US4351770A
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US
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Preparation of N(2-pyrrolidinylmethyl)2-methoxy-5-benzenesulfonamidobenzamides
Assignee: Shionogi and Co Ltd
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Filing: 1978-12-06
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Granted: 1982-09-28
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Expires: 1998-12-06
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-emitic 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
2026-11-08 14:31
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: 2
Claim 1
Independent Claim
277 words
A process for preparing a meta-sulfonamidobenzamide compound of the formula: ##STR21## wherein R is hydrogen or methyl, R 1 is C 1 -C 6 alkyl, phenyl, 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, and R 5 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, benzyl or halobenzyl, or a pharmaceutically acceptable acid addition salt of said compound, which comprises the step of reacting an anilino compound of the formula: ##STR22## wherein R 2 , R 3 , R 4 and R 5 each is as defined above, with a sulfonating agent of the formula: A-SO.sub.2 R.sup.1 wherein A is chlorine or bromine, and R 1 is as defined above, in an inert solvent in the presence of 2.0 or more mol equivalents of triethylamine at a temperature of 0°-100° C. to yield a disulfonamide of the formula: ##STR23## wherein R 1 , R 2 , R 3 , R 4 and R 5 each is as defined above, or a mixture of said disulfonamide and a monosulfonamide of the formula: ##STR24## wherein R 1 , R 2 , R 3 , R 4 and R 5 each is as defined above, hydrolyzing said disulfonamide with aqueous alkali hydroxide in methanol with heating on a water bath to yield said monosulfonamide, and, if said meta-sulfonamidobenzamide compound wherein R is methyl is desired, subjecting said monosulfonamide to methylation.
Claim 2
Dependent Claim
277 words
A process for preparing a meta-sulfonamidobenzamide compound of the formula: ##STR21## wherein R is hydrogen or methyl, R 1 is C 1 -C 6 alkyl, phenyl, 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, and R 5 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, benzyl or halobenzyl, or a pharmaceutically acceptable acid addition salt of said compound, which comprises the step of reacting an anilino compound of the formula: ##STR22## wherein R 2 , R 3 , R 4 and R 5 each is as defined above, with a sulfonating agent of the formula: A-SO.sub.2 R.sup.1 wherein A is chlorine or bromine, and R 1 is as defined above, in an inert solvent in the presence of 2.0 or more mol equivalents of triethylamine at a temperature of 0°-100° C. to yield a disulfonamide of the formula: ##STR23## wherein R 1 , R 2 , R 3 , R 4 and R 5 each is as defined above, or a mixture of said disulfonamide and a monosulfonamide of the formula: ##STR24## wherein R 1 , R 2 , R 3 , R 4 and R 5 each is as defined above, hydrolyzing said disulfonamide with aqueous alkali hydroxide in methanol with heating on a water bath to yield said monosulfonamide, and, if said meta-sulfonamidobenzamide compound wherein R is methyl is desired, subjecting said monosulfonamide to methylation.
References Cited (Backward Citations)
US2334186A
Cited
US3341584A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1985-09-27 | 1986-03-29 | 1986-09-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-27 | 1990-03-29 | 1990-09-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-27 | 1994-03-29 | 1994-09-28 | $7700.00 | Window Closed / Lapsed |