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Compounds useful in the manufacture of an anti-inflammatory androstane derivative

A compound and product technology, applied in the field of treatment of inflammatory diseases and allergic diseases, can solve the problems of difficult understanding of pharmacodynamics and pharmacokinetics

Inactive Publication Date: 2005-10-12
GLAXO GRP LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Certain glucocorticoid compounds also have complex metabolic pathways in which active metabolites are produced that can complicate the pharmacodynamics and pharmacokinetics of such compounds

Method used

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  • Compounds useful in the manufacture of an anti-inflammatory androstane derivative
  • Compounds useful in the manufacture of an anti-inflammatory androstane derivative
  • Compounds useful in the manufacture of an anti-inflammatory androstane derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0238] Example 1: 6α,9α-difluoro-17α-[(2-furylcarbonyl)oxy]-11β-hydroxy-16α-methyl- 3-Oxo-androst-1,4-diene-17β-thiocarboxylate S-fluoromethyl ester unsolvated form 1

[0239] A suspension of Intermediate 1 (2.5 g, 4.94 mmol) was dissolved in dry N,N-dimethylformamide (25 ml) and sodium bicarbonate (465 mg, 5.53 mmol) was added. The mixture was stirred at -20°C and bromofluoromethane (0.77ml, 6.37mmol) was added and the mixture was stirred at -20°C for 2 hours. Diethylamine (2.57ml, 24.7mmol) was added and the mixture was stirred at -20°C for 30 minutes. The mixture was added to 2M hydrochloric acid (93ml) and stirred for 30 minutes. Water (300ml) was added and the precipitate was collected by filtration, washed with water and dried in vacuo at 50°C to give a white solid which was recrystallized from acetone / water (to give 6α,9α-difluoro-17α-[( 2-furylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxo-androst-1,4-diene-17β-thiocarboxylate S-fluoromethyl ester) and at 50 Drying ...

Embodiment 2

[0268] Example 2: 6α,9α-difluoro-17α-[(2-furylcarbonyl)oxy]-11β-hydroxy-16α-methyl- 3-Oxo-androst-1,4-diene-17β-thiocarboxylate S-fluoromethyl ester

[0269] Unsolvated form 2

[0270] 6α,9α-Difluoro-17α-[(2-furylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxo-androst-1,4-diene-17β-thio A suspension of S-fluoromethyl carboxylate (prepared eg according to the first method of Example 1) (6.0 g) in dichloromethane (180 ml) was heated to reflux to give a bright solution. The solution was clarified by hot filtration (Whatman 54 filter paper) and the solution was distilled at atmospheric pressure (ca. 100 ml of solvent collected), giving crystallization at reflux. The mixture was kept at reflux for about 30 minutes and cooled slowly to ambient temperature. The mixture was further cooled and aged at 10-20°C for 2 hours. The slurry was cooled below 10°C and the product was filtered off, absorbed dry and dried under vacuum at about 60°C overnight to give a white solid (4.34 g, 71%)...

Embodiment 3

[0273] Example 3: 6α,9α-difluoro-17α-[(2-furylcarbonyl)oxy]-11β-hydroxy-16α-methyl- 3-Oxo-androst-1,4-diene-17β-thiocarboxylate S-fluoromethyl ester

[0274] Unsolvated form 3

[0275] 6α,9α-Difluoro-17α-[(2-furylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxo-androst-1,4-diene-17β-thio A suspension of carboxylic acid S-fluoromethyl ester acetone solvate (prepared as in Example 11) (20.0 g) in dichloromethane (800 ml, 40 vol) and water (10 ml, 0.5 vol) was heated to reflux, A bright solution was obtained. The solution was clarified by hot filtration (Whatman 54 filter paper), during which time some solid crystallized in the filtrate, which was fully dissolved by heating to reflux. The solution was distilled at atmospheric pressure (about 400 ml of solvent collected) and allowed to cool to ambient temperature. The mixture was further cooled and aged at <10°C for 10 minutes. The product was filtered, absorbed dry and dried under vacuum at about 60°C overnight to give a whit...

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Abstract

According to one aspect of the invention, there is provided a preparation method of an intermediate compound of formula (II) of the compound of the formula (I). There are also provided novel intermediate compositions.

Description

[0001] This application is an invention with the filing date of August 3, 2001 and the name is "6α, 9α-difluoro-17α-[(2-furyl carboxyl)oxy]-11β-hydroxyl-16α- as an anti-inflammatory agent Methyl-3-oxo-androst-1,4-diene-17-thiocarboxylate S-fluoromethyl ester" Chinese patent application (national application number is No.01816662.8, international application number is PCT / GB01 / 03495) divisional application. technical field [0002] The invention relates to a novel anti-inflammatory and anti-allergic androstane series compound and a preparation method thereof. The invention also relates to pharmaceutical formulations containing said compounds and their use in therapy, especially in the treatment of inflammatory and allergic diseases. Background technique [0003] Glucocorticoids having anti-inflammatory properties are well known and widely used in the treatment of inflammatory diseases or conditions such as asthma and rhinitis. For example, US Patent 4335121 discloses 6α,9α...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/12A61K9/14A61K31/56A61K31/58A61K45/00A61K47/06A61K47/18A61K47/36A61P5/44A61P11/06A61P11/08A61P29/00A61P37/08A61P43/00C07J17/00C07J31/00C07J33/00C07J43/00
CPCC07J31/006A61P1/04A61P1/08A61P11/00A61P11/02A61P11/06A61P11/08A61P17/00A61P17/02A61P17/04A61P17/06A61P19/02A61P27/02A61P27/14A61P29/00A61P37/08A61P43/00A61P5/00A61P5/44C07J31/00
Inventor K·比加迪克S·J·库特R·K·尼斯
Owner GLAXO GRP LTD
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