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Tetrazoleacetic acid compound, as well as preparation method and applications thereof

A technology of compounds and products, applied in the fields of organic chemistry, drug combination, bone diseases, etc., can solve the problems of fulminant hepatitis, allopurinol liver and bone marrow toxicity, allergies, etc.

Active Publication Date: 2015-02-11
符瑶
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have different degrees of toxic and side effects, such as benzbromarone has the risk of causing fulminant hepatitis, allopurinol has adverse reactions such as liver and bone marrow toxicity and allergic reactions, etc.

Method used

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  • Tetrazoleacetic acid compound, as well as preparation method and applications thereof
  • Tetrazoleacetic acid compound, as well as preparation method and applications thereof
  • Tetrazoleacetic acid compound, as well as preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The synthesis of embodiment 1 compound I-1

[0024]

[0025] A. Synthesis of Compound IV-1

[0026] 3.98g (20mmol) of compound II-1 and 2.96g (20mmol) of compound III-1 were dissolved in 40mL of dry DMF, stirred, added 3.32g (20mmol) of potassium iodide and 6.91g (50mmol) of potassium carbonate, in a nitrogen atmosphere 100 React at °C until the reaction is complete (TLC tracking, generally 5h). After the reaction mixture was cooled, it was poured into 300 mL of ice water, stirred, and 100 mL × 3 CH 2 Cl 2 After extraction, the extract phases were combined, washed with 100 mL of 5% brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound IV-1, a white solid, ESI-MS, m / z=289 ([M+Na] + ).

[0027] B. Synthesis of Compound VI-1

[0028] 3.19g (12mmol) of compound IV-1 and 1.12g (12m...

Embodiment 2-5

[0034] Referring to the operation steps of Example 1, the compounds listed in the following table were prepared.

[0035]

[0036]

Embodiment 6

[0038] The compounds of the present invention and related compounds inhibit IC of URAT1 50 The values ​​were determined in a similar manner as described in the literature (Example 12 in US2014 / 0005136).

[0039] Construction of a cell line stably expressing the humanized URAT1 transporter: The humanized URAT1 gene (SLC22A112) was subcloned from the plasmid pCMV6-XL-5 (Origene) into the eukaryotic expression plasmid pCMV6 / neo (Origene). Gene sequencing confirmed that the humanized URAT1 was consistent with the information recorded in the gene bank (NM_144585.2). HEK293 human embryonic kidney cells (ATCC#CRL-1573) were cultured in EMEM tissue culture medium under 5% CO 2 And cultured in 95% air atmosphere. pCMV6 / Neo / URAT1 was transfected onto HEK293 cells using L2000 type transfection agent (Invitrogene). After 24 hours, the transfected cells were divided into tissue culture dishes with a diameter of 10 cm, continued to grow for one day, and then the medium was replaced with ...

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PUM

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Abstract

The invention relates to the field of medicaments related to hyperuricemia and gout. In particular, the invention relates to a tetrazoleacetic acid structure-containing uric acid transporter 1 inhibitor, a preparation method thereof, a medicament composition containing the inhibitor, and applications of the inhibitor to preparation of diabetes medicaments. The structural formula is shown in the specification, wherein R<1> is selected from H, alkyls of C1-C5, and cycloalkyls of C3-C6.

Description

technical field [0001] The invention relates to the field of drugs related to the treatment of hyperuricemia and gout. Specifically, the present invention relates to a class of uric acid transporter 1 (urate transporter 1, URAT1) inhibitors containing a tetrazolium acetic acid structure that have a therapeutic effect on hyperuricemia and gout, a preparation method, and a pharmaceutical composition containing them and its use in medicine. Background technique [0002] Gout is a chronic metabolic disease characterized by hyperuricemia and pain caused by deposition of monosodium uric acid (MSU) in joints and other parts. The main reason is purine metabolism disorder and / or uric acid excretion disorder. It is estimated that there are more than 20 million gout patients worldwide. Drugs currently used to treat gout include anti-inflammatory drugs for pain relief (such as colchicine, etc.), drugs that inhibit uric acid production (xanthine oxidase inhibitors represented by allopu...

Claims

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Application Information

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IPC IPC(8): C07D257/04A61P19/06
CPCC07D257/04
Inventor 不公告发明人
Owner 符瑶
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