Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-01-31
1998-07-28
Bond, Robert T.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540457, 540458, 546300, A61D 31345, C07D49108
Patent
active
057863504
DESCRIPTION:
BRIEF SUMMARY
This invention relates to novel rifamycin antibiotic derivatives of general formula I: ##STR2## and to the oxidated derivatives thereof of formula Ia: ##STR3## wherein: R represents, halo, hydroxy, thio, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio, (C.sub.1 -C.sub.4)acyloxy, (C.sub.1 -C.sub.4)alkylamino, di(C.sub.1 -C.sub.4)alkylamino or a group of formula: ##STR4## wherein: R.sup.3 represents (C.sub.1 -C.sub.4)alkyl or (C.sub.3 -C.sub.6)cycloalkyl; ##STR5## wherein: R.sup.6 and R.sup.7 independently represent hydrogen or (C.sub.1 -C.sub.4)alkyl or six membered heterocyclic ring, optionally containing one further heteroatom selected from oxygen, nitrogen and sulfur, wherein one of the carbon or nitrogen atoms of the ring is optionally substituted by a (C.sub.1 -C.sub.4)alkyl moiety; optionally containing 1 or 2 nitrogen atoms, of the following formula: ##STR6## wherein: R.sup.8 represents hydrogen or halogen; ring containing one or two nitrogen atoms, wherein the carbon and nitrogen atoms of the ring are optionally substituted with one or two (C.sub.1 -C.sub.4)alkyl moieties; containing one or two heteroatoms selected from oxygen, nitrogen and sulfur, wherein one of the carbon or nitrogen atoms of the ring is optionally substituted by a (C.sub.1 -C.sub.4)alkyl moiety, or a group of formula or two nitrogen atoms, wherein one of the carbon or nitrogen atoms of the ring is optionally substituted by (C.sub.1 -C.sub.4)-alkyl or (C.sub.5 -C.sub.6)cycloalkyl; .dbd.N--(CHR.sup.11)--X--, --NH--(CHR.sup.11)--X--, or --N.dbd.(CR.sup.11)--X--, -C.sub.4)alkylamino or di(C.sub.1 -C.sub.4)alkylamino;
in-the present description, the terms used above in defining the meanings of the substituents R.sup.1 to R.sup.14 are intended to have the meanings commonly assigned to them in the art. Accordingly: containing carbon atoms respectively, such as: containing 1, 2, 3 or 4 carbon, such as: carbon atoms, such as: moiety with 1 to 4 carbon atoms, such as: linear or branched alkyl containing 1 to 4 carbon atoms, such as: two linear or branched alkyl moieties containing 1 to 4 carbon atoms such as: --CH.sub.3,
(C.sub.3 -C.sub.6)cycloalkyl represent a cyclic hydrocarbon moiety containing from .sub.3 to 6 carbon atoms such as:
A five or six membered heterocyclic ring containing one or two heteroatoms selected from oxygen, nitrogen and sulfur (according to the definition of substituents R.sup.6 and R.sup.7 or R.sup.9) is an heterocycle ring such as: ##STR7## wherein W represents hydrogen or the various possible substituents of the 5 or 6 membered heterocycle ring, according to the definitions set out above; atoms, according to the meaninings of R.sup.2 and R.sup.3 taken together, is a group which forms, with the two adjacent carbon atoms, a six membered aromatic heterocyclic ring, such as: ##STR8## wherein the substituents R.sup.8 and R.sup.9 has the same meanings as in formula I; --N.dbd.(CR.sup.11)--X--, is a group which forms, with the adjacent carbon atoms in position 3 and 4,an heterocycle ring such as; ##STR9## wherein R.sup.11 is as above defined; obviously, the double bond between the nitrogen atom and the carbon atom in position 4 is only possible when the rifamycin is in the oxidated form.
Di(C.sub.1 -C.sub.4)alkylamino represents an amino moiety substituted with two linear or branched alkyl groups containing 1, 2, 3 or 4 carbon atoms such as: --N--(CH.sub.3).sub.2, --N(CH.sub.3)(CH.sub.2 --CH.sub.3), --N(CH.sub.2 --CH.sub.3 ).sub.2, --N(CH.sub.3)(CH.sub.2 --CH.sub.2 --CH.sub.3), --N(CH.sub.2 --CH.sub.3)(CH.sub.2 --CH.sub.2 --CH.sub.3), --N(CH.sub.2 --CH.sub.2 --CH.sub.3).sub.2, --CH.sub.2 --CH.sub.3 ), --N( CH.sub.2 --CH.sub.3 )(CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.3), --N( CH.sub.2 --CH.sub.2 --CH.sub.3 )(CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.3), --N( CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.3).sub.2, --N(CH.sub.2 --CH.sub.2 --CH.sub.2
Pharmaceutically acceptable base addition salts of the compounds of formula I are the rifamycin salts formed with alkali metal, earth-alkali metal, (C.sub.1 -C.sub.4)alkylamines
REFERENCES:
Helvetica Chimica Acta vol. 56, No. 7, 1973 pp. 2323-2347 Kump et al.
Journal of Antibiotics vol. 40, No. 12, 1987 (Torro) pp. 1733-1739 Wehrli et al.
Ciabatti Romeo
Denaro Maurizio
Lociuro Sergio
Occelli Emilio
Bond Robert T.
Gruppo Lepetit S.p.A.
Homan Ruth E.
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