example 11 [WO2014151871A9]   

GtoPdb Ligand ID: 10632

Synonyms: itacnosertib (proposed INN)
Compound class: Synthetic organic
Comment: The chemical structure that was submitted to the WHO for the INN itacnosertib is identical to the structure of example 11 that is claimed in Tolero Pharmaceuticals' patent WO2014151871A9 [1]. The INN submission declares itacnosertib as a 'serine/threonine kinase inhibitor'. Data presented in WO2014151871A9 provide evidence of example 11's activity as an inhibitor of the activin A receptor type 1 (ACVR1; a.k.a. ALK2) which is a Type I receptor serine/threonine kinase. Tolero have declared an ACVR1-targeting oncology programme on their pipeline webpage. The research code provided is TP-0184, but to date (Jan 2020) there has been no formal name>structure disclosure for this compound.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 91.33
Molecular weight 468.24
XLogP 3.11
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1cc(ccc1N1CCN(CC1)C)Nc1nccc(n1)Nc1cccnc1c1ccccn1
Isomeric SMILES COc1cc(ccc1N1CCN(CC1)C)Nc1nccc(n1)Nc1cccnc1c1ccccn1
InChI InChI=1S/C26H28N8O/c1-33-14-16-34(17-15-33)22-9-8-19(18-23(22)35-2)30-26-29-13-10-24(32-26)31-21-7-5-12-28-25(21)20-6-3-4-11-27-20/h3-13,18H,14-17H2,1-2H3,(H2,29,30,31,32)
InChI Key XSQKEVGTZSBVBR-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-N-[3-methoxy-4-(4-methylpiperazin-1-yl)phenyl]-4-N-(2-pyridin-2-ylpyridin-3-yl)pyrimidine-2,4-diamine
Synonyms
itacnosertib (proposed INN)
Database Links
CAS Registry No. 1628870-27-8 (source: WHO INN record)
GtoPdb PubChem SID 404859079
PubChem CID 86290265
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