Claims
- 1. A chemical compound having the formula ##STR30## a pharmaceutically acceptable acid addition salt form thereof or a stereochemically isomeric form thereof, wherein
- R is hydrogen or C.sub.1-6 alkyl;
- R.sup.1 and R.sup.2 each independently are hydrogen, halo, hydroxy, C.sub.1-6 alkyloxy or C.sub.1-6 alkyl;
- X is O, S or NR.sup.3 ; said R.sup.3 being hydrogen, C.sub.1-6 alkyl, aryl or arylC.sub.1-6 alkyl;
- Alk is C.sub.1-4 alkanediyl; and
- Q is a radical of formula ##STR31## wherein Y.sup.1 and Y.sup.2 each independently are O or S;
- R.sup.4 is hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, trifluoromethyl, nitro, cyano, hydroxy, (C.sub.1-10 alkylcarbonyl)oxy, amino, mono- and di(C.sub.1-6 alkyl)amino, (C.sub.1-10 alkylcarbonyl)amino, phenylmethoxy or azido;
- R.sup.5 is hydrogen or halo; or
- Q is a radical of formula ##STR32## wherein R.sup.6 is hydrogen or C.sub.1-6 alkyl;
- Z is --S-- or --CR.sup.7 .dbd.CR.sup.8 --; said R.sup.7 and R.sup.8 each independently being hydrogen or C.sub.1-6 alkyl; or Z is --CH.sub.2 -- wherein one hydrogen atom may be replaced by hydroxy or C.sub.1-6 alkyl;
- A is a bivalent radical --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 -- wherein in the latter two radicals one or two hydrogen atoms may be replaced by C.sub.1-6 alkyl; or A is a bivalent radical --CR.sup.9 .dbd.CR.sup.10, wherein R.sup.9 and R.sup.10 each independently are hydrogen, halo, amino or C.sub.1-6 alkyl; or when Z is --S--, then A may also be --CR.sup.11 .dbd.N--, R.sup.11 being hydrogen or C.sub.1-6 alkyl; or when Z is --CR.sup.7 .dbd.CR.sup.8 --, then A also may be --O--; and
- each aryl is phenyl optionally substituted with up to three substituents independently selected from C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, hydroxy, halo, amino, nitro and trifluoromethyl.
- 2. A chemical compound according to claim 1 wherein R is hydrogen; R.sup.1 and R.sup.2 each independently are hydrogen, halo or C.sub.1-6 alkyl; Q is a radical of formula (a) wherein Y.sup.1 and Y.sup.2 are oxygen, and R.sup.4 and R.sup.5 are hydrogen, or Q is a radical of formula (b) wherein R.sup.6 is C.sub.1-6 alkyl.
- 3. A chemical compound according to claim 2 wherein R.sup.2 is hydrogen or halo; X is O, S or NH; Q is a radical of formula (b), Z is --S-- or --CR.sup.7 .dbd.CH--, said R.sup.7 being hydrogen or C.sub.1-6 alkyl, or Z is CH.sub.2 wherein one hydrogen atom may be replaced by C.sub.1-6 alkyl; and A is --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 --, wherein in each of the latter two radicals one or two hydrogen atoms may be replaced by C.sub.1-6 alkyl, or A is --CR.sup.9 .dbd.CR.sup.10 --, said R.sup.9 and R.sup.10 each independently being hydrogen or C.sub.1-6 alkyl.
- 4. A chemical compound according to claim 3 wherein R.sup.1 is hydrogen, fluoro or methyl; R.sup.2 is hydrogen; --Z--A-- is --S--CH.sub.2 --CH.sub.2 --, --S--CH.sub.2 --CH.sub.2 --CH.sub.2 --, --S--CH.dbd.CR.sup.10 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --, --CH(CH.sub.3)--CH.sub.2 --CH.sub.2 --CH.sub.2 --, --C(CH.sub.3).dbd.CH--CH.dbd.CH-- or --CH.dbd.CH--CH.dbd.CR.sup.10 --, R.sup.10 being hydrogen or methyl.
- 5. A chemical compound according to claim 4 wherein X is O or NH; and R.sup.1 is hydrogen or 6-fluoro.
- 6. An antipsychotic composition comprising an inert carrier and as active ingredient an antipsychotic effective amount of a chemical compound as claimed in claim 1.
