Tetrahydrocyclopenta[c]pyrrole derivative, preparation method and medical applications thereof
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A compound and cycloalkyl technology, applied in the field of tetrahydrocyclopentadieno[c]pyrrole derivatives, can solve problems such as the influence of administration time, the slow onset of acid breakthrough at night, and instability
Inactive Publication Date: 2016-03-02
JIANGSU CAREFREE PHARM CO LTD +2
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Problems solved by technology
Such as: the influence of administration time on drug efficacy; slow onset of acid breakthrough at night; instability under acidic conditions (need to be formulated into intestinal preparations); dependence on CYP450 enzymes (resulting in significant individual differences), etc.
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Embodiment 1
[0065] Embodiment 1: the preparation of compound 1
[0066]
[0067] 1) Preparation of 5,6-dihydrocyclopenta[c]pyrrol-4(2H)-one (compound B)
[0068] At 0-5°C, a mixed solution of compound A (2.1g, 25.64mmol), p-methylsulfonylmethylisonitrile (5g, 25.64mmol), diethyl ether (20mL) and DMSO (20mL) was added dropwise to NaH (1.64g, 41mmol, 1.6eq), ether (15mL) solution. After the dropwise addition, the temperature was naturally raised to room temperature, and the reaction was stirred for 2 hours. .LC-MS detected that the reaction of the raw materials was complete, adding pure water (20mL) to the phase reaction system to quench the reaction, stirring for 15min, and extracting with diethyl ether (15mLx3) and ethyl acetate (15mLx3) respectively. The combined organic phases were dried, concentrated, and passed through a column (P:E=1:1) to obtain compound B (1.67 g, yield: 53.87%) as a yellow solid. HPLC: 85%; MS (ESI) m / z: [M+H] + =122.4;
[0069] 2) Preparation of 1-b...
Embodiment 2
[0078] Embodiment 2: the preparation of compound 2
[0079] Referring to the similar method of compound 1, 26 mg of compound 2 yellow oil was obtained. 1 H-NMR (400MHz, CDCl 3 )δ:8.71(d,1H),8.54(d,1H),7.60(d,1H),7.37(m,5H),7.11(m,2H),3.64(m,1H),2.55(t,2H ), 1.99(m,1H), 1.81(m,1H), 1.50(m,5H)ppm.
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Abstract
The present invention relates to a class of new tetrahydrocyclopenta[c]pyrrole derivatives represented by a general formula (I) and a preparation method thereof, a pharmaceutical composition containing the derivative, and uses of the tetrahydrocyclopenta[c]pyrrole derivative as the treatment agent, particularly the gastric acid secretion inhibitor and the potassium ion competitive acid blocker (P-CABs). Each substituent in the general formula (I) is defined in the specification. The general formula (I) is defined in the specification.
Description
technical field [0001] The present invention relates to a new class of tetrahydrocyclopentadieno[c]pyrrole derivatives, a process for their preparation, pharmaceutical combinations containing the derivatives and their use as therapeutic agents, especially as gastric acid secretion inhibitors and potassium ion competitive agents. Use of acid blockers (P-CABs). Background technique [0002] Since 1988, proton pump inhibitors represented by omeprazole have been widely used clinically to treat peptic ulcer, reflux esophagitis and Zoller-Ellison syndrome by inhibiting gastric acid secretion. Long-term clinical application has found that existing proton pump inhibitors still have limitations in terms of pharmacokinetics and pharmacodynamics. Such as: the effect of administration time on drug efficacy; slow onset of acid breakthrough at night; instability under acidic conditions (need to be formulated into intestinal preparations); dependence on CYP450 enzymes (resulting in signif...
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