Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-07-31
1999-04-06
Daus, Donald G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540451, C07K 506, C07K 756, A61K 3805
Patent
active
058918698
DESCRIPTION:
BRIEF SUMMARY
The present invention refers to basic amide derivatives of GE2270 and GE2270-like antibiotics of general formula I ##STR2## wherein: R.sup.1 represents hydrogen, (C.sub.1 -C.sub.4)alkyl or di(C.sub.1 -C.sub.4)alkylamino(C.sub.1 -C.sub.4)alkylene; -C.sub.5)alkylene-carbonyl or a five or six membered nitrogen containing heterocycle ring; -C.sub.4)alkyl-aminocarbonyl, or a NR.sup.3 R.sup.4 group wherein -C.sub.4)alkylene, or di(C.sub.1 -C.sub.4)alkylamino-(C.sub.1 -C.sub.4)alkylene, and -C.sub.4)alkylamino-(C.sub.1 -C.sub.4)alkylene or hydroxy(C.sub.1 -C.sub.4)alkylene, optionally a further heteroatom selected from nitrogen and oxygen, optionally substituted with a group selected from (C.sub.1 -C.sub.4)alkyl, hydroxy(C.sub.1 -C.sub.4)alkylene, di(C.sub.1 -C.sub.4)alkylamino or di(C.sub.1 -C.sub.4)alkylamino(C.sub.1 -C.sub.4)alkylene; five or six membered heterocycle ring optionally containing a further heteroatom selected from oxygen and nitrogen, optionally substituted with a group selected from (C.sub.1 -C.sub.4)alkyl, di(C.sub.1 -C.sub.4)alkylamino, di(C.sub.1 -C.sub.4) alkylamino(C.sub.1 -C.sub.4)alkylene, hydroxy(C.sub.1 -C.sub.4)alkylene and a alk.sub.2 -R.sup.5 group wherein -C.sub.4)alkylamino(C.sub.1 -C.sub.4)alkylene and -C.sub.4)alkylamino(C.sub.1 -C.sub.4)alkylene heteroatoms selected from nitrogen and oxygen, optionally substituted with a group selected from (C.sub.1 -C.sub.4)alkyl, hydroxy(C.sub.1 -C.sub.4)alkylene, di(C.sub.1 -C.sub.4)alkylamino and di(C.sub.1 -C.sub.4)alkylamino(C.sub.1 -C.sub.4)alkylene. ##STR3## represents the antibiotic core portion of formula ##STR4## wherein: W.sup.1 represents phenyl X.sup.1 is methyl and X.sup.2 is hydrogen,
The present invention refers also to the processes for preparing the compounds of formula I and to the carboxylic acid and protected carboxylic acid derivatives of the above compounds, i.e. the precursors of the compounds of formula I wherein the amidic group: ##STR5## is substituted by the group --COOY, wherein Y represents hydrogen or (C.sub.1 -C.sub.4)alkyl.
Antibiotic GE 2270 is prepared by culturing a sample of Planobispora rosea ATCC 53773 or a producing variant or mutant thereof and isolating the desired antibiotic substance from the mycelium and/or the fermentation broth. Planobispora rosea ATCC 53773 was isolated from a soil sample and deposited on Jun. 14, 1988 with the American Type Culture Collection (ATCC), 12301 Parklawn Drive, Rockville, Md. 20852 Maryland, U.S.A., under the provisions of the Budapest Treaty. The strain has been accorded accession number ATCC 53773.
Antibiotic GE 2270 factor A is the main component of the antibiotic GE 2270 complex. Antibiotic GE 2270 factor A and Planobispora rosea ATCC 53773 are described in U.S. Pat. No. 5,139,778.
At present, a number of minor factors of antibiotic GE 2270 have been isolated, namely factors B.sub.1, B.sub.2, C.sub.1, C.sub.2, D.sub.1, D.sub.2, E and T disclosed in European Patent Application Publication no. 451486 which has as its equivalent, U.S. Pat. No. 5,747,295 and factor C.sub.2a is disclosed in European Patent Application Publication no. 529410 which has as its equivalent, U.S. Pat. No. 5,514,649. Also degradation products of GE 2270 factor A are known, namely factors A.sub.1, A.sub.2, A.sub.3 and H disclosed in U.S. Pat. No. 5,139,778.
Among these compounds, factor A, B.sub.2, C.sub.1 and C.sub.2 may be employed as suitable starting materials for preparing the compounds of the present invention.
The above factors may be represented by the following formula II: ##STR6## wherein ##STR7## is a group as above defined wherein W.sup.1 is phenyl and W.sup.2 is hydroxy and determined; determined; and determined.
It should be noted that this formula does not correspond to the one disclosed in the above cited Patent Applications, which formula was assigned on the basis of the physico-chemical data reported therein. As a matter of fact, further studies on the degradation products of the GE2270 factors (P. Tavecchia et al., Jour. of Antib., 47, no. 12 (1994), 1564-1567) have lead to t
REFERENCES:
patent: 5139778 (1992-08-01), Selva et al.
patent: 5202241 (1993-04-01), Selva et al.
patent: 5514649 (1996-05-01), Selva et al.
patent: 5599791 (1997-02-01), Tavecchia et al.
Shimanaica "Novel Antibiotics, Amythiamicins III. Structure Elucidations of Amythiamicins A, B and C" The Journal of Antibiotics, vol. 47 No. 10, pp. 1153-1159, (1994).
Ciabatti Romeo
Lociuro Sergio
Seneci Pierfausto
Biosearch Italia S.p.A.
Daus Donald G.
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