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Vitamin-d-like compounds

a technology of vitamin d3 and compounds, applied in the field of new vitamin dlike compounds, can solve the problems that no such vitamin d3-like compounds have been commercially available or proceeded to clinical trials, and achieve the effect of increasing the blood calcium level and strong desirable

Inactive Publication Date: 2011-03-10
CASH JR ROBERT C
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The vitamin D3-like compound provides a stronger agonistic effect with minimal calcium level elevation, potentially expanding therapeutic applications and improving treatment outcomes for various diseases.

Problems solved by technology

However, no such vitamin D3-like compounds have yet been commercially available or proceeded to clinical trials.

Method used

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Examples

Experimental program
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Effect test

example 1

Synthesis of 4′-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2′-methyl-biphenyl-3-carboxylic acid

[0292]

(1) Synthesis of trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl ester

[0293]Pyridine (3 mL, 37.2 mmol) and trifluoromethanesulfonic anhydride (5.7 mL, 34.7 mmol) were added to a solution of 3,3-bis[4-hydroxy-3-methylphenyl]pentane (9.0 g, 31.6 mmol) in dichloromethane (300 mL) at 0° C., and then the mixture was stirred at the same temperature for one hour. Ethyl acetate was added to the reaction mixture. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column (hexane / ethyl acetate=10 / 1 to ethyl acetate only) to give the title compound (4.9 g, 37%).

1H-NMR: 0.62 (t, 6H), 2.203 (q, 4H), 2.20 (s, 3H), 2.38 (s, 3H), 4.67 (s, 1H), 6.68 (d, 1H), 6.80-...

example 2

Synthesis of 4′-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1 -pentenyl)-3-methyl-phenyl]-propyl}-2′-methyl-biphenyl-4 -carboxylic acid

[0306]

[0307]The title compound was synthesized by the same method as in Example 1-(7) using 4-carboxyphenylborane acid and the raw material 1-(6).

1H-NMR: 0.66 (t, 6H), 0.92 (t, 6H), 1.64 (q, 4H), 2.08 (q, 4H), 2.24 (s, 3H), 2.39 (s, 3H), 6.03 (d, 1H), 6.76 (d, 1H), 7.00-7.46 (m, 6H), 7.43 (d, 2H), 8.12 (d, 2H); MS (ESI+): 467 (M-OH)+.

example 3

Synthesis of 5-(4-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-furan-2-carboxylic acid

[0308]

(1) Synthesis of 4-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-1-pentynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol (racemic mixture.)

[0309]A 2.44 M solution of n-butyllithium in hexane (42.8 mL, 104.5 mmol) was added to a solution of 4-[1-ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-phenol (Example 1-(3); 12.22 g, 41.8 mmol) in tetrahydrofuran (300 mL) at 0° C., and the mixture was stirred at the same temperature for 30 minutes. Trimethylacetaldehyde (13.79 mL, 125.4 mmol) was added at 0° C., and the mixture was stirred at the same temperature for 30 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column (hexane / ethyl acet...

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Abstract

The present invention provides a compound represented by the following general formula (I):or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing such a compound, and the like. The compound or a pharmaceutically acceptable salt thereof, the pharmaceutical composition containing such a compound, or the like is useful as a medicine or the like for therapy of benign prostatic hyperplasia, cancer, osteoporosis, psoriasis, secondary hyperparathyroidism, chronic glomerulonephritis, lupus nephritis and / or diabetic nephropathy and the like.

Description

CROSS REFERENCE TO PRIOR RELATED APPLICATIONS[0001]This application is a U.S. national phase application under 35 U.S.C. §371 of International Patent Application No. PCT / JP2006 / 312081, filed Jun. 9, 2006, and claims the benefit of Japanese Patent Application No. 2005-169568, filed Jun. 9, 2005, and Japanese Patent Application No. 2005-259634, filed Sep. 7, 2005, all of which are incorporated by reference herein. The International Application was published in Japanese on Dec. 14, 2006 as International Publication No. WO 2006 / 132442 A1 under PCT Article 21(2).FIELD OF THE INVENTION[0002]The present invention relates to a novel vitamin D-like compound or a pharmaceutically acceptable salt thereof, a medicine containing such a compound (for example, a vitamin D3 receptor agonist), and the like.BACKGROUND OF THE INVENTION[0003]Active vitamin D3 (1α,25-dihydroxyvitamin D3) is a hormone having various physiological effects, and it is suggested that active vitamin D3 can be widely used as a...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07F5/05C07F5/02
CPCC07C51/00C07C59/48C07C59/54C07C59/56C07C59/64C07C59/68C07C59/90C07C65/19C07C229/36C07C259/06C07C259/10C07C271/22C07C309/65C07D213/55C07D237/08C07D239/26C07D277/30C07D307/42C07D307/54C07D307/68C07D309/10C07D333/16C07D335/02C07D405/10C07D409/10C07F5/025C07C2601/08C07C2601/14C07C2601/18A61P13/08A61P13/12A61P17/00A61P17/02A61P17/06A61P17/10A61P17/14A61P17/16A61P19/02A61P19/08A61P19/10A61P21/00A61P25/00A61P25/28A61P27/02A61P29/00A61P3/00A61P3/02A61P3/10A61P3/14A61P35/00A61P35/02A61P37/02A61P37/06A61P5/18A61P7/00A61P9/10
Inventor TAKAHASHI, TADAKATSUONO, YOSHIYUKIKASHIWAGI, HIROTAKAHANEISHI, TSUYOSHISHIMIZU, KAZUKI
Owner CASH JR ROBERT C
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