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Preparation method and medical use of sulfonamide compounds with glucuronic acid structure

A technology of glucuronic acid and compounds, which is applied in the field of preparation and medical application of sulfonamide compounds with glucuronic acid structure, can solve problems such as eye irritation, unsatisfactory binding ability of carbonic anhydrase, toxic and side effects, etc. The effect of internal pressure

Active Publication Date: 2021-02-05
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Carbonic anhydrase inhibitors are currently one of the main drugs used clinically for glaucoma to lower intraocular pressure, but the first-generation carbonic anhydrase inhibitors have systemic side effects, and the second-generation carbonic anhydrase inhibitors are topical drugs, mostly salt In the form of acid salt, it has a certain stimulating effect on the eyes; in addition, the binding ability with carbonic anhydrase is not ideal, and it needs to be administered every 3-4 hours

Method used

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  • Preparation method and medical use of sulfonamide compounds with glucuronic acid structure
  • Preparation method and medical use of sulfonamide compounds with glucuronic acid structure
  • Preparation method and medical use of sulfonamide compounds with glucuronic acid structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: N-(1'-O-methyl-β-D-glucuronyl)-4-aminophenylsulfonamide (G1)

[0025] At room temperature, dissolve 15.0 g of glucuronolactone 1 in 70 mL of methanol, add 2.4 mL of 1 mol / L sodium methoxide / methanol solution, and react in the dark until all solids disappear, add 0.14 mL of glacial acetic acid to adjust the pH to 7, and reduce Press and concentrate to obtain brown viscous syrup 2.

[0026] Dissolve the above product in 70mL of pyridine, add 70mL of benzoyl chloride dropwise in an ice-water bath, and react for 5 hours. After the solution is clarified, add 200mL of water, continue to stir for 20 minutes, and extract 3 times with dichloromethane. Washed with water, dilute hydrochloric acid and saturated sodium bicarbonate solution, anhydrous Na 2 SO 4 dry. After filtration, dichloromethane was distilled off under reduced pressure to obtain intermediate 3.

[0027] Dissolve the above product in 70mL of dichloromethane, add 70mL of hydrogen bromide acetic acid ...

Embodiment 2

[0031] Example 2: N-(1'-O-methyl-β-D-glucuronyl)-4-amino-1,3,4-thiadiazol-2-yl-sulfonamide (G2)

[0032] The preparation method of the compound in Example 2 is the same as in Example 1, except that 5-amino-1,3,4-thiadiazol-2-yl-sulfonamide is used instead of p-aminobenzenesulfonamide. m.p 200.9–202.6°C; 1 H NMR (600MHz, DMSO-d 6 ) δ8.36(s,2H),5.27(d,J=5.1Hz,1H),5.24(d,J=5.0Hz,1H),4.19(d,J=7.8Hz, 1H),4.12(s, 1H), 4.00(d, J=9.7Hz, 1H), 3.49(t, J=9.3Hz, 1H), 3.40(s, 3H), 3.23 (td, J=9.0, 4.7Hz, 1H), 3.07( td,J=8.5,5.0Hz,1H). 13 C NMR (151MHz, DMSO-d 6 )δ168.88,165.17,161.48,105.08,76.48,76.06,73.37,71.59,56.98,49.12. ESI-MS(m / z):368.8[M-H] – ,393.2[M+Na] + ;HRMS(ESI):Calcd.for[M-H] – C 9 h 13 N 4 o 8 S 2 :369.0253,Found 369.0275[M-H] – .

Embodiment 3

[0033] Example 3: N-(1'-O-ethyl-β-D-glucuronyl)-4-aminophenylsulfonamide (G3)

[0034] The preparation method of the compound of Example 3 is the same as that of Example 1, except that ethanol is used instead of methanol. m.p 231.1–234.2°C; 1 H NMR (600MHz, DMSO-d 6 )δ10.46(s,1H),7.82(s,2H),7.77(d, J=8.9Hz,2H),7.27(s,2H),5.39(s,1H),5.18(s,2H), 4.24(d, J=7.8Hz, 1H), 3.79 (ddd, J=9.8, 8.2, 5.5Hz, 2H), 3.54–3.45(m, 2H), 3.21(t, J=9.0Hz, 1H), 3.06 (t,J=8.4Hz,1H),1.13(d,J=4.5Hz,3H). 13 C NMR (151MHz, DMSO-d 6 )δ168.10, 142.20, 139.11, 127.15, 119.47, 103.71, 77.36, 76.82, 73.56, 71.58, 64.84, 15.66. ESI-MS(m / z): 374.9[M-H] – ,399.2[M+Na] + ;HRMS(ESI):Calcd.for[M-H] – C 14 h 19 N 2 o 8 S:375.0840,Found 375.0884[M-H] – .

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Abstract

The present invention belongs to the technical field of medicine, and provides sulfonamide compounds with glucuronic acid structure having structures shown in general formulas (I) and (II), wherein the definition of R in general formulas (I) and (II) involved As described in the claims and description. The invention also relates to the preparation method of the compounds and their potential application as anti-glaucoma drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a preparation method and medical application of a class of sulfonamide compounds having a glucuronic acid structure, in particular to novel glucuronic acid amido substituted thiadiazolyl sulfonamide compounds and glucuronic acid amido The substituted phenylsulfonamide compound, its preparation method and its inhibitory effect on carbonic anhydrase II have potential applications as anti-glaucoma drugs. Background technique [0002] Carbonic anhydrases (Carbonic anhydrases, CAs) are a class of zinc-containing metalloenzymes ubiquitous in living organisms, which mainly catalyze the reversible hydration reaction of carbon dioxide, and play an important role in physiological processes such as gas exchange, ion exchange, and intracellular pH balance in the body. effect. Among them, carbonic anhydrase II (CA II) is widely distributed and has been found in almost all tissues and cell typ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H7/02C07H1/00A61K31/7012A61K31/7042A61P27/02A61P27/06
CPCC07H1/00C07H7/02
Inventor 刘洋郭春侯状程卯生闫海宁张淼
Owner SHENYANG PHARMA UNIVERSITY
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