The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Dec. 18, 1990
Filed:
Nov. 02, 1989
Jacob Szmuszkovicz, Kalamazoo, MI (US);
The Upjohn Company, Kalamazoo, MI (US);
Abstract
A 7-phenylpyrimido[1,2-a][1,4]benzodiazepin-3(5H)-ones of the formula II: ##STR1## wherein R.sub.o is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, --COOR in which R is alkyl defined as above, ##STR2## in which n is a number of 1 to 4, R.sub.6 and R.sub.7 are hydrogen or alkyl defined as above or together ##STR3## is selected from the group consisting of pyrrolidino, piperidino, morpholino, and 4-methylpiperazino, and --CH.sub.2 OH; wherein R.sub.1 is selected from the group consisting of hydrogen, hydroxy, acetoxy, propionoxy, succinyloxy, and alkyl esters thereof; wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are selected from the group consisting of hydrogen, halogen, nitro, cyano, trifluoromethyl, lower-alkyl, -alkoxy, -alkylthio, -alkylsulfinyl, -alkylsulfonyl, -alkanoylamino and -dialkylamino, are synthesized by condensing a 2-amino-5-phenyl-3H-1,4-benzodiazepine of the formula I ##STR4## with a compound selected from the group consisting of acetylenic compounds of the formulae HC.tbd.C--COOR, ROOC.tbd.C--COOR in which R is alkyl defined above, inclusive, and ##STR5## in which R' is alkyl defined as above or ##STR6## defined as above, to give a compound of formula IIa ##STR7## wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 is defined as above, and Ro' is selected from the group consisting of hydrogen, alkyl as defined above, --COOR as defined above, and ##STR8## as defined above. Compounds of formula II wherein R.sub.o is --CH.sub.2 OH are obtained by reducing a compound IIa wherein R.sub.o is --CH.sub.2 OH are obtained by reducing a compound IIa wherein R.sub.o ' is --COOR. The compounds of formula II and their pharmacologically acceptable acid addition salts and N-oxides are useful tranquilizers and sedatives for birds and mammals.