2-aroylalkyl benzomorphans

Abstract

Abstract BENZOMORPHAN DERIVATIVES OF THE FORMULA: 1-R7,1-R8,3-((R3,R4-PHENYL)-CO-(CH2)N-),4-R6,6-R1,8-R, 9-R5,11-R2,1,2,3,4,5,6-HEXAHYDROBENZOMORPHAN WHEREIN R IS A HYDROGEN ATOM, A C1-C3 ALKOXY GROUP, AN ACYLOXY GROUP, A HYDROXY GROUP, A NITRO GROUP, A HALOGEN ATOM, A CYANO GROUP, AN AMINO GROUP, A CARBOXYL GROUP, A CARBAMOYL GROUP OR A SULFO GROUP; R1 IS A HYDROGEN ATOM, A C1-C3 ALKYL GROUP OR A GROUP OF THE FORMULA, (CMH 2M-P!+1)-(R9)P (WHEREIN M IS AN INTEGER OF 1-6; P IS AN INTEGER OF 1-2, AND R9 IS A HYDROXYL GROUP OR A C1-C3 ALKOXY GROUP); R2 IS A HYDROGEN ATOM OR A C1-C3 ALKYL GROUP; R3 AND R4 ARE INDEPENDENTLY A HYDROGEN ATOM, A HALOGEN ATOM, A C1-C3 ALKYL GROUP, A C1-C3 ALKOXY GROUP, A C1-C3 ALKYLTHIO GROUP, A NITRO GROUP, A TRIFLUOROMETHYL GROUP, AN AMINO GROUP OR A HYDROXYL GROUP; R5 IS A HYDROGEN ATOM OR A METHYL GROUP; R6 IS A HYDROGEN ATOM OR A C1-C3 ALKYL GROUP; R7 IS A HYDROGEN ATOM, A C1-C3 ALKYL GROUP, A PHENYL GROUP OR A C1-C3 ALKOXYPHENYL GROUP; R8 IS A HYDROGEN ATOM OR A HYDROXYL GROUP, OR R7 AND R8 MAY FOR A C1-C3 ALKYLIDENE GROUP OR CARBONYL GROUP TOGETHER WITH A CARBON ATOM TO WHICH THESE SUBSTITUTENTS ARE BONDED; AND N IS AN INTEGER OF 2 TEAGER OF 2-4, PROVIDED THAT, WHEN N IS AN INTEGER OF 2, R1 AND R2 ARE A METHKYL GROUP R IS A HYDROGEN ATOM OR A HYDROXYL GROUP AND R4, R5, R6, R7 AND R8 ARE HYDROGEN ATOMS, R3 MUST BE A HALOGEN ATOM, A C1-C3 ALKYL GROUP A C1-C3 ALKOXY GROUP, A C1-C3 ALKYLTHIO GROUP, OR A GROUP, A TRIFLUOROMETHYL GROUP, AN AMINO GROUP OR A HYDROXYL GROUP, WHICH ARE USEFUL AS NON-ADDICTING, ANALGESIC AND PAIN-RELIEVING AGENTS WITH CALMING EFFECT. THESE BENZOMORPHAN DERIVATIVES ARE PREPARED BY REACTING A 6,7-BENZOMORPHAN DERIVATIVE OF THE FORMULA: 1-R7,1-R8,4-R6,6-R1,8-R,9-R5,11-R2,1,2,3,4,5,6-HEXAHYDRO BENZOMORPHAN WHEREIN R, R1, R2, R5, R6, R7 AND R8 ARE AS DEFINED ABOVE, WITH A HALOGEN DERIVATIVE OF THE FORMULA: (X-(CH2)N-C(=Y)-),R3,R4-BENZENE WHEREIN R3, R4 AND N ARE DEFINED ABOVE, X IS A HALOGEN ATOM AND Y IS AN OXYGEN ATOM OR AN ETHYLENEDIOXY GROUP, AND FURTHER, IN THE CASE OF Y=ETHYLENEDIOXY GROUP, BY HYDROLYZING THE RESULTING ETHYLENEDIOXY DERIVATIVE OF THE FORMULA: 1-R7,1-R8,3-((R3,R4-PHENYL)-1,3-DIOXOLAN-2-YLIDINE-(CH2)N -),6-R1,8-R,9-R5,11-R6,1,2,3,4,5,6-HEXAHYDROBENZOMORPHAN WHEREIN R, R1, R2, R3, R4, R5, R6, R7, R8, AND N ARE AS DEFINED ABOVE.

Inventors

• 👤 T Atsumi
• 👤 H Yamamoto
• 👤 K Kobayashi
• 👤 Y Takebayashi

Bibliographic Details