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

• (S)-4-(2-(4-(5-Chloro-2-(4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl)phenyl)-5-methoxy-2-oxopyridin-1(2H)-yl)butanamido)-2-fluorobenzamide
• 4-[[(2~{S})-2-[4-[5-chloranyl-2-[4-(trifluoromethyl)-1,2,3-triazol-1-yl]phenyl]-5-methoxy-2-oxidanylidene-pyridin-1-yl]butanoyl]amino]-2-fluoranyl-benzamide
• (S)-4-[2-[4-[5-Chloro-2-[4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1(2H)-yl]butanamido]-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

1. 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.
2. 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.
3. "Bayer initiates landmark Phase III study program to investigate oral FXIa inhibitor asundexian". Bayer (Press release). 2022-08-28. Retrieved 2023-12-27.
4. "AntiCoagulation via Inhibition of FXIa by the Oral Compound BAY 2433334 – Non-cardioembolic Stroke". American College of Cardiology. Retrieved 2023-12-26.
5. 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.
6. "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.
7. "OCEANIC-AF study stopped early due to lack of efficacy". Bayer (Press release). 2023-11-19. Retrieved 2023-12-27.
8. 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.
9. "Ictus ischemico, i risultati della ricerca su un nuovo farmaco sperimentale: recidive ridotte del 26%". Ospedale Maggiore di Bologna (in Italian).
10. "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

//////////Asundexian, anax labs,, APPROVALS 2026, FDA 2026, Sunharbo, LA585UM8DE, BAY2433334, BAY 2433334

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Bepirovirsen

 

Bepirovirsen

CAS 1403787-62-1

NA SALT 1403787-62-1

Formula	C230H309N88O115P19S19
Molar mass	7344.14 g·mol−1

FDA 2026, APPROVALS 2026, Hibsago, hepatitis B

To treat chronic hepatitis B virus infection in certain adults without cirrhosis, in combination with existing antiviral therapy

Bepirovirsen (sold as Hibsago) is a first-in-class antisense oligonucleotide injection developed by GSK and Ionis Pharmaceuticals to treat chronic hepatitis B (CHB). It acts as a potential functional cure by targeting viral RNA, reducing surface antigen levels, and stimulating the immune system.

What It Does & How It Works

• Mechanism of Action: A non-GalNAc-conjugated antisense oligonucleotide that recognizes and destroys hepatitis B virus RNA, lowers viral protein production, and activates immune responses.
• Functional Cure Definition: Achieves sustained HBV DNA suppression and undetectable hepatitis B surface antigen (HBsAg) for at least 24 weeks after stopping all treatments.
• Clinical Trial Results: In the Phase 3 B-Well 1 and B-Well 2 trials, 19% to 24% of eligible patients achieved a functional cure and safely discontinued existing antiviral medications.

Regulatory Status & Approvals

• United States: Approved by the FDA in October 2026 for use in certain adults without cirrhosis who have been on antiviral therapy for at least six months and have HBsAg levels of 3,000 IU/mL or less. It features a boxed warning for potential serious liver reactions and low platelet counts.
• Japan: Approved as the first functional cure option for chronic hepatitis B under the brand name Hibsago.
• Other Designations: Granted Breakthrough Therapy and Priority Review designations in China and SENKU designation in Japan.

Bepirovirsen, sold under the brand name Hibsago, is an antisense oligonucleotide gapmer developed to treat hepatitis B infection.^[1]

PAT

WO2012145697

PAT

WO2024214041A1

https://patents.google.com/patent/WO2024214041A1/en

Bepirovirsen is an ASO currently in clinical evaluation for treating Chronic HBV infections. It is compound ISIS No. 505358 as disclosed in WO2012/145697. Bepirovirsen has 20 linked nucleosides and has a nucleobase sequence of 5'-GCAGAGGTGAAGCGAAGTGC- 3' (SEQ ID NO: 1), and it includes: a gap segment consisting of ten linked deoxynucleosides, a 5' wing segment consisting of 5 linked nucleosides, and a 3' wing segment consisting of 5 linked nucleosides, wherein the gap segment is positioned between the 5' wing segment and the 3' wing segment, wherein each nucleoside of each wing segment includes a 2'-O-methoxyethyl sugar, wherein each intemucleoside linkage is a phosphorothioate linkage, and wherein each cytosine is a 5 -methylcytosine. The CAS Registry Number of bepirovirsen is 1403787-62-1.

