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Details for Patent: 5,037,651

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Details for Patent: 5,037,651

Title: Dihydro derivatives of LL-E33288 antibiotics
Abstract:Dihydro derivatives of LL-E33288, BBM-1075 FR-900405, FR-900406, PD 114759, PD 115028, CL-1577A, CL-1577B, CL-1577D, CL-1577E and CL-1724 antibiotics/antitumor agents are disclosed and described, including the degradation product of LL-E33288 antibiotics/antitumor agents dihydro-LL-E33288-pseudoaglycone.
Inventor(s): Lee; May D. (Monsey, NY)
Assignee: American Cyanamid Company (Stamford, CT)
Filing Date:Jan 30, 1987
Application Number:07/004,154
Claims:1. A compound dihydro-LL-E33288.alpha..sub.2 -Br of the formula: ##STR5##

2. A compound dihydro-LL-E33288.alpha..sub.2 -I of the formula: ##STR6##

3. A compound dihydro-LL-E33288.alpha..sub.3 -Br of the formula: ##STR7##

4. A compound dihydro-LL-E33288.alpha..sub.3 -I of the formula: ##STR8##

5. A compound dihydro-LL-E33288.beta..sub.1 -Br of the formula: ##STR9##

6. A compound dihydro-LL-E33288.beta..sub.1 -I of the formula: ##STR10##

7. A compound dihydro-LL-E33288.beta..sub.2 -Br prepared by reducing LL-E33288.beta..sub.2 -Br with sodium borohydride in the presence of an alkyl iodide.

8. A compound dihydro-LL-E33288.beta..sub.2 -I prepared by reducing LL-E33288.beta..sub.2 -I with sodium borohydride in the presence of an alkyl iodide.

9. A compound dihydro-LL-E33288.gamma..sub.1 -Br of the formula: ##STR11##

10. A compound dihydro-LL-E33288.gamma..sub.1 -I of the formula: ##STR12##

11. A compound dihydro-LL-E33288.delta..sub.1 -I of the formula: ##STR13##

12. A compound dihydro-BBM-1675 prepared by reducing BBM-1675 with sodium borohydride in the presence of an alkyl iodide.

13. A compound dihydro-FR-900405 prepared by reducing FR-900405 with sodium borohydride in the presence of an alkyl iodide.

14. A compound dihydro-FR-900406 prepared by reducing FR-900406 with sodium borohydride in the presence of an alkyl iodide.

15. A compound dihydro-PD-114759 prepared by reducing PD-114759 with sodium borohydride in the presence of an alkyl iodide.

16. A compound dihydro-PD-115028 prepared by reducing PD-115028 with sodium borohydride in the presence of an alkyl iodide.

17. A compound dihydro-CL-1577A. prepared by reducing CL-1577A with sodium borohydride in the presence of an alkyl iodide.

18. A compound dihydro-CL-1577B prepared by reducing CL-1577B with sodium borohydride in the presence of an alkyl iodide.

19. A compound dihydro-CL-1577D prepared by reducing CL-1577D with sodium borohydride in the presence of an alkyl iodide.

20. A compound dihydro-CL-1577E prepared by reducing CL-1577E with sodium borohydride in the presence of an alkyl iodide.

21. A compound dihydro-CL-1724 prepared by reducing CL-1724 with sodium borohydride in the presence of an alkyl iodide.

22. A compound dihydro-LL-E33288-pseudoaglycone, prepared by treating a dilute methanolic solution of LL-E33288.gamma..sub.1 -I with an ion exchange resin, giving LL-E33288-pseudoaglycone which is then reacted with an alkyl iodide in ethanol cooled to ice bath temperature, followed by reaction with ethanolic sodium borohydride, decomposition with acetic acid, precipitation from ethyl acetate solution with hexane and purification by chromatography, giving the dihydro-LL-E33288-pseudoaglycone having the following characteristics:

a) an ultraviolet absorption spectrum: as shown in FIG. I (methanol);

b) an infrared absorption spectrum: as shown in FIG. II (KBr disc);

c) a proton magnetic resonance spectrum: as shown in FIG. III (300MHz, CDCl.sub.3); and

d) a carbon-13 magnetic resonance spectrum: as shown in FIG. IV (75MHz, CDCl.sub.3) of the formula: ##STR14##

23. A method for treating bacterial infections in warm-blooded animals which comprises administering to said animals an antibacterially effective amount of a compound selected from any one of claims 1-22.

24. A method for treating tumors in warm-blooded animals which comprises administering to said animals an oncolytic amount of a compound selected from any one of claims 1-22.

25. A composition of matter in dosage unit form, comprising an antibacterially effective amount of a compound selected from any one of claims 1-22 in association with a pharmaceutically acceptable carrier.

26. A process for producing the compounds of any one of claims 1-22 which comprises adding an alkyl iodide to an ethanolic solution of the antibiotic selected from the group consisting of LL-E33288.alpha..sub.2.sup.Br, LL-E33288.alpha..sub.2.sup.I, LL-E33288.alpha..sub.3.sup.Br, LL-E33288.alpha..sub.3.sup.I, LL-E33288.beta..sub.1.sup.Br, LL-E33288.beta..sub.1.sup.I, LL-E33288.beta..sub.2.sup.Br, LL-E33288.beta..sub.2.sup.I, LL-E33288.gamma..sub.1.sup.Br, LL-E33288.gamma..sub.1.sup.I, LL-E33288.delta..sup.I, BBM-1675, FR-900405, FR-900406, PD-114759, PD-115028, CL-1577A, CL-1577B, CL-1577D, CL-1577E, CL-1524 or LL-E33288 pseudoaglycone, cooling the solution to ice-bath temperature, adding an ethanolic solution of sodium borohydride, decomposing the borate complex by the addition of acetic acid, precipitation from an ethyl acetate solution by the addition of hexane and purification by chromatography.
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