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US 2013/0158051 A1Published application
Heterocyclic carboxylic acid derivatives having a 2,5,7-substituted oxazolopyrimidine ring
AssigneeSanofi
InventorsDieter Kadereit, Matthias Schaefer, Stephanie Hachtel, Axel Dietrich, Thomas Huebschle, Andreas Gille, Katrin Hiss
Life of this patent
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Abstract
The invention relates to oxazolopyrimidine compounds of formula (I), where A, R1, R2, R3, R4, X and Y are defined as stated in the claims. The compounds of formula I are suitable, for example, for wound healing.
Claims17
A compound of the formula I, in any of its stereoisomeric forms, or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of such a compound or such a salt,
- wherein
- A is selected from the group consisting of NH, O and S;
- X is selected from the group consisting of (C1-C6)-alkanediyl, (C2-C6)-alkenediyl, (C2-C6)-alkynediyl, (C3-C7)-cycloalkanediyl and (C1-C6)-alkanediyloxy, all of which are optionally substituted by one or more identical or different substituents selected from the group consisting of fluorine and hydroxyl, where the oxygen atom of the (C1-C6)-alkanediyloxy group is attached to the group R2;
- Y is a 4-membered to 7-membered saturated or partially unsaturated monocyclic or bicyclic heterocycle which, in addition to the ring nitrogen atom shown in formula I, contains 0, 1, 2 or 3 identical or different ring heteroatoms selected from the group consisting of N, O and S, where one or two, of the additional ring nitrogen atoms may carry a hydrogen atom or a (C1-C4)-alkyl substituent and one of the ring sulfur atoms may carry one or two oxo groups and where the heterocycle is optionally substituted at one or more ring carbon atoms by identical or different (C1-C4)-alkyl substituents;
- R1 is selected from the group consisting of (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C7)-cycloalkyl-CtH2t— and Het-CtH2t—, in which t is selected from the group consisting of 0, 1, 2 and 3;
- R2 is selected from the group consisting of phenylene and a bivalent radical of an aromatic 5-membered or 6-membered monocyclic heterocycle which contains 1, 2 or 3 identical or different ring heteroatoms selected from the group consisting of N, O and S, where one of the ring nitrogen atoms may carry a hydrogen atom or a substituent R21 and where the phenylene and the bivalent radical of an aromatic heterocycle are optionally substituted at one or more ring carbon atoms by identical or different substituents R22;
- R3 is selected from the group consisting of (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C7)-cycloalkyl-CuH2u— and Het-CvH2v—, in which u and v are selected from the group consisting of 1 and 2, or R3 is a radical of a saturated or unsaturated 3-membered to 10-membered monocyclic or bicyclic ring which contains 0, 1, 2, 3 or 4 identical or different ring heteroatoms selected from the group consisting of N, O and S, where one or two of the ring nitrogen atoms may carry a hydrogen atom or a (C1-C4)-alkyl substituent and one or two of the ring sulfur atoms may carry one or two oxo groups and where the radical of a ring is optionally substituted at one or more ring carbon atoms by identical or different substituents R31, with the proviso that R3 may not represent (C1-C6)-alkyl if A represents S;
- R4 is selected from the group consisting of hydrogen, (C1-C4)-alkyl and (C3-C7)-cycloalkyl-CzH2z—, where z is selected from the group consisting of 0, 1 and 2;
- R21 is selected from the group consisting of (C1-C4)-alkyl and (C3-C7)-cycloalkyl-CwH2w— and oxy, where w is selected from the group consisting of 0, 1 and 2;
- R22 is selected from the group consisting of halogen, hydroxyl, (C1-C4)-alkyl-, (C1-C4)-alkyloxy, (C1-C4)-alkyl-S(O)m—, amino, nitro, cyano, hydroxycarbonyl, (C1-C4)-alkyloxycarbonyl, aminocarbonyl and aminosulfonyl;
- R31 is selected from the group consisting of halogen, (C1-C4)-alkyl, (C3-C7)-cycloalkyl, hydroxyl, (C1-C4)-alkyloxy, oxo, (C1-C4)-alkyl-S(O)m—, amino, (C1-C4)-alkylamino, di((C1-C4)-alkyl)amino, (C1-C4)-alkylcarbonylamino, (C1-C4)-alkylsulfonylamino, nitro, cyano, (C1-C4)-alkylcarbonyl, aminosulfonyl, (C1-C4)-alkylaminosulfonyl and di((C1-C4)-alkyl)aminosulfonyl;
- Het is a radical of a saturated 4-membered to 7-membered monocyclic heterocycle which contains 1 or 2 identical or different ring heteroatoms selected from the group consisting of N, O and S and which is attached via a ring carbon atom, where the radical of a heterocycle is optionally substituted by one or more identical or different substituents selected from the group consisting of fluorine and (C1-C4)-alkyl;
- m is selected from the group consisting of 0, 1 and 2, where all numbers m are independent of one another;
- where all cycloalkyl and cycloalkanediyl groups independently of one another and independently of other substituents are optionally substituted by one or more identical or different substituents which are selected from the group consisting of fluorine and (C1-C4)-alkyl;
- where all alkyl, alkanediyl, CtH2t, CuH2u, CwH2w, CvH2v, alkenyl, alkenediyl, alkynyl and alkynediyl groups independently of one another and independently of other substituents are optionally substituted by one or more fluorine substituents.
12 more elements
(canceled)
Dependencies are inferred from the claim text.