Antibiotic A-32887 and process for production thereof
AssigneeEli Lilly and Company
InventorsRobert L. Hamill, Marvin M. Hoehn
Life of this patent
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Abstract
Antibiotic A-32887 is produced by submerged aerobic fermentation of Streptomyces albus NRRL 11109. A-32887 is an antibacterial, antiprotozoal, anticoccidial, and insecticidal agent. A-32887 also increases feed-utilization efficiency in ruminants.
Claims4
A compound selected from the group consisting of (1) the acetyl ester derivative of antibiotic A-32887, having an approximate empirical formula of C.sub.50-51 H.sub.82-88 O.sub.18-19, and which in its Na-K salt form has a molecular weight of about 988, a melting point of about 127.degree.-129.degree. C., and an approximate R.sub.f value of 0.40 on silica-gel TLC in benzene:ethyl acetate (1:1), and an infrared absorption spectrum as shown in FIG. 4 of the drawings;
- (2) the n-butyryl ester derivative of antibiotic A-32887 having an approximate empirical formula of C.sub.52-53 H.sub.86-92 O.sub.18-19, and which in its Na-K salt form has a molecular weight of about 1016, a melting point of about 59.degree.-62.degree. C., an approximate R.sub.f value of 0.64 on silica-gel TLC in benzene:ethyl acetate (1:1), and an infrared absorption spectrum as shown in FIG. 5 of the drawings;
- and (3) the pharmaceutically-acceptable salts thereof.
A compound selected from the group consisting of (1) the methyl ether derivative of A-32887, which has a molecular weight of about 960 and an approximate empirical formula of C.sub.49-50 H.sub.82-88 O.sub.17-18, and which in its sodium salt form is a white crystalline compound, when crystallized from n-hexane:ethyl acetate, having a melting point of about 214.degree.-216.degree. C. and having the following characteristics:
- (a) a molecular weight of about 982, as determined by FD mass spectrometry;
- (b) an infrared absorption spectrum in chloroform with significant absorption maxima at the following frequencies (cm.sup.-1):
- 3400 (broad), 2990, 2960, 2930, 2870, 2820, 1725, 1610, 1455, 1407, 1370, 1309, 1282, 1240, 1180, 1158, 1110, 1093, 1082, 1057, 1010, 980, 945, 900, 868, 858, 827, 802, 700, and 653;
- (c) a proton-magnetic-resonance spectrum which indicates the presence of six methoxyl groups;
- (d) a specific rotation as follows:
- [.alpha]sub.D.sup.25 -5.1.degree. (c 1, CHCl.sub.3);
- (e) an X-ray powder diffraction pattern (CuNi, 1.5405 .lambda., d = interplanar spacing in angstroms) as follows:
- ______________________________________ Relative d Intensity ______________________________________ 13.18 50 12.01 50 9.02 100 8.26 100 7.19 80 6.46 50 5.78 20 5.46 20 5.00 30 4.24 20 3.72 20 3.36 05 ______________________________________
- (f) a titratable group in 80% aqueous dimethylformamide with a pK.sub.a value of about 5.4;
- (g) solubility in methanol, ethanol, dimethylformamide, dimethyl sulfoxide, ethyl acetate, chloroform, acetone, and benzene;
- slight solubility in hexane and heptane;
- and insolubility in water;
- (h) an acid function capable of forming salts and ester derivatives;
- and
- (2) the pharmaceutically-acceptable salts of the methyl ether derivative of A-32887.
The method of producing antibiotic A-32887 which comprises cultivating a Streptomyces albus having the essential identifying characteristics of NRRL 11109 in a culture medium containing assimilable sources of carbohydrate, nitrogen, and inorganic salts under submerged aerobic fermentation conditions until a substantial amount of antibiotic activity is produced.
Dependencies are inferred from the claim text.