Claims
- 1. A compound of the formula ##STR9## wherein R.sub.3 is hydrogen or hydroxyl;
- R.sub.4 is hydrogen or methyl;
- R.sub.7 is CH.sub.2 R.sub.5, C.sub.3 -C.sub.8 -cycloalkyl, --CHR.sub.8 (CH.sub.2).sub.p R.sub.9, --(CH.sub.2).sub.q R.sub.10 or --CH.sub.2 (CH.dbd.CH).sub.r Ar;
- R.sub.5 is hydrogen, C.sub.1 -C.sub.14 -alkyl, --(CH.sub.2).sub.l X(CH.sub.2).sub.m Y
- or C.sub.1 -C.sub.14 -alkyl or --(CH.sub.2).sub.l X(CH.sub.2).sub.m Y having from one to three substituents selected from the group consisting of halo, hydroxyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di(C.sub.1 -C.sub.4 -alkyl)amino and, --N(CH.sub.2).sub.s ;
- R.sub.6 is hydrogen, halo, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- R.sub.8 is C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl;
- R.sub.9 is hydrogen, halo, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, mono- or di(C.sub.1 -C.sub.4 -alkyl)amino, --N(CH.sub.2).sub.s or phenyl;
- R.sub.10 is hydroxyl, cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di(C.sub.1 -C.sub.4 -alkyl)amino or --N(CH.sub.2).sub.s ;
- Ar is phenyl; phenyl having one or two halo, C.sub.1 -C.sub.14 -alkyl, C.sub.1 -C.sub.4 -alkoxy or hydroxyl substituents; or an R.sub.6 -substituted monocyclic aromatic heterocyclic group wherein the monocyclic aromatic heterocyclic group is selected from the group consisting of pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, imidazolyl, pyrazolyl, pyrrolyl, furanyl, oxazolyl, thiazolyl and thienyl;
- X is oxygen or sulfur;
- Y is --X(CH.sub.2).sub.n CH.sub.3, --N(CH.sub.2).sub.s or --N((CH.sub.2).sub.n CH.sub.3).sub.2 ;
- l is 1 or 2;
- m is an integer from 1 to 3;
- n is an integer from 0 to 3;
- p is an integer from 1 to 5;
- q is 2 or 3;
- r is 0 or 1; and
- s is an integer from 2 to 7;
- or a pharmaceutically acceptable salt thereof.
- 2. A compound of the formula ##STR10## wherein R.sub.3 is hydrogen or hydroxyl;
- R.sub.4 is hydrogen or methyl;
- R.sub.11 is --N(CH.sub.3)R.sub.7 or --N(CH.sub.2).sub.s ;
- R.sub.7 is CH.sub.2 R.sub.5, C.sub.3 -C.sub.8 -cycloalkyl, --CHR.sub.8 (CH.sub.2).sub.p R.sub.9, --(CH.sub.2).sub.q R.sub.10 or --CH.sub.2 (CH.dbd.CH).sub.r Ar;
- R.sub.5 is hydrogen, C.sub.1 -C.sub.14 -alkyl, --(CH.sub.2).sub.l X(CH.sub.2).sub.m Y
- or C.sub.1 -C.sub.14 -alkyl or --(CH.sub.2).sub.l X(CH.sub.2).sub.m Y having from one to three substituents selected from the group consisting of halo, hydroxyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di(C.sub.1 -C.sub.4 -alkyl)amino and, --N(CH.sub.2).sub.s ;
- R.sub.6 is hydrogen, halo, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- R.sub.8 is C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl;
- R.sub.9 is hydrogen, halo, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, mono- or di(C.sub.1 -C.sub.4 -alkyl)amino, --N(CH.sub.2).sub.s orphenyl;
- R.sub.10 is hydrogen, cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di(C.sub.1 -C.sub.4 -alkyl)amino or --N(CH.sub.2).sub.s ;
- Ar is phenyl; phenyl having one or two halo, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or hydroxyl substituents; or an R.sub.6 -substituted monocyclic aromatic heterocyclic group wherein the monocyclic heterocyclic group is selected from the group consisting of pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, imidazolyl, pyrazolyl, pyrrolyl, furanyl, oxazolyl, thiazolyl and thienyl;
- X is oxygen or sulfur;
- Y is --X(CH.sub.2).sub.n CH.sub.3, --N(CH.sub.2).sub.s or --N((CH.sub.2).sub.n CH.sub.3).sub.2 ;
- l is 1 or 2;
- m is an integer from 1 to 3;
- n is an integer from 0 to 3;
- p is an integer from 1 to 5;
- q is 2 or 3;
- r is 0 or 1; and
- s is an integer from 2 to 7;
- or a pharmaceutically acceptable salt thereof.
