Brepocitinib

 

Brepocitinib

CAS 1883299-62-4

MF C₁₈H₂₁F₂N₇O MW389.4 g/mol

8/27/2026, APPROVALS 2026, FDA 2026, Lisraya, PF 06700841, 3X8387Q25N, PF-06700841

[(1S)-2,2-difluorocyclopropyl]-[(1R,5S)-3-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone

• [(1S)-2,2-difluorocyclopropyl]-[(1S,5R)-3-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone
• Methanone, ((1S)-2,2-difluorocyclopropyl)(3-(2-((1-methyl-1H-pyrazol-4-yl)amino)-4-pyrimidinyl)-3,8-diazabicyclo(3.2.1)oct-8-yl)-
• ((1S)-2,2-difluorocyclopropyl)-((1S,5R)-3-(2-((1-methylpyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo(3.2.1)octan-8-yl)methanone

To treat dermatomyositis in adults

Brepocitinib (brand name Lisraya) is an oral, once-daily dual TYK2/JAK1 inhibitor approved by the FDA for treating dermatomyositis in adults.

Developed by Roivant (via its subsidiary Priovant), it is the first oral targeted therapy indicated to manage this rare, debilitating autoimmune condition. Brepocitinib, sold under the brand name Lisraya, is a drug which acts as a dual inhibitor of JAK1 and TYK2, and was developed for the treatment of plaque psoriasis.^[1][2][3][4] It is used for the treatment of dermatomyositis.

Brepocitinib is an orally available, selective inhibitor of non-receptor tyrosine-protein kinase TYK2 (tyrosine kinase 2) and tyrosine-protein kinase JAK1 (Janus kinase 1; JAK1) with potential immunomodulatory and anti-inflammatory activities. Upon oral administration, brepocitinib selectively binds to and inhibits the activation of TYK2 and JAK1, thereby disrupting TYK2 and JAK-1-dependent cytokine signaling. This may reduce inflammatory responses and prevent inflammation-induced damage caused by certain immunological diseases. TYK2 and JAK-1 are members of the Janus kinase family of non-receptor tyrosine kinases and are involved in signaling pathways affecting hematopoiesis, immunity and inflammation.

SYN

Dual Inhibition of TYK2 and JAK1 for the Treatment of Autoimmune Diseases: Discovery of ((S)-2,2-Difluorocyclopropyl)((1R,5S)-3-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone (PF-06700841)

By: Fensome, Andrew ; et al

Journal of Medicinal Chemistry (2018), 61(19), 8597-8612

SYN

Preparation of aminopyrimidinyl derivatives as inhibitors of JAK kinases useful in therapy of diseases

Assignee: Pfizer Inc.

Inventors: Fensome, Andrew; et al

World Intellectual Property Organization

Patent#WO2016027195 A1

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2016027195&_cid=P11-MTCC5U-40903-1

SYN

https://www.sciencedirect.com/science/article/abs/pii/S0223523423008152

SYN

compound 23 [PMID: 30113844]

PAT

US9663526,

https://patentscope.wipo.int/search/en/detail.jsf?docId=US159751917&_cid=P11-MTCCDC-53135-1

Examples 7 and 8

[(1S)-2,2-difluorocyclopropyl][(1R,5S)-3-{2-[(1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}-3,8-diazabicyclo[3.2.1]oct-8-yl]methanone and [(1R)-2,2-difluorocyclopropyl][(1R,5S)-3-{2-[(1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}-3,8-diazabicyclo[3.2.1]oct-8-yl]methanone

To a solution of (S)-2,2-difluorocyclopropane-1-carboxylic acid (Preparation 68, 318 mg, 2.61 mmol) in DCM (20 mL) was added 4-((1R,5S)-3,8-diazabicyclo[3.2.1]octan-3-yl)-N-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine hydrochloride (Preparation 19, 700 mg, 2.17 mmol), HATU (1.02 g, 2.61 mmol and DIPEA (0.76 mL, 4.34 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction was diluted with DCM and saturated aqueous ammonium chloride solution. The organic layer was separated, washed with further ammonium chloride solution and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-12% MeOH and 1% NH 4OH in DCM. The residue was dissolved in DCM and further washed with saturated aqueous ammonium chloride solution three times. The organic layer was collected, concentrated in vacuo and dried to afford the title compound (500 mg, 60%).

