Impurity compound of nitrocaphane, and preparation method and application of impurity compound

A compound, the technology of nitro mustard, which is applied in the field of medicine, can solve the problems of unknown impurity structure and content uncertainty, unfavorable control or improvement of the quality standard of nitro mustard, and no preparation, so as to improve the safety of clinical medication and the preparation method is simple and efficient , the effect of improving quality standards

Inactive Publication Date: 2020-11-27
BEIJING ZHENDONG GUANGMING PHARMA RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the process of synthesizing nitro mustard or storing the finished nitro mustard product, unknown impurities will be formed, and the structure and content of the unknown impurities are uncertain, and there is no method for preparing the unknown impurities in the prior art, which is not conducive to the control or Improving the quality standard of nitroca mustard

Method used

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  • Impurity compound of nitrocaphane, and preparation method and application of impurity compound
  • Impurity compound of nitrocaphane, and preparation method and application of impurity compound
  • Impurity compound of nitrocaphane, and preparation method and application of impurity compound

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preparation example Construction

[0061] The embodiment of the present invention also provides a preparation method of the above-mentioned impurity compound of nitro mustard, comprising:

[0062] Utilize compound I and the compound that contains R group to carry out condensation reaction to obtain intermediate, wherein, the structural formula of compound I and described intermediate is shown as follows successively:

[0063] as well as Wherein, X represents a halogen, for example, any one of chlorine, bromine and iodine that can be used, and R is or R 1 and R 2 Each independently is an alkyl group, further is a C1-C8 alkyl group, preferably any one of methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl and pentyl; R 3 It is an amino protecting group, and the amino protecting group is a group that protects NH to prevent it from reacting, and the amino protecting group is R 3 The amino protecting group is Boc, Tfa, phenylacetyl or any of the.

[0064] It should be noted that although R in the examp...

Embodiment 1

[0079] This embodiment provides a compound shown in the following structural formula, namely the preparation process of compound 1:

[0080]

[0081] S1, condensation reaction

[0082] Weigh 10.00g of compound I, 4.72g of compound II, and 100ml of ethyl acetate into a 250ml three-neck flask, stir and heat up to 80°C, and reflux for 6h. TLC detected that the reaction was complete, and post-treatment was adding 30 ml of water to wash twice, and phase separation to obtain an organic phase. Add 100ml of n-heptane to the organic phase at room temperature and stir for crystallization for 2h. A large amount of off-white solid was precipitated, and the intermediate was obtained by suction filtration, 9.88 g of white solid, yield 93.73%.

[0083] The structural formulas of compound I, compound II and intermediates are as follows:

[0084] as well as

[0085] S2, decarboxylation reaction

[0086] Weigh 5.00g of the intermediate, add 20ml of concentrated hydrochloric acid (mo...

Embodiment 2- Embodiment 3

[0088] Embodiment 2-Example 3 provides a kind of preparation process of compound 1, its operation and the preparation process operation of compound 1 provided in embodiment 1, the difference is that the operating conditions are different, as follows:

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Abstract

The invention relates to the technical field of medicines, and in particular relates to an impurity compound of nitrocaphane, and a preparation method and application of the impurity compound. The structural formula of the impurity compound of nitrocaphane is shown in the specification, wherein R has two forms which are described in the specification. The invention provides a novel impurity compound of nitrocaphane which is beneficial to improving the quality standard of nitrocaphane, effectively controlling the quality of nitrocaphane and improving the clinical medication safety of nitrocaphane. Meanwhile, the preparation method is simple and efficient, raw materials are easy to obtain, the purity of the obtained nitrocaphane impurity compound is high, and batch production can be achieved. The method can be used for a reference substance of the impurity compound of nitrocaphane, so that the quality control of nitrocaphane is further improved.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular, to an impurity compound of nitrocardina, a preparation method and an application thereof. Background technique [0002] Nitromustine is an anticancer drug independently developed by my country. It belongs to nitrogen mustard drugs. It can inhibit the synthesis of DNA and RNA, and it is more significant for inhibiting DNA synthesis. It has a broad anti-tumor spectrum and low toxicity. At the same time, the treatment price of nitrocabinet is much lower than that of imported antineoplastic drugs, so its pharmacoeconomic value is high, and it is widely used in therapeutic drugs. Specifically, the structural formula of nitro mustard is as follows: [0003] [0004] In the process of synthesizing nitro mustard or storing the finished nitro mustard product, unknown impurities will be formed, and the structure and content of the unknown impurities are uncertain, and there is no method ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/155C07C229/36C07C227/20G01N30/06
CPCC07D295/155C07C229/36C07C227/20C07C231/12G01N30/06Y02P20/55
Inventor 石少龙吴自成赵鹏桂星星王新锋雷飞
Owner BEIJING ZHENDONG GUANGMING PHARMA RES INST
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