Furoxan compound, and manufacturing method for same

Patent metadata

Field	Value
Publication number	US-10053435-B2
Application number	US-201515543547-A
Country	US
Kind code	B2
Filing date	Dec 15, 2015
Priority date	Jan 14, 2015
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

The present invention provides: a furoxan compound having a fluorine atom as a substituent group on the ring structure thereof; and a novel nitric oxide donor including the compound. The present invention relates to a fluorofuroxan compound represented by general formula (1) or (2). The compound of formula (1) can be manufactured by reacting a fluoride salt with a nitrofuroxan compound to substitute the nitro group with a fluoro group. The compound of formula (2) can be manufactured by subjecting the compounds of formula (1) to isomerization by irradiation with light.

First claim

The invention claimed is:

1. A fluorofuroxan compound represented by general formula (1) or (2) below:

in each formula, R 1 represents a hydroxyl group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, an aryl group having 4 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, an alkynyloxy group having 2 to 30 carbon atoms, an aryloxy group having 4 to 30 carbon atoms, an alkylsulfonyl group having 1 to 30 carbon atoms, an alkenylsulfonyl group having 2 to 30 carbon atoms, an alkynylsulfonyl group having 2 to 30 carbon atoms, an arylsulfonyl group having 4 to 30 carbon atoms, an acyl group having 1 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, an aryloxycarbonyl group having 4 to 30 carbon atoms, a thiocarbonyl group, a carboxyl group, an amino group, a monoalkylamino group having 1 to 30 carbon atoms, a dialkylamino group having 2 to 30 carbon atoms, a monoarylamino group having 4 to 30 carbon atoms, a diarylamino group having 8 to 30 carbon atoms, a carbonylamino group, a sulfonylamino group, a cyano group, a nitro group, an alkylsulfinyl group having 1 to 30 carbon atoms, an arylsulfinyl group having 4 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, an arylthio group having 4 to 30 carbon atoms, a phosphoryl group, a dialkylaminocarbonyl group having 2 to 30 carbon atoms, or a monoalkylaminocarbonyl group having 1 to 30 carbon atoms.

2. A nitric oxide donor comprising the fluorofuroxan compound according to claim 1 .

3. A method for manufacturing the fluorofuroxan compound represented by general formula (1) according to claim 1 , the method comprising a step of reacting a nitrofuroxan compound represented by general formula (3) below with a fluoride salt to substitute a nitro group with a fluoro group:

wherein R 1 is the same as R 1 defined in claim 1 .

4. A method for manufacturing the fluorofuroxan compound represented by general formula (2) according to claim 1 , the method comprising a step of isomerizing the fluorofuroxan compound represented by general formula (1) according to claim 1 by irradiation with light:

wherein R 1 is the same as R 1 defined in claim 1 .

5. The fluorofuroxan compound according to claim 1 ,
wherein R 1 represents an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, or an aryl group having 4 to 30 carbon atoms.

6. The fluorofuroxan compound according to claim 1 ,
wherein R 1 represents an aryl group having 4 to 30 carbon atoms.

Assignees

• Univ Kobe Nat Univ Corp

Inventors

• Matsubara Ryosuke
• Ando Akihiro
• Hayashi Masahiko

Classifications

• A61P9/10

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• A61P35/00

  Antineoplastic agents · CPC title

• A61P25/28

  for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia · CPC title

• A61P25/08

  Antiepileptics; Anticonvulsants · CPC title

• C07D271/08 Primary

  1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles · CPC title