Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-05-17
1997-03-18
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514275, 544330, 544331, 544332, 544295, 544296, 544238, C07D23942, A61K 31505
Patent
active
056123400
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/EP 94/03150, filed Sep. 21, 1994.
The invention relates to N-phenyl-2-pyrimidineamine derivatives, to processes for the preparation thereof, to medicaments comprising those compounds, and to the use thereof in the preparation of pharmaceutical compositions for the therapeutic treatment of warm-blooded animals.
The invention rehtes to N-phenyl-2-pyrimidineamine derivatives of formula I ##STR2## wherein R.sub.1 is naphthyl, fiuorenyl, anthracenyl or a substituted cyclic radical, the cyclic radical being bonded to a ring carbon atom in each case and being selected from phenyl, pyridyl, 1H-indolyl, pyrazinyl, thiazolyl, pyrimidinyl, pyridazinyl and imidazolyl, and the substituents of the above-mentioned phenyl radical being selected from hydroxy, halogen, nitro, cyano, unsubstituted or halogen-substituted lower alkoxy, from a radical of formula II amino group is free, lower alkylated or lower alkanoylated, from a radical of formula III unsubstituted or amino- or hydroxy-substituted lower alkyl, from a radical of formula IV alkyl or amino-lower alkyl, or wherein --NH--(CH.sub.2).sub.2 13 , and from a radical of formula V wherein by imidazolyl, guanidyl, lower alkylamino-carbonylamino, amidino, di-lower alkylamino-cyclohexyl, piperazinyl, carboxy, lower alkoxycarbonyl, carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, dihydroxyphosphoryloxy or by formylpiperazinyl, and the substituents of the other above-mentioned cyclic radicals being selected from hydroxy, halogen, cyano, amino-lower alkyl, unsubstituted or halogen-substituted lower alkoxy, phthalimido-substituted lower alkyl, from a radical of the above-mentioned formulae II, III or IV and from a radical of formula VI alkyl, or wherein amino, lower alkylamino, di-lower alkylamino, lower alkanoylamino, imidazolyl, guanidyl, lower alkyl-amino-carbonylamino, amidino, di-lower alkylamino-cyclohexyl, piperazinyl, formylpiperazinyl, carboxy, lower alkoxycarbonyl, carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, dihydroxyphosphoryloxy or by glycylamido; and VII alkyl-hydroximino, aromatic, aromatic-aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, heterocyclic or heterocyclic-aliphatic radical,
Naphthyl R.sub.1 is 1-naphthyl or 2-naphthyl.
Anthracenyl R.sub.1 is preferably 9-anthracenyl.
Fluorenyl R.sub.1 is preferably 2-fluorenyl.
A substituted phenyl radical R.sub.1 can have several substituents, but especially not more than 3 and, especially in the case of relatively large substituents, preferably only one substituent, which substituents are principally in the para- (or 4-position) anct/or preferably meta-position (or 3-position). The other above-mentioned substituted cyclic radicals R.sub.1 generally have up to two and preferably only one substituent, which is especially in the rneta- or para-position with respect to the bonding site of the cyclic radical R.sub.1.
Pyridyl bonded to a ring carbon atom is 2- or preferably 4- or 3-pyridyl, especially 4-pyridyl. In a mono-substituted pyridyt radical R.sub.1, the substituent is preferably in the ortho-position with respect to the pyridine nitrogen.
1H-indolyl bonded to a carbon atom of the five-membered ring is 1H-indol-2-yl or preferably 1H-indol-3-yl. In mono-substituted 1H-indolyl, the substituent is preferably in the 1-position, that is to say, at the nitrogen.
Halogen in a radical R.sub.1 is preferably chlorine or fluorine.
Halogen-substituted phenyl R.sub.1 is preferably 2-, 3- or 4-chloro-phenyl, 2,4-, 3,4- or 2,5- dichloro-phenyl or 2,3,4-trichloro-phenyl
Unsubstituted or halogen-substituted lower alkoxy as substituent of a substituted phenyl radical R1 is preferably methoxy, ethoxy or trifiuoro-methoxy.
A radical of formula II is, for example, a radical wherein m is 1 and R.sub.3 is hydrogen, that is to say, carboxy.
A radical of formula III is, for example, a radical wherein R.sub.4 is hydrogen and R.sub.5 is hydrogen, .omega.-amino-alkyl having 2 or 3 carbon atoms or .omega.-hydroxy-alkyl having 2 or 3 carbon atoms, that is to say, carbamoyl, 2-amino-ethyl, 2-hydroxy-ethy
REFERENCES:
patent: 4725600 (1988-02-01), Takaya et al.
patent: 4966622 (1990-10-01), Rempfler et al.
patent: 5159078 (1992-10-01), Rempfler et al.
Ciba-Geigy Corporation
Ford John M.
Kaiser Karen G.
Mathias Marla J.
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