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US4330472A
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Meta-sulfonamido-benzamide derivatives
Assignee: Shionogi and Co Ltd
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Filing: 1980-06-25
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Granted: 1982-05-18
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Expires: 2000-06-25
Abstract
Abstract Meta-sulfonamido-benzamide derivatives of the formula: ##STR1## [wherein R is a hydrogen atom or a lower alkyl, cyano, or lower alkanesulfonyl group; R 1 is a lower alkyl, phenyl, amino, lower alkylamino, di(lower)alkylamino, or C 4 -C 5 alkyleneamino group; R 2 is a hydrogen or halogen atom or a lower alkyl, di(lower)alkylamino, or lower alkoxy group; R 3 is a hydrogen atom or a methyl or methoxy group; R 4 is a hydrogen or halogen atom; R 5 is a lower alkyl, lower alkenyl, C 3 -C 6 cycloalkyl, benzyl, or halogenobenzyl group; and n is 1 or zero] or their acid addition salts, showing pharmacological activity such as anti-emetic or psychotropic activity, are provided via several routes.
Inventors
- 👤 Masaru Ogata
- 👤 Hiroshi Matsumoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 22:41
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/14; C07D207/08; C07D207/09; C07D307/00; C07D307/02; C07D307/04; C07D307/10; C07D307/14
Claims Analysis
Total Claims: 3
Claim 1
Independent Claim
232 words
A process for preparing a compound of the formula: ##STR22## wherein R is hydrogen, C 1 -C 6 alkyl, cyano or C 1 -C 6 alkanesulfonyl, R 1 is C 1 -C 6 alkyl, phenyl, amino, C 1 -C 6 alkylamino, C 2 -C 12 dialkylamino or C 4 -C 5 alkyleneamino, R 2 is hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 12 dialkylamino or C 1 -C 6 alkoxy, R 3 is hydrogen, methyl or methoxy, R 4 is hydrogen or halogen, R 5 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, benzyl or halobenzyl, and n is zero or 1, or a pharmaceutically acceptable acid addition salt of said compound, which comprises the steps of reacting a tetrahydrofuryl compound of the formula: ##STR23## wherein R, R 1 , R 2 , R 3 , R 4 and n are each as defined above, with thionyl chloride in an inert solvent at a temperature above room temperature, and isolating and reacting the resultant dichloro compound of the formula: ##STR24## wherein R, R 1 , R 2 , R 3 , R 4 and n are each as defined above, with an amino compound of the formula: R.sup.5 --NH.sub.2 wherein R 5 is as defined above, in the presence or absence of a suitable solvent at a temperature above room temperature.
Claim 2
Dependent Claim
232 words
A process for preparing a compound of the formula: ##STR22## wherein R is hydrogen, C 1 -C 6 alkyl, cyano or C 1 -C 6 alkanesulfonyl, R 1 is C 1 -C 6 alkyl, phenyl, amino, C 1 -C 6 alkylamino, C 2 -C 12 dialkylamino or C 4 -C 5 alkyleneamino, R 2 is hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 12 dialkylamino or C 1 -C 6 alkoxy, R 3 is hydrogen, methyl or methoxy, R 4 is hydrogen or halogen, R 5 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, benzyl or halobenzyl, and n is zero or 1, or a pharmaceutically acceptable acid addition salt of said compound, which comprises the steps of reacting a tetrahydrofuryl compound of the formula: ##STR23## wherein R, R 1 , R 2 , R 3 , R 4 and n are each as defined above, with thionyl chloride in an inert solvent at a temperature above room temperature, and isolating and reacting the resultant dichloro compound of the formula: ##STR24## wherein R, R 1 , R 2 , R 3 , R 4 and n are each as defined above, with an amino compound of the formula: R.sup.5 --NH.sub.2 wherein R 5 is as defined above, in the presence or absence of a suitable solvent at a temperature above room temperature.
Claim 3
Dependent Claim
63 words
A process as claimed in claim 1, wherein R in the resulting product is hydrogen, and said product is subjected to C 1 -C 6 alkylation in the presence of an inorganic base in an inert solvent at a temperature of from above room temperature to the boiling point of the solvent, to convert R to a C 1 -C 6 alkyl group.
References Cited (Backward Citations)
US4021567A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-05-17 | 1985-11-16 | 1986-05-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-05-17 | 1989-11-16 | 1990-05-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-05-17 | 1993-11-16 | 1994-05-18 | $7700.00 | Window Closed / Lapsed |