Pyrrolidine compounds, salts thereof, applications of compounds or salts thereof in nuclear magnetic probes and medicines, reagent, and medicine

The technology of a compound, benzamidomethylpyrrolidine, is applied in the fields of pyrrolidine compounds, salts, nuclear magnetic probes and pharmaceutical applications, reagents, and drugs, and can solve problems such as the inability to accurately detect the distribution density of dopamine

Active Publication Date: 2017-02-01
BEIJING NEUROSURGICAL INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in prior art prevention techniques, dopamine D cannot be accurately detected 2 distribution density of receptors

Method used

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  • Pyrrolidine compounds, salts thereof, applications of compounds or salts thereof in nuclear magnetic probes and medicines, reagent, and medicine
  • Pyrrolidine compounds, salts thereof, applications of compounds or salts thereof in nuclear magnetic probes and medicines, reagent, and medicine
  • Pyrrolidine compounds, salts thereof, applications of compounds or salts thereof in nuclear magnetic probes and medicines, reagent, and medicine

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0089] Preparation example 1. Synthesis of O-benzyl-3-butyn-1-ol

[0090]

[0091] Dissolve and suspend 1.76g of 60% NaH (reagent concentration: 60%) in 40ml of anhydrous DMF (dimethylformamide), add 2.8g of 3-butyn-1-ol under the protection of argon in the ice water external bath , continue to react for 30 minutes after no gas is produced, drop 5.24ml of benzyl bromide, remove the ice-water bath after dropping, and react at room temperature for 12 hours, after stopping the reaction, add 200ml of 1mol / L hydrochloric acid aqueous solution, add EtOAc (ethyl acetate) 100ml to extract 3 times, the organic layer was washed 3 times with 1mol / L hydrochloric acid aqueous solution and saturated NaCl solution, and then washed with Na 2 SO 4 After drying and filtering, the filtrate was evaporated to dryness, and the fraction at 80°C under a pressure of 4 mmHg was collected by vacuum distillation to obtain 3.407 g of a colorless oily product with a yield of 53.2%.

[0092] Product an...

preparation example 2

[0093] Preparation example 2. Synthesis of O-benzyl-4-pentyn-1-ol

[0094]

[0095] Dissolve and suspend 1.76g of 60% NaH in 40ml of anhydrous DMF, add 3.36g of 3-pentyn-1-ol under the protection of argon in an external bath of ice water, continue to react for 30 minutes after no gas is generated, and then add 5.24ml of bromine Benzyl, remove the ice-water bath after dropping, react at room temperature for 12 hours, add 1mol / L hydrochloric acid aqueous solution 200ml after stopping the reaction, add EtOAc 100ml to extract 3 times, the organic layer is washed 3 times with 1mol / L hydrochloric acid aqueous solution and saturated NaCl solution, and NaCl solution 2 SO 4 After drying and filtering, the filtrate was evaporated to dryness, and the fraction at 95°C under a pressure of 4 mmHg was collected by vacuum distillation to obtain 3.967 g of a colorless oily product with a yield of 57%.

[0096] Product analysis: 1 H NMR (400MHz, CDCl 3 )δ7.31(m,5H),4.47(s,2H),3.43(t,J=4.7...

preparation example 3

[0097] Preparation example 3. Synthesis of O-benzyl-5-hexyn-1-ol

[0098]

[0099] Dissolve and suspend 0.876g 60% NaH in 20ml of anhydrous DMF, add 1.95g of 3-hexyn-1-ol under the protection of argon in an external bath of ice water, continue to react for 30 minutes after no gas is generated, and then add 2.6ml of bromine Benzyl, remove the ice-water bath after dropping, and react at room temperature for 12 hours. After stopping the reaction, add 100ml of 1mol / L hydrochloric acid aqueous solution, add 50ml of EtOAc to extract 3 times, and the organic layer is washed 3 times with 1mol / L hydrochloric acid aqueous solution and saturated NaCl solution. 2 SO 4 After drying and filtering, the filtrate was evaporated to dryness, and the fraction at 110° C. under a pressure of 4 mmHg was collected by vacuum distillation to obtain 3.016 g of a colorless oily product with a yield of 80.6%.

[0100] Product analysis: 1 H NMR (400MHz, CDCl 3 )δ7.33(m,5H),4.42(s,2H),3.54(t,J=4.6Hz,2...

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Abstract

The invention provides pyrrolidine compounds, salts thereof, applications of the compounds or the salts thereof in nuclear magnetic probes and medicines, a reagent, and a medicine. The benzamide methylpyrrolidine compounds have a chemical structure represented by general formula (I); and in the formula (I), R<1> is selected from a methyl group, an ethyl group, a methoxy group, an ethoxy group and halogen, R<2> is selected from a methyl group, an ethyl group, a methoxy group, an ethoxy group and halogen, R<3> is selected from C1-5 alkyl groups and H, X<1> is selected from C1-10 alkylene groups or is deleted, X<2> is selected from -(CH2CH2O)n- (n is 1-5) or is deleted, X<3> is selected from C1-5 alkyl groups, X<4> is selected from oxygen, sulfur and a methylene group, and Ln is selected from Gd and Eu. The compounds have a gadolinium and europium chelating structure formed by combining with a dopamine D2 receptor and depending on intramolecular chelating groups, and specifically enhance the contrast of dopamine D2 receptor expression tissues on images in magnetic resonance imaging.

Description

technical field [0001] The invention relates to benzamidomethylpyrrolidine compounds, pharmaceutically acceptable salts thereof, applications in nuclear magnetic resonance relaxation rate detection, nuclear magnetic resonance imaging detection, pituitary adenoma detection, nuclear magnetic resonance relaxation rate detection, nuclear magnetic resonance Resonance imaging detection, pituitary adenoma detection reagents, application of the above salts in reagents for diagnosing dopamine D2 receptors, preparation of drugs for treating diseases related to the expression of dopamine D2 receptors, reagents for diagnosing dopamine D2 receptors, and drugs for the treatment of diseases associated with expression of dopamine D2 receptors. Background technique [0002] Dopamine (English name is dopamine, hereinafter referred to as DA) is the most important catecholamine neurotransmitter in the central nervous system, and plays a very important role in both the central and peripheral ner...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12A61K31/4192A61K49/10A61P35/00G01N24/08
CPCA61K49/106C07D403/12G01N24/088A61K31/4192A61K49/10A61P35/00G01N24/08
Inventor 刘潜张亚卓杨潇骁
Owner BEIJING NEUROSURGICAL INST
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