Piperazine substituted aryl benzodiazepines

US7384934B2 · kind B2 · utility

Assignee

• ELI LILLY AND COMPANY · US

Inventors

• Thomas D. Aicher · Ann Arbor, US
• Zhaogen Chen · Carmel, US
• Yvan LeHuerou · Boulder, US
• Fionna Mitchell Martin · Grafton, GB
• Marta Pineiro-Nunez · Brownsburg, US
• Vincent Patrick Rocco · Indianapolis, US
• Kevin Michael Ruley · Indianapolis, US
• John M. Schaus · Zionsville, US
• Patrick Gianpietro Spinazze · Avon, US
• David E. Tupper · Reading, GB

Key dates

• Filing date: Jul 28, 2003
• Grant date: Jun 10, 2008
• Expiry date: Aug 18, 2023

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D513/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Described herein are compounds of formula (I) wherein: is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, S, and O; Alk is (C1-4) alkylene or hydroxy substituted (C1-4) alkylene; X is oxygen or sulfur; R1 is hydrogen, (C1-6) fluroalkyl, (C3-6) cycloalkyl, or (C1-4) alkyl, wherein the (C1-4) alkyl is unsubstituted or substituted with hydroxy, methoxy, ethoxy, OCH2CH2OH, or —CN; R2 is H, halogen, (C1-6) fluoroalkyl, (C1-6) cycloalkyl, OR4, SR4, NO2, CN, COR4, C(O)OR4, CONR5R6, NR5R6, SO2NR5R6, NR5COR4, NR5SO2R4, optionally substituted aromatic, or (C1-6) alkyl, wherein (C1-6) alkyl is unsubstituted or substituted with a hydroxy group; R3 is hydrogen (C1-6) fluoroalkyl, (C2-6) alkenyl, Ar, (C1-4)alkyl-Ar, or (C1-4) alkyl wherein (C1-4) alkyly is unsubstituted or substituted with a phenyl; R4 is hydrogen, (C1-6) alkyl, (C1-6) fluoroalkyl, or optionally substituted aromatic; R5 and R6 are independently hydrogen, (C1-6) alkyl, or optionally substituted aromatic, R7 is hydrogen, (C1-6) alkyl, (C1-6) fluoroalkyl, or optionally substituted aromatic; R8 and R9 are independently hydrogen, (C1-6) alkyl, or optionally s…