Pleuromutilin 2-[(diphenylmethyl)thio] acetic acid ester with anti-drug resistant bacteria activity and a method of preparing the same

التفاصيل البيبلوغرافية
العنوان: Pleuromutilin 2-[(diphenylmethyl)thio] acetic acid ester with anti-drug resistant bacteria activity and a method of preparing the same
Patent Number: 11512,049
تاريخ النشر: November 29, 2022
Appl. No: 17/239582
Application Filed: April 24, 2021
مستخلص: A compound with anti-drug resistant bacteria activity having the formula (I): [chemical expression included] (I) is disclosed. The methods of preparing the compound of formula (I) are also disclosed.
Inventors: Zhao, Qianqian (Xi'an, CN); Zhao, Yuqing (Xi'an, CN); Yang, Dan (Xi'an, CN); Li, Jingyi (Xi'an, CN); Xin, Liang (Xi'an, CN); Bian, Ruina (Xi'an, CN); Zhang, Jie (Xi'an, CN); Li, Han (Xi'an, CN); Tian, Bin (Xi'an, CN); Wang, Yongbo (Xi'an, CN); Liang, Chengyuan (Xi'an, CN); Qi, Liang (Xi'an, CN); Mao, Gennian (Xi'an, CN)
Assignees: SHAANXI UNIVERSITY OF SCIENCE AND TECHNOLOGY (Xi'an, CN)
Claim: 1. A compound with anti-drug resistant bacteria activity having the following formula [chemical expression included]
Claim: 2. A method of preparing the compound of formula (I) of claim 1 , comprising: reacting a compound of formula (II) with a compound of formula (III) to obtain the compound of formula (I), [chemical expression included]
Claim: 3. The method of claim 2 , wherein the reaction of the compound of formula (II) with the compound of formula (III) comprises the following steps: placing the compound of formula (II) and the compound of formula (III), in a molar ratio of 1:1 to 1:1.3, in a reactor; adding an organic solvent and a catalytic amount of triethylamine under a nitrogen atmosphere to obtain a reaction mixture; heating the reaction mixture at 20-60° C. for 3-6 hours; extracting the reaction mixture with ethyl acetate to obtain a crude product; and purifying the crude product on a silica gel chromatography column with petroleum ether and ethyl acetate as an eluent to obtain the compound of formula (I).
Claim: 4. The method of claim 3 , wherein the organic solvent is selected from the group consisting of toluene, dichloromethane and N,N-dimethylformamide.
Claim: 5. The method of claim 4 , wherein the organic solvent is dichloromethane.
Claim: 6. The method of claim 3 , wherein the molar ratio of the compound of formula (II) and the compound of formula (III) is 1:1.1.
Claim: 7. The method of claim 3 , wherein the reaction mixture is heated at 25° C.
Claim: 8. The method of claim 3 , wherein the reaction mixture is heated for 5 hours.
Claim: 9. The method of claim 3 , wherein the eluent is petroleum ether:ethyl acetate=4:1.
Claim: 10. A method of preparing the compound of formula (I) of claim 1 , comprising: reacting a compound of formula (II) with a compound of formula (IV) to obtain the compound of formula (I): [chemical expression included]
Claim: 11. The method of claim 10 , wherein the reaction of the compound of formula (II) with the compound of formula (IV) comprises the following steps: placing the compound of formula (II), a catalyst, and an ionic liquid in a reactor under nitrogen atmosphere, the catalyst being 12-molybdosilicic acid hydrate of formula H 6 Mo 12 O 41 Si; adding the compound of formula (IV) to the reactor to form a reaction mixture; heating the reaction mixture at 20-50° C. for 4-8 hours; placing the reaction mixture in a separating funnel to separate a crude product; purifying the crude product by recrystallization in methanol to obtain the compound of formula (I); and recycling the ionic liquid.
Claim: 12. The method of claim 11 , wherein the ionic liquid is selected from the group consisting of 1-octyl-3-methylimidazolium and hexafluorophosphate, 1-hexyl-3-methylimidazolium tetrafluoroborate and 1-butyl-3-methylimidazolium tetrafluoroborate of formula [BMIM][BF4].
Claim: 13. The method of claim 12 , wherein the ionic liquid is 1-butyl-3-methylimidazolium tetrafluoroborate.
Claim: 14. The method of claim 11 , wherein the compound of formula (II) and the compound (IV) have a molar ratio of 1:1 to 1:1.3.
Claim: 15. The method of claim 14 , wherein the molar ratio of the compound of formula (II) and the compound of formula (IV) is 1:1.1.
Claim: 16. The method of claim 11 , wherein the reaction mixture is heated at 30° C.
Claim: 17. The method of claim 11 , wherein the reaction mixture is heated for 6 hours.
Patent References Cited: 7045524 May 2006 Dean
Primary Examiner: Muresan, Ana Z
رقم الانضمام: edspgr.11512049
قاعدة البيانات: USPTO Patent Grants