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Sulfonamide compound or salt thereof

A technology of compounds and oxygen atoms, applied in the fields of organic chemistry, drug combination, organic active ingredients, etc., can solve the problems of no indication of RNR inhibitory activity and anti-tumor effect, no physiological activity of compounds, etc.

Active Publication Date: 2019-04-02
TAIHO PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, the compounds (4a-e) are intermediates for the production of target 5-benzyl-1,3,4-oxadiazole derivatives having anti-HIV activity, and there is no such compound (4a-e) in Non-Patent Document 11. There are no relevant records on the physiological activities of the compounds (4a-e), and in addition, there is no record suggesting RNR inhibitory activity and antitumor effect in the said non-patent literature 11

Method used

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  • Sulfonamide compound or salt thereof
  • Sulfonamide compound or salt thereof
  • Sulfonamide compound or salt thereof

Examples

Experimental program
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Embodiment

[0561] The present invention will be described in more detail below through examples and test examples, but the present invention is not limited to these examples.

[0562] Regarding various reagents used in Examples, commercially available products were used unless otherwise specified. For silica gel column chromatography, use the SNAP-ULTRA (registered trademark) silica gel prepacked column produced by Baitaiqi Company, or use the SNAP KP-C18-HS (registered trademark) silica gel prepacked column produced by Baitaiqi Company for reverse-phase silica gel column chromatography. Packed column. The reverse-phase separation HPLC column chromatography was implemented according to the following conditions. Appropriately set the injection volume and gradient to implement.

[0563] Chromatographic column: YMC-Actus Triart C18, 30×50mm, 5μm

[0564] UV detection: 254nm

[0565] Column flow rate: 40mL / min

[0566] Mobile phase: water / acetonitrile (0.1% formic acid)

[0567] Inject...

reference example A1

[0605] Reference Example A1 2-(1-bromoethyl)-1-fluoro-3,4-dimethylbenzene

[0606] [chemical 12]

[0607]

[0608] (Step 1) 1-(6-fluoro-2,3-dimethylphenyl)ethanol

[0609] Add methylmagnesium bromide in diethyl ether (3.0M, 70mL) dropwise to a THF solution (300mL) of 6-fluoro-2,3-dimethylbenzaldehyde (22.0g) at 0°C, and then The reaction solution was stirred for 1 hour. Under ice cooling, saturated ammonium chloride aqueous solution (150 mL) was added dropwise, and ethyl acetate (200 mL) was added to separate the layers. The organic layer was washed successively with hydrochloric acid (1M, 200mL), water (200mL) and saturated brine (200mL), then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 1-(6-fluoro-2,3-di Methylphenyl)ethanol (23.7 g).

[0610] (step 2)

[0611] Phosphorus tribromide (26.5 mL) was added dropwise to a chloroform solution (120 mL) of 1-(6-fluoro-2,3-dimethylphenyl) ethanol (23.7 g) obtained in the above step...

reference example A2～A41

[0613] In the same manner as in steps 1 and 2 of Reference Example A1, the starting material aldehyde was reacted with methylmagnesium bromide and then reacted with phosphorus tribromide to obtain the compounds of Reference Examples A2 to A41 shown below. Among them, the compounds of Reference Examples A40 and A41 were produced in the same procedure using ethylmagnesium bromide and methyl-d3-magnesium iodide, respectively, instead of methylmagnesium bromide.

[0614] [Table 1-1]

[0615]

[0616]

[0617] [Table 1-2]

[0618]

[0619]

[0620] [Table 1-3]

[0621]

[0622]

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Abstract

Provided are: a novel sulfonamide compound having ribonucleotide reductase inhibitory activity or a salt thereof; and a pharmaceutical composition which contains this sulfonamide compound or a salt thereof as an active ingredient. A compound represented by formula (I) or a salt thereof. (In the formula, X1 represents an oxygen atom or the like; X2 represents an oxygen atom; X3 represents -NH-; X4represents a hydrogen atom or the like; R1 represents -C(R11)(R12)- or the like; R11 and R12 may be the same or different and each represents a hydrogen atom or the like; R2 represents an optionally substituted C6-C14 aromatic hydrocarbon group or the like; R3 represents an optionally substituted C6-C14 aromatic hydrocarbon group or the like; and R4 represents a hydrogen atom or the like.)

Description

technical field [0001] The present invention relates to a novel sulfonamide compound or its salt with ribonucleotide reductase inhibitory effect, and a pharmaceutical composition containing the sulfonamide compound or its salt as an active ingredient. Background technique [0002] Ribonucleotide reductase (hereinafter also referred to as RNR) consists of a hetero-oligomer of a large subunit M1 and a small subunit M2, both of which require enzymatic activity for expression. RNR recognizes ribonucleoside 5'-diphosphate (hereinafter also referred to as NDP) as a substrate, and catalyzes a reaction for reducing it to 2'-deoxyribonucleoside 5'-diphosphate (hereinafter also referred to as dNDP). RNR is the rate-limiting enzyme in the dNTP de novo (de novo) synthesis pathway, so the role played by RNR in DNA synthesis and replication is essential (Non-Patent Document 1). [0003] It has been reported that RNR enzyme activity is closely related to cell proliferation, and that RNR e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04A61K31/4245A61K31/428A61K31/433A61K31/4439A61K31/444A61K31/454A61K31/4709A61K31/4725A61K31/498A61K31/506A61K31/5377A61K31/538A61K31/5386A61P35/00A61P43/00C07D271/10C07D413/06C07D413/10C07D413/12C07D413/14C07D417/06C07D417/12C07D491/107C07D498/04C07D498/08
CPCC07D413/14C07D413/06C07D413/10C07D413/12C07D417/06C07D417/12C07D491/107C07D498/04C07D498/08A61P35/00C07D271/113C07D249/10A61K31/4245A61K31/428A61K31/433A61K31/4439A61K31/444A61K31/454A61K31/4709A61K31/4725A61K31/498A61K31/506C07D249/04C07D271/10C07D271/07
Inventor 宫原成司上野裕之原翔辉荻野悦夫
Owner TAIHO PHARMA CO LTD
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