Chromen-2-one derivatives
This invention relates to novel chromen-2-one derivatives useful as starting material for synthesis of pharmaceuticals. On other aspects the invention relates to a method of preparing the chromen-2-one derivatives of the invention.
1. A compound of Formula I:
any of its stereoisomers or any mixture of its stereoisomers,
or an addition salt thereof,
wherein
Q represents chromen-2-one-yl,
which chromen-2-one-yl is optionally substituted with one or more substituents independently selected from the group consisting of:
halo, trifluoromethyl, trifluoromethoxy, cyano, hydroxy, amino, nitro, alkoxy, cycloalkoxy, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl and alkynyl.
2. The compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents chromen-2-one-yl.
3. The compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents chromen-2-one-yl,
which chromen-2-one-yl is substituted with a substituent selected from the group consisting of: halo, cyano and alkyl.
4. The compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents chromen-2-one-yl,
which chromen-2-one-yl is substituted in the 3-position with a substituent selected from the group consisting of:
halo, trifluoromethyl, trifluoromethoxy, cyano, hydroxy, amino, nitro, alkoxy, cycloalkoxy, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl and alkynyl.
5. The compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents chromen-2-one-yl,
which chromen-2-one-yl is substituted in the 3-position with a substituent selected from the group consisting of: halo, cyano and alkyl.
6. The compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents chromen-2-one-yl,
which chromen-2-one-yl is substituted in the 4-position with a substituent selected from the group consisting of:
halo, trifluoromethyl, trifluoromethoxy, cyano, hydroxy, amino, nitro, alkoxy, cycloalkoxy, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl and alkynyl.
7. The compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents chromen-2-one-yl,
which chromen-2-one-yl is substituted in the 4-position with a substituent selected from the group consisting of: halo, cyano and alkyl.
8. The compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents chromen-2-one-yl,
which chromen-2-one-yl is substituted in the 3- and 4-positions with substituents independently selected from the group consisting of:
halo, trifluoromethyl, trifluoromethoxy, cyano, hydroxy, amino, nitro, alkoxy, cycloalkoxy, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl and alkynyl.
9. The compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents chromen-2-one-yl,
which chromen-2-one-yl is substituted in the 3- and 4-positions with substituents independently selected from the group consisting of:
halo, cyano and alkyl.
10. The chemical compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents an optionally substituted chromen-2-one-4-yl group.
11. The chemical compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents an optionally substituted chromen-2-one-6-yl group.
12. The chemical compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, wherein Q represents an optionally substituted chromen-2-one-7-yl group.
13. The chemical compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or an addition salt thereof, which is exo-3-(2-Oxo-2H-chromen-7-yloxy)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid 2,2,2-trichloro-ethyl ester,
or a pharmaceutically acceptable salt thereof.
14. A process for preparing a compound of Formula I
any of its stereoisomers or any mixture of its stereoisomers,
wherein Q represents chromen-2-one-yl,
which chromen-2-one-yl is optionally substituted with one or more substituents independently selected from the group consisting of:
halo, trifluoromethyl, trifluoromethoxy, cyano, hydroxy, amino, nitro, alkoxy, cycloalkoxy, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl and alkynyl;
which process comprises:
reacting a 3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester
with a hydroxy-chromen-2-one,
which hydroxy-chromen-2-one is optionally further substituted with one or more substituents independently selected from the group consisting of:
halo, trifluoromethyl, trifluoromethoxy, cyano, hydroxy, amino, nitro, alkoxy, cycloalkoxy, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl and alkynyl.
15. A process for preparing a compound of Formula II
any of its stereoisomers or any mixture of its stereoisomers,
wherein Q represents chromen-2-one-yl,
which chromen-2-one-yl is optionally substituted with one or more substituents independently selected from the group consisting of:
halo, trifluoromethyl, trifluoromethoxy, cyano, hydroxy, amino, nitro, alkoxy, cycloalkoxy, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl and alkynyl;
which process comprises:
reacting a compound of Formula I with acid in the presence of a transition metal catalyst
wherein Q is as defined in formula II.