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Substituted pyrrolopyridinone derivatives useful as phosphodiesterase inhibitors

a technology of pyrrolopyridinone and derivatives, which is applied in the field of substituted pyrrolopyridinone derivatives, can solve the problems of ed, side effects, fibrosis, etc., and achieve the effects of reducing the risk of ed

Inactive Publication Date: 2005-05-26
SUI ZHIHUA +4
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0015] It is another object of the invention to identify compounds which are useful for the treatment of conditions of disorders mediated by PDEV, such as male erectile dysfunction, female sexual dysfunction, cardiovascular disorders, atherosclerosis, arterial occlusive disorders, thrombosis, coronary reststenosis, angina pectoris, myocardial infarction, heart failure, ischemic heart disorders, hypertension, pulmonary hypertension, asthma, intermittent claudication or diabetic complications.

Problems solved by technology

In addition, patients who take certain classes of drugs such as antihypertensives, antidepressants, sedatives, and anxiolytics are more prone to suffer from ED.
These agents are only effective after direct intracavernosal or intraurethral injection, and are associated with side effects such as priapism, fibrosis, penile pain and hematoma at the injection site.
Although this form of therapy is frequently successful in ED of organic origin, complaints include the lack of spontaneity and the time involved in using a mechanical device, and difficulty and discomfort with ejaculation.
These devices are generally considered when other treatment options have failed, and are associated with an increased risk of infection and ischemia.
However, the drug showed less dramatic efficacy in patients who had undergone a radical prostatectomy, with improved erections in 43% of patients who took sildenafil versus 15% on placebo.
In addition, the use of sildenafil is associated with several undesirable side effects including headache, flushing and disrupted color vision which result from non-selective effects on a variety of tissues.

Method used

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  • Substituted pyrrolopyridinone derivatives useful as phosphodiesterase inhibitors
  • Substituted pyrrolopyridinone derivatives useful as phosphodiesterase inhibitors
  • Substituted pyrrolopyridinone derivatives useful as phosphodiesterase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

example 1

1-(3,4-Methylenedioxyphenyl)-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline

[0134] To a solution of the 1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-O-carboline (prepared according to the process as disclosed in WO97 / 43287, Intermediate 7, page 24) (7.37 g, 25 mmol) in dry DMF (25 mL) was added triethylamine (3.52 mL, 25 mmol) and benzyl bromide (3.00 mL, 25 mmol). The mixture was stirred at ambient temperature overnight and added dropwise to a solution of sodium hydroxide (25 mmol) in water (200 mL). A precipitate was formed, collected by vacuum filtration, washed with water (2×50 mL), and dried in vacuo overnight to yield the product as a freely flowing pale yellow powder.

[0135] MS (m / z) 383 (MH+)

[0136]1H NMR (CDCl3) δ 2.57-2.89 (series of m, 3H), 3.18-3.23 (m, 1H), 3.33 (d, J=13.7 Hz, 1H), 3.63 (d, J=13.7 Hz, 1H), 4.55 (s, 1H), 5.94 (nd, J=2.2 Hz, 2H), 6.77-7.52 (series of m, 13H).

example 1a

(R)-1-(3,4-Methylenedioxyphenyl)-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline

[0137] Following the procedure as described in Example 1, (R)-1-(3,4,-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline was reacted to produce the title compound.

[0138] MS (m / z) 383 (MH+)

example 2

1-(2,3-Dihydrobenzofuran-5-yl)-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline

[0139] The title product was prepared according to the process described in Example 1 using 1-(2,3-dihydrobenzofuran-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline as the starting reagent.

[0140] MS (m / z) 381 (MH+)

[0141]1H NMR (CDCl3) δ 2.59-2.90 (series of m, 3H), 3.13-3.24 (m, 3H), 3.33 (d, J=13.5 Hz, 1H), 3.93 (d, J=13.5 Hz, 1H), 4.56 (t, J=8.6 Hz, 2H), 6.75 (d, J=8.1 Hz, 1H), 7.05-7.35 (series of m, 10H), 7.49-7.52 (m, 1H)

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Abstract

The invention relates to novel pyrrolopyridinone derivatives of the formula (I) or (II): pharmaceutical compositions containing the compounds and their use for the treatment of sexual dysfunction.

Description

CROSS REFERENCE TO RELATED APPLICATION [0001] This application claims priority from U.S. provisional application Ser. No. 60 / 204,646 filed May 17, 2000, the contents of which are hereby incorporated by reference.FIELD OF THE INVENTION [0002] The invention relates to novel pyrrolopyridinone derivatives, intermediates used in, synthesis of and pharmaceutical compositions containing the compounds and their use for the treatment of sexual dysfunction. The compounds of the present invention are phosphodiesterase inhibitors useful for the treatment of sexual dysfunction, more particularly male erectile dysfunction. BACKGROUND OF THE INVENTION [0003] Erectile dysfunction (ED) is defined as the inability to achieve or maintain an erection sufficiently rigid for satisfactory sexual intercourse. Currently it is estimated that approximately 7-8% of the male population suffer from some degree of ED, the equivalent of at least 20 million men in the United States alone. Since the likelihood of ED...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/437A61K31/4709A61K31/496A61K31/506A61K31/5377A61P3/10A61P7/02A61P9/00A61P9/04A61P9/10A61P9/12A61P11/06A61P15/00A61P15/02A61P15/06A61P15/08A61P15/10A61P43/00C07D471/04
CPCC07D471/04A61P11/06A61P15/00A61P15/02A61P15/06A61P15/08A61P15/10A61P43/00A61P7/02A61P9/00A61P9/04A61P9/10A61P9/12A61P3/10
Inventor SUI, ZHIHUAMACIELAG, MARK J.GUAN, JIHUAJIANG, WEIGINLANTER, JAMES C.
Owner SUI ZHIHUA
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