Substituted 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines and their use as pharmaceutical compositions

US6387921B1 · kind B1 · utility

Assignee

• BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG · DE

Inventors

• Matthias Grauert · Ingelheim am Rhein, DE
• Adrian Carter · Bingen, DE
• Thomas Weiser · Nieder-Olm, DE
• Helmut Ensinger · Wackernheim, DE
• Wolfram Gaida · Ingelheim am Rhein, DE
• Joachim Mierau · Mainz, DE

Key dates

• Filing date: Nov 27, 2001
• Grant date: May 14, 2002
• Expiry date: Nov 27, 2021

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D221/26
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Substituted 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines of general formula 1: wherein:R1 and R2, which are identical or different, are each hydrogen, C1-C6-alkyl, C1--C6-alkyloxy, OH, F, Cl, or Br;R3 is hydrogen, F, Cl, Br, methyl, ethyl, OH, or methoxy;R4 and R5, which are identical or different, are each hydrogen, methyl, or ethyl;R6 is hydrogen;X is NH2, NH—(C1-C6-alkyl), N(C1-C6-alkyl)2, the two C1-C6-alkyl groups of which are identical or different, NH—COH, NH—CO(C1-C6-alkyl), or F;A is —(CH2)3—, —CH2—CH2—O—, —CH2—O—CH2—, —(CH2)4—, —CH(C1-C6-alkyl)-O—CH2—, —(CH2)2—O—CH2—, —(CH2)3—O—, —(CH2)5—, —CH2—O—(CH2)3—, —(CH2)2—O—(CH2)2—, —(CH2)3—O—CH2—, —(CH2)4—O—, —CH2—O—CH2—CH2—O—, the racemates thereof, the enantiomers thereof, the diastereomers thereof, and mixtures thereof, and the pharmacologically acceptable acid addition salts thereof, processes for preparing them, and their use as pharmaceu…