Becondogrel

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Becondogrel

CAS 1416696-44-0

MF C16H16ClNO3S, MW 337.821

2-OXO-CLOPIDOGREL, (.ALPHA.S,7AS)-

(4S)-2-Oxoclopidogrel

THIENO(3,2-C)PYRIDINE-5(4H)-ACETIC ACID, .ALPHA.-(2-CHLOROPHENYL)-2,6,7,7A-TETRAHYDRO-2-OXO-, METHYL ESTER, (.ALPHA.S,7AS)-

Methyl (S)-(2-chlorophenyl)[(7aS)-2-oxo-2,6,7,7atetrahydrothieno[ 3,2-c]pyridin-5(4H)-yl]acetate

methyl (S)-(2-chlorophenyl)[(7aS)-2-oxo-2,6,7,7atetrahydrothieno[3,2-c]pyridin-5(4H)-yl]acetate
platelet aggregation inhibitor, D7X6820P1N, Copidogrel oxide, (4S)-2-Oxoclopidogrel

Becondogrel is an antiplatelet medication and an irreversible P2Y12 receptor antagonist. It is chemically known as 2-oxoclopidogrel, which is a direct metabolic intermediate of the widely used drug clopidogrel (Plavix).

Key Characteristics

Mechanism of Action: It prevents blood cells (platelets) from sticking together, which helps inhibit the formation of blood clots (thrombosis).
Relationship to Clopidogrel: Standard clopidogrel is a prodrug that requires two metabolic steps in the liver to become active. Becondogrel is designed to bypass the first of these steps, potentially reducing the individual variability in effectiveness seen with clopidogrel due to genetic differences in liver enzymes (CYP450).
Clinical Status: As of early 2025, becondogrel was included in the World Health Organization’s (WHO) proposed International Nonproprietary Name (INN) list, indicating its development for medical use

SYN

Example 3

(2S)-Methyl 2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5(2H,4H,6H)-yl)-2-(2-chlorophenyl)-acetate (IV-1)

[0042] 58.1 g (0.15 mol) of (R)-methyl 2-(2-chlorophenyl)-2-(4-nitrophenylsulfonyloxy)-acetate (II-1), 32.3 g (0.17 mol) of 5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride (III-1), and 37.8g (0.38 mol) of potassium bicarbonate were added to 500 ml of acetonitrile. The reaction was stirred under a nitrogen atmosphere at room temperature for 26 hrs. The reaction solution was allowed to stand and the insoluble material was filtered off, to obtain a dark red mother liquor. The solvent was evaporated under reduced pressure, and 35.4 g of an oil product was obtained after purification by flash column chromatography (petroleum ether:ethyl acetate = 4:1). Yield 70%. Recrystalization from ethanol afforded 18.1 g of a pure product (IV-1) as a white solid. mp: 146-148°C, ee = 97.5%, [α] _D ¹⁹ = +114.0° (c 0.5, MeOH); ¹H-NMR (300 MHz, CDCl ₃) δ 1.79-1.93 (m, 1 H), 2.30-2.40 (m, 1 H), 2.56-2.70 (m, 1 H), 3.00-3.27 (m, 2 H), 3.72 (s, 3 H), 3.79-3.93 (m, 1 H), 4.12-4.19 (m, 1 H), 4.89 (d, 1 H, J= 5.6 Hz), 6.00 (d, 1 H, J = 5.2 Hz), 7.26-7.50 (m, 4 H); ¹³C-NMR (75 MHz, CDCl ₃) δ 33.9, 34.0, 49.0, 49.7, 51.1, 51.6, 52.2, 52.4, 67.3, 76.6, 77.0, 77.4, 126.6, 126.8, 127.2, 129.8, 130.1, 132.7, 134.8, 167.2, 167.4, 170.8, 198.6; ESI-MS m/ z 338.1 [M+H] ⁺; HRMS Calcd for C ₁₆H ₁₇NO ₃SCl [M+H] ⁺ m/ z 338.0618, found 338.0626.

SYN

PAT

WO2020233226 B CRYSTAL FORM OF TETRAHYDROTHIENOPYRIDINE COMPOUND, PREPARATION METHOD THEREFOR, COMPOSITION AND APPLICATION

. The chemical name of the compound with the Equation I structure is: (S)-2-(2-chlorophenyl)-2-((S)-2-oxo-2,6,7,7a-tetrahydrothiophene[3,2-c]and pyridine-5(4H))yl)methyl acetate.