2-phenylpyridine derivative

A technology of phenylpyridine and derivatives, applied in the field of 2-phenylpyridine derivatives, can solve the problems of the inhibition of xanthine oxidase and the inhibition of uric acid synthesis, which is not disclosed or implied, and achieves strong inhibition of xanthine oxidase. Effect

Inactive Publication Date: 2007-08-01

ASTELLAS PHARMA INC

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AI-Extracted Technical Summary

Problems solved by technology

[0016] However, in Patent Document 10 and Non-Patent Document 2, neither the inhibitory effect ...

Abstract

The invention provides a 2-phenylpyridine derivative or a salt thereof of formula (I). This compound has satisfying xanthine oxidase-inhibitory action and is useful as a therapeutic or preventive agent for hyperuricemia, gout, inflammatory bowel diseases, diabetic kidney diseases, diabetic retinopathy, or the like. The following are the sign meanings of formula (I): R<1>: H, etc; R<2>: -CO<2>H, etc; R<3> and R<4>:H, etc; R<5>: -CN, etc; R<6>: H, etc; X: -O- and -N(R<8>)- or -S-(under condition that bases indicated by R<5> and -X-R<7> combine at intervals or counterpoints compared with pyridyl); R8: H, etc; R<7>: C<1 to 8> direct or chain alkyl, etc; Y: key, etc; R<9>, R<10> and R<11>:H, etc (condition: when X equals -N(R<8>)-, R<8> and R<7> can have key merger and form nitrogen saturation heterocyclic together the adjacent nitrogen atoms.

Application Domain

Organic active ingredientsOrganic chemistry +9

Technology Topic

Xanthine oxidase inhibitorNitrogen atom +9

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Examples

Experimental program(23)
Effect test(1)

Example Embodiment

[0198] Example

[0199] Hereinafter, the preparation method of the compound (I) of the present invention will be explained in more detail based on Examples. However, the present invention is not limited to the compounds described in the following examples. In addition, the reference example shows the preparation method of the raw material compound.

[0200] In addition, the following abbreviations are used in the reference examples, examples, and the following table.

[0201] Ex: Example number, REx: Reference example number, Dat: Physicochemical data (F: FAB-MS(M+H) + , FN: FAB-MS(M-H) - , ES: ESI-MS(M+H) + , EI: EI-MS(M) + , APN: API-ES-MS(M-H) - , [The compound described as (Na) after the above-mentioned mass analysis measurement value indicates that it was observed as a Na salt, and the compound described as (G-2W) indicates that it was observed as a glycerol adduct dihydrate ], NMR: DMSO-d 6 middle 1 Δ (ppm) of characteristic peak in H NMR, NMRC: CDCl 3 middle 1 Δ (ppm) of the characteristic peaks in H NMR, Str: structural formula, Syn: manufacturing method (the numbers indicate the example numbers manufactured in the same way), Sal. salt (compounds that are not described indicate free bodies), Me: methyl, Et: ethyl, nPr: n-propyl, iPr: isopropyl, nBu. n-butyl, iBu: isobutyl, tBu: tert-butyl, cBu: cyclobutyl, nPen: n-pentyl, iPen: iso Pentyl, cPen: cyclopentyl, nHex: n-hexyl, cHex: cyclohexyl, cHep. cycloheptyl, cOct: cyclooctyl, Bn: benzyl, Ph: phenyl, 2Py: 2-pyridyl, 3Py: 3-pyridyl.

Example Embodiment

[0202] Reference example 1

[0203] In the presence of tetra-n-butylammonium bromide, 5-bromo-2-hydroxybenzonitrile, isobutyl bromide and potassium carbonate are heated in DMF at 80°C to obtain 5-bromo-2-isobutoxybenzonitrile . F: 254, 256

Example Embodiment

[0204] Reference example 2

[0205] After stirring 2,2-dimethyl-1-propanol and sodium hydride in DMF at 0°C, 5-bromo-2-fluorobenzonitrile was added and reacted at room temperature to obtain 5-bromo-2-(2,2 -Dimethylpropoxy)benzonitrile. NMRC: 3.67 (2H, s), 6.83 (1H, d), 7.64 (1H, d)

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Description & Claims & Application Information

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