Method for the preparation of (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1-6-naphthyridine-3-carboxamide and the purification thereof for use as an active pharmaceutical ingredient
AssigneeBayer Pharma Aktiengesellschaft
InventorJohannes Platzek
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Abstract
The present invention relates to a novel and improved process for preparing (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula (I)
Claims25
A process for preparing a compound of the formula (I)
- comprising separating a racemic compound of the formula (XIII) into its enantiomers, wherein the compound of the formula (XIII)
- is prepared by reacting a compound of the formula (XVIII)
- with an orthoester (XX)
- where R may be H or methyl, wherein
- the compound of the formula (XVIII)
- is prepared by reacting compounds of the formula (XVI a,b)
- with a compound of the formula (IX)
- and wherein
- the compound of the formula (XVI a,b) is prepared by reacting a compound of the formula (VI)
- with a compound of the formula (XVII)
A process for preparing a compound of the formula (I)
- comprising separating a racemic compound of the formula (XIII) into its enantiomers, where the compound of the formula (XIII)
- is prepared by reacting a compound of the formula (XVIII)
- with an orthoester (XX)
- where R may be H or methyl, and wherein
- the compound of the formula (XVIII)
- is prepared by reacting compounds of the formula (XVI a,b)
- with a compound of the formula (IX)
A process for preparing a compound of the formula (I)
- comprising separating a racemic compound of the formula (XIII) into its enantiomers, where the compound of the formula (XIII)
- is prepared by reacting a compound of the formula (XVIII)
- with an orthoester (XX)
- where R may be H or methyl.
A process for preparing a compound of the formula (I)
- comprising using the compound of the formula (XVIII)
A process for preparing a compound of the formula (I)
- comprising using the compounds of the formula (XVI a,b)
A process for preparing a compound of the formula (I)
- comprising using a compound of the formula (XVIII)
- and
- compounds of the formula (XVI a,b)
A compound of the formula (XVIII)
- and the salts, solvates and solvates of the salts thereof.
A compound of the formula (XVI a,b) as an E/Z mixture
- and the salts, solvates and solvates of the salts thereof.
A process for preparing a compound of the formula (XVIII)
- comprising reacting compounds of the formula (XVI a,b)
- with a compound of the formula (IX)
A process for preparing compounds of the formula (XVI a,b)
- comprising reacting a compound of the formula (VI)
- with a compound of the formula (XVII)
A process for preparing a compound of the formula (XIII)
- comprising reacting a compound of the formula (XVIII)
- with an orthoester (XX)
- where R may be H or methyl.
A process for preparing a compound of the formula (XIII)
- comprising reacting a compound of the formula (XVIII)
- with an orthoester (XX)
- where R may be H or methyl, and wherein
- the compound of the formula (XVIII) is prepared by reacting compounds of the formula (XVI a,b)
- with a compound of the formula (IX)
A process for preparing a compound of the formula (I)
- comprising separating a racemic compound of the formula (XIII) into its enantiomers,
- wherein the compound of the formula (XIII)
- is prepared by reacting a compound of the formula (XVIII)
- with an orthoester (XX)
- where R may be H or methyl, wherein
- the compound of the formula (XVIII)
- is prepared by reacting compounds of the formula (XVI a,b)
- with a compound of the formula (IX)
- and wherein
- the compound of the formula (XVI a,b) is prepared by reacting a compound of the formula (VI)
- with a compound of the formula (XVII)
A process for preparing a compound of the formula (I)
- comprising separating a racemic compound of the formula (XIII) into its enantiomers,
- where the compound of the formula (XIII)
- is prepared by reacting a compound of the formula (XVIII)
- with an orthoester (XX)
- where R may be H or methyl, and wherein
- the compound of the formula (XVIII)
- is prepared by reacting compounds of the formula (XVI a,b)
- with a compound of the formula (IX)
A process for preparing a compound of the formula (I)
- comprising using the compounds of the formula (XVI a,b)
- comprising reacting the compounds of the formula (XVI a,b) with a compound of the formula (IX)
A process for preparing a compound of the formula (I)
- comprising using a compound of the formula (XVIII)
- and
- compounds of the formula (XVI a,b)
- comprising reacting the compound of the formula (XVIII) with an orthoester (XX)
- wherein the compound of the formula (XVIII) is prepared by reacting the compounds of the formula (XVI a,b) with a compound of the formula (IX)
A compound of the formula (XVI a,b) as an E/Z mixture
- and the salts, solvates and solvates of the salts thereof.
A process for preparing a compound of the formula (XVIII)
- comprising reacting compounds of the formula (XVI a,b)
- with a compound of the formula (IX)
A process for preparing compounds of the formula (XVI a,b)
- comprising reacting a compound of the formula (VI)
- with a compound of the formula (XVII)
A process for preparing a compound of the formula (XIII)
- comprising reacting a compound of the formula (XVIII)
- with an orthoester (XX)
- where R may be H or methyl, and wherein
- the compound of the formula (XVIII) is prepared by reacting compounds of the formula (XVI a,b)
- with a compound of the formula (IX)
Dependencies are inferred from the claim text.