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Industrial process for the synthesis of ulipristal acetate and its 4'-acetyl analogue

A technology of acetyl group and compound, applied in the industrialized field for synthesizing ulipristal acetate and its 4'-acetyl analog, can solve problems such as incompatibility

Active Publication Date: 2016-05-18
RICHTER GEDEON NYRT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to our experiments, several by-products are formed in this reaction at this relatively high temperature, therefore, this method is not suitable for the alkylation of cyanohydrins protected as silyl ethers

Method used

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  • Industrial process for the synthesis of ulipristal acetate and its 4'-acetyl analogue
  • Industrial process for the synthesis of ulipristal acetate and its 4'-acetyl analogue
  • Industrial process for the synthesis of ulipristal acetate and its 4'-acetyl analogue

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of 11β-[4-(N,N-dimethylamino)-phenyl]-17-hydroxy-19-norpregna-4,9-diene-3,20-dione

[0048] 8.0g (14.5mM) 11β-[4-(N,N-dimethylamino)-phenyl]-3,3-ethanedioxy-5α-hydroxyl-17α-[(trimethylsilyl) Oxy]-5α-estr-9-ene-17β-carbonitrile was dissolved in 130 ml of tetrahydrofuran, and the solution was cooled to -50°C. First 60 ml (180 mM) of methyl lithium 3.0 M solution in diethoxymethane were added dropwise followed by 27 ml (180 mM) of tetramethylethylenediamine at such a rate that the reaction temperature was maintained below -45°C. The reaction mixture was stirred at a temperature of -45 to (-40)°C for 3 hours, then 70 ml of water was added dropwise very carefully to the reaction mixture while the temperature was raised to +20°C. After stirring for 5 minutes, the phases were separated and the organic phase was washed with 20 ml of water and concentrated under reduced pressure. To the residue were added 80 ml of methanol and 110 ml of 1N sulfuric acid solution, and...

Embodiment 2

[0053] Synthesis of 11β-[4-(N,N-dimethylamino)-phenyl]-17-hydroxy-19-norpregna-4,9-diene-3,20-dione

[0054] 25.0 g (40.1 mM) of 11β-[4-(N,N-dimethylamino)-phenyl]-3,3-ethanedioxy-5,17α-bis[(trimethylsilyl)oxy Base]-5α-estr-9-ene-17β-carbonitrile was dissolved in 500 ml of dimethoxymethane, and the solution was cooled to -50°C. First 66.7 ml (200 mM) of a 3.0 M solution of methyllithium in diethoxymethane was added dropwise, followed by 30 ml (200 mM) of tetramethylethylenediamine, at such a rate that the reaction temperature was maintained below -40°C. The reaction mixture was stirred at a temperature of -45 to (-35)°C for 3 hours, then 210 ml of water were added dropwise to the reaction mixture very carefully while the temperature was raised to +20°C. After stirring for 5 minutes, the phases were separated and the organic phase was washed with 50 ml of water and concentrated under reduced pressure. To the residue were added 220 ml of methanol and 300 ml of 1N sulfuric acid...

Embodiment 3

[0059] 3,3-Ethylenedioxy-11β-[4-(2-methyl-1,3-dioxolan-2-yl)-phenyl]-5,17α-bis[(trimethylsilyl Synthesis of yl)oxy]-5α-estr-9-ene-17β-carbonitrile

[0060] 25.0 g (41.68 mM) of 3,3-ethanedioxy-11β-[4-(2-methyl-1,3-dioxolan-2-yl)-phenyl]-5-hydroxyl-17α -[(trimethylsilyl)oxy]-5α-estr-9-ene-17β-carbonitrile (Example 25 of WO2001 / 74840) was dissolved in 125ml of dichloromethane, and dropped into the solution at 20°C Add 5 g of imidazole, and then dropwise add 8.4 ml of chlorotrimethylsilane. The reaction mixture was stirred at 20-25°C for 1 hour, then diluted with 70ml of dichloromethane and 70ml of water. After vigorous stirring for 10 minutes, the phases were separated. The organic phase was washed with 2 x 50 ml of water, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol to afford 22.2 g (80.0%) of the title compound.

[0061] Melting point: 134-135°C

[0062] 1 HNMR (800MHz, CDCl 3 )δ:7.34(m,2H),7.16(m,2H),4.33(m,1H),3.9...

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Abstract

The present invention relates to a new process for the synthesis of compounds of a formula (I) (wherein the meaning of the R is dimethylamino or acetyl group) using the compound of a formula (II) (wherein the meaning of R is dimethylamino or 2-methyl-1,3-dioxolan-2-yl group) as starting material, as well as to the intermediate of the process.

Description

technical field [0001] The steroidal compounds obtained according to the process of the invention are progesterone derivatives. Background technique [0002] In addition to its effects on many reproductive system tissues, progesterone plays an important role in preparing the body for conception and maintaining pregnancy. Selective progesterone receptor modulators can have agonistic and antagonistic effects by binding to progesterone receptors. They have different uses in gynecology. Antiprogestins (ie any substance that blocks the action of progesterone) can play a role in the pharmacological regulation of pregnancy and in the treatment of different diseases or pathological conditions such as breast cancer and endometriosis. Antiprogestins are primarily used for contraception and emergency contraception, and they can also be used to treat other gynecological conditions (eg uterine fibroids). [0003] The present invention relates to a new method for the synthesis of proge...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00C07J41/00C07J51/00
CPCA61P5/30C07J7/0045C07J41/0083C07J51/00C07J21/00C07J75/00C07B2200/07C07J21/006
Inventor S·马霍C·尚陶J·彻尔盖伊J·霍瓦特A·奥劳尼Z·贝尼
Owner RICHTER GEDEON NYRT
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