Patent US4267175A successfully refreshed from Google Patents.
US4267175A
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US
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Benzamide derivatives
Assignee: Beecham Group PLC
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Filing: 1979-03-08
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Granted: 1981-05-12
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Expires: 1999-03-08
Abstract
Abstract A compound of the formula (I), and pharmaceutically acceptable salts thereof: ##STR1## wherein: R 1 is a C 1-6 alkoxy group; R 2 and R 3 are the same or different and are hydrogen, halogen, CF 3 , hydroxy, C 1-6 alkoxy, C 2-7 acyl, amino, amino substituted by one or two C 1-6 alkyl groups, C 2-10 acyl amino, aminosulphone, aminosulphone substituted by one or two C 1-6 alkyl groups, C 1-6 alkyl sulphone or nitro groups; and A is a C 2-4 alkylene group; R 5 and R 6 are joined so that they form with the --N--A--N-- group to which they are attached, a 6, 7 or 8 membered heterocyclic ring; R 7 is a C 1-6 alkyl group, or an aryl --C 1-6 akyl group in which the alkyl moiety is optionally substituted by a C 1-6 alkyl or aryl group; have useful pharmacological activity, such as the ability to regulate the gastrointestinal function and to treat emesis.
Inventors
- 👤 Eric A. Watts
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 18:44
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/22; C07D295/28; A; A61; A61P; A61P1/00; A61P1/04; A61P1/08; A61P25/00; A61P25/04; C07C; C07C243/00; C07C243/24; C07C243/38; C07D243/00; C07D243/06; C07D243/08; C07D295/32
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
109 words
A compound of the formula: ##STR22## and the pharmaceutically acceptable acid addition and quaternary salts thereof, wherein R 1 is alkoxy of 1 to 6 carbon atoms; R 2 is --NH 2 or alkanoylamino of 2 to 7 carbon atoms; R 3 is hydrogen or halo; R 7 is alkyl of 1 to 6 carbon atoms unsubstituted or monosubstituted with phenyl, said phenyl being unsubstituted or monosubstituted by halo, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, hydroxy, nitro, trifluoromethyl, amino, or mono- or dialkylamino wherein alkyl contains from 1 to 6 carbon atoms; and a has a value of 2 or 3.
Claim 2
Dependent Claim
109 words
A compound of the formula: ##STR22## and the pharmaceutically acceptable acid addition and quaternary salts thereof, wherein R 1 is alkoxy of 1 to 6 carbon atoms; R 2 is --NH 2 or alkanoylamino of 2 to 7 carbon atoms; R 3 is hydrogen or halo; R 7 is alkyl of 1 to 6 carbon atoms unsubstituted or monosubstituted with phenyl, said phenyl being unsubstituted or monosubstituted by halo, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, hydroxy, nitro, trifluoromethyl, amino, or mono- or dialkylamino wherein alkyl contains from 1 to 6 carbon atoms; and a has a value of 2 or 3.
Claim 3
Dependent Claim
21 words
The compound according to claim 1 wherein R 7 is benzyl, chlorobenzyl, methoxybenzyl or alkyl of 1 to 6 carbon atoms.
Claim 4
Dependent Claim
12 words
A compound as claimed in claim 1 wherein R 2 is amino.
Claim 5
Dependent Claim
12 words
A compound as claimed in claim 3 wherein R 3 is chloro.
Claim 6
Dependent Claim
12 words
A compound as claimed in claim 4 wherein R 1 is methoxy.
Claim 7
Dependent Claim
11 words
A compound according to claim 1 wherein R 2 is alkanoylamino.
Claim 8
Dependent Claim
11 words
A compound according to claim 6 wherein R 2 is acetylamino.
Claim 9
Dependent Claim
13 words
A compound according to claim 1 wherein a has a value of 2.
Claim 10
Dependent Claim
17 words
A compound according to claim 1 wherein R 7 is alkyl of 1 to 6 carbon atoms.
Claim 11
Dependent Claim
18 words
A compound according to claim 1 wherein R 7 is phenyl-alkyl wherein alkyl has 1 to 3 carbons.
Claim 12
Dependent Claim
23 words
A compound according to claim 1 wherein R 1 is methoxy, R 2 is amino, R 3 is chloro and a is 2.
Claim 13
Dependent Claim
12 words
A compound as claimed in claim 11 wherein R 7 is phenylalkyl.
Claim 14
Dependent Claim
11 words
A compound according to claim 12 wherein R 7 is benzyl.
