Claims
- 1. A compound of the formula: or the pharmaceutically acceptable salt thereof; wherein the dashed line between positions 10 and 11 represents an optional double bond;a is 0 or 1; R1 is hydrogen or (C1-C10)alkyl optionally substituted by fluoro, cyano, R7, R7O2C, R7C(O)NH or R7S(O)n wherein n is 0, 1 or 2 and R7 is (C1-C6)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C10)cycloalkyl(C1-C6)alkyl, (C2-C9)heterocycloalkyl(C1-C6)alkyl, (C6-C10)aryl(C1-C6)alkyl or (C2-C9)heteroaryl(C1-C6)alkyl wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups are optionally substituted by one to three halo, (C1-C3)alkoxy, hydroxy, nitro, cyano, (C6-C10)aryl, (C2-C9)heteroaryl, R8R9N, R8C(O), R8C(O)O, R8OC(O), R8C(O)NH, R8NHC(O), R8R9NC(O) and R8OC(O)2 wherein R8 and R9 are each independently hydrogen, (C1-C6)alkyl optionally substituted by (C6-C10)aryl or (C2-C9)heteroaryl; R2 is hydrogen or a hydroxy protecting group; R3 is N3, R10NH, R10C(O)NH, R10NHC(O)NH, R10NHC(S)NH, R10NHNHC(O)NH, R10ONHC(O)NH or R10OC(O)NH, wherein R10 is (C1-C6)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C10)cycloalkyl(C1-C6)alkyl, (C2-C9)heterocycloalkyl(C1-C6)alkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C6)alkyl or (C2-C9)heteroaryl(C1-C6)alkyl; wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups are optionally substituted by one to three substituents independently selected from halo, (C1-C3)alkoxy, hydroxy, nitro, cyano, (C6-C10)aryl, (C2-C9)heteroaryl, R8R9N, R8C(O), R8C(O)O, R8OC(O), R8C(O)NH, R8NHC(O), R8R9NC(O) and R8OC(O)2 wherein R8 and R9 are each independently hydrogen, (C1-C6)alkyl optionally substituted by (C6-C10)aryl or (C2-C9)heteroaryl; or R3 is R11(C2-C4)alkynyl wherein R11 is (C1-C6)alkyl, (C6-C10)alkyl(C6-C10)aryl(C1-C6)alkyl or (C2-C9)heteroaryl(C1-C6)alkyl; or R3 is R12R13N wherein R12 and R13 are each independently hydrogen, (C1-C6)alkyl, (C6-C10)aryl(C1-C6)alkyl or (C2-C9)heteroaryl (C1-C6)alkyl; X is oxygen or NOR16 wherein R16 is (C1-C6)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C10)cycloalkyl(C1-C6)alkyl, (C2-C9)heterocycloalkyl(C1-C6)alkyl, (C6-C10)aryl(C1-C6)alkyl or (C2-C9)heteroaryl(C1-C6)alkyl; wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups are optionally substituted by one to three substituents independently selected from halo, (C1-C3)alkoxy, hydroxy, nitro, cyano, (C6-C10)aryl, (C5-C9)heteroaryl, R8R9N, R8C(O), R8C(O)O, R8OC(O), R8C(O)NH, R8NHC(O), R8R9NC(O) and R8OC(O)2, wherein R8 and R9 are each independently hydrogen or (C1-C6)alkyl optionally substituted by (C6-C10)aryl or (C2-C9)heteroaryl; R5 is hydrogen or methyl; and R6 is hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy(C1-C6)alkyl or (C1-C6)alkylthio(C1-C6)alkyl wherein the alkyl, alkenyl, alkynyl or alkoxy groups are optionally substituted by one to three substituents independently selected from hydroxy and halo; or R6 is (C3-C10)cycloalkyl or (C5-C10)cycloalkenyl optionally substituted by (C1-C6)alkyl or halo; or R6 is (C2-C8)heterocycloalkyl or (C2-C9)heteroaryl optionally substituted by (C1-C6)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C10)cycloalkyl, (C5-C10)cycloalkenyl or aryl wherein the aryl group is optionally substituted by alkyl, (C1-C6)alkoxy or halo; with the proviso that when a is zero, R1 is hydrogen.