- 3. A compound of claim 1 wherein R.sub.4 is methyl.
- 4. A compound of claim 3 wherein R.sub.3 is hydrogen.
- 5. A compound of claim 3 wherein R.sub.3 is hydroxyl.
- 6. A compound of claim 1 wherein R.sub.4 is methyl, R.sub.7 is CH.sub.2 R.sub.5, and R.sub.5 is as defined in claim 1.
- 7. A compound of claim 3 wherein R.sub.7 is C.sub.3 -C.sub.4 -cycloalkyl.
- 8. A compound of claim 1 wherein R.sub.4 is methyl, R.sub.7 is --CHR.sub.8 (CH.sub.2).sub.p R.sub.9, and R.sub.8, p and R.sub.9 are as defined in claim 1.
- 9. A compound of claim 1 wherein R.sub.4 is methyl, R.sub.7 is --(CH.sub.2).sub.q R.sub.10, and q and R.sub.10 are as defined in claim 1.
- 10. A compound of claim 1 wherein R.sub.4 is methyl, R.sub.7 is --CH.sub.2 (CH.dbd.CH).sub.r Ar, and r and Ar are as defined in claim 1.
- 11. A compound of claim 6 wherein R.sub.5 is hydrogen or C.sub.1 -C.sub.5 -alkyl.
- 12. A compound of claim 11 wherein R.sub.5 is ethyl.
- 13. A compound of claim 2 wherein R.sub.4 is methyl.
- 14. A compound of claim 13 wherein R.sub.3 is hydrogen.
- 15. A compound of claim 13 wherein R.sub.3 is hydroxyl.
- 16. A compound of claim 2 wherein R.sub.4 is methyl, R.sub.11 is --N(CH.sub.3)R.sub.7, and R.sub.7 is as defined in claim 2.
- 17. A compound of claim 2 wherein R.sub.4 is methyl, R.sub.7 is CH.sub.2 R.sub.5, and R.sub.5 is as defined in claim 2.
- 18. A compound of claim 17 wherein R.sub.5 is hydrogen or C.sub.1 -C.sub.5 alkyl.
- 19. A composition useful for the treatment of susceptible bacterial infections comprising an effective antibacterial amount of a compound of claim 1 together with a suitable vehicle.
- 20. A composition useful for the treatment of susceptible bacterial infections comprising an effective antibacterial amount of a compound of claim 2 together with a suitable vehicle.
- 21. A method for treating infections caused by susceptible bacteria which comprises administering an effective amount of a composition of claim 19 to an animal.
- 22. A method for treating infections caused by susceptible bacteria which comprises administering an effective amount of a composition of claim 20 to an animal.
CROSS-REFERENCE TO RELATED APPLICATION
This application is a continuation of application Ser. No. 07/007,832, filed Jan. 28, 1987, now abandoned, which in turn is a continuation-in-part of application Ser. No. 06/824,911, filed Feb. 3, 1986, now abandoned.
US Referenced Citations (11)
Non-Patent Literature Citations (5)
Entry |
Massey et al. "Erythromycylamine", Tetrahedron Letters 1970 (2), 157-160. |
Ryden et al., "N-Substituted Derivatives of Erythromycylamine," J. Med. Chem. 16 (9), 1059-1060 (1973). |
Cockerill et al., "Substituent Effects on the pKa Values and Rates of Hydrolysis of Aryl-methylene-erythromycylamines," J. Chem. Soc. Perkin, II 1973, 173-179. |
Massey et al., "Antibacterial Activity of 9(S)-erythromycylamine-Aldehyde Condensation Products," J. Med. Chem. 17, 105-107 (1974). |
Vince et al., "Binding of N-Substituted Erythromycylamine to Ribosomes," Antimicrobial Agents and Chemotherapy 9 (1), 131-136 (1976). |
Continuations (1)
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7832 |
Jan 1987 |
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Continuation in Parts (1)
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829911 |
Feb 1986 |
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