Claim 15
Dependent Claim
17 words
A compound according to claim 11 wherein R 7 is alkyl of 1 to 6 carbon atoms.
Claim 16
Dependent Claim
11 words
A compound according to claim 14 wherein R 7 is methyl.
Claim 17
Dependent Claim
11 words
A compound according to claim 14 wherein R 7 is n-butyl.
Claim 18
Dependent Claim
22 words
A compound according to claim 1 which is the hydrochloride, hydrobromide, phosphate, sulfate, citrate, tartarate, lactate or acetate salt of said benzamide.
Claim 19
Dependent Claim
9 words
A compound according to claim 1 which is 4-amino-5-chloro-2-methoxy-N-(4-benzyl-1-piperazinyl)benzamide.
Claim 20
Dependent Claim
9 words
A compound according to claim 1 which is 4-acetylamino-5-chloro-2-methoxy-N-(4-benzyl-1-piperazinyl)-benzamide.
Claim 21
Dependent Claim
9 words
A compound according to claim 1 which is 4-amino-5-chloro-2-methoxy-N-(4-methyl-1-piperazinyl)benzamide.
Claim 22
Dependent Claim
9 words
A compound according to claim 1 which is 4-acetylamino-5-chloro-2-methoxy-N-(4-methyl-1-piperazinyl)benzamide.
Claim 23
Dependent Claim
9 words
A compound according to claim 1 which is 4-amino-5-chloro-2-methoxy-N-(4-ethyl-1-piperazinyl)benzamide.
Claim 24
Dependent Claim
9 words
A compound according to claim 1 which is 4-acetylamino-5-chloro-2-methoxy-N-(4-ethyl-1-piperazinyl)benzamide.
Claim 25
Dependent Claim
9 words
A compound according to claim 1 which is 4-amino-5-chloro-2-methoxy-N-(4-n-butyl-1-piperazinyl)benzamide.
Claim 26
Dependent Claim
44 words
A compound according to claim 1 wherein R 7 is alkyl of 1 to 6 carbon atoms, or phenylalkyl wherein alkyl has 1 to 6 carbon atoms and said phenyl is unsubstituted or substituted by halo, or alkoxy of 1 to 6 carbon atoms.
Claim 27
Dependent Claim
11 words
A compound according to claim 1 wherein R 3 is bromo.
Claim 28
Dependent Claim
20 words
A compound according to claim 11 wherein R 7 is thienylalkyl wherein the alkyl contains 1 to 3 carbon atoms.
Claim 29
Dependent Claim
22 words
A compound according to claim 11 which is the hydrochloride, hydrobromide, phosphate, sulphate, citrate, tartrate, lactate or acetate salt of said benzamide.
Claim 30
Dependent Claim
15 words
A compound according to claim 11 which is a quaternary ammonium salt of said benzamide.
Claim 31
Dependent Claim
10 words
The hydrochloride salt of a compound according to claim 11.
Claim 32
Dependent Claim
22 words
A pharmaceutical composition comprising a pharmacologically effective amount of a compound according to claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 33
Dependent Claim
24 words
A method of regulating gastrointestinal function and effecting an antimetic response in an animal which comprises administration of a compound according to claim 1.
Claim 34
Dependent Claim
9 words
A compound according to claim 1 which is 4-amino-5-chloro-2-methoxy-N-[4-(4-chlorobenzyl)-1-piperazinyl]-benzamide.
Claim 35
Dependent Claim
9 words
A compound according to claim 1 which is 4-amino-5-chloro-2-methoxy-N-[4-(4-methoxybenzyl)-1-piperazinyl]-benzamide
Claim 36
Dependent Claim
9 words
A compound according to claim 1 which is 4-amino-5-chloro-2-methoxy-N-[4-methyl-1-(1,4-diazacycloheptyl)]-benzamide.
Claim 37
Dependent Claim
9 words
A compound according to claim 1 which is 4-chloroacetylamino-5chloro-2-methoxy-N-[4-methyl-1-piperazinyl]-benzamide.
Claim 38
Dependent Claim
9 words
A compound according to claim 1 which is 4-amino-5-chloro-2-methoxy-N-[4-(3-chlorobenzyl)-1-piperazinyl]-benzamide.
References Cited (Backward Citations)
US3177252A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-05-11 | 1984-11-10 | 1985-05-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-05-11 | 1988-11-10 | 1989-05-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-05-11 | 1992-11-10 | 1993-05-12 | $7700.00 | Window Closed / Lapsed |