Claims
- 1. A compound of the formula ##STR44## wherein X and X' together with the carbon atom to which they are attached is --C=0 or --C.dbd.NOR, R is ##STR45## wherein R'.sub.1 and R'.sub.2 are individually selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl and alkynyl of up to 18 carbon atoms, phenyl, naphthyl and phenylalkyl of 1 to 4 alkyl carbon atoms, each of R'.sub.1 and R'.sub.2 being optionally substituted by at least one member of the group consisting of hydroxy, amino, monoalkylamino of up to 4 carbon atoms, dialkylamino of up to 8 carbon atoms, cyano, acyl and carbamoyl of up to 8 carbon atoms, Y and Y' together with the carbon atom are C=0, B is hydrogen or 0R.sub.4, R.sub.4 is hydrogen or forms with A a carbonate or carbamate, A forms with the carbon which carries it and the carbon in position 10 a double bond, or A is --0R'.sub.4, R'.sub.4 is hydrogen, or forms with B a carbonate, or A is ##STR46## , R'.sub.5 is .dbd.C=0 forming with B a carbamate group, R'.sub.6 is hydrogen or alkyl, --C.sub.6 H.sub.5 --(CH.sub.2).sub.a -- or alkoxy of up to 12 carbon atoms, a is 1, 2, 3 or 4 or ##STR47## R.sub.7 and R.sub.8 are individually hydrogen or alkyl or --C.sub.6 H.sub.5 --(CH.sub.2).sub.a -- of up to 18 carbon atoms, q is an integer between 1 and 6, or A is ##STR48## R.sub.9 and R.sub.10 are hydrogen or alkyl of 1 to 8 carbon atoms, n is an integer between 1 and 6, R.sub.2 is selected from the group consisting of alkyl of 1 to 8 carbon atoms, --C0NH.sub.2, --CONHCOR.sub.11 and --CONHS0.sub.2 R.sub.11, R.sub.11 is a hydrocarbon of 1 to 18 carbon atoms optionally containing at least one heteroatom, R.sub.3 in .alpha. or .beta. position is selected from the group consisting of a) hydrogen, b) alkyl of 1 to 8 carbon atoms, c) ##STR49## R.sub.12 and R.sub.13 are selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, and d) ##STR50## R.sub.14 and R.sub.15 are individually hydrogen or alkyl of 1 to 8 carbon atoms, Z is hydrogen or the remainder of a carboxylic acid of 1 to 18 carbon atoms, the oximes that can be represented by X and X' or Y and Y' can be of syn or anti configuration or its non-toxic, pharmaceutically acceptable acid addition salt.
- 2. A compound of claim 1 wherein X and X' together with carbon to which they are attached form >C.dbd.NOR.
- 3. A compound of claim 1 wherein X and X.sub.1 ' together with the carbon to which they are attached are >C.dbd.O.
- 4. A compound of claim 1 wherein X and X' and Y and Y' together with the carbon to which they are attached are >C.dbd.O.
- 5. A compound of claim 1 wherein R.sub.2 is alkyl of 1 to 4 carbon atoms.
- 6. A compound of claim 1 wherein R.sub.2 is methyl.
- 7. A compound of claim 1 wherein R.sub.3 is a .beta.- or .alpha.-hydrogen.
- 8. A compound of claim 1 wherein A is --OH.
- 9. A compound of claim 1 wherein B is --OH.
- 10. A compound of claim 1 wherein A and B form a cyclic 11,12-carbonate.
- 11. A compound of claim 1 wherein A and B are ##STR51## R'.sub.6 is selected from the group consisting of hydrogen, alkyl, alkoxy and aralkyl of up to 12 carbon atoms and ##STR52## q is an integer of 1 to 6 and R'.sub.7 and R'.sub.8 are individually hydrogen or alkyl or phenylalkyl of up to 18 carbon atoms.
- 12. A compound of claim 11 wherein R'.sub.6 is phenylalkyl of up to 12 carbon atoms.
- 13. A compound of claim 11 wherein R'.sub.6 is (CH.sub.2).sub.4 --C.sub.6 H.sub.5.
- 14. A compound of claim 1 wherein Z is hydrogen.
- 15. A compound of claim 1 selected from the group consisting of 9-[O-[2-(dimethylamino)-ethyl]-oxime] of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl-3-oxo erythromycin, 11,12-dideoxy-3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl-3-oxo-12,11-[oxycarbonyl-[(4-phenylbutyl)-imino]] erythromycin, 9-[O-[(2-methoxy-ethoxy)-methyl]-oxime] of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl 3-oxo erythromycin, 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl 3-oxo erythromycin, cyclic 11,12-carbonate of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl 3-oxo erythromycin, (E) 9-O-[2-[[2-(1-pyrrolidinyl-ethyl]-amino]-ethyl]-oxime of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl 3-oxo-erythromycin 9-O-(3-piperidinyl)-oxime of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl-3-oxo-erythromycin, and (E) 9-O-[2-(dimethylamino)-ethyl]-oxime of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-11-deoxy-10,11-didehydro-6-O-methyl 3-oxo-erythromycin.
- 16. An antibacterial composition comprising an antibactericidally efective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
- 17. A composition of claim 16 wherein in the compound X and X' together with carbon to which they are attached form >C.dbd.NOR.
- 18. A composition of claim 16 wherein in the compound X and X' together with the carbon to which they are attached form >C.dbd.O.
- 19. A method of treating bacterial infections in warm-blooded animals comprising administering to warm-blooded animals an antibactericidally effective amount of at least one compound of claim 1.
- 20. A method of claim 19 wherein in the compound X and X' together with carbon to which they are attached form >C.dbd.NOR.
- 21. A method of claim 19 wherein in the compound X and X' together with the carbon to which they are attached form >C.dbd.O.
- 22. The method of claim 19 wherein the active compound is selected from the group consisting of 9-[O-[2-(dimethylamino)-ethyl]]-oxime] of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl-3-oxoerythromycin, 11,12-dideoxy-3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl-3-oxo-12,11-[oxycarbonyl-[(4-phenylbutyl)-imino]] erythromycin, 9-[O-[(2-methoxy-ethoxy)-methyl]-oxime] of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl 3-oxo erythromycin, 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl 3-oxo erythromycin, cyclic 11,12-carbonate of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl 3-oxo erythromycin, (E) 9-O-[2-[[2-(1-pyrrolidinyl-ethyl]-amino]-ethyl]-oxime of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl 3-oxo erythromycin, 9-O-(3-piperidinyl)-oxime of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-6-O-methyl-3-oxo-erythromycin, and (E) 9-O-[2-(dimethylamino)-ethyl]-oxime of 3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)-oxy]-11-deoxy-10,11-didehydro-6-O-methyl 3-oxo-erythromycin.
Priority Claims (3)
Number |
Date |
Country |
Kind |
90-14499 |
Nov 1990 |
FRX |
|
91-06333 |
May 1991 |
FRX |
|
91-10728 |
Aug 1991 |
FRX |
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PRIOR APPLICATION
This application is a continuation of U.S. patent application Ser. No. 958,235, filed Oct. 8, 1992, now abandoned, which is a divisional application of U.S. patent application Ser. No. 793,864 filed Nov. 18, 1991, both now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4680386 |
Morimoto et al. |
Jul 1987 |
|
4857641 |
Hauske |
Aug 1989 |
|
Divisions (1)
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Number |
Date |
Country |
Parent |
793864 |
Nov 1991 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
958235 |
Oct 1992 |
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