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Piperazinone compounds and application thereof

A technology of metabolites and prodrugs, applied in organic chemistry, drug combination, medical preparations containing active ingredients, etc.

Active Publication Date: 2016-07-27
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But clinically used tamoxifen and raloxifene can cause adverse reactions such as endometrial cancer and hot flashes (FisherB, CostantinoJP, WickerhamDL, et al.JNatiCancerInst, 1998, 90:1371-1388; WalshBW, KullerLH, WildRA , et al. JAmMedAssoc, 1998, 279:1445-1451)

Method used

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  • Piperazinone compounds and application thereof
  • Piperazinone compounds and application thereof
  • Piperazinone compounds and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Example 1: 1-ethyl-4-{4-[5-hydroxyl-2-(4-hydroxyphenyl)-3-methyl-1H-indol-1-yl]butyl}piperazine-2 , Preparation of 3-diketone

[0031] Step A): Preparation of 4-nitrobenzyloxybenzene

[0032] Put 4-nitrophenol (20.0g, 0.152mol) and anhydrous potassium carbonate (131.1g, 0.950mol) in a 1000mL flask, use acetone as solvent, add dropwise benzyl chloride (12.0g, 0.095mol), and reflux reaction After 24 hours, the solvent was evaporated under reduced pressure, the residue was stirred with water, filtered with suction, and dried to obtain 19.8 g of a light yellow solid with a yield of 90.8%. m.p.105-106°C. ESI-MS: m / z139 ([M+H] + ).

[0033] Step B): Preparation of 4-benzyloxyaniline

[0034] Put 4-nitrobenzyloxybenzene (10.0g, 0.044mol) and tin protochloride (50g, 0.220mol) in a 1000mL round bottom flask, ethanol as solvent, N 2 Under protection, react at 45°C for 24h. Evaporate the solvent under reduced pressure, transfer the residue to a 1000mL beaker with 600mL of s...

Embodiment 2

[0049] Embodiment 2: gelatin capsule

[0050]

Embodiment 3

[0051] Embodiment 3: tablet

[0052]

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Abstract

The invention belongs to the technical field of medicine and relates to 1-ethyl-4-[4-[5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1H-indole-1-yl]butyl]piperazine-2,3-dione as well as a medical application, a stereoisomer and pharmaceutically acceptable salt thereof. The structural formula of 1-ethyl-4-[4-[5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1H-indole-1-yl] butyl]piperazine-2,3-dione is represented in the specification; 1-ethyl-4-[4-[5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1H-indole-1-yl]butyl]piperazine-2,3-dione and pharmaceutically acceptable acid addition salt of the compound can be combined with existing drugs or can be independently used as an estrogen receptor modulator for treating or preventing various estrogen function related diseases such as bone loss, fracture, osteoporosis, hectic fever, LDL cholesterol level rise, cardiovascular disease, cognitive impairment, brain degeneration disease and anxiety, as well as depression, sexual dysfunction, hypertension, retinal degeneration and cancer caused by estrogen deficiency, especially osteoporosis.

Description

technical field [0001] The present invention relates to 1-ethyl-4-{4-[5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1H-indol-1-yl]butyl}piperazine-2, The 3-diketone and its preparation method also relate to its application in the preparation of estrogen receptor modulator drugs. Background technique [0002] Compounds that mimic estrogen-like effects have a wide range of therapeutic and prophylactic applications, including: treatment of osteoporosis, relief of menopausal symptoms, treatment of acne, treatment of dysmenorrhea and dysfunctional uterine bleeding, prostate cancer and prevention of cardiovascular disease. [0003] Studies have found that there are two types of estrogen receptors (ER): ERα and ERβ. After the ligand binds to these two isoforms, it exerts physiological effects with different tissue specificities. [0004] What is needed in the art is a compound that can produce a positive response like estrogen replacement therapy but without adverse side effects or with...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06A61K31/496A61P19/08A61P19/10A61P5/30A61P35/00A61P15/00A61P15/12
CPCC07D403/06
Inventor 胡春刘晓平左莉黄二芳张兰金辄
Owner SHENYANG PHARMA UNIVERSITY
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