- Olprinone hydrochloride compound preparation method
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The invention discloses an olprinone hydrochloride compound preparation method. 6-bromoimidazo[1,2-a]pyridine is used as a starting material to prepare an olprinone hydrochloride compound through Grignard reaction, ozone oxidation, additive reaction, closed-loop reaction, salification and refining. The preparation process is mild in reaction condition, technically stable, high in repeatability andproduct yield, less in impurity and suitable for industrial production.
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- Preparation method of olprinone and 9-azaindole-5-boric acid
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The invention relates to a preparation method of olprinone and 9-azaindole-5-boric acid, in particular to a method for preparing olprinone via Suzuki coupling. In the preparation method of olprinone and 9-azaindole-5-boric acid, a converging synthetic route is innovatively designed, has high atom utilization rate as compared with existing three series synthetic processes and is better than existing synthetic routes in overall reaction yield; the preparation method has mild synthetic reaction conditions, is simple to perform and is easy to industrialize; the prepared olprinone may be further olprinone hydrochloride via salifying, and the prepared olprinone hydrochloride has the advantages such as low impurity content, high purity, high yield and good mildness of reaction conditions.
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- Imidazo[1,2-a]pyridines. Synthesis and inotropic activity of new 5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinone derivatives
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A series of 1,2-dihydro-5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinones was synthesized and evaluated for positive inotropic activity. 1,2-Dihydro-5-imidazo[1,2-a]pyridin-6-yl-6-methyl-2-oxo-3- pyridinecarbonitrile (11a) hydrochloride monohydrate (E-1020) was found to be a potent and selective inhibitor of phosphodiesterase III and a long-acting, potent, orally active positive inotropic agent. Additional imidazo[1,2-a]pyridin-2-yl (3a), -3-yl (16), -7-yl (20) and -8-yl (24a) compounds were also prepared. Altering the pyridine substitution from the 2-position to the 6-position produced a 2-fold increase in the i.v. cardiotonic potency (ED50) from 52 to 23 μg/kg, while substitution at the 3-, 7- or 8-position reduced potency. In the 2-positional isomers, introduction of halogen groups enhanced the activity and 3-chloro-1,2-dihydro-5-(6-fluoroimidazo[1,2-a]pyridin-2-yl)-6-methyl-2(1H)- pyridinone (3a) was the most potent (i.v. ED50 11 μg/kg) in this seris. E-1020 is presently under development for the treatment of congestive heart failure.
- Yamanaka,Miyake,Suda,Ohhara,Ogawa
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p. 1556 - 1567
(2007/10/02)
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- 3-cyano-5-(6-imidazo[1,2-a]pyridyl)pyridin-2-ols useful as cardiotonics
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5-(6-Imidazo[1,2-a]pyridyl)pyridine derivatives represented by general formula: STR1 wherein X represents hydrogen atom or methyl group; Y represents cyano group, carboxamido group, hydrogen atom, amino group or a halogen atom; Z represents hydrogen atom or a lower alkyl group; W represents hydrogen atom or a lower alkyl group; R1 represents hydrogen atom, a lower alkyl group, phenyl group, a group shown by formula: --CH2 R4 in which R4 is a lower alkoxy group, or a group shown by formula: STR2 in which R5 and R6 are hydrogen atom or a lower alkyl group R2 represents hydrogen atom or a halogen atom; and R3 represents hydrogen atom, a lower alkyl group or a halogen atom; or a tautomer thereof; and pharmacologically acceptable salts thereof are disclosed. The 5-(6-imidazo[1,2-a]pyridyl)pyridine derivatives are effective for treating congestive heart failures.
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