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Proline derivative and application of proline derivative in preparation of medicine for treatment of cardiovascular and cerebrovascular diseases

A technology of proline and derivatives, applied in the field of medicine, can solve the problems of low bioavailability, short half-life of stachydine, poor anti-ischemic stroke activity, etc., and achieve the effect of inhibiting cytotoxicity

Active Publication Date: 2019-10-22
青岛海生洋润生物科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Animal studies have shown that stachydrine and motherwort both exhibit anti-ischemic stroke activity in animal model groups, but stachydrine has a short half-life and poor anti-ischemic stroke activity in vivo
Leonurine is prone to glucuronidation in vivo, and its bioavailability is low.

Method used

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  • Proline derivative and application of proline derivative in preparation of medicine for treatment of cardiovascular and cerebrovascular diseases
  • Proline derivative and application of proline derivative in preparation of medicine for treatment of cardiovascular and cerebrovascular diseases
  • Proline derivative and application of proline derivative in preparation of medicine for treatment of cardiovascular and cerebrovascular diseases

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: The synthetic route of N-methyl-L-proline b is as follows:

[0049]

[0050] Dissolve L-proline (4.0g, 34.8mmol) in methanol (40mL), add 40% formaldehyde aqueous solution (2.8mL, 38.2mmol) and 10% palladium carbon (1g) successively, add hydrogen, and add hydrogen at room temperature Reacted for 24 hours. After the reaction was complete, it was filtered and the mother liquor was concentrated to dryness to obtain 4 g of white solid with a yield of 89%, which was N-methyl-L-proline (compound b). ESI-MS: (m / z, %)=130[M+H] + .

Embodiment 2

[0051] Embodiment 2: The synthetic route of compound B-4 is as follows:

[0052]

[0053] The N-methyl-L-proline b (1.29g, 10mmol) was added into dichloromethane (20mL), DCC (2.47g, 12mmol) and glycine (0.75g, 10mmol) were added successively, and reacted at room temperature for 24 hours, filtered, and the mother liquor was concentrated to obtain 1 g of white solid with a yield of 54%, namely compound B-4. 1 H NMR (500MHz, CD 3 OD)δ=4.14(t,J=8.3,1H),4.00(s,2H),3.71(ddd,J=11.4,7.7,4.1,1H),3.22(d,J=11.1,1H),2.95( d, J = 10.5, 3H), 2.58 (dd, J = 12.2, 7.5, 1H), 2.24-2.02 (m, 3H).

Embodiment 3

[0054] Embodiment 3: The synthetic route of compound B-5 is as follows:

[0055]

[0056] The B-4 (1.86g, 10mmol) was added into dichloromethane (20mL), followed by DCC (2.47g, 12mmol) and Y5 (3.1g, 10mmol), reacted at room temperature for 24 hours, filtered, and the mother liquor was concentrated to 1.4 g of colored oily substance, the yield is 30%, which is compound B-5. ESI-MS: (m / z, %)=480[M+H] + . 1 H NMR (500MHz,D 2 O) δ=7.43(s, 2H), 4.49(d, J=7.8Hz, 2H), 4.42(t, J=6.5Hz, 2H), 4.31(t, J=8.5Hz, 1H), 3.92(s ,6H),3.85-3.80(m,1H),3.31-3.25(m,3H),2.99(s,3H),2.68-2.61(m,1H),2.32–2.04(m,3H),1.94-1.84 (m,2H), 1.80–1.73(m,2H).

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Abstract

The invention provides a proline derivative, a preparation method and application of the proline derivative in preparation of medicine for treatment of cardiovascular and cerebrovascular diseases. Theproline derivative has the structure of a general formula (I); and it is proved through pharmacology experiments that the proline derivative has an obvious nerve protection function and can be used for preparing the medicine for treatment of the cardiovascular and cerebrovascular diseases, especially for preparing the medicine for anti-ischemic stroke.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a proline derivative, a preparation method thereof and an application in preparation of medicines for treating cardiovascular and cerebrovascular diseases. Background technique [0002] Stroke is a refractory disease that seriously endangers the safety of human life and is characterized by high morbidity, disability and mortality. In the ranking of the causes of death published by the Ministry of Health of my country in 2008, stroke is the third leading cause of death in urban areas and the second leading cause of death in rural areas. Epidemiological surveys show that the incidence of stroke in young people has been increasing in recent years. The proportion of stroke in adults under the age of 45 is 5% and 13.44% in Western countries and domestic reports, respectively. Stroke is divided into ischemic stroke and hemorrhagic stroke according to its nature, and ische...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/16A61P9/10A61P25/00A61P9/00
CPCC07D207/16A61P9/10A61P25/00A61P9/00A61K31/401
Inventor 李文保李峰张良侯晨辉管华诗
Owner 青岛海生洋润生物科技有限公司
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