Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1991-06-13
1993-12-21
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
5142392, 514317, 514319, 514450, 514452, 514466, 514481, 514486, 514510, 514524, 514539, 514597, 514620, 514630, 514651, 544 59, 544163, 544174, 546205, 546206, 546236, 546240, 548575, 548576, 549349, 549350, 549359, 549365, 549433, 549443, 558422, 560 28, 560 29, 560 42, 564 51, 564165, 564220, 564347, 564352, A61K 31135, A61K 3154, C07D27912, C07C21746
Patent
active
052721442
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to aryloxy- and heteroaryloxy-alkenylene derivatives of amines, to a process for their preparation and to pharmaceutical compositions containing them.
The invention provides compounds having the following general formula (I) ##STR3## wherein each of A and B, independently, is a group of formula (i) to (iii) ##STR4## wherein Y is --O--, --S-- or --NR-- in which R is hydrogen or C.sub.1 -C.sub.6 alkyl; different, independently is; independently, is hydrogen or C.sub.1 -C.sub.6 alkyl; or one of R.sub.7 and R.sub.8 is hydrogen or C.sub.1 -C.sub.6 alkyl and the other is a --COR.sub.9 group, wherein R.sub.9 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or --NR.sub.10 R.sub.11 in which each of R.sub.10 and R.sub.11 is independently hydrogen or C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkyl or --NR.sub.10 R.sub.11 wherein R.sub.10 and R.sub.11 are as defined above; or form a C.sub.1 -C.sub.4 alkylenedioxy group; alkynyl, C.sub.3 -C.sub.6 alkenyl; or C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by phenyl; or R.sub.1 and R.sub.2, taken together with the nitrogen atom to which they are linked, form a substituted or unsubstituted, saturated heteromonocyclic ring optionally containing a further heteroatom chosen from oxygen, sulphur and nitrogen; and the pharmaceutically acceptable salts thereof.
The invention includes within its scope all the possible isomers, stereoisomers, in particular Z and E (cis and trans) isomers and their mixtures, and the metabolites and the metabolic precursors or bio-precursors of the compounds of formula (I). In formula (I), the symbol ( ) indicates that the substituents around the carbon-carbon double bond are in the Z or E configuration or both, i.e. a mixture of Z and E isomers is present.
A halogen atom is e.g. chlorine, bromine or fluorine, preferably it is chlorine or fluorine.
The alkyl, alkenyl, alkynyl, alkylsulfonyl and alkoxy groups may be branched or straight chain groups.
A C.sub.1 -C.sub.6 alkyl group is preferably a C.sub.1 -C.sub.4 alkyl group, e.g. methyl, ethyl, propyl, isopropyl, butyl, sec.butyl or tert.butyl, more preferably it is methyl or ethyl.
A C.sub.1 -C.sub.6 alkyl group substituted by halogen may be a di- or tri-halo-substituted alkyl group in particular a trihalo-C.sub.1 -C.sub.6 alkyl group.
A trihalo-C.sub.1 -C.sub.6 alkyl group is preferably a trihalo-C.sub.1 -C.sub.4 alkyl group, e.g. trichloro-C.sub.1 -C.sub.4 alkyl or trifluoro-C.sub.1 -C.sub.4 alkyl, more preferably it is trifluoromethyl.
A C.sub.3 -C.sub.6 alkenyl group is preferably a C.sub.3 -C.sub.4 alkenyl group, in particular allyl.
A C.sub.3 -C.sub.6 alkynyl group is preferably a C.sub.3 -C.sub.4 alkynyl group, in particular propargyl.
A C.sub.1 -C.sub.6 alkoxy group is preferably a C.sub.1 -C.sub.4 alkoxy group, e.g. methoxy, ethoxy, propoxy, isopropoxy, butoxy or tert.butoxy, more preferably it is methoxy or ethoxy.
A C.sub.1 -C.sub.6 alkylthio group is preferably a C.sub.1 -C.sub.4 alkylthio group, in particular ethylthio or methylthio, more preferably methylthio.
A C.sub.1 -C.sub.4 alkylenedioxy group is in particular a C.sub.1 -C.sub.2 alkylenedioxy group, preferably methylenedioxy.
A C.sub.1 -C.sub.6 alkyl sulfonyl group is preferably a C.sub.1 -C.sub.4 alkylsulfonyl group in particular methylsulfonyl or ethylsulfonyl.
When one or both of A and B is thienyl, it is e.g. 2-or 3-thienyl, in particular 2-thienyl.
When one or both of A and B is furyl, it is e.g. 2- or 3-furyl, in particular 2-furyl.
When one or both of A and B is pyrrolyl, it is e.g. 2-or 3-pyrrolyl, in particular 2-pyrrolyl.
When one or both of A and B is naphthyl, it is e.g. 1- or 2-naphthyl.
When one or more of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is a --NR.sub.7 R.sub.8 group, as defined above under e), it is preferably:
e.sub.1) amino, C.sub.1 -C.sub.4 alkylamino or di (C.sub.1 -C.sub.4 alkyl) amino;
e.sub.2) an acetamido or propionamido group;
e.sub.3) a --NHCOOC.sub.1 -C.sub.4 alkyl group; or
e.sub.4) an ureido or a N', N'-bis di (C.sub.1 -C.sub.4 alkyl) ureido group.
W
REFERENCES:
patent: 4073917 (1978-02-01), Sandberg et al.
patent: 4229449 (1980-10-01), Melloni et al.
patent: 4271160 (1981-06-01), Melloni et al.
patent: 4699928 (1987-10-01), McDonald
Chemical Abstracts, vol. 95, No. 3, Jul. 20, 1981, Abstract No. 2477w.
Chemical Abstracts, vol. 61, No. 4, Aug. 17, 1964, Abstract No. 4250g.
J. March, "Advanced Organic Chemistry," 3rd ed. pp. 638-639, John Wiley & Sons; New York (1985).
Bonsignori Alberto
Dostert Philippe
Melloni Piero
Torre Arturo D.
Farmitalia Carlo Erba S.r.l.
Raymond Richard L.
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