US4159278A
Expired / Lapsed
US
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Dioxamic acids and salts
Assignee: Pharmacia and Upjohn Co
•
Filing: 1977-10-31
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Granted: 1979-06-26
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Expires: 1997-10-31
Abstract
Abstract Compounds represented below <IMAGE> and pharmaceutical compositions thereof, the compositions including the non-substituted phenylene dioxamates are useful in the prophylactic treatment of sensitized mammals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature.
Inventors
- 👤 Charles M. Hall
- 👤 John B. Wright
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 17:50
CPC Classifications
C; C07; C07C; C07C233/00
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
207 words
A compound of the formula ##STR51## wherein W is hydrogen, X, Y, and Z can be the same or different and are selected from the group consisting of hydrogen, alkyl from one to six carbon atoms, inclusive, phenyl, alkoxy with the alkyl group having from one to six carbon atoms, inclusive, hydroxy, nitro, halogen, trifluoromethyl, and ##STR52## wherein Q is selected from OD ##STR53## wherein D is hydrogen, or a pharmaceutically acceptable metal or amine cation wih the proviso that when Q is OD, then D is the same R, M is 2 or 3, R 1 and R 2 are the same or different and are selected from the group consisting of hydrogen, alkyl from one to three carbon atoms, inclusive, and with the additional overall proviso that at least one of X, Y, and Z is not hydrogen when L is hydrogen; L is selected from the group consisting of hydrogen, alkyl of from one to six carbon atoms, inclusive, benzyl, and monosubsubstituted benzyl wherein the substitutent is selected from the group consisting of alkyl from one to four carbon atoms, inclusive, and halogen; the ##STR54## is located at the 3 or 4 position; R is hydrogen, or a pharmaceutically acceptable metal or amine cation.
Claim 2
Dependent Claim
207 words
A compound of the formula ##STR51## wherein W is hydrogen, X, Y, and Z can be the same or different and are selected from the group consisting of hydrogen, alkyl from one to six carbon atoms, inclusive, phenyl, alkoxy with the alkyl group having from one to six carbon atoms, inclusive, hydroxy, nitro, halogen, trifluoromethyl, and ##STR52## wherein Q is selected from OD ##STR53## wherein D is hydrogen, or a pharmaceutically acceptable metal or amine cation wih the proviso that when Q is OD, then D is the same R, M is 2 or 3, R 1 and R 2 are the same or different and are selected from the group consisting of hydrogen, alkyl from one to three carbon atoms, inclusive, and with the additional overall proviso that at least one of X, Y, and Z is not hydrogen when L is hydrogen; L is selected from the group consisting of hydrogen, alkyl of from one to six carbon atoms, inclusive, benzyl, and monosubsubstituted benzyl wherein the substitutent is selected from the group consisting of alkyl from one to four carbon atoms, inclusive, and halogen; the ##STR54## is located at the 3 or 4 position; R is hydrogen, or a pharmaceutically acceptable metal or amine cation.
Claim 3
Dependent Claim
10 words
Compounds in accordance with claim 1 wherein X is hydrogen.
Claim 4
Dependent Claim
12 words
Compounds in accordance with claim 1 wherein X and Y are hydrogen.
Claim 5
Dependent Claim
63 words
Compounds in accordance with claim 1 wherein X, y, and Z are the same or different and are selected from the group consisting of hydrogen, alkyl from one to three carbon atoms, inclusive, alkoxy with the alkyl group having from one to three carbon atoms, inclusive, hydroxy, nitro, halogen, trifluoromethyl, and ##STR55## R is hydrogen or a pharmaceutically acceptable metal or amine cation.
Claim 6
Dependent Claim
10 words
Compounds in accordance with claim 4 wherein X is hydrogen.
Claim 7
Dependent Claim
12 words
Compounds in accordance with claim 4 wherein X and Y are hydrogen.
Claim 8
Dependent Claim
70 words
Compounds in accordance with claim 5 wherein Y and Z are the same or different and are selected from the group consisting of hydrogen, alkyl from one to three carbon atoms, inclusive, alkoxy with the alkyl group having from one to three carbon atoms, inclusive, nitro, fluoro, chloro, trifluoromethyl, and ##STR56## and L is selected from the group consisting of hydrogen and alkyl from one to three carbon atoms, inclusive.
Claim 9
Dependent Claim
12 words
Compounds in accordance with claim 7 wherein W and Y are hydrogen.
Claim 10
Dependent Claim
61 words
Compounds in accordance with claim 7 wherein Y and Z are the same or different and are selected from the group consisting of hydrogen, alkyl of from one to three carbon atoms, alkoxy with alkyl having from one to three carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, ##STR57## L is hydrogen; R is hydrogen, or a pharmaceutically acceptable metal or amine cation.