AHB-137 is an unconjugated ASO that is believed to have the same nucleobase sequence as bepirovirsen. AHB-137 is developed by Ausper Biopharma Co., Ltd. and is currently investigated in clinical studies for treating HBV infections. See WO2023/131098; Qiu, X. et al., “AHB-137, a novel and potent hepatitis B virus antisense oligonucleotide with a favorable preclinical pharmacokinetics and safety profile,” EASL 2023, Abstract No. SAT-178 (concluding that “the novel HBV ASO AHB-137 has demonstrated a favorable preclinical pharmacokinetics and safety profile”); Wu, X. et al., “AHB-137, a novel hepatitis B virus antisense oligonucleotide with substantially enhanced in vitro and in vivo antiviral activity,” EASL 2023, Abstract No. SAT-173 (concluding that “AHB-137 has more potent activity in reducing serum HBsAg than BPV [bepirovirsen] across multiple in vitro and in vivo HBV models, by reducing intrahepatic HBV RNA and HBsAg”).

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References

Mak, Lung-Yi; Hui, Rex Wan-Hin; Fung, James; Seto, Wai-Kay; Yuen, Man-Fung (2 November 2023). "Bepirovirsen (GSK3228836) in chronic hepatitis B infection: an evaluation of phase II progress". Expert Opinion on Investigational Drugs. 32 (11): 971–983. doi:10.1080/13543784.2023.2277389. PMID 37902953. S2CID 264672407.

Clinical data
Trade names	Hibsago
Other names	GSK3228836
Identifiers
IUPAC name
CAS Number	1403787-62-1
UNII	Z87O6SM01N
ChEMBL	ChEMBL4650468
Chemical and physical data
Formula	C230H309N88O115P19S19
Molar mass	7344.14 g·mol−1
SMILES
InChI

///////////////bepirovirsen, anax labs, FDA 2026, APPROVALS 2026, Hibsago, hepatitis B

#bepirovirsen, #anax labs, #FDA 2026, #APPROVALS 2026, #Hibsago, #hepatitis B

Tarvicopan

 

Tarvicopan

CAS2378381-06-5

MW C24H22N2O4 MW 402.4 g/mol

2-[2-[[7-[2-(aminomethyl)-4-pyridinyl]-2-methyl-1-benzofuran-5-yl]methoxy]phenyl]acetic acid

• 2-[[7-[2-(Aminomethyl)-4-pyridinyl]-2-methyl-5-benzofuranyl]methoxy]benzeneacetic acid
• Benzeneacetic acid, 2-[[7-[2-(aminomethyl)-4-pyridinyl]-2-methyl-5-benzofuranyl]methoxy]-
• [2-({7-[2-(aminomethyl)pyridin-4-yl]-2-methyl-1-benzofuran-5-yl}methoxy)phenyl]acetic acid
• 2-[2-[[7-[2-(aminomethyl)-4-pyridinyl]-2-methyl-1-benzofuran-5-yl]methoxy]phenyl]acetic acid

[2-({7-[2-(aminomethyl)pyridin-4-yl]-2-methyl-1-benzofuran-5-yl}methoxy)phenyl]acetic acid
complement factor D inhibitor, MWL2DF9UJJ

Tarvicopan is an investigational small-molecule compound that acts as an inhibitor of complement factor D.

Mechanism and Clinical Context

• Complement Factor D Inhibitor: It specifically targets factor D, a rate-limiting enzyme in the alternative pathway of the complement system. The complement system is a crucial part of the innate immune response, but its overactivation is linked to several autoimmune and inflammatory diseases.

