Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-07-24
2000-08-01
Dentz, Bernard
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546121, A61K 31435, C07D47104
Patent
active
060967587
DESCRIPTION:
BRIEF SUMMARY
FIELD OF APPLICATION OF THE INVENTION
The invention relates to novel 3-methylimidazopyridines which are to be used in the pharmaceutical industry as active compounds for the production of medicaments.
KNOWN TECHNICAL BACKGROUND
In European Patent Application EP-A-0 033 094, imidazo-[1,2-a]pyridines are described which carry an aryl substituent in the 8-position, which is preferably a phenyl radical, thienyl radical, pyridyl radical or a phenyl radical substituted by chlorine, fluorine, methyl, tert-butyl, trifluoromethyl, methoxy or cyano. Particularly interesting aryl radicals mentioned in EP-A-0 033 094 are the radicals phenyl, o- or p-fluorophenyl, p-chlorophenyl and 2,4,6-trimethylphenyl, of which the radicals phenyl, o- or p-fluorophenyl and 2,4,6-trimethylphenyl are particularly preferred.--In European Patent Applications EP-A-0 204 285, EP-A-0 228 006, EP-A-0 268 989 and EP-A-0 308 917, imidazo[1,2-a]pyridines are described which carry an unsaturated aliphatic radical, in particular a (substituted) alkynyl radical, in the 3-position.--In European Patent Application EP-A-0 266 890, imidazo[1,2-a]pyridines are described which are substituted in the 8-position by an alkenyl, alkyl or cycloalkylalkyl radical.
DESCRIPTION OF THE INVENTION
It has now been found that the compounds described in greater detail below, which differ from the compounds of the prior art, in particular, by the substitution in the 3- or in the 8-position, have surprising and particularly advantageous properties.
The invention relates to compounds of the formula I (see attached formula sheet), in which
R0 is 1-4C-alkyl, hydroxymethyl or trifluoromethyl,
R1 is 1-4C-alkyl,
R2 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy, halogen or trifluoromethyl,
R3 is SO.sub.2 --R6, CO--R7, COO--R8 or CON(R9)R10,
R4 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy, halogen or trifluoromethyl,
R5 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy or halogen,
A is O (oxygen) or NH,
R6 is 1-4C-alkyl, aryl, aryl substituted by R16, R17 and R18, aryl-1-4C-alkyl, aryl-1-4C-alkyl substituted in the aryl moiety by R16, R17 and R18, 1-4C-alkyl completely or partly substituted by fluorine, 1-4C-alkyl substituted by --S(O).sub.n --R19 or the radical --C.sub.q H.sub.2q-2 -aryl, or a cyclic substituent selected from the group consisting of thiolane, thiolane oxide or thiolane dioxide, which is unsubstituted or substituted by hydroxyl,
R7 is aryl, aryl-1-4C-alkyl, aryl substituted by R16, R17 and R18, or aryl-1-4C-alkyl substituted in the aryl radical by R16, R17 and R18,
R8 is 2-4C-alkyl substituted by R11, 1-4C-alkyl substituted by R12, --N.dbd.C(R13)R14, 2-4C-alkyl substituted by R15, aryl, the radical --C.sub.q H.sub.2q-1 or aryl substituted by R16, R17 and R18,
R9 is hydrogen or 1-4C-alkyl,
R10 is 2-4C-alkyl substituted by R11, 1-4C-alkyl substituted by R12, or 1-4C-alkyl,
R11 is 1-4C-alkoxy, 1-4C-alkylcarbonyloxy, hydroxyl, hydroxy-2-4C-alkoxy or 1-4C-alkoxy-1-4C-alkoxy,
R12 is 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyl, carboxyl, mono-1-4C-alkylaminocarbonyl, di-1-4C-alkylaminocarbonyl, thienyl, pyridyl, aryl or aryl substituted by R16, R17 and R18,
R13 is 1-4C-alkyl, phenyl or phenyl-1-4C-alkyl and
R14 is 1-4C-alkyl, phenyl or phenyl-1-4C-alkyl, or in which
R13 and R14 together are a 4-6C-alkylene group,
R15 is phthalimidyl or --S(O).sub.n --R19, where
Aryl is phenyl or naphthyl and
R16 is hydrogen, halogen, nitro, 1-4C-alkyl, 1-4C-alkoxy, trifluoromethyl, hydroxyl, carboxyl, 1-4C-alkoxycarbonyl, cyano, 1-4C-alkoxy completely or partly substituted by fluorine, phenyl, benzoyl, mono- and di-1-4C-alkylamino, amino, 1-4C-alkylcarbonylamino or S(O).sub.n --R19,
R17 is hydrogen, halogen, 1-4C-alkoxy, nitro, carboxyl, 1-4C-alkyl or hydroxyl and
R18 is hydrogen or halogen,
R19 is 1-4C-alkyl,
n is the numbers 0, 1 or 2,
q is the numbers 2 or 3,
Halogen within the meaning of the invention is bromine, chlorine and fluorine.
1-4C-Alkyl represents straight-chain or branched alkyl radicals having 1 to 4 carbon atoms. Examples which may be mentioned are the butyl, isobutyl, sec-butyl, tert-butyl,
Grundler Gerhard
Senn-Bilfinger Jorg
ByK Gulden Lomberg Chemische Fabrik GmbH
Dentz Bernard
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