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US 4,556,654 AGranted
Antimicrobial substituted anthra[1,9-cd]pyrazol-6(2H)-ones
AssigneeWarner-Lambert Company
InventorsHoward D. H. Showalter, Judith L. Johnson, Leslie M. Werbel, Edward F. Elslager
Life of this patent
Estimating the term…
Abstract
Substituted anthra[1,9-cd]pyrazol-6(2H-ones have antimicrobial activity. Methods for their preparation, use and pharmaceutical compositions are disclosed.
Claims26
A compound having the structural formula ##STR60## wherein X, X', and W may be the same or different and are H, OH, alkoxy of one to four carbon atoms or chlorine;
- R is H or alkyl of from one to six carbon atoms;
- Y is H, alkyl of from one to six carbon atoms which may be substituted with an OR.sub.1 group wherein R.sub.1 is H or alkyl of from one to six carbon atoms, or ANR.sub.2 R.sub.3 wherein A is straight or branched alkylene of from two to eight carbon atoms, R.sub.2 and R.sub.3 may be the same or different and are H, alkyl of from one to six carbon atoms which may be substituted with OH or an NRaRa wherein Ra may be the same or different and is H or alkyl of from one to three carbon atoms which may be substituted with OH, or NR.sub.b R.sub.b wherein R.sub.b is the same or different and is H or alkyl of from one to three carbon atoms, or R.sub.2 and R.sub.3 when taken together may form ##STR61## wherein n and m may be the same or different and are one, two, or three provided that the sum of n and m is such as to form a five or six-membered ring and B is a direct bond, O, S, or N-R.sub.4 wherein R.sub.4 is H or alkyl of from one to six carbon atoms;
- R and Y when taken together may form ##STR62## wherein n, m, and B are defined above;
- Z is alkyl of from one to six carbon atoms substituted with an N(R.sub.1).sub.2, SR.sub.1, or OR.sub.1 group wherein R.sub.1 is the same or different and is defined above, or DNR.sub.2 R.sub.3 wherein D is straight or branched alkylene of from two to eight carbon atoms which may be substituted with an OH group and R.sub.2 and R.sub.3 are as defined above;
- or a pharmaceutically acceptable salt thereof.
2 more elements
A compound having the structural formula ##STR63## wherein X, X', and W may be the same or different and are H or OH, alkoxy of one to four carbon atoms or chlorine;
- R is H or alkyl of from one to six carbon atoms;
- Y is H, alkyl of from one to six carbon atoms which may be substituted with an OR.sub.1 group wherein R.sub.1 is H or alkyl of from one to six carbon atoms, or ANR.sub.2 R.sub.3 wherein A is straight or branched alkylene of from two to eight carbon atoms, R.sub.2 and R.sub.3 may be the same or different and are H, alkyl of from one to six carbon atoms which may be substituted with OH or an NRaRa wherein Ra may be the same or different is H or alkyl of from one to three carbon atoms which may be substituted with OH, or NR.sub.b R.sub.b wherein R.sub.b is the same or different and is H or alkyl of from one to three carbon atoms, or R.sub.2 and R.sub.3 when taken together may form ##STR64## wherein n and m may be the same or different and are one, two, or three provided that the sum of n and m is such as to form a five- or six-membered ring and B is a direct bond, O, S, or N-R.sub.4 wherein R.sub.4 is H or alkyl of from one to six carbon atoms;
- R and Y when taken together may form ##STR65## wherein n, m, and B are defined above;
- Z is alkyl of from one to six carbon atoms substituted with an N(R.sub.1).sub.2, SR.sub.1, or OR.sub.1 group wherein R.sub.1 is the same or different and is as defined above, or DNR.sub.2 R.sub.3 wherein D is straight or branched alkylene of from two to eight carbon atoms which may be substituted with an OH group and R.sub.2 and R.sub.3 are as defined above;
- or a pharmaceutically acceptable salt thereof.