- 2. A pharmaceutical composition for the treatment of a disorder selected from a bacterial infection, a protozoal infection, and a disorder related to a bacterial infection or protozoal infection in a mammal, fish, or bird which comprises a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
- 3. A method of treating a disorder selected from a bacterial infection, a protozoal infection, and a disorder related to a bacterial infection or protozoal infection in a mammal, fish, or bird which comprises administering to said mammal, fish or bird a therapeutically effective amount of a compound of claim 1.
- 4. A compound of the formula: a is 0 or 1; R1 is hydrogen or (C1-C10)alkyl optionally substituted by fluoro, cyano, R7, R7O2C, R7C(O)NH or R7S(O)n wherein n is 0.1 or 2 and R7 is (C1-C6)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C10)cycloalkyl(C1-C6)alkyl, (C2C9)heterocycloalkyl(C1-C6)alkyl, (C6-C10)aryl(C1-C6)alkyl or (C2-C9)heteroaryl(C1-C6)alkyl wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups are optionally substituted by one to three substituents independently selected from halo, (C1-C3)alkoxy, hydroxy, nitro, cyano, (C6-C10)aryl, (C2-C9)heteroaryl, R8R9N, R8C(O), R8C(O)O, R8OC(O), R8C(O)NH, R8NHC(O), R8R9NC(O) and R8OC(O)2 where R8 and R9 are each independently hydrogen, (C1-C6)alkyl optionally substituted by (C6-C10)aryl or (C2-C9)heteroaryl; R2 is hydrogen or a hydroxy protecting group; R3 is NH2, N3, O═C═N or S═C═N; X is oxygen or NOR16 wherein R16 is (C1-C6)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C10)cycloalkyl(C1-C6)alkyl, (C2-C9)heterocycloalkyl(C1-)alky, (C6-C10)aryl(C1-C6)alkyl or (C2-C9)heteroaryl(C1-C6)alkyl; wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups are optionally substituted by one to three substituents independently selected from halo, (C1-C3)alkoxy, hydroxy, nitro, cyano, (C6-C10)aryl, (C2-C9)heteroaryl, R8R9N, R8C(O), R8C(O)O, R8OC(O), R8C(O)NH, R8NHC(O), R8R9NC(O) and R8OC(O)2, wherein R8 and R9 are each independently hydrogen or (C1-C6)alkyl optionally substituted by (C6-C10)aryl or (C2-C9)heteroaryl; R5 is hydrogen or methyl; and R6 is hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy(C1-C6)alkyl or (C1-C6)alkylthio(C1-C6)alkyl wherein the alkyl, alkenyl, alkynyl or alkoxy groups are optionally substituted by one to three hydroxy or halo groups; or R6 is (C3-C10)cycloalkyl or (C5-C10)cycloalkenyl optionally substituted by (C1-C6)alkyl or halo; or R6 is (C2-C8)heterocycloalkyl or (C2-C9)heteroaryl optionally substituted by (C1-C6 )alkyl, (C2-C8)alkenyl, (C2C8)alkynyl, (C3-C10)cycloalkyl, (C5-C10)cycloalkenyl or aryl wherein the aryl group is optionally substituted by alkyl, (C1-C6)alkoxy or halo.
