Sulfonamide compound and application thereof

A compound and drug technology, applied in the field of novel sulfonamide compounds, can solve the problem of the absence of CaSR antagonists

Inactive Publication Date: 2011-05-11
ASAHI KASEI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, an ideal CaSR antagonist must also have excellent safety, no cytotoxicity, mutagenicity, drug interactions, etc., but currently there is no CaSR antagonist recognized as a drug

Method used

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  • Sulfonamide compound and application thereof
  • Sulfonamide compound and application thereof
  • Sulfonamide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0318]Synthesis of (S)-2-bromo-N-methyl N-(oxiran-2-ylmethyl)benzenesulfonamide

[0319] (Step A) Synthesis of 2-bromo-N-methylbenzenesulfonamide

[0320] 2-Bromobenzenesulfonyl chloride (manufactured by Fluorochem, 25 g) was dissolved in tetrahydrofuran (40 mL), and a 40% aqueous methylamine solution (TCI, 25 mL) was added dropwise at 0°C over 10 minutes with stirring. After stirring at room temperature for 2 hours and 40 minutes, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Hexane and a small amount of ethyl acetate were added to the residue, and after stirring, the solid was filtered to obtain the title compound (23.26 g).

[0321] (Step B) Synthesis of (S)-2-bromo-N-methyl N-(oxiran-2-ylmethyl)benzenesulfonamide

[0322] 2-Bromo-N-methylbenzenesulfonamide (10 g) synthesized by Example 1-...

Embodiment 1-2～6

[0324] According to the procedure A and procedure B of Example 1-1, instead of using 2-bromobenzenesulfonyl chloride, 3-bromobenzenesulfonyl chloride (Fluorochem), 4-bromobenzenesulfonyl chloride (TCI), (2-bromophenyl) Methanesulfonyl chloride (MAYB), (3-bromophenyl)methanesulfonyl chloride (MAYB) or (4-bromophenyl)methanesulfonyl chloride (MAYB) to give the title compound. The structures of the compounds of Examples 1-1 to 1-6 are shown below as Exp.1-1 to Exp.1-6, respectively.

[0325]

Embodiment 1-2

[0326] [Example 1-2] (S)-3-bromo-N-methyl-N-(oxirane-2-ylmethyl)benzenesulfonamide

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Abstract

Disclosed is a sulfonamide compound represented by general formula (1) that can be used as an effective component in a CaSR antagonist that is extremely effective in preventing and / or treating bone diseases, such as osteoporosis. Said compound has excellent PTH secretion promoting effects. Said compound is useful as a medically effective component for preventing and / or treating osteoporosis or bone fractures, hypoparathyroidism, or other bone diseases. The general formula (1) is shown in the description.

Description

technical field [0001] The present invention relates to a novel sulfonamide compound. More specifically, it relates to uses of sulfonamide compounds useful as active ingredients of medicines. Background technique [0002] Osteoporosis is defined as "a disease characterized by decreased bone strength and increased risk of fractures". Fractures tend to occur at the ends of the backbone of the extremities and the spine, especially femoral neck fractures, vertebral body compression fractures, distal radius fractures, and proximal arm bone fractures are the four major fractures in osteoporosis. parts. Fractures associated with osteoporosis are difficult to readjust during general treatment due to bone fragility, and there is a problem that it is difficult to obtain sufficient fixation even with osteosynthesis. Moreover, with fractures, the whole body is likely to be disused, and it is easy to cause various serious complications such as decreased muscle strength, joint contract...

Claims

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Application Information

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IPC IPC(8): C07C311/18A61K31/18A61K31/195A61K31/196A61K31/197A61K31/198A61K31/216A61K31/235A61K31/381A61K31/44A61K31/4436A61P5/20A61P17/00A61P17/14A61P19/00A61P19/10C07C311/29C07C311/41C07D213/36C07D213/55C07D213/79C07D213/83C07D333/24C07D333/34C07D409/12
CPCA61P5/20A61P17/00A61P17/14A61P19/00A61P19/10A61P43/00C07C311/13C07C311/18C07C311/29C07C311/41C07C311/46C07C323/32C07C323/52C07C323/67C07D213/36C07D213/55C07D213/79C07D213/83C07D333/24C07D333/34C07D409/12C07C2602/08
Inventor 小川雅巳北川和彦白桥浩光栗林里实
Owner ASAHI KASEI PHARMA
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