TREA

1H-2-Benzopyran-1-yl alkyl on 1-(isochroman-1-yl)alkyl piperazines

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Information

  • Patent Grant
  • 4577021
  • Patent Number
    4,577,021
  • Date Filed
    Monday, April 1, 1985
    40 years ago
  • Date Issued
    Tuesday, March 18, 1986
    39 years ago
Information
Abstract
1H-2-benzopyran-1-yl alkyl or 1-(isochroman-1-yl) alkyl 4-phenyl piperazines are prepared and exhibit antipsychotic and hypotensive activity.
Description
Claims
  • 1. A compound selected from the group consisting of
  • 4-(2-methylphenyl)-1-[3-(3,4-dihydro-6,7-dimethoxy-1,4-dimethyl-1H-2-benzopyran-1-yl)-propyl]piperazine;
  • 4-(2-methylphenyl)-1-[3-(3,4-dihydro-6,7-dimethoxy-1,4-dimethyl-1H-2-benzopyran-1-yl)-propyl]piperazine, monohydrochloride;
  • 1-[2-(3,4-dihydro-6,7-dimethoxy-4,4-dimethyl-1H-2-benzopyran-1-yl)ethyl]-4-(2-methylphenyl)piperazine;
  • 1-[2-(3,4-dihydro-6,7-dimethoxy-4,4-dimethyl-1H-2-benzopyran-1-yl)ethyl]-4-(2-methylphenyl)piperazine, monohydrochloride;
  • 1-[2-(6,7-dimethoxy-4,4-dimethylisochroman-1-yl)ethyl]-4-(3-trifluoromethylphenyl)piperazine;
  • 1-[2-(6,7-dimethoxy-4,4-dimethylisochroman-1-yl)ethyl]-4-(3-trifluoromethylphenyl)piperazine, dihydrochloride;
  • 4-(2-methylphenyl)-1-[3-(3,4-dihydro-6,7-dimethoxy-1,4,4-trimethyl-1H-2-benzopyran-1-yl)-propyl]piperazine;
  • 4-(2-methylphenyl)-1-[3-(3,4-dihydro-6,7-dimethoxy-1,4,4-trimethyl-1H-2-benzopyran-1-yl)-propyl]piperazine, dihydrochloride;
  • 4-(2-methylphenyl)-1-[3-(3,4-dihydro-1-(4-fluorophenyl)-6,7-dimethoxy-1H-2-benzopyran-1-yl)propyl]piperazine;
  • 4-(2-methylphenyl)-1-[3-(3,4-dihydro-1-(4-fluorophenyl)-6,7-dimethoxy-1H-2-benzopyran-1-yl)propyl]piperazine, hydro-chloride hydrate;
  • 4-(2-methylphenyl)-1-[2-(3,4-dihydro-6,7-dimethoxy-3,3-dimethyl-1H-2-benzopyran-1-yl)-ethyl]piperazine;
  • 4-(2-methylphenyl)-1-[2-(3,4-dihydro-6,7-dimethoxy-3,3-dimethyl-1H-2-benzopyran-1-yl)-ethyl]piperazine, monohydrochloride; and
  • 1-[3-(3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran-1-yl)propyl]-4-(2-methylphenyl)piperazine.
  • 2. A compound of claim 1 for 4-(2-methylphenyl)-1-[3-(3,4-dihydro-6,7-dimethoxy-1,4-dimethyl-1H-2-benzopyran-1-yl)-propyl]piperazine.
  • 3. The monohydrochloride of the compound of claim 2.
  • 4. A compound according to claim 1 for 1-[2-(3,4-dihydro-6,7-dimethoxy-4,4-dimethyl-1H-2-benzopyran-1-yl)ethyl]-4-(2-methylphenyl)-piperazine.
  • 5. The monohydrochloride of the compound of claim 4.
  • 6. A compound according to claim 1 for 1-[2-(6,7-dimethoxy-4,4-dimethylisochroman-1-yl)ethyl]-4-(3-trifluoromethylphenyl)piperazine.
  • 7. The dihydrochloride salt of the compound of claim 6.
  • 8. A compound of claim 1 for 4-(2-methyl-phenyl)-1-[3-(3,4-dihydro-6,7-dimethoxy-1,4,4-trimethyl-1H-2-benzopyran-1-yl)-propyl]piperazine.
  • 9. The dihydrochloride salt of the compound of claim 8.
  • 10. A compound of claim 1 for 4-(2-methylphenyl)-1-[3-(3,4-dihydro-1-(4-fluorophenyl)-6,7-dimethoxy-1H-2-benzopyran-1-yl)propyl]piperazine.
  • 11. The hydrochloride hydrate of the compound of claim 10.
  • 12. A compound of claim 1 for 4-(2-methylphenyl)-1-[2-(3,4-dihydro-6,7-dimethyoxy-3,3-dimethyl-1H-2-benzopyran-1-yl)-ethyl]piperazine.
  • 13. The monohydrochloride of the compound of claim 12.
  • 14. A compound of claim 1 for 1-[3-(3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran-1-yl]-4-(2-methylphenyl)piperazine.
DESCRIPTION

This application is a continuation of Ser. No. 026,719 filed Apr. 4, 1979, now abandoned, which is a continuation-in-part of application Ser. No. 847,350 filed Oct. 31, 1977, now abandoned.

US Referenced Citations (3)
Number Name Date Kind
3467675 Petersen et al. Sep 1969
4066648 Oka et al. Jan 1978
4487774 McCall Dec 1984
Continuations (1)
Number Date Country
Parent 26719 Apr 1979
Continuation in Parts (1)
Number Date Country
Parent 847350 Oct 1977