Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2002-06-05
2003-06-24
Peselev, Elli (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C536S008000
Reexamination Certificate
active
06583119
ABSTRACT:
The present invention relates to new aromatic amides, their preparation process and their use as medicaments.
A subject of the invention is the compounds of formula (I):
in which:
Y represents an oxygen atom, or an N-Nalk
1
or NOalk
2
radical in which alk
1
and alk
2
represent an alkyl radical, containing up to to 12 carbon atoms optionally interrupted by one or more oxygen, sulphur or nitrogen atoms, optionally substituted by one or more halogen atoms, by an aryl radical optionally substituted by one or more halogen atoms, by a heterocyclic radical, by one or more
radicals in which Ra and Rb identical or different from one another represent a hydrogen atom, an optionally substituted alkyl radical containing up to 8 carbon atoms, or Ra and Rb form together with the nitrogene atom to which they are joined a heterocycle which can contain in addition another heteroatom chosen from oxygen, sulphur or nitrogen,
X represents a hydrogen atom, a hydroxyl radical, a linear, branched or cyclic alkyl, alkenyl or alkynyl radical optionally interrupted by one or more oxygen, sulphur and or nitrogen atoms, containing up to 12 carbon atoms, optionally substituted by one or more halogen atoms, by a heterocyclic radical, one or more free or esterified OH, C≡N, NO
2
,
radicals in which Ra and Rb, identical or different, represent a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, or Ra and Rb form together with the nitroaen atom to which they are linked a heterocycle optionally containing another heteroatom chosen from nitrogen, sulphur or oxygen, or X represents an alkoxy radical or a
radical in which Re represents an alkyl radical containing up to 8 carbon atoms, optionally substituted by one or more of the substituents indicated above, or X represents an NRcRd radical in which Rc and Rd identical or different, represent a hydrogen atom or an alkyl radical containing up to 12 carbon atoms, optionally substituted by one or more of the substituants indicated above, or Rc and Rd form together with the nitrogen atom to which they are linked a heterocycle optionally containing another heteroatom chosen from nitrogen, sulphur or oxygen,
Z represents a hydrogen or halogen atom or a free, etherified or esterified OH radical,
R
2
represents a hydrogen or halogen atom,
R
3
represents a hydrogen atom, an alkyl radical containing up to 8 carbon atoms or a halogen atom,
R represents a hydrogen atom or an alkyl radical containing up to 4 carbon atoms,
R
1
represents a hydrogen atom, a linear, branched or cyclic alkyl, alkenyl or alkynyl radical containing up to 8 carbon atoms, optionally substituted by one or more halogen atoms, a C≡N radical, an aryl radical containing up to 14 carbon atoms,
R
5
represents a hydrogen atom, an O-alkyl radical containing up to 4 carbon atoms,
either R
6
represents an alkyl or CH
2
—O-alkyl radical, in which alkyl represents an alkyl radical containing up to 8 carbon atoms,
R
7
represents a hydrogen atom or an alkyl radical containing up to 8 carbon atoms,
or R
6
and R
7
form together with the carbon atom which they carry a ring containing up to 8 carson atoms, as well as the salts of the compound of formula (I), when the compounds of formula (I) have a basic function.
As examples of salts there can also be mentioned the salts formed with the following acids: acetic, propionic, trifluoroacetic, maleic, tartaric, methanesulphonic, benzenesulphonic, paratoluenesulphonic, hydrochloric, hydrobromic, hydroiodic, sulphuric, phosphoric and especially stearic, ethylsuccinic or laurylsulphonic acids.
