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Hinokitiol analogues, methods of preparing and pharmaceutical compositions thereof

A mixture and compound technology, which is applied in the direction of drug combination, carbon-based compound preparation, organic compound preparation, etc., can solve problems such as multiple organ failure, increased mortality of intensive care patients, and limited efficacy of iron therapy

Pending Publication Date: 2021-04-16
THE BOARD OF TRUSTEES OF THE UNIV OF ILLINOIS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, iron therapy has limited efficacy and is generally not recommended for some patients
Additionally, blood transfusions have been associated with increased mortality in patients with multiple organ failure and intensive care

Method used

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  • Hinokitiol analogues, methods of preparing and pharmaceutical compositions thereof
  • Hinokitiol analogues, methods of preparing and pharmaceutical compositions thereof
  • Hinokitiol analogues, methods of preparing and pharmaceutical compositions thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0402] The present disclosure includes methods of preparing compounds of the invention (ie, compounds having a structure according to formula (I)) as described below.

[0403] Method A

[0404] A method for preparing 6-bromo-2-methoxycyclohept-2,4,6-trien-1-one or a salt thereof is provided herein:

[0405]

[0406] comprising the steps of combining a Bronsted base and 7,7-dibromo-3-methoxybicyclo[4.1.0]hept-3-en-2-one or a salt thereof:

[0407]

[0408] 6-Bromo-2-methoxycyclohept-2,4,6-trien-1-one or a salt thereof is thus formed.

[0409] In some embodiments, the base is an inorganic base, such as a carbonate. Exemplary carbonates include, but are not limited to, potassium carbonate, sodium carbonate, cesium carbonate, calcium carbonate, and combinations thereof.

[0410] In some embodiments, the method further comprises the step of preparing 7,7-dibromo-3-methoxybicyclo[4.1.0]hept-3-en-2-one or a salt thereof:

[0411]

[0412] The methylating agent and 7,7-...

Embodiment 1

[1231] Example 1: Iron transport restored by small molecules promotes absorption and hemoglobinization in animals

[1232] overview

[1233] This example demonstrates that the small molecule natural product hinokitiol can utilize such gradients to restore iron transport into, within and / or out of cells. The same compounds promote intestinal iron absorption in DMT1-deficient rats and ferroportin-deficient mice, and hemoglobinization in DMT1- and mitochondrial-transferrin-deficient zebrafish. These findings elucidate a general mechanistic framework for site- and orientation-selective restoration of small molecule-mediated iron transport. They also suggest that small molecules that partially mimic the function of transporters lacking iron and possibly other ions may have the potential to treat human disease.

[1234] In most living systems, site- and direction-selective transmembrane ion transport is achieved by the cooperative function of active ion transporters that gener...

Embodiment 2

[1601] Example 2: Synthesis of hinokitiol derivatives β-substituted bromides

[1602]

[1603] ・About 15 derivatives can be prepared with 200 mg bromide

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PUM

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Abstract

Disclosed are analogues of hinokitiol, methods for preparing them, and pharmaceutical compositions thereof. Also disclosed are methods for their use in treating iron-related diseases.

Description

[0001] related application [0002] This application claims priority to U.S. Provisional Application No. 62 / 657,127, filed April 13, 2018, the contents of which are hereby incorporated by reference in their entirety. [0003] Statement of Government Funding [0004] This invention was made with Government support under Grant No. GM118185 awarded by the National Institutes of Health. The government has certain rights in this invention. Background technique [0005] Iron homeostasis is critical to the proper function of the body. Since iron is critical for hemoglobin production, insufficient iron levels can lead to iron deficiency anemia. Iron overload can also disrupt iron balance by inappropriately increasing intestinal iron absorption. This increase often leads to iron deposition in the liver, pancreas, heart, pituitary gland, and other organs, leading to tissue damage and impairment of the normal function of these organs. [0006] Current treatment options for iron-rela...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P7/06A61P31/04A61P31/18C07D263/02C07D263/20C07D263/30C07D263/34C07D263/38
CPCC07C45/292C07C45/61C07C45/68C07C45/65A61P7/06C07C49/717C07C49/513C07C49/753C07C49/503C07C49/507B01J23/44A61K31/122A61K45/06C07C2601/02C07C2601/04C07C2601/08C07C2601/14C07C61/22
Inventor M·D·伯克A·S·格里洛A·G·乔飞A·桑塔马里亚D·布莱尔A·布莱克
Owner THE BOARD OF TRUSTEES OF THE UNIV OF ILLINOIS
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