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Claims for Patent: RE39071

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Claims for Patent: RE39071

Title:Anhydro-and isomer-a-21978c cyclic peptides
Abstract:Two new groups of A-21978C cyclic peptides, anhydro- and isomer-A21978C peptide derivatives, have antibacterial activity and are useful as intermediates. The two groups are prepared via transpeptidation of the parent cyclic peptides. Pharmaceutical formulations containing the new peptides as active ingredients and methods of treating infections caused by susceptible Gram-positive bacteria with the formulations are also provided.The invention also provides an antibacterial composition containing the new drug substance LY 146032 in substantially pure form.
Inventor(s): Baker; Patrick J. (Greenwood, IN), Debono; Manuel (Indianapolis, IN), Farid; Khadiga Z. (Lebanon, IN), Molloy; R. Michael (Avon, IN)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Application Number:09/547,357
Patent Claims: 1. .[.A.]. .Iadd.An isolated .Iaddend.compound of the formula .Iadd.1 .Iaddend. ##STR00012## in which R is C.sub.5-C.sub.14-alkanoyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen; or a pharmaceutically acceptable salt thereof.Iadd.; and wherein the alanine is D-alanine and the serine is D-serine.Iaddend..

2. .[.A.]. .Iadd.An isolated .Iaddend.compound of the formula .Iadd.2 .Iaddend. ##STR00013## in which R is C.sub.5-C.sub.14-alkanoyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen; or a pharmaceutically acceptable salt thereof.Iadd.; and wherein the alanine is D-alanine and the serine is D-serine.Iaddend..

3. .[.A.]. .Iadd.The .Iaddend.compound of claim 1 wherein R is alkanoyl of the formula ##STR00014## and n is an integer from 3 to 12.

4. The compound of claim 3 wherein R is octanoyl.

5. The compound of claim 3 wherein R is nonanoyl.

6. .[.A.]. .Iadd.The .Iaddend.compound of claim 1 wherein R is decanoyl.

7. .[.A.]. .Iadd.The .Iaddend.compound of claim 2 wherein R is alkanoyl of the formula ##STR00015## and n is an integer from 3 to 12.

8. The compound of claim 7 wherein R is octanoyl.

9. The compound of claim 7 wherein R is nonanoyl.

10. .[.A.]. .Iadd.The .Iaddend.compound of claim 2 wherein R is decanoyl.

11. .[.A.]. .Iadd.The .Iaddend.compound of claim 2 wherein R is undecanoyl.

12. A composition useful for the treatment of bacterial infections comprising an effective antibacterial amount of .[.a.]. .Iadd.the .Iaddend.compound of claim 1 together with a vehicle.

13. A composition useful for the treatment of bacterial infections comprising an effective antibacterial amount of .[.a.]. .Iadd.the .Iaddend.compound of claim 2 together with a vehicle.

14. A method for treating bacterial infections which comprises administering an effective amount of .[.a.]. .Iadd.the .Iaddend.composition of claim 12 to an animal.

15. A method for treating bacterial infections which comprises administering an effective amount of .[.a.]. .Iadd.the .Iaddend.composition of claim 13 to an animal.

.Iadd.16. The compound of claim 6 or 10 wherein R is n-decanoyl..Iaddend.

.Iadd.17. A method for treating bacterial infections which comprises administering an effective amount of the composition of claim 12 or 13 to a human..Iaddend.

.Iadd.18. An antibiotic composition comprised of a combination of a compound of formula 1, a compound of formula 2 and a compound of formula 3, or pharmaceutically acceptable salts thereof, wherein the formula 1 compound is ##STR00016## in which R is a C.sub.10 alkanoyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, and wherein the alanine is D-alanine and the serine is D-serine; the formula 2 compound is ##STR00017## in which R is a C.sub.10 alkanoyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, and wherein the alanine is D-alanine and the serine is D-serine; and the formula 3 compound is an A21978C cyclic peptide of ##STR00018## wherein R.sup.N is n-decanoyl; and wherein the total amount of the compound of formula 1 and the compound of formula 2, or salts thereof, in the combination is less than 6 weight percent..Iaddend.

.Iadd.19. The antibiotic composition of claim 18 wherein the combined total amount of the compound or salt of formulas 1 and 2 is less than or equal to 2.5 weight percent..Iaddend.

