Back to results
US 6,686,474 B2Granted
Process for the production of antiulceratives
AssigneeGruenenthal GmbH
InventorsHartmut Loebermann, Karl-Heinz Caster
Life of this patent
Estimating the term…
Abstract
A method for the production of an antiulcerative via reacting reacting a compound of formula II: with m-chloroperoxybenzoic acid in a solvent of acetone or acetone/water mixture to form a reaction mixture. The reaction mixture has a pH of 7.0 or above, and crystals of the antiulcerative compound of formula I are formed which may be optionally separated.
Claims41
A method for the production of an antiulcerative of formula I:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 fluoroalkyl and C1-C8 alkoxy,
- R4 and R5 are independently selected from the group consisting of hydrogen, C1-C8 alkyl, C3-C8 cycloalkyl, CH2—C3-C8 cycloalkyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy, C1-C8 fluoroalkoxy, CF3, C2-C8 fluoroalkyl and C(O)O—C1-C8 alkyl, and
- R6 is hydrogen or C1-C2 alkyl,
- wherein the method comprises
- reacting a compound of formula II:
- wherein R1, R2, R3, R4, R5 and R6 are defined as above,
- with m-chloroperoxybenzoic acid in a solvent selected from the group consisting of acetone and acetone/water mixture to form a reaction mixture,
- raising the pH of the reaction mixture to above pH 7.0, whereby crystals of the compound of formula I are formed, and
- separating the crystals of the compound of formula I.
7 more elements
A method for the production of an antiulcerative of formula I:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 fluoroalkyl and C1-C8 alkoxy,
- R4 and R5 are independently selected from the group consisting of hydrogen, halogen, C1-C8 alkyl, C3-C8 cycloalkyl, CH2—C3-C8 cycloalkyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy, C1-C8 fluoroalkoxy, CF3, C2-C8 fluoroalkyl and C(O)O—C1-C8 alkyl, and
- R6 is hydrogen or C1-C2 alkyl,
- wherein the method comprises
- reacting a compound of formula II:
- wherein R1, R2, R3, R4, R5 and R6 are defined as above,
- with m-chloroperoxybenzoic acid in a solvent selected from the group consisting of acetone and acetone/water mixture with a pH of ≧7.0 to form crystals of the compound of formula I, and
- separating the crystals.
6 more elements
Dependencies are inferred from the claim text.