3-Aryl 2-oxazolidinones, their process of preparation and their therapeutical application
Patent 4150029 Issued on April 17, 1979. Estimated Expiration Date: 
February 23, 1997. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.
February 23, 1997. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.Patent References 3641036 3655687 Inventors
AssigneeApplicationNo. 05/771814 filed on 02/23/1977US Classes:548/231, 3-position substituent contains ethylenic or acetylenic unsaturation or nitrogen546/209, Ring sulfur or ring oxygen in the additional hetero ring548/232, 4- or 5-position substituent contains chalcogen548/577, Benzene ring bonded directly to the five-membered hetero ring558/418, Nitrogen, except as nitro or nitroso, attached indirectly to the cyano group by nonionic bonding564/305, Benzene ring containing564/384, The aryl ring or ring system and amino nitrogen are bonded directly to the same acyclic carbon, which carbon additionally has only hydrogen or acyclic hydrocarbyl substituents bonded directly thereto564/430, Two benzene rings bonded directly to the same oxygen, sulfur, or polysulfide chain564/440Sulfur attached indirectly to the amino nitrogen by nonionic bondingExaminersPrimary: Rush, Raymond V.Attorney, Agent or FirmInternational ClassesC07D 263/24 (20060101)C07D 263/00 (20060101) Foreign Application Priority Data1976-03-01 FRAbstractCompounds having the formula ##STR1## wherein R1 is hydrogen or CONHR7 and R7 is methyl or isopropyl,And whereinWhen R1 is hydrogen: R is p-nitro, p-cyano; p-aldehydo; p-acetyl; m-ethyl; m-nitro; m-bromo; 3,4-dimethyl; m-NH2 ; p-methylamino; p-dimethylamino; p-diethylamino; p-methylbenzylamino; p-pyrrolidino; p-piperidino; SR4 in para position in which R4 is alkyl having 1 to 4 carbon atoms or cyclohexyl; OR5 is para position in which R5 is alkyl having 2 to 7 carbon atoms, cyclohexyl, cyclohexylmethyl, acetylmethyl; cyanomethyl, alkene-2 yl having 3 to 5 carbon atoms, butene-3 yl, cyclohexene-1 methyl, propargyl, butyne-2 yl, ##STR2## in which n is one or 2 and when n is one, R6 is hydrogen, o-fluoro, o-methyl, m-chloro, m-fluoro, m-methyl, m-trifluoromethyl, p-chloro, p-bromo-, p-fluoro, p-cyano, p-nitro or p-dimethylamino and when n is 2, R6 is hydrogen; and 3-methyl-4-benzyloxy:When R1 is CONHR7 and R7 is methyl: R is m-trifluoromethyl; m-bromo; p-chloro; p-fluoro; 3,4-dichloro; p-thiomethyl; p-acetyl; OR8 in para position wherein R8 is alkyl having 2 to 5 carbon atoms, cyanomethyl, acetylmethyl, propargyl or ##STR3## in which R9 is hydrogen, m-chloro, m-bromo, m-fluoro, p-fluoro, p-chloro or p-nitro;And when R1 is CONHR7 and R7 is isopropyl; R is m-trifluoromethyl or p-benzyloxy.The compounds are prepared by cyclizing 1-phenylamino-2,3-propandiol derivatives to form 5-hydroxymethyl-3 phenyl-2-oxozolidinone derivatives. The 5-hydroxymethyl group can be transformed to --CH2 OCONHR7 by reaction with methyl isocyanate or isopropyl isocyanate. The compounds possess psychotropic, particularly antidepressant, activity.Other References
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