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Tetrahydropyridine [4,3-b] diindyl compound as well as preparation method and pharmaceutical application thereof

A tetrahydropyridine, 3-b technology, applied in the field of medicinal chemistry and chemotherapy, can solve the problems of poor urethral selectivity and the like

Inactive Publication Date: 2015-06-17
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But due to the early listing of alpha 1 - AR antagonists are not very selective for the urethra and are often accompanied by a series of side effects such as dizziness and orthostatic hypotension. Therefore, enhancing tissue selectivity to reduce cardiovascular and other side effects becomes α 1 -Important research directions of AR antagonists

Method used

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  • Tetrahydropyridine [4,3-b] diindyl compound as well as preparation method and pharmaceutical application thereof
  • Tetrahydropyridine [4,3-b] diindyl compound as well as preparation method and pharmaceutical application thereof
  • Tetrahydropyridine [4,3-b] diindyl compound as well as preparation method and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of 8-fluoro-2,3,4,5-tetrahydropyridine(4,3-b)indole hydrochloride

[0031] 4.86g (30mmol) of 4-fluorophenylhydrazine hydrochloride, 4.60g (30mmol) of 4-piperidone hydrochloride-hydrate and 25mL of absolute ethanol were added to a 100mL three-necked flask, stirred at reflux for 2 hours, and the reaction was stopped. Naturally cool to room temperature, stand overnight, filter, wash the filter cake with 5 mL of 50% ethanol-water solution, and dry to obtain 5.35 g of light yellow crystals. Then recrystallized with 40 mL of 80% ethanol to obtain 3.0 g of yellow crystals. Yield 44.2%, m.p.>220°C decomposition.

Embodiment 2

[0033] Preparation of 8-methoxy-2,3,4,5-tetrahydropyridine(4,3-b)indole hydrochloride

[0034] Referring to the preparation method of Example 1, synthesized from 5.24 g (30 mmol) of 4-methoxyphenylhydrazine hydrochloride and 4.06 g (30 mmol) of 4-piperidone hydrochloride monohydrate to obtain 4.20 g of off-white powder. Yield 58.7%, m.p.>220°C decomposition.

Embodiment 3

[0036] Preparation of 6-chloro-2,3,4,5-tetrahydropyridine(4,3-b)indole hydrochloride

[0037] Referring to the preparation method of Example 1, synthesized from 5.37 g (30 mmol) of 2-chlorophenylhydrazine hydrochloride and 4.60 g (30 mmol) of 4-piperidone hydrochloride monohydrate to obtain 2.50 g of off-white powder. Yield 34.4%, m.p.>220°C decomposition.

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Abstract

The invention discloses a tetrahydropyridine [4,3-b] diindyl compound, as well as a preparation method and a pharmaceutical application thereof. The structure formula of the tetrahydropyridine [4, 3-b] diindyl compound is shown in a formula (A), wherein R1 is 7,8 disubstituted alkyl, 6 or 8 substituted halogen and alkoxy 8 substituted; R2 is 2 substituted alkoxy; n is 1 or 2. The invention further discloses a preparation method of the tetrahydropyridine [4, 3-b] diindyl compound and an application in preparation of a medicine for treating benign prostatic hyperplasia and lower urinary tract syndromes caused by the benign prostatic hyperplasia.

Description

technical field [0001] The present invention relates to a class of tetrahydropyridine[4,3-b]indole derivatives represented by general formula (A) with novel structure, its synthesis method and its preparation method for the treatment of α 1 Adrenergic receptor-related diseases, especially benign prostatic hyperplasia and the application of drugs to lower urinary tract syndrome caused by it. The present invention relates to the fields of medicinal chemistry and chemotherapeutics. Background technique [0002] Benign prostatic hyperplasia (Benign Prostatic Hypertensia, hereinafter referred to as BPH) is a common urinary system disease in elderly men. Its pathogenesis is complex and related to a variety of enzymes and receptors. So far, the means of treating BPH include conservative drug treatment and surgical resection treat. There are two main categories of chemical drugs clinically used to treat BPH: α 1 - AR antagonists and 5α-reductase inhibitors. where α 1 -AR antago...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61P13/08A61P13/00
CPCC07D471/04
Inventor 李嘉宾孙崇振陈孟华江振洲严明薛晓文
Owner CHINA PHARM UNIV