Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-11-10
2000-03-28
Morris, Patricia L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546120, C07D47104
Patent
active
060433698
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel triazolopyridines of the formula I ##STR2## where R.sup.1 is C.sub.1 -C.sub.20 -alkyl which is unsubstituted or substituted and can be interrupted by from 1 to 4 ether oxygen atoms, or is unsubstituted or substituted phenyl, mercapto or unsubstituted or substituted C.sub.1 -C.sub.20 -alkylthio, or a radical of the formula CH.sub.2 --NL.sup.1 L.sup.2, where L.sup.1 and L.sup.2 are identical or different and independently of one another in each case are hydrogen or C.sub.1 -C.sub.4 -alkyl which may be interrupted by C.sub.1 -C.sub.4 -alkylimino, or together with the nitrogen bonding them are a 5- or 6-membered saturated heterocyclic radical, oxygen atom, or is C.sub.1 -C.sub.4 -alkoxycarbonyl or phenyl, -alkoxycarbonyl and where L.sup.1 and L.sup.2 in each case have the abovementioned meanings, or the radical of a CH-acidic compound, suitable CH-acidic compounds being nitromethane, nitroethane or compounds of the formulae VII to XII ##STR3## where X.sup.1 is cyano, nitro, C.sub.1 -C.sub.4 -alkanoyl, benzoyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, or phenylsulfonyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenoxycarbonyl, carbamoyl, C.sub.1 -C.sub.4 -monoalkylcarbamoyl or C.sub.1 -C.sub.4 -dialkylcarbamoyl, each of which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, or phenylcarbamoyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, or phenyl, benzothiazol-2-yl, benzimidazol-2-yl, 5-phenyl-1,3,4-thiadiazol-2-yl or 2-hydroxyquinoxalin-3-yl, each of which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or nitro, benzimidazol-2-yl,
U.S. Pat. No. 5,101,028 discloses [1,2,4]triazolo[1,5-a]pyridines.
It is an object of the present invention to prepare novel triazolopyridines having a different chemical structure. They should be simple to prepare.
We have found that this object is achieved by the triazolopyridines of the formula I described in greater detail at the beginning.
The exact IUPAC name of the basic structure on which the novel triazolopyridines of the formula I are based is [1,3,4]triazolo[1,5-a]pyridine, with the following numbering of the rings: ##STR4##
The compounds of the formula I can occur in several tautomeric forms which are all included by the patent claims. For example, the compounds where R.sup.5 =hydroxyl can occur, inter alia, in the following tautomeric forms: ##STR5##
If substituted C.sub.1 -C.sub.20 -alkyl radicals occur in formula I, suitable substituents can be eg. unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, carboxyl or C.sub.1 -C.sub.20 -alkoxycarbonyl whose alkyl chain can be interrupted by from 1 to 4 ether oxygen atoms and can be substituted by phenyl or phenoxy. The alkyl radicals here as a rule have 1 or 2 substituents.
If alkyl radicals which are interrupted by ether oxygen atoms occur in the formula I, those alkyl radicals are preferred which are interrupted by 1 or 2 ether oxygen atoms.
If substituted phenyl radicals occur in the formula I, suitable substituents can be eg. C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, in this case in particular chlorine or bromine, or nitro or carboxyl. The phenyl radicals here as a rule have from 1 to 3 substituents.
If R.sup.5 in formula I is a radical of a CH-acidic compound, particular mention should be made of CH-acidic compounds of the formula VII, VIII or X, where phenoxycarbonyl, C.sub.1 -C.sub.2 -monoalkylcarbonyl, phenylcarbamoyl, phenyl, benzimidazol-2-yl, benzothiazol-2-yl or 5-phenyl-1,3,4-thiazol-2-yl,
R.sup.1 and R.sup.3 radicals are eg. methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.
R.sup.1 radicals are furthermore eg. pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, heptyl, 1-ethylpentyl, octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, i
REFERENCES:
Geissler, et al., Preparation of substituted, etc CA 115:114513 1991
BASF - Aktiengesellschaft
Morris Patricia L.
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