Oxaza heterocycles and pharmaceutical compositions containing same
AssigneeBiofor, Ltd.
InventorSung J. Lee
Life of this patent
Estimating the term…
Abstract
A novel class of 5, 6 or 7 member heterocycles which belong to the 3-isoxazolidinone, 2H-1,2-oxazin-3 (4H)-one and 3-isoxazepinone series of compounds and which are substituted at the 4-carbon by a benzylidene radical. The compounds have utility as analgesic agents, immunomodulating agents, anti-inflammatory agents and anti-pyretic agents and they may be combined with excipients to provide formuations which are useful in treating arthritis and conditions generally associated with that disease.
Claims44
A compound of the formula:
- ##STR14## wherein:
- R is a member selected from the group consisting of hydrogen, alkyl, alkanoyl, aroyl, alkoxyalkyl, alkoxycarbonyl, lower alkylaminocarbonyl and di-lower alkylaminocarbonyl;
- R.sup.0, R.sup.1 and R.sup.2 are the same or different and represent a member selected from the group consisting of hydrogen, lower alkyl, lower alkenyl and lower cycloalkyl:
- X.sup.1 and X.sup.2 are the same or different and represent a member selected from the group consisting of teriaryalkyl, trimethylsilyl and trifluoromethyl;
- and
- n is an integer having a value of 1-3;
- and the nontoxic pharmacologically acceptable salts thereof.
4-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-methyl-3-isoxazolidinone.
The E-isomer of 4-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-methyl-3-isoxazolidinone.
4-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-ethyl-3-isoxazolidinone.
4-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-n-propyl-3-isoxazolidinone
4-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2,5-dimethyl-3-isoxazolidino ne.
4-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-isopropyl-3-isoxazolidinone.
Dihydro-4-(3,5-di-tert-butyl-4-h ydroxybenzylidene)-2-methyl-2H-1,2-oxazin-3(4H)-one.
Dihydro-4-(3,5-di-tert-butyl-4-hydroxybenzyliden e)-2-isopropyl-2H-1,2-oxazin-3(4H)-one.
Tetrahydro-4-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-methyl-3-isoxaz epinone.
A pharmaceutical composition comprising as an active ingredient a compound of the formula:
- ##STR18## wherein:
- R is a member selected from the group consisting of hydrogen, alkyl, alkanoyl, aroyl, alkoxyalkyl, alkoxycarbonyl, lower alkylaminocarbonyl and di-lower alkylaminocarbonyl;
- R.sup.0, R.sup.1 and R.sup.2 are the same or different and represent a member selected from the group consisting of hydrogen, lower alkyl, lower alkenyl and lower cycloalkyl;
- X.sup.1 and X.sup.2 are the same or different and represent a member selected from the group consisting of tertiary-alkyl, trimethylsilyl and trifluoromethyl;
- and
- n is an integer having a value of 1-3;
- or a non-toxic pharmacologically acceptable salt thereof;
- and a pharmaceutically acceptable carrier.
A method for treating inflammation in a mammal which comprises administering a safe and effective amount of a compound having the formula:
- ##STR22## wherein:
- R is a member selected from the group consisting of hydrogen, alkyl, alkanoyl, aroyl, alkoxyalkyl, alkoxycarbonyl, lower alkylaminocarbonyl and di-lower alkylaminocarbonyl;
- R.sup.0, R.sup.1 and R.sup.2 are the same or different and represent a member selected from the group consisting of hydrogen, lower alkyl, lower alkenyl and lower cycloalkyl;
- X.sup.1 and X.sup.2 are the same or different and represent a member selected from the group consisting of tertiaryalkyl, trimethylsilyl and trifluoromethyl;
- and
- n is an integer having a value of 1-3;
- or a non-toxic pharmacologically acceptable salt thereof.
A compound of the formula:
- ##STR26## wherein:
- R is a member selected from the group consisting of hydrogen, alkyl, alkanoyl, aroyl, alkoxyalkyl, alkoxycarbonyl, lower alkylaminocarbonyl and di-lower alkylaminocarbonyl.
- R.sup.0, R.sup.1 and R.sup.2 are the same or different and represent a member selected from the group consisting of hydrogen, lower alkyl, lower alkenyl and lower cycloalkyl;
- X.sup.1 and X.sup.2 are the same or different and represent a member selected from the group consisting of teriaryalkyl, trimethylsilyl and trifluoromethyl;
- and
- n is an integer having a value of 1-3;
- and the nontoxic pharmacologically acceptable salts thereof.
Dependencies are inferred from the claim text.