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US3993679A Expired / Lapsed US ⏱️ 0.0 years remaining

Cyano phenylene dioxamic molecules

Assignee: Pharmacia and Upjohn Co
•
Filing: 1973-07-26
•
Granted: 1976-11-23
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Expires: 1993-07-26
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Abstract

Abstract Compounds represented below ##SPC1## 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 2026-11-04 10:23
CPC Classifications
C; C07; C07C; C07C233/00; A; A61; A61P; A61P37/00; A61P37/08

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 306 words
A compound of the formula ##SPC4## wherein W, X, and Y 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 ##EQU1## wherein Q is selected from ##EQU2## and ##EQU3## wherein D is selected from the group consisting of hydrogen, alkyl from one to six carbon atoms, inclusive, phenyl, ##EQU4## and a pharmaceutically acceptable metal or amine cation with the proviso that where R is alkyl from one to six carbon atoms, inclusive, or phenyl, and Q is OD, then D is alkyl from one to six carbon atoms, inclusive, hydrogen, ##EQU5## or phenyl, and when R is ##EQU6## and Q is OD, then D is the same as R and with the further proviso that when R is hydrogen or a pharmaceutically acceptable metal or amine cation and Q is OD, then D is the same as 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 L is selected from the group consisting of hydrogen, alkyl of from one to six carbon atoms, inclusive, benzyl, and monosubstituted benzyl wherein the substituent is selected from the group consisting of alkyl from one to four carbon atoms, inclusive, and halogen; R is selected from the group consisting of hydrogen, alkyl from one to six carbon atoms, inclusive, phenyl, a pharmaceutically acceptable metal or amine cation, and ##EQU7## where n is 2 or 3, R 3 and R 4 are the same or different and are selected from the group consisting of hydrogen, alkyl of one to three carbon atoms, inclusive.
Claim 2
Dependent Claim 306 words
A compound of the formula ##SPC4## wherein W, X, and Y 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 ##EQU1## wherein Q is selected from ##EQU2## and ##EQU3## wherein D is selected from the group consisting of hydrogen, alkyl from one to six carbon atoms, inclusive, phenyl, ##EQU4## and a pharmaceutically acceptable metal or amine cation with the proviso that where R is alkyl from one to six carbon atoms, inclusive, or phenyl, and Q is OD, then D is alkyl from one to six carbon atoms, inclusive, hydrogen, ##EQU5## or phenyl, and when R is ##EQU6## and Q is OD, then D is the same as R and with the further proviso that when R is hydrogen or a pharmaceutically acceptable metal or amine cation and Q is OD, then D is the same as 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 L is selected from the group consisting of hydrogen, alkyl of from one to six carbon atoms, inclusive, benzyl, and monosubstituted benzyl wherein the substituent is selected from the group consisting of alkyl from one to four carbon atoms, inclusive, and halogen; R is selected from the group consisting of hydrogen, alkyl from one to six carbon atoms, inclusive, phenyl, a pharmaceutically acceptable metal or amine cation, and ##EQU7## where n is 2 or 3, R 3 and R 4 are the same or different and are selected from the group consisting of hydrogen, alkyl of one to three carbon atoms, inclusive.
Claim 3
Dependent Claim 11 words
A compound in accordance with claim 1 wherein W is hydrogen.
Claim 4
Dependent Claim 13 words
A compound in accordance with claim 1 wherein W and X are hydrogen.
Claim 5
Dependent Claim 14 words
A compound in accordance with claim 1 wherein W, X and Y are hydrogen.
Claim 6
Dependent Claim 98 words
A compound in accordance with claim 2 wherein X and Y 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 ##STR52## provided that when Q is OD, and D is alkyl, the upper limitation of carbon atoms for alkyl is three; R is selected from the group consisting of hydrogen, alkyl from one to three carbon atoms, inclusive, phenyl, and a pharmaceutically acceptable metal or amine cation.
Claim 7
Dependent Claim 13 words
A compound in accordance with claim 5 wherein W and X are hydrogen.
Claim 8
Dependent Claim 14 words
A compound in accordance with claim 6 wherein W, X, and Y are hydrogen.
Claim 9
Dependent Claim 63 words
A compound in accordance with claim 6 wherein Y is 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 ##STR53## and L is selected from the group consisting of hydrogen and alkyl from one to three carbon atoms, inclusive.
Claim 10
Dependent Claim 14 words
A compound in accordance with claim 8 wherein W, X, and Y are hydrogen.
Claim 11
Dependent Claim 142 words
A compound in accordance with claim 8 wherein Y is 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 and ##STR54## wherein D is selected from the group consisting of hydrogen, alkyl from one to three carbon atoms, inclusive, and a pharmaceutically acceptable metal or amine cation with the proviso that where R is alkyl from one to three carbon atoms, inclusive, D is alkyl from one to three carbon atoms, inclusive, or hydrogen, and when R is hydrogen or a pharmaceutically accepable metal or amine cation, then D is the same as R; L is hydrogen; R is selected from the group consisting of hydrogen, alkyl from one to three carbon atoms, inclusive, and a pharmaceutically acceptable metal or amine cation.
Claim 12
Dependent Claim 13 words
A compound in accordance with claim 10 wherein Y is at the 2-position.
Claim 13
Dependent Claim 19 words
A compound in accordance with claim 11 wherein D is hydrogen or a pharmaceutically acceptable metal or amine cation.
Claim 14
Dependent Claim 6 words
N,N'-(5-cyano-m-phenylene)dioxamic acid according to claim 1.
Claim 15
Dependent Claim 11 words
A compound in accordance with claim 10 wherein Y is 4-chloro.
Claim 16
Dependent Claim 10 words
N,N'-(4-chloro-5-cyano-m-phenylene)dioxamic acid and its di-tris-(hydroxymethyl)aminomethane salt according to claim 1.
Claim 17
Dependent Claim 11 words
A compound in accordance with claim 11 wherein Y is 2-chloro.
Claim 18
Dependent Claim 10 words
N,N'-(2-Chloro-5-cyano-m-phenylene)dioxamic acid and its di-tris-(hydroxymethyl)aminomethane salt according to claim 1.
Claim 19
Dependent Claim 18 words
A compound in accordance with claim 1 wherein W, X, and L are hydrogen and Y is 2-chloro.
Claim 20
Dependent Claim 15 words
A compound in accordance with claim 1 wherein W, X, Y and L are hydrogen.
Claim 21
Dependent Claim 18 words
A compound in accordance with claim 1 wherein W, X, and L are hydrogen and Y is 4-chloro.
Claim 22
Dependent Claim 6 words
Diethyl N,N'-(2-chloro-5-cyano-m-phenylene)dioxamate according to claim 18.
Claim 23
Dependent Claim 6 words
Di-tris(hydroxymethyl)methylammonium N,N'-(2-chloro-5-cyano-m-phenylene)dioxamate according to claim 17.

References Cited (Backward Citations)

US3511804A Cited
US3532737A Cited
US3639249A Cited
US3781329A Cited
US3852324A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-11-23 1980-05-24 1980-11-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-11-23 1984-05-24 1984-11-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-11-23 1988-05-24 1988-11-23 $7700.00 Window Closed / Lapsed

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