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Spiro compounds, medicinal compositions containing the same and intermediates of the compounds

A technology of spiro compounds and compounds, applied in the field of new spiro compounds, can solve the problems of no SERM usefulness, etc.

Inactive Publication Date: 2005-11-30
SUMITOMO DAINIPPON PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is nothing in the literature about its usefulness as a SERM

Method used

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  • Spiro compounds, medicinal compositions containing the same and intermediates of the compounds
  • Spiro compounds, medicinal compositions containing the same and intermediates of the compounds
  • Spiro compounds, medicinal compositions containing the same and intermediates of the compounds

Examples

Experimental program
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Effect test

reference example 1

[0308] Preparation of 5-methoxy-2-(5-methoxy-1-indanyl)benzoic acid:

[0309] (1) Suspend 22.3g of magnesium in 400mL of tetrahydrofuran, add 243g of 2-(2-bromo-5-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole to it 1 / 10 of the tetrahydrofuran (2L) solution. A small amount of iodine was added, and the reaction solution was heated to reflux. After the violent reaction was over, the remaining oxazole solution was added thereto under heating and reflux in 1 hour, and then heated and refluxed for 2 hours after the dropwise addition. Thereto was added dropwise a solution of 118 g of 5-methoxy-1-indanone in tetrahydrofuran (1 L) over 0.5 hours under ice-cooling. After stirring at room temperature for a whole day and night, 400 mL of saturated ammonium chloride aqueous solution was added and stirred. After separating the organic phase, the organic phase was washed with water and saturated brine. The organic phase was dried over sodium sulfate and concentrated under reduced pressu...

reference example 2

[0314] Preparation of ethyl 2-diazo-3-[5-methoxy-2-(5-methoxy-1-indanyl)phenyl]-3-oxopropionate:

[0315] (1) Suspend 83g of 5-methoxy-2-(5-methoxy-1-indanyl)benzoic acid in 300mL of toluene, add 33.2mL of oxalyl chloride and 0.1mL of dimethylformamide, at room temperature Stirring was continued for 4 hours. The reaction solution was concentrated under reduced pressure to obtain an oily substance.

[0316] (2) Dilute 789 mL of 20% hexamethyldisilazane potassium salt toluene solution with 700 mL of tetrahydrofuran, add 68 mL of ethyl acetate dropwise thereto at -78°C over 1 hour, and then stir at the same temperature for 1 hour. A solution of the above oil in tetrahydrofuran (300 mL) was added dropwise thereto over 1 hour, followed by stirring for another 1 hour. 600 mL of saturated ammonium chloride aqueous solution was added to terminate the reaction. After separating the organic phase, the organic phase was washed with water and saturated brine. After drying the organic p...

reference example 3

[0320] Preparation of 1-(4-bromophenyl)-4-ethylpiperazine

[0321] (1) Add 20 mL of water and 0.6 g of sodium bicarbonate to a solution of 1.0 g of 1-(4-bromophenyl)piperazine in ethyl acetate (20 mL), and stir vigorously. 0.5 mL of acetic anhydride was added thereto, and stirring was continued at room temperature for 2 hours. The organic phase was separated, washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over sodium sulfate. The organic phase was concentrated under reduced pressure to give an oil.

[0322] (2) The above oil was dissolved in 5 mL of tetrahydrofuran, 4.5 mL of 2.0 M borane dimethyl sulfide complex in tetrahydrofuran was added, and stirred at room temperature for a whole day and night. After adding 10 mL of 20% hydrochloric acid and heating to reflux for 1 hour, tetrahydrofuran was distilled off under reduced pressure. A 15% aqueous sodium hydroxide solution was added until the pH of the reaction liquid r...

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Abstract

Spiro compounds represented by the following general formula (I) or pharmaceutically acceptable acid-addition salts thereof: (I) wherein R<1> and R<2> are the same or different and each represents hydrogen, chlorine, etc.; n is 1, 2 or 3; a bond having a broken line represents a single or double bond; and A represents -X-(CH2)q-N(R<3>)(R<4>), a group represented by the following general formula (a), etc. (a) (wherein X represents oxygen or sulfur; q is 2 or 3; R<3> and R<4> are the same or different and each represents C1-6 alkyl, etc., or R<3> and R<4 >may form together with the adjacent nitrogen atom a piperidine ring, etc. optionally having one or two C1-6 alkyl substituents, etc.; R<5> represents C1-6 alkyl, etc.; R<6> represents hydrogen, etc.; and r and t independently represent each 1 or 2. These compounds are useful as selective estrogen receptor modulators having an effect of ameliorating symptoms of menopause. They are also expected as being usable as preventives and / or remedies for osteoporosis, symptoms of menopause and breast cancer.

Description

technical field [0001] The present invention relates to novel spirocyclic compounds that function as selective estrogen receptor modulators, and more particularly to spiro[indene-1,1'-indane] derivatives and analogs thereof, compounds containing said compounds Pharmaceutical compositions and intermediates of the compounds. Background technique [0002] Women's ovarian function declines sharply in the years before and after menopause, and the estrogen value in blood after menopause drops to less than 1 / 10 of that before menopause. Therefore, due to the lack of estrogen, postmenopausal women are prone to symptoms such as abnormal lipid metabolism, arteriosclerosis, osteoporosis, memory impairment or cognitive impairment, in addition to the so-called climacteric syndrome. In order to improve various symptoms of the postmenopausal women, hormone replacement therapy (hereinafter referred to as HRT) or estrogen replacement therapy (hereinafter referred to as ERT) using a combinat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/40A61K31/445A61K31/4453A61K31/451A61K31/495A61K31/55A61P15/12A61P19/10A61P35/00A61P43/00C07C217/20C07C217/24C07D211/14C07D295/092
CPCC07C217/20A61K31/495C07C217/24C07C2103/97A61K31/451A61K31/4453A61K31/445C07D211/14C07D295/088A61K31/40A61K31/55A61P15/12A61P19/10A61P35/00A61P43/00C07C2603/97C07C217/18C07D211/22
Inventor 渡边信英中川拓士辻淳一凑久夫池野明久小早川千衣
Owner SUMITOMO DAINIPPON PHARMA CO LTD
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