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Derivative of aza-aryl compound

A nitrogen-heteroaryl compound technology, applied in the field of nitrogen-containing heteroaryl compound derivatives, can solve the problems of affecting drug efficacy and low solubility, and achieve the effects of increased solubility, good stability, and improved stability

Inactive Publication Date: 2014-04-02
LIAONING YILING KECHUANG BIOLOGICAL MEDICAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above-mentioned FG-4592 is a nitrogen-containing heteroaryl compound with the structure shown in formula I, and its solubility in water is not high, which affects the exertion of the drug effect in the body

Method used

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  • Derivative of aza-aryl compound
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  • Derivative of aza-aryl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 Preparation of hydrochloric acid addition salt of [(4-hydroxyl-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)amino]-acetic acid (formula Ⅰ)

[0057] 1 g of [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)amino]-acetic acid was dissolved in 10 mL of dichloromethane and stirred at room temperature. 0.11 g of hydrochloric acid was added dropwise to the reaction solution. After stirring the reaction solution at room temperature for 1 h, the reaction solution was evaporated to dryness, washed with n-hexane and dried in vacuo. Thus, 0.98 g of white solid was obtained, yield 89.3%. ESI-MS (M+H, 354.5), elemental analysis: C 58.69%, H 4.41%, N 7.21%, O2 0.58%, Cl 9.12%.

[0058] 1 H-NMR (DMSO) δ: 3.14 (s, 3H), 3.60 (d, 2H), 5.35 (s, -OH), 7.25 (s, 1H), 7.29 (s, 1H), 7.14 (s, 2H) , 7.41 (s, 2H), 7.17 (s, 1H), 8.03 (t, 1H), 8.09 (s, 1H).

[0059] The preparation method of the acid addition salt of FG-4592 combined with sulfuric acid, benzenesulfonic acid, nit...

Embodiment 2

[0062] Example 2 Preparation of [(4-hydroxyl-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)amino]-acetic acid (formula Ⅰ) sodium salt

[0063] Dissolve 1 g of [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl) amino]-acetic acid in 10 mL of dichloromethane, add 1.1 equivalents of 10% aqueous sodium hydroxide to in the reaction solution. After stirring the reaction solution at room temperature for 1 h, the dichloromethane reaction solution was evaporated to dryness, washed with n-hexane and dried in vacuo. Obtained 0.99 g of white solid, yield 92.8%. ESI-MS (M-H, 352.5), elemental analysis: C 60.96%, H 4.04%, N 7.48%, Na 6.14%, O 21.37%.

[0064] 1 H-NMR (DMSO) δ: 3.14 (s, 3H), 4.21 (d, 2H), 5.35 (s, -OH), 7.25 (s, 1H), 7.29 (s, 1H), 7.14 (s, 2H) , 7.41 (s, 2H), 7.17 (s, 1H), 8.03 (t, 1H), 8.09 (s, 1H).

[0065] [(4-Hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)amino]-acetic acid and magnesium hydroxide, calcium hydroxide, lithium hydroxide, potassium hydroxide to...

Embodiment 3

[0066] Example 3 Preparation of [(4-hydroxyl-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)amino]-ammonium salt of acetic acid (formula Ⅰ)

[0067] Add 1 g of [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)amino]-acetic acid into dichloromethane and stir at room temperature, fill with ammonia gas, react for 3 hours, and prepare a thin layer Detection, after the reaction was completed, evaporated to dryness to obtain 0.948 g of white solid, yield 90.5%. ESI-MS (M-H, 352.5); elemental analysis: C 61.78%, H 5.18%, N 11.38%, O21.66%;

[0068] 1 H-NMR (DMSO) δ: 2.86 (s, 3H), 3.14 (s, 3H), 3.37-4.0 (t, 4H), 3.56 (d, 1H), 3.58 (s, -OH), 3.85 (d, 2H), 5.35 (s, -OH), 7.25 (s, 1H), 7.29 (s, 1H), 7.14 (s, 2H), 7.41 (s, 2H), 7.0 (d, 2H), 7.17 (s, 1H), 7.16 (s, 4H), 8.03 (t, 1H), 8.09 (s, 1H).

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Abstract

The invention relates to a derivative of an aza-aryl compound as shown in the formula I, and the derivative is capable of adjusting erythropoietin (EPO). The derivative comprises the sodium salt, meglumine salt, hydrobromic acid and hydrochloride of the aza-aryl compound as shown in the formula I, and is high in solubility and water stability in an aqueous medium. In addition, the inventor discovers that the derivative is effective for treating cancers and related anemia.

Description

technical field [0001] The present invention relates to nitrogen-containing heteroaryl compound derivatives for regulating or enhancing erythrogenesis and iron metabolism, treating or preventing iron deficiency and chronic disease and cancer-related anemia. Background technique [0002] Anemia generally refers to any abnormality in hemoglobin or red blood cells that results in a decreased level of oxygen in the blood. Anemia can also occur in association with chronic diseases such as chronic infection, neoplastic disease, chronic inflammation including lesions followed by inflammatory suppression of the bone marrow. Anemia of chronic disease is one of the most common syndromes in medicine. Anemia of chronic disease is usually associated with iron deficiency, and ACD can occur due to insufficient iron availability or insufficient iron throughout the body but defective hemoglobin production. A number of physiological defects have been observed in patients with anemia of chro...

Claims

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Application Information

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IPC IPC(8): C07D217/26A61K31/472A61P7/06
CPCC07D217/26
Inventor 关屹闫冬
Owner LIAONING YILING KECHUANG BIOLOGICAL MEDICAL TECH
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