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1,3,8-triaza-spiro[4.5]decane-4-ketone compounds and pharmaceutical application thereof

A compound and triaza technology, applied in 1 field, can solve problems such as addiction and poor pharmacokinetic properties

Inactive Publication Date: 2012-09-26
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, these compounds are structurally too similar to opioid analgesics such as fentanyl, which may be potentially addictive; on the other hand, these compounds have poor pharmacokinetic properties and require extracerebroventricular administration It is not a simple and easy route of administration to produce analgesic activity in clinical practice. Therefore, there is still a demand for the development of new N-type calcium ion channel blockers

Method used

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  • 1,3,8-triaza-spiro[4.5]decane-4-ketone compounds and pharmaceutical application thereof
  • 1,3,8-triaza-spiro[4.5]decane-4-ketone compounds and pharmaceutical application thereof
  • 1,3,8-triaza-spiro[4.5]decane-4-ketone compounds and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Example 1: (±) 8-(3-methoxy-benzoyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decane-4-one (401)

[0106] Take 0.11g (about 0.0005mol) of 1-phenyl-1,3,8-triaza-spiro[4.5]decane-4-one and put it in a 50ml ground-mouth Erlenmeyer flask, add 0.5g of anhydrous potassium carbonate , acetone 30ml, slightly excess 3-methoxybenzoyl chloride (0.15ml, about 0.0012mol), stirred at room temperature for 12 hours, TLC (Cl 2 CH 2 :CH 3 OH 5:1) to monitor the reaction, until the raw material point disappears, add 30ml of water and 30ml of dichloromethane after spin-drying, after separation, dry with anhydrous sodium sulfate, spin-dry after filtering, add a small amount of acetone to dissolve, add ether with hydrogen chloride to precipitate The solid was filtered with suction, and the solid was recrystallized with acetone / anhydrous ether, and after drying, 0.12 g of the product was obtained, with a yield of 66.7%. m.p.216-218°C. m + +1(m / z): 365. 1 HNMR (DMSO-d 6 , ppm) δ: 7.35-7.39 (t, 1...

Embodiment 2

[0107]Example 2: (±) 8-(3-Methyl-butyryl)-1-phenyl-1,3,8-triaza-spiro[4.5]decane-4-one (402)

[0108] Prepared according to the synthetic method of compound 401. The raw materials are 1-phenyl-1,3,8-triaza-spiro[4.5]decane-4-one 0.11g (about 0.0005mol) and a little excess isovaleryl chloride (0.15ml, about 0.001mol) . 0.12 g of the target compound was obtained with a yield of 76.4%. m.p.80-82°C. m + +1 (m / z): 345.

Embodiment 3

[0109] Example 3: (±)(1-Phenyl-1,3,8-triaza-spiro[4.5]decane-4-one-8-yl)-one-acetate methyl ester (403)

[0110] Prepared according to the synthetic method of compound 401. The raw materials are 0.11g (about 0.0005mol) of 1-phenyl-1,3,8-triaza-spiro[4,5]decane-4-one and a slight excess of methyl oxalyl chloride (0.15ml, about 0.0013mol). 0.10 g of the target compound was obtained with a yield of 69.2%. m.p.178-180°C. m + +1 (m / z): 318.

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Abstract

The invention relates to 1,3,8-triaza-spiro[4.5]decane-4-ketone compounds shown by a general formula I. Isomers, optical isomers, racemates or medicine salts of the 1,3,8-triaza-spiro[4.5]decane-4-ketone compounds contain the medical combinations thereof. The compounds are used for preparing, or preventing or treating various pains such as postoperative pain, migraine, visceral pain, neuropathic pain and the like and such diseases as addition and tolerance caused by analgesic drugs.

Description

technical field [0001] The present invention relates to 1,3,8-triaza-spiro[4.5]decane-4-one compounds, their optical antipodes, racemates or pharmaceutically acceptable salts, their preparation methods, and their medicines Compositions, and the use of such compounds for the preparation of medicines for preventing and / or treating pain, addiction and tolerance caused by opioids and other analgesic drugs. Background technique [0002] Pain is a common symptom of many diseases. The current research results show that N-type calcium ion channels are an important link in the process of pain generation and pain transmission, because the blockers for N-type calcium ion channels directly act on N-type calcium ion channels. channels, do not involve second messengers or G proteins, and are therefore less prone to addiction. Highly selective N-type calcium ion channel blocker ω-conotoxin (ω-conotoxin) MVIIA In December 2004, it was approved by the US FDA to enter the market. Its clini...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/10A61K31/438A61P25/04A61P25/30
Inventor 恽榴红李锦郑健全蒋兴凯张城吴宁张树卓
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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