Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1994-12-08
1996-08-27
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
514212, 514252, 540601, C07D40304, A61K 31505
Patent
active
055502407
DESCRIPTION:
BRIEF SUMMARY
This is a natural stage application under 37 C.F.R. 371 of PCT/HU93/00034, filed Jun. 8, 1993.
FIELD OF THE INVENTION
The invention relates to novel piperazinyl-bis(alkylamino)pyrimidine derivatives of the formula ##STR1## wherein two of X, Y and Z mean a nitrogen atom each and the third one is a methine group; amino group bearing as substituent a branched-chain C.sub.4-8 alkyl, -alkenyl or -alkynyl group, or a C.sub.4-10 cycloalkyl group comprising 1 to 3 ring(s) and being optionally substituted by C.sub.1-3 alkyl group(s); or containing at most 10 carbon atoms and optionally at least one oxygen atom as an additional heteroatom; or group containing 4 to 7 carbon atoms and the other one is an above-identified primary amino group, an above-identified spiro-heterocyclic secondary amino group, or a heterocyclic secondary amino group containing 4 to 7 carbon atoms and substituted by C.sub.1-4 alkyl group(s); and
Further, the invention relates to a process for the preparation of the above compounds.
The compounds of the formula (I) according to the invention are new and possess a significant biological activity in themselves; however, their use in the preparation of lipid peroxidation-inhibiting substances bears a greater importance.
Hereinafter and in the claims primary amino groups are meant to contain a hydrogen atom as one substituent whereas the other substituent is a branched-chain C.sub.4-8 alkyl, -alkenyl or -alkynyl group, or a C.sub.4-10 cycloalkyl group, comprising 1 to 3 rings, and being optionally substituted by C.sub.1-3 alkyl group(s). The branched-chain C.sub.4-8 alkyl, -alkenyl and -alkynyl groups may be various iso-, sec- and teft-butyl, butenyl, pentyl, pentenyl, pentynyl, hexyl, hexenyl, hexynyl, pentyl, heptenyl, heptynyl, octyl, octenyl and octynyl groups. Preferred representatives of these are the 1,1-dimethylethyl, 2,2-dimethylpropyl and 4,4-dimethyl-1-penten-5-yl groups.
The C.sub.4-10 cycloalkyl group comprising 1 to 3 rings and being optionally substituted by C.sub.1-3 alkyl group(s) can be e.g. a cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or adamantyl group. These groups may be unsubstituted or bear one or more methyl, ethyl or propyl group(s) as substituents.
As R.sup.1 and R.sup.2, the spiro-heterocyclic secondary amino group containing at most 10 carbon atoms and optionally at least one additional oxygen heteroatom is exemplified by the 4,4-ethylenedioxy-1-piperidinyl group, without any limitation thereto.
When representing an unsubstituted heterocyclic secondary amino group containing 4 to 7 carbon atoms, one of R.sup.1 and R.sup.2 may preferably be a pyrrolidino, piperidino or azepino group. In this case, the other one of R.sup.1 and R.sup.2 means either a primary amino group mentioned above, or an above-defined secondary heterocyclic group having spiro structure, or an above-defined heterocyclic secondary amino group containing 4 to 7 carbon atoms and substituted by C.sub.1-4 alkyl group(s). These C.sub.1-4 alkyl groups may be the same or different, e.g. methyl, ethyl, n- or isopropyl, or n-, iso-, secor tert-butyl groups. A preferred representative of these substituted heterocyclic secondary amino groups is e.g. the 2,2,6,6-tetramethyl-1-piperidinyl group.
BACKGROUND OF THE INVENTION
Lipid peroxidation occurring as a consequence of injuries is a secondary process. Some cells are immediately destroyed when the tissues are damaged. During the next hours the injury is extended to the surrounding cells. This is induced by free oxygen radicals which attack the lipid layer of the cellular membrane and may eventually lead to cell death by damaging the membrane and releasing hydrogen peroxide. Compounds inhibiting lipid peroxidation can prevent this secondary process occurring as sequels of e.g. paralyses, cephalic or spinal traumas. Compounds possessing such an effect may be utilized e.g. for the treatment of Alzheimer's disease, muscular dystrophy and the like.
The following publications discussing the preparation of piperazinylpyrimidine derivatives are known; the prepa
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Balogh G abor
Czajlikn e Csiz er Eva
G alik Gy orgy
Lovasn e Marsai M aria
Mah o S andor
Dubno Herbert
Grumbling Matthew V.
Myers Jonathan
Richter Gedeon Vegyeszeti Gyar Rt.
Shah Mukund J.
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