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Novel sulfonamide compound, preparation method, and use of novel sulfonamide compound as protein tyrosine phosphatase 1B inhibitor

A compound and inhibitor technology, applied in the preparation of sulfonamides, organic chemistry, drug combination, etc., can solve problems such as poor selectivity, poor cell permeability and bioavailability, and easy ionization of proton-containing acid fragments in compounds

Active Publication Date: 2017-01-25
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Aiming at the above-mentioned role of PTP1B in the occurrence of diabetes, a series of PTP1B inhibitors have been discovered in recent years, but most of the highly active PTP1B inhibitors are not ideal because the compounds contain protonic acid fragments, which are easy to ionize, cell permeability and bioavailability , and most of these inhibitors have poor selectivity to other PTPs, especially to T-cell protein tyrosine phosphatase TC-PTP, so it is difficult to become a therapeutically promising inhibitor for in-depth research

Method used

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  • Novel sulfonamide compound, preparation method, and use of novel sulfonamide compound as protein tyrosine phosphatase 1B inhibitor
  • Novel sulfonamide compound, preparation method, and use of novel sulfonamide compound as protein tyrosine phosphatase 1B inhibitor
  • Novel sulfonamide compound, preparation method, and use of novel sulfonamide compound as protein tyrosine phosphatase 1B inhibitor

Examples

Experimental program
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Embodiment 1

[0037]Example 1: [[4-[[Benzenesulfonyl[4-[(benzylmethanesulfonamido)methyl]phenyl]amino]methyl]phenyl]methanesulfonamido]acetate methyl ester (P1) Synthetic specific preparation method: Reaction step a: Place the starting material p-nitrotoluene (15 g, 110 mmol) in a 250 mL three-necked round-bottomed flask, add carbon tetrachloride (100 mL) to dissolve and heat with stirring, until the temperature When it was raised to about 75°C, NBS (19.58 g, 110 mmol) was added in batches, and the stirring was continued for 7 hours. TLC followed the progress of the experiment until the reaction was complete. After the reaction was completed, filter, wash the solid with carbon tetrachloride (100 mL), and distill the filtrate under reduced pressure, dissolve it with ethyl acetate, wash with saturated brine (2×100 mL), dry over anhydrous Na2SO4, and remove the solvent by distillation under reduced pressure . The obtained solid was recrystallized with ethanol, and a pale yellow needle-like so...

Embodiment 2

[0038] Example 2. [[4-[[[4-[(Benzylmethanesulfonamido)methyl]phenyl]-(4-methoxybenzenesulfonamido)]methyl]phenyl]methanesulfonamide Synthesis of methyl] acetate (P2) R 6 Reaction step g: Dissolve the starting material in p-phenol (3 g, 32 mmol) and place in a 100 mL round bottom flask, add methanol to dissolve, then add KOH (2.69 g, 48 mmol) and stir, nitrogen protection Dimethyl sulfate (6.06 g, 48 mmol) was added at 0°C to continue stirring, and then warmed to room temperature for reaction. After reacting for 5 hours, TLC detected that the reaction was complete, cooled to room temperature, distilled off methanol under reduced pressure, added ethyl acetate (80 mL) to the reaction solution, and washed the organic phase with saturated brine (3×100 mL), and washed the organic phase with Anhydrous NaSO 4 dry. The organic solvent was distilled off under reduced pressure, and the resulting product anisole was 1.94 g. Yield: 56%. Reaction step h: the above-mentioned compound ani...

Embodiment 3

[0039] Example 3. [[4-[[[4-[(Benzylmethanesulfonylamino)methyl]phenyl]-(4-ethoxybenzenesulfonylamino)]methyl]phenyl]methanesulfonamide Synthesis of methyl] acetate (P3) R 6 Be ethyl; Reaction step 2a (preparation of compound 2B): dissolving starting material in p-phenol (1.88 g, 20 mmol) is placed in 100mL round bottom flask, adds DMF to dissolve, then adds K 2 CO 3 (4.14 g, 30 mmol) was heated and stirred at 70°C, and bromoethane (2.3 mL, 30 mmol) was added after 30 min to continue stirring, and then warmed to room temperature for reaction. After reacting for 3 hours, after the reaction was complete as detected by TLC, cool to room temperature, filter the reaction solution and wash with ethyl acetate (2 × 70 mL), combine the organic phases and wash with saturated brine, separate the organic phases and wash with anhydrous Na 2 SO 4 Drying, distillation under reduced pressure to remove the solvent and column chromatography yielded 1.72 g of pure phenetole: 70%; then refer to...

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Abstract

The invention relates to a novel sulfonamide compound in a structure of a general formula I as shown in the specification, or pharmaceutically acceptable salt and a preparation method of the novel sulfonamide compound, and further relates to a drug composition containing the compound as shown as the general formula I or the pharmaceutically acceptable salt of the compound, and a use of the compound or the pharmaceutically acceptable salt for preparing a drug for preventing and / or treating symptoms or diseases such as hyperglycemia and diabetes mellitus type 2 since the compound as shown as the general formula I or the pharmaceutically acceptable salt of the compound has activity of inhibiting a protein tyrosine phosphatase 1B (PTP 1B).

Description

technical field [0001] The invention relates to the field of medicinal chemistry, and specifically describes a preparation method of a novel protein tyrosine esterase 1B inhibitor compound molecule and its use in the treatment of diabetes, especially type II diabetes and obesity. Background technique [0002] Diabetes is a chronic metabolic disease characterized by hyperglycemia. Sustained hyperglycemia can lead to many complications, such as retinal, renal, nervous system and microvascular complications. Diabetes can be divided into two types according to the pathogenesis: insulin-dependent diabetes mellitus (IDDM type I) and non-insulin-dependent diabetes mellitus (NIDDM type II diabetes). The incidence of type I diabetes is relatively low, and it often occurs in children and adolescents, accounting for about 5% of the total number of diabetic patients. and secrete insulin. The pathogenesis of type Ⅱ diabetes is complex, and its common pathological features are relative...

Claims

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Application Information

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IPC IPC(8): A61K31/223A61P3/10C07C311/08C07C303/38
Inventor 杜永丽李群益沈竞康刘培红
Owner QILU UNIV OF TECH
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