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Estratriene derivatives

A technology of derivatives and compounds, applied in the field of estriene derivatives, can solve problems such as airway narrowing

Inactive Publication Date: 2006-11-22
CRYPTOPHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The consequence of this thickening is increased airway narrowing for a given amount of smooth muscle contraction

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0266] Synthesis of 2-methoxy-6-(4'-nitrobenzyloxy)iminoestradiol ("4NO")

Embodiment 1a

[0268] 2-Methoxyestradiol (1) was diacetylated by treatment with acetic anhydride in pyridine in 95% yield. Benzyl oxidation of this double protected species was performed with chromium trioxide in an acetic acid / water mixture in 45% yield. Both acetates were removed in 98% yield by treating the newly formed ketone compound (3) with potassium carbonate in aqueous methanol. Condensation of the ketone with O-(4-nitrobenzyloxy)hydroxylamine in methanol is then carried out to give 2-methoxy-6-(4-nitrobenzyloxy)iminoestradiol (5), Yield 99%.

[0269]

[0270] Route 9

Embodiment 1b

[0272] 3,17-bis-acetoxy-2-methoxyestra-1,3,5(10)triene (2)

[0273] 2-Methoxyestradiol (127.5 mg, 0.426 mmol) was dissolved in anhydrous pyridine (6.0 mL) under nitrogen atmosphere and cooled to 0°C. Acetic anhydride (3.0 mL) was added dropwise, and the reaction was allowed to warm to room temperature. After stirring overnight, the reaction mixture was cooled to 0 °C, at which point 50.0 mL of 1M aqueous hydrochloric acid was added and the reaction was allowed to warm to room temperature. Extraction was performed with ethyl acetate (3 x 50 mL), and the combined organic extracts were washed successively with 3M aqueous hydrochloric acid (50 mL), water (50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate, then filtered, and the solvent was concentrated in vacuo to give a white solid (154 mg). The product was homogeneous when analyzed by TLC, so purification was deemed unnecessary, but an analytical sample was purified on a silica gel column using 1:5 ethy...

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Abstract

Compounds and methods for modulating mesenchymal cell function, for instance smooth muscle and fibroblast proliferation or cytokine expression, and for treating conditions associated with mesenchymal cell function, for instance airway hyperresponsiveness associated with asthma. The compounds also supress inflammation. The compounds are a class of estratriene derivates, and includes various derivatives of 2-methoxyestradiol comprising a group A, including a substituted aromatic substituent in the 2-, 6- or 17- position.

Description

[0001] related application [0002] This application claims priority from US 60 / 470,397, which is incorporated herein by reference in its entirety. field of invention [0003] The present application relates to compounds and methods for modulating mesenchymal cell function, such as smooth muscle and fibroblast proliferation or cytokine expression, and for treating disorders associated with mesenchymal cell function, such as airway hyperresponsiveness associated with asthma. The compounds of the present application are a class of estratriene derivatives. Background of the invention [0004] Asthma is a disease characterized by varying degrees of airway obstruction, chronic inflammation, structural changes in the airway wall called airway wall remodeling (AWR), and airway hyperresponsiveness (AHR). AHR is usually measured by artificially inducing airway obstruction with methacholine or histamine or other irritant stimuli such as cold air or bradykinin. AHR is characterized b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00A61K31/565A61P11/06A61P29/00C07J43/00
CPCC07J41/00C07J43/00Y02P20/582A61P11/00A61P11/06A61P11/08A61P29/00A61P43/00
Inventor 阿拉斯泰尔·乔治·斯图尔特戴维·詹姆斯·麦卡利斯特约翰·尼古拉斯·兰伯特
Owner CRYPTOPHARMA
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