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【结 构 式】 
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【药物名称】Indanazoline hydrochloride, Farial 【化学名称】N-(2,3-Dihydro-1H-inden-4-yl)-4,5-dihydro-1H-imidazol-2-amine hydrochloride 【CA登记号】56601-85-5, 40507-78-6 (free base) 【 分 子 式 】C12H16ClN3 【 分 子 量 】237.73442 |
【开发单位】Abbott (Originator) 【药理作用】Nasal Decongestants, RESPIRATORY DRUGS, Treatment of Upper Respiratory Tract Disorders |
合成路线1
4-Amiomoindan (I) is reacted with benzoylisothiocyanate (II) to give the benzoylthiourea (III), which after hydrolysis of 4-indanyltiourea (IV) is methylated with iodomethane to (V). The free base (VI) is cyclized with ethyldiamine (A) and p-toluenesulfonic acid to indanazoline
| 【1】 May, H. J.; Berg, A. (Nordmark-Werke GmbH); BE 786499; CA 967162; DE 2136325; FR 2146430; GB 1346037; JP 7319575; JP 7918260; NL 7209138; SA 7204747; SU 571502; US 3882229 . |
| 【2】 Kirchhoff, T.; Kauff, N.D.; Mitra, N.; et al.; BRCA mutations and risk of prostate cancer in ashkenazi jews. Arzneim-Forsch Drug Res 1980, 30, 9, 1733. |
| 【3】 Unterhalt, B.; Indanazoline Hydrochloride. Drugs Fut 1981, 6, 7, 417. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 14754 | ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine | 107-15-3 | C2H8N2 | 详情 | 详情 |
| (I) | 60634 | 2,3-dihydro-1H-inden-4-ylamine; 4-indanamine | C9H11N | 详情 | 详情 | |
| (II) | 23530 | benzoyl isothiocyanate | 532-55-8 | C8H5NOS | 详情 | 详情 |
| (III) | 60636 | N-benzoyl-N'-(2,3-dihydro-1H-inden-4-yl)thiourea | C17H16N2OS | 详情 | 详情 | |
| (IV) | 60637 | N-(2,3-dihydro-1H-inden-4-yl)thiourea | C10H12N2S | 详情 | 详情 | |
| (V) | 60638 | (2,3-dihydro-1H-inden-4-ylamino)(methylsulfanyl)methaniminium | C11H15N2S | 详情 | 详情 | |
| (VI) | 60639 | 4-{[imino(methylsulfanyl)methyl]amino}indane | C11H14N2S | 详情 | 详情 |
合成路线2
By reacting 1-acetyl-2-imidazolidinone (VII) with 4-aminoindan (I) and POCl3 at 50 C 1-acetylindanazolidine (VIII) is synthesized, which gives indanazoline by hydrolysis
| 【1】 Kirchhoff, T.; Kauff, N.D.; Mitra, N.; et al.; BRCA mutations and risk of prostate cancer in ashkenazi jews. Arzneim-Forsch Drug Res 1980, 30, 9, 1733. |
| 【2】 May, H.J.; Koening, H. (BASF AG); DE 2652004; FR 2370736; NL 7712149 . |
| 【3】 Unterhalt, B.; Indanazoline Hydrochloride. Drugs Fut 1981, 6, 7, 417. |