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6.alpha., 9.alpha.-difluoro-17.alpha.-'(2-furanylcaboxyl)oxy!-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androst-1,4,-diene-17-carbothioic acid s-fluoromethyl ester as an anti-inflamatory agent

A technology of substituents and heteroaryls, applied in the field of androstane series compounds, 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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  • 6.alpha., 9.alpha.-difluoro-17.alpha.-'(2-furanylcaboxyl)oxy!-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androst-1,4,-diene-17-carbothioic acid s-fluoromethyl ester as an anti-inflamatory agent
  • 6.alpha., 9.alpha.-difluoro-17.alpha.-'(2-furanylcaboxyl)oxy!-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androst-1,4,-diene-17-carbothioic acid s-fluoromethyl ester as an anti-inflamatory agent
  • 6.alpha., 9.alpha.-difluoro-17.alpha.-'(2-furanylcaboxyl)oxy!-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androst-1,4,-diene-17-carbothioic acid s-fluoromethyl ester as an anti-inflamatory agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0299] Example 1: 6α,9α-difluoro-17α-[(2-furylcarbonyl)oxy]-11β-hydroxy-16α-methyl- S-fluoromethyl 3-oxo-androst-1,4-diene-17β-thiocarboxylate

[0300] Will intermediate A suspension of 1 (2.5g, 4.94mmol) was dissolved in dry N,N-dimethylformamide (25ml) and sodium bicarbonate (465mg, 5.53mmol) 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 under vacuum at 50°C to give a white solid which was recrystallized in acetone / water and dried under vacuum at 50°C to give Title compound (2.351g, 88%):

[0301] LCMS retention time 3.66 min, m / z 539 MH + , NMRδ (CDCl 3 ) including 7.60 (1H, m), 7.18-7.11 (...

Embodiment 2

[0302] Example 2: 6α,9α-difluoro-17α-[(3-furylcarbonyl)oxy]-11β-hydroxy-16α-methyl- S-fluoromethyl 3-oxo-androst-1,4-diene-17β-thiocarboxylate

[0303] Use something like Example 1 The method described by Intermediate 2 to prepare Example 2 .

[0304] LCMS retention time 3.72 minutes, m / z 539 MH + .

Embodiment 3

[0305] Example 3: 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-[(2-thienylcarbonyl) Oxy]-androst-1,4-diene-17β-thiocarboxylate S-fluoromethyl ester

[0306] Use something like Example 1 The method described by Intermediate 3 to prepare Example 3 .

[0307] LCMS retention time 3.81 min, m / z 555 MH + .

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Abstract

There are provided according to the invention compounds of formula (I) wherein R1 represents C1-6 alkyl or C1-6 haloalkyl; R2 represents -C(=O)-aryl or -C(=O)-heteroaryl; R3 represents hydrogen, methyl (which may be in either the alpha or beta configuration) or methylene; R4 and R5 are the same or different and each represents hydrogen or halogen; and ---- represents a single or a double bond; and salts and solvates thereof. There are also provided processes for preparing compounds of formula (I) and use of the compounds in therapy especially in the treatment of inflammatory and allergic conditions.

Description

[0001] This application is that the international application date is August 3, 2001 (the international application number is PCT / GB01 / 03499), and the national phase application number is No.01816664.4. The invention title is "17β-thiocarboxylic acid as anti-inflammatory agent" Ester 17α-arylcarbonyloxyandrostane derivatives" is a divisional application of the application. technical field [0002] The present invention relates to a new anti-inflammation and anti-allergic androstane series compounds and their preparation method. 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] Glucocorticoid compounds having anti-inflammatory properties are well known and are widely used in the treatment of inflammatory diseases or conditions such as asthma and rhinitis. For example, US Patent 4335121 discloses 6α,9α-difluoro-17α-(1-oxo...

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P·琼斯J·J·佩尼
Owner GLAXO GRP LTD
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