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Dihydropyridazine‑3,5‑dione derivatives

A technology of pyridazine and dihydro, applied in the field of dihydropyridazine-3,5-dione derivatives or their salts or their solvates

Active Publication Date: 2017-12-01
CHUGAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] The development of new hyperphosphatemia treatments that improve these problems of existing phosphorus adsorbents is strongly expected

Method used

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  • Dihydropyridazine‑3,5‑dione derivatives
  • Dihydropyridazine‑3,5‑dione derivatives
  • Dihydropyridazine‑3,5‑dione derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0969] (4aS)-1-[(3-fluorophenyl)methyl]-4-hydroxyl-N-[5-methyl-2-(trifluoromethyl)furan-3-yl]-2-oxo -4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazine-3-carboxamide

[0970] first step

[0971] (S)-1-[(3-Fluoro-benzylidene)-amino]-pyrrolidine-2-carboxylic acid methyl ester

[0972] [chem 29]

[0973]

[0974] L-proline

[0975] Methyl ester hydrochloride (5.00g, 30.2mmol) was suspended in dichloromethane (60.4mL), p-toluenesulfonic acid, monohydrate (6.03g, 31.7mmol) was added, under nitrogen, at room temperature for 10 Stir for minutes. The reaction mixture was concentrated under reduced pressure, added toluene to make it azeotrope, suspended in dichloromethane (60.4 mL), added sodium nitrite (2.19 g, 31.7 mmol), and stirred at room temperature for 2 hours under a nitrogen atmosphere. After filtering the reaction mixture, it was concentrated under reduced pressure to obtain a crude product of (S)-1-nitroso-pyrrolidine-2-carboxylic acid methyl ester. The obtained crude prod...

Embodiment 2

[0993] (4aR)-1-[(3-fluorophenyl)methyl]-4-hydroxyl-N-[5-methyl-2-(trifluoromethyl)furan-3-yl]-2-oxo -4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazine-3-carboxamide

[0994] In the same manner as in the first to third steps of Example 1, the compounds shown in the table below were synthesized from D-proline methyl ester hydrochloride and 3-fluoro-benzaldehyde.

[0995] [Table 2]

[0996]

Embodiment 3

[0998] (4aS)-1-[(3-fluorophenyl)methyl]-4-hydroxy-6,6-dimethyl-N-[5-methyl-2-(trifluoromethyl)furan-3- Base]-2-oxo-5,7-dihydro-4aH-pyrrolo[1,2-b]pyridazine-3-carboxamide

[0999] first step

[1000] (S)-4,4-Dimethyl-pyrrolidine-2-carboxylic acid ethyl ester hydrochloride

[1001] [chem 32]

[1002]

[1003] To (S)-4,4-dimethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (500mg, 1.84mmol) added hydrogen chloride in 1,4-diox An alkane solution (4M, 5.00 mL) was stirred at room temperature for 1 hour under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure, and toluene was added to make it azeotrope to obtain a crude product of the title compound.

[1004] second step

[1005] In the same manner as in the first to third steps of Example 1, the obtained (S)-4,4-dimethyl-pyrrolidine-2-carboxylic acid ethyl ester hydrochloride and 3-fluoro-benzaldehyde Synthesize the following compounds.

[1006] [table 3]

[1007] ...

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Abstract

The present invention provides a medicine, a pharmaceutical composition and a sodium-dependent phosphorus transporter inhibitor containing a dihydropyridazine-3,5-dione derivative or the salt or a solvate thereof, and the compound as an active ingredient , hyperphosphatemia, secondary hyperparathyroidism, prophylactic and / or therapeutic agents for chronic renal failure, and methods of prevention and / or treatment.

Description

technical field [0001] The present invention relates to dihydropyridazine-3,5-dione derivatives or their salts or their solvates. In addition, the present invention relates to medicaments, pharmaceutical compositions, sodium-dependent inhibitors, hyperphosphatemia, secondary A preventive and / or therapeutic agent, and a preventive and / or therapeutic method for episodic hyperparathyroidism and chronic renal failure. Background technique [0002] Phosphorus is present in all cells, is an element accounting for 1% of body weight, and plays an essential role in life support such as cellular energy metabolism. The phosphorus concentration in the blood is determined by bone formation and bone resorption in addition to absorption from the digestive tract and excretion from the kidneys, and is adjusted to a constant concentration. Phosphorus absorption in the digestive tract is mainly performed by NaPi-IIb (SLC34A2), a sodium-dependent phosphate transporter (Non-Patent Documents 1 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D237/04A61K31/50A61K31/501A61K31/5025A61K31/504A61K31/506A61K31/5377A61P3/12A61P13/12A61P43/00C07D401/12C07D401/14C07D403/12C07D471/04C07D487/04C07D487/18
CPCC07D237/04C07D401/12C07D401/14C07D403/12C07D471/04C07D487/04C07D487/18A61P13/12A61P3/12A61P43/00A61P5/18A61K31/50A61K31/501A61K31/5025A61K31/504A61K31/506A61K31/5377
Inventor 大竹义仁冈本直树小野芳幸柏木浩孝金原笃原田武雄堀伸行村田佳久橘一生田中翔太野村研一井出光昭水口荣作市田康弘大友秀一堀场直
Owner CHUGAI PHARMA CO LTD
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