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Compounds for treating fibromyalgia and chronic fatigue syndrome

A technology for chronic fatigue and fibromyalgia, applied in the direction of active ingredients of heterocyclic compounds, drug combinations, organic chemistry, etc., can solve problems such as damage, no permanent elimination, addiction to the liver, etc.

Inactive Publication Date: 2004-12-15
PHARMACIA & UPJOHN CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no known medications that permanently eliminate the symptoms of CFS or FMS
Additionally, many of the drugs currently in use produce side effects ranging from mild side effects such as drowsiness, dizziness and nausea to serious side effects such as addiction and liver damage

Method used

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  • Compounds for treating fibromyalgia and chronic fatigue syndrome
  • Compounds for treating fibromyalgia and chronic fatigue syndrome
  • Compounds for treating fibromyalgia and chronic fatigue syndrome

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0115] 1-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (II)

[0116] 4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (I, J.Heterocyclic Chem., 19,837-49(1982) 1.0g, 5.8 mmol) and DMF (10ml) was cooled to 0°C and then treated with a mixture of potassium tert-butoxide and THF (1.98M, 3.2ml, 6.3mmol) keeping the reaction temperature at 0°C. The resulting mixture was stirred at 0°C for 10 minutes. Then benzyl bromide (0.73ml, 6.1mmol) was added while maintaining the reaction temperature, extracted from water with methyl tert-butyl ether (MTBE), and washed several times with water. The MTBE phase was concentrated under reduced pressure. The concentrate was cooled to 0°C, filtered and rinsed twice with 0°C MTBE. The product was dried by blowing nitrogen gas under reduced pressure at 50° C. to obtain the title compound, CMR (CDCl 3 , 100MHz) 153.78, 136.44, 128.69, 127.67, 127.60, 126.73, 125.86, 122.90, 122.78, 121.28, 116.92, 116.17, 108.36, 44.95 and 42.37δ.

Embodiment 2

[0118] (5R,6R)-1-benzyl-5-bromo-6-hydroxyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one ( III) 1-benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (II, Example 1, 240 g), acetonitrile (1.086 kg), water (227 ml) and Fluoroboric acid (48.5%, 13.4 g) was mixed and cooled to 0 to 5°C. Dibromantin (163.5 g) was homogenized with acetonitrile and added to the reaction mixture. The reaction is carried out at 0 to 5°C for about 3 hours. After the reaction was completed, methyl tert-butyl ether was added in about 45 minutes under the condition that the temperature of the reactor was lower than 10°C. The slurry was cooled to 10-15°C, stirred for 1 hour, then filtered. The product was rinsed with pre-cooled methyl tert-butyl ether, and dried under nitrogen at 40°C to obtain the title compound CMR(CDCl 3 ) 156.0, 137.8, 130.5, 129.6, 129.3, 129.1, 126.6, 123.6, 122.5, 119.6, 110.4, 69.9, 49.6, 47.7, 46.9 and 43.8δ.

Embodiment 3

[0120] (5S, 6S)-1-benzyl-5-bromo-2-oxygen-1,2,5,6-tetrahydro-4H-imidazo[4,5,1-ij]quinolin-6-yl ( 2R)-(6-methoxy-2-naphthyl)propionate (IVA) and (5R,6R)-1-benzyl-5-bromo-2-oxo-1,2,5,6-tetra Hydrogen-4H-imidazo[4,5,1-ij]quinolin-6-yl (2R)-(6-methoxy-2-naphthyl)propionate (IVB) will (5R,6R)- 1-Benzyl-5-bromo-6-hydroxy-5,6 dihydro-imidazo[4,5,1-ij]quinolin-2(1H)-one (III, Example 2, 143g), di Chloromethane (3.136g), N-methylmorpholine (100.2g) and 4-dimethylaminopyridine (497g) were added to the reactor and the mixture was cooled to 0 to 5°C. (R) Naproxen chloride (Formulation 1, 118.5 g) dissolved in dichloromethane (694 ml) was added to the reactor over about 1 hour and the mixture was stirred at 0 to 5°C to complete the reaction. If necessary, additional naproxen chloride was added to complete the reaction. Potassium carbonate diluted with water was added to the mixture. The aqueous phase was extracted with dichloromethane and the combined dichloromethane phases were washed...

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Abstract

The present invention provides for the use of a heterocyclic amine-type compound to prepare a medicament for the treatment of symptoms of fibromyalgia syndrome, or chronic fatigue syndrome.

Description

[0001] The present invention is a divisional application of the Chinese patent application submitted on April 17, 2001 with the application number 01806849.9 and the title of the invention "Compounds for the Treatment of Fibromyalgia and Chronic Fatigue Syndrome". technical field [0002] The invention relates to the use of heterocyclic amine compounds for preparing medicines for treating fibromyalgia syndrome and chronic fatigue syndrome. Background technique [0003] Chronic Fatigue Syndrome (CFS), also known as Chronic Fatigue Immunodeficiency Syndrome, Young Urban Professional (yuppie) Epidemic; Fatigue-Chronic, and Chronic Fatigue and Immunodeficiency Syndrome, are clinically defined as having A condition characterized by profound exhaustion or fatigue. In addition, patients with CFS often have a variety of nonspecific symptoms, including weakness, muscle pain, lethargy, malaise, fever, sore throat, lymph node tenderness, memory los...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/24A61K31/445A61K31/451A61K31/4745A61K31/48A61K45/00A61P21/00A61P43/00C07D471/06
CPCA61K31/48A61K31/451A61K31/445A61K31/4745A61P21/00A61P29/00A61P43/00
Inventor R·B·麦考R·C·玛沙尔D·W·罗伯特森T·M·阿施勒
Owner PHARMACIA & UPJOHN CO
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