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A technology of thiosorbitol and compounds, applied in the fields of carbocyclic sugars, metabolic diseases, organic chemistry, etc., can solve the problem of strong inhibition without reports
Inactive Publication Date: 2009-07-08
TAISHO PHARMACEUTICAL CO LTD
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[0008] So far, C-phenyl sorbitol derivatives having selective inhibitory activity against SGLT2 have been reported (see Patent Document 9), but C-phenyl 1-thiosorbitol derivatives that strongly inhibit both SGLT1 and SGLT2 not yet reported
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preparation example Construction
[0106] The preparation method of intermediate (II)
[0107] The production methods of intermediates (II) and (VIII) necessary for the production of the compound (I) of the present invention are shown below. Among them, D 1 Indicates Li or MgBr, and other symbols have the same meaning as above.
[0108] 【Chemical 6】
[0109]
[0110] (17) Step 17 (Coupling)
[0111] Aryllithium reagents can be prepared by using organometallic reagents such as n-butyllithium, sec-butyllithium, and tert-butyllithium for intermediate compound (XXII). Compound (XXIII) can be obtained by adding thiolactone (XVI) thereto. The solvent used for the reaction at this time may, for example, be tetrahydrofuran, diethyl ether or toluene. The reaction temperature is -80°C to room temperature, preferably -78°C to -25°C.
[0112] (18) Step 18 (acid hydrolysis)
[0113] Compound (VIII) can be produced by hydrolyzing the acetal group in compound (XXIII) with hydrochloric acid, p-toluenesulfonic acid mo...
Embodiment
[0151] The present invention will be further described in detail below in conjunction with reference examples, examples and test examples.
reference example 1
[0153] Preparation of 2,3,4,6-tetra-O-benzyl-5-thio-D-glucono-1,5-lactone (compound (XVI))
[0154] 【chemical 8】
[0155]
[0156] (1) Preparation of tetrahydro-2H-pyran-2-yl 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose
[0157] To a solution of 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose (2.0 g, 5.49 mmoL) in chloroform (40 mL), add 3,4-dihydro-2H -pyran (1.5 mL, 16.5 mmoL) and p-toluenesulfonic acid monohydrate (104 mg, 0.549 mmoL), stirred at room temperature for 1 hour. Saturated aqueous sodium bicarbonate solution was added to the reaction liquid, followed by extraction with chloroform, and the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the title compound (2.56 g) as a light yellow amorphous substance.
[0158] (2) ...
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Abstract
A C-phenyl 1-thioglucitol compound represented by the formula (I), a pharmaceutically acceptable salt thereof, or a hydrate of the compound or the pharmaceutically acceptable salt. (I) wherein X represents a hydrogen atom or a C1-6 alkyl group; Y represents a C1-6 alkylene group or -O-(CH2)n- (n represents an integer ranging from 1 to 5); and Z represents -CONHR or -NHCONHR (provided that, when Z represents -NHCONHR, n is not 1), where R represents a C1-6 alkyl group substituted by 1 to 3 groups independently selected from a hydroxyl group and -CONH2; and R represents a hydrogen atom or a C1-6 alkyl group substituted by 1 to 3 groups independently selected from a hydroxyl group and -CONH2. The compound, the salt or the solvate can inhibit the SGLT1 activity to prevent the absorption of glucose or the like, or can inhibit both the SGLT1 activity and the SGLT2 activity to prevent the absorption of glucose or the like and excrete a urine sugar, and is therefore useful as a prophylactic or therapeutic agent for diabetes.
Description
technical field [0001] The present invention relates to sodium-dependent glucose cotransporter 1 (SGLT1) activity inhibitory involved in the absorption of glucose, etc. in the small intestinal epithelium, or sodium-dependent glucose cotransporter involved in renal glucose reabsorption in addition to this action 2 (SGLT2) activity-inhibiting C-phenyl 1-thiosorbitol compounds. Background technique [0002] If you have diabetes, your fasting blood sugar level should be above 126 mg / dL. In addition, even if the fasting blood sugar level is normal, if it shows a high blood sugar level of 140 to 200 mg / dL after a meal, it will be diagnosed as impaired glucose tolerance (hereinafter referred to as IGT (impaired glucose tolerance)). It is believed that delaying the onset of diabetes from IGT can reduce the risk of cardiovascular disorders, and some knowledge has been obtained to show this view. For example, in the Da Qing IGT and Diabetes Study (Da Qing IGT and Diabetes Study) con...
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