Plodicitinib

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Plodicitinib

CAS 2360992-48-7

MF C19H22FN7O2 MW399.42

1-[(3S,4R)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one

1-[(3S,4R)-3-({2-[(1-ethyl-1H-pyrazol-4-yl)amino]-7Hpyrrolo[2,3-d]pyrimidin-4-yl}oxy)-4-fluoropiperidin-1-yl]prop2-en-1-one
Janus tyrosine kinase 3/TEC family kinase inhibitor, antiinflammatory, veterinary, SX5UEP3JXA

Plodicitinib is a Janus tyrosine kinase 3/TEC family kinase inhibitor with anti-inflammatory activity.

Plodicitinib is a small-molecule, dual Janus tyrosine kinase 3 (JAK3) and TEC family kinase (specifically BTK) inhibitor that exhibits strong anti-inflammatory properties.

Mechanism of Action

The compound blocks specific enzymatic pathways involved in cellular signaling:

JAK3 Inhibition: It targets Janus kinase 3, which plays an essential role in transmitting signals for cytokines that regulate immune cell development and activation.
TEC/BTK Inhibition: It blocks Bruton’s tyrosine kinase (BTK), a component vital for B-cell development and activation. [1, 2]
Combined Effect: By blocking these pathways, it suppresses the overactive immune and inflammatory responses that drive autoimmune and allergic conditions.

Applications and Development Status

Veterinary Medicine: In early 2026, Daewoong Pharmaceutical submitted an application to the Animal and Plant Quarantine Agency in South Korea for commercial approval of plodicitinib. It is being positioned as a specialized, companion animal-only treatment to manage atopic dermatitis in dogs.
Research Use: In the scientific community, it is actively utilized as a laboratory tool compound to study kinase signaling pathways and inflammatory disease models.

US11339167,

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=US306969271&_cid=P22-MSL6QJ-67927-1

Example 4: Preparation of 1-(cis-3-((2-((1-ethyl-1H-pyrazol-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one

19.3 mg (yield: 27.8%) of the title compound was obtained in the same manner as in Example 1, except that cis-tert-butyl-4-fluoro-3-hydroxypiperidine-1-carboxylate was used instead of trans-tert-butyl-4-fluoro-3-hydroxypiperidine-1-carboxylate in Example 1.

Example 5: Preparation of 1-((3S,4R)-3-((2-((1-ethyl-1H-pyrazol-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one

16.2 mg (yield: 57.4%) of the title compound was obtained in the same manner as in Example 1, except that tert-butyl(3S,4R)-4-fluoro-3-hydroxypiperidine-1-carboxylate was used instead of trans-tert-butyl-4-fluoro-3-hydroxypiperidine-1-carboxylate in Example 1.

1H NMR (500 MHz, CD ₃OD) δ 7.98 (s, 1H), 7.57-7.55 (m, 1H), 6.88-6.45 (m, 2H), 6.30-5.98 (m, 2H), 5.80-5.44 (m, 2H), 5.20-5.05 (m, 1H), 4.40-4.12 (m, 3H), 4.05-3.52 (m, 3H), 2.24-2.21 (m, 1H), 2.01-1.94 (m, 1H), 1.47-1.43 (m, 3H)

Example 25: Preparation of 1-((3S,4S)-3-((2-((1-ethyl-1H-pyrazol-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one

The compound of Example 1 was separated by CHIRALCEL OZ-H column to obtain the title compound with an analysis time of 10.1 minutes.
1H NMR (500 MHz, CD 3OD) δ 7.98-7.95 (m, 1H), 7.57-7.55 (m, 1H), 6.84-6.53 (m, 2H), 6.26-6.08 (m, 2H), 5.78-5.52 (m, 1H), 5.41-5.40 (m, 1H), 5.10-5.04 (m, 1H), 4.50-4.06 (m, 4H), 3.89-3.86 (m, 1H), 3.55-3.50 (m, 1H), 2.19-2.16 (m, 1H), 1.95-1.94 (m, 1H), 1.45-1.41 (m, 3H)

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2025121903&_cid=P22-MSL6W2-73218-1

1-((3S,4R)-3-((2-((1-ethyl-1H-pyrazole-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidine-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one is represented by the following chemical formula 1: