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Last Updated: May 8, 2024

Claims for Patent: 7,262,298

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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):	Wentland; Mark P. (Menands, NY)
Assignee:	Rensselaer Polytechnic Institute (Troy, NY)
Application Number:	11/266,651
Patent Claims:	1. A compound of formula: ##STR00024## wherein A is chosen from --C(.dbd.O)NH.sub.2 and --C(.dbd.S)NH.sub.2; R.sup.2 and R.sup.2a are both hydrogen or taken together R.sup.2 and R.sup.2a are .dbd.O; R.sup.3 is chosen from hydrogen, lower alkyl, alkenyl, aryl, heterocyclyl, benzyl and hydroxyalkyl; R.sup.4 is chosen from hydrogen, hydroxy, amino, lower alkoxy, C.sub.1 C.sub.20 alkyl and C.sub.1 C.sub.20 alkyl substituted with hydroxy or carbonyl; R.sup.11 is hydrogen; R.sup.12 is chosen from hydrogen, hydroxy, lower alkoxy and --NR.sup.13R.sup.14; or together, R.sup.11 and R.sup.12 form a carbonyl or a vinyl substituent; R.sup.13 and R.sup.14 are chosen independently from hydrogen and C.sub.1 to C.sub.7 hydrocarbon; and the dotted line represents an optional double bond. 2. A compound according claim 1 wherein R.sup.2 and R.sup.2a are hydrogen; R.sup.3 is chosen from hydrogen, cyclopropyl, and cyclobutyl, vinyl and tetrahydrofuranyl; R.sup.4 is chosen from hydrogen and hydroxyl; R.sup.11 is hydrogen; R.sup.12 is chosen from hydrogen and hydroxy; or together, R.sup.11 and R.sup.12 form a carbonyl. 3. A compound according to claim 1 of formula: ##STR00025## wherein R.sup.2 and R.sup.2a are both hydrogen or taken together R.sup.2 and R.sup.2a are .dbd.O; R.sup.3 is chosen from hydrogen, lower alkyl, alkenyl, aryl, heterocyclyl, benzyl and hydroxyalkyl; R.sup.4 is chosen from hydrogen, hydroxy, amino, lower alkoxy, C.sub.1 C.sub.20 alkyl and C.sub.1 C.sub.20 alkyl substituted with hydroxy or carbonyl; R.sup.11 is hydrogen; R.sup.12 is chosen from hydrogen, hydroxy, lower alkoxy and --NR.sup.13R.sup.14; or together, R.sup.11 and R.sup.12 form a carbonyl or a vinyl substituent; R.sup.13 and R.sup.14 are chosen independently from hydrogen and C.sub.1 to C.sub.7 hydrocarbon; and the dotted line represents an optional double bond. 4. A compound according to claim 3 wherein: R.sup.2 and R.sup.2a are hydrogen; R.sup.3 is chosen from hydrogen, cyclopropyl, and cyclobutyl, vinyl and tetrahydrofuranyl; R.sup.4 is chosen from hydrogen and hydroxyl; R.sup.11 is hydrogen; R.sup.12 is chosen from hydrogen and hydroxy; or together, R.sup.11 and R.sup.12 form a carbonyl. 5. A compound according to claim 4 selected from the group of ##STR00026## 6. A compound according to claim 1 of formula: ##STR00027## wherein R.sup.2 and R.sup.2a are both hydrogen or taken together R.sup.2 and R.sup.2a are .dbd.O; R.sup.3 is chosen from hydrogen, lower alkyl, alkenyl, aryl, heterocyclyl, benzyl and hydroxyalkyl; R.sup.4 is chosen from hydrogen, hydroxy, amino, lower alkoxy, C.sub.1 C.sub.20 alkyl and C.sub.1 C.sub.20 alkyl substituted with hydroxy or carbonyl; R.sup.11 is hydrogen; R.sup.12 is chosen from hydrogen, hydroxy, lower alkoxy and --NR.sup.13R.sup.14; or together, R.sup.11 and R.sup.12 form a carbonyl or a vinyl substituent; R.sup.13 and R.sup.14 are chosen independently from hydrogen and C.sub.1 to C.sub.7 hydrocarbon; and the dotted line represents an optional double bond. 7. A compound according to claim 6 wherein: R.sup.2 and R.sup.2a are hydrogen; R.sup.3 is chosen from hydrogen, cyclopropyl, and cyclobutyl, vinyl and tetrahydrofuranyl; R.sup.4 is chosen from hydrogen and hydroxyl; R.sup.11 is hydrogen; R.sup.12 is chosen from hydrogen and hydroxy; or together, R.sup.11 and R.sup.12 form a carbonyl. 8. The compound of formula ##STR00028## according to claim 5.

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