Claims
- 1. A 1,3-diacyl-2-oxindole compound of the formula: ##STR10## and the pharmaceutically-acceptable base salts thereof; wherein X is selected from the group consisting of hydrogen, fluoro, chloro, bromo, alkyl having 1 to 4 carbons, cycloalkyl having 3 to 7 carbons, alkoxy having 1 to 4 carbons, alkylthio having 1 to 4 carbons, trifluoromethyl, alkylsulfinyl having 1 to 4 carbons, alkylsulfonyl having 1 to 4 carbons, nitro, phenyl, alkanoyl having 2 to 4 carbons, benzoyl, thenoyl, alkanamido having 2 to 4 carbons, benzamido and N,N-dialkylsulfamoyl having 1 to 3 carbons in each of said alkyls; and Y is selected from the group consisting of hydrogen, fluoro, chloro, bromo, alkyl having 1 to 4 carbons, cycloalkyl having 3 to 7 carbons, alkoxy having 1 to 4 carbons, alkylthio having 1 to 4 carbons and trifluoromethyl;
- R.sup.1 is --(CH.sub.2).sub.n --Q--R.degree.;
- wherein n is zero, 1 or 2; Q is a divaleent radical derived from a compound selected from the group consisting of oxazole and isoxazole; and R.degree. is hydrogen or alkyl having 1 to 3 carbons;
- and R.sup.2 is alkyl having from 1 to 5 carbons.
- 2. A method of eliciting an analgesic response in a mammalian subject, which comprises administering to said mammalian subject an analgesic response eliciting amount of a 1,3-diacyl-2-oxindole compound of the formula ##STR11## or a pharmaceutically-acceptable base salt thereof; wherein X is selected from the group consisting of hydrogen, fluoro, chloro, bromo, alkyl having 1 to 4 carbons, cycloalkyl having 3 to 7 carbons, alkoxy having 1 to 4 carbons, alkylthio having 1 to 4 carbons, trifluoromethyl, alkylsulfinyl having 1 to 4 carbons, alkylsulfonyl having 1 to 4 carbons, nitro, phenyl, alkanoyl having 2 to 4 carbons, benzoyl, thenoyl, alkanamido having 2 to 4 carbons, benzamido and N,N-dialkylsulfamoyl having 1 to 3 carbons in each of said alkyls; and Y is selected from the group consisting of hydrogen, fluoro, chloro, bromo, alkyl having 1 to 4 carbons, cycloalkyl having 3 to 7 carbons, alkoxy having 1 to 4 carbons and trifluoromethyl;
- R.sup.1 is --(CH.sub.2).sub.n --Q--R.degree.;
- wherein n is zero, 1 or 2; Q is a divalent radical derived from a compound selected from the group consisting of oxazole and isoxizole; and R.degree. is hydrogen or alkyl having 1 to 3 carbons;
- and R.sup.2 is alkyl having from 1 to 5 carbons.
- 3. A method of treating an inflammatory disease in a mammalian subject, which comprises administering to said mammalian subject an inflammatory disease treating amount of a 1,3-diacyl-2-oxindole compound of the formula ##STR12## or a pharmaceutically-acceptable base salt thereof, wherein X is selected from the group consisting of hydrogen, fluoro, chloro, bromo, alkyl having 1 to 4 carbons, cycloalkyl having 3 to 7 carbons, alkoxy having 1 to 4 carbons, alkylthio having 1 to 4 carbons, trifluoromethyl, alkylsulfinyl having 1 to 4 carbons, alkylsulfonyl having 1 to 4 carbons, nitro, phenyl, alkanoyl having 2 to 4 carbons, benzoyl, thenoyl, alkanamido having 2 to 4 carbons, benzamido and N,N-dialkylsulfamoyl having 1 to 3 carbons in each of said alkyls; and Y is selected from the group consisting of hydrogen, fluoro, chloro, bromo, alkyl having 1 to 4 carbons, cycloalkyl having 3 to 7 carbons, alkoxy having 1 to 4 carbons, alkylthio having 1 to 4 carbons and trifluoromethyl;
- R.sup.1 is and --(CH.sub.2).sub.n --Q--R.degree.;
- wherein n is zero, 1 or 2; Q is a divalent radical derived from a compound selected from the group consisting of oxazole and isoxazole; and R.degree. is hydrogen or alkyl having from 1 to 5 carbons;
- and R.sup.2 is alkyl having from 1 to 5 carbons.
- 4. An analgesic or antiinflammatory composition, which comprises a pharmaceutically-acceptable carrier and an effective analgesic or antiinflammatory effective amount of a 1,3-diacyl-2-oxiindole compound according to claim 1 and wherein the weight ratio of the pharmaceutically-acceptable carrier to the 1,3-diacyl-2-oxindole compound is in the range from 1:4 to 4:1.
- 5. The compound according to claim 1, wherein X is 5-chloro, Y is 6-chloro, R.sup.1 is 5-methyl-4-isoxazolyl and R.sup.2 is methyl.
- 6. The compound according to claim 1, wherein X and Y are each hydrogen, R.sup.1 is 3-isoxazolyl and R.sup.2 is methyl.
CROSS-REFERENCE TO RELATED APPLICATION
This application is a division of application Ser. No. 001,261, filed Jan. 7, 1987, now U.S. Pat. No. 4,752,609, which is a division of application Ser. No. 747,194, filed June 20, 1985, now U.S. Pat. No. 4,690,943, which is a continuation-in-part of application Ser. No. 652,372, filed Sept. 19, 1984, now abandoned.
US Referenced Citations (12)
Foreign Referenced Citations (4)
Number |
Date |
Country |
46-114898 |
Apr 1971 |
JPX |
48-14667 |
Feb 1973 |
JPX |
1158532 |
Jul 1969 |
GBX |
1206995 |
Sep 1970 |
GBX |
Non-Patent Literature Citations (8)
Entry |
Pakula et al., Chem. Abstr. 72:12563(k) (1970). |
Brenner et al., Chem. Abstr. 72:12565(n) (1970). |
Shen et al., Chem. Abstr. 72:12566(p) (1970). |
Wenkert et al., J. Amer. Chem. Soc., vol. 80, 4899 (1958). |
Bunnet et al., Org. Syntheses, vol. 40, 1 (1960). |
Bruce, J. Chem. Soc. (London), p. 5302 (1962). |
Tacconi et al., Tetrahedron, vol. 27, p. 561 (1971). |
Kisteneva, Chem. Abstr. 51:5044(a) (1957). |
Divisions (2)
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1261 |
Jan 1987 |
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Parent |
747194 |
Jun 1985 |
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Continuation in Parts (1)
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652372 |
Sep 1984 |
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