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Cyclopropyl pregnene compound and application thereof

A compound, the technology of cyclopropyl formate, which is applied in the field of cyclopropyl-pregnant steroid glucocorticoids, can solve the problem of reducing adverse reactions and other problems

Inactive Publication Date: 2011-06-01
TIANJIN JINYAO GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In fact, ciclesonide with isobutyrate at position 21 is more than 100-fold less active in vitro than deisobutyryl ciclesonide at position 21 without isobutyrate at position 21, which means that it It can only be activated after being inhaled into the lungs, and the adverse reactions will be significantly reduced

Method used

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  • Cyclopropyl pregnene compound and application thereof
  • Cyclopropyl pregnene compound and application thereof
  • Cyclopropyl pregnene compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121] Example 1: 9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-pregna-1,4-diene-3,20-diketone-17-cyclopropylcarboxylate-21- Preparation of acetate

[0122]

[0123] Dissolve 10mmol of 9α-fluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-diketone-21-acetate in 50ml of pyridine, and cool the resulting solution to 0 ~5°C, add 0.2g of 4,4-dimethylaminopyridine, then slowly add 12mmol of cyclopropylformyl chloride at a temperature of 5-10°C, and then stir the obtained product at a temperature of 5-10°C The mixture was reacted for 4 hours with 2N hydrochloric acid added dropwise to adjust the pH value to 2-3, diluted in ice water, and the aqueous phase was extracted three times with dichloromethane, the dichloromethane was combined, and the pH was adjusted to 5-3 with sodium bicarbonate solution. 6 and washed with water, the organic phase was concentrated, and recrystallized from methanol to obtain 4.2 mmol of the target compound.

[0124] Elemental analysis measured value: C28H...

Embodiment 2

[0127] Example 2: Preparation of 9α-fluoro-11β, 17α, 21-trihydroxy-16β-methyl-pregna-1,4-diene-3,20-diketone-17-cyclopropyl carboxylate

[0128]

[0129]The pH in Example 1 is 5-6 and the methylene chloride phase washed with water is added dropwise to the organic phase with 2% NaOH / methanol solution at 0-5 degrees under nitrogen, and after reacting for 3 hours, use acetic acid to adjust the pH 6-7, 3.2 mmol of the target compound was obtained by column chromatography.

[0130] Elemental analysis measured value: C26H33FO6 C, 67.78; H, 7.21; F, 4.14; O, 20.87

Embodiment 3

[0131] Example 3: Preparation of Pregna-1,4-diene-3,20-diketone-11,17,21-trihydroxy-17-cyclopropylcarboxylate-21-acetate

[0132]

[0133] Using pregna-1,4-diene-3,20-diketone-11,17,21-trihydroxy-21-acetate as raw material, 5.2 mmol of the target compound was synthesized according to the process of Example 1.

[0134] Elemental analysis measured value: C27H34O7 C, 68.92; H, 7.28; O, 23.80

[0135] 13 C-NMR: 13.2(CH), 8.4(CH2), 8.4(CH2), 101.9(C), 41.2(C), 50.3(CH), 22.9(CH2), 24.1(CH), 186.0(C), 68.9 (CH), 31.5(CH), 40.3(CH2), 168.2(C), 124.5(CH), 128.7(CH), 158.8(CH), 44.3(C), 59.2(CH), 32.3(CH2), 32.9 (CH2), 171.5(C), 170.4(C), 212.1(C), 68.0(CH2), 17.0(CH3), 19.1(CH3), 20.6(CH3).

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Abstract

The invention discloses a cyclopropyl pregnene compound and application thereof, and discloses a novel adrenocortical hormone compound shown in a formula (I), a medicine composition containing the compound shown in the formula (I) as an active component and one or more pharmaceutic adjuvants, and application of the compound shown in the formula (I) or physiologically acceptable salt or solvate thereof as a medicine for treating of the diseases of mammal especially human, especially local inflammation.

Description

field of invention [0001] The invention relates to a cyclopropyl ester pregnant compound glucocorticoid and its application. The present invention also relates to the pharmaceutical preparation containing the compound and the preparation of the compound, especially for the treatment of inflammatory diseases, allergic diseases and allergic diseases. Background technique: [0002] The anti-inflammatory properties of glucocorticoids are well known and are widely used in the treatment of inflammatory disorders or inflammatory diseases such as asthma, rhinitis, eczema, etc., to relieve symptoms. In the treatment of these diseases, long-term Medication, so it will also cause various adverse reactions throughout the body, common adverse reactions such as osteoporosis and vertebral compression fractures, substance metabolism and water and salt metabolism disorders, cataracts and glaucoma. In order to reduce the adverse reactions of glucocorticoids, scientists are constantly looking...

Claims

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Application Information

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IPC IPC(8): C07J7/00A61K31/57A61P29/00A61P37/08A61P37/02
Inventor 孙亮陈松赵琳
Owner TIANJIN JINYAO GRP
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