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US 6,602,903 B2Granted
Substituted heterocyclic compounds
AssigneeLes Laboratories Servier
InventorsGérald Guillaumet, Marie-Claude Viaud, Ahmed Mamai, Isabelle Charton, Pierre Renard, Caroline Bennejean, Béatrice Guardiola, Philippe Daubos
Life of this patent
Estimating the term…
Abstract
The invention relates to compounds of formula (I): and medicinal products containing the same are useful in treating or in preventing melatoninergic disorders.
Claims17
A compound selected from those of formula (I):
- wherein
- R1 and R2, located on two adjacent carbon atoms, form together with the carbon atoms that carry them aryl, or a 6-membered ring containing carbon and one or two oxygen,
- X represents oxygen, sulphur, C(H)q (wherein q is equal to 0, 1 or 2), SO, SO2, or X represents a single bond, it being understood that when X is oxygen, sulphur, SO or SO2, Y must be C(H)q (wherein q is equal to 0, 1 or 2),
- Y represents oxygen, sulphur, C(H)q (wherein q is equal to 0, 1 or 2), SO, or SO2, it being understood that when Y is oxygen, sulphur, SO or SO2, X must be C(H)q (wherein q is equal to 0, 1 or 2) or a single bond,
- it being understood that X and Y cannot simultaneously represent C(H)q (wherein q is equal to 0, 1 or 2),
- R3 represents hydrogen, aryl, aryl-(C1-C6)alkyl in which the alkyl moiety is linear or branched, or linear or branched (C1-C6)alkyl,
- n is equal to 0, 1, 2, 3, 4 or 5
- it being possible for the —(CH2)n— chain to be substituted by one or more halogen or one or more identical or different groups selected from linear or branched (C1-C6)alkyl, OH, linear or branched (C1-C6)alkylcarbonyl, linear or branched (C1-C6)alkoxycarbonyl, and linear or branched (C1-C6)alkoxy,
- A represents
- NR5R6 wherein
- R6 represents hydrogen or linear or branched (C1-C6)alkyl,
- R5 represents
- wherein Z represents oxygen or sulphur, and R7 represents hydrogen, or
- R8 which represents substituted or unsubstituted linear or branched (C1-C6)alkyl, substituted or unsubstituted (C3-C8)cycloalkyl, substituted or unsubstituted (C3-C8)cycloalkyl-(C1-C6)alkyl in which the alkyl moiety is linear or branched, substituted or unsubstituted linear or branched (C2-C6)alkenyl, substituted or unsubstituted linear or branched (C2-C6)alkynyl, aryl, or aryl-(C1-C6)alkyl in which the alkyl moiety is linear or branched,
- or NR8R9 wherein R9 represents hydrogen or linear or branched (C1-C6)alkyl and R8 is as defined hereinabove,
- the symbol
- means that the bonds can be single or double, it being understood that two adjacent bonds cannot simultaneously be double and that the valency of the atoms is respected,
- it being understood that:
- the term “aryl” denotes phenyl or naphthyl optionally substituted by one or more halogen or one or more identical or different groups selected from OH, linear or branched (C1-C6)alkoxy, linear or branched (C1-C6)alkyl, cyano, nitro, amino, alkylamino, dialkylamino, and trihaloalkyl,
- the term “substituted” used in respect of the terms “alkyl”, “alkenyl” and “alkynyl” means that the group is substituted by one or more halogen or one or more identical or different groups selected from OH, linear or branched (C1-C6)alkoxy, amino, alkylamino, and dialkylamino,
- the term “substituted” used in respect of the terms “cycloalkyl” and “cycloalkylalkyl” means that the cyclic moiety is substituted by one or more halogen or one or more identical or different groups selected from linear or branched (C1-C6)alkyl, linear or branched (C1-C6)alkoxy, hydroxy, oxo, amino, alkylamino, and dialkylamino,
- provided that:
- when A represents NHCSNHR8 and n is equal to 2, R8 cannot represent aryl,
- its enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically-acceptable acid or base.
21 more elements
A compound selected from those of formula (I):
- wherein
- R1 and R2, located on two adjacent carbon atoms, form together with the carbon atoms that carry them aryl, or a 6-membered ring containing carbon and one or two oxygen,
- X represents a single bond,
- Y represents oxygen, sulphur, C(H)q (wherein q is equal to 0, 1 or 2), SO, or SO2,
- R3 represents hydrogen, aryl, aryl-(C1-C6)alkyl in which the alkyl moiety is linear or branched, or linear or branched (C1-C6)alkyl,
- n is equal to 0, 1, 2, 3, 4 or 5
- it being possible for the —(CH2)n— chain to be substituted by one or more halogen or one or more identical or different groups selected from linear or branched (C1-C6)alkyl, OH, linear or branched (C1-C6)alkoxy, linear or branched (C1-C6)alkylcarbonyl, and linear or branched (C1-C6)alkoxycarbonyl,
- A represents
- NR5R6 wherein
- R6 represents hydrogen or linear or branched (C1-C6)alkyl,
- R5 represents
- wherein Z represents oxygen or sulphur, and R7 represents:
- hydrogen, or
- R8 which represents substituted or unsubstituted linear or branched (C1-C6)alkyl, substituted or unsubstituted (C3-C8)cycloalkyl, substituted or unsubstituted (C3-C8)cycloalkyl-(C1-C6)alkyl in which the alkyl moiety is linear or branched, substituted or unsubstituted linear or branched (C2-C6)alkenyl, substituted or unsubstituted linear or branched (C2-C6)alkynyl, aryl, or aryl-(C1-C6)alkyl in which the alkyl moiety is linear or branched,
- or NR8R9 wherein R9 represents hydrogen or linear or branched (C1-C6)alkyl and R8 is as defined hereinabove,
- the symbol
- means that the bonds can be single or double, it being understood that two adjacent bonds cannot simultaneously be double and that the valency of the atoms is respected,
- it being understood that:
- the term “aryl” denotes phenyl or naphthyl optionally substituted by one or more halogen or one or more identical or different groups selected from OH, linear or branched (C1-C6)alkoxy, linear or branched (C1-C6)alkyl, cyano, nitro, amino, alkylamino, dialkylamino, and trihaloalkyl,
- the term “substituted” used in respect of the terms “alkyl”, “alkenyl” and “alkynyl” means that the group is substituted by one or more halogen or one or more identical or different groups selected from OH, linear or branched (C1-C6)alkoxy, amino, alkylamino, and dialkylamino,
- the term “substituted” used in respect of the terms “cycloalkyl” and “cycloalkylalkyl” means that the cyclic moiety is substituted by one or more halogen or one or more identical or different groups selected from linear or branched (C1-C6)alkyl, linear or branched (C1-C6)alkoxy, hydroxy, oxo, amino, alkylamino, and dialkylamino,
- provided that:
- when A represents NHCSNHR8 and n is equal to 2, R8 cannot represent aryl,
- its enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically-acceptable acid or base.
21 more elements
Dependencies are inferred from the claim text.