US 2012/0252784 A1 · 2,3,4-BENZOTHIADIAZEPINE-2,2-DIOXIDE DERIVATIVES

2,3,4-benzothiadiazepine-2,2-dioxide derivatives

OwnerJozsef FETTER, Ferenc BERTHA +13inventors

InventorsJozsef FETTER, Ferenc BERTHA, Balazs MOLNAR, Gyula SIMIG, Jozsef BARKOCZY, Balazs VOLK, Gyoergy LEVAY, Istvan GACSALYI, Gabor GIGLER, Hajnalka KOMPAGNE, Bernadett MARKO, Katalin NAGY, Peter KIRICSI, Laszlo Gabor HARSING, Gabor SZENASI

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Abstract

Novel 2,3,4-benzothiadiazepines-2,2-dioxides and processes for the preparation thereof are disclosed. The compounds influence the central nervous system and may be used to treat or prevent Alzheimer's disease, Parkinson's disease or Huntington's disease, senile dementia not of the Alzheimer's type, vascular dementia, post-stroke dementia, Korsakoff's syndrome, Down's syndrome, schizophrenia, panic disorder, post-traumatic stress disorder, anxiety or depression.

Claims17

Dependent claims

Compounds of the general Formula (I), wherein

‘a’ represents single or double bond,
R1 and R2 represent, independently, hydrogen, halogen, cyano group, C1-6 alkyl group, C1-6 alkoxy group trifluoromethyl group or other C1-6 alkyl group substituted by one or more halogen atom
or if
‘a’ represents single bond,
R1 and R2 together form a group of the formula ═N—S—N═ attached to the atoms of the bond ‘a’ according to the partial Formula (A)
R3 and R4 represents, independently, hydrogen C1-6 alkyl group, C1-6 alkenyl group, C3-6 cycloalkyl group, C1-6 aryl group or C1-6 aralkyl group,
R5 and R6 represents, independently, hydrogen, halogen, cyano group, C1-6 alkyl group, C1-6 alkoxy group, trifluoromethyl group or other C1-6 alkyl group substituted by one or more halogen atom
enantiomers and pharmaceutically suitable acid addition salts thereof.

5 more elements

A compound selected from

8-cyano-5-(4-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-chloro-5-(3-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide,
9-(4-methyl-phenyl)-5H,7H-[1,2,5]thiadiazolo[3,4-h]-2,3,4-benzothiadiazepine-6,6-dioxide;
9-(4-methoxy-phenyl)-5H,7H-[1,2,5]thiadiazolo[3,4-h][2,3,4]benzothiadiazepine-6,6-dioxide;
9-(3,4-dimethoxy-phenyl)-5H,7H-[1,2,5]thiadiazolo[3,4-h][2,3,4]benzothiadiazepine-6,6-dioxide;
9-(4-fluoro-phenyl)-5H,7H-[1,2,5]thiadiazolo[3,4-h][2,3,4]benzothiadiazepine-6,6-dioxide;
7-chloro-5-(4-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepien-2,2-dioxide;
7-fluoro-5-(4-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7,8-dichloro-5-(4-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-chloro-5-(4-fluoro-phenyl)-3-methyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-chloro-3-ethyl-5-(4-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-chloro-5-(4-fluoro-phenyl)-3-propyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-chloro-5-(4-fluoro-phenyl)-3-(prop-2-inyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-chloro-5-(4-fluoro-phenyl)-3-isopropyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-chloro-5-(4-fluoro-phenyl)-3-(3-methyl-but-2-enyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-chloro-5-(4-fluoro-phenyl)-3-(3-methyl-butyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
3-benzyl-7-chloro-5-(4-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-fluoro-5-(4-fluoro-phenyl)-3-methyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-fluoro-3-ethyl-5-(4-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
3-butyl-7-fluoro-5-(4-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-fluoro-5-(4-fluoro-phenyl)-3-(3-methyl-but-2-enyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-fluoro-5-(4-fluoro-phenyl)-3-(3-methyl-butyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-fluoro-5-(4-fluoro-phenyl)-3-hexyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
3-benzyl-7-fluoro-5-(4-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-fluoro-5-(4-fluoro-phenyl)-3-(3-phenyl-propyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
5-(3-fluoro-phenyl)-7-chloro-3-methyl-1-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
8-cyano-5-(4-fluoro-phenyl)-3-methyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
8-fluoro-5-(4-fluoro-phenyl)-3-methyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
5-(4-fluoro-phenyl)-8-chloro-3-methyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
5-(4-fluoro-phenyl)-3-methyl-8-trifluormethyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7,8-dichloro-5-(4-fluoro-phenyl)-3-methyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
9-(4-fluoro-phenyl)-7-methyl-5H,7H-[1,2,5]thiadiazolo[3,4-h][2,3,4]benzothiadiazepine-6,6-dioxide;
7,8-dichloro-3-ethyl-5-(4-fluoro-phenyl)-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-chloro-5-(4-fluoro-phenyl)-1,3-dimethyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide;
7-chloro-1-ethyl-5-(4-fluoro-phenyl)-3-methyl-1,3-dihydro-2,3,4-benzothiadiazepine-2,2-dioxide
and/or enantiomers and/or pharmaceutically acceptable acid addition salts thereof.

33 more elements

Dependencies are inferred from the claim text.

Facts

Application

13/418,869Filed 13 Mar 2012

Priority

HU P090061629 Sep 2009

Published

4 Oct 2012

Term ends

Not estimatedThe source records don’t support an estimate.

Classification13 codes

C07D 285/36
Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 -…:…
A61P 25/00
Drugs for disorders of the nervous system
A61P 25/16
For treating abnormal movements, e.g. chorea, dyskinesia: anti-Parkinson drugs
A61P 25/18
Drugs for disorders of the nervous system: antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia