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Gabapentin analogues for fibromy algia and other disorders

A human and disease technology, applied in the fields of muscular system diseases, neuromuscular system diseases, sexual diseases, etc., can solve the problems of disappointing clinical trial results, limited success of fibromyalgia, etc.

Inactive Publication Date: 2006-01-11
WARNER-LAMBERT CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Single-drug treatments for fibromyalgia have limited success and disappointing clinical trial results

Method used

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  • Gabapentin analogues for fibromy algia and other disorders
  • Gabapentin analogues for fibromy algia and other disorders
  • Gabapentin analogues for fibromy algia and other disorders

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0399]

[0400] Reagents: (i) triethyl phosphonoacetate, NaH; (ii) MeNO 2 , Bu 4 N + f - ;(iii)H 2 , Ni; (iv) HCl

[0401] Synthesis of (trans)-(3,4-dimethylcyclopentylidene)-ethyl acetate (2)

[0402] NaH (60% dispersion in oil, 737mg, 18.42mmol) was suspended in anhydrous THF (50ml) and cooled to 0°C. Triethyl phosphonoacetate (3.83ml, 19.30mmol) was added, and the mixture was stirred at 0°C for 15 minutes. Ketone (1) (1.965 g, 17.54 mmol) in THF (10 ml) was then added and the mixture was allowed to warm to room temperature. After 2 hours, the mixture was partitioned between ether (200ml) and water (150ml). The organic phase was separated, washed with brine, dried (MgSO 4 ), and the solvent was removed in vacuo. The residue was purified by flash layer (silica gel, 1:9 ethyl acetate:heptane) to afford (2) 3.01 g (94%) as a colorless oil.

[0403] 1 H NMR 400MHz (CDCl 3 ): δ1.01 (3H, d, J = 6Hz), 1.03 (3H, d, J = 6Hz), 1.26 (3H, t, J = 7Hz), 1.49 (2H, m), 2.07 (...

Embodiment 2

[0420]

[0421] Reagents: (i) triethyl phosphonoacetate, NaH; (ii) MeNO 2 , Bu 4 N + f - ;(iii)H 2 , Ni; (iv) HCl

[0422] Synthesis of Ethyl Cyclobutylidene Acetate (2)

[0423] NaH (60% dispersion in oil, 1.80 g, 44.94 mmol) was suspended in anhydrous THF (80 ml) and cooled to 0°C. Triethyl phosphonoacetate (9.33ml, 47.08mmol) was added, and the mixture was stirred at 0°C for 15 minutes. Cyclobutanone (1) (3.0 g, 42.8 mmol) in THF (20 ml) was then added and the mixture was allowed to warm to room temperature. After 2 hours, the mixture was partitioned between ether (200ml) and water (150ml). The organic phase was separated, washed with brine, dried (MgSO 4 ) and the solvent was removed in vacuum at 600 mm Hg. The residue was purified by flash layer (silica gel, 1:19 ethyl acetate:pentane) to afford (2) 5.81 g (96%) as a colorless oil.

[0424] 1 H NMR 400MHz (CDCl 3 ): δ1.27(3H, t, J=6Hz), 2.09(2H, m), 2.82(2H, m), 3.15(2H, m), 4.14(2H, q, J=6Hz), 5.58(1H , s)....

Embodiment 3

[0438]

[0439] Reagents: (i) triethyl phosphonoacetate, NaH; (ii) MeNO 2 , Bu 4 N + f - ;(iii)H 2 , Ni; (iv) HCl

[0440] Synthesis of (R)-(3-methylcyclopentylidene)-ethyl acetate (2)

[0441] NaH (60% dispersion in oil, 1.86 g, 46.5 mmol) was suspended in anhydrous THF (40 ml) and cooled to 0°C. Triethyl phosphonoacetate (9.69ml, 48.8mmol) was added, and the mixture was stirred at 0°C for 15 minutes. Ketone (1) (5ml, 46.5mmol) in THF (10ml) was then added and the mixture was allowed to warm to room temperature. After 2 hours, the mixture was partitioned between ether (200ml) and water (150ml). The organic phase was separated, washed with brine, dried (MgSO 4 ), and the solvent was removed in vacuo. The residue was purified by flash layer (silica gel, 1:9 ethyl acetate:heptane) to afford (2) 5.45 g (70%) as a colorless oil.

[0442] 1 H NMR 400MHz (CDCl 3 ): δ1.04(3H, m), 1.27(3H, t, J=7Hz), 1.80-2.74(7H, m), 2.90-3.15(1H, m), 4.13(2H, q, J=7Hz) , 5.76 (1H, s)...

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PUM

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Abstract

This invention provides compounds of formulas (I) and (II) or the salt thereof acceptable in pharmacy, and the new use thereof for the treatment of fibromyalgia or others.

Description

technical field [0001] The present invention relates to the use of α2δ ligands in the treatment of fibromyalgia and other central nervous system disorders. Background technique [0002] Fibromyalgia (FM) is a chronic syndrome characterized by protracted pain, nonrestorative sleep, mood disturbance, and fatigue. The main symptoms of fibromyalgia include pain, sleep, mood disturbance, and fatigue. The syndromes associated with fibromyalgia include irritable bowel syndrome and migraine. The success of treating fibromyalgia with single agents has been limited and clinical trial results have been disappointing. Based on the current understanding of the mechanisms and pathways involved in fibromyalgia, it is believed that there is a need for multiple drugs that target key symptoms such as pain, sleep disturbance, mood disturbance, and fatigue. Patients with fibromyalgia are often sensitive to drug side effects, a feature that may be related to the pathology of the condition (Ba...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/195A61P25/18A61P43/00A61K31/00A61K31/16A61K31/18A61K31/185A61K31/197A61K31/198A61K31/20A61K31/401A61K31/4015A61K31/41A61K31/4245A61K31/433A61K31/662A61K45/06A61P1/00A61P9/00A61P11/00A61P11/14A61P13/00A61P15/00A61P17/00A61P25/00A61P29/00A61P35/00A61P37/00
CPCA61K31/20A61K31/18A61K31/198A61K31/185A61K31/197A61K31/662A61K45/06A61K31/16A61K31/433A61K31/00A61K31/4015A61K31/41A61K31/4245A61K31/401A61K31/195A61P1/00A61P11/00A61P11/14A61P13/00A61P13/10A61P15/00A61P15/08A61P15/10A61P17/00A61P17/06A61P19/02A61P21/02A61P25/00A61P25/04A61P25/08A61P25/14A61P25/18A61P25/20A61P25/24A61P25/28A61P29/00A61P31/18A61P35/00A61P3/06A61P37/00A61P43/00A61P5/00A61P9/00A61P9/06A61P9/10
Inventor D·J·杜利C·P·小泰勒A·J·索普D·J·伍斯特罗
Owner WARNER-LAMBERT CO
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