PAT

US11370774,

Compound 112c

PAT

WO2019195720

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2019195720&_cid=P11-MV8WTL-54517-1

Scheme-112

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References

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Suraxavir marboxil

 

Suraxavir marboxil

CAS 2364589-86-4

MFC29H25F2N3O7S MW597.6 g/mol

[(3R)-2-[(11S)-7,8-difluoro-6,11-dihydrobenzo[c][1]benzothiepin-11-yl]-9,12-dioxospiro[5-oxa-1,2,8-triazatricyclo[8.4.0.0^3,8]tetradeca-10,13-diene-6,1'-cyclopropane]-11-yl]oxymethyl methyl carbonate

[(3R)-2-[(11S)-7,8-difluoro-6,11-dihydrobenzo[c][1]benzothiepin-11-yl]-9,12-dioxospiro[5-oxa-1,2,8-triazatricyclo[8.4.0.03,8]tetradeca-10,13-diene-6,1'-cyclopropane]-11-yl]oxymethyl methyl carbonate

({(12'aR)-12'-[(11S)-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl]-6',8'-dioxo-6',8',12',12'a-tetrahydro-1'H,4'H-spiro[cyclopropane-1,3'-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazin]-7'-yl}oxy)methyl methylcarbonate
antiviral, GP 681, Jiangxi Qingfeng Pharmaceutical, influenza A, INFLUENZA B, Cap-dependent endonuclease-IN-3, A72V8WPZ9F

Suraxavir marboxil (GP681) is an oral antiviral prodrug developed by Jiangxi Qingfeng Pharmaceutical for treating acute, uncomplicated influenza A and B virus infections.

Key Details

• Mechanism of Action: It converts into its active metabolite, GP1707D07, which acts as a cap-dependent endonuclease (CEN) inhibitor by targeting the polymerase acidic (PA) protein subunit of the influenza virus RNA polymerase. This stops viral gene transcription and replication.
• Administration: Designed as a single-dose oral therapy (typically evaluated at 40 mg).
• Efficacy: In phase 3 clinical trials, a single dose administered within 48 hours of symptom onset reduced the median time to symptom alleviation to 42.0 hours (compared to 63.0 hours for placebo) and rapidly lowered viral load.
• Safety Profile: Adverse events are mostly mild to moderate and comparable to placebo, with low rates of acquired resistance (such as I38T PA variants).

• OriginatorJiangxi Qingfeng Pharmaceutical
• ClassAntivirals; Carbonates; Cyclopropanes; Dibenzothiepins; Ethers; Fluorobenzenes; Ketones; Morpholines; Pyridones; Small molecules; Spiro compounds; Triazines
• Mechanism of ActionRNA-dependent RNA polymerase inhibitors
• RegisteredInfluenza virus infections
• 28 Nov 2025Capital Medical University initiates enrolment in a phase III trial for Influenza virus infections (In children, In adults, In the elderly) in China (PO) (NCT07236814)
• 01 Aug 2025Jiangxi Kerui Pharmaceutical plans a phase III trial for Influenza virus infections (In Children) in August 2025 (PO, suspension) (NCT07113392)
• 31 Mar 2025Chemical structure information added.

PAT

US20230144122

https://patentscope.wipo.int/search/en/detail.jsf?docId=US397715831&_cid=P20-MV61ZK-74389-1

Preparation of Compound of formula (10): Compound of formula (11) (388 mg, 1 mmol) was dissolved in 3 mL dichloromethane and added with 1 mL trifluoroacetic acid, and the mixture was stirred at room temperature for 3 hours. TLC showed the reaction was complete, and the mixture was added with 3N sodium hydroxide solution to adjust pH=9-10. The mixture was extracted with dichloromethane, and organic phases were merged, washed with saturated salt solution, dried, and concentrated to give 270 mg solid, which was directly used in the next step.

