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Anti-thrombus N-butyl-2,2-dimethyl-4-oxy-tetrahydroimidazopyridoindole and its synthesis and application

A technology of tetrahydroimidazole and dimethyl, which is used in medical preparations containing active ingredients, blood diseases, drug combinations, etc., can solve the problems of low bioavailability, affecting treatment and use effects, and poor solubility.

Inactive Publication Date: 2008-06-04
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the solubility of 1,2,3,4-tetrahydro-β-carboline-3-S-carboxylic acid in polar solvents and non-polar solvents is not very good, resulting in low bioavailability, which in turn affects Treatment and use effect

Method used

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  • Anti-thrombus N-butyl-2,2-dimethyl-4-oxy-tetrahydroimidazopyridoindole and its synthesis and application
  • Anti-thrombus N-butyl-2,2-dimethyl-4-oxy-tetrahydroimidazopyridoindole and its synthesis and application
  • Anti-thrombus N-butyl-2,2-dimethyl-4-oxy-tetrahydroimidazopyridoindole and its synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 1-(1'-Carboxy-2'-methyl)butyl-2,2-dimethyl-4-oxo-tetrahydroimidazo[1',2':1,5]pyrido Preparation of [3,4-b]indole (2a)

[0051] 1) Preparation of S-carboline carboxylic acid

[0052] 400ml of water was placed in a 500ml round bottom flask, and 0.2ml of concentrated sulfuric acid was slowly added. 5.0 g (24.5 mmol) of L-tryptophan was added to the obtained dilute aqueous sulfuric acid solution and sonicated until the L-tryptophan was completely dissolved. To the resulting solution was added 10 ml of 35% formaldehyde solution. The reaction mixture was stirred at room temperature for 6 hours, and the disappearance of L-tryptophan was monitored by thin layer chromatography to terminate the reaction. Concentrated ammonia water was slowly added dropwise to the reaction solution, the pH of the reaction mixture was adjusted to 6, and it was allowed to stand for half an hour. The resulting precipitate filtered out under reduced pressure was washed with water, the co...

Embodiment 2

[0061] Example 2 N-(1'-Carboxy-2'-methyl)propyl-2,2-dimethyl-4-oxo-tetrahydroimidazo[1',2':1,5]pyrido Preparation of [3,4-b]indole (2b)

[0062] 1) Preparation of N-Boc-S-carbolineyl-L-valine methyl ester

[0063] According to the operation of preparing N-Boc-S-carbolineyl-L-isoleucine methyl ester in Example 1, 2.65 g (97.5%) target was obtained from 2.00 g (6.33 mmol) L-valine methyl ester hydrochloride The compound is a colorless solid. Mp 138-140°C; ESI / MS 430 [M+H] + .IR(KBr): 3443, 3202, 3001, 2951, 2845, 1729, 1648, 1602, 1450, 1392, 1370, 1067, 902cm -1 ; 1 H NMR (BHSC-500, DMSO-d 6 ): δ=10.043(s, 1H), 7.962(s, 1H), 7.295(t, J=7.4Hz, 1H), 7.211(t, J=7.7Hz, 1H), 7.004(d, J=7.7Hz) , 1H), 6.892 (d, J=7.4Hz, 1H), 4.840 (t, J=5.4Hz, 1H), 4.423 (d, J=5.4Hz, 1H), 4.225 (dd, J=10.2Hz, J =4.5Hz, 1H), 4.037(dd, J=10.2Hz, J=3.7Hz, 1H), 3.626(s, 3H), 3.103(m, J=5.4Hz, 1H), 2.951(d, J=6.7 Hz, 2H), 1.474 (s, 9H), 1.053 (d, J=5.4Hz, 6H). Elemental Analysis C 23 H 31 N 3 O ...

Embodiment 3

[0068] Example 3 1-(1'-Carboxy-3'-methyl)butyl-2,2-dimethyl-4-oxo-tetrahydroimidazo[1',2':1,5]pyrido Preparation of [3,4-b]indole (2c)

[0069] 1) Preparation of N-Boc-S-carbolineyl-L-leucine methyl ester

[0070] According to the operation of preparing N-Boc-S-carbolineyl-L-isoleucine methyl ester in Example 1, 2.78 g (99.2%) target was obtained from 1.20 g (6.61 mmol) L-leucine methyl ester hydrochloride The compound is a colorless solid. IR(KBr): 3443, 3205, 3002, 2954, 2845, 1724, 1642, 1605, 1455, 1392, 1370, 1065, 903cm -1 ;ESI + -MS(m / e)444[M+H] + ; 1H NMR (BHSC-500, DMSO-d 6 ): δ=10.043(s, 1H), 7.962(s, 1H), 7.291(t, J=7.4Hz, 1H), 7.212(t, J=7.4Hz, 1H), 7.004(d, J=7.4Hz) , 1H), 6.891 (d, J=7.4Hz, 1H), 4.840 (t, J=5.4Hz, 1H), 4.422 (d, J=5.4Hz, 1H), 4.224 (dd, J=10.2Hz, J =4.5Hz, 1H), 4.036(dd, J=10.2Hz, J=3.7Hz, 1H), 3.625(s, 3H), 2.950(d, J=6.7Hz, 2H), 1.877(d, J=6.0 Hz, 2H), 1.473 (s, 9H), 1.852 (m, J=5.4Hz, 1H), 1.055 (d, J=5.4Hz, 6H). Elemental Analysis C ...

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Abstract

The invention discloses compounds of the general formula I and provides a preparation method of the compounds which have good antithrombotic activity, wherein, R represents CH (CH3) CH 2CH3, CH (CH3)2, CH2CH (CH3)2 , CH3, H, CH2C6H5, CH2C6H4-OH-p, indole-5-group-CH2, imidazole-4-group-CH2-, CH2CH2SCH3, CH2COCH3, CH2CH2CO2CH3, CH2CH2CO2H, CH2OH, CH (OH)CH3, CH2CH2CH2NHC(NH) NH2, CH2CONH2, CH2CH2CONH2, CH2SH, CH2CH2CH2CH2NHCBz or CH2CH2CH2CH2NH2.

Description

technical field [0001] The present invention relates to N-(1'-substituted carboxyethyl-1'-yl)butyl-2,2-dimethyl-4-oxo-tetrahydroimidazo[1',2' with antithrombotic activity: 1,5]pyrido[3,4-b]indole, its synthesis and application. Background technique [0002] Vascular embolism is most responsible for the high mortality rate of cardiovascular and cerebrovascular diseases. Thrombosis is the most important etiology of vascular embolism disease. Finding antithrombotic drugs is one of the hot spots in new drug research. [0003] There are usually three reasons for thrombus formation: first, the blood lipid block on the blood vessel wall falls off and flows into the blood; second, the aggregation ability of platelets is too strong, and there are small pieces of platelets in the blood; Solubility decreased. Among them, the second reason is an important reason leading to thrombosis, so it is very important to seek anti-platelet aggregation drugs. Aspirin is a common antiplatelet ...

Claims

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Application Information

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IPC IPC(8): C07D471/14A61K31/437A61P7/02C07D209/00C07D211/00C07D233/00
CPCY02P20/55
Inventor 彭师奇赵明王超刘佳望
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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