Zasocitinib

TAK-279
Identifiers
	IUPAC name N-[(1R,2R)-2-methoxycyclobutyl]-7-(methylamino)-5-[(2-oxo-1-pyridin-2-ylpyridin-3-yl)amino]pyrazolo[1,5-a]pyrimidine-3-carboxamide;
CAS Number	2272904-53-5;
PubChem CID	137441492;
ChemSpider	115277123;
UNII	C293MNS6TQ;
ChEMBL	ChEMBL5314423;
Chemical and physical data
Formula	C23H24N8O3
Molar mass	460.498 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNC1=CC(=NC2=C(C=NN12)C(=O)N[C@@H]3CC[C@H]3OC)NC4=CC=CN(C4=O)C5=CC=CC=N5;
	InChI InChI=1S/C23H24N8O3/c1-24-20-12-18(27-16-6-5-11-30(23(16)33)19-7-3-4-10-25-19)29-21-14(13-26-31(20)21)22(32)28-15-8-9-17(15)34-2/h3-7,10-13,15,17,24H,8-9H2,1-2H3,(H,27,29)(H,28,32)/t15-,17-/m1/s1; Key:BWINBHTTZLVXGT-NVXWUHKLSA-N;

Zasocitinib (TAK-279, NDI-034858) is a drug which is an orally active, highly selective tyrosine kinase 2 (TYK2) inhibitor. It has been researched for various inflammatory conditions including psoriatic arthritis and Crohn's disease.^[1]^[2]^[3] It is significantly more selective than earlier compounds over side targets such as JAK1, which is hoped to give it an improved side effect profile.^[4]

References

^ Leit S, Greenwood J, Carriero S, Mondal S, Abel R, Ashwell M, Blanchette H, Boyles NA, Cartwright M, Collis A, Feng S, Ghanakota P, Harriman GC, Hosagrahara V, Kaila N, Kapeller R, Rafi SB, Romero DL, Tarantino PM, Timaniya J, Toms AV, Wester RT, Westlin W, Srivastava B, Miao W, Tummino P, McElwee JJ, Edmondson SD, Masse CE. Discovery of a Potent and Selective Tyrosine Kinase 2 Inhibitor: TAK-279. J Med Chem. 2023 Aug 10;66(15):10473-10496. doi:10.1021/acs.jmedchem.3c00600 PMID 37427891
^ Kivitz AJ. The investigational tyrosine kinase inhibitor TAK-279 is effective and well tolerated in patients with active psoriatic arthritis in phase 2b study. Cleveland Clinic Journal of Medicine. 14 Nov 2023
^ Kivitz A, et al. Efficacy and Safety Outcomes of TAK-279, a Selective Oral Tyrosine Kinase 2 (TYK2) Inhibitor, from a Randomized, Double-blind, Placebo-controlled Phase 2b Trial in Patients with Active Psoriatic Arthritis. American College of Rheumatology October 24, 2023
^ The Discovery Process of TAK-279 and the Deep Logic Behind its Acquisition by Takeda. synapse.patsnap.com, 10 August 2023

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[1] Leit S, Greenwood J, Carriero S, Mondal S, Abel R, Ashwell M, Blanchette H, Boyles NA, Cartwright M, Collis A, Feng S, Ghanakota P, Harriman GC, Hosagrahara V, Kaila N, Kapeller R, Rafi SB, Romero DL, Tarantino PM, Timaniya J, Toms AV, Wester RT, Westlin W, Srivastava B, Miao W, Tummino P, McElwee JJ, Edmondson SD, Masse CE. Discovery of a Potent and Selective Tyrosine Kinase 2 Inhibitor: TAK-279. J Med Chem. 2023 Aug 10;66(15):10473-10496. doi:10.1021/acs.jmedchem.3c00600 PMID 37427891

[2] Kivitz AJ. The investigational tyrosine kinase inhibitor TAK-279 is effective and well tolerated in patients with active psoriatic arthritis in phase 2b study. Cleveland Clinic Journal of Medicine. 14 Nov 2023

[3] Kivitz A, et al. Efficacy and Safety Outcomes of TAK-279, a Selective Oral Tyrosine Kinase 2 (TYK2) Inhibitor, from a Randomized, Double-blind, Placebo-controlled Phase 2b Trial in Patients with Active Psoriatic Arthritis. American College of Rheumatology October 24, 2023

[4] The Discovery Process of TAK-279 and the Deep Logic Behind its Acquisition by Takeda. synapse.patsnap.com, 10 August 2023

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[2]

[3]

[4]

Identifiers

IUPAC name N-[(1R,2R)-2-methoxycyclobutyl]-7-(methylamino)-5-[(2-oxo-1-pyridin-2-ylpyridin-3-yl)amino]pyrazolo[1,5-a]pyrimidine-3-carboxamide
CAS Number	2272904-53-5
PubChem CID	137441492
ChemSpider	115277123
UNII	C293MNS6TQ
ChEMBL	ChEMBL5314423
Chemical and physical data
Formula	C₂₃H₂₄N₈O₃
Molar mass	460.498 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CNC1=CC(=NC2=C(C=NN12)C(=O)N[C@@H]3CC[C@H]3OC)NC4=CC=CN(C4=O)C5=CC=CC=N5
InChI InChI=1S/C23H24N8O3/c1-24-20-12-18(27-16-6-5-11-30(23(16)33)19-7-3-4-10-25-19)29-21-14(13-26-31(20)21)22(32)28-15-8-9-17(15)34-2/h3-7,10-13,15,17,24H,8-9H2,1-2H3,(H,27,29)(H,28,32)/t15-,17-/m1/s1 Key:BWINBHTTZLVXGT-NVXWUHKLSA-N

Zasocitinib

See also

References