# US 8,569,285 B2 · Dihydrobenzoxathiazepine compounds, a process for their preparation and pharmaceutical compositions containing them

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- Number: US 8,569,285 B2
- Document ID: US8569285B2
- Status: Granted
- Kind: B2
- Application number: 13/200,045
- Filed: 2011-09-15
- Published: 2012-03-22
- Granted: 2013-10-29
- Earliest claimed: 2010-09-16
- Assignees: Les Laboratoires Servier
- Applicants: Alexis Cordi; Patrice Desos; Pierre Lestage; Laurence Danober
- Inventors: Alexis Cordi; Patrice Desos; Pierre Lestage; Laurence Danober
- Web page: https://patentgrep.com/patent/US8569285B2

## CPC

- C07D 291/08: condensed with carbocyclic rings or ring systems
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- 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 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D 419/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of formula (I): wherein R1 represents a hydrogen atom or a heterocyclic, cyano, alkoxycarbonyl, alkylsulphonylaminoalkyl or N-hydroxycarboximidamide group. Medicinal products containing the same which are useful as modulators of the AMPA receptor.

## Claims

### Claim 1

A compound selected from those of formula (I):
wherein R1 represents a hydrogen atom, a cyano group, a linear or branched (C1-C6)alkoxycarbonyl group, a (C1-C6)alkylsulphonylamino-(C1-C6)alkyl group in which the alkyl moieties may each be linear or branched, an N-hydroxycarboximidamide group or a heterocyclic group,
its enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base,
wherein the term “heterocyclic group” means a 5-membered monocyclic aromatic group having one to four hetero atoms which may be the same or different and which are selected from nitrogen, oxygen and sulphur, wherein the heterocyclic group may be optionally substituted by one or more substituents selected from linear or branched (C1-C6)alkyl and linear or branched (C1-C6)polyhaloalkyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 represents a heterocyclic group.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R1 represents a 5-membered monocyclic aromatic heterocyclic group having at least one nitrogen atom, which heterocyclic group may be optionally substituted by one or more substituents selected from linear or branched (C1-C6)alkyl and linear or branched (C1-C6)polyhaloalkyl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R1 represents a pyrrolyl, pyrazolyl, triazolyl, tetrazolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, thiadiazolyl, dithiazolyl or oxadiazolyl group, which groups may be optionally substituted by, one or more substituents selected from linear or branched (C1-C6)alkyl and linear or branched (C1-C6)polyhaloalkyl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R1 represents a thiazolyl or oxadiazolyl group, which groups may be optionally substituted by one or more substituents selected from linear or branched (C1-C6)alkyl and linear or branched (C1-C6)polyhaloalkyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R1 represents a 1,3-thiazolyl or 1,2,4-oxadiazolyl group, which groups may be optionally substituted by one or more substituents selected from linear or branched (C1-C6)alkyl and linear or branched (C1-C6)polyhaloalkyl.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R1 represents a 1,3-thiazolyl or 1,2,4-oxadiazolyl group substituted by a methyl or trifluoromethyl group.

### Claim 8 (depends on 1)

The compound of claim 1, wherein is in the meta position of the phenoxy ring carrying it.

### Claim 9 (depends on 1)

The compound of claim 1, which is selected from:
8-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-3,4-dihydro-2H-5,1,2-benzoxathiazepine 1,1-dioxide;
8-[3-(3-methyl-1,2,4-oxadiazol-5-yl)phenoxy]-3,4-dihydro-2H-5,1,2-benzoxathiazepine 1,1-dioxide;
its enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base.

### Claim 10

A compound selected from those of formula (V):
wherein Hal represents a halogen atom.

### Claim 11 (depends on 1)

A pharmaceutical composition comprising as active ingredient a compound of claim 1 in combination with one or more inert, non-toxic, pharmaceutically acceptable carriers.

### Claim 12 (depends on 1)

A method of treating a condition selected from disorders of memory and cognition that are associated with age, with syndromes of anxiety or depression, with progressive neurodegenerative diseases, with Alzheimer's disease, with Parkinson's disease, with Pick's disease, with Huntington's chorea, with Korsakoff's disease, with schizophrenia, with the sequelae of acute neurodegenerative diseases, with frontal lobe and subcortical dementias, with the sequelae of ischaemia and with the sequelae of epilepsy in a subject in need thereof, comprising administration of an effective amount of a compound of claim 1.

### Claim 13 (depends on 10)

A compound according to claim 10 wherein Hal represents fluorine, chlorine or bromine.