O-acyl derivatives of antibiotic EM-49
AssigneeE. R. Squibb & Sons, Inc.
InventorWilliam Lawrence Parker
Life of this patent
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Abstract
Antibiotic EM-49, an antimicrobially active material obtained from the microorganism Bacillus circulans ATCC 21656, is chemically treated to acylate the hydroxyl group, thereby obtaining O-acyl derivatives which are effective against a variety of bacteria and fungi.
Claims33
The O-acetyl derivative of antibiotic EM-49 and acid salts thereof, the hydrochloride having the infrared absorption spectrum as in FIG. 5, the NMR spectrum as in FIG. 6, the approximate elemental analysis of anhydrous material:
- C, 51.10;
- H, 8.00;
- N, 14.90;
- Cl, 11.60;
- the approximate empirical formula C.sub.52 H.sub.97 N.sub.13 O.sub.11 Cl.sub.4 and an approximate molecular weight of 1222.
The tetra(benzyloxycarbonyl) derivative of antibiotic EM-49 having the infrared absorption as in FIG. 1, the NMR spectrum as in FIG. 2, the approximate elemental analysis of anhydrous material:
- C, 61.27;
- H, 6.69;
- N, 11.37;
- the approximate empirical formula C.sub.82 H.sub.115 N.sub.13 O.sub.18 and an approximate molecular weight of 1571.
The tetra(benzyloxycarbonyl)-O-acetyl derivative of antibiotic EM-49, having the infrared absorption spectrum as in FIG. 3, the NMR spectrum as in FIG. 4, the approximate elemental analysis of anhydrous material:
- C, 61.63;
- H, 7.25;
- N, 11.68;
- the approximate empirical formula C.sub.84 H.sub.117 N.sub.13 O.sub.19 and an approximate molecular weight of 1613, and acid salts thereof.
The O-butyryl derivative of antibiotic EM-49 and acid salts thereof, the hydrochloride having the infrared absorption spectrum as in FIG. 7, the approximate elemental analysis of anhydrous material, as the hydrochloride:
- C, 52.45;
- N, 14.40;
- Cl.sup.-, 11.17;
- the approximate empirical formula C.sub.54 H.sub.101 N.sub.13 O.sub.11 Cl.sub.4 and an approximate molecular weight of 1250.
The O-hexanoyl derivative of antibiotic EM-49, and acid salts thereof, having the infrared absorption spectrum as in FIG. 9, the approximate elemental analysis of anhydrous material:
- C, 59.83;
- N, 15.76;
- the approximate empirical formula C.sub.56 H.sub.101 N.sub.13 O.sub.11 and an approximate molecular weight of 1132.
The O-octanoyl derivative of antibiotic EM-49, and acid salts thereof, the hydrochloride having the infrared spectrum as in FIG. 12, the approximate elemental analysis:
- C, 51.97;
- H, 8.37;
- N, 12.96;
- Cl.sup.-, 10.12;
- the approximate empirical formula C.sub.58 H.sub.109 N.sub.13 O.sub.11 Cl.sub.4 and an approximate molecular weight of 1306.
A compound of the formula ##EQU3## wherein Dab is 2,4-diaminobutyric acid, Y is L-leucine or L-phenylalanine;
- X is ##EQU4## R.sup.1 is C.sub.7 H.sub.15 or C.sub.8 H.sub.17 ;
- and R.sup.2 is lower alkanoyl, and acid salts thereof.
Dependencies are inferred from the claim text.