# US 5,346,910 A · Maleimide derivatives of oxotremorine

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,346,910 A
- Document ID: US5346910A
- Status: Granted
- Kind: A
- Application number: 07/893,146
- Filed: 1992-06-03
- Granted: 1994-09-13
- Earliest claimed: 1992-06-03
- Assignees: American Cyanamid Company
- Inventors: Eugene J. Trybulski; Herbert J. Brabander
- Web page: https://patentgrep.com/patent/US5346910A

## CPC

- C07D 207/416: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Maleimide derivatives of oxotremorine and their alkylthiol addition products having the general formulae: ##STR1## wherein R.sub.1 and R.sub.2 are independently alkyl, hydroxyalkyl, acyloxy, trialkylsilyloxy or R.sub.1 and R.sub.2 taken together are substituted or unsubstituted pyrrolidine or piperidine, and pharmaceutical compositions for the treatment of central cholinergic disfunction.

## Claims

### Claim 1

A compound selected from those of the formulae II and IV: ##STR8## wherein R.sub.1 and R.sub.2 are independently selected from straight and branched (C.sub.1 -C.sub.6)alkyl; or R.sub.1 is selected from straight and branched (C.sub.1 -C.sub.6)alkyl and R.sub.2 is --(CH.sub.2).sub.n R.sub.9 where n=2-6 and R.sub.9 is selected from hydroxy, (C.sub.1 -C.sub.10)acyloxy, and trialkylsilyloxy or R.sub.1 and R.sub.2 taken together with their associated N(itrogen) are selected from the group consisting of pyrrolidine, piperidine and moieties of the formula: ##STR9## wherein R.sub.5 and R.sub.6 are independently selected from (C.sub.1 -C.sub.10)acyloxy, (C.sub.1 -C.sub.6)alkoxy, aroyloxy, substituted aroyloxy (wherein the substituting moiety is selected from hydroxy, halo, alkyl (C.sub.1 -C.sub.6) and alkoxy (C.sub.1 -C.sub.6), hydroxy, thio, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1 -C.sub.6)alkyldithio, (C.sub.1 -C.sub.10)acylthio and hydrogen; and R.sub.7 and R.sub.8 are selected from hydrogen, substituted methyl wherein the substituting moiety is selected from hydroxy, halo, (C.sub.1 -C.sub.6) alkylsulfonyloxy and phenylsulfonyloxy with the proviso that only one R.sub.5, R.sub.6, R.sub.7, or R.sub.8 can be a substituent other than hydrogen;
R.sub.3 is selected from hydrogen, straight and branched (C.sub.1 -C.sub.6)alkyl;
R.sub.4 is selected from, straight and branched (C.sub.1 -C.sub.6) alkylthio;
R.sub.10 is selected from (C.sub.1 -C.sub.6)alkyl; and the pharmacologically acceptable salts thereof.

### Claim 2 (depends on 1)

A compound according to claim 1, 1-[4-(dimethylamino)-2-butynyl]-3-(methylthio)-2,5-pyrrolidinedione.

### Claim 3 (depends on 1, 3)

A compound according to claim 1, 3-(methylthio)-1-[4(1-pyrrolidinyl)-2-butynyl]-2,5-pyrrolidinedione.

### Claim 4 (depends on 1)

A compound according to claim 1, N,N,N-trimethyl-4-[3-(methylthio)-2,5-dioxo-1-pyrrolidinyl]-2-butyn-1-amin ium iodide.