Calcium salts of 1,5-benzodiazepine derivatives, process for producing the salts and drugs containing the same
AssigneeZeria Pharmaceutical Co., Ltd.
InventorsKatsuo Shinozaki, Masakazu Murata, Kiyoto Maeda, Hiroaki Taguchi, Nobuo Kawase, Naoyoshi Miura
Life of this patent
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Abstract
Provided are calcium salts of a 1,5-benzodiazepine derivative represented by the following formula (I): (wherein, R1 represents a lower alkyl group, R2 represents a phenyl or cyclohexyl group, and Y represents a single bond or a lower alkylene group); a process for preparing the salts; and drugs containing the same as the active ingredient. The compounds exhibit a potent inhibitory activity against the secretion of gastric acid and potent antagonism against gastrin and/or CCK-B receptor.
Claims25
A calcium salt of a 1,5-benzodiazepine compound represented by the following formula (I):
- wherein, R1 represents a lower alkyl group,
- R2 represents a phenyl or cyclohexyl group, and
- Y represents a single bond or a lower alkylene group.
A process for preparing a calcium salt of a 1,5-benzodiazepine compound represented by the following formula (I):
- wherein, R1 represents a lower alkyl group,
- R2 represents a phenyl or cyclohexyl group and
- Y represents a single bond or a lower alkylene group, which comprises
- adding aqueous ammonia to a 1,5-benzodiazepine compound represented by the following formula (II):
- wherein, R1, R2 and Y have the same meanings as defined above, and then treating the resulting mixture by the addition of calcium chloride.
A process for preparing a 1,5-benzodiazepine compound represented by the following formula (II):
- wherein, R1 represents a lower alkyl group,
- R2 represents a phenyl or cyclohexyl group and
- Y represents a single bond or a lower alkylene group,
- which comprises
- reacting an oxalate of a 3-amino-1,5-benzodiazepine compound represented by the following formula (III):
- wherein, R1 and R2 have the same meanings as defined above,
- with a compound represented by the following formula (IV):
- wherein, Y has the same meaning as defined above.
A process for preparing a calcium salt of a 1,5-benzodiazepine compound represented by the following formula (I):
- wherein, R1 represents a lower alkyl group,
- R2 represents a phenyl or cyclohexyl group and
- Y represents a single bond or a lower alkylene group, which comprises
- reacting an oxalate of a 3-amino-1,5-benzodiazepine compound represented by the following formula (III):
- wherein, R1 and R2 have the same meanings as defined above,
- with a compound represented by the following formula (IV):
- wherein, Y has the same meaning as defined above,
- adding aqueous ammonia to the resulting 1,5-benzodiazepine compound represented by the following formula (II)
- wherein, R1, R2 and Y have the same meanings as defined above and then treating the resulting derivative by the addition of calcium chloride.
A process for preparing a 1,5-benzodiazepine compound represented by the following formula (II):
- wherein, R1 represents a lower alkyl group,
- R2 represents a phenyl or cyclohexyl group and
- Y represents a single bond or a lower alkylene group,
- which comprises
- reacting an oxalate of a 3-amino-1,5-benzodiazepine compound represented by the following formula (III):
- wherein, R1 and R2 have the same meanings as defined above with a compound represented by the following formula (IX):
- wherein, X represents a halogen atom and then
- reacting the resulting 3-phenoxycarbonylamino compound represented by the following formula (X):
- wherein, R1 and R2 have the same meanings as defined above,
- with a 3-substituted aniline compound represented by the following formula (XI):
- wherein, R3 represents a hydrogen atom or a metal atom and
- Y has the same meaning as defined above.
A process for preparing a calcium salt of a 1,5-benzodiazepine compound represented by the following formula (I):
- wherein, R1 represents a lower alkyl group,
- R2 represents a phenyl or cyclohexyl group, and
- Y represents a single bond or a lower alkylene group,
- which comprises
- reacting an oxalate of a 3-amino-1,5-benzodiazepine compound represented by the following formula (III):
- wherein, R1 and R2 have the same meanings as defined above,
- with a 3-substituted aniline compound represented by the following formula (XI):
- wherein, X represents a halogen atom;
- reacting the resulting 3-phenoxycarbonylamino compound represented by the following formula (X):
- wherein, R1 and R2 have the same meanings as defined above,
- with a 3-substituted aniline compound represented by the following formula (XI):
- wherein, R3 represents a hydrogen atom or a metal atom and Y has the same meaning as defined above;
- adding aqueous ammonia to the resulting 1,5-benzodiazepine compound represented by the following formula (II):
- wherein, R1, R2 and Y have the same meanings as defined above,
- and then treating the resulting mixture by adding thereto calcium chloride.
Dependencies are inferred from the claim text.