8-carboxamido-2,6-methano-3-benzazocines
AssigneeRensselaer Polytechnic Institute
InventorMark P. WENTLAND
Life of this patent
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Abstract
8-Substituted-2,6-methano-3-benzazocines of general structure I in which A is —CH2—OH, —CH2NH2, —NHSO2CH3, and Y is O, S or NOH are useful as analgesics, anti-diarrheal agents, anticonvulsants, antitussives and anti-addiction medications. 8-Carboxamides, thiocarboxamides, hydroxyamidines and formamides are preferred.
Claims6
A compound of formula:
- wherein
- A is chosen from
- Q is chosen from O, S and NR17;
- Y is chosen from O, S, NR17 and NOH;
- R1 is chosen from hydrogen, lower alkoxy, phenyl and —NHR8;
- 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;
- R5 is lower alkyl;
- R6 is lower alkyl;
- R7 is chosen from hydrogen and hydroxy;
- or together R4, R5, R6 and R7 may form from one to three rings, said rings having optional additional substitution;
- R8 is chosen from hydrogen, —OH, —NH2 and —CH2R15;
- R15 is chosen from hydrogen, alkyl, aryl, substituted aryl and alkyl substituted with alkoxy, amino, alkylamino or dialkylamino;
- R16 is chosen from hydrogen and NH2;
- and
- R17 is chosen from hydrogen, alkyl, aryl and benzyl.
A method of treating a disease or condition selected from pain, pruritus, diarrhea, cough, drug addiction, hyperalgesia, respiratory depression, dyskinesia, gastrointestinal motility disorders, and irritable bowel syndrome comprising the step of administering to a subject in need thereof a compound of formula:
- wherein
- A is chosen from
- Q is chosen from O, S and NR17;
- Y is chosen from O, S, NR17 and NOH;
- Z is chosen from OH, SH, CN and NH2;
- R1 is chosen from hydrogen, lower alkoxy, phenyl and —NHR8;
- 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;
- R5 is lower alkyl;
- R6 is lower alkyl;
- R7 is chosen from hydrogen and hydroxy;
- or together R4, R5, R6 and R7 may form from one to three rings, said rings having optional additional substitution;
- R8 is chosen from hydrogen, —OH, —NH2 and —CH2R15;
- R15 is chosen from hydrogen, alkyl, aryl, substituted aryl and alkyl substituted with alkoxy, amino, alkylamino or dialkylamino;
- R16 is chosen from hydrogen and NH2;
- and
- R17 is chosen from hydrogen, alkyl, aryl and benzyl.
Dependencies are inferred from the claim text.