Antipsychotic chroman derivatives of benzodioxanmethylamine

• US 5,245,051 A
• Filed: 09/03/1992
• Issued: 09/14/1993
• Est. Priority Date: 09/03/1992
• Status: Expired due to Term

• Current Assignee: Wyeth (Pfizer Inc.)
• Original Assignee: American Home Products Corporation (Pfizer Inc.)
• Inventors: Kang, Young H., Stack, Gary P.
• Primary Examiner(s): Cintins, Marianne M.
• Assistant Examiner(s): SCALZO, CATHERINE KILBY
• Application Number:
  US07/939,807
• Time in Patent Office: 376 Days
• Field of Search: 549/361, 549/366
• US Class Current: 549/361
• CPC Class Codes: C07D 407/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 493/04 Ortho-condensed systems

Abstract

A compound of the formula: ##STR1## wherein R¹ and R² are, independently, hydrogen, alkyl, alkoxy, aralkoxy, alkanoyloxy, hydroxy, halo, amino, mono- or dialkylamino, alkanamido or sulfonamido, or R¹ and R² together are methylenedioxy, ethylenedioxy, or propylenedioxy; R³ is hydrogen or alkyl; n is one of the integers 2,3 or 4; X is --C(═O)-- or --(CH₂)_m --, in which m is the integer 0 or 1; Y is methylene, ethylene or ethenylene, or a pharmaceutically acceptable salt thereof, are antipsychotic agents.

Claims

1. A compound of the formula:

##STR11## wherein R¹ and R² are, independently, hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, aralkoxy of 7 to 12 carbon atoms, alkanoyloxy of 2 to 6 carbon atoms, hydroxy, halo, amino, mono- or dialkylamino in which each alkyl group has 1 to 6 carbon atoms, alkanamido of 2 to 6 carbon atoms, or sulfonamido, or R¹ and R² together are methylenedioxy, ethylenedioxy, or propylenedioxy;

R³ is hydrogen or alkyl of 1 to 6 carbon atoms;

n is an integer 2,3 or 4;

X is --C(═

O)-- or --(CH₂)_m --, in which m is the integer 0 or 1;

Y is methylene, ethylene or ethylidene;

or a pharmaceutically acceptable salt thereof.

2. A compound of claim 1 in which R¹ and R² are, independently, fluoro, hydrogen, hydroxy, alkoxy of 1 to 6 carbon atoms or alkanoyloxy of 2 to 6 carbon atoms, or, taken together, R¹ and R² are methylenedioxy, ethylenedioxy or propylenedioxy, X is --C(═

O)--, Y is ethylene or ethylidene and the --(CH₂)_n --O-- link is to the 7 position of the chromenone or chromanone nucleus, or a pharmaceutically acceptable salt thereof.

3. A compound of claim 1 of the formula:

##STR12## in which R¹ and R² are, independently, fluoro, hydrogen, hydroxy, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 2 to 6 carbon atoms, or, taken together, R¹ and R² are methylenedioxy, ethylenedioxy or propylenedioxy, or a pharmaceutically acceptable salt thereof, wherein the benzodioxan methanamine moiety is in the S-configuration.

4. The compound of claim 1 which is 7-[3-[[(6,7-dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-yl)methyl]amino]propoxy]chromen-4-one, or a pharmaceutically acceptable salt thereof.

5. The compound of claim 1 which is (S)-7-[3-[[(6,7-dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-yl)methyl]amino]propoxy]chromen-4-one, or a pharmaceutically acceptable salt thereof.

6. The compound of claim 1 which is 7-[3-[[(6,7-dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-yl)methyl]amino]propoxy]-chroman-4-one, or a pharmaceutically acceptable salt thereof.

7. The compound of claim 1 which is 6-[3-[[(6,7-dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-yl)methyl]amino]propoxy]chromen-4-one, or a pharmaceutically acceptable salt thereof.

8. The compound of claim 1 which is N-[3-(chroman-6-yloxy)-propyl]-6,7-dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-methanamine, or a pharmaceutically acceptable salt thereof.

9. The compound of claim 1 which is N-[3-(chroman-7-yloxy)-propyl]-6,7-dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-methanamine, or a pharmaceutically acceptable salt thereof.

10. The compound of claim 1 which is 7-[3-[(7-methoxy-2,3-dihydrobenzo1,4]dioxin-2-ylmethyl)amino]propoxy]chromen-4-one, or a pharmaceutically acceptable salt thereof.

11. The compound of claim 1 which is 7-[3-[(7-hydroxy-2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amino]propoxy]chromen-4-one, or a pharmaceutically acceptable salt thereof.

12. The compound of claim 1 which is 6-[3-[(6,7-dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-ylmethyl)amino]propoxy)-benzofuran-3-one, or a pharmaceutically acceptable salt thereof.