IP Library Granted Patent US 10,414,762
Granted Patent B2
US 10,414,762 · App. 15/884,159 · Granted Sep 17, 2019

Amides of acetic and propionic acids

Inventors: Joachim Luithle (Wulfrath, DE); Frank-Gerhard Böβ (Sunninghill, GB); Christina Erb (Wiesbaden, DE); Katrin Schnizler (Rodenbach, DE); Timo Flessner (Wuppertal, DE); Marja van Kampen (Neu-Lsenburg, DE); Christoph Methfessel (Wuppertal, DE)
Assignee: Bayer Intellectual Property GmbH
C07D453/02A61K31/439C07D453/04
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Quick Facts
Patent No.
US 10,414,762
App. No.
15/884,159
Granted
Sep 17, 2019
Kind
B2
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.

Claims (44)

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.

Assignments (4)
MERGER Recorded Sep 6, 2019
From: BAYER HEALTHCARE AG
To: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT
Reel/Frame 050301/0352 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2019
From: LUITHLE, JOACHIM; BÖSS, FRANK-GERHARD; ERB, CHRISTINA; SCHNIZLER, KATRIN; FLESSNER, TIMO; VAN KAMPEN, MARJA; METHFESSEL, CHRISTOPH
To: BAYER HEALTHCARE AG
Reel/Frame 048851/0410 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2019
From: BAYER PHARMA AKTIENGESELLSCHAFT
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 048851/0451 →
CHANGE OF NAME Recorded Apr 10, 2019
From: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT
To: BAYER PHARMA AKTIENGESELLSCHAFT
Reel/Frame 048853/0775 →
Priority Claims (1)
DE 102 11 416 · Mar 15, 2002 · national
Continuity (6)
Continuation 15229561 · Aug 5, 2016
Continuation 14633985 · Feb 27, 2015
Continuation 13968536 · Aug 16, 2013
Continuation 12494009 · Jun 29, 2009
Continuation 10508106
Related Publication 20190010150A1 · Jan 10, 2019