Amide compound and pharmaceutical comprising same

Patent metadata

Field	Value
Publication number	US-9796677-B2
Application number	US-201415100866-A
Country	US
Kind code	B2
Filing date	Dec 9, 2014
Priority date	Dec 10, 2013
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

Provided is a novel compound which has an excellent Aβ aggregation inhibitory effect and is useful as a pharmaceutical. An amide compound represented by the formula (1) or a salt thereof, wherein Z represents CH or N; A and B are the same or different and each represents —CH 2 —, —O—, —S—, or —NH—; R 1 and R 2 are the same or different and each represents a branched alkyl group, a branched alkenyl group, an optionally substituted aromatic hydrocarbon group, an optionally substituted aralkyl group, an optionally substituted cycloalkyl group, or an optionally substituted aromatic heterocyclic group; and R 3 represents a branched alkyl group, a branched alkenyl group, an optionally substituted cycloalkyl group, or an optionally substituted aralkyl group.

First claim

The invention claimed is:

1. An amide compound represented by the formula (1) or a salt thereof:

wherein
Z represents CH or N;
A and B are the same or different and each represents —CH 2 —, —O—, —S—, or —NH—;
R 1 and R 2 are the same or different and each represents a branched alkyl group, a branched alkenyl group, an optionally substituted aromatic hydrocarbon group, an optionally substituted aralkyl group, an optionally substituted cycloalkyl group, or an optionally substituted aromatic heterocyclic group; and
R 3 represents a branched alkyl group, a branched alkenyl group, an optionally substituted cycloalkyl group, or an optionally substituted aralkyl group.

2. The amide compound according to claim 1 or a salt thereof, wherein A and B are the same or different and each is or —CH 2 — or —O—.

3. The amide compound according to claim 1 or a salt thereof, wherein A is —CH 2 — or —O—, and B is —CH 2 —.

4. The amide compound according to claim 1 or a salt thereof, wherein A is —O—, and B is —CH 2 —.

5. The amide compound according to claim 1 or a salt thereof, wherein R 1 and R 2 are the same or different and each is a branched alkyl group having 3 to 12 carbon atoms, a branched alkenyl group having 3 to 12 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 14 carbon atoms, an optionally substituted aralkyl group having 7 to 18 carbon atoms, or an optionally substituted cycloalkyl group having 3 to 12 carbon atoms; and R 3 is a branched alkyl group having 3 to 12 carbon atoms, a branched alkenyl group having 3 to 12 carbon atoms, an optionally substituted cycloalkyl group having 3 to 12 carbon atoms, or an optionally substituted aralkyl group having 6 to 18 carbon atoms.

6. The amide compound according to claim 1 or a salt thereof, wherein R 1 and R 2 are the same or different and each is an optionally substituted aromatic hydrocarbon group having 6 to 14 carbon atoms, an optionally substituted aralkyl group having 7 to 18 carbon atoms, or an optionally substituted cycloalkyl group having 3 to 12 carbon atoms; and R 3 is a branched alkyl group having 3 to 12 carbon atoms, a branched alkenyl group having 3 to 12 carbon atoms, an optionally substituted cycloalkyl group having 3 to 12 carbon atoms, or an optionally substituted aralkyl group having 6 to 18 carbon atoms.

7. The amide compound according to claim 1 or a salt thereof, wherein R 1 and R 2 are the same or different and each is a branched alkyl group having 3 to 12 carbon atoms, a branched alkenyl group having 3 to 12 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 14 carbon atoms, an optionally substituted aralkyl group having 7 to 18 carbon atoms, or an optionally substituted cycloalkyl group having 3 to 12 carbon atoms; and R 3 is a branched alkyl group having 3 to 12 carbon atoms, a branched alkenyl group having 3 to 12 carbon atoms, an optionally substituted cycloalkyl group having 3 to 12 carbon atoms, or an optionally substituted aralkyl group having 6 to 18 carbon atoms, wherein the group(s) capable of substituting the aromatic hydrocarbon group, the aralkyl group, or the cycloalkyl group is 1 to 5 groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a hydroxy group, a halogen atom, a nitro group, an amino group, a mono-C 1-4 alkylamino group, a di-C 1-4 alkylamino group, and a halogeno-C 1-4 alkyl group.

8. The amide compound according to claim 1 or a salt thereof, wherein R 1 and R 2 are the same or different and each is an optionally substituted aromatic hydrocarbon group having 6 to 14 carbon atoms, an optionally substituted aralkyl group having 7 to 18 carbon atoms, or an optionally substituted cycloalkyl group having 3 to 12 carbon atoms; and R 3 is a branched alkyl group having 3 to 12 carbon atoms, a branched alkenyl group having 3 to 12 carbon atoms, an optionally substituted cycloalkyl group having 3 to 12 carbon atoms, or an optionally substituted aralkyl group having 6 to 18 carbon atoms, wherein the group(s) capable of substituting the aromatic hydrocarbon group, the aralkyl group, or the cycloalkyl group is 1 to 5 groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a hydroxy group, a halogen atom, a nitro group, an amino group, a mono-C 1-4 alkylamino group, a di-C 1-4 alkylamino group, and a halogeno-C 1-4 alkyl group.

9. The amide compound according to claim 1 or a salt thereof, which is

10. The amide compound according to claim 1 or a salt thereof, which is

11. A pharmaceutical composition comprising an amide compound according to claim 1 or a salt thereof and a pharmaceutically acceptable carrier.

12. A pharmaceutical composition comprising the amide compound according to claim 2 or a salt thereof and a pharmaceutically acceptable carrier.

13. A pharmaceutical composition comprising the amide compound according to claim 3 or a salt thereof and a phaiiiiaceutically acceptable carrier.

14. A pharmaceutical composition comprising the amide compound according to claim 4 or a salt thereof and a phaiiiiaceutically acceptable carrier.

15. A pharmaceutical composition comprising the amide compound according to claim 5 or a salt thereof and a phaiiiiaceutically acceptable carrier.

16. A pharmaceutical composition comprising the amide compound according to claim 6 or a salt thereof and a pharmaceutically acceptable carrier.

17. A pharmaceutical composition comprising the amide compound according to claim 7 or a salt thereof and a pharmaceutically acceptable carrier.

18. A pharmaceutical composition comprising the amide compound according to claim 8 or a salt thereof and a pharmaceutically acceptable carrier.

19. A pharmaceutical composition comprising the amide compound according to claim 9 or a salt thereof and a pharmaceutically acceptable carrier.

20. A pharmaceutical composition comprising the amide compound according to claim 10 or a salt thereof and a pharmaceutically acceptable carrier.

Assignees

• Japan Science & Tech Agency

Inventors

• Kanai Motomu
• Soma Yohei
• Arai Tadamasa
• Araya Takushi

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• C07D239/30

  Halogen atoms or nitro radicals · 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

• C07D213/81 Primary

  Amides; Imides · CPC title