Disubstituted polycyclic systems and preparative methods therefor

US5424430A · kind A · utility

Assignee

• The DuPont Merck Pharmaceutical Company · US

Inventors

• James H. Jensen · Wilmington, US
• Timothy D. Costello · Wilmington, US
• Leon De Brabander, Jr. · Wilmington, US
• Matthew E. Voss · Singapore, SG

Key dates

• Filing date: Sep 10, 1993
• Grant date: Jun 13, 1995
• Expiry date: Sep 10, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D213/57
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Polycyclic cognition enhancers having the general formula (1a), (1b) or (1c) are provided: ##STR1## wherein: R.sub.1 is a heterocyclic aromatic moiety such as a 4-pyridyl, 2-pyridyl, 4-pyrimidyl, or pyrazinyl group; PA1 R.sub.2 and R.sub.3 are independently H, F, Cl, Br, NO.sub.2, CONH.sub.2, CON(R.sub.4)(R.sub.4 '), S(O).sub.m R.sub.4, CF.sub.3, or N(R.sub.4)(R.sub.4 '); PA1 R.sub.4 and R.sub.4 ' are independently H, alkyl having from 1 to 4 carbon atoms, CH.sub.2 Phe--W, or Phe--W; PA1 Phe is a phenyl group; PA1 R.sub.5 is --(CH.sub.2).sub.n --Y or --OCOR.sub.4 ; PA1 Y is H, OH, NH.sub.2, NHR.sub.4, N(R.sub.4)(R.sub.4 '), NHCOR.sub.4, NHCO.sub.2 R.sub.4, NHS(O).sub.2 R.sub.4, F, Cl, Br, OR.sub.4, S(O).sub.m R.sub.4, CO.sub.2 H, CO.sub.2 R.sub.4, CN, CON(R.sub.4)(R.sub.4 '), CONHR.sub.4, CONH.sub.2, COR.sub.4, Phe, Phe--W, --C.tbd.CCO.sub.2 R.sub.4, --CH.dbd.CHR.sub.4, --C.tbd.CR.sub.4, or a heterocyclic aromatic moiety such as a 4-pyridyl, 2-pyridyl, 4-pyrimidyl, or pyrazinyl group; PA1 W is F, Cl, Br, R.sub.4, OR.sub.4, NO.sub.2, NH.sub.2, NHR.sub.4, N(R.sub.4)(R.sub.4 '), CN, or S(O).sub.m R.sub.4 ; PA1 m is 1 or 2; and PA1 n is 1-7. Also provided are preparative processes for …