- 7. An antipsychotic composition according to claim 6 wherein R is hydrogen; R.sup.1 and R.sup.2 each independently are hydrogen, halo or C.sub.1-6 alkyl; Q is a radical of formula (a) wherein Y.sup.1 and Y.sup.2 are oxygen, and R.sup.4 and R.sup.5 are hydrogen, or Q is a radical of formula (b) wherein R.sup.6 is C.sub.1-6 alkyl.
- 8. An antipsychotic composition according to claim 7 wherein R.sup.2 is hydrogen or halo; X is O, S or NH; Q is a radical of formula (b), Z is --S-- or --CR.sup.7 .dbd.CH--, said R.sup.7 being hydrogen or C.sub.1-6 alkyl, or Z is CH.sub.2 wherein one hydrogen atom may be replaced by C.sub.1-6 alkyl; and A is --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 --, wherein in each of the latter two radicals one or two hydrogen atoms may be replaced by C.sub.1-6 alkyl, or A is --CR.sup.9 .dbd.CR.sup.10 --, said R.sup.9 and R.sup.10 each independently being hydrogen or C.sub.1-6 alkyl.
- 9. An antipsychotic composition according to claim 8 wherein R.sup.1 is hydrogen, fluoro or methyl; R.sup.2 is hydrogen; --Z--A-- is --S--CH.sub.2 --CH.sub.2 --, --S--CH.sub.2 --CH.sub.2 --CH.sub.2 --, --S--CH.dbd.CR.sup.10 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --, --CH(CH.sub.3)--CH.sub.2 --CH.sub.2 --CH.sub.2 --, --C(CH.sub.3).dbd.CH--CH.dbd.CH-- or --CH.dbd.CH--CH.dbd.CR.sup.10 --, R.sup.10 being hydrogen or methyl.
- 10. An antipsychotic composition according to claim 9 wherein X is O or NH; and R.sup.1 is hydrogen or 6-fluoro.
- 11. A method of treating warm-blooded animals suffering from psychotic diseases comprising the administration to said warm-blooded animals of an antipsychotically effective amount of a chemical compound as claimed in claim 1.
- 12. A method according to claim 11 wherein R is hydrogen; R.sup.1 and R.sup.2 each independently are hydrogen, halo or C.sub.1-6 alkyl; Q is a radical of formula (a) wherein Y.sup.1 and Y.sup.2 are oxygen, and R.sup.4 and R.sup.5 are hydrogen, or Q is a radical of formula (b) wherein R.sup.6 is C.sub.1-6 alkyl.
- 13. A method according to claim 12 wherein R.sup.2 is hydrogen or halo; X is O, S or NH; Q is a radical of formula (b), Z is --S-- or --CR.sup.7 .dbd.CH--, said R.sup.7 being hydrogen or C.sub.1-6 alkyl, or Z is CH.sub.2 wherein one hydrogen atom may be replaced by C.sub.1-6 alkyl; and A is --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 --, wherein in each of the latter two radicals one or two hydrogen atoms may be replaced by C.sub.1-6 alkyl, or A is --CR.sup.9 .dbd.CR.sup.10 --, said R.sup.9 and R.sup.10 each independently being hydrogen or C.sub.1-6 alkyl.
- 14. A method according to claim 13 wherein R.sup.1 is hydrogen, fluoro or methyl; R.sup.2 is hydrogen; --Z--A-- is --S--CH.sub.2 --CH.sub.2 --, --S--CH.sub.2 --CH.sub.2 --CH.sub.2 --, --S--CH.dbd.CR.sup.10 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --, --CH(CH.sub.3)--CH.sub.2 --CH.sub.2 --CH.sub.2 --, --C(CH.sub.3).dbd.CH--CH.dbd.CH-- or --CH.dbd.CH--CH.dbd.CR.sup.10 --, R.sup.10 being hydrogen or methyl.
- 15. A method according to claim 14 wherein X is O or NH; and R.sup.1 is hydrogen or 6-fluoro.
CROSS-REFERENCE TO RELATED APPLICATION
This is a continuation-in-part of our co-pending application Ser. No. 228,417, filed Aug. 5, 1988, now abandoned.
US Referenced Citations (8)
Foreign Referenced Citations (4)
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0135781 |
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EPX |
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Non-Patent Literature Citations (4)
Entry |
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Kennis et al., Chem. Abst., 106-67292x, (1987). |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
228417 |
Aug 1988 |
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