# US 6,720,342 B2 · Heterocyclic compounds and their preparation and use

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- Number: US 6,720,342 B2
- Document ID: US6720342B2
- Status: Granted
- Kind: B2
- Application number: 09/940,963
- Filed: 2001-08-28
- Published: 2002-08-22
- Granted: 2004-04-13
- Earliest claimed: 1996-03-19
- Assignees: Novo Nordisk A/S
- Inventors: Lone Jeppesen; Per Sauerberg
- Web page: https://patentgrep.com/patent/US6720342B2

## CPC

- C07D 487/08: Bridged systems
- A61P 13/00: Drugs for disorders of the urinary system
- A61P 13/10: of the bladder
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/02: for peripheral neuropathies
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/22: Anxiolytics
- 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 27/00: Drugs for disorders of the senses
- A61P 27/06: Antiglaucoma agents or miotics
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to therapeutically active azabicyclic compounds, a method of preparing the same and to pharmaceutical or veterinary compositions comprising the compounds. The novel compounds are useful in treating a disease in the central nervous system caused by malfunctioning of the muscarinic cholinergic system.

## Claims

### Claim 1

A compound of formula I or the quaternized form thereof:
wherein
W is oxygen or sulphur;
R is —OR4, —SR4, —SOR4, —SO2R4, or R4, wherein R4 is propynyl substituted with phenoxy, wherein the phenoxy is optionally substituted with one or more halogen(s), —OH, —NO2, —CN, C1-4-alkyl, C1-4-alkylthio, C1-4-alkoxy, —SCF3, —OCF3, —CF3, —CONH2 or —CSNH2;
r is 0, 1 or 2; and
G is an azabicyclic ring system which is:
wherein the thiadiazole ring is attached at any appropriate position;
R1 and R2 independently are hydrogen, —OH, ═O, C1-15-alkyl, C2-15-alkenyl, C2-15-alkynyl, C1-10-alkoxy, and C1-5-alkyl substituted with one or more halogen(s), —OH, —COR8, —CH2OH, —NH2, carboxy and phenyl;
R8 is hydrogen, or C1-6-alkyl;
· · · is a single or double bond;
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 2 (depends on 1)

A compound of claim 1, wherein G is saturated.

### Claim 3 (depends on 1)

A compound of claim 1, wherein G is
and wherein the —(CH2)r—W-thiadiazole is attached to the 3- or 4-position of G.

### Claim 4 (depends on 1)

A compound of claim 1 wherein G is

### Claim 5 (depends on 1)

A compound of claim 1 wherein r is 0.

### Claim 6 (depends on 1)

A compound of claim 1 wherein W is oxygen.

### Claim 7 (depends on 1)

A compound of claim 1 wherein R4 is 2-propyn-1-yl.

### Claim 8 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1 together with one or more pharmaceutical acceptable carriers or diluents.

### Claim 9 (depends on 8)

The pharmaceutical composition of claim 8, wherein said dosage unit comprises from about 0.1 to about 100 mg of the compound.

### Claim 10 (depends on 1)

A method of treating a disease in the central nervous system caused by malfunctioning of the muscarinic cholinergic system comprising administering to a subject in need thereof a pharmaceutically effective amount of a compound of claim 1.