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(4-hydroxyphenyl)-1h-indole-3-carbaldehyde oxime derivative as estrogenic agents

A technology of hydroxyphenyl and formaldehyde oxime, applied in the field of -1H-indole-3-formaldehyde oxime derivatives

Inactive Publication Date: 2006-11-22
WYETH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the consequences and subtleties of these changes have only recently been discovered

Method used

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  • (4-hydroxyphenyl)-1h-indole-3-carbaldehyde oxime derivative as estrogenic agents
  • (4-hydroxyphenyl)-1h-indole-3-carbaldehyde oxime derivative as estrogenic agents
  • (4-hydroxyphenyl)-1h-indole-3-carbaldehyde oxime derivative as estrogenic agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1a

[0059] 1-(4-Benzyloxyphenyl)-2-methyl-1H-indole

[0060] To a mixture of 2-methylindole (3.28 g, 25 mmol), 4-benzyloxyiodobenzene (7.76 g, 25 mmol), potassium carbonate (2.65 g, 25 mmol), and N-methylpyrrolidone (250 mL) was added Cuprous (I) bromide (0.5 g, 3.5 mmol). The stirred solution was heated to 180°C for 18 hours. After the reaction mixture was cooled, it was poured onto ice and extracted with ethyl acetate. After washing with water and brine, the organic layer was washed with anhydrous MgSO 4 Drying and removal of solvent gave a dark liquid. Purification by silica gel chromatography (2% ethyl acetate-hexanes) afforded the title compound (30%) as a white solid: mp 95-96°C; 1 H NMR (DMSO-d 6 ): δ2.24(3H, s), 5.19(2H, s), 6.38(1H, s), 6.93-7.04(3H, m), 7.20(2H, d, J=1.9Hz), 7.23(2H, d, J=3.1Hz), 7.32-7.53 (8H, m); MS m / z (M+H) + 314:

[0061] to C 22 h 19 NO0.1H 2 Analysis of O:

[0062] Calculated: C, 83.83; H, 6.14; N, 4.44.

[0063] Found: C, 83.84; H, 6...

Embodiment 1b

[0065] 5-fluoro-1-(4-benzyloxyphenyl)-2-methyl-1H-indole

[0066] 5-Fluoro-2-methylindole (5.0 g, 33.5 mmol) was reacted with 4-benzyloxyiodobenzene (10.40 g, 33.5 mmol) according to the procedure used in the previous example 1a to give a white solid (23%) : mp 94-95°C; 1 H NMR (DMSO-d 6 ): δ2.23(3H, s), 5.19(2H, s), 6.39(1H, s), 6.84-6.94(2H, m), 7.19-7.29(3H, m), 7.34-7.44(5H, m ), 7.51 (2H, d, J=7.1Hz); MS m / z (M+H) + 332.

[0067] to C 22 h 18 Analysis of NOF:

[0068] Calculated: C, 79.74; H, 5.47; N, 4.23.

[0069] Found: C, 79.54; H, 5.54; N, 4.21.

Embodiment 1c

[0071] 5-Chloro-1-(4-methoxymethyloxyphenyl)-2-methyl-1H-indole

[0072] 5-Chloro-2-methylindole (4.14g, 25mmol) was reacted with 4-methoxymethyloxyiodobenzene (6.20g, 25mmol) according to the steps adopted in previous Example 1a to obtain a colorless liquid ( 19%): 1 H NMR (DMSO-d 6 ): δ2.25(3H, s), 3.44(2H, s), 5.28(2H, s), 6.40(1H, s), 6.96(1H, d, J=8.8Hz), 7.02(1H, dd, J=2.0Hz, J=8.8Hz), 7.22 (2H, d, J=8.8Hz), 7.36 (2H, d, J=8.8Hz), 7.55 (1H, d, J=2.0Hz); MS m / z(M+H) + 302 / 304 (1Cl).

[0073] to C 17 h 16 ClNO 2 Analysis of:

[0074] Calculated: C, 67.66; H, 5.34; N, 4.64.

[0075] Found: C, 67.49; H, 5.17; N, 4.51.

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Abstract

This invention provides estrogen receptor modulators of formula (I), having the structure where R1, R2, R3, and R4 are as defined in the specification, or a pharmaceutically acceptable salt thereof.

Description

field of invention [0001] The present invention relates to (hydroxyphenyl)-1H-indole-3-carbaldehyde oxime derivatives, their use as estrogenic agents, and their preparation methods. Background of the invention [0002] Estrogen has multiple functions in mammalian tissues that have been documented in many documents, and it is known that estrogen can affect many organ systems [Mendelsohn and Karas, New England Journal of Medicine 340:1801-1811 (1999), people such as Epperson, 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: 631-652 (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 act on tis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/404A61K31/403A61P5/30C07D209/14C07D209/88
Inventor R·E·穆肖S·M·鲍恩E·S·曼纳斯
Owner WYETH LLC
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