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2-Arylbenzo[b] thiophenes useful for the treatment of estrogen deprivtion syndrome

A technology of estrogen deficiency and compounds, applied in the direction of active ingredients of heterocyclic compounds, drug combinations, organic chemistry, etc., can solve problems such as poor patient compliance

Inactive Publication Date: 2001-01-03
ELI LILLY & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although estrogen replacement therapy is often used for estrogen deficiency syndromes, patient compliance with this therapy is poor because many women cannot tolerate certain side effects and the inconvenience of the drug form of treatment

Method used

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  • 2-Arylbenzo[b] thiophenes useful for the treatment of estrogen deprivtion syndrome

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0091] Preparation 12-(3-methoxyphenylthio)-4'-methoxyacetophenone

[0092] 3-Methoxythiophenol (50.0 g, 0.356 mol) was dissolved in 700 ml of ethanol. To this mixture was added potassium hydroxide tablets (20 g, 0.36 mol). 82.5 g (0.36 mol) of 2-bromo-4'-methoxyacetophenone was added in small portions keeping the temperature at about 25°C. The reaction was carried out at room temperature for 3 hours. The reaction was quenched by evaporation of the alcohol to give a brown oil. The oil was partitioned between 2L of water and 1.5L of ether. The ether layer was separated and washed with water, dried over anhydrous magnesium sulfate and evaporated to give a solid. The solid was crystallized from a mixture of ether-petroleum ether (3:1) to give the title compound as a pink crystalline solid. mp53-54℃; EA calculated value C 16 h 16 o 3 S: C 66.64; H, 5.59; O, 16.64; S, 11.12.

[0093] Found: C 66.55; H, 5.87; O, 16.82; S, 10.86.

preparation example 2

[0095] 2-Phenylthioacetophenone

[0096] According to the method of Preparation 1, the title compound was prepared from thiophenol and 2-bromoacetophenone. mp 52-53℃; EA calculated value C 14 h 12 OS: C 73.65; H, 5.30; O, 7.01; S, 14.04.

[0097] Found: C 73.46; H, 5.50; O, 7.25; S, 14.30.

preparation example 3

[0099] 2-Phenylthio-4'-methoxyacetophenone

[0100] According to the method of Preparation 1, the title compound was prepared from thiophenol and 2-bromo-4'-methoxyacetophenone. mp 83-85℃; EA calculated value C 15 h 14 o 2 S: C 69.74; H, 5.46. Found: C 69.52; H, 5.48.

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Abstract

This invention provides methods which are useful for the inhibition of the various medical conditions associated with estrogen deprivation syndrome including osteoporosis and hyperlipidemia utilizing compounds of formula I.

Description

field of invention [0001] The present invention relates to the fields of medicine and organic chemistry, and provides 2-arylbenzo[b]thiophene compounds for effectively inhibiting various estrogen deficiency diseases. Background of the invention [0002] "Estrogen deficiency syndrome" is a term used to describe a variety of pathological conditions that often afflict women with insufficient estrogen levels. One of the most common causes of estrogen deficiency in women is the natural cessation of menstruation with age, ie menopause. In addition, unnatural conditions, including oophorectomy, cessation of hormone production due to chemotherapy, or the effects of drugs, may also induce estrogen deficiency. Although many pathologies are considered eligible for this term, two major effects of estrogen deficiency syndrome are the greatest contributors to long-term clinical care, namely osteoporosis and cardiovascular effects, specifically hyperlipidemia. [0003] Osteoporosis refer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/54A61K31/38A61K31/381A61K31/445A61P3/06A61P5/30A61P15/12A61P19/10C07D333/56
CPCA61K31/381A61K31/445A61K31/38A61P15/12A61P19/10A61P3/06A61P5/30A61K2300/00C07D333/54
Inventor G·J·库利南
Owner ELI LILLY & CO