Patent
Pleuromutilin (phenylthio)acetic acid ester with anti-drug resistant bacteria activity and a method of preparing the same
| العنوان: | Pleuromutilin (phenylthio)acetic acid ester with anti-drug resistant bacteria activity and a method of preparing the same |
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| Patent Number: | 11518,740 |
| تاريخ النشر: | December 06, 2022 |
| Appl. No: | 17/239575 |
| Application Filed: | April 24, 2021 |
| مستخلص: | A compound with anti-drug resistant bacteria activity having the following formula (I): [chemical expression included] is disclosed. The methods of preparing the compound of formula (I) are also disclosed. |
| Inventors: | Zhao, Qianqian (Xi+3 an, CN); Zhang, Jie (Xi+3 an, CN); Xin, Liang (Xi+3 an, CN); Li, Jingyi (Xi+3 an, CN); Bian, Ruina (Xi+3 an, CN); Zhao, Yuqing (Xi+3 an, CN); Yang, Dan (Xi+3 an, CN); Li, Han (Xi+3 an, CN); Tian, Bin (Xi+3 an, CN); Wang, Yongbo (Xi+3 an, CN); Liang, Chengyuan (Xi+3 an, CN) |
| Assignees: | SHAANXI UNIVERSITY OF SCIENCE AND TECHNOLOGY (Xi'an, CN) |
| Claim: | 1. A compound with antibacterial activity against drug resistant bacteria having the following formula (I): [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 toluene, dichloromethane or 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=1:1. |
| 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 1-octyl-3-methylimidazolium hexafluorophosphate, 1-hexyl-3-methylimidazolium tetrafluoroborate, or 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF 4 ]). |
| 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: | 3979423 September 1976 Riedl 20030162831 August 2003 Ascher 20100184987 July 2010 Jaber 109384698 February 2019 111170893 May 2020 |
| Primary Examiner: | Bonaparte, Amy C |
| رقم الانضمام: | edspgr.11518740 |
| قاعدة البيانات: | USPTO Patent Grants |
| الوصف غير متاح. |