API SYNTHESIS INTERNATIONAL: Asundexian

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Wednesday, 11 November 2026

Asundexian

Asundexian

CAS 2064121-65-7

MW 592.9 g/mol, C₂₆H₂₁ClF₄N₆O₄

4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxo-1-pyridinyl]butanoyl]amino]-2-fluorobenzamide

APPROVALS 2026, FDA 2026, Sunharbo, LA585UM8DE, BAY2433334, BAY 2433334

To reduce the risk of stroke in adults following a recent mild-to-moderate non-cardioembolic ischemic stroke or a high-risk transient ischemic attack

Asundexian, sold under the brand name Sunharbo, is a Factor XIa inhibitor developed by Bayer to prevent stroke.^[1]^[2]

Clinical trials

Asundexian efficacy and safety in patients have been evaluated in two clinical trial programs: phase IIb PACIFIC and phase III OCEANIC.^[3] In the phase IIb PACIFIC clinical trial programs, asundexian consistently showed no difference in bleeding rate compared with placebo^[4]^[5] and reduced the risk of bleeding compared with apixaban.^[6] All three trials in the programs were not powered to show efficacy of asundexian.^[3] However, a phase III trial, OCEANIC-AF, demonstrated a hazard ratio of 3.8 for stroke or systemic embolism with asundexian vs apixaban, so it was stopped due to a "lack of efficacy." The remaining active study OCEANIC-STROKE was recommended to continue as planned. Bayer is reevaluating the design of the OCEANIC-AFINA based on the findings of the OCEANIC trial.^[7]

In February 2026, the OCEANIC-STROKE trial was completed. This was a multicentre, randomised, double-blind, placebo-controlled study involving 12,000 people worldwide who had suffered a non-cardioembolic ischaemic stroke or a transient ischaemic attack. The trial revealed a 26% reduction in the rate of recurrence without major bleeding, a typical complication of antithrombotic drugs.^[8]^[9]^[10]

SYN

US10421742,

US20180194745 - Substituted oxopyridine derivatives

Example 235

4-({(2S)-2-[4-{5-Chloro-2-[4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenyl}-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)-2-fluorobenzamide (Enantiomer 2)

Enantiomer separation of 63 mg of 4-({2-[4-{5-chloro-2-[4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenyl}-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)-2-fluorobenzamide (racemate) gave 25 mg of enantiomer 1 (chiral HPLC: R _t=2.6 min) and 26 mg of the title compound (enantiomer 2): chiral HPLC: R _t=3.6 min; 100% ee.

Separating method: column: Chiralpak AD-H SFC, 5 μm 250 mm×20 mm; mobile phase: carbon dioxide 75%/ethanol 25%; temperature: 40° C.; flow rate: 80 ml/min; pressure: 100 bar; UV detection: 210 nm.

Analysis: column: Daicel AD SFC 3 μm, 100 mm×4.6 mm; mobile phase: 75% carbon dioxide, 25% ethanol; flow rate: 3 ml/min; UV detection: 210 nm.

LC-MS [Method 1]: R _t=0.92 min; MS (ESIpos): m/z=593 [M+H] ⁺

SYN1

MEDKOO

Synthetic Reference

Design and Preclinical Characterization Program toward Asundexian (BAY 2433334), an Oral Factor XIa Inhibitor for the Prevention and Treatment of Thromboembolic Disorders

By: Roehrig, Susanne; et al

Journal of Medicinal Chemistry (2023), 66(17), 12203-12224

SYN2

Synthetic Reference

Study on Preparation Process of Anticoagulant BAY2433334

By: Zeng, Yanqun; et al

Molecules (2024), 29(24), 6039

SYN3

Synthetic Reference

Preparation of triazole containing oxopyridine derivative and its application in medicine

Assignee: Tianjin Institute of Pharmaceutical Research Co., Ltd.

Inventors: Wei, Qunchao; et al

China

Patent#CN116903585 A

SYN REF

Discovery of potent, highly selective, and orally bioavailable factor XIa inhibitors for anticoagulant therapyPublication Name:European Journal of Medicinal ChemistryPublication Date:2025-05-05PMID:40010270DOI:10.1016/j.ejmech.2025.117436
Discovery of potent and selective factor XIa inhibitors incorporating triazole-based benzoic acid as novel P2’ fragments: Molecular dynamics simulations and anticoagulant activityPublication Name:European Journal of Medicinal ChemistryPublication Date:2025-01-15PMID:39580913DOI:10.1016/j.ejmech.2024.117067
Design, synthesis and biological evaluation of 6-chloro-quinolin-2-one derivatives as novel FXIa inhibitorsPublication Name:Bioorganic & Medicinal Chemistry LettersPublication Date:2024-02-01PMID:38211702DOI:10.1016/j.bmcl.2024.129610
Design and Preclinical Characterization Program toward Asundexian (BAY 2433334), an Oral Factor XIa Inhibitor for the Prevention and Treatment of Thromboembolic DisordersPublication Name:Journal of Medicinal ChemistryPublication Date:2023-09-05PMCID:PMC10510402PMID:37669040DOI:10.1021/acs.jmedchem.3c00795
Factor XIa Inhibitors in Anticoagulation Therapy: Recent Advances and PerspectivesPublication Name:Journal of Medicinal ChemistryPublication Date:2023-04-10PMID:37037122DOI:10.1021/acs.jmedchem.2c02130

Pat

Process for the preparation of monoazo dyesPublication Number:DE-522201-CPriority Date:1928-05-15Grant Date:1931-04-01, Publication Number:BE-638782-A, Publication Number:BE-625897-A, Publication Number:BE-499305-A

