Olisutrigine bromide

Cas 1393836-45-7

MF C25H35BrN2 MW443.5 g/mol

N-[2-[(2R)-1,1-dimethylpiperidin-1-ium-2-yl]ethyl]-N-(2-methylphenyl)-2,3-dihydro-1H-inden-2-amine bromide

(2R)-2-{2-[N-(2,3-dihydro-1H-inden-2-yl)-2-methylanilino]ethyl}-1,1-dimethylpiperidin-1-ium bromide
sodium channel blocker, analgesic, ASN008, ASN 008, EN 3427, 0M9Q318030

Olisutrigine bromide (also known as ASN-008 or EN3427) is an investigational, permanently charged sodium channel blocker being studied for its potent, long-lasting analgesic (pain-relieving) properties.

Key Characteristics

• Mechanism of Action: It acts as a membrane-impermeant sodium channel blocker. Because it carries a permanent cationic charge, it cannot easily cross healthy cell membranes on its own.
• Targeted Delivery: It often requires a “vehicle” or a combination drug (like lidocaine) to activate specific channels (such as TRP channels), allowing olisutrigine entry into pain-sensing neurons where it becomes entrapped and blocks pain signaling.
• Efficacy: Rodent pain models demonstrate that its analgesic effects are significantly longer-lasting than lidocaine alone.
• Chemical Profile: Its molecular formula is C₂₅H₃₅BrN₂ with a molecular weight of 443.5 g/mol, and its CAS registry number is 1393836-45-7.

Current Status

• Investigational Drug: It is not approved for human or veterinary medical use and remains in the research and development phase.
• Availability: It is strictly available as a reference standard compound for laboratory and preclinical research through chemical suppliers like MedChemExpress and BenchChem.

A Study to Evaluate the Anti-pruritic Effectiveness of ASN008 in Adults With Mild to Moderate Atopic Dermatitis

CTID: NCT05870865

Phase: Phase 2

Status: Completed

Date: 2025-05-16

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2012112969&_cid=P11-MRILQZ-81481-1

Example 43: General Procedure M – Preparation of (R)-1,1 -dimethyl-2-[2-((indan-2-yl)(2-methylphenyl)amino)ethyl]piperidinium bromide

Alcohol 37b was synthesized as previouslydescribed (Tetrahedron 2007, 63, 3000-3005)

To a 250 mL round bottom flask was charged 2-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester 37b (5.0 g, 21.80 mmol), dichloromethane (7.50 mL), a solution of KBr (0.52 g, 4.36 mmol) in 2.0 mL of water and TEMPO (0.1 g, 0.64 mmol). The mixture was cooled to about -5 °C. A solution of NaOCl (31.1 mL, 5.25%, 24.1 mmol) was added slowly over 20 minutes while maintaining the temperature at 0 °C. The mixture was further stirred at 0°C for 20 minutes. The organic layer was separated, and the aqueous layer was extracted with

dichloromethane. The combined dichloromethane extract was washed with water (50 mL), followed by brine. After drying over MgSO₄, the mixture was filtered and concentrated. The crude was purified with silica gel column chromatography to give product 38b (4.1 g, 83%) as colorless oil.

O

To a clean and dry 250 mL round bottom flask was charged sodium triacetoxyborohydride (5.59 g, 26.40 mmol), 4 A molecular sieves (10.0 g), amine 7e (7.37 g, 33.00 mmol) and dichloromethane (20.0 mL). The mixture was stirred and cooled to about 0 °C, and a solution of aldehyde 38b (5.0 g, 22.00 mmol) in 40 mL of dichloromethane was added. The mixture was then stirred further at 0 °C for about 1 hour and at ambient temperature for an additional 40 minutes. The reaction mixture was quenched with aqueous saturated NaHCO₃ (100 mL). After separation of organic layer, the mixture was extracted with dichloromethane. After drying over MgSO₄, the organic layer was concentrated. The crude product was purified by silica gel column chromatography to give product 40f (7.2 g, 75.3%) as colorless oil.

To a clean and dry 250 mL round bottom flask was charged lithium aluminum hydride (1.53 g, 40.27 mmol) and THF (30.0 mL). The mixture was heated to reflux. A solution of carbamate 40f (7.0 g, 16.11 mmol) in THF (40.0 mL) was added dropwise over 5 minutes. After refluxing for 15 h, the reaction mixture was cooled to 0 °C, and water (1.55 mL) was added slowly and carefully, followed by THF (100 mL) and 15% NaOH (1.55 mL). After stirring the mixture at room temperature for 1.0 h, MgSO₄ was added, and the mixture was stirred further for 15 minutes. The mixture was filtered and concentrated to obtain the crude product, which was purified by silica gel column chromatography to afford product 11e (4.7 g, 84%) as pale yellow oil. Optical purity by chiral HPLC: 99.3% ee.

To a clean and dry 250 mL round bottom flask was charged diamine 11e (4.70 g, 13.49 mmol) and 1.07 M bromomethane in MTBE (126.0 mL, 134.8 mmol). After stirring at room temperature for 20 h, the reaction mixture was filtered. The solid cake was washed with MTBE to give the product (4.40 g, 73%) as white powder. Optical purity by chiral HPLC: 99.3% ee.

PAT

https://patentscope.wipo.int/search/en/detail.jsf;jsessionid=53D672FEEE9931FFC5F125D61A00D7FA.wapp1nB?docId=WO2026050699&_cid=P11-MRILJW-76628-1

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2025250498&_cid=P11-MRILME-78328-1

Compound 1 is described in WO2012/112969, wherein Compound 1 is reported at Example 43, and certain formulations of Compound 1 are described in WO2020/113050,

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References

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///////////olisutrigine bromide, anax labs, sodium channel blocker, analgesic, ASN008, ASN 008, EN 3427, 0M9Q318030