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Benzopyranopyrrole and benzopyranopyridine alpha-1 adrenergic compounds

A compound, halogen technology, applied in the field of benzopyranopyrrole and benzopyranopyridine alpha-1 adrenergic compounds

Inactive Publication Date: 2000-03-08
ABBOTT LAB INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these agents have similar dose-limiting side effects: hypotension, dizziness, and muscle fatigue

Method used

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  • Benzopyranopyrrole and benzopyranopyridine alpha-1 adrenergic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0342] Example 13-[4-((3aR, 9bR)-cis-9-methoxy-1.2.3.3a.4.9b-hexahydro-[1]-benzopyrano[3,4-c]pyrrole -2-yl)butyl]-pyrido[2',3':4,5]thieno[3,2-d]pyrimidine-

[0343] 2,4(1H,3H)-Diketone Hydrochloride

Embodiment 1A

[0344] Example 1A (3aR, 9bR)-cis-9-methoxy-2-(R)-α-methylbenzyl-1,2,3,3a,4,9b-hexahydro-

[0345] [1]-Benzopyrano[3,4-c]pyrrol-4-one

[0346] 5-Methoxycoumarin (22.3 g, 126 mmol) and trifluoroacetic acid (0.97 mL, 12.6 mmol) were dissolved in CH 2 Cl 2 (200mL) and cooled to 0°C. To the stirred solution was added N-methoxymethyl-N-trimethylsilylmethyl-(R)-α-methylbenzylamine (63.4 g, 252 mmol) over 30 minutes. The reaction was stirred at 0°C for an additional 30 minutes, then at 25°C for 1 hour. The reaction mixture was washed with 5% NaHCO 3 After washing, the organic layer was dried and evaporated. The resulting oil was suspended in ether, and after 2 hours, the title compound was collected by filtration (15.4 g, 38%). 1 HNMR (300MHz, CDCl 3 )δ1.36(d, 3H), 2.41(dd, 1H), 3.04(d, 1H), 3.05-3.15(m, 2H), 3.23(m, 1H), 3.32(1, 1H), 3.75(m , 1H), 3.79 (s, 3H), 6.61 (d, 1H), 6.67 (d, 1H), 7.18 (t, 1H), 7.20-7.35 (m, 5H).

Embodiment 1B

[0347] Example 1B (3aR, 9bR)-cis-9-methoxy-2-(R)-α-methylbenzyl-1,2,3,3a,4,9b-hexahydro-

[0348] [1]-Benzopyrano[3,4-c]pyrrole

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Abstract

The present invention relates to a compound of formula (I) and the pharmaceutically acceptable salts thereof wherein W is a bicyclic heterocyclic ring system. The compounds are alpha-1 adrenergic antagonists and are useful in the treatment of BPH; also disclosed are alpha-1 antagonist compositions and a method for antagonizing alpha-1 adrenoreceptors and treating BPH.

Description

[0001] This application is a continuation-in-part of US Patent Application Serial No. 08 / 761,423, filed December 6,1996. 1. Technical field [0002] The present invention relates to novel organic compounds and compositions that are alpha-1 adrenergic receptor antagonists, processes for the preparation of such compounds, synthetic intermediates useful in these processes, and the inhibition of alpha-1 adrenergic receptors and the treatment of benign Prostatic hyperplasia (BPH), also known as benign prostatic hypertrophy or other urological disorders such as bladder outlet obstruction and neurogenic bladder or gynecological syndromes such as dysmenorrhea. 2. Background of the invention [0003] Adrenergic neurons play a major role in the innervation of heart, blood vessels and smooth muscle tissue. Compounds capable of interacting with adrenergic receptor sites in adrenergic nerves elicit a variety of physiological responses, including vasoconstriction, vasodilation, and increa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/517A61K31/519A61P13/08A61P13/10A61P15/04A61P43/00C07D207/26C07D311/58C07D491/04C07D491/052C07D495/04C07D519/00
CPCC07D491/04A61P13/08A61P13/10A61P15/04A61P43/00
Inventor M·D·梅耶尔R·J·阿尔藤巴赫F·巴沙W·A·卡洛尔I·德里津J·F·克尔温M·D·温德特A·R·黑特W·J·张
Owner ABBOTT LAB INC
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