2 more elements
A compound having the structural formula ##STR66## wherein X and X' may be the same or different and are H, OH, alkoxy of one to four carbon atoms or chlorine;
- R is H or alkyl of from one to six carbon atoms;
- Y is H, alkyl of from one to six carbon atoms which may be substituted with an OR.sub.1 group wherein R.sub.1 is H or alkyl of from one to six carbon atoms, or ANR.sub.2 R.sub.3 wherein A is straight or branched alkylene of from two to eight carbon atoms, R.sub.2 and R.sub.3 may be the same or different and are H, alkyl of from one to six carbon atoms which may be substituted with OH or an NRaRa wherein Ra may be the same or different is H or alkyl of from one to three carbon atoms which may be substituted with OH, or NR.sub.b R.sub.b wherein R.sub.b is the same or different and is H or alkyl of from one to three carbon atoms, or R.sub.2 and R.sub.3 when taken together may form ##STR67## wherein n and m may be the same or different and are one, two, or three provided that the sum of n and m is such as to form a five- or six-membered ring and B is a direct bond, O, S, or N-R.sub.4 wherein R.sub.4 is H or alkyl of from one to six carbon atoms;
- R and Y when taken together may form ##STR68## wherein n, m, and B are defined above;
- Z is alkyl of from one to six carbon atoms substituted with an N(R.sub.1).sub.2, SR.sub.1, or OR.sub.1 group wherein R.sub.1 is the same or different and is as defined above, or DNR.sub.2 R.sub.3 wherein D is straight or branched alkylene of from two to eight carbon atoms which may be substituted with an OH group and R.sub.2 and R.sub.3 are as defined above;
- or a pharmaceutically acceptable salt thereof.
2 more elements
A compound having the structural Formula I ##STR69## wherein X and X' may be the same or different and are H or OH;
- R is H or alkyl of from one to six carbon atoms;
- Y is H, alkyl of from one to six carbon atoms which may be substituted with an OR.sub.1 group wherein R.sub.1 is H or alkyl of from one to six carbon atoms, or ANR.sub.2 R.sub.3 wherein A is straight or branched alkylene of from two to eight carbon atoms, R.sub.2 and R.sub.3 may be the same or different and are H, alkyl of from one to six carbon atoms which may be substituted with OH or an NRaRa wherein Ra may be the same or different is H or alkyl of from one to three carbon atoms which may be substituted with OH, or NR.sub.b R.sub.b wherein R.sub.b is the same or different and is H or alkyl of from one to three carbon atoms, or R.sub.2 and R.sub.3 when taken together may form ##STR70## wherein n and m may be the same or different and are one, two, or three provided that the sum of n and m is such as to form a five- or six-membered ring and B is a direct bond, O, S, or N-R.sub.4 wherein R.sub.4 is H or alkyl of from one to six carbon atoms;
- R and Y when taken together may form ##STR71## wherein n, m, and B are defined above;
- Z is alkyl of from one to six carbon atoms substituted with an N(R.sub.1).sub.2, SR.sub.1, or OR.sub.1 group wherein R.sub.1 is the same or different and is as defined above, or DNR.sub.2 R.sub.3 wherein D is straight or branched alkylene of from two to eight carbon atoms which may be substituted with an OH group and R.sub.2 and R.sub.3 are as defined above;
- or a pharmaceutically acceptable salt thereof.
