Neurotransmitter releasers useful for cognition enhancement

US5414004A · kind A · utility

Assignee

• The DuPont Merck Pharmaceutical Company · US

Inventors

• Wendell W. Wilkerson · New Castle, US
• Richard A. Earl · Wilmington, US
• Matthew E. Voss · Singapore, SG

Key dates

• Filing date: Sep 20, 1993
• Grant date: May 9, 1995
• Expiry date: Sep 20, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D405/06
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Compounds of the following formula have been shown to enhance the release of the neurotransmitter acetylcholine, and thus may be useful in the treatment of diseases of man involving learning and cognition, where subnormal levels of this neurochemical are found ##STR1## wherein R.sup.1 is 4-,3-, or 2-pyridyl, 2-fluoro-4-pyridyl or 3-fluoro-4-pyridyl; PA1 R.sup.2 is alkyl of 1 to 10 carbons, cycloalkyl of 3 to 8 carbons, 2-,3-, or 4-pyridyl, Phe or Phe-W; PA1 Phe is a phenyl group; PA1 W is F, Cl, Br, R.sup.4, --OH, --OR.sup.4, --NO.sub.2, --NH.sub.2, --NHR.sup.4, --NR4R.sup.4, --CN, --S(O)m --R.sup.4 ; PA1 R.sup.3 is H, F, Cl, Br, --CN, --OH, --NO.sub.2, --NH.sub.2, --CF.sub.3, --NHR.sup.4, --NR.sup.4 R.sup.4, R.sup.4, --OR.sup.4, --S(O).sub.m --R.sup.4 PA1 R.sup.4 is alkyl of 1 to 4 carbons, CH.sub.2 Phe-- or Phe--; PA1 R.sup.5 is --(CH.sub.2).sub.n --Y or --OCOR.sup.4 ; PA1 Y is NH.sub.2, --NHR.sup.4, --NR.sup.4 R.sup.4, --NHCOR.sup.4, --NHCO.sub.2 R.sup.4, F, Cl, Br, OR.sup.4, --S(O).sub.m R.sup.4, --CO.sub.2 H, --CO.sub.2 R.sup.4, --CN, --CONR.sup.4 R.sup.4, --CON HR.sup.4, CONHR.sup.4, --CONH.sub.2, --COR.sup.4 ; --CH.dbd.CHCO.sub.2 R.sup.4, OCOR.sup.4, CO.tbd.CCO.sub.2 R.sup.4…