Piperidines

• US 3,879,401 A
• Filed: 08/20/1973
• Issued: 04/22/1975
• Est. Priority Date: 09/01/1972
• Status: Expired due to Term

• Current Assignee: John Lambert Jackson, John Leheup Archibald
• Original Assignee: John Lambert Jackson, John Leheup Archibald
• Inventors: Archibald, John Leheup, Jackson, John Lambert
• Primary Examiner(s): Todd, G. Thomas
• Application Number:
  US05/390,150
• Time in Patent Office: 610 Days
• Field of Search: 260/293.64,293.71,293.77,293.76
• US Class Current: 546/190
• CPC Class Codes: C07D 211/58 attached in position 4

Abstract

This invention relates to novel heterocyclic compounds having the formula:

WHEREIN Ar represents a phenylene radical; A is selected from the group consisting of lower alkylene, mono-keto lower alkylene and hydroxy lower alkylene radicals, in all of which the lower alkylene portion contains from 1 to 6 carbon atoms; R is selected from the group consisting of cyclohexyl and substituted or unsubstituted phenyl radicals; and R1 and R2 are the same, or different, and are selected from the group consisting of hydrogen and alkyl radicals of 1 to 6 carbon atoms which may be straight chain or branched; or R1 and R2 together with the nitrogen atom to which they are attached represent a heterocyclic ring of 4 to 6 carbon atoms; and the acid addition and quaternary ammonium salts thereof; which exhibit action on the cardiovascular system, in particular Alpha -adrenoceptor antagonism. The invention also concerns pharmaceutical compositions containing the heterocyclic compounds of formula I.

Claims

1. A compound selected from the group consisting of bases of the formula:

2. A compound as claimed in claim 1 which is 4-benzamido-1-(4-(4-(2-hydroxy-3-(N-isopropylamino)propoxy)phenyl-4 -oxobutyl)piperidine.

3. A compound as claimed in claim 1 which is 4-benzamido-1-(4-(4-(2-hydroxy-3-(N-t-butylamino)propoxy))phenyl-4 -oxobutyl)piperidine.

4. A compound as claimed in claim 1 which is 4-(p-chlorobenzamido)-1-(4-(4-(2-hydroxy-3-(N-isopropylamino) propoxy))phenyl-4-oxobutyl)piperidine.

5. A compound as claimed in claim 1 which is 4-(m-methoxybenzamido)-1-(4-(4-(2-hydroxy-3-(N-isopropylamino) propoxy))-phenyl-4-oxobutyl)piperidine.

6. A compound as claimed in claim 1 which is 4-cyclohexanecarboxamido-1-(4-(4-(2-hydroxy-3-(N-isopropylamino) propoxy))-phenyl-4-oxobutyl)piperidine.

7. A compound as claimed in claim 1 which is 4-benzamido-1-(4-(4-(2-hydroxy-3-(N-methyl-N-isopropylamino)propoxy))phenyl -4-oxobutyl)piperidine.

8. A compound as claimed in claim 1 which is 4-benzamido-1-(4-(4-(2-hydroxy-3-piperidinopropoxy))phenyl-4-oxobutyl) -piperidine.

9. A compound as claimed in claim 1 which is 4-benzamido-1-(4-(4-(2-hydroxy-3-(pyrrolidin-1-yl)propoxy))phenyl-4 -oxobutyl)piperidine.

10. A compound as claimed in claim 1 which is 4-benzamido-1-(4-(4-(2-hydroxy-3-(N-isopropylamino)propoxy))phenyl-4 -hydroxybutyl)piperidine.