Fused heteroalkylene quinolinamines

• US 5,208,330 A
• Filed: 02/25/1992
• Issued: 05/04/1993
• Est. Priority Date: 04/23/1987
• Status: Expired due to Term

• Current Assignee: Hoechst-Roussel Pharmaceuticals Incorporated (Sanofi )
• Original Assignee: Hoechst-Roussel Pharmaceuticals Incorporated (Sanofi )
• Inventors: Shutske, Gregory M., Effland, Richard C.
• Primary Examiner(s): RICHTER, JOHANN R
• Application Number:
  US07/841,168
• Time in Patent Office: 434 Days
• Field of Search: 540/471, 540/590, 540/591, 540/592, 546/81, 546/84, 546/89, 546/92, 546/93, 546/79
• US Class Current: 540/471
• CPC Class Codes: C07D 491/04 Ortho-condensed systems
• CPC Class Codes: C07D 495/04 Ortho-condensed systems

Abstract

There are disclosed compounds having the formula ##STR1## wherein n is 1-4; R is hydrogen, loweralkyl or loweralkylcarbonyl; R₁ is hydrogen, loweralkyl, loweralkylcarbonyl, aryl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, oxygen-bridged arylloweralkyl, or oxygen-bridged diaryllowerallyl; A is a direct bond or (CHR₃)_m, m being 1-3; X is hydrogen, loweralkyl, cycloalkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkylcarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR₄ or --NR₅ R₆, R₄ being hydrogen or loweralkyl, and R₅ and R₆ being independently hydrogen, loweralkyl or cycloalkyl; Y is O, S or NR₇ ; and each R₂, each R₃ and R₇ are independently hydrogen or loweralkyl, or taken two at a time form a methylene or ethylene group constituting a part of a ring of at least five atoms; stereo, optical and geometrical isomers thereof, and pharmaceutically acceptable acid addition salts thereof, which are useful for enhancing memory.

Claims

1. A compound having the formula ##STR11## wherein n is 1-4;

A is a direct bond or (CHR₃)_m, m being 1-3;

X is hydrogen, loweralkyl, cycloalkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkylcarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR₄ or -NR₅ R₆, R₄ being hydrogen or loweralkyl, and R₅ and R₆ being independently hydrogen, loweralkyl or cycloalkyl;

Y is O, S or NR₇ ;

Z is halogen, hydroxy or loweralkoxy; and

R₂, R₃ and R₇ are independently hydrogen or loweralkyl, or taken two at a time form a methylene or ethylene group constituting a part of a ring of at least five atoms with the proviso that when A is CH₂, Y is NCH₃, (CHR₂)_n is CH₂ CH₂ and X is H, CH₃, Cl, Br or NO₂, Z is not Cl; and

whenever A, Y and (CH)_n forms a seven-membered ring consisting of one nitrogen atom and six carbon atoms, X is --SH, cycloalkyl, loweralkylthio, or --NHCOR₄.