In the definition of the substituents:
the alkyl, alkenyl or alkynyl radical is preferably a methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, terbutyl, decyl or dodecyl, vinyl, allyl, ethynyl, propynyl, cyclobutyl, cyclopentyl or cyclohexyl radical,
the halogen is preferably fluorine or chlorine, or bromine,
the aryl radical is preferably the phenyl radical,
the heterocyclic radical is preferably the pyrrolyl, pyrrolidinyl, pyridyl, pyrazinyl, pyrimidyl, piperidinyl, piperazinyl, quinuclidinyl, oxazolyl, isoxazolyl, morpholinyl, indolyl, imidazolyl, benzimidazolyl, triazolyl, thiazolyl, azetidinyl, aziridinyl radical.
A more particular subject of the invention is the compounds of formula (I) in which Y represents an oxygen atom, those in which Y represents an NO-alkyl radical in which the alkyl radical contains up to 4 carbon atoms, for example those in which Y represents the NOC
2
H
5
radical.
Among the preferred compounds of the invention there can be mentioned the compounds of formula (I) in which X represents an alkyl radical containing up to 4 carbon atoms and in particular the CH
3
radical, or also those in which X represents an NH
2
radical, or also those in which X represents the:
radical.
Among the preferred compounds of the invention, there can be mentioned the compounds of formula (I) in which R
1
represents a
HC≡C—CH
2
—
radical those in which R represents a hydrogen atom, or also those in which R
3
represents a methyl radical, or also those in which Z represents a hydrogen atom, or also those in which R
2
represents a hydrogen atom, or also those in which R
5
represents an OCH
3
radical, or also those in which R
6
represents a methyl radical, or also those in which R
7
represents a methyl radical, those in which R
7
represents an ethyl radical, those in which R
6
and R
7
form with the carbon which carries them a cyclopentyl radical.
Among the preferred compounds of the invention, there can be mentioned the compounds whose preparation is given hereafter in the experimental part and, quite particularly the compounds of 1, 2, 3, 4, 5 and 9.
The products of general formula (I) have a very good antibiotic activity on gram
⊕
bacteria such as staphylococci, streptococci, pneumococci, enterococci, listeria, anaerobes.
The compounds of the invention can therefore be used as medicaments in the treatment of germ-sensitive infections and in particular, in that of staphylococcia such as staphylococcal septicaemias, malignant staphylococcia of the face or skin, pyodermitis, septic or suppurating wounds, boils, anthrax, phlegmons, erysipelas and acne, staphylococcia such as primitive or post-influenzal acute angina, bronchopneumonia, pulmonary suppuration, streptococcia such as acute angina, otitis, sinusitis, scarlatina, pneumococcia such as oneumonia, bronchitis and diphtheria. The products of the present invention are also active against infections caused by germs such as Haemophilus influenzae.
Therefore a subject of the invention is the compounds of formula (I) as medicaments.
A more particular subject of the invention is, as medicaments, the compounds indicated above as preferred compounds.
A subject of the invention is also the pharmaceutical compositions containing at least one of the medicaments defined above as active ingredient.
These compositions can be administered by buccal, rectal, parenteral route, or by local route as a topical application on the skin and mucous membranes, but the preferred administration route is the buccal or injectable route.
They can be solids or liquids and be presented in the pharmaceutical forms commonly used in human medicine, such as for example, plain or sugar-coated tablets, gelatin capsules, granules, suppositories, injectable preparations, ointments, creams, gels; they are prepared according to the usual methods. The active ingredient or ingredients can be incorporated with the excipients usually used in these pharmaceutical compositions such as talc, gum arabic, lactose, starch, magnesium stearate, cocoa butter, aqueous or non-aqueous vehicles, fatty substances of animal or vegetable origin, paraffin derivatives, glycols, various wetting, dispersing or emulsifying agents, preservatives.
These compositions can also be presented in the form of a powder intended to be dissolved extemporaneously in an appropriate vehicle, for example, a pyrogenic sterile water.
The dose administered is variable according to the affection treated, the patient in question,
Haesslein Jean-Luc
Klich Michel
Laurin Patrick
Musicki Branislav
Periers Anne-Marie
Aventis Pharma S.A.
Muserlian Lucas and Mercanti
Peselev Elli
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