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Substituted pyrrolidine and piperidine compounds, derivatives thereof, and methods for treating pain

A compound, chemical formula technology, applied in the field of substituted pyrrolidine and piperidine compounds

Inactive Publication Date: 2011-04-27
CHLORION PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Furthermore, the tolerability of neuropathic pain treatments on the market has yet to be improved; in a recent review of several clinical studies, for example, pregabalin was reported to cause significant drowsiness, dizziness, and headache, and often resulted in More than 3 / 10 subjects withdraw from clinical trials (Tassone et al., Clinical Therapeutics, 2007)

Method used

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  • Substituted pyrrolidine and piperidine compounds, derivatives thereof, and methods for treating pain
  • Substituted pyrrolidine and piperidine compounds, derivatives thereof, and methods for treating pain
  • Substituted pyrrolidine and piperidine compounds, derivatives thereof, and methods for treating pain

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0761] Compounds of formula (Ia) and (Ib) were prepared by utilizing the general procedure as shown in Scheme 2 below.

[0762]

[0763] Scenario 2

[0764] To a mixture of pyrrolidine compounds, for example, (S)-(+)-3-fluoropyrrolidine hydrochloride (2.0 g, 15.9 mmol) in dry acetonitrile (30 mL), was added potassium carbonate (4.83 g, 35.0 mmol). The mixture was stirred at room temperature for 5 minutes before adding 2-bromoacetamide (2.08 g, 15.1 mmol). The mixture was stirred overnight at reflux. Strain the hot mixture. The filtrate was recovered, evaporated under reduced pressure and dried in vacuo to provide the described compound.

[0765] Preparation of 2-(1,3-thiazolidin-3-yl)acetamide:

[0766]

[0767] (1.01g, 21%). 1 H NMR (400MHz, DMSO-d6) 2.78(t, J=6.5Hz, 2H), 2.87(s, 2H), 3.00(t, J=6.3Hz, 2H), 7.16(s(br), 1H), 7.35 (s(br), 1H), M+147.

[0768] Preparation of 2-[(3S)-3-fluoropyrrolidin-1-yl]acetamide:

[0769]

[0770] (1.91g, 87%). 1 H NMR (400...

Embodiment 2

[0822] Example 2: Analgesic effect of compounds of the present invention

[0823] Determination of analgesic effects in experimental models of neuropathic pain

[0824] Using the procedure described hereafter, it was determined that 2-(pyrrolidin-1-yl)acetamide, 3-(piperidin-1-yl)propionamide, 3-[(3S)-3-fluoropyrrolidin-1-yl ] propionamide, and the analgesic effect of 3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl] propionamide. Other methods are known to the skilled person.

[0825] Adult, male St.-Dow rats were obtained from Charles River Laboratories (St Constant, QC) and housed under standard conditions at the Institut Armand Frappier (Laval, QC). Experimental animals were provided food and water ad libitum and rats weighed 175-200 grams at the time of evaluation.

[0826] Compounds for intrathecal administration were prepared by dissolving the compounds in a vehicle of D5W (5% glucose); the total volume of solution administered to rats was 20 ul, and the amount of exemplary ...

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Abstract

The present application relates to pyrrolidine, piperidine, and other nitrogen-containing heterocyclic derivatives and the use of these compounds for treating and preventing pam or inflammation. The analgesic compounds demonstrate efficacy in the treatment of neuropathic pain resulting from a variety of conditions such as diabetic neuropathy, HIV infections, and post-herpetic neuralgia.

Description

[0001] References to related applications [0002] This application claims the benefit of US Provisional Application No. 61 / 038,662, filed March 21, 2008, which is incorporated herein by reference. Background technique [0003] In general, the present invention relates to substituted pyrrolidine and piperidine compounds, and their derivatives, and the use of these compounds in the treatment of pain. [0004] Pain is a common form of physical pain and discomfort and is one of the most common reasons patients refer to their physicians. They can be classified by form (nociceptive or neuropathic), duration (chronic or acute), and degree (mild, moderate, or severe). Typically, nociceptive pain is acute and results from injury, such as burns, sprains, bone fractures, inflammation (inflammatory pain, including from osteoarthritis and rheumatoid arthritis). Neuropathic pain, on the other hand, is defined by the International Association for the Study of Pain as a form of chronic pai...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/10A61K31/164A61K31/40A61K31/41A61K31/445A61P29/00C07C233/08C07D209/04C07D211/36C07D265/02C07D277/04
CPCC07D207/10C07D211/36C07D265/02C07D277/04C07D209/04A61P25/04A61P29/00A61P29/02
Inventor 乔治·拉塔多萨斯米塔·塔里帕西
Owner CHLORION PHARMA
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