Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1999-02-11
2000-12-19
Peselev, Elli
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
536 74, 546152, 546348, A61K 3170, C07H 1708, C07D21500
Patent
active
061627933
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new derivatives of erythromycin, their preparation process and their use as antibiotics.
A subject of the invention is the compounds of formula (I): ##STR3## in which R represents a hydrogen atom, an alkyl containing up to 12 carbon atoms, optionally substituted by a halogen atom or a (CH.sub.2).sub.m Ar radical or a ##STR4## radical, in which m represents an integer comprised between 1 and 8, n and p, identical or different, represent an integer comprised between 0 and 6, A and B, identical or different, represent a hydrogen or a halogen atom or an alkyl radical containing up to 8 carbon atoms and Ar represents an aryl or heteroaryl radical, optionally substituted, and Z represents a hydrogen atom or the remainder of a carboxylic acid containing up to 18 carbon atoms.
In the definition of the substituents, the alkyl radical can be a methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl or terbutyl, cyclobutyl, cyclopentyl, cyclohexyl, decyl or dodecyl radical. The halogen is preferably a fluorine, chlorine or bromine atom. The aryl radical can be a phenyl or naphthyl radical. The heteroaryl radical can be a thienyl, furyl, pyrolyl, thiazolyl, oxazolyl, imidazolyl, thiadiazolyl, pyrazolyl or isopyrazolyl radical, a pyridyl, pyrimidyl, pyridazinyl or pyrazinyl radical, or also an indolyl, benzofuranyl, benzothiazyl or quinolinyl radical. The aryl or heteroaryl radical can be substituted by one or more substituents chosen from the group constituted by hydroxyl radicals, halogen atoms, NO.sub.2 radicals, C.tbd.N radicals, alkyl, alkenyl or alkynyl, O-alkyl, O-alkenyl or O-alkynyl, S-alkyl, S-alkenyl or S-alkynyl and N-alkyl, N-alkenyl or N-alkynyl radicals, containing up to 12 carbon atoms optionally substituted by one or more halogen atoms, the ##STR5## radical, R.sub.a and R.sub.b, identical or different, representing a hydrogen atom or an alkyl radical containing up to 12 carbon atoms, the ##STR6## radical, R.sub.3 representing an alkyl radical containing up to 12 carbon atoms, or an optionally substituted aryl or heteroaryl radical, carboxylic aryl, O-aryl or S-aryl radicals or heterocyclic aryl, O-aryl or S-aryl radicals with 5 or 6 members containing one or more heteroatoms, optionally substituted by one or more of the substituents mentioned below.
As the preferred heterocycle radical, the following radicals can be mentioned: ##STR7## and the heterocyclic radicals envisaged in the European Patent Applications 487411, 596802, 676409 and 680967.
The radicals can be substituted by one or more of the substituents indicated above.
A more particular subject of the invention is the compounds of formula (I) in which Z represents a hydrogen atom, the compounds of formula (I) in which R represents a hydrogen atom, the compounds of formula (I) in which R represents (CH.sub.2).sub.m Ar, m and Ar retaining the same meaning as previously, and in particular those in which R represents a (CH.sub.2).sub.m,Ar radical, in which m' represents the number 3, 4, 5 or 6, such as, for example, those in which Ar represents a 4-quinolinyl radical optionally substituted on one and/or the other of the 2 quinoline rings and quite especially those in which Ar represents a non-substituted 4-quinolinyl radical, or also the compounds of formula (I) in which Ar represents a radical: ##STR8## optionally substituted on one and/or the other of the 2 rings and quite especially those in which the Ar radical is not substituted.
A quite particular subject of the invention is the compounds whose preparation is given hereafter in the experimental part and in particular the compound of Example 4.
The products of general formula (I) have a very good antibiotic activity on gram .sup..sym. bacteria such as staphylococci, streptococci, pneumococci.
The compounds of the invention can therefore be used as medicaments in the treatment of infections caused by susceptible germs and in particular, in that of staphylococcia, such as staphylococcal septicemias, malignant staphylococcia of the face or skin, pyodermatitis, septic
REFERENCES:
patent: 5527780 (1996-06-01), Agowidas et al.
patent: 5543400 (1996-08-01), Agowidas et al.
patent: 5656607 (1997-08-01), Agowidas et al.
patent: 5747467 (1998-05-01), Agowidas et al.
Agouridas Constantin
Chantot Jean-Francois
Denis Alexis
Pejac Jean-Marie
Hoechst Marion Roussel
Peselev Elli
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