Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-09-27
1995-09-26
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
5142278, 5142358, 514252, 514255, 540544, 544 60, 544121, 544295, 544360, 544367, 544372, A61K 31505, A61K 31495, C07D24104, C07D23928
Patent
active
054534232
DESCRIPTION:
BRIEF SUMMARY
This is the national stage of PCT/EP92/00724, filed Apr. 1, 1992.
The present invention relates to heterocyclic amines, a process for the preparation thereof and pharmaceutical compositions containing them.
More precisely, the invention relates to compounds of formula (I): ##STR2## the single enantiomeric and diastereoisomeric forms thereof, the racemic mixtures thereof and the salts thereof with pharmaceutically acceptable acids and bases, wherein: --CH.sub.2 NHCO--, or --CH.sub.2 NHCS-- group; C.sub.1 -C.sub.6 alkoxy groups; benzhydryl optionally substituted by halogen atoms; phenyl optionally substituted by halogen atoms; (3-hydroxy-2-pyridyl)methyl; 5- or 6-membered heterocycle with 1-3 nitrogen atoms, which can possibly be substituted by 1 or 2 amino groups, mono-C.sub.1 -C.sub.6 -alkylamino, mono-C.sub.3 -C.sub.7 -alkenyl- or mono-C.sub.3-C.sub.7 -alkinylamino, di-C.sub.1 -C.sub.6 -alkylamino, (C.sub.1-C.sub.6)alkyl(C.sub.3-C.sub.7)alkenylamino, piperidin-1-yl, morpholin-4-yl, pyrrolidin-1-yl; with the carbon atom which they are linked to, form a C.sub.3 -C.sub.6 cycloalkyl group; C.sub.1 -C.sub.4 alkyl alcohols or amide, sulfonamide or hydroxyamido derivatives thereof, respectively of formulae CONRcRd, CONHSO.sub.2 Rf and CONRgOH, wherein Rc and Rd, which can be the same or different, are hydrogen, C.sub.1 -C.sub.6 alkyl, benzyl, ortho-, meta- or para-aminopyridino, or, taken together with the nitrogen atom, form a pyrrolidino, piperidino, morpholino, 4-thiomorpholino, 4,5-dithiaazepino, C.sub.1 -C.sub.4 -4-alkylpiperazino, imidazolyl group; Rf is C.sub.1 -C.sub.4 -alkyl, trihalomethyl, tolyl or phenyl, possibly substituted by halogen atoms; Rg is H or C.sub.1 -C.sub.4 -alkyl; C.sub.5 -C.sub.6 cycloalkyl or phenyl groups;
The present invention also relates to the compounds of formula (I), wherein, when Y is different from a bond, A is halogen (Cl, Br or I), as intermediates products.
Examples of C.sub.1 -C.sub.3 --, C.sub.1 -C.sub.4 - or C.sub.1 -C.sub.6 -alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, n-hexyl.
Examples of 5- or 6-membered heterocyclic groups with 1-3 nitrogen atoms, which can optionally be substituted with 1-2 amino groups, are: 2-pyridyl, (3-hydroxy-2-pyridinyl)methyl, [2,6-bis(diethylamino) -4-pyrimidinyl], [2,6-bis(allylamino)-4-pyrimidinyl], [2,6-bis(amino)-4-pyrimidinyl], [2,6-bis(pyrrolidin-1-yl)-4-pyrimidinyl], [2,6-bis(diethylamino)-5-benzoyl-4-pyrimidinyl], [2,6-bis(diethylamino)-5-acetyl-4-pyrimidinyl], [2,6-bis(pyrrolidin-1-yl)-5-acetyl-4-pyrimidinyl], [2,6-bis(pyrrolidin-1-yl)-5-benzoyl-4-pyrimidinyl], [4,6-bis(2-allylamino)-1,3,5-triazin-2-yl], [4,6-bis(2-propylamino)-1,3,5-triazin-2-yl], [4,6-bis(diethylamino)-1,3,5-triazin-2-yl], [4,6-bis(pyrrolidin-1-yl)-1,3,5-triazin-2-yl], [3,6-bis(diethylamino)-pyridin-2-yl], [3,6-bis(pyrrolidin-1-yl)-pyridin-2-yl], [3,6-bis(allylamino)-pyridin-2-yl], [3,6-bis(propargylamino)-pyridin-2-yl], [3,6-bis(N-ethyl-N-allylamino)-pyr idin-2-yl].
Examples of mono-C.sub.1 -C.sub.6 -alkylamino groups are methylamino, ethylamino, propylamino, isopropylamino, n-butylamino, t-butylamino.
Examples of mono C.sub.3 -C.sub.6 -monoalkenyl- or monoalkinylamino groups are allylamino, propargylamino.
Examples of di-C.sub.1 -C.sub.6 -alkylamino groups are dimethylamino, diethylamino, methylethylamino, methylpropylamino, methylisopropylamino, diisopropylamino, methyl n-butylamino.
Examples of (C.sub.1 -C.sub.6)-alkyl-(C.sub.3 -C.sub.7)alkenylamino groups are methylallylamino, ethylallylamino, propylallylamino, isopropylallylamino.
Examples of optionally substituted benzhydryl groups are: bis (p-fluorophenyl)-methyl; bis(p-chlorophenyl)-methyl. Examples of optionally substituted phenyl groups are: p-fluorophenyl; p-chlorophenyl.
When Y is a --(CRaRb)-- group, Ra is preferably the same as Rb and they are methyl or, taken together with the carbon atom which they are linked to,. -are cyclopropyl, cyclopentyl or cyclohexyl.
When A is an ester group, it is preferably methoxycarbonyl, ethoxycarbonyl or tert-butoxycarbonyl.
When
REFERENCES:
patent: 5332735 (1994-07-01), Rault et al.
patent: 5340809 (1994-08-01), Gandry et al.
WO, A, 8 908 648 (Boehringer Biochemica Robin) 21, Sep. 1989.
Chemical Abstracts, vol. 109, No. 19, 7 Nov. 1988, Abstract No. 170371.
Chemical Abstracts, vol. 97, No. 23, 6 Dec. 1982, Abstract No. 198218.
De Cillis Gianpiero
Di Domenico Roberto
Gallico Licia
Gandolfi Carmelo A.
Long Giorgio
Boehringer Mannheim Italia S.p.A.
Grumbling Matthew V.
Shah Mukund J.
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