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EP0675121A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Novel intermediates and processes for preparing benzothiophene compounds

Assignee: Eli Lilly and Co
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Filing: 1995-03-28
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Granted: —
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Expires: 2015-03-28
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Abstract

Abstract The present invention provides a novel process for preparing a compound of formula I wherein R¹ and R² combine to form C₄-C₆ polymethylene, -CH₂CH(CH₃)CH₂CH₂-, -CH₂C(CH₃)₂CH₂CH₂-, or -CH₂CH₂OCH₂CH₂-; or a pharmaceutically acceptable salt or solvate thereof, comprising a) reacting a compound of formula II with a compound of formula III wherein R¹ and R² are as defined above, in the presence of triphenylphosphine and diethyl azodicarboxylate; or b) reacting a compound of formula II with a compound of formula Z-CH₃-CH₂-Z in which Z is the same or different leaving group, and reacting the resulting compound of formula IV wherein Z is a leaving group, with pyrrolidine, piperidine, hexamethyleneimine, methylpyrrolidine, dimethylpyrrolidine, or morpholine; c) deprotecting the 6- and 4'-position hydroxy group of the reaction product of step a) or step b); and d) optionally salifying or forming a solvate of the reaction product of step c). Also provided are novel intermediates of formulae II and IV wherein Z is a leaving group.

Inventors

  • 👤 Jeffrey Alan Dodge
  • 👤 Mark Gregory Stocksdale

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-23 17:57
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D333/56; A; A61; A61P; A61P19/00; A61P19/08; A61P19/10; A61P3/00; A61P43/00

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 139 words
A process for preparing a compound of formula I wherein R¹ and R² combine to form C₄-C₆ polymethylene, -CH₂CH(CH₃)CH₂CH₂-, -CH₂C(CH₃)₂CH₂CH₂-, or -CH₂CH₂OCH₂CH₂-; or a pharmaceutically acceptable salt or solvate thereof, comprising a) reacting a compound of formula II with a compound of formula III wherein R¹ and R² are as defined above, in the presence of triphenylphosphine and diethyl azodicarboxylate; or b) reacting a compound of formula II with a compound of formula Z-CH₃-CH₂-Z in which Z is the same or different leaving group, and reacting the resulting compound of formula IV wherein Z is a leaving group, with pyrrolidine, piperidine, hexamethyleneimine, methylpyrrolidine, dimethylpyrrolidine, or morpholine; c) deprotecting the 6- and 4'-position hydroxy group of the reaction product of step a) or step b); and d) optionally salifying or forming a solvate of the reaction product of step c).
Claim 2
Dependent Claim 23 words
A process according to Claim 1 wherein R¹ and R² combine to form C₄ polymethylene and the salt thereof is the hydrochloride salt.
Claim 3
Dependent Claim 19 words
A process according to any one of Claims 1 to 2 wherein steps a), c), and d) are used.
Claim 4
Dependent Claim 19 words
A process according to any one of Claims 1 to 2 wherein steps b), c), and d) are used.
Claim 5
Dependent Claim 15 words
A process according to Claim 4 whrein Z of said formula IV compound is bromo.
Claim 6
Dependent Claim 21 words
A process according to any one of Claims 1 to 5 wherein the process is carried out in a single vessel.
Claim 7
Dependent Claim 140 words
A compound of formula I wherein R¹ and R² combine to form C₄-C₆ polymethylene, -CH₂CH(CH₃)CH₂CH₂-, -CH₂C(CH₃)₂CH₂CH₂-, or -CH₂CH₂OCH₂CH₂-; or a pharmaceutically acceptable salt or solvate thereof, when prepared by the process comprising a) reacting a compound of formula II with a compound of formula III wherein R¹ and R² are as defined above, in the presence of triphenylphosphine and diethyl azodicarboxylate; or b) reacting a compound of formula II with a compound of formula Z-CH₃-CH₂-Z in which Z is the same or different leaving group, and reacting the resulting compound of formula IV wherein Z is a leaving group, with pyrrolidine, piperidine, hexamethyleneimine, methylpyrrolidine, dimethylpyrrolidine, or morpholine; c) deprotecting the 6- and 4'-position hydroxy group of the reaction product of step a) or step b); and d) optionally salifying or forming a solvate of the reaction product of step c).
Claim 8
Dependent Claim 5 words
A compound of formula II
Claim 9
Dependent Claim 16 words
A compound of formula IV wherein Z is a leaving group, particularly bromo, chloro, or iodo.
Claim 10
Dependent Claim 12 words
A compound according to Claim 9 wherein said leaving group is bromo.

References Cited (Backward Citations)

GB1357212A Cited
US4024273A Cited
FR2329271A1 Cited
US4133814A Cited
EP0062505A1 Cited
EP0062504A1 Cited
US4380635A Cited

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