Aniline derivatives, their preparation and their therapeutic application
AssigneeSanofi
InventorsJohn Feutrill, Caroline Leriche, David Middlemiss
Life of this patent
Estimating the term…
Abstract
The present invention relates to therapeutic applications of aniline derivatives of formula (I), for example in treating glaucoma: Formula (I), R1a represents H, an halogen, a (C1-C6)alkyl or a CN; R1b represents H, an halogen or a (C1-C6)alkyl; R1c represents H or a (C1-C6)alkyl; R2 represents H, an halogen, an OH, an O—(C1-C6)alkyl or (C1-C6)alkyl; R3 represents H, an halogen, a (C1-C6)alkyl, an OH, an O—(C1-C6)alkyl, a CONH2 or CN; R4 represents H, an halogen or a (C1-C6)alkyl; R5 represents H or F: R7 represents H or F; R8 represents H or F; R9 represents H or (C1-C6)alkyl, or one of its enantiomers.
Claims24
A method of treatment of glaucoma, which comprises administering to a patient in need thereof an effective dose of a compound of formula (I) or formula (II), or an enantiomer thereof, wherein the compound of formula (II) is a prodrug of compound of formula (I):
- wherein
- R1a represents H, a halogen, a (C1-C6)alkyl or a CN;
- R1b represents H, a halogen or a (C1-C6)alkyl;
- R1c represents H or a (C1-C6)alkyl;
- R2 represents H, a halogen, an OH, an O—(C1-C6)alkyl or a (C1-C6)alkyl;
- R3 represents H, a halogen, a (C1-C6)alkyl, an OH, an O—(C1-C6)alkyl, a CONH2 or a CN;
- R4 represents H, a halogen or a (C1-C6)alkyl;
- R5 represents H or F;
- R6 represents an O—(C1-C6)alkyl, an O—(C1-C6)alkyl-heterocycloalkyl, a NH2, a NH—(C1-C6)alkyl, an O—(C1-C6)alkyl optionally substituted by one to three hydroxyl groups, O—(C1-C6)alkyl-O—CO(C1-C6)alkyl);
- R7 represents H or F;
- R8 represents H or F;
- and
- R9 represents H or a (C1-C6)alkyl.
A method of treatment of glaucoma, which comprises administering to a patient in need thereof a pharmaceutical composition comprising an effective dose of a compound of formula (I) or of formula (II), or an enantiomer thereof, wherein the compound of formula (II) is a prodrug of compound of formula (I), said pharmaceutical composition comprising also at least one pharmaceutically acceptable excipient, wherein said compound is as follows:
- wherein
- R1a represents H, a halogen, a (C1-C6)alkyl or a CN;
- R1b represents H, a halogen or a (C1-C6)alkyl;
- R1c represents H or a (C1-C6)alkyl;
- R2 represents H, a halogen, an OH, an O—(C1-C6)alkyl or a (C1-C6)alkyl;
- R3 represents H, a halogen, a (C1-C6)alkyl, an OH, an O—(C1-C6)alkyl, a CONH2 or a CN;
- R4 represents H, a halogen or a (C1-C6)alkyl;
- R5 represents H or F;
- R6 represents an O—(C1-C6)alkyl, an O—(C1-C6)alkyl-heterocycloalkyl, a NH2, a NH—(C1-C6)alkyl, an O—(C1-C6)alkyl optionally substituted by one to three hydroxyl groups, O—(C1-C6)alkyl-O—CO(C1-C6)alkyl);
- R7 represents H or F;
- R8 represents H or F;
- and
- R9 represents H or a (C1-C6)alkyl.
A method of treatment of an ocular disease involving EP2 receptors, which comprises administering to a patient in need thereof a pharmaceutical composition comprising an effective dose of a compound of formula (I) or of formula (II), or an enantiomer thereof, wherein the compound of formula (II) is a prodrug of compound of formula (I), said pharmaceutical composition comprising also at least one pharmaceutically acceptable excipient, wherein said compound of formula (I) or of formula (II) is as follows:
- wherein
- R1a represents H, a halogen, a (C1-C6)alkyl or a CN;
- R1b represents H, a halogen or a (C1-C6)alkyl;
- R1c represents H or a (C1-C6)alkyl;
- R2 represents H, a halogen, an OH, an O—(C1-C6)alkyl or a (C1-C6)alkyl;
- R3 represents H, a halogen, a (C1-C6)alkyl, an OH, an O—(C1-C6)alkyl, a CONH2 or a CN;
- R4 represents H, a halogen or a (C1-C6)alkyl;
- R5 represents H or F;
- R6 represents an O—(C1-C6)alkyl, an O—(C1-C6)alkyl-heterocycloalkyl, a NH2, a NH—(C1-C6)alkyl, an O—(C1-C6)alkyl optionally substituted by one to three hydroxyl groups, O—(C1-C6)alkyl-O—CO(C1-C6)alkyl);
- R7 represents H or F;
- R8 represents H or F;
- and
- R9 represents H or a (C1-C6)alkyl.
Dependencies are inferred from the claim text.