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Medication towards target of bone, synthetic method and application

A synthetic method and bone-targeted technology, applied in drug combinations, pharmaceutical formulations, chemical instruments and methods, etc.

Inactive Publication Date: 2007-09-26
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these drugs, from the perspective of their activity, selectivity and side effects, also have many shortcomings.

Method used

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  • Medication towards target of bone, synthetic method and application
  • Medication towards target of bone, synthetic method and application
  • Medication towards target of bone, synthetic method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Raloxifene and bisphosphonic acid complex (9A) synthetic route 1

[0047] Step 1: Preparation of compound (6)

[0048] Method A:

[0049] 124mg (0.2mmol) of compound (4) was dissolved in 30ml of acetone, followed by adding 110mg of potassium carbonate, a small amount of potassium iodide and 345mg of ethyl chloroacetate, stirred at 60-70°C for 3 hours, concentrated, extracted three times with ethyl acetate, washed with water, anhydrous It was dried over sodium sulfate, concentrated by filtration, and subjected to silica gel column chromatography (chloroform / methanol 40:1) to obtain 65 mg of yellow powdery crystals with a yield of 52%.

[0050] Method B:

[0051] Dissolve 112.6 mg (0.2 mmol) of compound (4) in 4 mL of anhydrous THF, add 15 mg (0.35 mmol) of NaH, stir, then add 0.026 mL (0.23 mmol) of ethyl bromoacetate, and react for 1 hour. Concentrate, pour into saturated ammonium chloride solution, extract with appropriate amount of ethyl acetate, and dry over anhyd...

Embodiment 2

[0077] Example 2 Preparation of compound (11B). (preparation method is identical with embodiment 1)

[0078] Step 1: Preparation of compound (9B)

[0079] Using tetraethyl 4-aminobutyl-1,1-bisphosphonate as raw material, a light yellow solid was obtained with a yield of 80%.

[0080] 1 HNMR (400MHz, CDCl 3 )δ 1.3 (12H, br), 1.5 (6H, m), 1.7 (2H, qt, J=7), 1.9 (2H, tq, J=9.6), 2.4 (1H, tt, J=24.3) 2.53 (4H, br), 2.62 (2H, t), 2.79 (2H, t, J=5.6), 4.18 (10H, m), 4.65 (2H, s), 4.99 (2H, s), 6.77 (2H, d , J=9.0), 6.9 (2H, q, J=2.0, J=6.9), 7.00 (1H, dd, J=2.3, J=9.0), 7.08 (1H, d, J=2.0), 7.36 (7H , m), 7.6 (1H, d, J=9.0), 7.74 (2H, q, J=1.8, J=7.0).

[0081] Step 2: Preparation of compound (10B)

[0082] Yield 75%.

[0083] 1 HNMR (600MHz, CDCl 3 )δ1.35 (12H, m), 1.50 (6H, br), 1.71 (2H, m), 1.9 (2H, m), 2.38 (1H, m, J=23.6), 2.6 (2H, t), 2.64 (4H, m), 2.83 (2H, br), 4.2-4.61 (10H, m), 4.61 (2H, s), 6.6 (4H, t, J=9.1), 7.0 (1H, dd, J=2.4, J=8.8), 7.1 (2H, d...

Embodiment 3

[0087] Example 3 Preparation of compound (11C). (preparation method is identical with embodiment 1)

[0088] Step 1: Preparation of compound (9C)

[0089] Using tetraethyl 4-hydroxybutyl-1,1-bisphosphonate as raw material, a light yellow solid was obtained with a yield of 65%.

[0090] 1 HNMR (400MHz, CDCl 3 )δ1.23 (12H, br), 1.5 (6H, m), 1.8 (2H, qt, J=2), 2.1 (2H, tq, J=9), 2.4 (1H, tt, J=23.8) 2.53 (4H, br), 2.79 (2H, t, J=5.6), 3.62 (2H, t), 4.18 (10H, m), 4.65 (2H, s), 4.99 (2H, s), 6.77 (2H, d , J=9.0), 6.9 (2H, q, J=2.0, J=6.9), 7.00 (1H, dd, J=2.3, J=9.0), 7.08 (1H, d, J=2.0), 7.36 (7H , m), 7.6 (1H, d, J=9.0), 7.74 (2H, q, J=1.8, J=7.0).

[0091] Step 2: Preparation of compound (10C)

[0092] A light yellow solid was obtained with a yield of 78%.

[0093] 1 HNMR (600MHz, CDCl 3 )δ1.35 (12H, m), 1.50 (6H, br), 1.8 (2H, m), 2.1 (2H, m), 2.38 (1H, m, J=23.9), 2.64 (4H, m), 2.83 (2H, br), 3.7 (2H, t), 4.2-4.61 (10H, m), 4.61 (2H, s), 6.6 (4H, t, J=9....

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Abstract

A bone-targetable medicine and its synthesizing process are disclosed. It is a biphosphorous acid compound which has the action to suppress bone absorption, better asteotropism and better chelating function, so it can be used to treat relative diseases.

Description

technical field [0001] The invention relates to a bone targeting drug, a synthesis method and application. Furthermore, it is a compound using bisphosphonic acid as a bone-targeting agent developed for the purpose of preventing and treating bone and calcium metabolism diseases such as osteoporosis, hypercalcemia, and Paget's disease. Background technique [0002] With the development of society, the speed of population aging is accelerating. As one of the common diseases of the elderly, osteoporosis and related diseases have gradually become an increasingly prominent social public health problem. Osteoporosis is a systemic skeletal metabolic disease characterized by decreased bone mass and microstructural degeneration of bone tissue leading to metabolic disorders, increased bone fragility and easy fractures. This disease is most common in middle-aged and elderly people, especially postmenopausal women, and increases with age. In my country, 90% of women over 60 suffer from...

Claims

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Application Information

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IPC IPC(8): C07F9/40C07F9/59A61K31/675A61K31/663A61P19/10
Inventor 王军波杨春皓严雪铭吴希罕谢毓元
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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