Dihydro derivatives of LL-E33288 antibiotics
AssigneeAmerican Cyanamid Company
InventorMay D. Lee
Life of this patent
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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.
Claims26
A compound dihydro-LL-E33288.alpha..sub.2 -Br of the formula:
- ##STR5##
A compound dihydro-LL-E33288.alpha..sub.2 -I of the formula:
- ##STR6##
A compound dihydro-LL-E33288.alpha..sub.3 -Br of the formula:
- ##STR7##
A compound dihydro-LL-E33288.alpha..sub.3 -I of the formula:
- ##STR8##
A compound dihydro-LL-E33288.beta..sub.1 -Br of the formula:
- ##STR9##
A compound dihydro-LL-E33288.beta..sub.1 -I of the formula:
- ##STR10##
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.
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.
A compound dihydro-LL-E33288.gamma..sub.1 -Br of the formula:
- ##STR11##
A compound dihydro-LL-E33288.gamma..sub.1 -I of the formula:
- ##STR12##
A compound dihydro-LL-E33288.delta..sub.1 -I of the formula:
- ##STR13##
A compound dihydro-BBM-1675 prepared by reducing BBM-1675 with sodium borohydride in the presence of an alkyl iodide.
A compound dihydro-FR-900405 prepared by reducing FR-900405 with sodium borohydride in the presence of an alkyl iodide.
A compound dihydro-FR-900406 prepared by reducing FR-900406 with sodium borohydride in the presence of an alkyl iodide.
A compound dihydro-PD-114759 prepared by reducing PD-114759 with sodium borohydride in the presence of an alkyl iodide.
A compound dihydro-PD-115028 prepared by reducing PD-115028 with sodium borohydride in the presence of an alkyl iodide.
A compound dihydro-CL-1577A. prepared by reducing CL-1577A with sodium borohydride in the presence of an alkyl iodide.
A compound dihydro-CL-1577B prepared by reducing CL-1577B with sodium borohydride in the presence of an alkyl iodide.
A compound dihydro-CL-1577D prepared by reducing CL-1577D with sodium borohydride in the presence of an alkyl iodide.
A compound dihydro-CL-1577E prepared by reducing CL-1577E with sodium borohydride in the presence of an alkyl iodide.
A compound dihydro-CL-1724 prepared by reducing CL-1724 with sodium borohydride in the presence of an alkyl iodide.
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##
Dependencies are inferred from the claim text.