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. |
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