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US 6,784,292 B2Granted
Method for the production of imidazo-(1,2-C)(2,3)-benzodiazepines and intermediates in the production thereof
AssigneeSchering Corporation
InventorsEric Winter, Matthias Schneider, Ulf Tilstam
Life of this patent
Estimating the term…
Abstract
The invention relates to a method for the preparation of compound of formula (1). The invention further relates to the previously unknown compounds of formulas (5 and 6) as intermediates in the production of benzodiazepines of formula (1).
Claims8
A process for the production of imidazo[1,2-c][2,3]benzodiazepines of formula (1)
- in which
- R1=is hydrogen, C1-C6-alkyl, nitro, halogen, cyano, C1-C4-alkoxy, —CF3, hydroxy or C1-C6-alkanoyloxy,
- R2 and R3 are the same or different and mean hydrogen, halogen, C1-C6-alkoxy, hydroxy, cyano, C1-C6-alkanoyl, C2-C6-alkynyl, C2-C6-alkenyl;
- C1-C6-alkyl or C3-C7-cycloalkyl which in each case is unsubstituted or substituted by halogen, hydroxy or C1-6-alkoxy, or an aryl or hetaryl radical which in each case is unsubstituted or substituted by halogen, C1-4-alkoxy or C1-4-alkyl,
- X=is hydrogen or halogen,
- Y=is C1-C6-alkoxy, or
- X and Y together mean —O—(CH2)n—O—, and
- n=is 1, 2 or 3,
- from a phenylacetic acids of formula (4),
- which process comprises:
- a) esterifying the phenylacetic and with an alcohol of formula (5a)
- to form a phenylethyl acetate of formula (5)
- b) condensing the phenylethyl acetate with ammonia or an ammonia donor to form an oxazole of formula (6)
- c) hydrazinolyzing the oxazole to form the compounds of general formula (1)
11 more elements
A phenylacetic acid ester of formula 5,
- in which
- R1=is hydrogen, C1-C6-alkyl, nitro, halogen, cyano, C1-C4-alkoxy, —CF3, hydroxy or C1-C6-alkanoyloxy,
- R2 and R3 are the same or different and mean hydrogen, halogen, C1-C6-alkoxy, hydroxy, cyano, C1-C6-alkanoyl, C2-C6-alkynyl, C2-C6-alkenyl;
- C1-C6-alkyl or C3-C7-cycloalkyl which in each case is unsubstituted or substituted by halogen, hydroxy or C1-6-alkoxy;
- or an aryl or hetaryl radical which in each case is unsubstituted or substituted by halogen, C1-4-alkoxy or C1-4-alkyl,
- X=is hydrogen or halogen,
- Y=C1-C6-alkoxy, or
- X and Y together mean —O—(CH2)n—O—, and
- n=is 1, 2 or 3.
6 more elements
An oxazole compound of formula 6,
- in which
- R1=is hydrogen, C1-C6-alkyl, nitro, halogen, cyano, C1-C4-alkoxy, —CF3, hydroxy or C1-C6-alkanoyloxy,
- R2 and R3 are the same or different and mean hydrogen, halogen, C1-C6-alkoxy, hydroxy, cyano, C1-C6-alkanoyl, C2-C6-alkynyl, C2-C6-alkenyl;
- C1-C6-alkyl or C3-C7-cycloalkyl o which in each case is unsubstituted or substituted by halogen, hydroxy or C1-6-alkoxy;
- or an aryl or hetaryl radical which in each case is unsubstituted or substituted by halogen, C1-4-alkoxy or C1-4-alkyl,
- X=is hydrogen or halogen,
- Y=is C1-C6-alkoxy or
- X and Y together mean —O—(CH2)n—O—, and
- n=1, 2 or 3.
6 more elements
Dependencies are inferred from the claim text.