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Intermediate compound for preparing relugolix, preparation method of intermediate compound and preparation method of relugolix

A compound and intermediate technology, applied in the field of drug synthesis, can solve the problems of cumbersome operation, many impurities, and low yield, and achieve the effect of reducing the content of impurities

Inactive Publication Date: 2021-07-20
北京海美源医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many problems in the process of synthesizing Relugoli in the prior art, such as cumbersome operation, many impurities and low yield etc.

Method used

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  • Intermediate compound for preparing relugolix, preparation method of intermediate compound and preparation method of relugolix
  • Intermediate compound for preparing relugolix, preparation method of intermediate compound and preparation method of relugolix
  • Intermediate compound for preparing relugolix, preparation method of intermediate compound and preparation method of relugolix

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preparation example Construction

[0061] The embodiment of the present invention also provides a preparation method of relugoli, which is synthesized by referring to the following synthetic route:

[0062]

[0063] The operations of Step 1, Step 2 and Step 3 in the synthetic route are consistent with the operations of Step 1, Step 2 and Step 3 described above. The operation of step 4 includes: mixing dimethylamine with the compound shown in formula (3) for reaction; specifically, at 0-10° C., mixing the tetrahydrofuran solution of dimethylamine and the reaction system at 0-10° C. The reaction is carried out under the condition of ℃, and the reaction system is the system after the reaction of the compound represented by formula (2) to form the compound represented by formula (3), that is, the reaction system after step 3 is performed. After the tetrahydrofuran solution of dimethylamine is reacted with the reaction system, the reaction solution is post-treated to obtain relugoli.

Embodiment 1

[0066] The present invention provides an intermediate compound for preparing relugoli, whose structural formula is:

[0067] (marked as S23-LX3-7).

[0068] This embodiment provides the preparation method of this intermediate compound, comprising:

[0069] Synthesize according to the following synthesis path:

[0070] specifically,

[0071] To the there-necked flask, add 7.2g of Pd / C and mix in 100ml of purified water, add 3000ml of methanol, S23-LX3-6120g, stir, suspend the solid in the solvent, add 22g of concentrated hydrochloric acid, stir evenly, seal and vacuum, replace with hydrogen for 2 For the second time, keep the hydrogen pressure at 4 atmospheres and react at 25°C.

[0072] Reaction monitoring: LC-MS monitoring until the end of the reaction.

[0073] Post-processing: Add 500ml of purified water to the reaction system and stir for 10 minutes, add 3500ml of acetonitrile, 150ml of triethylamine to adjust Ph=8, heat to reflux and dissolve completely, filter wi...

Embodiment 2

[0076] The present invention provides an intermediate compound for preparing relugoli, whose structural formula is:

[0077] Recorded as S23-LX3-8.

[0078] This embodiment provides the preparation method of this intermediate compound, comprising:

[0079] Synthesize according to the following synthesis path:

[0080] specifically,

[0081] Feeding reaction: Add 5.14g of CDI, 160ml of acetonitrile, 8.0g of TEA to the three-necked flask, stir to dissolve and clarify at 10-20°C, add 2.8g of methoxylamine hydrochloride and stir to clarify, add the S23- prepared in Example 1 LX-7, 8.0g, heated up to reflux reaction (80°C), and stirred for 3.5h.

[0082] Reaction monitoring: TLC monitoring (developer: ethyl acetate: n-hexane = 1:1, color development: ultraviolet 254nm), after the reaction is completed, the temperature is cooled in a water bath. see image 3 .

[0083] Post-processing: Add the reaction system to 480ml of purified water at a temperature of 18°C, stir to pre...

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Abstract

The invention relates to the technical field of medicine synthesis, in particular to an intermediate compound for preparing relugolix, a preparation method of the intermediate compound and a preparation method of relugolix. The intermediate compound for preparing the relugolix is any one of compounds shown in the following structural formula, wherein R is a leaving group. The embodiment of the invention provides a novel intermediate for preparing the relugolix, and provides a novel method for synthesizing the relugolix, so that the yield can be increased, and the impurity content can be reduced.

Description

technical field [0001] The present invention relates to the technical field of drug synthesis, in particular, to an intermediate compound used for the preparation of relugoli, a preparation method thereof, and a preparation method of relugoli. Background technique [0002] Relugolix is ​​a non-peptide gonadotropin-releasing hormone (GnRH) antagonist that blocks the action of GnRH through potent and selective antagonism of GnRH receptors in the human anterior pituitary. Relugoli can inhibit the secretion of gonad-stimulating hormone (luteinizing hormone LH and follicle-stimulating hormone FSH) in the pituitary gland, thereby inhibiting the secretion of sex hormones such as E2 (estradiol) and progesterone in the ovary, and then can It is used to treat symptoms associated with prostate cancer and uterine fibroids. There are many problems in the process of synthesizing relugoli in the prior art, such as cumbersome operation, many impurities and low yield. [0003] In view of t...

Claims

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Application Information

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IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 张旭李伟吴涛
Owner 北京海美源医药科技有限公司
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