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Deuterated pyridazinone and derivatives and pharmaceutical compositions thereof

A pyridazinone, deuterated technology, applied in the field of deuterated pyridazinone and its derivatives and pharmaceutical compositions, can solve problems such as side effects

Inactive Publication Date: 2020-08-28
SUZHOU ZELGEN BIOPHARML
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Thyroid hormones can regulate body weight and cholesterol levels, but are prone to various side effects, especially on heart and skeletal muscle (Liu Ye, Yi-Lin Li, Karin Mellstrom, Charlotta Mellin, etc., J.Med.Chem.2003,46: 1580- 1588)

Method used

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  • Deuterated pyridazinone and derivatives and pharmaceutical compositions thereof
  • Deuterated pyridazinone and derivatives and pharmaceutical compositions thereof
  • Deuterated pyridazinone and derivatives and pharmaceutical compositions thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Example 1 2-(3,5-dichloro-4-((6-oxo-5-(propan-2-yl-1,1,1,3,3,3-hexadeuterio)-1,6 Preparation of -dihydropyridazin-3-yl)oxy)phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile

[0140]

[0141] The first step: the preparation of 3,6-dichloro-4-(propan-2-yl-1,1,1,3,3,3-hexadeuterio)pyridazine

[0142] 2-(Trideuteriomethyl)-3,3,3-trideuteropropionic acid (1.4 g, 0.0151 mol) was added to 3,6-dichloropyridazine (2.25 g, 0.015 mol) at room temperature Acetonitrile (3.5mL), sulfolane (10.7mL) and water (24.5mL) mixed solution, followed by adding silver nitrate (1.3g, 0.mol). The reaction mixture was heated to 55°C, a solution of concentrated sulfuric acid (2.4mL) in water (7.5mL) was added in one portion, and a solution of ammonium persulfate (5.2g, 0.022mol) in water (7.5mL) was added dropwise within 35 minutes. Reaction The mixture was reacted at 70°C for 20 minutes and then cooled to room temperature and stirred at room temperature for 24 hours. The res...

Embodiment 2

[0157] Example 2 2-(3,5-dichloro-4-((6-oxo-5-(propan-2-yl-heptadeuterio)-1,6-dihydropyridazin-3-yl)oxy) Preparation of phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile

[0158]

[0159] LC-MS: m / z 442 (M+H) + . 1 H NMR (400MHz, DMSO-d 6 )δ13.25(brs,1H),12.23(s,1H),7.79(s,2H),7.44(s,1H).

Embodiment 3

[0160] Example 3 2-(3,5-dichloro-4-((6-oxo-5-(propan-2-yl-2-deutero)-1,6-dihydropyridazin-3-yl)oxy )Phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile

[0161]

[0162] LC-MS: m / z 436 (M+H) + .

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Abstract

The present invention relates to deuterated pyridazinone and derivatives and pharmaceutical compositions thereof. Specifically, the compound has a structure shown as a formula (I), and the definitionsof all groups and substituents are as described in the specification. The compounds have a selective agonistic effect and / or better pharmacodynamic properties on thyroid hormone beta receptors.

Description

technical field [0001] The invention relates to the field of medicine, in particular to deuterated pyridazinone, its derivatives and pharmaceutical composition. Background technique [0002] Thyroid hormones are mainly used to maintain homeostasis in the human body, so they are essential for human growth and development (Paul M. Yen Physiological reviews, 2011, 81(3):1097-1126). Hypothyroidism can cause abnormalities in heart function, weight, metabolism, cholesterol, muscle, and behavior. Thyroid hormones can regulate body weight and cholesterol levels, but are prone to various side effects, especially on heart and skeletal muscle (Liu Ye, Yi-Lin Li, Karin Mellstrom, Charlotta Mellin, etc., J.Med.Chem.2003,46: 1580- 1588). Thyroid hormones in the body mainly through the thyroid hormone receptors to achieve biological activity. Thyroid hormone receptors are divided into two subtypes, α and β, of which thyroid hormone α receptors are mainly related to heart rate control, w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12A61K31/53A61P29/00A61P35/00A61P9/00A61P31/00A61P37/00A61P3/00A61P1/16A61P9/10A61P3/04A61P3/10C07B59/00
CPCC07D403/12A61P29/00A61P35/00A61P9/00A61P31/00A61P37/00A61P3/00A61P1/16A61P9/10A61P3/04A61P3/10C07B59/002C07B2200/05
Inventor 吕彬华崔大为汪祝兵盛泽林
Owner SUZHOU ZELGEN BIOPHARML
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