US 4,539,203 AGranted

CL-1577D And CL-1577E antibiotic/antitumor compounds, their production and use

AssigneeWarner-Lambert Company

InventorsAlex J. Brankiewicz, Richard H. Bunge, James C. French, Gerard C. Hokanson, Timothy R. Hurley, John P. Schaumberg

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Abstract

Compounds CL-1577D and CL-1577E are prepared by cultivation of a purified isolate of Actinomycete designated ATCC 39363 in a culture medium having assimilable sources of carbon and nitrogen. The compounds are effective antimicrobial agents and possess cytotoxic activity against L1210 murine leukemia cells and P388 murine leukemia cells.

Claims8

Dependent claims

Sulfur-containing antibiotic compounds CL-1577D or CL-1577E Compound CL-1577D having the molecular formula C.sub.55 H.sub.94 N.sub.4 O.sub.29 S.sub.4 characterized by the following properties:

(a) an ultraviolet absorption spectrum in methanol having absorption maxima at 320 (a=9.48), 281 (a=12.76), 252 (a=21.74), and 212 (a=22.48) nanometers;
(b) an infrared absorption spectrum in chloroform having absorption peaks at 2939, 1733, 1679, 1598, 1527, 1466, 1409, 1374, 1312, 1252, 1158, 1123, 1075, 1023, 989, and 963 reciprocal centimeters;
and
(c) a 200 MHz nuclear magnetic resonance spectrum in deuterochloroform having principal signals at 1.10 (doublet), 1.23-1.40 (multiplet), 1.42-2.08 (multiplet), 2.10 (singlet), 2.00-2.55 (multiplet), 2.60-2.87 (multiplet), 3.39 (singlet), 3.30-4.16 (multiplet), 3.77 (singlet), 3.86 (singlet), 3.95 (singlet), 4.41-4.70 (multiplet), 4.97 (doublet), 5.21 (multiplet), 5.46 (multiplet), 5.67-5.91 (multiplet), 6.17 (singlet), 6.39 (multiplet), 7.47 (singlet), 8.58 (singlet), and 11.70 (singlet) parts per million downfield from tetramethylsilane;
Compound CL-1577E having the molecular formula C.sub.55 H.sub.94 N.sub.4 O.sub.30 S.sub.4 characterized by the following properties
(a) an ultraviolet absorption spectrum in methanol having absorption maxima at 320 (a=10.04), 282 (a=13.58), 253 (a=22.08), and 213 (a=22.30) nanometers;
(b) an infrared absorption spectrum in chloroform having absorption peaks at 2939, 1734, 1679, 1601, 1527, 1466, 1410, 1376, 1312, 1249, 1181, 1158, 1121, 1078, 1040, 1017, and 954 reciprocal centimeters;
and
(c) a 200 MHz nuclear magnetic resonance spectrum in deuterochloroform having principal signals at 1.09 (doublet), 1.15-1.50 (multiplet), 1.50-2.10 (multiplet), 2.20-2.40 (multiplet), 2.50 (singlet), 2.65-2.90 (multiplet), 2.78 (singlet), 3.39 (singlet), 3.30-4.10 (multiplet), 3.77 (singlet), 3.87 (singlet), 3.97 (singlet), 4.18 (singlet), 4.40-4.90 (multiplet), 5.00-5.30 (multiplet), 5.33-5.47 (multiplet, 5.60-5.95 (multiplet), 6.22 (singlet), 6.60 (multiplet), 7.56 (singlet), 8.62 (singlet), and 11.93 (singlet) parts per million downfield from tetramethylsilane.

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Dependencies are inferred from the claim text.

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Abstract

Sulfur-containing antibiotic compounds CL-1577D or CL-1577E Compound CL-1577D having the molecular formula C.sub.55 H.sub.94 N.sub.4 O.sub.29 S.sub.4 characterized by the following properties:

(a) an ultraviolet absorption spectrum in methanol having absorption maxima at 320 (a=9.48), 281 (a=12.76), 252 (a=21.74), and 212 (a=22.48) nanometers;
(b) an infrared absorption spectrum in chloroform having absorption peaks at 2939, 1733, 1679, 1598, 1527, 1466, 1409, 1374, 1312, 1252, 1158, 1123, 1075, 1023, 989, and 963 reciprocal centimeters;
and
(c) a 200 MHz nuclear magnetic resonance spectrum in deuterochloroform having principal signals at 1.10 (doublet), 1.23-1.40 (multiplet), 1.42-2.08 (multiplet), 2.10 (singlet), 2.00-2.55 (multiplet), 2.60-2.87 (multiplet), 3.39 (singlet), 3.30-4.16 (multiplet), 3.77 (singlet), 3.86 (singlet), 3.95 (singlet), 4.41-4.70 (multiplet), 4.97 (doublet), 5.21 (multiplet), 5.46 (multiplet), 5.67-5.91 (multiplet), 6.17 (singlet), 6.39 (multiplet), 7.47 (singlet), 8.58 (singlet), and 11.70 (singlet) parts per million downfield from tetramethylsilane;
Compound CL-1577E having the molecular formula C.sub.55 H.sub.94 N.sub.4 O.sub.30 S.sub.4 characterized by the following properties
(a) an ultraviolet absorption spectrum in methanol having absorption maxima at 320 (a=10.04), 282 (a=13.58), 253 (a=22.08), and 213 (a=22.30) nanometers;
(b) an infrared absorption spectrum in chloroform having absorption peaks at 2939, 1734, 1679, 1601, 1527, 1466, 1410, 1376, 1312, 1249, 1181, 1158, 1121, 1078, 1040, 1017, and 954 reciprocal centimeters;
and
(c) a 200 MHz nuclear magnetic resonance spectrum in deuterochloroform having principal signals at 1.09 (doublet), 1.15-1.50 (multiplet), 1.50-2.10 (multiplet), 2.20-2.40 (multiplet), 2.50 (singlet), 2.65-2.90 (multiplet), 2.78 (singlet), 3.39 (singlet), 3.30-4.10 (multiplet), 3.77 (singlet), 3.87 (singlet), 3.97 (singlet), 4.18 (singlet), 4.40-4.90 (multiplet), 5.00-5.30 (multiplet), 5.33-5.47 (multiplet, 5.60-5.95 (multiplet), 6.22 (singlet), 6.60 (multiplet), 7.56 (singlet), 8.62 (singlet), and 11.93 (singlet) parts per million downfield from tetramethylsilane.

6 more elements