IP Library Granted Patent US 7,388,031
Granted Patent B2
US 7,388,031 · App. 10/432,493 · Granted Jun 17, 2008

Cyclohexyl(alkyl)-propanolamines, preparation method and pharmaceutical compositions containing same

Assignee: Sanofi-Aventis
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Quick Facts
Patent No.
US 7,388,031
App. No.
10/432,493
Granted
Jun 17, 2008
Kind
B2
Abstract

The present invention relates to the compounds of formula (I): in which A is a group of formula (a) or (b) in which R represents a hydrogen or halogen atom, an —S(O) z (C 1 –C 4 )alkyl group, an —NHSO 2 (C 1 –C 4 )alkyl group, an —SO 2 NH(C 1 –C 4 )alkyl group, an —NHSO 2 phenyl-(C 1 –C 4 )alkyl group or an —NHSO 2 phenyl group, said phenyl possibly being substituted with a halogen atom, with a (C 1 –C 4 )alkyl group or with a (C 1 –C 4 )alkoxy group; R 1 represents a hydrogen atom or a (C 1 –C 4 )alkyl group, a —CO(C 1 –C 4 )alkyl group, a phenyl-(C 1 –C 4 )alkyl group or a —COphenyl group, said phenyl also possibly being substituted with a halogen atom or with a (C 1 –C 4 )alkoxy group; R 2 is a hydrogen atom or an —SO 2 (C 1 –C 4 )alkyl group, an —SO 2 phenyl-(C 1 –C 4 )alkyl group or an —SO 2 phenyl group; X completes a ring of 5 to 8 atoms, said ring being saturated or unsaturated, possibly being substituted with one or two (C 1 –C 4 )alkyl groups and bearing one or two carbonyl groups; n, m and z are, independently, 0, 1 or 2; R 3 represents a hydrogen or halogen atom, a (C 1 –C 6 )alkyl group, a (C 1 –C 4 )alkoxy group, a —COO(C 1 –C 4 )alkyl group, a —CO(C 1 –C 4 )alkyl group, an —NHSO 2 (C 1 –C 4 )alkyl group, an —NHSO 2 phenyl-(C 1 –C 4 )alkyl groups, —NO 2 , —CN, —CONR 4 R 5 , —COOH, or a 4,5-dihydro-1,3-oxazol-2-yl or 4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl group; R 4 and R 5 represent, independently, a hydrogen atom, a phenyl, a (C 1 –C 4 )alkyl group or a phenyl-(C 1 –C 4 )alkyl group or R 4 and R 5 with the nitrogen atom to which they are attached, may form a ring of 5 to 7 atoms in total; and to the salts or solvates thereof, to the pharmaceutical compositions containing them, to a process for the preparation thereof and to intermediates in this process.

Claims (9)

1. A compound, which is ethyl 4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino)phenoxy)propylamino)cyclohexyl]benzoate or a salt or solvate thereof.

2. A process for preparing the compound according to claim 1 , wherein

(a) a compound of formula (II):

wherein A is 4-hydroxy-3(methylsulphonylamino)-phenyl is reacted with an amine of formula (III):

wherein n is O, m is O and R 3 is ethoxycarbonyl attached to the para position of the phenyl ring, and optionally, the compound according to claim 1 thus obtained is transformed into a salt or solvate thereof.

3. A pharmaceutical composition comprising the compound according to claim 1 or a pharmaceutically acceptable salt or solvate thereof, together with a pharmaceutical excipient.

4. A method for delaying preterm birth in a patient in need thereof comprising administering to the patient an effective amount of the compound according to claim 1 or a salt of solvate thereof.

5. The compound according to claim 1 , which is trans-ethyl 4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino)phenoxy)propylamino) cyclohexyl]benzoate or a salt or solvate thereof.

6. The salt according to claim 5 , which is trans-ethyl 4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino)phenoxy)propylamino) cyclohexyl]benzoate hydrochlorate.

Assignments (6)
CHANGE OF NAME Recorded Jun 20, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028413/0927 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED ON REEL 020226 FRAME 0978. ASSIGNOR(S) HEREBY CONFIRMS THE CORRECT ASSIGNEE ADDRESS SHOULD BE 174 AVENUE DE FRANCE, PARIS, FRANCE 75013. Recorded Jan 11, 2008
From: SANOFI-SYNTHELABO
To: SANOFI-AVENTIS
Reel/Frame 020352/0229 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2007
From: BOVY, PHILIPPE R.; CECCHI, ROBERTO; COURTEMANCHE, GILLES; CROCI, TIZIANO; OLIVA, AMBROGIO; VIVIANI, NUNZIA
To: SANOFI-SYNTHELABO
Reel/Frame 020226/0841 →
CHANGE OF NAME Recorded Dec 11, 2007
From: SANOFI-SYNTHELABO
To: SANOFI-AVENTIS
Reel/Frame 020226/0978 →
CHANGE OF NAME Recorded Jul 22, 2005
From: SANOFI-SYNTHELABO
To: SANOFI-AVENTIS
Reel/Frame 016345/0189 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 21, 2003
From: BOVY, PHILIPPE, R.; CECCHI, ROBERTO; COURTEMANCHE, GILLES; CROCI, TIZIANO; OLIVA, AMBROGIO; VIVIANI, NUNZIA
To: SANOFI-SYNTHELABO
Reel/Frame 014606/0464 →
Priority Claims (1)
FR 00 15477 · Nov 30, 2000 · national
Continuity (1)
Related Publication 20040053916A1 · Mar 18, 2004