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Azabicyclic compounds are central nervous system active agents

a technology of azabicyclic compounds and central nervous system, which is applied in the field of azabicyclic compounds and a method for treating pain in mammals, can solve the problems of low clinical efficacy, low clinical efficacy, and low efficacy of azabicyclic compounds in relieving severe or chronic neuropathic pain

Inactive Publication Date: 2006-12-21
DART MICHAEL J +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention is about new compounds and a way to treat pain in mammals. These compounds have a specific formula and can be used to make pharmaceutical products. The compounds have certain features that make them effective in treating pain. The invention is useful for those who need to develop new treatments for pain.

Problems solved by technology

However, clinical use of opioids is commonly associated with potential abuse and addiction liabilities, the development of tolerance, and other side effects such as constipation, nausea, and cognitive impairments.
NSAIDs effectively treat mild-to-moderate pain with an inflammatory component, but they have a ceiling effect and are not particularly effective in relieving severe or chronic neuropathic pain.
One class of pain reliever may not be effective for a particular. patient or group of patients.

Method used

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  • Azabicyclic compounds are central nervous system active agents
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  • Azabicyclic compounds are central nervous system active agents

Examples

Experimental program
Comparison scheme
Effect test

example 1

(cis)-5-(6-chloro-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole hydrochloride

example 1a

(cis)-2,3,3a,4,7,7a-hexahydro-1H-isoindole

[1208] A suspension of lithium aluminum hydride (21.4 g, 0.562 mol) in THF (700 mL) at room temperature was treated with cis-1,2,3,6-tetrahydrophthalimide (Aldrich; 37 g, 0.245 mol) in small portions. The reaction mixture was stirred at 60° C. overnight then cooled to room temperature and quenched carefully by the sequential addition of water (22 mL), THF (22 mL), 15% aqueous KOH (22 mL), and water (80 mL). The mixture was diluted with diethyl ether (100 mL), stirred at room temperature for 1 hour, and then filtered (methylene chloride wash). The filtrate was concentrated under reduced pressure to provide the title compound as an oil (26.1 g). 1H NMR (CDCl3, 300 MHz) δ 1.76-2.02 (m, 2H), 2.10-2.33 (m, 3H), 2.34-2.56 (m, 2H), 2.61-2.79 (m, 2H), 2.87-3.17 (m, 2H), 5.53-6.03 (m, 2H); MS (DCI / NH3) m / z 124 (M+H)+.

example 1b

tert-butyl(cis)-1,3,3a,4,7,7a-hexahydro-2H-isoindole-2-carboxylate

[1209] The product from Example 1A (26 g, 0.21 mol) in methylene chloride (250 mL) at 0° C. was treated with di-tert-butyl dicarbonate (46.1 g, 0.21 mol). The solution was stirred for 30 minutes at 0° C. and then 2 hours at ambient temperature. The reaction mixture was partitioned between methylene chloride and saturated aqueous sodium bicarbonate. The organic extract was washed with saturated aqueous sodium bicarbonate and brine, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (SiO2, 15% ethyl acetate / hexane) to provide the title compound (36 g). 1H NMR (CDCl3, 300 MHz) δ 1.45 (s, 9H), 1.84-1.99 (m, 2H), 2.11-2.40 (m, 4H), 3.07 (m, 1H), 3.18 (m, 1H), 3.33-3.53 (m, 2H), 5.60 (bs, 2H); MS (DCI / NH3) m / z 224 (M+H)+.

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Abstract

Compounds of formula (I) are novel CNS active agents that are useful for treating pain and for treating other disorders associated with the cholinergic system.

Description

FIELD OF THE INVENTION [0001] The present invention is directed to a series of azabicyclic compounds and a method for treating pain in mammals. BACKGROUND OF THE INVENTION [0002] Three major groups of drugs currently used for the treatment of pain include opioids, non-steroidal anti-inflammatory drugs (NSAIDs), and analgesic adjuvants. Opioids such as, but not limited to, morphine act at opioid receptors in the brain and spinal cord to block the transmission of pain signals. However, clinical use of opioids is commonly associated with potential abuse and addiction liabilities, the development of tolerance, and other side effects such as constipation, nausea, and cognitive impairments. NSAIDs typically, but not exclusively, block the production of prostaglandins to prevent sensitization of nerve endings that facilitate the pain signal to the brain. NSAIDs effectively treat mild-to-moderate pain with an inflammatory component, but they have a ceiling effect and are not particularly ef...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D471/02A61K31/4745A61K31/4743A61K31/4741A61K31/426A61K31/433A61K31/42A61K31/4178A61K31/404A61K31/397C07D401/04C07D403/04C07D409/04C07D413/04C07D417/04C07D471/04C07D495/04
CPCC07D401/04C07D403/04C07D409/04C07D495/04C07D417/04C07D471/04C07D413/04
Inventor DART, MICHAEL J.SEARLE, XENIA B.TIETJE, KARIN R.TOUPENCE, RICHARD B.
Owner DART MICHAEL J
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