Certain 1-azabicyclo[2.2.1]heptanes useful as muscarinic receptor antagonists

US5397800A · kind A · utility

Assignee

• PFIZER INC. · US

Inventors

• David Alker · Birchington, GB
• Peter E. Cross · Canterbury, GB
• John E. G. Kemp · Canterbury, GB

Key dates

• Filing date: Jun 22, 1992
• Grant date: Mar 14, 1995
• Expiry date: Jun 22, 2012

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D471/08
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

MUSCARINIC RECEPTOR ANTAGONISTS OF THE FOLLOWING FORMULAE: ##STR1## Muscarinic receptor antagonists, useful especially in the treatment of irritable bowel syndrome, of formula (IA) or (IB) or a pharmaceutically acceptable salt thereof, where R.sup.2 and R.sup.3 are each independently H, halo or C.sub.1 -C.sub.4 alkyl; m is 0, 1 or 2; n is 1, 2 or 3; Y is a direct link, O or S; with the proviso that when n is 1, Y is a direct link; Het is a group of formula (A) or (B), where p is 0, 1 or 2, q is 1, 2 or 3, and r is 0, 1, 2 or 3, with the proviso that the sum of p, q and r is at least 3, the N atom of "Het" being attached to the group (CH.sub.2).sub.n in formula (IA) and to the H atom in formula (IB); and R.sup.1 is a group of formula (a), (b) or Het.sup.1, where R.sup.4 and R.sup.5 are each independently H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --(CH.sub.2).sub.t OH, halo, trifluoromethyl, cyano, --(CH.sub.2).sub.t NR.sup.6 R.sup.7, --CO(C.sub.1 -C.sub.4 alkyl), --OCO(C.sub.1 -C.sub.4 alkyl), CH(OH)(C.sub.1 -C.sub.4 alkyl), --C(OH)(C.sub.1 -C.sub.4 alkyl).sub.2, --SO.sub.2 NH.sub.2, --(CH.sub.2).sub.t CONR.sup.6 R.sup.7 or --(CH.sub.2).sub.t COO(C.sub.1 -C.sub.4 alkyl); R…