The title compound and its enantiomer may also be prepared according to the same method using racemic 2,2-difluorocyclopropane-1-carboxylic acid with additional chiral separation of the enantiomers after purification using the method below to afford:

Peak 1: Example 7

[(1S)-2,2-difluorocyclopropyl][(1R,5S)-3-{2-[(1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}-3,8-diazabicyclo[3.2.1]oct-8-yl]methanone

1H NMR (400 MHz, DMSO-d 6): δ ppm 1.58-2.06 (m, 6H), 2.82-3.27 (m, 3H), 3.80 (s, 3H), 4.14 (br s, 2H), 4.55-4.74 (m, 2H), 6.07-6.19 (m, 1H), 7.44 (s, 1H), 7.74 (brs, 1H), 7.93 (d, 1H), 8.90 (brs, 1H). MS m/z 390 [M+H]; [α] D 2050.1 (c 1.27, EtOH)

PAT

• New compounds for the inhibition of angiogenesis and use of thereofPublication Number:AU-2005223356-A1Priority Date:2004-03-24
• Compositions and methods of use for modified release minoxidilPublication Number:US-2025325546-A1
• Aminopyrimidinyl compoundsPublication Number:US-10980815-B2Priority Date:2014-08-21Grant Date:2021-04-20
• Aminopyrimidinyl compounds as JAK inhibitorsPublication Number:MD-4800-C1Priority Date:2014-08-21
• Aminopyrimidinyl compoundsPublication Number:US-2020330477-A1Priority Date:2014-08-21
• Aminopyrimidinyl compoundsPublication Number:US-11197867-B2Priority Date:2014-08-21Grant Date:2021-12-14
• Aminopyrimidinyl compoundsPublication Number:TW-201609706-APriority Date:2014-08-21

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References

References

1.  Fensome A, Ambler CM, Arnold E, Banker ME, Brown MF, Chrencik J, et al. (October 2018). "Dual Inhibition of TYK2 and JAK1 for the Treatment of Autoimmune Diseases: Discovery of (( S)-2,2-Difluorocyclopropyl)((1 R,5 S)-3-(2-((1-methyl-1 H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone (PF-06700841)". Journal of Medicinal Chemistry. 61 (19): 8597–8612. doi:10.1021/acs.jmedchem.8b00917. PMID 30113844.
2.  Forman SB, Pariser DM, Poulin Y, Vincent MS, Gilbert SA, Kieras EM, et al. (December 2020). "TYK2/JAK1 Inhibitor PF-06700841 in Patients with Plaque Psoriasis: Phase IIa, Randomized, Double-Blind, Placebo-Controlled Trial". The Journal of Investigative Dermatology. 140 (12): 2359–2370.e5. doi:10.1016/j.jid.2020.03.962. PMID 32311398.
3.  Martin G (February 2023). "Novel Therapies in Plaque Psoriasis: A Review of Tyrosine Kinase 2 Inhibitors". Dermatology and Therapy. 13 (2): 417–435. doi:10.1007/s13555-022-00878-9. PMC 9884727. PMID 36592300.
4.  Caso F, Costa L, Triggianese P, Maione F, Bertolini N, Vastarella M, et al. (May 2023). "Recent developments for new investigational JAK inhibitors in psoriatic arthritis". Expert Opinion on Investigational Drugs. 32 (5): 361–371. doi:10.1080/13543784.2023.2207737. PMID 37096862.

Clinical data
Trade names	Lisraya
Other names	PF-06700841
Identifiers
IUPAC name
CAS Number	1883299-62-4
PubChem CID	118878093
DrugBank	DB15003
ChemSpider	72380129
UNII	3X8387Q25N
ChEMBL	ChEMBL4297477
Chemical and physical data
Formula	C18H21F2N7O
Molar mass	389.411 g·mol−1
3D model (JSmol)	Interactive image
SMILES
InChI

///////////brepocitinib, anax labs, APPROVALS 2026, FDA 2026, Lisraya, PF 06700841, 3X8387Q25N, PF-06700841, dermatomyositis

#brepocitinib, #anax labs, #APPROVALS 2026, #FDA 2026, #Lisraya, #PF 06700841, #3X8387Q25N, #PF-06700841, #dermatomyositis

