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Rifamycin analogs and uses thereof

一种动物、卤素的技术，应用在洗涤剂组合物、有机化学、化学仪器和方法等方向，能够解决菌株数量增长、无法有效治疗等问题

Inactive Publication Date: 2009-03-25
ACTIVBIOTICS PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many pathogens exist for which there is no effective treatment, and the number of strains resistant to existing drugs continues to grow

Method used

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  • Rifamycin analogs and uses thereof
  • Rifamycin analogs and uses thereof
  • Rifamycin analogs and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0170] Example 1: General Coupling Method

[0171] Synthetic 5'-substituted benzoxazine rifamycins, 5'-substituted benzothiazine rifamycins, and 5'-substituted benzodiazines rifamycins can all follow the same procedure listed in Scheme 1 The general route is carried out using the general method disclosed in US Patent No. 4,965,261 to add the amino group to the 5'-position. In this scheme, rifamycin azaquinone of formula II is dissolved in a suitable solvent, such as DMSO, and then reacted with amine or formula III in the presence of manganese dioxide at room temperature for several hours to form azaquinone of formula IV . If desired, the azabenzoquinone of formula IV can be further reacted with a deprotecting reagent to remove the P' and / or any P" protecting groups introduced at the 25-position, X, 21 and 23 positions in the amine of formula III In some embodiments, a group that is beneficial to pharmacokinetic properties can be further introduced at the 25-position, for exa...

Embodiment 2

[0180] Example 2: General procedure for deacetylation

[0181] A compound of formula VI (-100 mmol) was dissolved in methanol (5 mL) and treated with saturated sodium hydroxide in methanol (5 mL) at room temperature for 0.5 h-3 h. The reaction mixture was poured into saturated ammonium chloride solution, and extracted with chloroform. The organic phase was washed with water (2×), Na 2 SO 4 dry. After filtration the solvent is removed in vacuo to give the desired deacetylated product of formula X. If desired, the product can be purified by flash chromatography (silica gel) using an appropriate solvent system (eg 1-10% methanol in dichloromethane).

[0182]

Embodiment 3

[0183] Example 3: Synthesis of Compound 1 (3'-hydroxyl-5'-(3-hydroxyl-1-azetidinyl)benzoxazine rifamycin), (see Table 1 for structure)

[0184] The title compound was prepared using the general coupling procedure of Example 1 using compound 100 (1 mmol), 3-hydroxyoxazetidine, TBDMS ether (2.5 mmol) and manganese(IV) oxide (10 mmol). Removal of the silyl protecting group with tetrabutylammonium fluoride affords compound 1.

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Abstract

The present invention features rifamycin analogs and methods of using these compounds to treat a variety of microbial infections.

Description

Background technique [0001] The present invention relates to the field of antibiotic medicine. [0002] The use of antibiotics by humans can be regarded as a very great revolutionary experiment, through which the incomplete natural selection behavior in reality can be observed. In the past 50 years, the number of types and strains of pathogenic bacteria and commensal bacteria resistant to antibiotics and the number of antibiotics they can resist in the world have actually shown a single upward trend. So infections that were once easily treatable with chemotherapy are no longer so easy to treat. Clearly, the development and spread of resistance is attributable to the use and overuse of antibiotics. Increased resistance of bacterial infections to antibiotic therapy has been well documented and is now a recognized medical problem, especially in nosocomial infections. See, eg, Jones et al., Diagn. Microbiol. Infect. Dis. 31:379-388, 1998; Murray, Adv. Intern. Med. 42:339-367, 1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C11D15/00
CPCC07D519/00C07D498/18A61P31/04
Inventor 约翰·H·范·迪泽阿瑟·F·米凯利斯威廉·B·盖斯杜格尔拉斯·G·斯塔福德约瑟夫·雷克翔·Y·于詹姆斯·M·谢德莱茨基杨影飞
Owner ACTIVBIOTICS PHARMA
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