The present invention relates to the compounds of formula (I): [structure] in which A is a group of formula (a) or (b) [structure] in which R represents a hydrogen or halogen atom, an â€”S(O) z (C 1 -C 4 )alkyl group, an â€”NHSO 2 (C 1 -C 4 )alkyl group, an â€”SO 2 NH(C 1 -C 4 )alkyl group, an â€”NHSO 2 phenyl-(C 1 -C 4 )alkyl group or an â€”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 â€”CO(C 1 -C 4 )alkyl group, a phenyl-(C 1 -C 4 )alkyl group or a â€”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 â€”SO 2 (C 1 -C 4 )alkyl group, an â€”SO 2 phenyl-(C 1 -C 4 )alkyl group or an â€”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 â€”COO(C 1 -C 4 )alkyl group, a â€”CO(C 1 -C 4 )alkyl group, an â€”NHSO 2 (C 1 -C 4 )alkyl group, an â€”NHSO 2 phenyl-(C 1 -C 4 )alkyl groups, â€”NO 2 , â€”CN, â€”CONR 4 R 5 , â€”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

20 · 1 independent · depth 3

20 granted claims

›1.independentA compound of formula (I):+19

›2.↳ 1The compound according to claim 1, in which n and m are each 0.d2

›3.↳ 1The compound according to claim 1, in which R1 is a hydrogen atom.d2

›4.↳ 1The compound according to claim 1, in which R is chosen from an â€”NHSO2(C1-C4)alkyl group, an â€”NHSO2phenyl-(C1-C4)alkyl group or an â€”NHSO2phenyl …d2

›5.↳ 1The compound according to claim 1, in which R3 is â€”CN, â€”COOH, â€”COO(C1-C4)alkyl or â€”CO(C1-C4)alkyl.d2

›6.↳ 1The compound according to claim 1, in which z is 2.d2

›7.↳ 1The compound according to claim 1, wherein X is methylene, ethylene or propylene, or a salt thereof.d2

›8.↳ 1The compound according to claim 1, wherein X is carbonyl, â€”COâ€”COâ€”, â€”COâ€”C((C1-C4)alkyl)2â€”COâ€”, â€”COâ€”CH2â€”, or a methylene monosubstitu…d2

›9.↳ 1The compound according to claim 1, which is ethyl 4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(phenylsulphonylamino)-phenoxy)propylamino)cyclohexyl]benzoate o…d2+2

›10.↳ 1The compound according to claim 1, which is 4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino)phenoxy)propylamino)cyclohexyl]benzoic acid or a…d2+2

›11.↳ 1The compound according to claim 1, which is:nethyl 4-[4-((2S)-3-(4-benzyloxy-3-(methylsulphonylamino)phenoxy)-2-hydroxypropylamino)cyclohexyl]benzoate…d2+2

The compound according to claim 1, which is:nethyl 4-[4-((2S)-3-(4-benzyloxy-3-(methylsulphonylamino)phenoxy)-2-hydroxypropylamino)cyclohexyl]benzoate,ethyl 4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(n-butylsulphonyl-amino)phenoxy)propylamino)cyclohexyl]benzoate,ethyl 4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(benzylsulphonyl-amino)phenoxy)propylamino)cyclohexyl]benzoate,ethyl 4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonyl)-phenoxy)propylamino)cyclohexyl]benzoate,N-[5-[[(2S)-3-((4-(4-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-phenyl)cyclohexyl)amino)-2-hydroxypropyl]oxy]-2-hydroxyphenyl]-methanesulphonamide,4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino)-phenoxy)propylamino)cyclohexyl]-N,N-diethylbenzamide,4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino)-phenoxy)propylamino)cyclohexyl]-N-n-butylbenzamide,4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino)-phenoxy)propylamino)cyclohexyl]benzene,4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino)-phenoxy)propylamino)cyclohexyl]benzonitrile,4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino-phenoxy)propylamino)cyclohexyl]benzamide,ethyl 4-[4-((2S)-2-hydroxy-3-(4-methoxy-3-(methylsulphonyl-amino)phenoxy)propylamino)cyclohexyl]benzoate,ethyl 4-[4-(((2S)-2-hydroxy-3-[(3-(methylsulphonyl)-2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl]oxy)propyl)amino)cyclohexyl]benzoate,ethyl 4-[4-((2S)-2-hydroxy-3-((5-methylsulphonyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-7-yl)oxy)propylamino)cyclohexyl]benzoate,ethyl 4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-chlorophenoxy)-propylamino)cyclohexyl]benzoate,N-[4-[4-((2S)-2-Hydroxy-3-(4-hydroxy-3-methylsulphonylamino-phenoxy)propylamino)cyclohexyl]benzoyl]pyrrolidine,ethyl 4-[4-((2S)-2-hydroxy-3-(4-hydroxyphenoxy)propylamino)-cyclohexyl]benzoate,4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino)-phenoxy)propylamino)cyclohexyl]-1-ethylcarbonylbenzene,tert-butyl 4-[4-((2S)-2-hydroxy-3-(4-hydroxy-3-(methylsulphonylamino)-phenoxy)propylamino)cyclohexyl]benzoate, or4-[4-(((2S)-2-hydroxy-3-[(3-(methylsulphonyl)-2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl]-oxy)propylamino)cyclohexyl]benzamide,

›12.↳ 1A process for preparing a compound of claim 1, whereinn(a) a compound of formula (II):d2

›13.↳ 1A pharmaceutical composition comprising a compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof, together with a …d2

›17.↳ 1A method for delaying preterm birth in a patient in need thereof comprising administering to the patient an effective amount of the compound according…d2

Classifications

9 codes

IPC · International Patent Classification

Section A — Human necessities

A61K31/553

Section C — Chemistry; metallurgy

C07D267/02
C07D263/54
C07C311/01

USPC · US Patent Classification

514/211.6540/491548/217514/375514/534

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Kamal A Saeed

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Type	Document	Date
related publication	US 20080261949 A1	23 Oct 2008

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