药物详细合成路线

Name	Cetraxate hydrochloride;DV-1006;Neuer
Chemical Name	trans-3-[4-[4-(Aminomethyl)cyclohexylcarbonyloxy]phenyl]propionic acid hydrochloride
CAS	27724-96-5
Related CAS
Formula	C17H24ClNO4
Structure
Formula Weight	341.83813
Stage	上市
Company	Daiichi Pharmaceutical (Originator)
Activity/Mechanism	Antiulcer Drugs, GASTROINTESTINAL DRUGS
Syn. Route	3

Route 1 by condensation of trans-4-toluenesulfonylaminomethylcyclohexane carbonyl chloride (i) and benzyl 4-hydroxyphenylpropionate (ii) by means of et3n and hot benzene followed by debenzylation using h2 over pd/c in acoh. List of intermediates No. 2-methyl-1-cyclopentene-1-carbaldehyde (i) 2,6-dioxoheptanoic acid (ii) Reference 1:     kitahara, s.; jp 48075547 . Reference 2:     roberts, p.j.; castaner, j.; cetraxate. drugs fut 1977, 2, 8, 504. Reference 3:     atsuji, o.; et al.; medicinal chemical studies on antiplasmin drugs. 4. chemical modification of trans-4-aminomethylcyclohexacarboxylic acid and its effect on antiplasmin activity. j med chem 1972, 15, 3, 247-255. Route 2 by condensation of trans-4-cyanocyclohexanecarbonyl chloride (iii) and the benzyl ester (ii) by means of triethylamine in hot benzene followed by debenzylation using h2 over pd/c in acetic acid giving the cyanoester (iv), which is then reduced with h2 over raney-ni in ethyl acetate - ethanol - water. List of intermediates No. 2,6-dioxoheptanoic acid (ii) (3as,14bs)-2-ethyl-1,5,6,8,9,14b-hexahydro-4h-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol (iii) (3ar,14bs)-2-methoxy-1,5,6,8,9,14b-hexahydro-4h-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-yl 2,6-dioxoheptanoate (iv) Reference 1:     roberts, p.j.; castaner, j.; cetraxate. drugs fut 1977, 2, 8, 504. Reference 2:     atsuji, o.; et al.; medicinal chemical studies on antiplasmin drugs. 4. chemical modification of trans-4-aminomethylcyclohexacarboxylic acid and its effect on antiplasmin activity. j med chem 1972, 15, 3, 247-255. Route 3 by condensation of trans-4-toluenesulfonylaminomethylcyclohexane carbonyl chloride (i) and ter-butyl-4-hydroxyphenylpropionate (v) and performing the hydrolysis with hcl - acetic acid at room temperature. List of intermediates No. 2-methyl-1-cyclopentene-1-carbaldehyde (i) 1-[(1s,3ar,14bs)-2-methoxy-1,5,6,8,9,14b-hexahydro-4h-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-yl] 4-methyl 2-hydroxy-2-(4-oxopentyl)succinate (v) Reference 1:     kitahara, s.; jp 48078143 . Reference 2:     roberts, p.j.; castaner, j.; cetraxate. drugs fut 1977, 2, 8, 504.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名；英文名Cetraxate hydrochloride;DV-1006;Neuer；CAS[27724-96-5]

有机化学人才网，招聘求职的最佳选择！