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Details for Patent: 4,939,244

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Details for Patent: 4,939,244

Title: Pseudoaglycones of LL-E33288 antibiotics
Abstract:Degradation products, termed pseudaglycones, of LL-E33288, BBM-1675, FR-900405, FR-900406, PD 114759, PD 115028, CL-1577A, CL-1577B, CL-1577D, CL-1577E and CL-1724 antibiotics/antitumor agents are disclosed anad described.
Inventor(s): Lee; May D.-M. (Monsey, NY)
Assignee: American Cyanamid Company (Stamford, CT)
Filing Date:Jan 30, 1987
Application Number:07/004,153
Claims:1. A process for preparing the pseudoaglycone of an antibiotic of the LL-E33288 complex or the BBM-1675 complex which comprises absorbing the antibiotic onto a column packed with a cation exchange resin in the hydrogen form,

eluting the column with large quantities of methanol to produce the pseudoaglycone of the antibiotic,

removing the resulting pseudoaglycone product from the acidic environment and

isolating the pseudoaglycone by chromatographic purification.

2. The iodinated pseudoaglycone of LL-E33288, when prepared by the process of claim 1, having the following identifying characteristics:

(a) a molecular weight of 1050 (FAB-MS);

(b) a molecular formula: C.sub.40 H.sub.47 N.sub.2 O.sub.15 IS.sub.4 ;

(c) ultraviolet absorption spectra as shown in FIG. I;

(d) an infrared absorption spectrum as shown in FIG. II;

(e) a proton magnetic resonance spectrum as shown in FIG. III;

(f) a carbon-13 magnetic resonance spectrum as shown in FIG. IV, with significant peaks as follows:

(a') a molecular weight of 974 (FAB-MS);

(b') a molecular formula: C.sub.39 H.sub.47 N.sub.2 O.sub.15 IS.sub.4 ;

(c') ultraviolet absorption spectra as shown in FIG. V;

(d') an infrared absorption spectrum as shown in FIG. VI;

(e') a proton magnetic resonance spectrum as shown in FIG. VII;

(f') a carbon-13 magnetic resonance spectrum as shown in FIG. VIII, with significant peaks as follows:

(h) and which, when the product described in (g) is reacted with a methanolic solution of potassium carbonate followed by an excess of acetic anhydride produces a compound having the following physicochemical characteristics:

(a") ultraviolet absorption spectra as shown in FIG. IX;

(b") an infrared absorption spectrum as shown in FIG. X;

(c") a proton magnetic resonance spectrum as shown in FIG. XI;

(d") a molecular formula: C.sub.36 H.sub.40 NO.sub.13 IS.sub.2 ;

(e") and a chemical structure determined by x-ray crystallography to be as shown: ##STR8##

3. A compound pseudoaglycone of BBM-1675, when prepared by the process of claim 1.

4. A brominated pseudoaglycone of LL-E33288.
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