| abstract |
The present invention relates to novel florfenicol compounds having the chemical structure: 1. A compound, comprising the chemical formula: wherein: R1 is selected from the group consisting of -OH and -F; R2 and R3 are independently selected from the group consisting of hydrogen, (1C-4C)alkyl, halo, -CF3, -NH2, -CN and N3; R4 is selected from the group consisting of: (1C-4C)alkyl(C(OH)-; -C(=R5)R6 wherein: R5 is selected from the group consisting of oxygen, N-C≡N, and NOR7, R6 is selected from the group consisting of hydrogen, (1C-4C)alkyl, (3C-6C)cycloalkyl, (1C-4C)alkoxy, heteroaryl, alicyclic and heteroalicyclic and R7 is selected from the group consisting of hydrogen, alkyl, aryl, heteroaryl, alicyclic and heteroalicyclic, wherein: A1 is carbon or nitrogen; A2, A3, A4 and A5 are independently selected from the group consisting of carbon, nitrogen, oxygen and sulfur, provided that the resulting ring is aromatic; carbon atoms in the ring are independently substituted with an entity selected from the group consisting of hydrogen, (1C-4C)alkyl, (3C-6C)cycloalkyl, (1C-4C)alkylO-, -CF3, -OH, -CN, halo, (1C-4C)alkylS(O)n, NH2SO2-, (1C-4C)alkylNHSO2-, ((1C-4C)alkyl)2NSO2- , -NH2, (1C-4C)alkylNH-, ((1C-4C)alkyl)2N-, (1C-4C)alkylSO2NH-, (1C-4C)alkylC(O)-, (3C-6C)cycloalkylC(O)-, (1C-4C)alkylOC(O)-, (1C-4C)alkylC(O)NH-, -C(O)NH2, (1C-4C)alkylNHC(O)- and ((1C-4C)alkyl)2NC(O)-, wherein the alkyl group may optionally be substituted with a group selected from halo and hydroxy and n is 0, 1 or 2; and, wherein: A6, A7, A8, A9 and A10 are independently selected from the group consisting of carbon, nitrogen and, provided that only one of A6-A10 at a time can be, ; wherein: carbon atoms in the ring are independently substituted with an entity selected from the group consisting of hydrogen, (1C-4C)alkyl, (3C-6C)cycloalkyl, (1C-4C)alkylO-, -CF3, -OH, -CN, halo, (1C-4C)alkylS(O)n, NH2SO2-, (1C-4C)alkylNHSO2-, ((1C-4C)alkyl)2NSO2-, -NH2, (1C-4C)alkylNH-, ((1C-4C)alkyl)2N-, (1C-4C)alkylSO2NH-, (1C-4C)alkylC(O)-, (3C-6C)cycloalkylC(O)-, (1C-4C)alkylOC(O)-, (1C-4C)alkylC(O)NH-, -C(O)NH2, (1C-4C)alkylNHC(O)-, ((1C-4C)alkyl)2NC(O)- and -OCH2O-, the oxygen atoms being bonded to adjacent ring carbon atoms, wherein the alkyl group may optionally be substituted with a group selected from halo and hydroxy and n is 0, 1 or 2; R8 is hydrogen in all compounds except when R2 and R3 are both F, in which case R8 is hydrogen or F; and, the compound is either a racemate having the relative stereochemistry shown or is substantially enantiomerically pure and has the absolute stereochemistry shown. |