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Pharmaceutical compounds

A compound and drug technology, applied in the field of drug compounds

Inactive Publication Date: 2005-01-05
伊莱克斯肿瘤学研究股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most therapeutic agents that stimulate bone formation or inhibit bone turnover are hormones or hormone derivatives (estrogens, anabolic steroids, calcitonin, parathyroid hormone, vitamin D), with substantial side effects

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-4

[0148] Examples 1-4 of the present application describe the synthesis of the following compounds:

[0149]

[0150] in:

[0151] -X 0 is H, an alkyl group having 1 to 4 carbon atoms;

[0152] -X 4 is optionally substituted benzyl (Bn).

[0153] Examples 5-9 describe the osteoanabolic activity of compounds of formula (I).

Embodiment 1

[0154] Example 1: Tetraethyl 2-(3-benzyl-4-hydroxynaphthyl)vinylidene-1,1-diphosphonate

[0155]

[0156] a) 3-benzyl-4-hydroxynaphthaldehyde

[0157] Add potassium tert-butoxide (36.0 g, 0.32 mol) to a solution of 1-tetralone (23.4 g, 0.16 mol) and benzaldehyde (16.96 g, 0.16 mol) in tert-butanol (1600 ml), and make the resulting mixture under nitrogen Reflux overnight. The mixture was cooled, acidified with dilute HCl solution, and concentrated in vacuo to remove tert-butanol. The concentrated aqueous phase was extracted with ethyl acetate, the organic phase was evaporated and the residue obtained was purified by column chromatography to obtain 34 g of 2-benzyl-1-naphthol.

[0158] Add anhydrous tin chloride (21.38g, 82.1mmol) to a solution of 2-benzyl-1-naphthol (10.67g, 45.6mmol) in 60ml of dichloromethane at 0°C, and then add 1,1 dichloromethyl Methyl ether (7.92 g, 68.86 mmol). The resulting mixture was stirred at 0 °C for 30 minutes, then poured into ice water. ...

Embodiment 2

[0169] Example 2: Tetraisopropyl 2-(3-benzyl-4-hydroxynaphthyl)vinylidene-1,1-diphosphonate

[0170]

[0171] Titanium tetrachloride (10.89 g, 57.3 mmol) was added dropwise to 60 ml of anhydrous tetrahydrofuran while stirring. The following compounds were then added successively at 5 minute intervals while stirring at 0-5°C: 3-benzyl-4-hydroxynaphthaldehyde (5.0 g, 19.1 mmol), followed by tetraisopropylmethylene diphosphate ( 7.9 g, 22.9 mmol), and finally N-methylmorpholine (11.58 g, 114.6 mmol). After the addition was complete, the reaction was stirred at room temperature for 3 hours, then ice water was added. The quenched reaction mixture was extracted with diethyl ether and the ether extract was back extracted with brine to neutral pH and concentrated in vacuo to give a residue which was triturated in a mixture of petroleum ether and diethyl ether and then dissolved in tert-butyl methyl ether Purification by recrystallization afforded 4.1 g (37%) of the title compound...

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Abstract

The invention provides the use of an aryl-substituted 1,1-diphosphonate for the manufacture of a medicament for stimulating bone formation; said aryl-susbtituted 1,1-diphosphonate being a compound of formula (I) in which A is (a) or (b) or (c) where: X<O> is H, an alkyl group having from 1 to 4 carbon atoms; X<1>, X<2> and X<3> are identical or different and are H, a straight or branched alkyl or alkoxy group having from 1 to 8 carbon atoms, X<4> is H, a straight or branched alkyl group having from 1 to 8 carbon atoms, an optionally substituted benzyl group, X<5> is H, a straight or branched alkyl group having from 1 to 8 carbon atoms, X<6> is H or an alkyl group having from 1 to 4 carbon atoms, q is 0 or 1, R<1>, R<2>, R<3> and R<4> are identical or different and are H, a straight, branched or cyclic alkyl group comprising from 1 to 8 carbon atoms, or R<1>, R<2> and R<3> and R<4> may form an alkylidenedioxy ring comprising from 2 to 8 carbon atoms, L is -CH=CH-CH2-, -(CH2)n, -O(CH2)n, -S-, -SO2, -S(CH2)n-, -SO2(CH2)n, where n is an integer from 1 to 7, or together with B, L is (CH=CH)k-(CH2)dCH=where k is 0 or 1 and d is an integrer from 0 to 4, -B is H, an alkyl group having from 1 to 4 carbon atoms, -t is 0 or 1, with the proviso that t is 0 only when L, together with B, is (CH=CH)k-(CH2)d-CH= where k and d are as described above, and with the further proviso that when L is -(CH2)n or -S-, at least one of <1>, R<2>, R<3> and R<4> is other than hydrogen.

Description

[0001] The present invention relates to the use of bisphosphonate compounds for the treatment or prevention of bone diseases, such as osteoporosis, in particular bone diseases requiring osteoanabolic activity. [0002] Herein, the terms "bisphosphonate" and "bisphosphonate" are used interchangeably with "bisphosphonic acid" and "bisphosphonic acid", respectively; the terms "bisphosphonate" and "bisphosphonic acid" are old names , but is still widely used. Background of the invention [0003] Osteoporosis is caused by an imbalance between bone formation and bone resorption, leading to bone loss and fractures. Osteoporosis represents a serious public health problem, and it is estimated that one in two women over the age of 50 will suffer an osteoporotic fracture during the remainder of her lifetime. [0004] Two approaches are currently used to manipulate bone mass, namely the prevention of bone resorption and the stimulation of bone formation (osteoabsorption). Bisphosphonic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K45/00A61K31/00A61K31/663A61P1/02A61P3/14A61P5/06A61P13/08A61P19/08A61P19/10A61P35/00A61P43/00
CPCA61K31/663A61P1/02A61P3/14A61P5/06A61P13/08A61P19/08A61P19/10A61P35/00A61P43/00
Inventor E·J·尼瑟尔Y·古扬-盖林C·L·班赞L·M·古彦H·T·范
Owner 伊莱克斯肿瘤学研究股份有限公司
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