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Pain-easing active compound and medical application thereof

A compound and toxicity technology, applied in the field of analgesic active compounds and their medicinal uses, can solve the problems of poor analgesic effect and short duration of action

Inactive Publication Date: 2018-07-17
TEIZHOU HUAYUAN MEDICINAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the oral analgesic effect of dezocine is poor, so it must be administered by injection; and the action time is short, so it needs to be injected intramuscularly every 3 to 6 hours or intravenously every 2 to 4 hours to maintain the analgesic effect

Method used

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  • Pain-easing active compound and medical application thereof
  • Pain-easing active compound and medical application thereof
  • Pain-easing active compound and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Preparation of O-propionyloxymethyl-dezocine (Ia-1)

[0025]

[0026] 1.1 Preparation of N-benzyloxycarbonyl zocine (i)

[0027] In a mixed solvent of 200ml of dioxane and 200ml of water, add 37.8g of dezocine and 12.3g of sodium hydroxide; add 24ml of benzyloxycarbonyl chloride dropwise while stirring. After the addition, stir overnight; then add 200ml of water, and extract twice with 500ml of diethyl ether; combine the diethyl ether extracts, dry with anhydrous sodium sulfate overnight, filter, and evaporate the filtrate to dryness under reduced pressure to obtain 56.2g of i, which is directly used in the following step response. Proton NMR spectrum: 1 H-NMR (400MHz, CDCl 3 ): 8.1(s, 1H); 7.5-7.3(m, 5H); 6.83(d, 1H); 6.78(d, 2H); 6.71(s, 2H); 6.45(m, 1H); 1H); 5.08(s, 2H); 3.67(d, 1H); 2.92(dd, 1H); 2.69(dd, 1H); 2.24(m, 1H); 1.59(m, 1H); ); 1.45(s, 3H); 1.34(m, 1H); 1.34(m, 1H); 1.31(m, 1H); 1.30(m, 1H); ;1.21(m,1H);1.28(m,1H).

[0028] 1.2 Prepar...

Embodiment 2

[0032] Example 2 Preparation of O-isobutyryloxymethyl-dezocine (Ia-2)

[0033]

[0034] 2.1 Preparation of N-benzyloxycarbonyl-O-isobutyryloxymethyl-dezocine (ii-2)

[0035] Referring to the method of Example 1.2, iodomethyl isobutyrate was used instead of iodomethyl propionate to react with i, and the reaction product was subjected to silica gel column chromatography to obtain ii-2 with a yield of 71%. Proton NMR spectrum: 1 H-NMR (400MHz, CDCl 3 ): 8.05(s, 1H); 7.49-7.40(m, 5H); 6.84(d, 1H); 6.79(d, 2H); 6.75(s, 2H); 6.46(m, 1H); 2H); 3.69(d, 1H); 2.95(dd, 1H); 2.72-2.68(m, 3H); 2.26(m, 1H); 1.62(m, 1H); 1.51(m, 1H); 1.46(s , 3H); 1.34-1.30 (m, 4H); 1.28-1.22 (m, 4H); 1.13 (d, 6H).

[0036] 2.2 Preparation of O-isobutyryloxymethyl-dezocine (Ia-2)

[0037] Referring to the method of Example 1.3, ii-2 was debenzylated by catalytic hydrogenation, and the reaction product was subjected to silica gel column chromatography to obtain Ia-2 with a yield of 28%. Proton NMR sp...

Embodiment 3

[0038] Example 3 Preparation of O-pivaloyloxymethyl-dezocine (Ia-3)

[0039]

[0040] 3.1 Preparation of N-benzyloxycarbonyl-O-pivaloyloxymethyl-dezocine (ii-3)

[0041] Referring to the method of Example 1.2, iodomethyl pivalate was used instead of iodomethyl propionate to react with i, and the reaction product was subjected to silica gel column chromatography to obtain ii-3 with a yield of 62%. Proton NMR: Proton NMR: 1 H-NMR (400MHz, CDCl 3): 8.05(s, 1H); 7.49-7.40(m, 5H); 6.84(d, 1H); 6.79(d, 2H); 6.75(s, 2H); 6.46(m, 1H); 2H); 3.69(d, 1H); 2.95(dd, 1H); 2.72-2.68(m, 2H); 2.26(m, 1H); 1.62(m, 1H); 1.51(m, 1H); 1.46(s , 3H); 1.34-1.30 (m, 4H); 1.28-1.22 (m, 4H), 1.26 (s, 9H).

[0042] 3.2 Preparation of O-pivaloyloxymethyl-dezocine (Ia-3)

[0043] Referring to the method of Example 1.3, ii-3 was debenzylated by catalytic hydrogenation, and the reaction product was subjected to silica gel column chromatography to obtain Ia-3 with a yield of 25%. Proton NMR spectrum:...

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Abstract

The invention relates to dezocine derivatives shown in a formula I and non-toxic and pharmacologically acceptable salts thereof. The structural formula is as shown in the description. In the formula,n is 0 or 1, R represents C1-C8 alkyl or naphthenic base, and R1 represents H or C1-C3 alkyl.

Description

technical field [0001] The present invention relates to orally effective dezocine derivatives and their non-toxic pharmaceutically acceptable salts, their preparation methods and their use in the preparation of analgesics. Background technique [0002] Dezocine is an analgesic with unique pharmacological properties. It has the advantages of good analgesic effect, high safety, wide application range, less adverse reactions, and less addiction. It is widely used in clinical anesthesia induction and maintenance, regional anesthesia, etc. Adjuvant, preemptive analgesia, postoperative intravenous analgesia, cancer analgesia. However, the oral analgesic effect of dezocine is poor, so it must be administered by injection; and the action time is short, so it needs to be injected intramuscularly every 3 to 6 hours or intravenously every 2 to 4 hours to maintain the analgesic effect. Contents of the invention [0003] The object of the present invention is to provide oral effective...

Claims

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Application Information

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IPC IPC(8): C07C217/74A61K31/222A61K31/215A61K31/265A61P29/00
CPCC07C217/74
Inventor 仲伯华王建明靳雪峰
Owner TEIZHOU HUAYUAN MEDICINAL TECH CO LTD
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