- An efficient synthesis of substituted 1,4-diazepines by a Pd catalyzed amination and sequential hydrogenation condensation
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An efficient synthesis of substituted 1,4-diazepines is developed. The accessible intermediates have been obtained via Pd-catalyzed amination. The subsequent hydrogenation and intramolecular condensation sequences could be conducted successively in one po
- Wang, Xiao-Jian,Tian, Yu-Lin,Zhang, Qing-Yang,Qi, Jian-Guo,Yin, Da-Li
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p. 743 - 746
(2013/07/26)
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- Aryl substituted pyrido[1,4]benzodiazepines and their use as antidepressives
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Novel [2-[(aminopyridinyl)amino]phenyl]arylmethanones and their thioxomethyl, ketal or thioketal analogs of the formula: STR1 wherein; R is selected from the group consisting of hydrogen, loweralkyl, --alk1 --halo, --alk1 --NR1 --NR1 R2 or --alk1 --N=CH--OC2 H5 ; R1 and R2 are selected from the group consisting of hydrogen, loweralkyl, --C(O)O-loweralkyl or R1 and R2 taken together with the adjacent nitrogen atom may form a heterocyclic residue selected from the group consisting of 1-piperidinyl, 1-phthalimido, 1-pyrrolidinyl, 4-morpholinyl, 1-piperazinyl and 4-substituted-1-piperazinyl; B is selected from carbonyl, thioxomethyl, ketal or thioketal; Ar is selected from the group consisting of 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or phenyl substituted by 1 to 3 radicals selected from halo, loweralkyl, loweralkoxy, trifluoromethyl or nitro and may be the same of different; alk1 is a straight or branched hydrocarbon chain containing 1-8 carbon atoms; Z is selected from the group consisting of hydrogen, halogen, loweralkyl, loweralkoxy, hydroxy or nitro; Y is selected from the group consisting of hydrogen or 1-2 radicals selected from loweralkyl, loweralkoxy or hydroxy and may be the same of different, and the acid addition salts thereof. These compounds are intermediates in the preparation of novel aryl substituted pyrido[1,4]benzodiazepines having antidepression activity. Some of these intermediates are useful in treating depression.
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- Aryl substituted pyrido[1,4]benzodiazepines for treatment of depression
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Pyrido[1,4]benzodiazepines having antidepressant activity of the formula STR1 wherein Ar is 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or a substituted phenyl; R is hydrogen, loweralkyl or an amine on the end of a hydrocarbon chain; Z is hydrogen, halogen, trifluoromethyl, loweralkyl, lower-alkoxy, hydroxy or nitro; and Y is hydrogen, loweralkyl, loweralkoxy or hydroxy; and the pharmaceutical salts are prepared from [2-[(aminopyridinyl)amino]phenyl]arylmethanones which also have antidepressant activity.
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- Process and intermediates for the preparation of aryl substituted pyrido[1,4]benzodiazepines
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A process for preparing pyrido[1,4]benzodiazepines having antidepressant activity illustrated by the formula: STR1 wherein Ar is pyridinyl, thienyl or phenyl; R is alkali-metal ion, hydrogen, loweralkyl or an amine or an amine precursor on the end of a hydrocarbon chain and wherein in the process condensation of an amino-chloropyridine with an aryl(aminophenyl)methanone is accomplished with a strong non-nucleophilic base in stirrable admixture with an inert liquid carrier. Alternatively, condensation is accomplished sequentially using titanium tetrachloride first followed by non-nucleophilic base.
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- Aryl substituted pyrido[1,4]benzodiazepines
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Pyrido[1,4]benzodiazepines having antidepressant activity of the formula STR1 wherein Ar is 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or a substituted phenyl; R is hydrogen, loweralkyl or an amine on the end of a hydrocarbon chain; Z is hydrogen, halogen, trifluoromethyl, loweralkyl, loweralkoxy, hydroxy or nitro; and Y is hydrogen, loweralkyl, loweralkoxy or hydroxy; and the pharmaceutical salts are prepared from [2-[(aminopyridinyl)amino]phenyl]arylmethanones which also have antidepressant activity.
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