Preparation of Compound of formula (8): Compound of formula (9) (1.0 g, 7.8 mmol) was dissolved in 10 mL anhydrous tetrahydrofuran, and dropwise added with 2.5M n-butyllithium solution (3.1 mL, 7.8 mmol) slowly at −78° C. and under nitrogen protection. After addition, the mixture was stirred and reacted at the temperature for 2 hours. Then allyl formate (0.94 g, 7.8 mmol) was dropwise added. After addition, the mixture was stirred and reacted for 2 hours, and TLC showed the raw materials were substantially completely reacted, and then the reaction mixture was poured into saturated ammonium chloride solution to quench, and then extracted with ethyl acetate (15 mL×3). The organic phases were merged, dried over anhydrous sodium sulfate, and concentrated to dry to give 1.65 g oily product.

Preparation of Compound of formula (7): Compound of formula (8) (1.65 g, 7.8 mmol) was dissolved in 15 mL anhydrous tetrahydrofuran, and dropwise added with 1M diisobutylaluminum hydride solution (11.7 mL, 11.7 mmol) slowly at −78° C. and under nitrogen protection. After addition, the mixture was stirred and reacted at the temperature for 2 hours. TLC showed the raw materials were substantially completely reacted, and then the reaction mixture was poured into saturated potassium sodium tartrate solution to quench, and then extracted with ethyl acetate (20 mL×3). The organic phases were merged, dried over anhydrous sodium sulfate, and concentrated to dry to give 1.57 g oily product.

Preparation of Compound of formula (6): Compound of formula (7) (1.57 g, 7.4 mmol) was dissolved in 15 mL methanol, and p-toluenesulfonic acid monohydrate (140 mg, 0.74 mmol) was added, and the mixture was stirred at room temperature overnight. TLC showed the raw materials were substantially completely reacted, and then the mixture was added with saturated sodium bicarbonate solution to adjust to be neutral, and concentrated. The residue was separated by column chromatography to give 0.86 g yellow oily product.

Preparation of Compound of formula (5): Compound of formula (10) (270 mg, 0.94 mmol) and Compound of formula (6) (255 mg, 1.13 mmol) were dissolved in 5 mL acetonitrile. 1M solution of tin tetrachloride in dichloromethane (1.4 mL, 1.41 mmol) was added dropwise under nitrogen protection and at −20° C. After addition, the mixture was stirred and reacted at the temperature for 3 hours. The mixture was added with saturated sodium bicarbonate solution, stirred for 30 min, and stood to layer, and the aqueous phase was extracted with dichloromethane. The organic phases were merged, washed with saturated salt solution, dried, and concentrated to give 428 mg crude product.

Preparation of Compound of formula (4): Compound of formula (5) (428 mg, 0.89 mmol) was dissolved in 5 mL tetrahydrofuran, and tetrakis(triphenylphosphine)palladium (104 mg, 0.09 mmol) and morpholine (774 mg, 8.9 mmol) were added and reacted at room temperature for 2 hours. The reaction was shown complete through TLC spot plate analysis. The mixture was concentrated, and the residue was separated by column chromatography to give 216 mg product.

Preparation of Compound of formula (3): Compound of formula (4) (216 mg, 0.61 mmol) and Compound of formula (12) (242 mg, 0.92 mmol) were reacted at 100° C. for 3 hours in 3 mL solution of T 3P in ethyl acetate under airtight condition. The mixture was cooled, diluted with saturated NaHCO3, and then extracted with ethyl acetate. The organic phases were merged, dried and concentrated, and separated by column chromatography to give 200 mg crude product, which was separated by chiral column to give 40 mg product.

Preparation of Compound of formula (2): Compound of formula (3) (40 mg, 0.067 mmol) and lithium chloride (20 mg, 0.48 mmol) were reacted at 100° C. for 3 hours in 1 mL DMA. After the reaction finished, the mixture was diluted with 10 mL water, and added with 2N hydrochloric acid to adjust pH to 3-4. The mixture was filtered, and the solid was pumped to dry to give 25 mg product. 1HNMR (400 MHz, CDCl 3) δ: 7.05-7.15 (m, 5H), 6.85 (m, 1H), 6.70 (d, 1H, J=7.6 Hz), 5.78 (d, 1H, J=7.6 Hz), 5.3 (m, 2H), 4.69 (d, 1H, J=6.8 Hz), 4.17 (d, 1H, J=14 Hz), 4.09 (d, 1H, J=14 Hz), 3.90 (m, 1H), 3.69 (m, 1H), 3.44 (d, 1H, J=15.2 Hz), 0.95 (m, 1H), 0.74 (m, 3H); ESI-MS m/z (M+H) + 510.1.