Claim 11
Dependent Claim
24 words
Compounds in accordance with claim 9 wherein Y and Z are at the 2 and 5 position and ##STR58## is at the 3 position.
Claim 12
Dependent Claim
19 words
Compounds in accordance with claim 10 wherein X and Y are hydrogen and Z is at the 5 position.
Claim 13
Dependent Claim
6 words
N,N'-(5-carboxy-m-phenylene)dioxamic acid according to claim 1.
Claim 14
Dependent Claim
6 words
N,N'-(2-chloro-m-phenylene)dioxamic acid according to claim 1.
Claim 15
Dependent Claim
15 words
Compounds in accordance with claim 10 wherein Y is hydrogen and Z is 5 carbamoyl.
Claim 16
Dependent Claim
11 words
(5-Carbamoyl-m-phenylene)dioxamic acid hydrate and its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
Claim 17
Dependent Claim
14 words
Compounds in accordance with claim 10 wherein Y is 2-chloro and Z is 5-trifluoromethyl.
Claim 18
Dependent Claim
10 words
N,N'-[2-Chloro-5-(trifluoromethyl)-m-phenylene]dioxamic acid and its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
Claim 19
Dependent Claim
21 words
Compounds in accordance with claim 9 wherein Y is 4-chloro and Z is 6-chloro and ##STR59## is at the 3 position.
Claim 20
Dependent Claim
10 words
N,N'-(4,6-Dichloro-m-phenylene)dioxamic acid and its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
Claim 21
Dependent Claim
14 words
Compounds in accordance with claim 10 wherein Y is 2-methyl and Z is 5-carboxy.
Claim 22
Dependent Claim
10 words
N,N'-(5-Carboxy-2-methylphenylene-1,3-)dioxamic acid and its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
Claim 23
Dependent Claim
14 words
Compounds in accordance with claim 10 wherein Y is 2-chloro and Z is 5-carboxy.
Claim 24
Dependent Claim
10 words
N,N'-(5-Carboxy-2-chlorophenylene-1,3-)dioxamic acid and its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
Claim 25
Dependent Claim
20 words
Compounds in accordance with claim 9 wherein ##STR60## is at the 3 position, Y is hydrogen and Z is 2-carboxy.
Claim 26
Dependent Claim
10 words
N,N'-(2-Carboxyphenylene-1,3-)dioxamic acid and its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
Claim 27
Dependent Claim
10 words
Compounds in accordance with claim 11 wherein Z is methoxy.
Claim 28
Dependent Claim
10 words
N,N'-(5-Methoxyphenylene-1,3-)dioxamic acid are its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
Claim 29
Dependent Claim
14 words
Compounds in accordance with claim 10 wherein Y is 2-chloro and Z is 5-methyl.
Claim 30
Dependent Claim
10 words
N,N'-(2-Chloro-5-methylphenylene-1,3-)dioxamic acid and its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
Claim 31
Dependent Claim
20 words
Compounds in accordance with claim 9 wherein ##STR61## is at the 3 position, Y is hydrogen, and Z is 4-butyl.
Claim 32
Dependent Claim
10 words
4-Butyl-N,N'-(m-phenylene)dioxamic acid and its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
Claim 33
Dependent Claim
20 words
Compounds in accordance with claim 9 wherein ##STR62## is at the 3 position, Y is hydrogen, and Z is 4:methoxy.
Claim 34
Dependent Claim
10 words
4-Methoxy-N,N'-(m-phenylene)dioxamic acid and its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
Claim 35
Dependent Claim
48 words
Compounds of the formula ##STR63## wherein R is hydrogen, or a pharmaceutically acceptable metal or amine cation; Z is selected from the group consisting of hydrogen, alkyl of from one to three carbon atoms, inclusive, alkoxy of from one to three carbon atoms, inclusive, fluoro, chloro, and bromo.
Claim 36
Dependent Claim
48 words
Compounds of the formula ##STR63## wherein R is hydrogen, or a pharmaceutically acceptable metal or amine cation; Z is selected from the group consisting of hydrogen, alkyl of from one to three carbon atoms, inclusive, alkoxy of from one to three carbon atoms, inclusive, fluoro, chloro, and bromo.
Claim 37
Dependent Claim
10 words
N,N'-(5-Acetyl-2-chloro-m-phenylene)dioxamic acid and its di-tris(hydroxymethyl)aminomethane salt according to claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-06-25 | 1982-12-25 | 1983-06-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-06-25 | 1986-12-25 | 1987-06-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-06-25 | 1990-12-25 | 1991-06-26 | $7700.00 | Window Closed / Lapsed |