Synthesis of 13-alkyl-gon-4-onesPublication Number:US-3959322-APriority Date:1960-09-22Grant Date:1976-05-25
Self-supporting explosives mixture that can be deformed into foils and other structuresPublication Number:DE-1124412-BPriority Date:1960-08-17
Process for the production of chemical compoundsPublication Number:DE-1445151-A1Priority Date:1959-09-25
Polyepoxide diphenolic acid amide compositions and said compositions modified with aldehyde condensatesPublication Number:US-2907740-APriority Date:1958-10-14Grant Date:1959-10-06
Process for the production of alcoholsPublication Number:DE-933864-C

References

Heitmeier, Stefan; Visser, Mayken; Tersteegen, Adrian; Dietze-Torres, Julia; Glunz, Julia; Gerdes, Christoph; Laux, Volker; Stampfuss, Jan; Roehrig, Susanne (June 2022). "Pharmacological profile of asundexian, a novel, orally bioavailable inhibitor of factor XIa". Journal of Thrombosis and Haemostasis. 20 (6): 1400–1411. doi:10.1111/jth.15700. PMC 9313898. PMID 35289054.
Roehrig, Susanne; Ackerstaff, Jens; Jiménez Núñez, Eloísa; Teller, Henrik; Ellerbrock, Pascal; Meier, Katharina; Heitmeier, Stefan; Tersteegen, Adrian; Stampfuss, Jan; Lang, Dieter; Schlemmer, Karl-Heinz; Schaefer, Martina; Gericke, Kersten M.; Kinzel, Tom; Meibom, Daniel (2023-09-05). "Design and Preclinical Characterization Program toward Asundexian (BAY 2433334), an Oral Factor XIa Inhibitor for the Prevention and Treatment of Thromboembolic Disorders". Journal of Medicinal Chemistry. 66 (17): 12203–12224. doi:10.1021/acs.jmedchem.3c00795. ISSN 0022-2623. PMC 10510402. PMID 37669040.
"Bayer initiates landmark Phase III study program to investigate oral FXIa inhibitor asundexian". Bayer (Press release). 2022-08-28. Retrieved 2023-12-27.
"AntiCoagulation via Inhibition of FXIa by the Oral Compound BAY 2433334 – Non-cardioembolic Stroke". American College of Cardiology. Retrieved 2023-12-26.
Rao, Sunil V.; Kirsch, Bodo; Bhatt, Deepak L.; Budaj, Andrzej; Coppolecchia, Rosa; Eikelboom, John; James, Stefan K.; Jones, W. Schuyler; Merkely, Bela; Keller, Lars; Hermanides, Renicus S.; Campo, Gianluca; Ferreiro, José Luis; Shibasaki, Taro; Mundl, Hardi (2022-10-18). "A Multicenter, Phase 2, Randomized, Placebo-Controlled, Double-Blind, Parallel-Group, Dose-Finding Trial of the Oral Factor XIa Inhibitor Asundexian to Prevent Adverse Cardiovascular Outcomes After Acute Myocardial Infarction". Circulation. 146 (16): 1196–1206. doi:10.1161/CIRCULATIONAHA.122.061612. hdl:11392/2520330. ISSN 0009-7322. PMID 36030390.
"The Next Wave of Anticoagulation: Results of PACIFIC-AF and the Future Role of Factor XIa Inhibition in Atrial Fibrillation". American College of Cardiology. Retrieved 2023-12-26.
"OCEANIC-AF study stopped early due to lack of efficacy". Bayer (Press release). 2023-11-19. Retrieved 2023-12-27.
Piccini, Jonathan P.; Patel, Manesh R.; Steffel, Jan; Ferdinand, Keith; Van Gelder, Isabelle C.; Russo, Andrea M.; Ma, Chang-Sheng; Goodman, Shaun G.; Oldgren, Jonas; Hammett, Christopher; Lopes, Renato D.; Akao, Masaharu; De Caterina, Raffaele; Kirchhof, Paulus; Gorog, Diana A.; Hemels, Martin; Rienstra, Michiel; Jones, W. Schuyler; Harrington, Josephine; Lip, Gregory Y.H.; Ellis, Stephen J.; Rockhold, Frank W.; Neumann, Christoph; Alexander, John H.; Viethen, Thomas; Hung, James; Coppolecchia, Rosa; Mundl, Hardi; Caso, Valeria (2025). "Asundexian versus Apixaban in Patients with Atrial Fibrillation". New England Journal of Medicine. 392 (1): 23–32. doi:10.1056/NEJMoa2407105. hdl:2066/315752. PMID 39225267.
"Ictus ischemico, i risultati della ricerca su un nuovo farmaco sperimentale: recidive ridotte del 26%". Ospedale Maggiore di Bologna (in Italian).
"Bayer's asundexian demonstrated a substantial 26% reduction in stroke after a non-cardioembolic ischemic stroke or high-risk transient ischemic attack, with no increase in ISTH major bleeding versus placebo". Bayer.

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Clinical data
Trade names	Sunharbo
Other names	BAY-2433334; BAY2433334
Legal status
Legal status	US: ℞-only
Identifiers
IUPAC name
CAS Number	2064121-65-7
PubChem CID	135206011
ChemSpider	115009501
UNII	LA585UM8DE
KEGG	D12838
Chemical and physical data
Formula	C₂₆H₂₁ClF₄N₆O₄
Molar mass	592.94 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI