Heterocyclic compounds
AssigneeAdir et Compagnie
InventorsDaniel Lesieur, Nicolas Ruiz, Valerie Wallez, Sophie Boye, Caroline Bennejean, Pierre Renard, Philippe Delagrange
Life of this patent
Estimating the term…
Abstract
Compound of formula (I): ##STR1## wherein: B represents optionally substituted (C.sub.1 -C.sub.6)-alkylene, W represents oxygen or sulphur, R represents hydrogen, hydroxy, R', or OR', R' being as defined in the description, G.sub.1 and G.sub.11 are as defined in the description, G.sub.2 represents a group selected from: ##STR2## wherein R.sub.20, R.sub.21, and R.sub.2 are as defined in the description, and medicinal products containing the same which are useful as melatoninergic ligands.
Claims23
A compound selected from those of formula (I):
- ##STR27## wherein:
- the 2-3 bond is saturated or unsaturated
- W represents oxygen or sulphur,
- B represents linear or branched (C.sub.1 -C.sub.6)-alkylene optionally substituted by one or more linear or branched (C.sub.1 -C.sub.6)-alkyl, hydroxy, linear or branched (C.sub.1 -C.sub.6)-alkoxy, carboxy, or linear or branched (C.sub.1 -C.sub.6)-alkoxycarbonyl,
- R represents hydrogen, hydroxy, R' or OR', R', representing optionally substituted linear or branched (C.sub.1 -C.sub.6)-alkyl, optionally substituted linear or branched (C.sub.2 -C.sub.6)-alkenyl, optionally substituted linear or branched (C.sub.2 -C.sub.6)-alkynyl, optionally substituted (C.sub.3 -C.sub.7)-cycloalkyl, linear or branched (C.sub.1 -C.sub.6)-trihaloalkylsulphonyl, optionally substituted aryl, optionally substituted biphenyl, or optionally substituted heteroaryl,
- G.sub.1 represents halogen, linear or branched (C.sub.1 -C.sub.6)-trihaloalkylsulphonyloxy, carboxy, formyl, cyano, R.sub.1, --CO--R.sub.1 or --O--CO--R.sub.1, R.sub.1 representing an optionally substituted linear or branched (C.sub.1 -C.sub.6)-alkyl, optionally substituted linear or branched (C.sub.2 -C.sub.6)-alkenyl, optionally substituted linear or branched (C.sub.2 -C.sub.6)-alkynyl, optionally substituted (C.sub.3 -C.sub.7)-cycloalkyl, optionally substituted aryl, optionally substituted biphenyl, or optionally substituted heteroaryl,
- in which case G.sub.11 represents hydrogen or G.sub.11 and R form together with the carbon atoms carrying them a ring having to 7 members that is saturated or unsaturated and contains oxygen, that ring optionally being substituted by one or more groups selected from linear or branched (C.sub.1 -C.sub.6)-alkyl, linear or branched (C.sub.1 -C.sub.6)-alkoxy, hydroxy, oxo, carboxy, and linear or branched (C.sub.1 -C.sub.6)-alkoxycarbonyl,
- or
- G.sub.1 represents hydrogen, in which case G.sub.11 represents linear or branched (C.sub.1 -C.sub.6)-trihaloalkylsulphonyloxy, carboxy, formyl, cyano, R.sub.1, --CO--R.sub.1, or --O--CO--R.sub.1, R.sub.1 representing optionally substituted linear or branched (C.sub.1 -C.sub.6)-alkyl, optionally substituted linear or branched (C.sub.2 -C.sub.6)-alkenyl, optionally substituted linear or branched (C.sub.2 -C.sub.6)-alkynyl, optionally substituted (C.sub.3 -C.sub.7)-cycloalkyl, optionally substituted aryl, optionally substituted biphenyl or optionally substituted heteroaryl,
- G.sub.2 represents a group selected from:
- ##STR28## wherein:
- X represents oxygen or sulphur,
- R.sub.2 represents hydrogen or linear or branched (C.sub.1 -C.sub.6)-alkyl,
- R.sub.20, R.sub.21 and R.sub.22 each represents optionally substituted linear or branched (C.sub.1 -C.sub.6)-alkyl, optionally substituted linear or branched (C.sub.2 -C.sub.6)-alkenyl, optionally substituted linear or branched (C.sub.2 -C.sub.6)-alkynyl, optionally substituted (C.sub.3 -C.sub.7)-cycloalkyl, optionally substituted heteroaryl, optionally substituted aryl, or optionally substituted biphenyl.
