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Preparing method of bazedoxifene derivative

A technology for bazedoxifene and derivatives, which is applied in the field of compound preparation and achieves the effects of simple operation method, important application value and high purity

Active Publication Date: 2017-08-11
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The synthetic method of the bazedoxifene derivative provided by the present invention has not been reported yet, and relevant pharmacology and pharmacokinetic studies are carried out on the bazedoxifene derivative, and the bazedoxifene derivative may have better medicinal properties. prospect

Method used

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  • Preparing method of bazedoxifene derivative
  • Preparing method of bazedoxifene derivative
  • Preparing method of bazedoxifene derivative

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Embodiment 1

[0060] Such as figure 1 Shown: the preparation method of bazedoxifene derivative, specifically comprises the following steps:

[0061] Preparation of Compound II:

[0062] Dissolve p-methoxyaniline I (46.50g, 0.0.38mol) in aniline (25mL), add 2-bromo-4'-methoxyacetophenone (61.78g, 0.27mol) in xylene (93mL) solution, reacted at 140°C for 9 hours, and the light reddish brown solution turned into a deep reddish brown solution. Under ice-cooling, 2N HCl aqueous solution (400 mL) was added, extracted with ethyl acetate (200 mLx2), the organic phase was dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 51.65 g of light reddish-brown liquid Compound II with a yield of 75.34%.

[0063]

[0064] Preparation of Compound III: Dissolve Compound II (49.21g, 0.19mol) in N,N-dimethylformamide (900mL), add phosphorus oxychloride (44.68g, 0.29mol) dropwise, and react at 65°C for 7 hours , the light reddish brown solution turned into dark yellow clear solution. Un...

Embodiment 2

[0075] Preliminary experiments were carried out on Compound VII--Bazedoxifene derivatives prepared in Example 1 of the present invention. The experimental results showed that Compound VII synthesized by the present invention can competitively inhibit the binding of 17β-estradiol to ERα and ERβ. It is expected to be developed as a drug for treating postmenopausal women with moderate to severe hot flashes and preventing osteoporosis, or for studying the pharmacokinetics and metabolic pathways of bazedoxifene-related drugs.

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Abstract

The invention discloses a synthesis method of a bazedoxifene derivative. According to the preparing method of the bazedoxifene derivative, p-anisidine is adopted as a raw material, and through a six-step reaction, the synthesis of the bazedoxifene derivative is achieved. The preparing method of the bazedoxifene derivative is reasonable in technological design and high in operability, the reaction condition is mild, the yield is high, and thus industrialized production can be achieved. The prepared bazedoxifene derivativ bazedoxifene provides an important basis for scientific evaluation of quality, safety and efficiency of bazedoxifene; meanwhile, the bazedoxifene derivative is good in pharmacological activity, can be developed into medicines used for treating osteoporosis, and thus the bazedoxifene derivative has important application value.

Description

technical field [0001] The invention relates to a preparation method of a compound, and specifically designs a preparation method of bazedoxifene derivatives. [0002] technical background [0003] Bazedoxifene acetate, the chemical name is 1-{4-[2-(cyclohexylimino-1-)ethoxy]benzyl}-2-(4-hydroxyphenyl)-3 -Methyl-1H-indole-5-phenol acetate, which was jointly developed by Ligand Pharmaceuticals and Wyeth (Wyeth) Pharmaceuticals of the United States and transferred to Pfizer Pharmaceuticals. On April 17, 2009, the European Medicines Agency approved its use in Italy It was listed in Spain and Spain under the product name Conbriza, and it was launched in Japan in July 2010 under the product name Viviant. In 2013, it was launched in the United States with FDA approval under the product name Duavee. [0004] Bazedoxifene belongs to the third-generation selective estrogen receptor modulator (SERM), which can competitively inhibit the binding of 17β-estradiol to ERα and ERβ, and trea...

Claims

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Application Information

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IPC IPC(8): C07D209/12
CPCC07D209/12
Inventor 吴文超曹锋张池崔希林
Owner TLC NANJING PHARMA RANDD CO LTD
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