Vitamin d3 lactam derivative

A technology of derivatives and vitamins, applied in the field of vitamin D3 lactam derivatives or their pharmaceutically acceptable solvates, can solve problems such as accumulation and lack of knowledge

Inactive Publication Date: 2009-07-01
TEIJIN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

That is, it can be said that for vitamin D 3 Chemical structure of derivatives and vita

Method used

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  • Vitamin d3 lactam derivative
  • Vitamin d3 lactam derivative
  • Vitamin d3 lactam derivative

Examples

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Embodiment

[0040] Below, the present invention will be described in further detail through examples, but the present invention is not limited thereto. The compound number in each example corresponds to the compound number shown in the above table, or the compound number in the above reaction scheme 1 or 2.

reference example 1

[0042] Preparation of 2-phenylethylhydroxylamine

[0043]

[0044] In a nitrogen atmosphere, at 0 °C to BH 3 - THF solution in THF 1.1 mL (1.0 M, 1.1 mmol) was added dropwise with a THF solution (2.2 mL) of 160.0 mg trans-β-nitrostyrene (1.1 mmol). Add 3.3 mg of NaBH 4 (0.087mmol), stirred at room temperature for 20 minutes. Add 5 mL of water at 0°C, add 2M aqueous HCl to make the solution acidic, and stir at 65°C for 4 hours. After extraction with ethyl acetate, a 15% aqueous NaOH solution and NaCl were added to the aqueous layer, followed by further extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off. The residue was purified by flash column chromatography (chloroform:methanol=1:0→10:1) to obtain the desired product (62.7 mg, 43%) as white crystals.

[0045] 1 H NMR (CDCl 3 ) δ: 7.47 (brs, 1H), 7.31-7.20 (m, 5H), 3.26 (t, J=7.3Hz, 2H), 2.97 (t, J=7.3Hz, 2H).

reference example 2

[0047] Preparation of 3-phenylpropyl hydroxylamine

[0048]

[0049] (1) Add 166.7 mg of hydroxylamine hydrochloride (2.40 mmol) and 0.7 mL of Et 3 N (5.05 mmol), stirred at room temperature for 2 hours. Add saturated aqueous sodium bicarbonate solution at 0°C, and extract with dichloromethane. After drying over anhydrous magnesium sulfate, it was filtered and the solvent was distilled off. The residue was purified by flash column chromatography (hexane:ethyl acetate=5:1) to obtain white crystalline Compound A (190.0 mg, 100%).

[0050] 1 H NMR (CDCl 3 )δ: 7.47(t, J=6.0Hz, 1H), 7.32-7.19(m, 5H), 6.80(brs, 1H), 2.83(dd, J=7.3, 15.0Hz, 2H), 2.74(m, 1H ), 2.54(m, 1H).

[0051] (2) Add 13.8 mg of NaBH to 46.8 mg of Compound A (0.31 mmol) in methanol solution 2.0 mL at room temperature 3 CN (0.22 mmol). 2M HCl-MeOH solution was added to maintain pH = 3, and stirred at room temperature for 2 hours. After adding 15% NaOH aqueous solution to make it basic, sodium chlorid...

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Abstract

A compound represented by the following formula (1) or a pharmaceutically acceptable solvate thereof. They are useful in treatments for Paget's disease of bone, hypercalcemia, or osteoporosis. (1) In the structural formula, R<1> represents C2-10 alkyl or C7-15 aralkyl in which the aromatic ring may be substituted by C1-6 alkyl, C1-6 alkoxy, hydroxy, halogeno, or trifluoromethyl; and R<2> represents C1-10 alkyl or C7-15 aralkyl in which the aromatic ring may be substituted by C1-6 alkyl, C1-6 alkoxy, hydroxy, halogeno, or trifluoromethyl.

Description

technical field [0001] The present invention relates to vitamin D which can be used as a medicine 3 Lactam derivatives or pharmaceutically acceptable solvates thereof. The present invention further relates to vitamin D effective for the treatment of one or more diseases selected from the group consisting of osteoporosis, hypercalcemia and Paget's disease of bone 3 Lactam derivatives or pharmaceutically acceptable solvates thereof. Background technique [0002] Paget's disease of bone is a disease of unknown cause caused by abnormal hyperabsorption of bone in the pelvis, femur, and cranium, causing symptoms such as bone deformation and bone pain. Currently used therapeutic agents for Paget's disease of bone are bisphosphonate preparations, calcitonin preparations, etc., which are also used as therapeutic agents for osteoporosis, but the dosage of the former must be the dosage for osteoporosis patients. 4 to 5 times, leading to the problem of drug compliance; the latter has...

Claims

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Application Information

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IPC IPC(8): C07D207/273A61K31/593A61P19/08A61P19/10
CPCC07D207/273A61P3/14A61P19/08A61P19/10A61P43/00
Inventor 长泽和夫桥本祐一加藤优子
Owner TEIJIN PHARMA CO LTD
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