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Synthesis method of pomalidomide

A technology of pomalidomide and its synthetic method, which is applied in the field of medicinal chemistry, can solve the problems of high cost of reaction reagents, harsh conditions, and large pollution, and achieve the effects of reducing production costs and environmental pollution, mild reaction conditions, and high yields

Pending Publication Date: 2018-07-13
仁合熙德隆药业有限公司 +2
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AI Technical Summary

Benefits of technology

This new method involves preparing gemimides from 2-chloro-3-(phenyl)phtha-19lene (CAS), instead of starting up expensive chemical processes that require highly specialized equipment or involve dangerous gases like chlorine gas. Instead, this new method makes certain technical benefits over existing methods due to its lower price, safety concerns associated with handling hazardous substances, ease of operation compared to previous techniques, and higher yields achieved at reduced pressures. Additionally, there're no wasted liquid products produced when reactants were replaced without adding extra steps.

Problems solved by technology

This patents discuss different ways to make certain types of drugs called pomalsidone mesothelin antibody(PML). These molecules were found naturally occurring during childhood leukemia disease when studying their effects on bacterial growth and inflammations caused by chemotherapy treatments like cytotoxins. People have long ago discovered these compounds through chemical reactions involving various starting substances. They tested them against cancer cells and other diseases related to autoimmunity and lymphatic dysfunction.

Method used

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  • Synthesis method of pomalidomide
  • Synthesis method of pomalidomide
  • Synthesis method of pomalidomide

Examples

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Embodiment 1

[0027] Add 60 g of 3-bromophthalic acid and 60 mL of acetic anhydride into a 500 mL three-neck flask, stir at 80°C for 3 h, spot the plate to confirm that the reaction is complete, cool to room temperature, filter, and wash with 2×30 mL of petroleum ether. Dry 3-bromophthalic anhydride, yield 89%.

[0028] Add 43.4 g of 3-bromophthalic anhydride into a 1 L single-necked bottle, add 300 mL of acetic acid and stir, then add 36.7 g of 3-amino-2,6-piperidinedione hydrochloride and 19.8 g of sodium acetate in sequence Reflux for 3 h, cool to room temperature, filter, wash with 2×50 mL of water and 30 mL of ethanol, filter and dry to obtain compound 4 with a yield of 94.1%.

[0029] 64.1 g of compound 4, 500 mL of acetonitrile, 18 mL of ammonia water, 40 g of potassium carbonate and 0.5 g of cuprous oxide were reacted in a 1 L closed system at 50°C for 6 hours. After the reaction was completed, the solid was removed by filtration and evaporated to dryness to obtain the crude produc...

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Abstract

The invention discloses an improved synthesis method of pomalidomide, and belongs to the field of medicinal chemistry. 3-halogenated phthalic acid 1 used as a raw material (F, Cl and Br) is condensedthrough an acetic anhydride system to obtain a phthalic anhydride compound 2; the compound 2 reacts with 3-amino-2,6-piperidone diketone salt to obtain a phthalimide derivative 4; and the compound 4 and ammonia water undergo amino displacement to obtain the pomalidomide. According to the synthesis method, the 3-halogenated phthalic acid is used as a start raw material, which replaces the current reported 3-nitrophthalic acid; amino directly replaces halogen to prepare the pomalidomide, so that high-pressure hydrogenation during nitroreduction is avoided, or use of a metal reducer such as ironpowder is avoided; a reaction process is simple, easy to operate, low in pollution and high in yield; and a solvent can be recycled and reused, thereby facilitating large-scale industrial production.

Description

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Claims

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Application Information

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Owner 仁合熙德隆药业有限公司
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