Preparation of Compound of formula (1): Compound of formula (2) (40 mg, 0.08 mmol), chloromethyl methyl carbonate (25 mg, 0.2 mmol), potassium carbonate (28 mg, 0.2 mmol) and potassium iodide (3 mg, 0.02 mmol) were reacted at 60° C. for 5 hours in 1 mL N,N-dimethylacetamide. The reaction was shown complete through TLC spot plate analysis, the mixture was added with water to quench, and added with 1N diluted hydrochloric acid to adjust pH to 3-4. The solid was filtered, dried, and separated by column chromatography to give 35 mg product, which was the compound of formula (1), and the solid was analyzed to be amorphous and used as the starting material for preparing various crystal forms in subsequent embodiments. 1HNMR (400 MHz, DMSO-d6) δ: 7.40-7.42 (m, 2H), 7.25 (d, 1H, J=7.6 Hz), 7.15 (m, 1H), 7.10 (m, 1H), 7.00 (d, 1H, J=7.2 Hz), 6.84 (t, 1H, J=7.6 Hz), 5.75 (m, 4H), 5.43 (d, 1H, J=16.4 Hz), 4.57 (dd, 1H, J=3.2, 9.6 Hz), 3.96-4.03 (m, 3H), 3.73 (s, 3H), 3.51 (t, 1H, J=10.0 Hz), 3.41 (s, 1H), 0.75 (t, 2H, J=8.4 Hz), 0.50 (m, 2H); ESI-MS m/z (M+H) + 598.1.

PAT

US20190367517

https://patentscope.wipo.int/search/en/detail.jsf?docId=US278278529&_cid=P20-MV6251-78985-1

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References

///////////suraxavir marboxil, anax labs, antiviral, GP 681, Jiangxi Qingfeng Pharmaceutical, influenza A, INFLUENZA B, Cap-dependent endonuclease-IN-3, A72V8WPZ9F

#suraxavir marboxil, #anax labs, #antiviral, #GP 681, #Jiangxi Qingfeng Pharmaceutical, #influenza A, #INFLUENZA B, #Cap-dependent endonuclease-IN-3, #A72V8WPZ9F

Sumonerimod

 

Sumonerimod

CAS 2433782-42-2

MFC25H26F3NO3 MW445.5

3-(5-((4-cyclopentyl-3-(trifluoromethyl)benzyl)oxy)-3-methyl-1H-indol-2-yl)propanoic acid,

• 1H-Indole-2-propanoic acid, 5-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-3-methyl-
• 5-[[4-Cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-3-methyl-1H-indole-2-propanoic acid
• 3-[5-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-3-methyl-1H-indol-2-yl]propanoic acid

3-(5-{[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy}-3-methyl-1Hindol-2-yl)propanoic acid
sphingosine-1-phosphate receptor 1 agonist, immunomodulator, S1P1 agonist 6, 49KZ2L5DUV, CBP-307, Icanbelimod, CBP 307

Sumonerimod is a selective Sphingosine-1-phosphate receptor 1 ($\text{S1P}_1$) agonist developed primarily for autoimmune and inflammatory diseases (such as ulcerative colitis and Crohn's disease).

PAT

WO2020114475A1

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020114475&_cid=P12-MUZ8I1-71620-1

Reference Example 72: Preparation of Intermediate I-74

ntermediate I-73 (4.3 g) was dissolved in dichloromethane (30 mL). The reaction mixture was cooled to -40 °C, and a dichloromethane solution (50 mL) of N-bromosuccinimide (NBS, 1.98 g, 11.1 mmol) was slowly added dropwise. After the addition was complete, the reaction mixture was heated to 0 °C and stirred at 0 °C for 2 h. The reaction mixture was washed with water (20 mL), the organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the residue. The residue was purified by silica gel chromatography to obtain intermediate I-74.