Rezuforimod

 

Rezuforimod

CAS 1431754-15-2

MF C15H20BrN3O4, MW386.24 g/mol

((4-Bromophenyl)carbamoyl)-L-leucylglycine

2-[[(2S)-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanoyl]amino]acetic acid

N-[(4-bromophenyl)carbamoyl]-L-leucylglycine
N-formyl peptide receptor 1 and 2 agonist, antiinflammatory, AGN-232411, AG-80308, AGN 232411, AG 80308, 54P16AUY6D

Rezuforimod is an experimental drug that acts as a potent and selective agonist of formyl peptide receptor 2 with an EC₅₀ of 0.88 nM, which inhibits neutrophil adhesion and has antiinflammatory effects.^[1][2]

Rezuforimod (also known by development codes AGN-232411 and AG-80308) is an experimental, first-in-class small molecule drug primarily being developed as a topical ophthalmic solution to treat dry eye disease (DED). It targets inflammation, which is a major underlying driver of dry eye symptoms and ocular surface damage.

---

👁️ Mechanism of Action

Rezuforimod operates through a targeted anti-inflammatory pathway:

• FPR2 Agonism: It acts as a highly potent and selective agonist of Formyl Peptide Receptor 2 (FPR2/ALX), binding with an EC₅₀ of 0.88 nM.
• Neutrophil Inhibition: Activating this receptor successfully inhibits neutrophil adhesion and migration to the ocular surface.
• Inflammation Resolution: By mimicking natural pro-resolving leagues, it shuts down chronic inflammatory cascades on the corneal surface rather than just suppressing the immune system globally.

🔬 Clinical Trial Findings & Efficacy

In clinical assessments, Rezuforimod has shown excellent potential as a localized therapy:

• Dosing: It is formulated as an eye drop administered twice daily (BID).
• Objective Improvement: Over a 3-month trial period, it significantly reduced corneal and conjunctival staining scores (an objective measure of tissue damage on the surface of the eye). The most pronounced improvements were recorded at Day 43 and Day 84.
• Subjective Relief: Patients reported a notable reduction in daily ocular discomfort and an improved Ocular Surface Disease Index (OSDI) score.
• Safety Profile: The drug has demonstrated a favorable safety profile with no serious drug-related adverse events, and no abnormal shifts in vital signs or systemic blood chemistry.

A Study of AG-80308 in Dry Eye PatientsCTID:NCT05372107, Phase: Phase 1

Status:Completed, Date:2022-11-29

SYN

• The formyl peptide receptors FPR1 and FPR2 as targets for inflammatory disorders: recent advances in the development of small-molecule agonistsPublication Name:European Journal of Medicinal ChemistryPublication Date:2024-02-05PMID:38199163DOI:10.1016/j.ejmech.2023.115989
• Synthesis and evaluation of novel cyclopentane urea FPR2 agonists and their potential application in the treatment of cardiovascular inflammationPublication Name:European Journal of Medicinal ChemistryPublication Date:2021-03-15PMID:33548634DOI:10.1016/j.ejmech.2021.113194
• Recent advances in the design and development of formyl peptide receptor 2 (FPR2/ALX) agonists as pro-resolving agents with diverse therapeutic potentialPublication Name:European Journal of Medicinal ChemistryPublication Date:2021-03-05PMID:33486199DOI:10.1016/j.ejmech.2021.113167

PAT

US10208071, Compound 8

https://patentscope.wipo.int/search/en/detail.jsf?docId=US205825234&_cid=P10-MT81MF-62360-1

PAT

WO2013062947 

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2013062947&_cid=P10-MT81PJ-63770-1

PAT

• Amide derivatives of N-urea substituted amino acids as formyl peptide receptor like-1 (FPRL-1) receptor modulatorsPublication Number:US-10993931-B2Priority Date:2011-10-26Grant Date:2021-05-04
• Amide derivatives of n-urea substituted amino acids as formyl peptide receptor like-1 (fprl-1) receptor modulatorsPublication Number:WO-2013062947-A1Priority Date:2011-10-26
• Substituted N-urea amino acid amide derivatives as modulators of formylated peptide receptor 1 (FPRL-1) receptorPublication Number:ES-2820714-T3Priority Date:2011-10-26Grant Date:2021-04-22
• Amide derivatives of N-urea-substituted amino acids as formyl peptide receptor-like-1 (FPRL-1) receptor modulatorsPublication Number:CN-106518742-APriority Date:2011-10-26

