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Process for preparing compounds useful as sglt inhibitors

A compound and solvate technology, applied in the field of preparing compounds that can be used as SGLT inhibitors, can solve problems such as destroying and deteriorating cycles

Inactive Publication Date: 2011-11-30
JANSSEN PHARMA NV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is possible to prevent or treat diabetes by breaking the above-mentioned cycle of self-deterioration by treating hyperglycemia

Method used

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  • Process for preparing compounds useful as sglt inhibitors
  • Process for preparing compounds useful as sglt inhibitors
  • Process for preparing compounds useful as sglt inhibitors

Examples

Experimental program
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preparation example Construction

[0272] The present invention relates to a process for the preparation of compounds of formula (I), as shown in Scheme 1 below.

[0273]

[0274] Correspondingly, let suitably substituted formula (X) compound (wherein Q 0 is bromine or iodine; which are known compounds or compounds prepared by known methods) and bis(C 1-4 Alkyl) magnesium-lithium chloride complexes (such as di(sec-butyl) magnesium-lithium chloride, etc.) or C 1-4 Alkylmagnesium chloride-lithium chloride complex or C 1-4 Alkyl magnesium bromide-lithium chloride complex (wherein C 1-4 The alkyl group is preferably isopropyl or sec-butyl, more preferably sec-butyl; it is a known compound or a compound prepared by a known method) reaction; wherein two (C1-4 Alkyl) magnesium-lithium chloride complex or C 1-4 Alkylmagnesium chloride-lithium chloride complex or C 1-4 The alkylmagnesium bromide-lithium chloride complex is preferably present in the range of about 1.0 to 1.5 molar equivalents (relative to the mole...

example 1

[0422] Example 1: Acetic acid-3(R), 4(S), 5(R)-triacetoxy-6-{3-[5-(4-fluorophenyl)-thiophene -2-ylmethyl]-4-methyl-phenyl}-6-hydroxy-tetrahydropyran-2(R)-ylmethyl ester

[0423]

[0424] Step A: Preparation of Grignard Reagent

[0425] 2-(4-Fluorophenyl)-5-(5-iodo-2-methyl-benzyl)thiophene (122.48 g, 0.3 mol) was stirred in toluene (0.75 L / mol) at ambient temperature, then Cool to -10°C. Then, sec-butylmagnesium chloride lithium chloride (about 15% solution in THF; 269.70 g, 0.36 mol ), and the resulting dark green solution was stirred between -5 °C and 0 °C for 1 h.

[0426] Step B :

[0427]Dilute acetate-3(R),4(S),5(R)-triacetoxy-6-oxo-tetrahydropyran-2(R)-ylmethyl ester with THF (0.25 L / mol) ( about 50% solution in toluene, 0.39 mol), and the resulting mixture was cooled to -35°C. To this mixture was then added the solution prepared in Step A above via a syringe / addition funnel at less than about -35°C for about 1 hour under an argon atmosphere. After stir...

example 2

[0428] Example 2: Acetic acid-3(R), 4(R), 5(S)-triacetoxy-6(S)-{3-[5-(4-fluorophenyl)- Thiophen-2-ylmethyl]-4-methyl-phenyl}-tetrahydropyran-2(R)-ylmethyl ester

[0429]

[0430] Triethylsilane (87.2 g, 0.75 mol) was added to the Base)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxy-tetrahydropyran-2(R)-ylmethyl ester in acetonitrile (as prepared in Example 1 above, 0.30 mol), the resulting brown solution was cooled to 2 °C. Then, boron trifluoride etherate (46.84 g, 0.33 mol) was added via syringe over about 30 minutes, and the resulting mixture was stirred in an ice-water bath for 1 hour. To the resulting mixture was then added 10% w / w Na 2 CO 3 Aqueous solution (330ml). The resulting mixture was then heated at about 45°C until complete dissolution was observed. The layers of the resulting three-layer mixture were separated and the intermediate organic layer was allowed to cool to ambient temperature with stirring for 16 hours, during which time crystallization w...

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Abstract

The present invention relates to a novel process for the preparation of compounds having inhibitory activity on sodium-dependent glucose transporter (SGLT) present in the intestine or kidney.

Description

[0001] Cross references to related patent applications [0002] This patent application claims priority to U.S. Provisional Patent Application No. 61 / 106,231, filed October 17, 2008, and U.S. Provisional Patent Application No. 61 / 106,260, filed October 17, 2008, which are incorporated by reference in their entirety way incorporated into this article. technical field [0003] The present invention relates to a novel process for the preparation of compounds having inhibitory activity on sodium-dependent glucose transporter (SGLT) present in the intestine or kidney. Background technique [0004] Diet therapy and exercise therapy are the basic ways to treat diabetes. When these therapies do not adequately control the patient's condition, insulin or oral antidiabetic agents may additionally be used to treat diabetes. Currently, used as antidiabetic agents are: biguanide compounds, sulfonylurea compounds, agents for improving insulin resistance, and α-glucosidase inhibitors. Ho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/10C07H7/04C07H13/04C07C1/00C07D333/12C07D409/10
CPCC07H13/04C07D333/12C07H7/04C07D409/10A61P3/10A61K31/381C07D409/14
Inventor W·F·M·菲利尔斯R·L·M·布雷克斯P·H·J·尼斯特M·哈特苏达M·尤施纳加M·亚达C·特勒哈
Owner JANSSEN PHARMA NV
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