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Phenyl quinolines and their use as estrogenic agents

A technology of quinoline and phenyl, which is applied in the field of phenylquinoline compounds, can solve problems such as unexplained cell-specific effects of the same compound

Inactive Publication Date: 2006-08-23
WYETH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The exact reason why the same compound can have cell-specific effects has not been elucidated, but differences in receptor conformation and / or coregulatory protein milieu have been suggested

Method used

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  • Phenyl quinolines and their use as estrogenic agents
  • Phenyl quinolines and their use as estrogenic agents
  • Phenyl quinolines and their use as estrogenic agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Method A: Preparation of ethyl substituted benzoyl acetates 1.

[0106] A typical procedure for the preparation of ethyl (3-fluoro-4-methoxybenzoyl)acetate (1b) is described

[0107] Add NaH (60% dispersion in mineral oil, 42 g, 1.05 mol, 3 equiv, washed with hexane) and CO(OEt) via an addition funnel under reflux under nitrogen. 2 (85mL, 0.70mol, 2eq) in 1,4-dioxane (300mL) was added dropwise to a suspension of 3-fluoro-4-methoxyacetophenone (58.9g, 0.350mol) in 1,4- Dioxane (150 mL) solution. After the addition was complete, the mixture was stirred at reflux for an additional 30 min. After cooling to room temperature, glacial acetic acid was slowly added to acidify the reaction mixture, and the solvent was removed under reduced pressure. Water was then added and the mixture was extracted with EtOAc. Organic layer water, NaHCO 3 washed with aqueous solution, brine, and dried (Na 2 SO 4 ), filtered and concentrated to obtain pure crude product as a yellow oil, wh...

Embodiment 1a

[0110] Ethyl (4-methoxybenzoyl)acetate (1a).

[0111] This compound was prepared by Method A using 4-methoxyacetophenone. Yellow oil; Yield: 95%;

[0112] 1 H-NMR (300MHz, CDCl 3 ): δ1.26(t, J=7.3Hz, 3H), 3.88(s, 3H), 3.94(s, 2H), 4.21(q, J=7.3Hz, 2H), 6.95(m, 2H), 7.93 (m, 2H). Minortautomer: 1.33(t, J=7.3Hz, 3H), 3.86(s, 3H), 4.27(q, J=7.3Hz, 2H), 5.57(s, 1H), 6.92(m, 2H), 7.74 (m, 2H), 12.65 (s, 1H); MS (ESI) m / z 223 ([M+H] + );

[0113] Elemental Analysis, C 12 h 14 o 4 Theoretical values: C: 64.85, H: 6.35. Found values: C: 64.92, H: 6.11.

Embodiment 1b

[0115] Ethyl (3-fluoro-4-methoxybenzoyl)acetate (1b).

[0116] This compound was prepared according to Method A. Yellow oil; Yield: 94%;

[0117] 1 H-NMR (300MHz, CDCl 3 )δ1.26(t, J=7.1Hz, 3H), 3.93(s, 2H), 3.97(s, 3H), 4.21(q, J=7.1Hz, 2H), 7.01(dd, J=8.4, 8.5 Hz, 1H), 7.72(m, 2H). Minor tautomer: 1.33(t, J=7.1Hz, 3H), 3.94(s, 3H), 4.28(q, J=7.1Hz, 2H), 5.57(s, 1H), 6.99(t, J=8.4Hz, 1H), 7.54(m, 2H), 12.62(s, 1H); MS(ESI) m / z 241([M+H] + );

[0118] Elemental Analysis, C 12 h 13 FO 4 Theoretical values: C: 60.00, H: 5.45. Found values: C: 60.12, H: 5.25.

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Abstract

This invention provides estrogen receptor modulators of formula: (I), having the structure wherein, R<1>, R<2>, R<3>, R<4>, R<5> and R<6> are as defined in the specification, or a N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof.

Description

field of invention [0001] The present invention relates to phenylquinoline compounds, their use as estrogenic agents and processes for their preparation. Background of the invention [0002] The pleiotropic effects of estrogen in mammalian tissues have been well documented and estrogen is now recognized to affect many organ systems [Mendelsohn and Karas, New England Journal of Medicine 340:1801-1811 (1999), Epperson et al., Psychosomatic Medicine 61:676- 697 (1999), Crandall, Journal of Womens Health & Gender Based Medicine 8: 1155-1166 (1999), Monk and Brodaty, Dementia & Geriatric Cognitive Disorders 11: 1-10 (2000), Hurn and Macrae, Journal of Cerebral Blood Flow & Metabolism 20 (1-65: 2000), Calvin, Maturitas 34: 195-210 (2000), Finking et al., Zeitschrift fur Kardiologie 89: 442-453 (2000), Brincat, Maturitas 35: 107-117 (2000), Al-Azzawi, Postgraduate Medical Journal 77 : 292-304 (2001)]. Estrogen can affect tissue in several ways. The most typi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/20C07D409/04C07D417/04C07D401/04A61K31/47A61K31/407A61K31/695C07D215/36C07D413/04C07F7/02
CPCC07D413/04C07D215/20C07D401/04A61P1/04A61P1/16A61P3/04A61P3/06A61P3/10A61P3/14A61P9/00A61P9/04A61P9/10A61P13/02A61P13/08A61P13/12A61P15/02A61P15/08A61P15/12A61P17/00A61P17/04A61P17/10A61P17/14A61P19/00A61P19/02A61P19/08A61P19/10A61P25/00A61P25/28A61P29/00A61P35/00A61P35/02A61P37/00
Inventor A·T·伍S·T·科恩R·E·穆肖
Owner WYETH LLC
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