- 【药物名称】Cetraxate hydrochloride, DV-1006, Neuer
- 【化学名】trans-3-[4-[4-(Aminomethyl)cyclohexylcarbonyloxy]phenyl]propionic acid hydrochloride
- 【CAS登记号】
- 【结构式】
- 【分子式】C17-H23-N-O4.Cl-H
- 【分子量】341.8326
- 【原研厂家】Daiichi Pharmaceutical (Originator)
- 【作用类别】Antiulcer Drugs, GASTROINTESTINAL DRUGS
- 【研发状态】Launched
- 【合成情况】
- 〖来源〗J Med Chem
- 〖合成路线〗
- 〖标题〗Medicinal chemical studies on antiplasmin drugs. 4. Chemical modification of trans-4-aminomethylcyclohexacarboxylic acid and its effect on antiplasmin activity
- 〖合成方法〗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.
- 〖作者〗Atsuji, O.; et al.
- 〖参考〗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
- 〖出处〗J Med Chem1972,15,(3):247-255
- 〖备注〗
- 〖来源〗Drugs Fut
- 〖合成路线〗
- 〖标题〗Cetraxate
- 〖合成方法〗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.
- 〖作者〗Roberts, P.J.; Castaer, J.
- 〖参考〗Roberts, P.J.; Castaer, J.; Cetraxate. Drugs Fut 1977, 2, 8, 504
- 〖出处〗Drugs Fut1977,2,(8):504
- 〖备注〗Synthesis It can be obtained in two different ways: 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 HOAc (1,2) (Scheme 07020201a). 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 (1) (Scheme 07020202a). 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 (3) (Scheme 07020203a). Description Crystals, m.p. 280 C ; HCl salt, m.p. 238-40 C (dec.); Methanesulfonate salt, m.p. 213-5 C. Manufacturer Daiichi Seiyaku Co. References 1. 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 2. Kitahara, S. (Daiichi Seiyaku Co., Ltd.); JP 48075547 3. Kitahara, S. (Daiichi Seiyaku Co., Ltd.); JP 48078143
- 〖来源〗J Med Chem
- 〖合成路线〗
- 〖标题〗Medicinal chemical studies on antiplasmin drugs. 4. Chemical modification of trans-4-aminomethylcyclohexacarboxylic acid and its effect on antiplasmin activity
- 〖合成方法〗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.
- 〖作者〗Atsuji, O.; et al.
- 〖参考〗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
- 〖出处〗J Med Chem1972,15,(3):247-255
- 〖备注〗
- 〖来源〗Drugs Fut
- 〖合成路线〗
- 〖标题〗Cetraxate
- 〖合成方法〗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.
- 〖作者〗Roberts, P.J.; Castaer, J.
- 〖参考〗Roberts, P.J.; Castaer, J.; Cetraxate. Drugs Fut 1977, 2, 8, 504
- 〖出处〗Drugs Fut1977,2,(8):504
- 〖备注〗Synthesis It can be obtained in two different ways: 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 HOAc (1,2) (Scheme 07020201a). 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 (1) (Scheme 07020202a). 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 (3) (Scheme 07020203a). Description Crystals, m.p. 280 C ; HCl salt, m.p. 238-40 C (dec.); Methanesulfonate salt, m.p. 213-5 C. Manufacturer Daiichi Seiyaku Co. References 1. 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 2. Kitahara, S. (Daiichi Seiyaku Co., Ltd.); JP 48075547 3. Kitahara, S. (Daiichi Seiyaku Co., Ltd.); JP 48078143
- 〖来源〗Drugs Fut
- 〖合成路线〗
- 〖标题〗Cetraxate
- 〖合成方法〗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.
- 〖作者〗Roberts, P.J.; Castaer, J.
- 〖参考〗Roberts, P.J.; Castaer, J.; Cetraxate. Drugs Fut 1977, 2, 8, 504
- 〖出处〗Drugs Fut1977,2,(8):504
- 〖备注〗Synthesis It can be obtained in two different ways: 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 HOAc (1,2) (Scheme 07020201a). 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 (1) (Scheme 07020202a). 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 (3) (Scheme 07020203a). Description Crystals, m.p. 280 C ; HCl salt, m.p. 238-40 C (dec.); Methanesulfonate salt, m.p. 213-5 C. Manufacturer Daiichi Seiyaku Co. References 1. 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 2. Kitahara, S. (Daiichi Seiyaku Co., Ltd.); JP 48075547 3. Kitahara, S. (Daiichi Seiyaku Co., Ltd.); JP 48078143
- 〖来源〗JP 48075547
- 〖合成路线〗
- 〖标题〗
- 〖合成方法〗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.
- 〖作者〗Kitahara, S.
- 〖参考〗Kitahara, S.; . JP 48075547
- 〖出处〗JP 48075547,,():
- 〖备注〗
- 〖来源〗JP 48078143
- 〖合成路线〗
- 〖标题〗
- 〖合成方法〗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.
- 〖作者〗Kitahara, S.
- 〖参考〗Kitahara, S.; . JP 48078143
- 〖出处〗JP 48078143,,():
- 〖备注〗
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