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Compound for treating cerebral infarction and preparation method of compound

A compound and alkyl technology, applied in the field of compounds for the treatment of cerebral infarction and the preparation of medicines for the treatment of cerebral infarction, can solve the problems of uncertain curative effect, reperfusion injury, single curative effect, etc.

Inactive Publication Date: 2017-10-13
牡丹江医学院附属红旗医院
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The common characteristics of the above-mentioned drugs for the treatment of cerebral infarction are: strong pertinence, clear target, but single curative effect, can only provide partial protective effect, and the clinical curative effect is relatively small
And there are different degrees of toxic and side effects. For example, it is difficult for thrombolytic drugs to enter the damaged brain tissue through the blood-brain barrier to exert their effects, so the curative effect is uncertain, and there are side effects of causing reperfusion injury and bleeding; vasodilators can make normal The blood vessels in the area dilate, causing the blood in the lesion to flow to the normal brain tissue, resulting in the so-called "stealing blood" phenomenon

Method used

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  • Compound for treating cerebral infarction and preparation method of compound
  • Compound for treating cerebral infarction and preparation method of compound
  • Compound for treating cerebral infarction and preparation method of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] 4-((5-(5-(1H-tetrazol-5-yl)pyrimidin-2-yl)-3-methyl-5,6,7,8-tetrahydro-1,5-naphthalene -2-yl)methyl)morpholine

[0064]

[0065] Step 1: Dissolve morpholine (2.58g, 30mmol) and 60% NaOH (1.40g, 35mmol) in 150mL of anhydrous THF, and stir at 50°C for 30min under nitrogen protection. Cool to room temperature, and slowly add 100 mL of 6-bromomethyl-7-methyl-1,2,3,4-tetrahydro-1,5-naphthalene (6.01g, 25mmol) in anhydrous THF solution dropwise ; Then heated and stirred for 3h, the reaction solution was poured into 150mL ice water, extracted three times with ethyl acetate, combined the organic phases, washed with saturated brine, the organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The obtained residue was subjected to column chromatography (volume ratio of eluent: cyclohexane: ethyl acetate = 6:1), and the solvent was evaporated under reduced pressure to obtain an off-white solid 4-((3-methyl-5,6,7, 8-T...

Embodiment 2

[0072] (2S,6R)-4-((5-(5-(1H-tetrazol-5-yl)pyrimidin-2-yl)-3-trifluoromethyl-5,6,7,8-tetrahydro- 1,5-Naphthalin-2-yl)methyl)-2,6-dimethylmorpholine

[0073]

[0074] According to the method of Example 1, (2S,6R)-2,6-dimethylmorpholine was used instead of morpholine, and 6-bromomethyl-7-trifluoromethyl-1,2,3,4-tetra Hydrogen-1,5-naphthalene is substituted for 6-bromomethyl-7-methyl-1,2,3,4-tetrahydro-1,5-naphthalene, and the total yield of the three steps is 48.7%.

[0075] ESI-MS: 475.21[M+H] +

[0076] Elemental analysis: theoretical value / measured value, C(53.05 / 53.17), H(5.09 / 5.02), F(11.99 / 11.89), N(26.51 / 26.54), O(3.36 / 3.38)

[0077] 1 H NMR(400MHz, CDCl 3 )δ13.09(s,1H),9.06(s,2H),7.35(s,1H),3.94(s,2H),3.51(m,2H),3.08(t,2H),3.02(t,2H ), 2.48 (d, 4H), 1.92 (m, 2H), 1.18 (d, 6H).

Embodiment 3

[0079] 5-(5-(1H-tetrazol-5-yl)pyridin-2-yl)-2-((4-methylsulfonyl-piperazin-1-yl)methyl)-5,6,7, 8-Tetrahydro-1,5-Naphthalazine-4-ol

[0080]

[0081] According to the method of Example 1, using 1-methylsulfonyl-piperazine instead of morpholine, using 2-bromomethyl-5,6,7,8-tetrahydro-1,5-naphthalene-4- Alcohol replaces 6-bromomethyl-7-methyl-1,2,3,4-tetrahydro-1,5-naphthalene, the total yield of the three steps is 45.5%.

[0082] ESI-MS: 472.18[M+H] +

[0083] Elemental analysis: theoretical value / measured value, C(50.94 / 50.82), H(5.34 / 5.42), N(26.73 / 26.64), O(10.18 / 10.27), S(6.80 / 6.85)

[0084] 1 H NMR(400MHz, CDCl 3 )δ13.09(s,1H), 10.04(s,1H), 8.35(d,1H), 7.62(q,1H), 6.74(d,1H), 6.48(s,1H), 3.94(s,2H) ), 3.08 (t, 2H), 3.02 (t, 2H), 2.93 (s, 3H), 2.43 (t, 4H), 2.33 (t, 4H), 1.92 (m, 2H).

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Abstract

The invention relates to a compound for treating cerebral infarction. The invention further relates to a preparation method of the compound and an application of the compound for preparing a drug for treating the cerebral infarction. The compound can significantly reduce thrombosis generated after rat vein ligation, and can obviously reduce an area of the cerebral infarction of a rat with middle cerebral artery occlusion. Therefore, the compound can prevent the thrombosis, can facilitate thrombolysis, and can be used in prevention and treatment of the cerebral infarction such as cerebral thrombosis and cerebral embolism.

Description

Technical field [0001] The present invention belongs to the field of medicinal chemistry, and specifically relates to a class of compounds used for the treatment of cerebral infarction. The present invention also relates to a preparation method of the compound and its use for preparing drugs for the treatment of cerebral infarction. Background technique [0002] Cerebral infarction is also known as ischemic stroke and ischemic stroke. It is caused by various causes of regional blood supply obstacles in the local brain tissue, leading to ischemic and hypoxic lesions and necrosis of brain tissue, which in turn produces clinically corresponding neurological functions Missing performance. Cerebral infarction is divided into cerebral thrombosis, cerebral embolism and lacunar infarction according to the different pathogenesis. Cerebral thrombosis is the most common type of cerebral infarction, accounting for 60% of all cerebral infarctions. [0003] At present, the clinical treatment of...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/5377A61K31/506A61K31/496A61K31/444A61P7/02A61P9/10
CPCC07D471/04
Inventor 罗海龙李欣焦杨徐丹贾茜袁秀梅姜爱英
Owner 牡丹江医学院附属红旗医院
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