- provided that:
- when G.sub.2 represents G.sub.22 wherein R.sub.22 as defined above is other than optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted biphenyl, then G.sub.1 or G.sub.11 represents heteroaryl other than pyridyl that is optionally substituted, linear or branched (C.sub.1 -C.sub.6)-alkyl substituted by heteroaryl other than pyridyl that is optionally substituted, --CO--R.sub.1 or O--CO--R.sub.1, R.sub.1 being as defined above,
- when G.sub.2 represents G.sub.20 or G.sub.21 wherein R.sub.20 and R.sub.21 are other than optionally substituted aryl, optionally substituted biphenyl, or optionally substituted heteroaryl, and G.sub.1 is other than optionally substituted heteroaryl or optionally substituted naphthyl, or G.sub.11 is other than optionally substituted heteroaryl or optionally substituted naphthyl while R represents hydrogen, then B represents optionally substituted methylene or ethylene,
- when G.sub.2 represents G.sub.20 or G.sub.21, R.sub.20 or R.sub.21 as defined above being other than optionally substituted aryl or optionally substituted heteroaryl and:
- .fwdarw.when R and G.sub.1 each represents hydrogen, then G.sub.11 is other than linear or branched (C.sub.1 -C.sub.6)-alkyl, other than (C.sub.3 -C.sub.7)-cycloalkyl optionally substituted by one or more halogen, hydroxy, and other than linear or branched (C.sub.1 -C.sub.6)-alkyl substituted by one or more halogen, hydroxy, linear or branched (C.sub.1 -C.sub.6)-alkoxy, or (C.sub.3 -C.sub.7)-cycloalkyl optionally substituted by one or more halogen or hydroxy,
- .fwdarw.when G.sub.1 represents hydrogen and R represents OR', R' as defined above being other than optionally substituted heteroaryl, then G.sub.11 is other than linear or branched (C.sub.1 -C.sub.6)-alkyl, linear or branched (C.sub.2 -C.sub.6)-alkenyl, or linear or branched (C.sub.2 -C.sub.6)-alkynyl,
- when G.sub.2 represents either G.sub.21, wherein R.sub.21 is other than optionally substituted linear or branched (C.sub.2 -C.sub.6)-alkenyl and other than optionally substituted (C.sub.2 -C.sub.6)-alkynyl, or G.sub.20, wherein R.sub.20 represents (C.sub.3 -C.sub.7)-cycloalkyl optionally substituted by one or more halogen, hydroxy or linear or branched (C.sub.1 -C.sub.6)-alkoxy, or linear or branched (C.sub.1 -C.sub.6)-alkyl substituted by (C.sub.3 -C.sub.7)-cycloalkyl optionally substituted by one or more halogen, hydroxy or linear or branched (C.sub.1 -C.sub.6)-alkoxy, then:
- .fwdarw.G.sub.11 is other than linear or branched (C.sub.1 -C.sub.6)-alkyl,
- .fwdarw.G.sub.1 is other than halogen, linear or branched (C.sub.1 -C.sub.6)-alkyl, linear or branched (C.sub.1 -C.sub.6)-alkyl substituted by optionally substituted phenyl, and other than optionally substituted phenyl,
- when G.sub.2 represents G.sub.21, X representing sulphur and B representing ethylene, then R.sub.21 is other than optionally substituted aryl,
- the term "aryl" denoting phenyl or naphthyl,
- the term "heteroaryl" denoting a saturated or unsaturated, 4- to 11-membered, mono- or bi-cyclic group containing from 1 to 4 hetero atoms selected nitrogen, oxygen, and sulphur, is being understood that:
- the expression "optionally substituted" applied to the terms "alkyl", "alkenyl", "alkynyl", and "cycloalkyl" means that those groups are, if desired, substituted by one or more halogen or (C.sub.3 -C.sub.7)-cycloalkyl, hydroxy, linear or branched (C.sub.1 -C.sub.6)-alkoxy, optionally substituted aryl and/or optionally substituted heteroaryl,
- the expression "optionally substituted" applied to the terms "aryl", "biphenyl", and "heteroaryl" means that those groups are, if desired, substituted by one or more halogen and/or linear or branched (C.sub.1 -C.sub.6)-alkyl, linear or branched (C.sub.1 -C.sub.6)-trihaloalkyl, hydroxy, linear or branched (C.sub.1 -C.sub.6)-alkoxy, nitro, amino which is optionally substituted by one or two identical or different, linear or branched (C.sub.1 -C.sub.6)-alkyl;
- linear or branched (C.sub.1 -C.sub.6)-alkylcarbonyl, cyano, carboxy, and/or aminocarbonyl optionally substituted by one or two identical or different linear or branched (C.sub.1 -C.sub.6)-alkyl,
- their enantiomers and diastereoisomers, and also pharmaceutically acceptable addition salts thereof with an acid or base.
Dependencies are inferred from the claim text.