.Iadd.20. An antibiotic composition useful for the treatment of bacterial infections comprising a combination of a compound of formula 1, a compound of formula 2 and a compound of formula 3, or pharmaceutically acceptable salts thereof, wherein the formula 1 compound is ##STR00019## in which R is a C.sub.10 alkanoyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, and wherein the alanine is D-alanine and the serine is D-serine; the formula 2 compound is ##STR00020## in which R is C.sub.10 alkanoyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, and wherein the alanine is D-alanine and the serine is D-serine; and the formula 3 compound is an effective antibacterial amount of an A21978C cyclic peptide compound of ##STR00021## wherein R.sup.N is n-decanoyl, in substantially pure form..Iaddend.

.Iadd.21. A method for treating bacterial infections which comprises administering an effective amount of the composition of claim 18 or 20 to an animal..Iaddend.

.Iadd.22. A method for treating bacterial infections which comprises administering an effective amount of the composition of claim 18 or 20 to a human..Iaddend.

.Iadd.23. The method of claim 21, wherein the cyclic peptide compound or its pharmaceutically acceptable salt is administered at an effective amount between about 0.1 and about 100 mg of the compound or its pharmaceutically acceptable salt per kg of the animal..Iaddend.

.Iadd.24. The method of claim 23, wherein the amount is between about 1 and about 30 mg of the compound or its pharmaceutically acceptable salt per kg of the animal..Iaddend.

.Iadd.25. The method of claim 21, wherein the animal is a human and the effective amount is between about 100 mg and about 1 g per day..Iaddend.

.Iadd.26. A pharmaceutical formulation comprising a combination of a compound of formula 1, a compound of formula 2 and a compound of formula 3, or pharmaceutically acceptable salts thereof, wherein the formula 1 compound is ##STR00022## in which R is a C.sub.10 alkanoyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, and wherein the alanine is D-alanine and the serine is D-serine; the formula 2 compound is ##STR00023## in which R is a C.sub.10 alkanoyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, and wherein the alanine is D-alanine and the serine is D-serine; and the formula 3 compound is an A21978C cyclic peptide of ##STR00024## wherein R.sup.N is n-decanoyl; and wherein the total amount of the compound of formula 1 and the compound of formula 2, or salts thereof, in the combination is less than 6 weight percent, and the pharmaceutical formulation further comprises from about 0.1 to about 90 weight percent of the A21978C cyclic peptide of formula 3..Iaddend.

.Iadd.27. The pharmaceutical formulation of claim 26 comprising from about 10 to about 30 weight percent of the cyclic peptide compound or salt of formula 3..Iaddend.

.Iadd.28. The pharmaceutical formulation of claim 26 wherein the combined total amount of the compound or salt of formulas 1 and 2 is less than or equal to 2.5 weight percent..Iaddend.

.Iadd.29. The antibiotic composition of claim 18 or 20, produced by a process comprising separating a combination of a i) a compound of formula 1; or a pharmaceutically acceptable salt thereof, ii) a compound of formula 2; or a pharmaceutically acceptable salt thereof; and iii) a compound of formula 3; or a pharmaceutically acceptable salt thereof from a solution comprising the compound of formula 1, the compound of formula 2 and the compound of formula 3 or salts thereof; wherein the pH level of the solution is less than 4 or above 6..Iaddend.

.Iadd.30. A pharmaceutical composition comprised of a combination of a compound of formula 1, a compound of formula 2 and a compound of formula 3, or pharmaceutically acceptable salts thereof, wherein the formula 1 compound is ##STR00025## in which R is a C.sub.10 alkanoyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, and wherein the alanine is D-alanine and the serine is D-serine; the formula 2 compound is ##STR00026## in which R is a C.sub.10 alkanoyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, and wherein the alanine is D-alanine and the serine is D-serine; and the formula 3 compound is an A21978C cyclic peptide of ##STR00027## wherein R.sup.N is n-decanoyl; and the total amount of the compound of formula 1 and the compound of formula 2, or salts thereof, in the combination is less than 6 weight percent; and wherein an effective dose of the compound or salt of formula 3 is between about 0.1 and about 100 mg/kg of the compound; or its pharmaceutically acceptable salt..Iaddend.

.Iadd.31. The pharmaceutical composition of claim 30 wherein the combined total amount of the compound or salt of formulas 1 and 2 is less than or equal to 2.5 weight percent..Iaddend.
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