Process for the preparation of 1,2,4-oxadiazol-3-yl derivatives of carboxylic acid
AssigneeAbbott Laboratories
InventorsKirill A. Lukin, Vimal Kishore, Thomas D. Gordon
Life of this patent
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Abstract
The present invention discloses processes for the preparation and isolation of [1,2,4]oxadiazo-3-yl derivatives of carboxylic acids. The derivatives are useful in the treatment of inflammatory diseases and conditions.
Claims20
A process for the preparation of a compound of Formula 4
- comprising the step of reacting compound of Formula 3
- with a compound of Formula 5
- in the presence of activators such as TPP, DEAD or DIAD until the reaction is substantially complete to form a compound of Formula 4
A process for the preparation of a compound of Formula 6
- comprising the steps of reacting hydroxylamine with a compound of Formula 4
- until the reaction is substantially complete, forming a compound of Formula 6
A process for the preparation of a compound of Formula 8
- comprising the step of reacting compounds 6 and 7 in the presence of an activator such as carbonyldiimidazole, HATU or HOBT
- until the reaction is substantially complete to form a compound of Formula 8
A process for the preparation of a compound of Formula 9
- comprising of the cyclization of a compound of Formula 8
- in the presence of a base such as tetrabutylammonium fluoride, diisopropylethylamine, DBU, or tetramethylguanidine until the reaction is substantially complete to form a compound of Formula 9
A process for the preparation of a compound of Formula 2
- comprising the steps of reacting a compound of Formula 9
- with triethylamine and trimethylsilyl triflate until the reaction is substantially complete to form a compound of Formula 2
A process for the preparation of a compound of Formula 18
- comprising the step of reacting the compounds of Formula 15 and Formula 16
- in the presence of a base such as potassium carbonate until the reaction is substantially complete to form a compound of Formula 18
A process for the preparation of a compound of Formula 19
- wherein R is alkyl, comprising the step of reacting a compound of Formula 18
- in a solution of hydrogen chloride gassed into an alcohol until the reaction is substantially complete to form a compound of Formula 19
A process for the preparation of a compound of Formula 20
- wherein R is alkyl, comprising the step of reacting a compound of Formula 19
- with hydroxylamine until the reaction is substantially complete to form a compound of Formula 20
A process for the preparation of a compound of Formula 21
- wherein R is alkyl, comprising the step of reacting a compound of Formula 20
- with DBU in THF until the reaction is substantially complete to form a compound of Formula 21
- .
A process for the preparation of a compound of Formula 22
- wherein R is alkyl, comprising the step of reacting a compound of Formula 21
- with DBU in THF until the reaction is substantially complete to form a compound of Formula 22
A process for the preparation of a compound of Formula 23
- comprising the step of reacting sodium hydroxide and a compound of Formula 22
- wherein R is alkyl, until the reaction is substantially complete to form a compound of Formula 23
A process for the preparation of a compound of Formula 26
- comprising the step of reacting compounds of Formula 24 and 25
- in the presence of an activator such as carbonyldiimidazole, HATU or HOBT until the reaction is substantially complete to form a compound of Formula 26
A process for the preparation of a compound of Formula 27
- comprising of cyclization of a compound of Formula 26
- in the presence of a base such as until the reaction is substantially complete to form a compound of Formula 27
A process for the preparation of a compound of Formula 28
- comprising the step of reacting a compound of Formula 27
- with pyridine and oxalyl chloride until the reaction is substantially complete to form a compound of Formula 28
A process for the preparation of a compound of Formula 29
- comprising the step of reacting a compound of Formula 28
- with alkyl acrylate until the reaction is substantially complete to form a compound of Formula 29
A process for the preparation of a compound of Formula 30
- comprising the steps of reacting a compound of Formula 29
- with sodium hydroxide until the reaction is substantially complete to form a compound of Formula 30
A process for the preparation of a compound of Formula 10
- comprising the step of reacting the mixture of compounds of Formulas 3a and 3b
- with a compound of Formula 5
- until the reaction is substantially complete to form a compound of Formula 10
A process for the preparation of a compound of Formula 11
- comprising the steps of reacting hydroxylamine with a compound of Formula 10
- until the reaction is substantially complete, forming a compound of Formula 11
A process for the preparation of a compound of Formula 13
- comprising the step of reacting carbonyldiimidazole with compounds 11 and 12
- until the reaction is substantially complete to form a compound of Formula 13
A process for the preparation of a compound of Formula 14
- comprising the step of reacting a compound of Formula 13
- with sodium hydroxide until the reaction is substantially complete to form a compound of Formula 14
Dependencies are inferred from the claim text.