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Adenine bisphosphonate and preparation method thereof and application in pharmaceutical preparations

A bisphosphonate and adenine technology, applied in the field of adenine bisphosphonate and its preparation and application in pharmaceutical preparations, to achieve long-lasting effects

Inactive Publication Date: 2008-04-09
HEBEI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Zoledronate awaits further clinical validation

Method used

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  • Adenine bisphosphonate and preparation method thereof and application in pharmaceutical preparations
  • Adenine bisphosphonate and preparation method thereof and application in pharmaceutical preparations
  • Adenine bisphosphonate and preparation method thereof and application in pharmaceutical preparations

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114] Example 1 Synthesis of compound I of the present invention

[0115] (a) Synthesis of (6-amino-purin-9-yl)-ethyl acetate:

[0116] Put adenine (10.8g, 0.08mol) in a four-neck flask, add 100ml of DMF, heat to 100°C, adenine is insoluble, after cooling down to room temperature, add anhydrous Na 2 CO 3 (8.2g, 0.08mol), reacted at 100°C for 30min, lowered to 80°C, and slowly added ethyl monochloroacetate (17ml, 0.16mol) dropwise. After dropping, keep the temperature at 80° C. and stir the reaction. TLC monitors the reaction process. After 8 hours, after cooling, filter with suction to obtain a dark yellow solid. After drying with an infrared lamp, the total amount of solid is 19 g.

[0117] Purification of (6-amino-purin-9-yl)-ethyl acetate

[0118] Take 8 g of the crude product of (6-amino-purin-9-yl)-ethyl acetate, add 200 ml of ethanol, heat to boiling, and filter while hot to remove alcohol-insoluble matter. Add an appropriate amount of activated carbon to the filtra...

Embodiment 2

[0136] Synthesis of Example 2 Compound II

[0137] (a) Synthesis of 3-(6-amino-purin-9-yl)-propionic acid ethyl ester

[0138]Adenine (10.8g, 0.08mol), absolute ethanol (280ml), and benzene (34ml) were placed in a three-necked flask, heated and distilled, and after collecting about 93ml fractions, metal sodium (80mg) was added. After no bubbles were generated, Slowly add 25.6ml of ethyl acrylate dropwise, after dropping, heat to reflux, monitor the reaction process by TLC, after 10 hours of reaction, distill and concentrate the reaction solution to precipitate a white solid, cool, filter with suction, recrystallize from ethanol, collect the product, weighing 17.7g, Yield 94.1%, melting point 164~166 ℃, literature [8] 167~168℃. 1 H-NMR (solvent CD 3 COOD): δ: 1.189~1.217 (t, J=7, 7, 2”-H), 4.121~4.163 (q, J=7, 7, 7, 1”-H) 3.070~3.095 (t, J= 6.5, 6, 3'-H), 4.636~4.661 (t, J=6.5, 6, 2'-H), 2.096~2.109 (solvent CD3COOD), 5.075 (solvent CD3COOD), 8.415 (s, 8-H) , 8.471 (s, 2-H...

preparation Embodiment 3

[0158] Formulation Example 3 Tablets are prepared according to methods known in the art, and each tablet contains the following ingredients:

[0159] Compound I 50mg

[0160] Lactose 60mg

[0161] Magnesium Stearate 3mg

[0162] Polyvinylpyrrolidone 120mg

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Abstract

The invention discloses a novel adenine bisphosphonate, a preparation method and the application in the preparation of pharmaceutical preparations for the treatment of the metabolic bone diseases. A compound is (2-(6-amino-purine-9-yl)-1-hydroxy-phosphono-ethyl)phosphonate and 3-((6-amino-purine-9-yl)-1-hydroxy-phosphono-propyl)phosphonate. The compound can be used for the treatment of hypercalcemia, bone pains and other metabolic bone diseases caused by osteoporosis, osteitis deformans and bone metastasis of the malignant tumor, and the invention has an anti-cancer effect at the same time.

Description

technical field [0001] The invention relates to a new bisphosphonate, its preparation method and its application in pharmaceutical preparations. Background technique [0002] Bisphosphonates (bisphosphates) drugs are a new class of anti-metabolic bone disease drugs developed in the past 20 years. They are pyrophosphate analogues. Treatment of various bone metabolic diseases such as osteoporosis, osteitis deformans, multiple myeloma (MM), hypercalcemia and bone pain caused by bone metastases of malignant tumors. It is especially suitable for the treatment of osteoporosis characterized by decreased bone mass and destruction of bone structure leading to increased bone fragility and fracture rate. The latest research shows that bisphosphonic acid drugs can also play an anti-tumor role by promoting tumor cell apoptosis, inhibiting the release of tumor growth factors, and affecting tumor cell adhesion, invasion and viability. [0003] At present, there are four kinds of bisphosp...

Claims

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Application Information

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IPC IPC(8): C07F9/6561A61K31/675A61P19/08A61P35/00
Inventor 蒋晔韩彩丽李立更蔡太梅
Owner HEBEI MEDICAL UNIVERSITY
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