2 more elements
A compound having the structural Formula I' ##STR72## wherein R' is H or alkyl of from 1 to 6 carbon atoms;
- Y' is CH.sub.2 CH.sub.2 NHCH.sub.2 CH.sub.2 OH when Z' is alkyl of from one to four carbon atoms which may be substituted with an SR.sub.1 ', or OR.sub.1 ' group wherein R.sub.1 ' is H or alkyl of from one to four carbon atoms or D'NR.sub.2 'R.sub.3 ' wherein D' is straight or branched alkylene of from two to four carbon atoms which may be substituted with an OH group and R.sub.2 ' and R.sub.3 ' may be the same or different and are H, alkyl of from one to six carbon atoms which may be substituted with an OH or R.sub.2 ' and R.sub.3 ' when taken together may form ##STR73## wherein n' and m' may be the same or different and are one or two provided that the sum of n' and m' is such as to form a five- or six-membered ring, and B' is a direct bond, O, S, or N-R.sub.4 ' wherein R.sub.4 ' is H or alkyl of from one to four carbon atoms;
- or Z' is CH.sub.2 CH.sub.2 NHCH.sub.2 CH.sub.2 OH when Y' is H, alkyl of from one to six carbon atoms which may be substituted with an OR.sub.1 ' group wherein R.sub.1 ' is defined above or A'NR.sub.1 'R.sub.2 ' wherein A' is alkylene of from two to four carbon atoms and R.sub.1 ' and R.sub.2 ' are as defined above;
- or a pharmaceutically acceptable salt thereof.
A compound having structural Formula I" ##STR74## wherein R" is H or alkyl of from one to six carbon atoms;
- Y" is H, alkyl of from one to six carbon atoms which may be substituted with an OR.sub.1 " group wherein R.sub.1 " is H or alkyl of from one to four carbon atoms, or A"NR.sub.2 "R.sub.3 " wherein A" is alkylene of from two to four carbon atoms, R.sub.2 " and R.sub.3 " may be the same or different and are H, alkyl of from one to six carbon atoms which may be substituted with an OH or an NRa"Ra" wherein Ra" may be the same or different and is H or alkyl of from one to three carbon atoms which may be substituted with an OH or R.sub.2 " and R.sub.3 " when taken together may form ##STR75## wherein n" and m" may be the same or different and are one or two provided that the sum of n" and m" is such as to form a five- or six-membered ring, and B" is a direct bond, O, S, or N-R.sub.4 " wherein R.sub.4 " is H or alkyl of from one to four carbon atoms;
- Z" is alkyl of from one to four carbon atoms which may be substituted with an SR.sub.1 ", or OR.sub.1 " group wherein R.sub.1 " is defined above, or D"NR.sub.2 "R.sub.3 " wherein D" is alkylene of from two to four carbon atoms which may be substituted with an OH group and R.sub.2 " and R.sub.3 " are as defined above;
- or a pharmaceutically acceptable salt thereof.
A compound having structural Formula I"' ##STR76## wherein R"' is H or alkyl of from one to six carbon atoms;
- Y"' is H, alkyl of from one to six carbon atoms which may be substituted with an OR.sub.1 "' group wherein R.sub.1 "' is H or alkyl of from one to four carbon atoms, or A"'NR.sub.2 "'R.sub.3 "' wherein A"' is alkylene of from two to four carbon atoms, R.sub.2 "' and R.sub.3 "' may be the same or different and are H, alkyl of from one to six carbon atoms which may be substituted with an OH or an NRa"'Ra"' wherein Ra"' may be the same or different and is H or alkyl of from one to three carbon atoms which may be substituted with an OH or R.sub.2 "' and R.sub.3 "' when taken together may form ##STR77## wherein n"' and m"' may be the same or different and are one or two provided that the sum of n"' and m"' is such as to form a five- or six-membered ring and B"' is a direct bond, O, S, or N-R.sub.4 "' wherein R.sub.4 "' is H or alkyl of from one to four carbon atoms;
- Z"' is alkyl of from one to four carbon atoms which may be substituted with an SR.sub.1 "', or OR.sub.1 "' group wherein R.sub.1 "' is defined above, or D"'NR.sub.2 "'R.sub.3 "' wherein D"' is alkylene of from two to four carbon atoms which may be substituted with an OH group and R.sub.2 "' and R.sub.3 "' are as defined above;
- or a pharmaceutically acceptable salt thereof.
