# US 7,612,061 B2 · Piperazine compounds

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- Number: US 7,612,061 B2
- Document ID: US7612061B2
- Status: Granted
- Kind: B2
- Application number: 12/291,485
- Filed: 2008-11-10
- Published: 2009-03-19
- Granted: 2009-11-03
- Earliest claimed: 2005-04-08
- Assignees: Les Laboratoires Servier
- Inventors: Jean-Louis Peglion; Aimee Dessinges; Bertrand Goument; Mark Millan; Clotilde Mannoury La Cour
- Web page: https://patentgrep.com/patent/US7612061B2

## CPC

- C07D 313/08: condensed with one six-membered ring
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/08: for nausea, cinetosis or vertigo; Antiemetics
- A61P 1/14: Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A61P 3/04: Anorexiants; Antiobesity agents
- 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 25/18: 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 25/30: for treating abuse or dependence
- 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 211/22: by oxygen atoms
- C07D 213/81: Amides; Imides
- C07D 215/42: attached in position 4
- C07D 243/08: not condensed with other rings
- C07D 249/12: Oxygen or sulfur atoms
- C07D 295/096: with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D 295/155: with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D 311/68: with nitrogen atoms directly attached in position 4
- C07D 319/20: with substituents attached to the hetero ring
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A compound selected from those of formula (I): wherein: R1, R2, R3 and R4, which may be the same or different, each represent an atom or group selected from hydrogen, halogen, alkyl, alkoxy, phenyl and cyano, X represents a bond, an oxygen atom or a group selected from —(CH2)m—, —OCH2— and —NR5—, wherein m represents 1 or 2, and R5 is as defined in the description, Y represents an oxygen atom or a group selected from NR7 and CHR8, wherein R7 and R8 are as defined in the description, Z represents a nitrogen atom or a CH group, n represents 1 or 2, Ak represents an alkylene chain, Ar represents an aryl or heteroaryl group, its optical isomers, and addition salts thereof with a pharmaceutically acceptable acid. Medical products containing the same which are useful in the treatment of conditions requiring a serotonin reuptake inhibitor and/or NK1 antagonist.

## Claims

### Claim 1

A compound selected from those of formula (I):
wherein:
R1, R2, R3 and R4, which may be the same or different, each represent an atom or group selected from hydrogen, halogen, linear or branched C1-C6alkyl, linear or branched C1-C6alkoxy, phenyl and cyano,
X represents a bond, an oxygen atom or a group selected from —(CH2)m—, —OCH2— and —NR5—,
m represents 1 or 2,
R5 represents a hydrogen atom or a group selected from linear or branched C1-C6alkyl, COR6 and CO2R6,
R6 represents a linear or branched C1-C6alkyl group,
Y represents NR7,
R7 represents a hydrogen atom or a group selected from COR9 and linear or branched C1-C6alkyl, the alkyl group being optionally substituted by a 5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl or 2,3-dihydro-1,4-benzodioxin-2-yl group,
R9 represents a group selected from linear or branched C1-C6alkyl and aryl,
Z represents a nitrogen atom,
n represents 2,
Ak represents a linear or branched C1-C6alkylene chain,
Ar represents an aryl group,
its optical isomers, and addition salts thereof with a pharmaceutically acceptable acid,
it being understood that
an aryl group means phenyl, biphenylyl or naphthyl, each of the groups optionally being substituted by one or more identical or different groups selected from halogen, linear or branched C1-C6alkyl, linear or branched C1-C6alkoxy, hydroxy, cyano, linear or branched C1-C6trihaloalkyl and linear or branched C1-C6trihaloalkoxy.

### Claim 2 (depends on 1)

The compound of claim 1, wherein Y represents NH.

### Claim 3 (depends on 1)

The compound of claim 1, wherein X represents a bond, an oxygen atom or a group selected from —OCH2— and —(CH2)m— wherein m represents 1 or 2.

### Claim 4 (depends on 1)

The compound of claim 1, which is selected from trans-1-{2-[(3,5-dibromobenzyl)oxy]-1,2,3,4-tetrahydronaphth-1-yl}-1,4-diazepane, and enantiomers, and addition salts thereof with a pharmaceutically acceptable acid.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

A method for treating a living animal body, including a human, afflicted with a condition selected from depressive states, comprising the step of administering to the living animal body, including a human, an amount of a compound of claim 1 which is effective for alleviation of the condition.