Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Patent
1988-09-08
1990-09-04
Lee, Lester L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
530317, 426635, A61K 3702, C07K 750, A23K 100
Patent
active
049544837
DESCRIPTION:
BRIEF SUMMARY
The present invention is directed to derivatives of the peptidic moiety of the antibiotic substance called teicoplanin of the following formula I ##STR1## wherein
R represents (C.sub.1 -C.sub.12)alkyl, hydroxy(C.sub.1 -C.sub.12)alkyl, (C.sub.1 -C.sub.3)alkoxy(C.sub.1 -C.sub.12)alkyl, halo(C.sub.1 -C.sub.12)alkyl; a group of formula ##STR2## wherein R.sup.2 and R.sup.3 each independently represents hydrogen or (C.sub.1 -C.sub.4)alkyl groups, or R.sup.2 and R.sup.3 taken together with the adjacent nitrogen atom represent a 5-7 membered aromatic, partially hydrogenated or saturated heterocycle ring which may optionally contain a further heteroatom selected from S, O and N; a group of formula ##STR3## wherein R.sup.2 and R.sup.3 are as defined above and R.sup.4 represents hydrogen or (C.sub.1 -C.sub.4)alkyl; or R represents a group of formula one of the hydrogen atoms of the --(CH.sub.2)--group may be substituted by a methyl group; (C.sub.2 -C.sub.10) alkanoyloxymethyl, phenyl, substituted phenyl, phenyl(C.sub.1 -C.sub.6)alkyl, substituted phenyl(C.sub.1 -C.sub.6)alkyl,
R.sup.1 represents hydrogen or an amino-protecting group,
A, B, and Z each individually represents a hydrogen group,
As used herein the term "alkyl" includes both straight and branched hydrocarbon groups; more particularly, "(C.sub.1 -C.sub.12)alkyl" represents a straight or branched aliphatic hydrocarbon chain of 1 to 12 carbon atoms such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 1-hexanyl, 2-hexanyl, 3-hexanyl, 3,3-dimethyl-1-butanyl, 4-methyl-1-pentanyl; 3-methyl-1-pentanyl, 2,2-dimethyl-3-pentanyl, 2,4-dimethyl-3-pentanyl, 4,4-dimethyl-2-pentanyl, 5-methyl-2-hexanyl, 1-heptanyl, 2-heptanyl, 5-methyl-1-hexanyl, 2-ethyl-1-hexanyl, 2-methyl-3-hexanyl, 1-octanyl, 2-octanyl, 2-cyclopentylethanyl, 1-nonanyl, 2-nonanyl, 1-decanyl, 2-decanyl and 3-decanyl, 1-undecyl, 2-dodecyl and the like, while "(C.sub.1 -C.sub.4)alkyl" represents a straight or branched hydrocarbon chain of 1 to 4 carbon atoms; the term "(C.sub.1 -C.sub.3)alkoxy" represents an alkoxy group of 1 to 3 carbon atoms, i.e. methoxy, ethoxy, n-propyloxy, isopropyloxy.
The term "(C.sub.2 -C.sub.10)alkanoyloxymethyl" refers to alkanoyloxymethyl group wherein the alkanoyl portion is represented by a straight or branched alkanoyl group of 2 to 10 carbon atoms.
Representative examples of (C.sub.2 -C.sub.10)alkanoyloxymethyl groups are: acetyloxymethyl, n-propionyloxymethyl, butyryloxymethyl, 2-methylpropanoyloxymethyl, pentanoyloxymethyl, 2-methylbutanoyloxymethyl, hexanoyloxymethyl, 3-methylpentanoyloxymethyl, 2,2-dimethylpropanoyloxymethyl, pivaloyloxymethyl, 3,3-dimethylbutanoyloxymethyl, 2,2-dimethylpentanoyloxymethyl, and the like. Examples of "5-7 membered aromatic, partially hydrogenated or saturated heterocycle ring" according to the invention are: pyrrolyl, pyridyl, pyrrolidinyl, pyridinyl, piperazinyl, imidazolyl, pyrimidinyl, pyridazyl, oxazolyl, oxazolidinyl, imidazolinyl, pyrazolidinyl, thiazolyl, thiazolinyl, thiazolidinyl, azepinyl, diazepinyl and thiazepinyl and the like.
The term "halo(C.sub.1 -C.sub.12)alkyl" represents mono- or poly-halogenated alkyl group of 1 to 12 carbon atoms wherein the halo atom is chloro, fluoro or bromo.
Examples of halo(C.sub.1 -C.sub.12)alkyl groups are: monochloroethyl, dichloroethyl, trichloroethyl, dichlorofluoroethyl, difluorochloroethyl, difluoroethyl, trifluoroethyl, dichloropropyl, 1,1,1,3,3,3-hexafluoro-2-propyl, monochlorobutyl, difluorobutyl or trifluorobutyl and tetrafluorobutyl, and the like.
The term ".beta.-poly-halo(C.sub.1 -C.sub.12)alkyl" refers in particular to halo(C.sub.1 -C.sub.12)alkyl derivatives having at least a halogen atom in the position-.beta. of the alkyl chain.
The term "substituted phenyl" indicates a phenyl residue which is substituted with one or two substituents selected from chloro, bromo, iodo, (C.sub.1 -C.sub.4)alkyl, hydroxy, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio, nitro, and trifluoromethyl.
Examples of phenyl subs
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patent: 4497802 (1985-02-01), Debono
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Barna et al., J. Am. Chem. Soc., vol. 106, No. 17, pp. 4895-4902 (8/22/1984).
Hunt et al., J. Am. Chem. Soc., vol. 106, pp. 4891-4895 (8/22/1984).
Barna et al., The Journal of Antibiotics, vol. 37, pp. 1204-1208 (Oct. 1984).
Malabarba et al., The Journal of Antibiotics, vol. 37, pp. 988-999 (Sep., 1984).
Cavalleri Bruno
Magni Ambrogio
Malabarba Adriano
Strazzolini Paolo
Trani Aldo
Chan Christina
Gruppo Lepetit S.p.A.
Lee Lester L.
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