Pyrrolo[3,2,1-jk][1,4]benzodiazepines and pyrrolo[1,2,3-ef][1,5]benzodiazepines which have central nervous system activity

General Pharmacology and Neuropharmacology of Benzodiazepine Derivatives

“…Because of their high potencies, the quantities of active ingredients in pharmaceutical formulations are very small, and the number of tablets or capsules that would contain sublethal or even lethal doses is simply too great to be swallowed (ADERJAN and MATTERN, 1979). [1] SCHMIlT et al (1967) [2] TAMAGNONE et al (1974) [3] MARCUCCI et al (1971) [4] HESTER et al (1970) [5] BANZIGER (1965) [6] RANDALL et al (1970) [7] SHIBATA et al (1967) …”

“…- TAMAGNONE et al (1974) [2] HESTER et al (1970) [3] BANZIGER (1965) [4] HmLMAN et al (1974) [5] BABBINI et al (1974) [6] SCROLUNI et al (1975) [7] RANDALL and KAPPELL (1973) [15] GILBERT and BENSON (1972) [16] SCHMITT et al (1967) [22] RUDZIK et al (1973) [23] FERNANDEZ-ToME et al (1975) [24] EDANACA et al (1978) [17] OWEN et al (1971) [18] Kwpp and KAHLING (1965) [19] BABBINI et al (1973) [20] BRUNAUD et al (1970) [21] SAKAI et al (1972) [25] KOCH (1979) [26] KAMIOKA et al (1972) 340 [7] [1] RANDALL et al (1960) [2] BERGER et al (1964) [3] ROBICHAUD et al (1970) [4] SHIBATA et al (1967) [5] SAITO et al (1969) [6] USDIN and AMAI (1963) [7] GRUBER et al (1944) [8] REINHARD et al (1952) Oral...…”

Design, Synthesis, and Evaluation of 3,4-Dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-ones as Inhibitors of Poly(ADP-Ribose) Polymerase

“…We initially considered the unsubstituted 3,4-dihydro-2 H -[1,4]diazepino[6,7,1- hi ]indol-1-one 2 to be a versatile intermediate. It was synthesized from 1 using reported procedures . Formylation or iodination via electrophilic aromatic substitution of 2 at C-7 allowed for the preparation of several derivatives as shown in Schemes and .…”

Synthesis, Structure−Activity Relationships, and Pharmacological Profile of 9-Amino-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indoles: Discovery of Potent, Selective Phosphodiesterase Type 4 Inhibitors

“…Ariflo and Rolipram were synthesized as described in the literature. , All the final diazepino derivatives were prepared via elaboration of the key chiral intermediates 8a − f as presented in Scheme , starting from commercially available indolines 1a , b or from 5-methoxyindoline 1c prepared by reduction with sodium cyanoborohydride of the corresponding commercial indole. A procedure for the preparation of the basic benzodiazepine scaffold 7a (R 1 = H) was reported in the literature (general procedures C−F). − The synthesis was modified in order to introduce various substituents on position 9 of the multinucleus intermediates 8b − f . 3-Amino-9-methyl-1-phenyl-6,7-dihydro-3 H -[1,4]diazepino[6,7,1- hi ]indol-4-one ( 7b ) was obtained starting from the commercially available 5-methyl-2,3-dihydro-1 H -indole ( 1b ) and following general procedures C−F.…”