquis, Robert W.,Xie, Ren,Nidamarthy, Sirishkumar D.,Oh, Hye-Ja,Jeong, Jae U.,Erhard, Karl F.,Ward, Keith W.,Roethke, Theresa J.,Smith, Brian R.,Cheng,Geng, Xiaoliu,Lin, Fan,Offen, Priscilla H.,Wang, Bing,Nevins, Neysa,Head, Martha S.,Haltiwanger, R. Curtis,Sarjeant, Amy A. Narducci,Liable-Sands, Louise M.,Zhao, Baoguang,Smith, Ward W.,Janson, Cheryl A.,Gao, Enoch,Tomaszek, Thaddeus,McQueney, Michael,James, Ian E.,Gress, Catherine J.,Zembryki, Denise L.,Lark, Michael W.,Veber, Daniel F.. "Structure activity relationships of 5-, 6-, and 7-methyl-substituted azepan-3-one cathepsin K inhibitors". . p. 1597 - 1612. Retrieved 2007/10/03.