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【结 构 式】

【药物名称】AH-9700

【化学名称】1-[2-(6,7-Dimethyl-3,4-dihydro-2-naphthalenyl)ethyl]pyrrolidine fumarate

【CA登记号】184638-09-3 (free base), 184639-27-8 (hydrochloride)

【 分 子 式 】C22H29NO4

【 分 子 量 】371.48073

【开发单位】Dainippon Pharmaceutical (Originator)

【药理作用】RENAL-UROLOGIC DRUGS, Urinary Incontinence Therapy, Muscarinic M3 Antagonists

合成路线1

Mannich reaction of 6,7-dimethyltetralone (I) with dimethylamine and formaldehyde provided amino ketone (II). Subsequent quaternization of (II) with MeI in acetone gave ammonium salt (III), that was further displaced by KCN yielding nitrile (IV). Acidic hydrolysis of the cyano group of (IV) produced carboxylic acid (V). This was then coupled with pyrrolidine (VI) employing BOP reagent to furnish amide (VII). Reduction of the ketone and amide functions of (VII) by means of vitride?in toluene afforded amino alcohol (VIII). After alcohol (VIII) dehydration with ethanolic HCl, the title compound was isolated as the fumarate salt.

1 Kai, N.; Kanehira, A.; Morie, T.; Hino, K.; Kawashima, K.; Shimizu, I.; Akiyama, K. (Dainippon Pharmaceutical Co., Ltd.); 1-[omega-(3,4-Dihydro-2-naphthalenyl)alkyl]cyclic amine derivs., process for producing the same, and medicinal compsn. containing the same. EP 0825180; US 5847159; WO 9633169 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 41589 6,7-dimethyl-3,4-dihydro-1(2H)-naphthalenone C12H14O 详情 详情
(II) 41590 2-[(dimethylamino)methyl]-6,7-dimethyl-3,4-dihydro-1(2H)-naphthalenone C15H21NO 详情 详情
(III) 41591 (6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)-N,N,N-trimethylmethanaminium iodide C16H24INO 详情 详情
(IV) 41592 2-(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)acetonitrile C14H15NO 详情 详情
(V) 41593 2-(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)acetic acid C14H16O3 详情 详情
(VI) 11376 Pyrrolidine 123-75-1 C4H9N 详情 详情
(VII) 41594 6,7-dimethyl-2-[2-oxo-2-(1-pyrrolidinyl)ethyl]-3,4-dihydro-1(2H)-naphthalenone C18H23NO2 详情 详情
(VIII) 41595 6,7-dimethyl-2-[2-(1-pyrrolidinyl)ethyl]-1,2,3,4-tetrahydro-1-naphthalenol C18H27NO 详情 详情
Extended Information