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Steroidal c- 17 benzoazoles

A composition and compound technology, applied in the direction of steroids, drug combinations, medical preparations containing active ingredients, etc.

Inactive Publication Date: 2013-10-16
UNIV OF MARYLAND BALTIMORE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although, ketocamide is no longer used due to hepatotoxicity and other side effects, this suggests that more potent and alternative CYP17 inhibitors may become effective agents for the treatment of the disease, even in advanced stages and possible hormonal in resistant patients

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  • Steroidal c- 17 benzoazoles
  • Steroidal c- 17 benzoazoles
  • Steroidal c- 17 benzoazoles

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Embodiment

[0073] biological research

[0074] CYP17 inhibition studies: The CYP17 inhibition coordination assay was done following our previously published procedure, where intact cytochrome P450cl7-expressing E. coli was used as the enzyme source (Grigoryev et al., "Cytochrome P450cl7-expressing Escherichia coli as a first-step screening system for 17[alpha]-hydroxylase-C17,20-lyase inhibitors", Anal.Biochem.;1999,267,319-330; and "Effects of new 17α-hydroxylase / C17,20-lyase inhibitors on LNCaP prostate cancer cell growth in vitro and in vivo", Br.J.Cancer, 1999, 81, 622-630. The IC of the compound 50 Values ​​were determined from dose-response curves and are listed in Table 1. Ketoconazole, IC of Abiraterone 50 values ​​(one CYP17 inhibitor in clinical trials (O'Donnell above), Chart 1) and 3β-hydroxy-17-(lH-imidazol-l-yl)androst-5,16-diene (VN / 85-1, compound 16, Diagram 1, is considered to be the most potent CYP17 inhibitor (Njar et al, mentioned above, Current Pharm.Design, 1999...

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Abstract

Described are steroidal C-17 benzoazoles, pyrimidinoazoles (azabenzoazoles) and diazines. Methods for their synthesis are also described, which include methods having a step of nucleophilic vinylic "addition-elimination" substitution reaction of 3²-acetoxy-17-chloro-16-formylandrosta-5,16-diene or analogs thereof and benzoazole or pyrimidinoazole nucleophiles and methods having a palladium catalyzed cross-coupling reaction of 17-iodoandrosta-5,16-dien-3²-ol or analogs thereof with tributylstannyl diazines. The compounds are potent inhibitors of human CYP 17 enzyme as well as potent antagonists of both wild type and mutant androgen receptors (AR). The compounds are useful for the treatment of human prostate cancer.

Description

[0001] The patent application of the present invention is the international application number PCT / US2006 / 007143, the international application date is March 2, 2006, the application number entering the Chinese national phase is 200680006463.2, and the name is "new C-17-heteroaryl steroid CYP17 Inhibitor / Antiandrogen Substance: Its Synthesis, In Vitro Biological Activity, Pharmacokinetics and Antitumor Activity" is a divisional application of the invention patent application. technical field [0002] This application claims the priority date of US Provisional Application No. 60 / 657,390, filed March 2, 2005, which is incorporated herein by reference. [0003] The U.S. government has a fee-paid license to this invention, with the right, under limited circumstances, to request permission from the patentee for reasonable cause during the term granted by the National Institutes of Health (NIH) under grant number CA27440 others. [0004] The present invention provides novel chemica...

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Application Information

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IPC IPC(8): A61K31/58A61P35/00A61P13/08
CPCC07J43/003A61P13/08A61P35/00A61K31/58C07J43/00
Inventor A·布罗迪V·恩雅
Owner UNIV OF MARYLAND BALTIMORE
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