# US 10,118,926 B2 · Tricyclic quinoline and quinoxaline derivatives

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- Number: US 10,118,926 B2
- Document ID: US10118926B2
- Status: Granted
- Kind: B2
- Application number: 14/026,354
- Filed: 2013-09-13
- Published: 2014-03-20
- Granted: 2018-11-06
- Earliest claimed: 2012-09-14
- Assignees: AbbVie Deutschland GmbH & Co. KG; AbbVie Inc.
- Applicants: AbbVie Deutschland GmbH & Co. KG; AbbVie Inc.
- Inventors: Hannes Koolman; Wilfried Braje; Helmut Mack; Andreas Haupt; Ana Lucia Relo; Karla Drescher; Margaretha Henrica Maria Bakker; Viktor Lakics; Carolin Hoft; Ruxu Xu; Xiaona Zhao
- Web page: https://patentgrep.com/patent/US10118926B2

## CPC

- C07D 471/06: Peri-condensed systems
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 7/12: Antidiuretics, e.g. drugs for diabetes insipidus (ADH A61P5/10)
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 13/10: of the bladder
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 15/10: for impotence
- A61P 15/12: for climacteric disorders
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 17/06: Antipsoriatics
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/06: Antimigraine agents
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/20: Hypnotics; Sedatives
- 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 25/30: for treating abuse or dependence
- A61P 25/32: Alcohol-abuse
- A61P 25/34: Tobacco-abuse
- A61P 25/36: Opioid-abuse
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 487/06: Peri-condensed systems
- C07D 487/16: Peri-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to tricyclic quinoline and quinoxaline derivatives, to a pharmaceutical composition containing such compounds, to their use as modulators, especially agonists or partial agonists, of the 5-HT2C receptor, their use for preparing a medicament for the prevention or treatment of conditions and disorders which respond to the modulation of 5-HT2C receptor, and to a method for preventing or treating conditions and disorders which respond to the modulation of 5-HT2C receptor.

## Claims

### Claim 1

A compound, which is selected from the group consisting of:
4-Ethyl-8,8-dimethyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;
6,8,8-Trimethyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline;
8-Methyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinolin-8-ol;
8-Methoxy-8-methyl-2,3,4,67,8-hexahydro-6H-[1,4]diazepino [6,7,1-ij]quinoline; and
2,8-Dimethyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinolin-8-ol;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A pharmaceutical composition comprising a compound as claimed in claim 1 or a pharmaceutically acceptable salt thereof in combination with at least one pharmaceutically acceptable carrier.

### Claim 3

A compound, which is selected from the group consisting of:
2,3,5,6,7,8-Hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
1-Cyclobutyl-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
1-Methyl-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
1-(Oxetan-3-yl)-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
1-(Cyclopropylmethyl)-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
1-(Cyclopentylmethyl)-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
Cyclopropyl(2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxalin-1-yl)methanone;
Cyclopentyl(2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxalin-1-yl)methanone;
1-Cyclopropyl-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
1-Cyclopentyl-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
1-Cyclopropyl-5-methyl-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
7-Methyl-5,6,7,9,9a,10,11,12-octahydro-4H-[1,4]diazepino[1,7,6-de]pyrrolo[1,2-a]quinoxaline;
1-Fluoro-7-methyl-5,6,7,9,9a,10,11,12-octahydro-4H-[1,4]diazepino[1,7,6-de]pyrrolo[1,2-a]quinoxaline;
1-Cyclopropyl-5,6,7,9,9a,10,11,12-octahydro-4H-[1,4]diazepino[1,7,6-de]pyrrolo[1,2-a]quinoxaline;
1-Cyclobutyl-5,6,7,9,9a,10,11,12-octahydro-4H-[1,4]diazepino[1,7,6-de]pyrrolo[1,2-a]quinoxaline;
1-Cyclopentyl-5,6,7,9,9a,10,11,12-octahydro-4H-[1,4]diazepino[1,7,6-de]pyrrolo[1,2-a]quinoxaline;
4,5,6,7,9,9a,9b,10, 10a,11-Decahydrocyclopropa[3,4]pyrrolo[1,2-a][1,4]diazepino[1,7,6-de]quinoxaline;
1-Ethyl-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
1-Propyl-2,3,5,6,7, 8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
1-Cyclobutyl-5-methyl-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
5-Methyl-1-(oxetan-3 -yl)-2,3,5,6,7, 8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
1-Ethyl-5-methyl-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
5-Methyl-1-propyl-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline; and
1-cyclopentyl-5-methyl-2,3,5,6,7,8-hexahydro-1H-[1,4]diazepino[1,7,6-de]quinoxaline;
or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 3)

A pharmaceutical composition comprising a compound as claimed in claim 3 or a pharmaceutically acceptable salt thereof in combination with at least one pharmaceutically acceptable carrier.

### Claim 5

A compound 4,5,6,7,9,9a,9b,10,10a,11-Decahydrocyclopropa[3,4]pyrrolo[1,2-a][1,4]diazepino[1,7,6-de]quinoxaline; or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 5)

A pharmaceutical composition comprising a compound as claimed in claim 5 or a pharmaceutically acceptable salt thereof-in combination with at least one pharmaceutically acceptable carrier.