Pyrrolidine derivatives as oxytocin/vasopressin v1a receptors antagonists

Abstract

The present invention relates to a compound of formula (3Z,5S)-5-(hydroxymethyl)-1-[(2′-methyl-1,1′-biphenyl-4-yl)carbonyl]pyrrolidin-3-one O-meth19243yloxime, and/or an active metabolite thereof having antagonist action at the oxytocin receptor and/or vasopressin V1a receptor, to processes for their preparation, pharmaceutical compositions containing them and their use.

1 - 22 . (canceled) 
     
     
         23 . A method of treating a human patient undergoing an embryo transfer procedure, wherein the embryo transfer procedure comprises in vitro fertilization, thereby producing one or more embryos, followed by transfer of the one or more embryos to the uterus of the patient, the method comprising administering to the patient a pharmaceutical composition comprising (i) a compound of formula (3Z,5S)-5-(hydroxymethyl)-1-[(2′-methyl-1,1′-biphenyl-4-yl)carbonyl]pyrrolidin-3-one O-methyloxime and (ii) one or more pharmaceutically acceptable carriers, diluents, or excipients, wherein the purity of the compound relative to one or more other stereoisomers of the compound is at least 85%. 
     
     
         24 . The method of  claim 23 , wherein the purity of the compound relative to one or more other stereoisomers of the compound is at least 90%. 
     
     
         25 . The method of  claim 24 , wherein the purity of the compound relative to one or more other stereoisomers of the compound is at least 95%. 
     
     
         26 . The method of  claim 23 , wherein the purity of the compound relative to one or more other stereoisomers of the compound is from about 90% to about 99.9%. 
     
     
         27 . The method of  claim 26 , wherein the purity of the compound relative to one or more other stereoisomers of the compound is from about 95% to about 99.9%. 
     
     
         28 . A method of treating a human patient undergoing an embryo transfer procedure, wherein the embryo transfer procedure comprises in vitro fertilization, thereby producing one or more embryos, followed by transfer of the one or more embryos to the uterus of the patient, the method comprising administering to the patient a pharmaceutical composition comprising (i) a compound of formula (3Z,5S)-5-(hydroxymethyl)-1-[(2′-methyl-1,1′-biphenyl-4-yl)carbonyl]pyrrolidin-3-one O-methyloxime and (ii) one or more pharmaceutically acceptable carriers, diluents, or excipients, wherein the purity of the compound relative to its stereoisomer, (3E,5S)-5-(hydroxymethyl)-1-[(2′-methyl-1,1′-biphenyl-4-yl)carbonyl]pyrrolidin-3-one O-methyloxime, is at least 85%. 
     
     
         29 . The method of  claim 28 , wherein the purity of the compound relative to (3E,5S)-5-(hydroxymethyl)-1-[(2′-methyl-1,1′-biphenyl-4-yl)carbonyl]pyrrolidin-3-one O-methyloxime is at least 90%. 
     
     
         30 . The method of  claim 29 , wherein the purity of the compound relative to (3E,5S) (hydroxymethyl)-1-[(2′-methyl-1,1′-biphenyl-4-yl)carbonyl]pyrrolidin-3-one O-methyloxime is at least 95%. 
     
     
         31 . The method of  claim 28 , wherein the purity of the compound relative to (3E,5S) (hydroxymethyl)-1-[(2′-methyl-1,1′-biphenyl-4-yl)carbonyl]pyrrolidin-3-one O-methyloxime is from about 90% to about 99.9%. 
     
     
         32 . The method of  claim 31 , wherein the purity of the compound relative to (3E,5S)-5-(hydroxymethyl)-1-[(2′-methyl-1,1′-biphenyl-4-yl)carbonyl]pyrrolidin-3-one O-methyloxime is from about 95% to about 99.9%.