- 5. A compound of the formula: a is 0 or 1; R1 is hydrogen or (C1-C10)alkyl optionally substituted by fluoro, cyano, R7, R7O2C, R7C(O)NH or R7S(O)n wherein n is 0, 1 or 2 and R7 is (C1-C5)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C10)cycloalkyl(C1-C6)alkyl, (C2-C9)heterocycloalkyl(C1-C6)alkyl, (C6-C10)aryl(C1-C6)alkyl or (C2-C9)heteroaryl(C1-C6)alkyl wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups are optionally substituted by one to three halo, (C1-C3)alkoxy, hydroxy, nitro, cyano, (C6-C10)aryl, (C2-C9)heteroaryl, R8R9N, R8C(O), R8C(O)O, R8OC(O), R8C(O)NH, R8NHC(O), R8R9NC(O) and R8OC(O)2 wherein R8 and R9 are each independently hydrogen, (C1-C6)alkyl optionally substituted by (C6-C10)aryl or (C2-C9)heteroaryl; R2 is hydrogen or a hydroxy protecting group; is NH2 or N3; X is oxygen or NOR16 wherein R16 is (C1-C6)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C10)cycloalkyl(C1-C6)alkyl, (C2-C9)heterocycloalkyl(C1-C6)alkyl, (C6-C10)aryl(C1-C6)alkyl or (C2-C9)heteroaryl(C1-C6)alkyl; wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups are optionally substituted by one to three substituents independently selected from halo, (C1-C3)alkoxy, hydroxy, nitro, cyano, (C6-C10)aryl, (C2-C9)heteroaryl, R8R9N, R8C(O), R8C(O)O, R8OC(O), R8C(O)NH, R8NHC(O), R8R9NC(O) and R8OC(O)2, wherein R8 and R9 are each independently hydrogen or (C1-C6)alkyl optionally substituted by (C614 C10)aryl or (C2-C9)heteroaryl; R5 is hydrogen or methyl; and R6 is hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy(C1-C6)alkyl or (C1-C6)alkylthio(C1-C6)alkyl wherein the alkyl, alkenyl, alkynyl or alkoxy groups are optionally substituted by one to three substituents independently selected from hydroxy and halo; or R6 is (C3-C10)cycloalkyl or (C5-C10)cycloalkenyl optionally substituted by (C1 -C6)alkyl or halo; or R6 is (C2-C8)heterocycloalkyl or (C2-C9)heteroaryl optionally substituted by (C1-C6)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C10)cycloalkyl, (C5-C10)cycloalkenyl or aryl wherein the aryl group is optionally substituted by alkyl, (C1-C6)alkoxy or halo.
- 6. A compound of the formula: a is 0 or 1; R1 is hydrogen or (C1-C10)alkyl optionally substituted by fluoro, cyano, R7, R7O2C, R7C(O)NH or R7S(O)n wherein n is 0, 1 or 2 and R7 is (C1-C6)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C10)cycloalkyl(C1-C6)alkyl, (C2-C9)heterocycloalkyl(C1-C6)alkyl, (C6-C10)aryl(C1-C6)alkyl or (C2-C9)heteroaryl(C1-C6)alkyl wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups are optionally substituted by one to three halo, (C1-C3)alkoxy, hydroxy, nitro, cyano, (C6-C10)aryl, (C2-C9)heteroaryl, R8R9N, R8C(O), R8C(O)O, R8OC(O), R8C(O)NH, R8NHC(O), R8R9NC(O) and R8OC(O)2 wherein R8 and R9 are each independently hydrogen, (C1-C6)alkyl optionally substituted by (C6-C10)aryl or (C2-C9)heteroaryl; R2 is hydrogen or a hydroxy protecting group; R5 is hydrogen or methyl; and R6 is hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy(C1-C6)alkyl or (C1-C6)alkylthio(C1-C6)alkyl wherein the alkyl, alkenyl, alkynyl or alkoxy groups are optionally substituted by one to three substituents independently selected from hydroxy and halo; or R6 is (C3-C10)cycloalkyl or (C5-C10)cycloalkenyl optionally substituted by (C1-C6)alkyl or halo; or R6 is (C2-C8)heterocycloalkyl or (C2-C9)heteroaryl optionally substituted by (C1 -C6)alkyl, (C2C8)alkenyl, (C2C8)alkynyl, (C3-C10)cycloalkyl, (C5-C10)cycloalkenyl or aryl wherein the aryl group is optionally substituted by alkyl, (C1-C6)alkoxy or halo.
CROSS-REFERENCE TO RELATED APPLICATION
This application claims priority from U.S. provisional application No. 60/106,836, filed Nov. 3, 1998, U.S. continuation of application Ser. No. 09/432,441, filed Nov. 2, 1999 now abandoned and continuation of application Ser. No. 09/969,486, filed Oct. 1, 2001 now abandoned.
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Provisional Applications (1)
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60/106836 |
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