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US 10,294,244 B2Granted
2,3-dihydro-thiazolo[3,2-A]pyridin-5-one derivatives, intermediates thereof, and their use as antibacterial agents
AssigneeQuretech Bio AB
InventorsJames Arthur Dudley Good, Anna Martina Kulén, Klas Fredrik Almqvist, Andrew Gerard Cairns, John Fritiof Pontén
Life of this patent
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Abstract
The disclosure relates to certain novel substituted ring-fused thiazolino 2-pyridines of Formula I, to processes for preparing such compounds, to their use in treating a bacterial infection such as Chlamydia infection, to methods for their therapeutic use and to pharmaceutical compositions containing them.
Claims23
A compound of Formula I
- or a pharmaceutically acceptable salt thereof,
- wherein
- R1 is selected from the group consisting of
- a) C(O)NR5R6,
- b) C(O)OH,
- c) C(O)SO2R8, and
- d)
- R2 is selected from the group consisting of
- a) OH,
- b) NZ1Z2,
- c) C1-C4alkoxy substituted with 0,1, 2 or 3 substituents independently selected from the group consisting of F and Cl,
- d) cyclopropoxy, cyclopropylmethoxy, phenyloxy, 2-pyridinyloxy or 4-pyridinyloxy each independently substituted with 0, 1, 2 or 3 substituents selected from the group consisting of F, Cl, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, methoxy, CH3SO2O and phenylSO2O,
- e) C1-C3alkylthio, C1-C3alkylS(O), C1-C3alkylS(O)2, phenylthio, phenylS(O) or phenylS(O)2 each independently substituted with 0, 1, 2 or 3 substituents selected from the group consisting of F, Cl, methoxy, methyl and trifluoromethyl,
- f) 2-pyridinylS(O)2 substituted with 0, 1 or 2 substituents in positions 3, 4 or 5 independently selected from the group consisting of F, Cl, methoxy, methyl and trifluoromethyl,
- g) 4-pyridinylS(O)2 substituted with 0, 1 or 2 substituents in positions 2, 3 or 5 independently selected from the group consisting of F, Cl, methoxy, methyl and trifluoromethyl,
- h) Cl or F,
- and
- i) CF3;
- R3 is selected from the group consisting of
- a) CX1X2phenyl, CH2Ophenyl, CX1X2-(2)-pyridyl, CX1X2-(3)-pyridyl and CX1X2-(4)-pyridyl, each independently substituted with 0, 1, 2 or 3 substituents selected from the group consisting of F, Cl, methoxy, trifluoromethyl and methyl,
- b) 1,3-dioxa-5-indanyl-methylene,
- c) 1-naphtyl-methylene or 1-naphtyl-4-methyl-methylene,
- and
- d) 7-thiabicyclo[4.3.0]nona-1,3,5,8-tetraen-9-yl-methylene;
- R4 is selected from the group consisting of:
- a) hydrogen,
- and
- b) NY1Y2;
- and in the above definitions
- R5 represents hydrogen or C1-C6alkyl,
- or
- R5 represents phenyl, 2-pyridinyl or 4-pyridinyl each independently substituted with 0, 1, 2 or 3 substituents selected from the group consisting of F, Cl, methoxy, methyl and trifluoromethyl;
- R6 represents hydrogen, C1-C4alkyl or C1-C6cycloalkyl;
- R7 represents phenyl or 2-pyridinyl each independently substituted with 0, 1 or 2 substituents selected from the group consisting of F, Cl, methoxy, methyl and trifluoromethyl;
- R8 represents C1-C3alkyl, phenyl, 2-pyridinyl or 4-pyridinyl each independently substituted with 0, 1 or 2 substituents selected from the group consisting of F, Cl, methoxy, methyl and trifluoromethyl;
- X1 and X2 each independently represents hydrogen, OH, halogen, oxo or NH2;
- Y1 and Y2 each independently represents hydrogen, methyl or C(O)CH3, CH3S(O)2 or Y1 and Y2 together form CH2CH2CH2CH2 or CH2CH2CH2CH2CH2;
- Z1 and Z2 each independently represents hydrogen, C1-C4alkyl, C3-C5cycloalkyl, C(O)CH3, C(O)OCH3, CH3S(O)2 or phenylS(O)2, or Z1 and Z2 together form CH2CH2CH2, CH2CH2CH2CH2 or CH2CH2CH2CH2CH2;
- with the proviso that the compound of Formula (I) is not (3R)-7-methoxy-6-[(1-naphthyl)methyl]-4-oxo-1-thia-3a-aza-3-indancarboxylic acid, (3R)-6-[(1,3-dioxa-5-indanyl)methyl]-7-methoxy-4-oxo-1-thia-3a-aza-3-indancarboxylic acid or (3R)-7-methoxy-4-oxo-6-{(7-thiabicyclo[4.3.0]nona-1,3,5,8-tetraen-9-yl)methyl}-1-thia-3a-aza-3-indancarboxylic acid.
36 more elements
Dependencies are inferred from the claim text.