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References

References

1.  Maciuszek M, Cacace A, Brennan E, Godson C, Chapman TM (March 2021). "Recent advances in the design and development of formyl peptide receptor 2 (FPR2/ALX) agonists as pro-resolving agents with diverse therapeutic potential". European Journal of Medicinal Chemistry. 213 113167. doi:10.1016/j.ejmech.2021.113167. PMID 33486199.
2.  Maciuszek M, Ortega-Gomez A, Maas SL, Perretti M, Merritt A, Soehnlein O, et al. (March 2021). "Synthesis and evaluation of novel cyclopentane urea FPR2 agonists and their potential application in the treatment of cardiovascular inflammation". European Journal of Medicinal Chemistry. 214 113194. doi:10.1016/j.ejmech.2021.113194. PMID 33548634.

Identifiers
IUPAC name
CAS Number	1431754-15-2
PubChem CID	71526099
UNII	54P16AUY6D
ChEMBL	ChEMBL4785302
Chemical and physical data
Formula	C15H20BrN3O4
Molar mass	386.246 g·mol−1
3D model (JSmol)	Interactive image
SMILES
InChI

////////rezuforimod, anax labs, N-formyl peptide receptor 1 and 2 agonist, antiinflammatory, AGN-232411, AG-80308, AGN 232411, AG 80308, 54P16AUY6D

#rezuforimod, #anax labs, #N-formyl peptide receptor 1 and 2 agonist, #antiinflammatory, #AGN-232411, #AG-80308, #AGN 232411, #AG 80308, #54P16AUY6D

Rezosicone

 

Rezosicone

CAS 1414777-24-4

MF C29H40O2 MW420.63

3β-(benzyloxy)-17-methylpregn-5-en-20-one
cannabinoid CB1 receptor signalling inhibitor, S79V5L677D

1-[(3S,8R,9S,10R,13S,14S,17S)-10,13,17-trimethyl-3-phenylmethoxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]ethanone

1-((3S,8R,9S,10R,13S,14S,17S)-3-(benzyloxy)-10,13,17-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one

Pregn-5-en-20-one, 17-methyl-3-(phenylmethoxy)-, (3β)-

3β-(benzyloxy)-17-methylpregn-5-en-20-one

Rezosicone is a potent and selective cannabinoid CB1 receptor signaling inhibitor (or antagonist) primarily used in biochemical and pharmacology research

Biological Mechanism

Rezosicone selectively binds to and inhibits the CB1 receptor. CB1 receptors are heavily concentrated in the central nervous system and play a key role in regulating appetite, pain sensation, mood, and memory. Compounds in this class are frequently studied in research related to metabolic disorders, obesity, and addiction

Pat

https://patentscope.wipo.int/search/en/detail.jsf?docId=EP339768848&_cid=P12-MT571S-81533-1

Synthesis of the 3β-(benzyloxy)-17α-methyl-pregn-5-en-20-one

[0104]  MgO (100 mg; 2.42 mmol; 2 eq.) and 2-benzyloxy-1-methylpyridinium Inflate (850 mg; 2.42 mmol; 2.0 eq.) were added to a solution of 17a-methyl-pregnenolone (400 mg; 1.21 mmol; 1 eq.) in trifluorotoluene (10 ml). The reaction medium was stirred for one night at 85°C, then filtered on celite and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (eluent: cyclohexane/AcOEt 95/5) then by crystallisation in acetone to give the 3β-(benzyloxy)-17α-methyl-pregn-5-en-20-one (0.28 g; 36%) as a white solid.

