# US 7,238,693 B2 · Aryl carbamate derivatives, preparation and use thereof

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- Number: US 7,238,693 B2
- Document ID: US7238693B2
- Status: Granted
- Kind: B2
- Application number: 10/467,932
- Filed: 2002-02-22
- Published: 2004-03-25
- Granted: 2007-07-03
- Earliest claimed: 2001-02-23
- Assignees: Cerep SA; Centre National De La Recherche Scientifique; Institut National de la Santa et de la Recherche Medicale (Inserm)
- Inventors: Eric Nicolai; Sophie Curtet; James Sicsic; Frank Lezoualc'h; Rodolphe Fischmeister; Michel Langlois; Magali Maillet; Michèle Launay
- Web page: https://patentgrep.com/patent/US7238693B2

## CPC

- C07D 213/74: Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 13/00: Drugs for disorders of the urinary system
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 213/79: Acids; Esters
- C07D 213/84: Nitriles
- C07D 237/20: Nitrogen atoms (nitro radicals C07D237/12)
- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- C07D 241/20: Nitrogen atoms (nitro radicals C07D241/16)
- C07D 285/10: 1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
- C07D 295/088: to an acyclic saturated chain
- C07D 333/42: with nitro or nitroso radicals directly attached to ring carbon atoms
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/04: 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

The present invention relates to novel compounds, the preparation and use, particularly therapeutic, thereof. More specifically, it relates to compounds derived from aryl carbamates, the preparation and use thereof, particularly in the field of human and animal health. The compounds according to the invention are preferably 5-HT4 serotoninergic receptor ligands and can therefore be used in the therapeutic or prophylactic treatment of any disorder involving a 5-HT4 receptor. The invention also relates to pharmaceutical compositions comprising such compounds, the preparation and use thereof and treatment methods using said compounds. Compounds according to the invention include compounds of the following formula (I):

## Claims

### Claim 1

A compound represented by the general formula (I):
wherein
R1 represents a lower alkyl group,
R2 represents the hydrogen atom,
R3 represents a heterocycle, chosen from among, pyrimidinyl, pyridazinyl or pyrazinyl, such group optionally being substituted by one or more groups chosen from among halogeno, cyano, nitro, alkyl or halogenoalkyl,
Y represents an alkylene bond or chain, linear or branched, having 2 or 3 to 5carbon atoms,
J represents a C—R7 group,
G represents a C—R5 group,
R4, R5, R6 and R7 represent the hydrogen atom,
n is equal to 1, and the salts thereof.

### Claim 2 (depends on 1)

A compound represented by the general formula (I) according to claim 1, wherein R1 represents a methyl or ethyl group.

### Claim 3

A compound chosen from among: 2-[4-(2-pyridinyl)piperazino]ethyl-N-(2-ethoxyphenyl)carbamate 2-[4-(3-pyridazinyl)piperazino]ethyl-N-(2-ethoxyphenyl)carbamate 3-[4-(2-pyridinyl)piperazino]propyl-N-(2-ethoxyphenyl)carbamate 3-[4-(4-pyridinyl)piperazino]propyl-N-(2-ethoxyphenyl)carbamate 3-[4-(3-pyridazinyl)piperazino]propyl-N-(2-ethoxyphenyl)carbamate 3-[4-(4-pyrimidinyl)piperazino]propyl-N-(2-ethoxyphenyl)carbamate 3-[4-(2-pyrimidinyl)piperazino]propyl-N-(2-ethoxyphenyl)carbamate 3-[4-(6-methyl-3-pyridazinyl)piperazino]propyl-N-(2-ethoxyphenyl)carbamate 2-[4-(2-pyridinyl)piperazino]ethyl-N-(2-methoxyphenyl)carbamate 2-[4-(3-pyridazinyl)piperazino]ethyl-N-(2-methoxyphenyl)carbamate 2-[4-(2-pyrimidinyl)piperazino]ethyl-N-(2-methoxyphenyl)carbamate 3-[4-(4-pyridinyl)piperazino]propyl-N-(2-methoxyphenyl)carbamate and the salts thereof.

### Claim 4 (depends on 1, 3)

A pharmaceutical composition comprising a compound according to claim 1 or claim 3.

### Claim 5 (depends on 1)

A method of treatment of urinary incontinence, comprising administering to a subject, particularly human, an effective dose of a compound as defined in claim 1.

### Claim 6 (depends on 1)

A method for preparing a compound according to claim 1, wherein a compound represented by formula (II) is reacted with a compound represented by formula (III):
in which the groups R1, R2, R3, R4, R6, Y, J, G and n are defined as in claim 1, in the presence of a carbonyl donor reagent and the resulting product is recovered.

### Claim 7 (depends on 6)

A method according to claim 6, wherein said carbonyl donor reagent is the (Boc)2O/DMAP system.

### Claim 8 (depends on 6)

A method according to claim 6, wherein a compound represented by formula (II) is reacted with a compound represented by formula (III), in a CXCl2/pyridine system, and the resulting compound is recovered.