Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Patent
1993-07-01
1997-02-04
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
540451, C07K 756, A61K 3566
Patent
active
055997910
DESCRIPTION:
BRIEF SUMMARY
The present invention is directed to novel amide derivatives of antibiotic GE 2270 having the following formula I ##STR1## wherein R represents: ##STR2## wherein: R.sub.2 represents: -C.sub.4)alkylamino-(C.sub.1 -C.sub.4)alkyl, or di-(C.sub.1 -C.sub.4)alkylamino-(C.sub.1 -C.sub.4)alkyl; 1 to 3 substituents selected from: carboxy, sulfo, phosphono, amino which may be optionally protected with a lower alkoxycarbonyl or a benzyloxycarbonyl group, (C.sub.1 -C.sub.4)alkylamino wherein the alkyl moiety may be optionally substituted with a carboxy group, di-(C.sub.1 -C.sub.4)alkylamino, hydroxy, halo, (C.sub.1 -C.sub.4)alkoxy wherein the alkyl moiety may be optionally substituted with a carboxy group, (C.sub.1 -C.sub.4)alkoxycarbonyl, mercapto, (C.sub.1 -C.sub.4)alkylthio wherein the alkyl moiety may be optionally substituted with a carboxy group, phenyl which may be optionally substituted with 1 to 3 substituents selected from carboxy, sulfo, hydroxy, halo and mercapto, carbamyl, (C.sub.1 -C.sub.6)alkylcarbamyl wherein the alkyl moiety may be optionally substituted with 1 or 2 substituents selected from carboxy, amino, (C.sub.1 -C.sub.4)alkylamino and di-(C.sub.1 -C.sub.4)alkylamino, di-(C.sub.1 -C.sub.4)alkylcarbamyl wherein the alkyl moieties together with the adjacent nitrogen atom may also represent a saturated 5-7 membered heterocyclic ring which may optionally be substituted with a carboxy or a carbamyl group on one of the ring carbons and may optionally contain a further heterogroup selected from O, S and N, benzoylamino wherein the phenyl group may be substituted from 1 to 3 hydroxy group, a nitrogen containing 5-6 membered heterocyclic ring which may be unsaturated, partially saturated or wholly saturated and may contain 1 to 3 further heteroatoms selected from N, S and O wherein one of the carbons of the ring may optionally bear a group carboxy, sulfo, carboxy(C.sub.1 -C.sub.4)alkyl and sulfo(C.sub.1 -C.sub.4)alkyl and the ring nitrogen atom may optionally be substituted by (C.sub.1 -C.sub.4)alkyl, carboxy(C.sub.1 -C.sub.4)alkyl, sulfo(C.sub.1 -C.sub.4)alkyl, and benzyl; wherein the nitrogen atom may be optionally substituted by (C.sub.1 -C.sub.4)alkyl or benzyl and one or two carbons of the ring skeleton may bear a substituent selected from (C.sub.1 -C.sub.4)alkyl, carboxy and sulfo; represent a fully saturated 5-7 membered heterocyclic ring which may optionally contain a further heteroatom selected from O, S and N, and may optionally bear one or two substituents on the ring carbons selected from (C.sub.1 -C.sub.4)alkyl, benzyl, carboxy, sulfo, carboxy(C.sub.1 -C.sub.4)alkyl, and sulfo(C.sub.1 -C.sub.4)alkyl; simultaneously R is methoxymethyl and R.sub.1 is methyl;
This invention includes also a process for preparing the compounds of this invention from the corresponding starting compounds of formula (II) ##STR3## wherein W is a carboxylic function or an activated ester thereof.
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 European Patent Application Publication No. 359062.
Recent studies showed that antibiotic GE 2270 factor A can be represented by the following general formula III ##STR4##
When antibiotic GE 2270 factor A is treated under selective hydrolysis conditions some derivatives named antibiotic GE 2270 factor A.sub.1, A.sub.2 and A.sub.3 are obtained. Said factors A.sub.1, A.sub.2 and A.sub.3 and the hydrolysis process for preparing then is disclosed in
REFERENCES:
patent: 5139778 (1992-08-01), Selva
Selva II The Journal of Antibiotics,44(7)693) (1991).
Lancaster Catalog pp. 589, 590, 1991 Windhan, N.H.
Ciabatti Romeo
Lociuro Sergio
Selva Enrico
Tavecchia Paolo
Dixon J. Michael
Gerstl Robert
Gruppo Lepetit SpA
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