Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1991-05-28
1992-12-15
Robinson, Douglas W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
424118, 435100, 435169, 4352521, 435822, 536 131, A61K 3173, A61K 3500, C07H 1520, C12P 1912, C12P 106, C12N 122, C12R 101
Patent
active
051717409
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a mixture of compounds, two new coumamidine compounds and a process for making them.
BACKGROUND OF THE INVENTION
The compounds of the present invention are similar to the family of compounds LL BM123, disclosed in U.S. Pat. No. 4,007,167. The compounds LL-BM123 are active against a variety of microorganisms and are useful in inhibiting the growth of such bacteria.
The compounds of the present invention are also active against a variety of microorganisms. However, they differ from LL BM123 in that the present compounds do not contain the spermidine substituent, 1,5,10-triazadecane. Further, the antibacterial effects of the new compounds on specific microorganisms, together with their chemical and physical properties, differentiate them from the previously described antibacterial agents.
SUMMARY OF THE INVENTION
The compounds and the mixture of the invention comprise coumamidine gamma 1 (I) and coumamidine gamma 2 (II), which can be represented by the following structural formulas: ##STR1##
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is a hydrogen nuclear magnetic resonance spectrum of coumamidine gamma 1 at 500 MHz in D.sub.2 O.
FIG. 2 is a hydrogen nuclear magnetic resonance spectrum of coumamidine gamma 2 at 500 MHz in D.sub.2 O.
FIG. 3 is an infrared spectrum of coumamidine gamma 1 prepared in a KBr (potassium bromide) pellet.
FIG. 4 is an infrared spectrum of coumamidine gamma 2 prepared in a KBr pellet.
DISCLOSURE OF THE INVENTION
The compounds and mixture of the compounds of the invention are made by cultivating the microorganism Saccharocolvsuora sp. AB 1167L 65. The microorganism produces branched mycelia. Spores are borne in chains on the aerial mycelium. The strain was isolated from soil collected at Russell, Ky. A subculture of this microorganism was deposited in the permanent collection of the Agricultural Research Service at Northern Regional Research Center, United States Department of Agriculture, 1815 North University Street, Peoria, Illinois 61604 U.S.A. The accession number for strain AB 1167L-65 is NRRL 18369.
Coumamidine gamma 1 and coumamidine gamma 2 are produced together by submerged aerobic fermentation (described in detail hereinbelow) of the microorganism Saccharopolyspora sp. strain AB 1167L-65. The compounds are recovered from fermentation broth filtrates of Saccharopolvsoora sp. strain AB 1167L 65 by solid phase extraction with an adsorption resin. Coumamidine gamma 1 and gamma 2 exhibit antibiotic activity against a broad spectrum of bacteria grown under aerobic conditions.
Morphology and Culture Characteristics
The meso isomer of diaminopimelic acid was found in whole-cell hydrolysates. Chromatography of the sugars in whole-cell hydrolysates showed arabinose and galactose as diagnostic sugars. Whole cell hydrolysates can be used to predict cell wall composition, and the combination of morphology and chemical composition can be used to classify aerobic actinomycetes into groups that are recognized based on their cell wall type. Lechevalier and Lechevalier, Inter. J. Syst. Bacteriol., 20, 435-443, (1970), have developed such a classification scheme. The microorganism of this invention has a cell wall of Type IV, i.e., contains meso 2,6-diaminopimelic acid and has a type A whole-cell sugar pattern (arabinose and galactose).
The chemical composition of this microorganism was further characterized by analysis of the cellular lipids. Mycolic acids were not present. The major menaquinone was found to be tetrahydrogenated with nine isoprenoid units [MK 9(H.sub.4)]. Alderson, Goodfellow and Minnikin, J. Gen. Mirobiol., 131, 1671-1679 (1985). The polar lipids were found to contain phosphatidyl choline and phosphatidyl methylethanolamine giving a PIII phospholipid pattern. Lechevalier, De Bievre and Lechevalier, Biochem. System. Ecol., 5, 249-260 (1977). These findings are summarized in Table 1 below.
TABLE 1 ______________________________________
Lipid Analysis of Saccharopolyspora sp. AB 1167L-65
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REFERENCES:
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patent: 4482707 (1984-11-01), Sakakibara et al.
patent: 4515942 (1985-05-01), Iwasaki et al.
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Jackson et al., (1989) J. Antibiot., 42(4), 527-532.
Chem. et al., (1989) J. Antibiot., 42(4), 533-537.
Fernandes et al., (1989) J. Antibiot., 42(4), 538-541.
Chen Randal H.
Jackson Marianna
Karwowski James P.
McAlpine James B.
Theriault Robert J.
Abbott Laboratories
Danckers Andreas M.
Robinson Douglas W.
Weber Jon P.
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