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Benzoxazepine derivatives as selective estrogen receptor modulators

A technology of selecting compounds, applied in sexual diseases, drug combinations, organic active ingredients, etc., can solve problems such as exacerbation and inability to improve cognitive function in elderly patients

Inactive Publication Date: 2007-09-19
JANSSEN PHARMA NV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] However, there are reports that raloxifene exacerbates symptoms associated with menopause, such as hot flashes and vaginal dryness, and does not improve cognitive function in older patients
Although women using ERT reported higher rates of vaginal bleeding and breast discomfort than those using raloxifene or placebo, patients taking raloxifene were significantly more likely than those taking placebo or ERT. Patients had a higher incidence of hot flashes and more frequent leg cramps than patients receiving a placebo

Method used

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  • Benzoxazepine derivatives as selective estrogen receptor modulators
  • Benzoxazepine derivatives as selective estrogen receptor modulators
  • Benzoxazepine derivatives as selective estrogen receptor modulators

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] 7-Methoxy-3-(4-methoxy-phenyl)-chromen-4-one

[0067]

[0068] 7-Hydroxy-4'-methoxyisoflavone (25.2 g, 93.9 mmol) was dissolved in a mixture of dry DMF (125 ml) and acetone (125 ml). Anhydrous potassium carbonate (13.0 g, 93.9 mmol) and dimethyl sulfate (8.90 ml, 93.9 mmol) were added successively, and the mixture was heated to 70° C. for 4 hours. After cooling, the reaction mixture was poured on water (1 L). The resulting yellow precipitate was collected by filtration and dried in vacuo to afford the title compound (25.5 g, 96%).

[0069] MS(m / Z)=283(MH+)

Embodiment 2

[0071] 7-Methoxy-3-(4-methoxy-phenyl)-chroman-4-one

[0072]

[0073] 7-Methoxy-3-(4-methoxy-phenyl)-chromen-4-one (13.0 g, 46.0 mmol) was dissolved in anhydrous THF (400 ml) and cooled to -78°C. DIBAL-H (1.5M, 79ml, 0.18mol) was added dropwise over 20 minutes and the reaction was stirred at -78°C for 1 hour. The reaction mixture was quenched with Rochelle's solution (150ml) and stirred at 22°C for 24 hours. The reaction mixture was CH 2 Cl 2 (200ml×2) extraction. Organic layer with H 2 O (500ml x 3) washed, dried over Na2SO4, concentrated in vacuo to afford the title compound (yellow semi-solid) in quantitative yield.

[0074] MS(m / Z)=285(MH+)

Embodiment 3

[0076] 7-Methoxy-3-(4-methoxy-phenyl)-chroman-4-one oxime

[0077]

[0078] A mixture of 7-methoxy-3-(4-methoxy-phenyl)-chroman-4-one (13.14g, 46.22mmol) and hydroxylamine hydrochloride (12.85g, 184mmol) was dissolved In a 1:1 mixture of pyridine and ethanol (20ml), it was heated to reflux under argon atmosphere for 1 hour. The mixture was poured on water (100ml) and the precipitate was collected by vacuum filtration to give the oxime (11.9g, 86%, white solid).

[0079] MS(m / Z)=300(MH+)

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PUM

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Abstract

The present invention is directed to novel benzoxazepine derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and diseases mediated by an estrogen receptor.

Description

field of invention [0001] The present invention relates to novel benzoxazepine derivatives, pharmaceutical compositions containing them and their use in the treatment or prevention of estrogen receptor mediated disorders and diseases including, for example, hot flashes, Vaginal dryness, osteopenia, osteoporosis, hyperlipidemia, cognitive decline, degenerative brain disease, cardiovascular disease, cerebrovascular disease, hormone-sensitive cancers and hyperplasia (including breast, intrauterine membrane and cervical tissue and prostate tissue in men), endometriosis, uterine fibroids, osteoarthritis; alone or in combination with progestins or progesterone antagonists as contraceptives. The compounds of the present invention are selective estrogen receptor modulators. Background of the invention [0002] Estrogen is a female hormone that is essential for the reproductive process and for the development of the uterus, breasts and other bodily changes assoc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D267/14A61P35/00A61K31/553
CPCC07D267/10C07D267/14A61P3/06A61P5/30A61P9/00A61P13/02A61P13/08A61P15/00A61P15/02A61P15/08A61P15/12A61P19/02A61P19/08A61P19/10A61P25/00A61P25/28A61P35/00A61P43/00
Inventor J·C·兰特Z·隋J·J·费奥尔德利索
Owner JANSSEN PHARMA NV
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