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Preparation method and intermediate of fused tricyclic derivative

A compound and mixture technology, applied in the field of medicine, can solve problems such as low safety, abused patients, and dependence

Active Publication Date: 2020-08-11
SICHUAN HAISCO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, for gabapentin, the proportion of improving the pain of patients with diabetic peripheral neuropathy is about 60% (Acta Neurol. Scand. 101:359-371, 2000), for pregabalin, although its tolerance is better than gabapentin , but its safety is lower, and it has the possibility of abuse or making patients dependent (Am J Health SystPharm.2007; 64(14):1475-1482)

Method used

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  • Preparation method and intermediate of fused tricyclic derivative
  • Preparation method and intermediate of fused tricyclic derivative
  • Preparation method and intermediate of fused tricyclic derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0115]

[0116] The first step: cyclopent-3-en-1-ylbenzenesulfonate (1-2)

[0117]

[0118] Dissolve cyclopent-3-en-1-ol (5 g, 59 mmol) in dichloromethane (150 mL) and cool to 0°C. Triethylamine (14 mL) was added, and phenylsulfonyl chloride (12.6 g, 71 mmol) was added dropwise. Natural heating. Stir for 1 hour. Cool to 0°C, adjust the pH to about 4 with concentrated hydrochloric acid, and add water (100ml). Extracted with ethyl acetate (150 mL×3). Dry (anhydrous sodium sulfate), spin dry. The residue was separated and purified by column chromatography (petroleum ether / ethyl acetate=10:1) to obtain cyclopent-3-en-1-ylbenzenesulfonate 1-2 (11.5 g, yield 86.3%), 1 H NMR (400MHz, CDCl 3 )δ7.95–7.86(m,2H),7.68–7.60(m,1H),7.56(d,J=7.9Hz,2H),5.71–5.60(m,2H),5.25–5.13(m,1H) ,2.71–2.42(m,4H).

[0119] The second step: ethyl 4-(cyclopent-3-en-1-yl)-3-oxobutyrate (1-3)

[0120]

[0121] Sodium hydride (0.43 g, 11 mmol, 60%) was put into dry THF (15 mL), protected by ni...

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Abstract

The invention provides a preparation method and an intermediate of a fused tricyclic derivative. The fused tricyclic derivative has a structure shown as a formula (I). The preparation method has the advantages of accessible raw materials and simple steps and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the field of medicine, in particular, the invention relates to a preparation method and an intermediate of a fused tricyclic derivative. Background technique [0002] Voltage-gated calcium channels are composed of α1 subunits and accessory proteins α2δ, β, and γ subunits. α2δ protein can regulate the density and voltage-dependent dynamics of calcium channels (Felix et al(199 7) J.Neuroscience 17:6884-6891; Klugbauer et al(1999) J.Neuroscience 19:684-691; Hobom et al. al (2000) Eur. J. Neuroscience 12:1217-1226; and Qin et al (2002) Mol. Pharmacol. 62:485-496). Compounds that exhibit high affinity binding to the voltage-dependent calcium channel subunit α2δ have been shown to be effective in the treatment of pain, such as pregabalin and gabapentin. In mammals, there are four subtypes of α2δ protein, each of which is encoded by a different gene. α2δ subtype 1 and 2 showed high affinity for pregabalin, whereas α2δ subtype 3 and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/62C07C49/453C07C303/28C07C309/73C07C67/343C07C69/738C07C67/31C07C69/732C07C27/02C07C59/46C07C45/45C07C49/643
CPCC07C45/62C07C49/453C07C303/28C07C309/73C07C67/343C07C69/738C07C67/31C07C69/732C07C51/09C07C59/46C07C45/45C07C49/643C07C2601/10C07C2603/66
Inventor 李瑶李升石宗军陈雷王文晶张国彪张晨严庞科郑伟
Owner SICHUAN HAISCO PHARMA CO LTD