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Derivative of alpha-amino phosphonic acid containing saccharide groups, preparation method and medical application thereof

A technology of methyl amino group and methyl methyl phosphonic acid monoethyl ester, which is applied in the field of glycosyl-containing α-amino phosphonic acid derivatives, its preparation and its medical application, and can solve the lack of prevention and/or prevention of autoimmune diseases or treatment, immunocompromised, Cushing's syndrome, etc.

Inactive Publication Date: 2014-03-12
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the long-term application of hormone drugs and immunosuppressive drugs can easily lead to low immune function, such as Cushing's syndrome, and even serious side effects such as infection and tumor
Therefore, autoimmune diseases currently lack effective means of prevention and / or treatment

Method used

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  • Derivative of alpha-amino phosphonic acid containing saccharide groups, preparation method and medical application thereof
  • Derivative of alpha-amino phosphonic acid containing saccharide groups, preparation method and medical application thereof
  • Derivative of alpha-amino phosphonic acid containing saccharide groups, preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] Example 1: Preparation of α-[N-(D-glucosyl)-N-methylamino]-α-(2,4-dihydroxyphenyl)methylphosphonic acid monoethyl ester-compound 1

[0090] Weigh 7.00g (0.0507mol) 2,4-dihydroxybenzaldehyde, 9.80g (0.0502mol) N-methyl-D-glucosamine and 7.80g (0.0565mol) diethyl phosphite, add 60ml absolute ethanol Dissolve, stir and react at a bath temperature of about 65°C for 5 days, cool, concentrate under reduced pressure, add ethyl acetate, a yellow solid precipitates, collect the solid by filtration, wash with ethyl acetate, dry to obtain 20.20g, yield 94.6%, mp 190 -193°C (dec.).

[0091] 1 H-NMR (D 2 O, ppm) δ: 0.969(t, J=7.00Hz, 3H), 2.136(d, J=8.82Hz, 2H), 2.538(s, 3H), 2.90-3.10(m, 2H), 3.40-4.00( m, 11H), 4.42-4.48 (br-s, 1H), 6.204 (d, J=2.24Hz, 1H), 6.267 (dd, J 1 =8.40Hz,J 2 = 2.24Hz, 1H), 6.956 (d, J = 8.40Hz, 1H).

Embodiment 2

[0092] Example 2: Preparation of α-[N-(D-glucosyl)-N-methylamino]-α-(2,3-dihydroxyphenyl)methylphosphonic acid monoethyl ester-compound 2

[0093] According to the method of Example 1, 2,3-dihydroxybenzaldehyde was used instead of 2,4-dihydroxybenzaldehyde to prepare it, with a yield of 76.0%, mp 170-173°C (dec.).

[0094] 1 H-NMR (D 2 O, ppm) δ: 9.49(t, J=7.00Hz, 3H), 2.170(d, J=7.92Hz, 2H), 2.525(s, 3H), 2.90-3.10(m, 2H), 3.38-3.96( m, 11H), 4.40-4.47 (br-s, 1H), 6.58-6.78 (m, 3H).

Embodiment 3

[0095] Example 3: Preparation of α-[N-(D-glucosyl)-N-methylamino]-α-(3,4-dihydroxyphenyl)methylphosphonic acid diethyl ester-compound 3

[0096] According to the method of Example 1, 3,4-dihydroxybenzaldehyde is used instead of 2,4-dihydroxybenzaldehyde to prepare the reaction, the yield is 85.4%, mp 196-199°C (dec.).

[0097] 1 H-NMR (D 2 O, ppm) δ: 0.85-1.16 (m, 6H), 2.42-2.67 (m, 5H), 2.82-3.12 (m, 2H), 3.40-4.00 (m, 14H), 6.50-6.90 (m, 3H) .

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Abstract

The invention relates to a derivative of alpha-amino phosphonic acid containing saccharide groups, a preparation method and the medical application thereof, in particular to a compound which is represented by formula I and can adjust the functions of the immune system, a stereoisomer thereof and application of medical composition containing the compound and the stereisomer in preventing or treating autoimmune diseases, such as chronic nephritis, multiple sclerosis, psoriasis, systemic lupus erythematosus, rheumatoid arthritis, insulin-dependent diabetes, chronic and toxic thyroiditis, myasthenia gravis, ankylosing spondylitis, pemphigus and the like as well as organ transplantation and allergic diseases and the like or application as tool medicine for studying diseases related to the function of the immune system and / or the functional disorder of the immune system.

Description

Technical field: [0001] The present invention relates to the preparation of α-aminophosphonic acid with immunomodulatory activity as shown in general formula I, its derivatives, its stereoisomers, its pharmaceutically acceptable salts and its solvates, and its role in the prevention or treatment of immune Autoimmune diseases related to system dysfunction such as chronic nephritis, multiple sclerosis, psoriasis, systemic lupus erythematosus, rheumatoid arthritis, insulin-dependent diabetes mellitus, chronic toxic thyroiditis, myasthenia gravis, ankylosing spondylitis , pemphigus, etc., and the application in organ transplantation and allergic diseases, or as a tool drug for the study of immune system function or diseases related to its dysfunction, and the pharmaceutical composition containing these compounds. Background technique: [0002] Autoimmune disease is a major disease that seriously endangers human health and is a common multiple chronic disease. Chronic nephritis,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H5/06A61K31/7008A61P37/00A61P13/12A61P25/00A61P17/06A61P29/00A61P19/02A61P3/10A61P5/14A61P21/04A61P17/00A61P37/06A61P37/08
Inventor 杨日芳张永祥周文霞肖智勇赵如胜陈少辉恽榴红程军平王艳芳赵利枝
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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