# US 9,433,614 B2 · Amides of acetic and propionic acids

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- Number: US 9,433,614 B2
- Document ID: US9433614B2
- Status: Granted
- Kind: B2
- Application number: 14/633,985
- Filed: 2015-02-27
- Published: 2016-01-28
- Granted: 2016-09-06
- Earliest claimed: 2002-03-15
- Assignees: Bayer Intellectual Property GmbH
- Applicants: Bayer Intellectual Property GmbH
- Inventors: Joachim Luithle; Frank-Gerhard Bob; Christina Erb; Katrin Schnizler; Timo Flessner; Marja V. Kampen; Christoph Methfessel
- Web page: https://patentgrep.com/patent/US9433614B2

## CPC

- C07D 453/02: containing not further condensed quinuclidine ring systems
- A61K 31/439: the ring forming part of a bridged ring system, e.g. quinuclidine (8-azabicyclo [3.2.1] octanes A61K31/46)
- A61P 21/02: Muscle relaxants, e.g. for tetanus or cramps
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/02: for peripheral neuropathies
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/16: Anti-Parkinson drugs
- 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
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 453/04: having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## 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

### Claim 1

A method of treating a cognitive impairment in a patient in need thereof, comprising administering to the patient a compound represented by formula (I)
in which
R1 is 1-azabicyclo[2.2.2]oct-3-yl optionally substituted by (C1-C6)-alkyl,
A is methylene or ethylene,
R2 is benzothiophenyl optionally substituted by radicals selected from the group of halogen, formyl, —CO—NR4R5, —CO—OR6, —NR7R8, —NR9—CO—R10, cyano, trifluoromethyl, trifluoromethoxy, nitro, optionally hydroxyl-, amino-, —NH—CO—R11— or cyano-substituted (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkylthio,
in which R4, R5, R6, R7, R8, R9, R10 and R11 are independently of one another hydrogen, (C1-C6)-alkyl, phenyl or benzyl,
and
R3 is hydrogen or (C1-C6)-alkyl,
or a salt thereof.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1, 2)

The method of claim 2, wherein
R1 is 1-azabicyclo[2.2.2]oct-3-yl,
and R2 and R3 have the meaning indicated in claim 1,
or a salt thereof.

### Claim 4 (depends on 3)

The method of claim 3, wherein
A represents a methylene;
R2 represents benzotriazolyl optionally substituted by 1 to 3 radicals selected from the group of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, and
R3 represents hydrogen.

### Claim 5 (depends on 3)

The method of claim 3, where
R1 is 1-azabicyclo[2.2.2]oct-3-yl,
A is methylene,
R2 is benzothiophenyl where the rings are optionally substituted by 1 to 3 radicals selected from the group of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio,
and
R3 is hydrogen,
or a salt thereof.

### Claim 6 (depends on 3)

The method of claim 3, where
R1 is 1-azabicyclo[2.2.2)oct-3-yl,
A is methylene,
R2 is benzothiophenyl, where the rings are optionally substituted by 1 to 2 radicals selected from the group of hydrogen, fluorine, chlorine, bromine, nitro
and
R3 is hydrogen,
or a salt thereof.

### Claim 7

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 represented by formula (I)
in which
R1 is 1-azabicyclo[2.2.2]oct-3-yl optionally substituted by (C1-C6)-alkyl,
A is methylene or ethylene,
R2 is benzothiophenyl optionally substituted by radicals selected from the group of halogen, formyl, —CO—NR4R5, —CO—OR6, —NR7R8, —NR9—CO—R10, cyano, trifluoromethyl, trifluoromethoxy, nitro, optionally hydroxyl-, amino-, —NH—CO—R11— or cyano-substituted (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkylthio,
in which R4, R5, R6, R7, R8, R9, R10 and R11 are independently of one another hydrogen, (C1-C6)-alkyl, phenyl or benzyl,
and
R3 is hydrogen or (C1-C6)-alkyl,
or a salt thereof; and
ii) one or more pharmaceutically acceptable carriers or excipients.

### Claim 8 (depends on 7)

The method of claim 7, wherein the cognitive impairment is Alzheimer's disease.

### Claim 9 (depends on 7, 8)

The method of claim 8, wherein
R1 is 1-azabicyclo[2.2.2]oct-3-yl,
and R2 and R3 have the meaning indicated in claim 7,
or a salt thereof.

### Claim 10 (depends on 9)

The method of claim 9, wherein
A represents a methylene;
R2 represents benzotriazolyl optionally substituted by 1 to 3 radicals selected from the group of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, and
R3 represents hydrogen.

### Claim 11 (depends on 9)

The method of claim 9, where
R1 is 1-azabicyclo[2.2.2]oct-3-yl,
A is methylene,
R2 is benzothiophenyl, where the rings are optionally substituted by 1 to 3 radicals selected from the group of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio,
and
R3 is hydrogen,
or a salt thereof.

### Claim 12 (depends on 9)

The method of claim 9, where
R1 is 1-azabicyclo[2.2.2)oct-3-yl,
A is methylene,
R2 is benzothiophenyl, where the rings are optionally substituted by 1 to 2 radicals selected from the group of hydrogen, fluorine, chlorine, bromine, nitro
and
R3 is hydrogen,
or a salt thereof.