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References

• 3beta-(benzyloxy)-17alpha-methyl-pregn-5-en-20-one for use in the treatment of cognitive disordersPublication Number:US-2022017562-A1Priority Date:2018-12-18
• 3beta-(BENZYLOXY)-17alpha-METHYL-PREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERSPublication Number:HR-P20241376-T1Priority Date:2018-12-18
• 3-beta-(benzyloxy)-17-alpha-methyl-pregn-5-en-20-one for use in the treatment of cognitive disordersPublication Number:HU-E068626-T2Priority Date:2018-12-18
• 3-(BENZYLIOX)-17-METHYLPREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERSPublication Number:FI-3897655-T3Priority Date:2018-12-18Grant Date:2024-09-17
• 3BETA-(BENZYLOXY)-17ALPHA-METHYL-PREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERSPublication Number:MA-54518-B1Priority Date:2018-12-18
• 3BETA-(BENZYLOXY)-17ALPHA-METHYLPREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERSPublication Number:SM-T202400425-T1Priority Date:2018-12-18
• 3beta-(benzyloxy)-17alpha-methyl-pregn-5-en-20-one for use in the treatment of cognitive disordersPublication Number:ZA-202103284-BPriority Date:2018-12-18
• 3Beta-(benzyloxy)-17alpha-methyl-pregn-5-en-20-one for use in the treatment of cognitive disordersPublication Number:ES-2987823-T3Priority Date:2018-12-18Grant Date:2024-11-18
• 3beta-(benzyloxy)-17alpha-methyl-pregn-5-en-20-one for use in the treatment of cognitive disordersPublication Number:DK-3897655-T3Priority Date:2018-12-18Grant Date:2024-09-23
• 3beta-(BENZYLOXY)-17alpha-METHYL-PREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERSPublication Number:EP-3897655-A1Priority Date:2018-12-18
• 3BETA-(BENZYLOXY)-17ALFA-METHYL-PREGN-5-EN-20-ONE FOR USE IN TREATMENT OF COGNITIVE DISORDERSPublication Number:PL-3897655-T3Priority Date:2018-12-18
• 3beta-(Benzyloxy)-17α-methyl-pregn-5-en-20-one for use in the treatment of cognitive disordersPublication Number:MD-3897655-T2Priority Date:2018-12-18
• 3BETA-(BENZYLOXY)-17ALPHA-METHYL-PREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERSPublication Number:PT-3897655-TPriority Date:2018-12-18
• 3BETA-(BENZYLOXY)-17ALPHA-METHYL-PREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERSPublication Number:RS-66013-B1Priority Date:2018-12-18
• 3beta-(benzyloxy)-17alpha-methyl-pregn-5-en-20-one for use in the treatment of cognitive disordersPublication Number:EP-3897655-B1Priority Date:2018-12-18Grant Date:2024-07-17
• 3β-(BENZYLOXY)-17α-METHYL-PREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERSPublication Number:WO-2020127468-A1Priority Date:2018-12-18
• 3β-(Benzyloxy)-17α-methyl-pregnant-5-en-20-one for the treatment of cognitive impairmentPublication Number:CN-113260366-BPriority Date:2018-12-18Grant Date:2024-03-08
• 3BETA-(BENZYLOXY)-17ALPHA-METHYL-PREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERSPublication Number:LT-3897655-TPriority Date:2018-12-18
• 3béta-(benzyloxy)-17alpha-methyl-pregn-5-en-20-one for use in the treatment of cognitive disordersPublication Number:EP-3669876-A1Priority Date:2018-12-18

///////rezosicone, anax labs, cannabinoid CB1 receptor signalling inhibitor, S79V5L677D

#rezosicone, #anax labs, #cannabinoid CB1 receptor signalling inhibitor, #S79V5L677D

Napazimone

 

Napazimone

https://newdrugapprovals.org/2026/02/17/napazimone/

Anthony Melvin Crasto AfricurePharma Row2Tech Anax AdvectProc Niper-G

Mevrometostat

 

Mevrometostat

https://newdrugapprovals.org/2026/02/10/mevrometostat/

Anthony Melvin Crasto AfricurePharma Row2Tech Anax AdvectProc Niper-G

Fanregratinib

Fanregratinib

https://newdrugapprovals.org/2026/01/23/fanregratinib/

Anthony Melvin Crasto AfricurePharma Row2Tech Anax AdvectProc Niper-G

 

Enrupatinib

 Enrupatinib

https://newdrugapprovals.org/2026/01/20/enrupatinib/

Anthony Melvin Crasto AfricurePharma Row2Tech Anax AdvectProc Niper-G