[0395]

LC-MS(ESI)[M-H] ^-464。

[0396]Reference Example 73: Preparation of Intermediate I-75

Intermediate I-74 (1.0 g, 2.15 mmol) was dissolved in a mixture of 1,4-dioxane and water (10 mL, 4:1) at room temperature, followed by the addition of methylboric acid (1.29 g, 21.46 mmol), potassium carbonate (0.89 g, 6.44 mmol), and tetrakis(triphenylphosphine)palladium (243 mg, 0.21 mmol). The reaction mixture was stirred at 90 °C for 7 h under argon protection. The reaction mixture was cooled to room temperature, filtered, and concentrated under reduced pressure to obtain the residue. The residue was dissolved in dichloromethane (20 mL), and water (10 mL) was added. The aqueous phase was separated and extracted with dichloromethane (20 mL × 2). The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the residue. The residue was purified by silica gel chromatography to obtain intermediate I-75.

[0399]

LC-MS(ESI)[M-H] ^-400.0.

[0400]Reference Example 74: Preparation of Intermediate I-76

Intermediate I-75 (470 mg, 1.17 mmol) was dissolved in tetrahydrofuran (10 mL) at room temperature, and ethoxycarbonylmethylene triphenylphosphine (490 mg, 1.41 mmol) was added. The reaction mixture was stirred at 80 °C for 15 h. After cooling the reaction solution to room temperature, the organic solvent was removed by concentration under reduced pressure to obtain the residue. The residue was purified by reversed-phase preparative liquid chromatography to obtain intermediate I-76.

[0403]

LC-MS(ESI)[M-H] ^-470.2.

[0404]Reference Example 75: Preparation of Intermediate I-77

Intermediate I-76 (110 mg, 0.23 mmol) was dissolved in ethyl acetate (2 mL), and PtO₂ (50 mg) was added

_. The reaction mixture was stirred at room temperature for 2 h under a hydrogen atmosphere. After filtration, the filtrate was concentrated under reduced pressure to give intermediate I-77.

[0407]

LC-MS(ESI)[M+H] ⁺474.2.

Example 16: Preparation of Compound 16

Intermediate I-77 (110 mg) was dissolved in tetrahydrofuran (2 mL), and lithium hydroxide monohydrate (29 mg, 0.70 mmol) and water (0.5 mL) were added. After stirring at room temperature for 3 h, the reaction solution was purified by preparative liquid chromatography to obtain compound 16.

[0809]

LC-MS(ESI)[M-H] ^-444.1.

[0810]

¹H NMR(400MHz,MeOH-d ₄)δ7.71(s,1H),7.66(d,J＝8.2Hz,1H),7.57(d,J＝8.2Hz,1H),7.13(d,J＝8.7Hz,1H),6.98(d,J＝2.3Hz,1H),6.76(dd,J＝8.7,2.4Hz,1H),5.10(s,2H),3.41–3.35(m,1H),3.00(t,J＝7.7Hz,2H),2.63(t,J＝7.7Hz,2H),2.18(s,3H),2.10–2.02(m,2H),1.95–1.86(m,2H),1.78–1.60(m,4H).

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#MedicinalChemistry, #DrugDiscovery, #OrganicSynthesis, #ChemicalLibrary, #BuildingBlocks, #SARStudies, #ChemistryInnovation, #medchem, #Drugdevelopment, #Biotech, #Biotechnology, #AnaxLaboratories, #Pharma

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References

///////////sumonerimod, anax labs, sphingosine-1-phosphate receptor 1 agonist, immunomodulator, S1P1 agonist 6, 49KZ2L5DUV, CBP-307, Icanbelimod, CBP 307

#sumonerimod, #anax labs, #sphingosine-1-phosphate receptor 1 agonist, #immunomodulator, #S1P1 agonist 6, #49KZ2L5DUV, #CBP-307, #Icanbelimod, #CBP 307