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Processes for preparing gonadotropin releasing hormone receptor antagonists

A technology of alkyl and compound, which is applied in the field of preparation of gonadotropin-releasing hormone (GnRH) receptor antagonist, and can solve problems such as not being able to be used orally

Inactive Publication Date: 2007-05-23
WYETH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It cannot therefore be used orally and must be given parenterally, for example by intravenous, subcutaneous or intramuscular injection

Method used

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  • Processes for preparing gonadotropin releasing hormone receptor antagonists
  • Processes for preparing gonadotropin releasing hormone receptor antagonists
  • Processes for preparing gonadotropin releasing hormone receptor antagonists

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] LCMS analysis was performed on an open-frame Agilent chromatograph with UV and mass detectors, 5 cm C18 column, 5 min 95% water to 95% MeCN gradient. HPLC analysis was performed on a Waters liquid chromatograph, 15 cm C18 column, 20 min elution with a 10 min gradient of 95% water to 95% MeCN (0.05% TFA) and a flow rate of 1 mL / min.

N-(2-bromophenyl)-4-tert-butylbenzamide

[0113] 2-Bromoaniline (98%, Oakwood 005347, 214 g, 1.25 moles), sodium bicarbonate (270 g, 3.2 moles), THF (500 mL) and water (500 mL) were charged into a device equipped with an overhead stirrer, thermometer and Add a 500 ml addition funnel to a 5 L round bottom flask. A solution of tert-butylbenzoyl chloride (>98%, Fluka 19660, 250 mL, 1.37 mol) in 250 mL THF was charged to the addition funnel and added slowly (over 25 minutes) to the stirred reaction mixture in the flask (Without external heating or cooling, a slight warming was observed and the temperature in the flask rose to 35°C).

[01...

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Abstract

The present invention relates to methods of making Gonadotropin Releasing Hormone ('GnRH') (also known as Leutinizing Hormone Releasing Hormone ('LHRH')) receptor antagonists.

Description

[0001] This application claims the benefit of US Provisional Application Serial No. US 60 / 580,665, filed June 17, 2004, which is hereby incorporated by reference in its entirety. [0002] Various publications are cited in this application. The contents of these publications in their entirety are incorporated into this application by reference to more fully describe the state of the art to those skilled in the art as of the date of the invention described and claimed herein. [0003] This patent specification contains subject matter that is subject to copyright protection. The copyright owner has no objection to the facsimile reproduction by anyone of the patent document or the patent disclosure as it appears in the USPTO patent file or records, but otherwise reserves any and all copyrights. field of invention [0004] The present invention relates to a process for the preparation of gonadotropin releasing hormone ("GnRH") (also known as luteinizing hormone releasing hormone (...

Claims

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Application Information

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IPC IPC(8): C07D403/12A61K31/496
CPCC07D235/08C07D403/12
Inventor A·V·贡查洛夫G·哈菲佐瓦J·R·波托斯基D·M·哈林
Owner WYETH LLC
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