1,3-Dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, substituted diamino acetate esters and their acid salts

#This invention relates to the pharmacologically active 1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, substituted diamino acetates. The chemical structure of these compounds may be schematically represented by Formula I: ##STR3## wherein R.sup.1 is selected from the group consisting of (lower)alkyl and ar(lower)alkyl; R.sup.2 is selected from the group consisting of di(lower)alkylamino(lower)alkyl and diar(lower alkylamino(lower)alkyl; R.sup.1 and R.sup.2 may form a radical selected from the group consisting of ##STR4## wherein R.sup.4 is selected from the group consisting of (lower)alkyl, aryl, hydroxy(lower)alkyl, ar(lower)alkyl and (lower)alkoxy(lower)alkyl; R.sup.5 is selected from the group consisting of (lower)alkylamino and piperidino; n is an integer from 3-5; m is an integer from 1-2; r is an integer from 2 to 3; s is an integer from 0-6; t is an integer from 0-6; with the proviso that the sum of s and t must be 3,4,5 or 6; R.sup.3 is selected from the group consisting of hydrogen, (lower)alkyl, ar(lower)alkyl and (lower)alkoxy(lower)alkyl; X is selected from the group consisting of halogen, cyano, trifluoromethyl, nitro and (lower)alkylthio; Y is selected from the group consisting of hydrogen, halogen, trifluoromethyl, nitro and (lower)alkylthio; and the pharmaceutically acceptable salts thereof. The hydrated forms of formula I are also within the scope of the invention, the anhydrous and various hydrated forms of each compound being readily prepared by drying the initially formed product.

#The term (lower)alkyl is used to include straight and branched chain hydrocarbon groups which contain from one to about six carbon atoms such as methyl, ethyl, i-propyl, n-propyl, n-butyl, n-hexyl and the like. The term (lower)alkoxy is used to include hydrocarbonoxy groups which contain from one to about six carbon atoms such as methoxy, ethoxy, n-propoxy, n-butoxy, n-penoxy and the like. The terms halo and halogen are used to include atoms selected from the group consisting of chlorine, fluorine, bromine and iodine. The terms aryl and arare used to include monovalent, aromatic, hydrocarbon radicals containing 6 to 10 carbon atoms such as phenyl, tolyl and naphthyl. The term pharmaceutically acceptable acid addition salts is used to include those non-toxic acid addition salts which may be formed with both organic and inorganic acids such as hydrochloric, hydrobromic, sulfuric, phosphoric, methane sulfonic, nitric, p-toluene sulfonic, acetic, citric, maleic, succinic and the like.

#The compounds of the invention may be prepared by the following reaction scheme: ##STR5## wherein R.sup.1, R.sup.2, R.sup.3, X and Y are the same as hereinabove described and Z is selected from the group consisting of chlorine, bromine and iodine.

#The following examples are added to illustrate but not to necessarily limit the scope of the invention.

#A mixture of 7-chloro-5-(o-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one, 4-oxide (16 g, 0.05 mole) and chloroacetic anhydride (25 g, 0.145 mole) was heated with stirring at 100.degree.-110.degree. for 2.5 hours. Ether was then added and the mixture was stirred for 10 minutes. The solid obtained (14.7 g, 75% yield) was filtered, washed with ether and recrystallized from dichloromethane-ether, mp. 232.degree.-234.degree., nmr (DMSO-D.sub.6) ppm (.delta.); 4.72 (s, 2); 6.10 (s, 1); 7.17 (d, 1); 7.4-8 (m, 6).

#Anal. Calcd for C.sub.17 H.sub.11 Cl.sub.3 N.sub.2 O.sub.3 : C, 51.35; H, 2.79; N, 7.05. Found: C, 51.26; H, 2.83; N, 6.94.