Derivatives of isosorbid mononitrate, utilization as vasodilator agents with reduced tolerance
A technology of isosorbide and nitrate, applied in the direction of cardiovascular system diseases, drug combinations, active ingredients of heterocyclic compounds, etc., can solve the problems of low vasodilation activity and high tolerance
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Embodiment 2
[0059] (CH 2 ), 23.84 (CH 2 -S), 14.31 (CH 3 ). Example 2 Obtaining 5-(2'-ethylthio) nicotinate 2-mononitrate hydrochloride of isosorbide
[0060] Step 1. The same method as in Step 2 in Example 1 was used, and 2-mononitrate of isosorbide was used as the starting compound. The chemical yield of the expected compound was obtained in 88%.
[0061] Step 2. In the 500 milliliters of three-neck glass flasks of the reflux condenser of calcium chloride tube sealing, magnetic stirrer and constant pressure dropping funnel, 7.0 grams (19.66 millimoles) the product that last step obtains is dissolved in 200 milliliters A mixed solution of EtOEt and 100 ml of dichloromethane. The solution was stirred at room temperature, and 30 ml of hydrogen chloride-saturated EtOEt solution (prepared by passing hydrogen chloride gas directly into EtOEt until saturation) was added drop by drop, and a white solid was precipitated. The solid was filtered off, washed with excess EtOEt, and dried unde...
Embodiment 3
[0074] 23.67 (CH 2 ), 14.14 (CH 3 ). Example 3 Obtaining 2-(2'-mercapto) nicotinic acid ester 5-mononitrate (3) of isosorbide
[0075] Step 1. In a 100-ml glass flask equipped with a calcium chloride tube-sealed reflux condenser and a magnetic stirrer, 3.0 g (19.35 mmol) of 2-mercaptonicotinic acid was suspended in 30 ml of thionyl chloride (1.64 g / ml, 431.4 mmol). The mixture was continued to reflux for 2 hours, during which time dissolution of the solid was observed. The mixture was cooled and excess thionyl chloride was removed under reduced pressure with addition of portions of toluene. After drying under reduced pressure, 3.35 g of an orange-yellow solid was obtained, which was the expected acid chloride. Yield: 100%.
[0076]Step 2. In a 250 ml glass flask equipped with a reflux condenser and a magnetic stirrer, 3.0 g (17.29 mmol) of the acid chloride obtained in the previous step was suspended in 75 ml of pyridine under an argon atmosphere. The suspension was c...
Embodiment 7
[0099] 13 C-NMR (50MHz, DMSO-d 6 ): 163.91 (C=O), 161.64 (C ar-COO), 152.80 (CH ar ), 139.27 (CH ar ), 122.20 (C ar -S), 118.83 (CH ar ), 85.97 (CH-ONO 2 ), 82.41(CH), 81.53(CH), 77.87(CH-O-CO), 72.67(CH 2 ), 69.07 (CH 2 ), 13.34 (CH 3 ). Embodiment 7 Obtain 5-(2'-methylthio)nicotinate 2-mononitrate hydrochloride of isosorbide ( 7 )
[0100] In a 50 mL glass flask equipped with a magnetic stirrer and a reflux condenser, 2.00 g (10.7 mmol) of 2-methylthionicotinoyl chloride was suspended in 12 mL of pyridine under an argon atmosphere. The mixture was cooled in an ice bath, and 2.04 g (10.7 mmol) of 5-mononitrate of isosorbide were added. The reaction mixture was stirred at room temperature under an atmosphere of argon for 15 hours. Thereafter, the solvent was removed under reduced pressure, the residue was dissolved in 50 ml of chloroform and washed: first with 50 ml of water, then with 50 ml of 5% aqueous hydrochloric acid and finally with 50 ml of water again. ...
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