Claims for Patent: 7,262,298

Summary for Patent: 7,262,298

Title:	4-hydroxybenzomorphans
Abstract:	4-Hydroxybenzomorphans containing carboxamide or thiocarboxamide at the 3-position are useful as analgesics, anti-diarrheal agents, anticonvulsants, antitussives and anti-addiction medications.
Inventor(s):	Mark P. Wentland
Assignee:	Rensselaer Polytechnic Institute
Application Number:	US11/266,651
Patent Claims:	1. A compound of formula: wherein A is chosen from —C(═O)NH2 and —C(═S)NH2; R2 and R2a are both hydrogen or taken together R2 and R2a are ═O; R3 is chosen from hydrogen, lower alkyl, alkenyl, aryl, heterocyclyl, benzyl and hydroxyalkyl; R4 is chosen from hydrogen, hydroxy, amino, lower alkoxy, C1–C20 alkyl and C1–C20 alkyl substituted with hydroxy or carbonyl; R11 is hydrogen; R12 is chosen from hydrogen, hydroxy, lower alkoxy and —NR13R14; or together, R11 and R12 form a carbonyl or a vinyl substituent; R13 and R14 are chosen independently from hydrogen and C1 to C7 hydrocarbon; and the dotted line represents an optional double bond. 2. A compound according claim 1 wherein R2 and R2a are hydrogen; R3 is chosen from hydrogen, cyclopropyl, and cyclobutyl, vinyl and tetrahydrofuranyl; R4 is chosen from hydrogen and hydroxyl; R11 is hydrogen; R12 is chosen from hydrogen and hydroxy; or together, R11 and R12 form a carbonyl. 3. A compound according to claim 1 of formula: wherein R2 and R2a are both hydrogen or taken together R2 and R2a are ═O; R3 is chosen from hydrogen, lower alkyl, alkenyl, aryl, heterocyclyl, benzyl and hydroxyalkyl; R4 is chosen from hydrogen, hydroxy, amino, lower alkoxy, C1–C20 alkyl and C1–C20 alkyl substituted with hydroxy or carbonyl; R11 is hydrogen; R12 is chosen from hydrogen, hydroxy, lower alkoxy and —NR13R14; or together, R11 and R12 form a carbonyl or a vinyl substituent; R13 and R14 are chosen independently from hydrogen and C1 to C7 hydrocarbon; and the dotted line represents an optional double bond. 4. A compound according to claim 3 wherein: R2 and R2a are hydrogen; R3 is chosen from hydrogen, cyclopropyl, and cyclobutyl, vinyl and tetrahydrofuranyl; R4 is chosen from hydrogen and hydroxyl; R11 is hydrogen; R12 is chosen from hydrogen and hydroxy; or together, R11 and R12 form a carbonyl. 5. A compound according to claim 4 selected from the group of 6. A compound according to claim 1 of formula: wherein R2 and R2a are both hydrogen or taken together R2 and R2a are ═O; R3 is chosen from hydrogen, lower alkyl, alkenyl, aryl, heterocyclyl, benzyl and hydroxyalkyl; R4 is chosen from hydrogen, hydroxy, amino, lower alkoxy, C1–C20 alkyl and C1–C20 alkyl substituted with hydroxy or carbonyl; R11 is hydrogen; R12 is chosen from hydrogen, hydroxy, lower alkoxy and —NR13R14; or together, R11 and R12 form a carbonyl or a vinyl substituent; R13 and R14 are chosen independently from hydrogen and C1 to C7 hydrocarbon; and the dotted line represents an optional double bond. 7. A compound according to claim 6 wherein: R2 and R2a are hydrogen; R3 is chosen from hydrogen, cyclopropyl, and cyclobutyl, vinyl and tetrahydrofuranyl; R4 is chosen from hydrogen and hydroxyl; R11 is hydrogen; R12 is chosen from hydrogen and hydroxy; or together, R11 and R12 form a carbonyl. 8. The compound of formula according to claim 5.