A compound having a structural Formula I"" ##STR78## wherein R"" is H or alkyl of from one to six carbon atoms;
- Y"" is H, alkyl of from one to six carbon atoms which may be substituted with an OR.sub.1 "" group wherein R.sub.1 "" is H or alkyl of from one to four carbon atoms, or A""NR.sub.2 ""R.sub.3 "" wherein A"" is alkylene of from two to four carbon atoms, R.sub.2 "" and R.sub.3 "" may be the same or different and are H, alkyl of from one to six carbon atoms which may be substituted with an OH or an NRa""Ra"" wherein Ra"" may be the same or different and is H or alkyl of from one to three carbon atoms which may be substituted with an OH or R.sub.2 "" and R.sub.3 "" when taken together may form ##STR79## wherein n"" and m"" may be the same or different and are one or two provided that the sum of n"" and m"" is such as to form a five- or six-membered ring, and B"" is a direct bond, O, S, or N-R.sub.4 "" wherein R.sub.4 "" is H or alkyl of from one to four carbon atoms;
- Z"" is alkyl of from one to four carbon atoms which may be substituted with an SR.sub.1 "", or OR.sub.1 "" group wherein R.sub.1 "" is defined above, or D""NR.sub.2 ""R.sub.3 "" wherein D"" is alkylene of from two to four carbon atoms which may be substituted with an OH group and R.sub.2 "" and R.sub.3 "" are as defined above;
- or a pharmaceutically acceptable salt thereof.
A compound having the structural Formula IV ##STR86## wherein R is H or alkyl of from one to six carbon atoms;
- Y is alkyl of from one to six carbon atoms substituted with an OR.sub.1 group wherein R.sub.1 is H or alkyl of from one to six carbon atoms, or ANR.sub.2 R.sub.3 wherein A is alkylene of from two to eight carbon atoms, R.sub.2 and R.sub.3 may be the same or different and are H, alkyl of from one to six carbon atoms which may be substituted with OH or an NRaRa wherein Ra may be the same or different and is H or alkyl of from one to three carbon atoms which may be substituted with OH, or R.sub.2 and R.sub.3 when taken together may form ##STR87## wherein n and m may be the same or different and are one, two, or three, provided that the sum of n and m is such as to form a five- or six-membered ring, and B is a direct bond, O, S, or N-R.sub.4 wherein R.sub.4 is H or alkyl of from one to six carbon atoms;
- R and Y when taken together may form ##STR88## wherein n, m, and B are defined above;
- Z is alkyl of from one to six carbon atoms substituted with an N(R.sub.1).sub.2, SR.sub.1, or OR.sub.1 group wherein R.sub.1 may be the same or different and is defined above, or DNR.sub.2 R.sub.3 wherein D is alkylene of from two to eight carbon atoms which may be substituted with an OH group and R.sub.2 and R.sub.3 are as defined above;
- or a pharmaceutically acceptable salt thereof.
1 more element
A compound having the structural Formula VII ##STR89## wherein Z is alkyl of from one to six carbon atoms substituted with an N(R.sub.1).sub.2 or SR.sub.1 wherein R.sub.1 may be the same or different and is H or alkyl of from one to six carbon atoms, or DNR.sub.2 R.sub.3 wherein D is alkylene of from two to eight carbon atoms which may be substituted with an OH group and R.sub.2 and R.sub.3 may be the same of different and are H, alkyl of from one to six carbon atoms which may be substituted with OH or an NRaRa wherein Ra may be the same or different and is H or alkyl of from one to three carbon atoms which may be substituted with OH, or R.sub.2 and R.sub.3 when taken together may form ##STR90## wherein n and m may be the same or different and are one, two, or three, provided that the sum of n and m is such as to form a five- or six-membered ring, and B is a direct bond, O, S, or N-R.sub.4 wherein R.sub.4 is H or alkyl of from one to six carbon atoms.
Dependencies are inferred from the claim text.