100450

4,280,957

1

IMIDAZODIAZEPINKS AND PROCESSES THEREFOR

This is a continuation. of application Ser. No. 663,660 filed Mar. 4, 1978 now abandoned which is a CIP of Ser. No. 602,691, filed Aug. 7, 1975, now abandoned which is a CIP of Ser. No. 504,924, filed Sept. 11, 1974,

now abandoned.

DESCRIPTION OF THE INVENT!ON

This invention relates to the pharmacologicaHy ac-tivc imidazo[l,S*a] [l,4Jdia2epine compounds series. The Chemical structure of these compounds may bc depicted by the following formula:

wherein A is

^NC»N^/';

I

R*

Ri is selected from the group consisting of hydrogen, lower alkyl, hydroay lower alkyl, acyloxy Iower alkyj, phenyl, alkoxy lower alkyl. halo lower alkyl, amino lower alkyl, substituted amino lower alkyl, substituted phenyl, pyridyl, aralkyl and the groups

I

RCO

wherein R is hydrogen or lower alkyl; and ROOC wherc R is lower alkyl; Ri is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, amino, cyano. cyano lower alkyl, substituted amino, chloro, bromo or iodo, substituted amino lower alkyl, the group ROOC wherc R is hydrogen or lower alkyl, the grcup

2

(where R, R’ are individually hydrogen, lower alkyl. hydroxy lower alkyl, lower alkcnyl, aryl or together R and R' form a part of a hctcrocyclic ring and the group (CH2)„NRR' where R and R‘ are hydrogen, lower alkyl, hydroxy lower alkyl, lower alkcnyl or together R and R' form a part of a heterocyclic ring and n is 1 to 4); the group

I ^R"

—connC

^R^,J

where R¹⁰, R¹¹, and R^I2arc hydrogen arc hydrogen or lower alkyl and the group (CH^NR^r*⁴ where n is 1 to 4 and R^:3, R¹⁴ arc hydrogen, lower alkyl, hydroxy lower alkyl, lower alkcnyl or R^,3and R¹⁴ together form part of a heterocyclic ring, with the limitalion that where R¹⁰, R^H or R¹² is a basie sidc chain, then the remaining substituents arc hydrogen or lower alkyl; Rj is selected frora the group consisting of hydrogen and lower alkyl; Rj is selected from the group consisting of alkanoyloxy. hydroxy or hydrogen; R4 is selected from the group consisting of hydrogen, halogen, nitro, cyano, trifluoromethyl, lower alkyl. substituted amino, amino, hydroxy lower alkyl and lower alkanoyl; Rt is selected from the group consisting of phenyl, mono-substituted phenyl, di-substituted phenyl, pyridyl and mono-subslituted pyridyl; and

€C

is selected from the group consisting of

OC.TJC ^

wherein X it chłonne broroinc. iodine or hydrogen

T

wherein X n chlo-    wherofl T

fine, brcmine.    » hydrogen

iodine or    or lower

hydrogen    »lkyl

I

RCO

where R is hydrogen or lower alkyl, or derivatives thereof, i.e.. the group

I

R—C=N-R'

wherein R' is hydrogen, lower alkyl, hydroxy, phenyl, alkoxy, amino, mono or di-alkylamino and arylamino and R is hydrogen or lower alkyl, the group

-CON^

R’

and the pharmaccutically acceptable salts thereof.

Various analogous compounds derived from the above compounds, together with various novcl inter-mediates leading to the abovc compounds, are also considcrcd to be within the scopc of the invcntion and exhibit pharmacological activity per se or arc useful intermediates to pharmacologically aclivc compounds.

Analogs of the above compounds which form a part of this invention include compounds of the formula