Antibiotics called "chloropolysporins B and C", a process for their preparation, and their therapeutic and veterinary use
First Claim
1. An antibiotic substance named chloropolysporin B and pharmaceutically acceptable salts thereof, which, as its sulfate, is characterized by the properties:
- (a) it takes the form of an amphoteric white powder, soluble in water;
(b) specific rotation;
[α
]25 -64.5°
(C=1.04, 0.1 N aqueous hydrochloric acid, sodium D-line);
(c) elemental analysis;
C, 48.33%;
H, 5.05%;
N, 5.48%;
Cl, 5.11%;
S, 1.00%;
(d) on acid hydrolysis it yields;
neutral saccharides;
glucose, mannose and rhamnose;
amino acids;
3-chloro-4-hydroxyphenylglycine and N-methyl-p-hydroxyphenylglycine;
(e) ultraviolet absorption spectrum;
as illustrated in FIG. 1 of the accompanying drawings, having an absorption maximum λ
max at 280 nm (E1cm =51) in a 0.1 N solution of hydrochloric acid, the absorbence, E, being measured at a concentration of 1% w/v;
(f) infrared absorption spectrum;
the infrared absorption spectrum (υ
cm-1) measured on a KBr disc is as shown in FIG. 2 of the accompanying drawings;
(g) nuclear magnetic resonance spectrum;
the nuclear magnetic resonance spectrum (δ
ppm), measured at 270 MHz in deuterated dimethyl sulfoxide using tetramethylsilane as the internal standard, is as illustrated in FIG. 3 of the accompanying drawings;
(h) solubility;
soluble in water and methanol, sparingly soluble in acetone, and insoluble in ethyl acetate, chloroform and benzene;
(i) color reactions;
positive in Ninhydrin and Rydon-Smith reactions;
(j) thin layer chromatography;
Rf value=0.65, using a cellulose sheet (Eastman) as adsorbent and a 15;
10;
3;
12 by volume mixture of butanol, pyridine, acetic acid and water as the developing solvent;
(k) high voltage paper electrophoresis;
using Toyo'"'"'s filter paper No. 51A in a 0.1 M tris-hydrochloric acid buffer solution of pH 7.5 (3300 volt/60 cm, 1 hour);
the migration distance (detected by bioautography with Bacillus subtilis PCI
219) from the origin to the cathode was 4 cm;
(l) molecular formula;
C83 H89 O34 N8 Cl3. 0.5H2 SO4. 10H2 O;
(m) molecular weight;
the molecular weight, measured by FAB-MS, was 1846 (MH+,
1847).
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Accused Products
Abstract
Novel compounds, called chloropolysporins B and C, and salts thereof have antibiotic properties and would appear to be members of the class of glycopeptide antibiotics containing chlorine. They may be produced by cultivating a suitable strain of microorganism of the genus Micropolyspora, especially Micropolyspora sp. SANK 60983 (FERM BP-538). They may be combined with conventional pharmaceutically acceptable carriers or diluents for therapeutic use or incorporated into edible excipients, such as feed or water, for use as a growth-promoting agent, especially for farm animals.
9 Citations
6 Claims
-
1. An antibiotic substance named chloropolysporin B and pharmaceutically acceptable salts thereof, which, as its sulfate, is characterized by the properties:
-
(a) it takes the form of an amphoteric white powder, soluble in water; (b) specific rotation;
[α
]25 -64.5°
(C=1.04, 0.1 N aqueous hydrochloric acid, sodium D-line);(c) elemental analysis; C, 48.33%;
H, 5.05%;
N, 5.48%;
Cl, 5.11%;
S, 1.00%;(d) on acid hydrolysis it yields; neutral saccharides;
glucose, mannose and rhamnose;
amino acids;
3-chloro-4-hydroxyphenylglycine and N-methyl-p-hydroxyphenylglycine;(e) ultraviolet absorption spectrum; as illustrated in FIG. 1 of the accompanying drawings, having an absorption maximum λ
max at 280 nm (E1cm =51) in a 0.1 N solution of hydrochloric acid, the absorbence, E, being measured at a concentration of 1% w/v;(f) infrared absorption spectrum; the infrared absorption spectrum (υ
cm-1) measured on a KBr disc is as shown in FIG. 2 of the accompanying drawings;(g) nuclear magnetic resonance spectrum; the nuclear magnetic resonance spectrum (δ
ppm), measured at 270 MHz in deuterated dimethyl sulfoxide using tetramethylsilane as the internal standard, is as illustrated in FIG. 3 of the accompanying drawings;(h) solubility; soluble in water and methanol, sparingly soluble in acetone, and insoluble in ethyl acetate, chloroform and benzene; (i) color reactions; positive in Ninhydrin and Rydon-Smith reactions; (j) thin layer chromatography; Rf value=0.65, using a cellulose sheet (Eastman) as adsorbent and a 15;
10;
3;
12 by volume mixture of butanol, pyridine, acetic acid and water as the developing solvent;(k) high voltage paper electrophoresis;
using Toyo'"'"'s filter paper No. 51A in a 0.1 M tris-hydrochloric acid buffer solution of pH 7.5 (3300 volt/60 cm, 1 hour);
the migration distance (detected by bioautography with Bacillus subtilis PCI
219) from the origin to the cathode was 4 cm;(l) molecular formula; C83 H89 O34 N8 Cl3. 0.5H2 SO4. 10H2 O; (m) molecular weight; the molecular weight, measured by FAB-MS, was 1846 (MH+,
1847). - View Dependent Claims (2, 3, 4, 5)
-
-
6. A compound of the formula:
- ##STR2## wherein;
R1 represents a ristosamine residue;R2 represents a mannose residue; R3 represents a glucose residue; and R4 represents a rhamnose residue; or a pharmaceutically acceptable salt thereof.
- ##STR2## wherein;
Specification