-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】2-Chlorobenzenesulfonic acid 3-[3-(amidinohydrazono)propoxy]-5-methylphenyl ester nitrate

【CA登记号】197959-48-1 (free base), 197958-62-6 (monohydrochloride)

【分子式】C₁₇H₂₀ClN₅O₇S

【分子量】473.89525

【开发单位】3-Dimensional (Originator)

【药理作用】Anticoagulants, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, Thrombin Inhibitors

合成路线1

2-Chlorobenzenesulfonyl chloride (I) was coupled to orcinol (II) to give sulfonate (III). Subsequent condensation of (III) with 3-benzyloxypropanol (IV) under Mitsunobu conditions afforded ether (V). After hydrogenolytic deprotection of the benzyl group, Swern oxidation of the resulting alcohol (VI) with DMSO and SO3-pyridine complex provided aldehyde (VII). The title amidinohydrazone was then obtained by treatment of (VII) with aminoguanidine nitrate (VIII).

参考文献中间体

【1】 Soll, R.M.; Lu, T.; Fedde, C.L.; Tomczuk, B.E.; Illig, C. (3-Dimensional Pharmaceuticals, Inc.); Amidinohydrazones as protease inhibitors. EP 0906091; JP 2000507588; US 5891909; WO 9736580 .
【2】 Tomczuk, B.E.; Stagnaro, T.P.; Fedde, C.L.; Lu, T.; Markotan, T.P.; Illig, C.R.; Soll, R.M. (3-Dimensional Pharmaceuticals, Inc.); Aminoguanidines and alkoxyguanidines as protease inhibitors. EP 0944590; WO 9823565 .

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)	30817	2-chlorobenzenesulfonyl chloride	2905-23-9	C₆H₄Cl₂O₂S	详情	详情
(II)	27257	5-Methyl-1,3-benzenediol; Orcinol	505-15-4	C₇H₈O₂	详情	详情
(III)	30818	3-hydroxy-5-methylphenyl 2-chlorobenzenesulfonate		C₁₃H₁₁ClO₄S	详情	详情
(IV)	14687	3-(benzyloxy)-1-propanol; 3-(Benzyloxy)propanol	4799-68-2	C₁₀H₁₄O₂	详情	详情
(V)	30819	3-[3-(benzyloxy)propoxy]-5-methylphenyl 2-chlorobenzenesulfonate		C₂₃H₂₃ClO₅S	详情	详情
(VI)	30820	3-(3-hydroxypropoxy)-5-methylphenyl 2-chlorobenzenesulfonate		C₁₆H₁₇ClO₅S	详情	详情
(VII)	30821	3-methyl-5-(3-oxopropoxy)phenyl 2-chlorobenzenesulfonate		C₁₆H₁₅ClO₅S	详情	详情
(VIII)	10015	1-Hydrazinecarboximidamide; Hydrazinecarboximidamide	79-17-4	CH₆N₄	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)