Amides of acetic and propionic acids

Patent metadata

Field	Value
Publication number	US-10414762-B2
Application number	US-201815884159-A
Country	US
Kind code	B2
Filing date	Jan 30, 2018
Priority date	Mar 15, 2002
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

The invention relates to novel amides of acetic and propionic acids, methods for production and use thereof for the production of medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration, learning ability and memory.

First claim

The invention claimed is:

1. A method of improving perception, concentration, learning or memory, after a cognitive impairment in a patient in need thereof, comprising administering to the patient a compound selected from the group consisting of:
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-bromo-1-benzothien-2-yl) acetamide hydrochloride;
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl) acetamide hydrochloride;
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-quinolinyl) acetamide hydrochloride;
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(2-naphthyl)acetamide hydrochloride; and
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(8-nitro-2-naphthyl) acetamide hydrochloride.

2. The method of claim 1 , wherein the cognitive impairment is mild cognitive impairment or Alzheimer's disease.

3. The method of claim 1 , wherein the cognitive impairment is schizophrenia or schizophrenia with dementia.

4. The method of claim 1 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-bromo-1-benzothien-2-yl)acetamide hydrochloride.

5. The method of claim 1 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride.

6. The method of claim 1 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-quinolinyl)acetamide hydrochloride.

7. The method of claim 1 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(2-naphthyl)acetamide hydrochloride.

8. The method of claim 1 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(8-nitro-2-naphthyl)acetamide hydrochloride.

9. A method of treating a patient suffering from a cognitive impairment in a patient in need thereof, comprising administering to the patient a compound selected from the group consisting of:
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-bromo-1-benzothien-2-yl)acetamide hydrochloride;
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride;
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-quinolinyl)acetamide hydrochloride;
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(2-naphthyl)acetamide hydrochloride; and
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(8-nitro-2-naphthyl)acetamide hydrochloride,

wherein the cognitive impairment is selected from the group consisting of: mild cognitive impairment, Alzheimer's disease, schizophrenia, and schizophrenia with dementia.

10. The method of claim 9 , wherein the cognitive impairment is mild cognitive impairment or Alzheimer's disease.

11. The method of claim 9 , wherein the cognitive impairment is schizophrenia or schizophrenia with dementia.

12. The method of claim 9 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-bromo-1-benzothien-2-yl)acetamide hydrochloride.

13. The method of claim 9 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride.

14. The method of claim 9 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-quinolinyl)acetamide hydrochloride.

15. The method of claim 9 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(2-naphthyl)acetamide hydrochloride.

16. The method of claim 9 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(8-nitro-2-naphthyl)acetamide hydrochloride.

17. A method of treating a patient suffering from a cognitive impairment in a patient in need thereof, comprising administering to the patient a pharmaceutical composition comprising:
i) a compound selected from the group consisting of:
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-bromo-1-benzothien-2-yl) acetamide hydrochloride;
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl) acetamide hydrochloride;
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-quinolinyl) acetamide hydrochloride;
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(2-naphthyl)acetamide hydrochloride; and
2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(8-nitro-2-naphthyl) acetamide hydrochloride; and
ii) one or more pharmaceutically acceptable carriers or excipients,

wherein the cognitive impairment is selected from the group consisting of: mild cognitive impairment, Alzheimer's disease, schizophrenia, and schizophrenia with dementia.

18. The method of claim 17 , wherein the cognitive impairment is mild cognitive impairment or Alzheimer's disease.

19. The method of claim 17 , wherein the cognitive impairment is schizophrenia.

20. The method of claim 17 , wherein the cognitive impairment is schizophrenia with dementia.

21. The method of claim 17 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-bromo-1-benzothien-2-yl)acetamide hydrochloride.

22. The method of claim 17 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride.

23. The method of claim 17 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(7-quinolinyl)acetamide hydrochloride.

24. The method of claim 17 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(2-naphthyl)acetamide hydrochloride.

25. The method of claim 17 , wherein the compound is 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(8-nitro-2-naphthyl)acetamide hydrochloride.

Assignees

• Bayer Ip Gmbh

Inventors

• Luithle Joachim
• Böβ Frank-Gerhard
• Erb Christina
• Schnizler Katrin
• Flessner Timo
• Van Kampen Marja
• Methfessel Christoph

Classifications

• A61P43/00

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

• A61P25/16

  Anti-Parkinson drugs · CPC title

• A61P25/14

  for treating abnormal movements, e.g. chorea, dyskinesia · CPC title

• A61P25/04

  Centrally acting analgesics, e.g. opioids · CPC title