Substituted N-heteroaryl-1,2-diaminocyclobutene-3,4-dione compou

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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514341, 514352, 544331, 544332, 546312, 5462727, 546310, 546307, 546308, 546309, 546287, 546289, 546291, 546293, 546294, 546297, C07D21302, C07D23924, A61K 3144, A61K 31505

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055322450

ABSTRACT:
The compounds of the formula: ##STR1## wherein R.sub.1 is hydrogen, straight or branched chain alkyl, cyclic or bicyclic alkyl, alkanoyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; R.sub.2 is hydrogen, straight or branched chain alkyl or cyclic or bicyclic alkyl; A is selected from the following: ##STR2## wherein R.sub.9 is hydrogen, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, mono- or dialkylamino, alkylsulfonamido, alkylcarboxamido, nitro, cyano, carboxyl, chloro, bromo, fluoro or iodo; n is an integer from 0 to 6; R.sub.3 and R.sub.4, independent from each other, are hydrogen, straight or branched chain alkyl, cyclic or bicyclic alkyl, perfluoroalkyl, hydroxyalkyl, alkoxyalkyl, fluoro, or, when taken together, form a spirocyclic ring; R.sub.5 and R.sub.6, independent from each other, are selected from the following: cyano, nitro, amino, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, mono- or dialkylamino, sulfonamide, alkylsulfonamido, arylsulfonamido, alkylcarboxamido, arylcarboxamido, alkylsulfonyl, perfluoroalkylsulfonyl, arylsulfonyl, chloro, bromo, fluoro, iodo, 1-imidazolyl, carboxyl, carboalkoxy, hydroxyl, or hydrogen; and the pharmaceutically acceptable salts thereof relax smooth muscles.

REFERENCES:
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patent: 4673747 (1987-06-01), Nohara et al.
Tietze, et al., Squaric Acid Diethyl Ester: A New Coupling Reagent for the Formation of Drug Biopolymer Conjugates. Synthesis of Squaric Acid Ester Amides and Diamides, Chem. Ber., 124, p. 1215, 1991.
Tietze, et al., Conjugation of p-Aminophenyl Glycosides with Squaric Acid Diester to a Carrier Protein and the Use of Neoglycoprotein in the Histochemical Detection of Lectins, Bioconjugate Chem., 2, p. 148, 1991.
Ehrhardt, et al., Amide und Thioamide der Quadratsaure: Synthese und Reaktionen, Chem. Ber., 110, p. 2506, 1977.
Neuse, et al., Amidierung von Quadratsaure-estern, Liebigs Ann. Chem., p. 619, 1973.

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