Novel 1,3-selenazolin derivatives and process for preparing the same

• US 20030158239A1
• Filed: 12/13/2002
• Published: 08/21/2003
• Est. Priority Date: 12/25/2001
• Status: Active Grant

• Current Assignee: GIFU University
• Original Assignee: GIFU University
• Inventors: Koketsu, Mamoru, Ishihara, Hideharu
• Granted Patent: US 7,176,164 B2
• Time in Patent Office: Days
• US Class Current: 514/359
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/28 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 Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 39/06 Free radical scavengers or antioxidants
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 293/06 Selenazoles; Hydrogenated selenazoles

Abstract

A process for preparing novel 1,3-selanazolin derivatives represented by chemical formula 1 at high yield. This process includes a step of reacting a selenourea and an α-haloacyl halide in a solvent and in the presence of a catalyst.

Claims

1. 1,3-Selenazolin derivatives represented by the following chemical formula 1,

2. The 1,3-selenazolin derivatives according to claim 1, wherein in the chemical formula 1, R₁, R₂, R₃ and R₄ each denote hydrogen, alkyl group having 2 to 8 carbon atoms, cycloalkyl group having 2 to 8 carbon atoms, and aryl group having 2 to 8 carbon atoms.

3. A process for preparing 1,3-selenazolin derivatives comprising a step of reacting a selenourea represented by the following chemical formula 2 and an α

-haloacyl halide represented by the following chemical formula 3 in a solvent and in the presence of a catalyst,

4. The preparation process according to claim 3, wherein R₁ and R₂ in the chemical formula 2 each denote one of hydrogen, alkyl group having 2 to 8 carbon atoms, cycloalkyl group having 2 to 8 carbon atoms and aryl group having 2 to 8 carbon atoms.

5. The preparation process according to claim 3, wherein the halogen is chlorine or bromine.

6. The preparation process according to claim 3, wherein the molar ratio of the α

-haloacyl halide to the selenourea is 1;

1.5 to 1;

2.

7. The preparation process according to claim 3, wherein the reaction step is carried out at a reaction temperature of −

100 to 30 degrees Celsius.

8. The preparation process according to claim 3, wherein the selenourea is a compound selected from the group consisting of N,N′

-diisopropyl selenourea, N,N′

-cyclohexyl selenourea, N,N′

-4-methylphenyl selenourea N,N′

-t-butyl selenourea and N,N′

-2-methylphenyl selenourea, and wherein the α

-haloacyl halide is a compound selected from the group consisting of chloroacetyl chloride, chloromethylacetyl chloride, bromoethylacetyl bromide, bromodimethylacetyl bromide and chlorophenylacetyl chloride.

9. The preparation process according to claim 3, wherein the reaction step includes reacting the selenourea, the α

-haloacyl halide and the catalyst at a time.

10. The preparation process according to claim 3, wherein the reaction step includes:

a first step of reacting the selenourea and the α

-haloacyl halide in a solvent, and

a second step of adding the catalyst followed by the further reaction of the selenourea and the α

-haloacyl halide.

11. The preparation process according to claim 3, wherein the catalyst is a catalyst selected from a metal catalyst, Lewis acid catalyst, basic catalyst and enzyme.

12. A medicament containing 1,3-Selenazolin derivatives represented by the following chemical formula 1,

13. An agricultural chemical composition containing 1,3-Selenazolin derivatives represented by the following chemical formula 1,