IP Library Granted Patent US 10,487,079
Granted Patent B2
US 10,487,079 · App. 15/907,040 · Granted Nov 26, 2019

Heteroaryl carboxamides

Inventors: Martin Hendrix (Odenthal, DE); Frank-Gerhard Böß (Berkshire, GB); Christina Erb (Wiesbaden, DE); Joachim Krüger (Düsseldorf, DE); Christoph Methfessel (Wuppertal, DE); Rudy Schreiber (Menlo Park, CA); Welf-Burkhard Wiese (Langenfeld, DE); Joachim Luithle (Wülfrath, DE)
Assignee: BAYER INTELLECTUAL PROPERTY GMBH
C07D453/02
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Quick Facts
Patent No.
US 10,487,079
App. No.
15/907,040
Granted
Nov 26, 2019
Kind
B2
Abstract

The invention relates to novel heteroaryl carboxamides, processes for their preparation, and their use for producing medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration, learning and/or memory.

Claims (46)

1. A method of treating a cognitive impairment in a patient in need thereof, comprising administering to the patient a compound selected from the group consisting of:

N-(1-Azabicyclo[2.2.2]oct-3-yl)-6-quinolinecarboxamide hydrochloride;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-phenazinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-7-quinolinecarboxamide hydrochloride;

N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-quinolinecarboxamide hydrochloride;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-ethyl-7-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-ethyl-6-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-methyl-7-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-methyl-6-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-4-methyl-6-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-propyl-6-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-ethyl-4-methyl-6-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-propyl-7-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-ethyl-4-methyl-7-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-4-(tetrahydro-2H-pyran-2-yl)-6-quinoline-carboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-4-(tetrahydro-2H-pyran-2-yl)-7-quinoline-carboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-phenyl-6-quinolinecarboxamide; and

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-phenyl-7-quinolinecarboxamide;

or a salt thereof.

2. The method of claim 1 , wherein the cognitive impairment is Alzheimers disease.

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

4. The method of claim 1 , wherein the method improves perception, concentration, learning, or memory.

5. A method of treating 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:

N-(1-Azabicyclo[2.2.2]oct-3-yl)-6-quinolinecarboxamide hydrochloride;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-phenazinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-7-quinolinecarboxamide hydrochloride;

N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-quinolinecarboxamide hydrochloride;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-ethyl-7-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-ethyl-6-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-methyl-7-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-methyl-6-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-4-methyl-6-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-propyl-6-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-ethyl-4-methyl-6-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-propyl-7-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-ethyl-4-methyl-7-quinolinecarboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-4-(tetrahydro-2H-pyran-2-yl)-6-quinoline-carboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-4-(tetrahydro-2H-pyran-2-yl)-7-quinoline-carboxamide;

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-phenyl-6-quinolinecarboxamide; and

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-phenyl-7-quinolinecarboxamide;

or a salt thereof; and

ii) one or more pharmaceutically acceptable carriers or excipients.

6. The method of claim 5 , wherein the cognitive impairment is Alzheimer's disease.

7. The method of claim 5 , wherein the cognitive impairment is schizophrenia.

8. The method of claim 5 , wherein the method improves perception, concentration, learning, or memory.

Assignments (4)
CHANGE OF NAME Recorded Aug 24, 2018
From: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT
To: BAYER PHARMA AKTIENGESELLSCHAFT
Reel/Frame 046937/0213 →
MERGER Recorded Aug 24, 2018
From: BAYER HEALTHCARE AG
To: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT
Reel/Frame 046944/0361 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2018
From: HENDRIX, MARTIN; BÖSS, FRANK-GERHARD; ERB, CHRISTINA; KRÜGER, JOACHIM; LUITHLE, JOACHIM; METHFESSEL, CHRISTOPH; SCHREIBER, RUDY; WIESE, WELF-BURKHARD
To: BAYER HEALTHCARE AG
Reel/Frame 046699/0849 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2018
From: BAYER PHARMA AKTIENGESELLSCHAFT
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 046700/0131 →
Priority Claims (1)
DE 10156719 · Nov 19, 2001 · national
Continuity (5)
Continuation 14833987 · Aug 24, 2015
Continuation 13544321 · Jul 9, 2012
Continuation 11891527 · Aug 10, 2007
Continuation 10496404
Related Publication 20190040057A1 · Feb 7, 2019