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Biguanide and dihydrotriazine derivatives

A technology of propyl biguanide and compound, which is applied in the field of biguanide and dihydrotriazine derivatives, and can solve problems such as increased activity

Inactive Publication Date: 2010-12-22
JACOBUS PHARMA CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although imidodicarbonimidic diamides exhibit intrinsic biological activity in their purported therapeutic applications, the claimed compounds can be markedly enhanced by in vivo conversion to their corresponding dihydrotriazine metabolites

Method used

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  • Biguanide and dihydrotriazine derivatives
  • Biguanide and dihydrotriazine derivatives
  • Biguanide and dihydrotriazine derivatives

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0197] In one embodiment, the present invention relates to the preparation method of antibacterial compound, comprises the steps:

[0198] Under sufficient conditions, the compound of general formula II is contacted with the compound of general formula III for a period of time,

[0199]

[0200] To obtain a compound of general formula I or a pharmaceutically acceptable salt thereof:

[0201]

[0202] in:

[0203] R 1 is R x , substituted aryl, substituted alkyl, substituted fused cycloalkaryl, substituted aralkyl, substituted cycloalkylarylalkyl, substituted heteroaryl or substituted heteroaralkyl, where the last seven groups are selected Substituted by at least one substituent from the following: -CN, -OCF 3 , haloalkoxy, -SR 4 ,-OCF 3 ,-SCF 3 , Haloalkylthio, -NR 5 R 6 ,-SO 2 R 4 ,-SO 2 NR 5 R 6a , heteroaryl, heterocyclyl or R 10 O-(CH 2 CH 2 O) j - or a combination thereof;

[0204] R x is substituted or unsubstituted following structural formula:...

Embodiment 1

[0305] Preparation of compound 1-(3-(4-trifluoromethoxy) phenoxy) propyl bromide of general formula IV

[0306] 4-trifluoromethoxyphenol (5.0g, 28mmol), 1,3-dibromopropane (28g, 40mmol), sodium hydroxide (7.0g of 24% aqueous solution) and tetrabutylammonium bisulfate (0.2g ) mixture was stirred at 70°C for 48 hours. The reaction layer was separated. Excess 1,3-dibromopropane was removed from the organic phase under high vacuum at a bath temperature of 100°C to give 8.5 g of crude product (102%, based on expected weight recovery).

Embodiment 2

[0308] Preparation of 2-(3-(4-trifluoromethoxyphenoxy)propyl acetylhydroxamate of compound of general formula V

[0309] The crude bromide of Example 1 (8.5 g) was heated with potassium acetohydroxamate (4.75 g, 42 mmol) in 20 mL of ethanol at 55°C for 16 hours. The crude product solution was evaporated on a rotary evaporator, diluted with water (20ml) and extracted with ethyl acetate (2x25ml). The combined organic extracts were dried over anhydrous potassium carbonate, filtered, and the solvent was evaporated to give 7.0 g of product as an oil. The resulting material was used without further purification in the following examples.

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Abstract

Biguanide and dihydrotriazine derivatives, preferably substituted asymmetrical imidodicarbonimidic diamides derived from hydroxylamines, and compositions containing biguanide and dihydrotriazine derivatives are disclosed. In addition, methods of using the biguanide and dihydrotriazine derivatives, inter alia, as antimicrobial agents and methods of using the dihydrotriazine derivatives in biological assays are disclosed. Methods of making the biguanide and dihydrotriazine derivatives are also disclosed.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of U.S. Application Serial No. 60 / 428,306, filed November 22, 2002, and U.S. Application Serial No. ____, filed November 18, 2003, the disclosures of which are incorporated herein by reference in their entirety . field of invention [0003] The present invention generally relates to biguanide and dihydrotriazine derivatives. More particularly, the present invention relates to biguanide and dihydrotriazine derivatives, compositions containing biguanide and dihydrotriazine derivatives, methods of using biguanide and dihydrotriazine derivatives, etc. Methods of Hydrogen Triazine Derivatives. Background of the invention [0004] Certain dihydrotriazine derivatives have been studied as antimalarial compositions (Onori et al., Ann. lst Super Sanita., 1989, 25:659-74). However, these derivatives are poorly absorbed and have been shown to be less efficient in inducing cure in malaria-infe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C279/26C07D251/10C07C323/20C07C317/22C07D319/20C07D317/64A61K31/155A61K31/53A61P31/04
CPCY02A50/30
Inventor 大卫·P·雅各布斯盖伊·艾伦·席泽沈宏明诺曼·P·詹森亚切克·泰尔平斯基
Owner JACOBUS PHARMA CO INC