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Application of long-acting low-addiction compound in preparation of medicine

A compound and drug technology, applied in long-acting and low-addiction compounds, in the application field of diseases, can solve problems such as limiting the long-acting effect of depression and adverse physical and mental effects of patients, and achieve the effect of long drug effect time

Active Publication Date: 2021-03-19
SHENZHEN RUIJIAN BIOSCI TECH LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In our experimental study, we found that (2R,6R; 2S,6S)-hydroxynorketamine (HNK) does not last long after administration, and basically has no activity within 1 week, which seriously limits the treatment Desired long-term effect in depression
At the same time, our research also found that the application of HNK will produce a certain degree of addiction, which will cause adverse effects on the patient's body and mind.

Method used

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  • Application of long-acting low-addiction compound in preparation of medicine
  • Application of long-acting low-addiction compound in preparation of medicine
  • Application of long-acting low-addiction compound in preparation of medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Embodiment 1: the synthesis of (2R,6R)-6-hydroxy demethyl ketamine (HNK)

[0088]

[0089] Step 1: In a two-neck bottle or a three-necked bottle, add 50 grams of magnesium powder, and slowly add a mixed solution of 119.2 grams of bromocyclopentane and THF dropwise after initiation. After the dropwise addition, reflux for 2-4 hours to obtain 1.6mol / L Cyclopentyl Grignard Reagent. Add 840 mg of CuBr to the mixture of THF and o-chlorobenzonitrile (50.0 g), and add cyclopentyl Grignard reagent (1.6 mol / L, 280 ml) dropwise under ice-bath conditions. Reflux for 1 hour after the dropwise addition, cool to room temperature, add 100ml of water, then add 200ml of 15% dilute sulfuric acid solution, stir overnight, spin dry THF, extract with EA, dry, and pass through a silica gel column to obtain compound A 2-chlorophenyl ring Amyl ketone 60g, yield 80%.

[0090] Step 2: According to the reported method (Bioorganic & Medicinal Chemistry 2013, 12, 5098), 20 g (96 mmol) of compo...

Embodiment 2

[0098] Embodiment 2: the synthesis of compound I5

[0099] Compound G (170mg, 0.5mmol) was dissolved in 3mL dry THF, dry triethylamine (0.28mL, 2mmol) was added, and then benzoyl chloride (117uL, 1mmol) was added under ice-bath conditions, and then slowly Rise to room temperature, stir overnight, then add sodium bicarbonate solution, extract with EA, spin the solvent and dry in vacuo, pass through a silica gel column to obtain compound H 4 N-Boc-(2R,6R)-6-benzoyloxydesmethylketamine 184mg, yield 85%. 1 H NMR (400MHz, CDCl 3 ): δ8.22-8.19(m, 2H), 7.91(m, 1H), 7.69-7.64(m, 1H), 7.56-7.45(m, 4H), 6.75(br, 1H), 5.54-5.50(m ,1H), 4.00(m,1H), 2.54-2.52(m,1H), 2.14-1.93(m,3H), 1.86(m,1H), 1.41(m,9H). 13 C NMR (100MHz, CDCl 3 ): δ202.2, 164.9, 153.3, 133.2, 131.4, 131.1, 129.9, 129.7, 129.5, 128.3, 128.0, 126.1, 79.2, 73.8, 67.2, 36.6, 34.8, 28.2, 19.0

[0100] Compound H 4 (180 mg) was dissolved in 3 mL of dry THF, gaseous HCl was introduced to saturation at room temperature a...

Embodiment 3

[0103] Embodiment 3: the synthesis of compound C and D

[0104]

[0105] Compounds C and D were prepared by the following preparation methods.

[0106]

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Abstract

The invention relates to application of a long-acting low-addiction compound in preparation of medicine, in particular to application of the compound in medicine for treating or preventing depression,anesthesia and analgesia and improving cognitive function, lung protection, amyotrophic lateral sclerosis or complex regional pain syndrome. The compound is of a structure as shown in a formula I, and can treat depression, particularly bipolar depression and major depressive disorder. Compared with existing known HNK compounds, the compound has longer drug effect time, and basically does not generate addiction.

Description

technical field [0001] The invention relates to the field of medicine, in particular to the application of a long-acting low-addiction compound in the treatment or prevention of depression, including complex regional pain syndrome (CRPS) and other diseases. Background technique [0002] Ketamine is a representative of phencyclidine intravenous anesthesia commonly used in clinical practice, and it is one of the anesthetics with rapid development in clinical and basic research in recent years. In clinical practice, it is often used to meet the anesthesia needs of pediatrics, obstetrics, perioperative period and patients with special diseases because of its characteristics of rapid induction, short action time, quick recovery, and less impact on the respiratory and circulatory systems. [0003] Ketamine was first synthesized in 1962, used in humans in 1965, and officially approved by the FDA for clinical use in 1970. Its typical "separated anesthesia" and short-acting exact an...

Claims

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Application Information

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IPC IPC(8): A61K31/245A61P25/22A61P25/24A61P25/00A61P25/28A61P25/16
CPCA61K31/245A61P25/22A61P25/24A61P25/00A61P25/28A61P25/16
Inventor 李书鹏周强
Owner SHENZHEN RUIJIAN BIOSCI TECH LTD
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