CN106478724B - 一种噁唑烷酮类抗菌药物的晶型c及其制备方法和应用 - Google Patents
一种噁唑烷酮类抗菌药物的晶型c及其制备方法和应用 Download PDFInfo
- Publication number
- CN106478724B CN106478724B CN201610813284.5A CN201610813284A CN106478724B CN 106478724 B CN106478724 B CN 106478724B CN 201610813284 A CN201610813284 A CN 201610813284A CN 106478724 B CN106478724 B CN 106478724B
- Authority
- CN
- China
- Prior art keywords
- crystal form
- oxazolidinone antibacterials
- antibacterials
- preparation
- suo shu
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 50
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 229940088710 antibiotic agent Drugs 0.000 title claims abstract description 48
- 239000013078 crystal Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000003814 drug Substances 0.000 claims abstract description 17
- 230000003115 biocidal effect Effects 0.000 claims abstract description 6
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000001228 spectrum Methods 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000012296 anti-solvent Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 239000012535 impurity Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 238000010304 firing Methods 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 230000007096 poisonous effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- 239000007787 solid Substances 0.000 description 15
- 238000000634 powder X-ray diffraction Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical group 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- -1 calcium salt salt Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610813284.5A CN106478724B (zh) | 2016-09-09 | 2016-09-09 | 一种噁唑烷酮类抗菌药物的晶型c及其制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610813284.5A CN106478724B (zh) | 2016-09-09 | 2016-09-09 | 一种噁唑烷酮类抗菌药物的晶型c及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106478724A CN106478724A (zh) | 2017-03-08 |
CN106478724B true CN106478724B (zh) | 2018-04-17 |
Family
ID=58273605
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610813284.5A Expired - Fee Related CN106478724B (zh) | 2016-09-09 | 2016-09-09 | 一种噁唑烷酮类抗菌药物的晶型c及其制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN106478724B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107353305A (zh) * | 2017-07-12 | 2017-11-17 | 浙江普洛得邦制药有限公司 | 一种噁唑烷酮类抗菌药物的三羟甲基氨基甲烷盐及其晶型a、制备方法和应用 |
CN110128473A (zh) * | 2019-06-21 | 2019-08-16 | 碧豫药业有限责任公司 | 一种噁唑烷酮类抗菌药物游离酸的晶型ⅲ及其制备方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1749256A (zh) * | 2004-09-16 | 2006-03-22 | 中国科学院上海药物研究所 | 一类新的噁唑烷酮衍生物、其制备方法和用途 |
CN102260277A (zh) * | 2010-05-24 | 2011-11-30 | 中国科学院上海药物研究所 | 新型苯并噁嗪噁唑烷酮类化合物及其制备方法和用途 |
CN103896963A (zh) * | 2012-12-26 | 2014-07-02 | 中国科学院上海药物研究所 | 苯并噁嗪噁唑烷酮类化合物及其制备方法和用途 |
CN106083837A (zh) * | 2016-05-27 | 2016-11-09 | 浙江普洛得邦制药有限公司 | 一种噁唑烷酮类抗菌药物及其中间体的制备方法 |
-
2016
- 2016-09-09 CN CN201610813284.5A patent/CN106478724B/zh not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1749256A (zh) * | 2004-09-16 | 2006-03-22 | 中国科学院上海药物研究所 | 一类新的噁唑烷酮衍生物、其制备方法和用途 |
CN102260277A (zh) * | 2010-05-24 | 2011-11-30 | 中国科学院上海药物研究所 | 新型苯并噁嗪噁唑烷酮类化合物及其制备方法和用途 |
CN103896963A (zh) * | 2012-12-26 | 2014-07-02 | 中国科学院上海药物研究所 | 苯并噁嗪噁唑烷酮类化合物及其制备方法和用途 |
CN106083837A (zh) * | 2016-05-27 | 2016-11-09 | 浙江普洛得邦制药有限公司 | 一种噁唑烷酮类抗菌药物及其中间体的制备方法 |
Non-Patent Citations (1)
Title |
---|
Solubility-Driven Optimization of (Pyridin-3-yl)Benzoxazinyl-oxazolidinones Leading to a Promising Antibacterial Agent;Bin Guo et al.;《Journal of Medicinal Chemistry》;20130221;第2642-2650页 * |
Also Published As
Publication number | Publication date |
---|---|
CN106478724A (zh) | 2017-03-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101891738B (zh) | 达沙替尼多晶型物及其制备方法和药用组合物 | |
TWI711626B (zh) | 達格列淨新穎特別晶型及其製備方法 | |
MXPA06014458A (es) | Cristal del compuesto de 1,2-dihidropiridina y metodo para producir el mismo. | |
CN106632481B (zh) | 一种噁唑烷酮类抗菌药物的晶型a及其制备方法和应用 | |
CN106478723B (zh) | 一种噁唑烷酮类抗菌药物的晶型b及其制备方法和应用 | |
CN103833626B (zh) | 西达本胺的晶型及其制备方法与应用 | |
AU2015374763B2 (en) | Method for preparing Sofosbuvir crystal form-6 | |
CN106478724B (zh) | 一种噁唑烷酮类抗菌药物的晶型c及其制备方法和应用 | |
CN103342673A (zh) | 一种奥拉西坦晶型及其制备方法 | |
CN106008529A (zh) | 一种依鲁替尼溶剂化物及其制备方法 | |
UA54411C2 (uk) | Кристалічна форма n-(4-трифторметилфеніл)-5-метилізоксазол-4-карбоксаміду та спосіб одержання кристалічних форм | |
CN105061420B (zh) | 一种jak抑制剂的晶型及其制备方法和应用 | |
EP3569590A1 (en) | (r)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form, preparation method therefor, and application thereof | |
CN103524532B (zh) | 一种头孢唑肟钠化合物晶型、制备方法及其药物制剂 | |
CN102942577B (zh) | 一种含有头孢西丁钠化合物的药物组合物 | |
CN106866666B (zh) | 一种帕博西尼晶型化合物及其制备方法 | |
CN102887829B (zh) | 芬戈莫德粘酸盐及其晶体的制备方法和用途 | |
HUE030504T2 (en) | Process for the preparation of ralfinamide methanesulfonate salts or their R-enantiomers | |
CN109053738B (zh) | 一种依鲁替尼的溶剂化物及其制备方法 | |
CN111712486B (zh) | 卡利拉嗪盐酸盐的晶型及其制备方法及其用途 | |
CN105949241A (zh) | 一种噁唑烷酮类抗菌药物钠盐的晶型a及其制备方法和应用 | |
CN105198932B (zh) | 洛铂二水合物、制备方法及药物应用 | |
CN105693793B (zh) | 一种利巴韦林化合物及其药物组合物 | |
CN111620880B (zh) | Pf-06651600 dl-酒石酸盐,晶型及其制备方法 | |
CN104447689B (zh) | 来那度胺的晶型及其制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180726 Address after: 201203 555 Zhangjiang Road, Zhangjiang, Pudong New Area, Shanghai Patentee after: Shanghai Institute of Materia Medica, Chinese Academy of Sciences Address before: 322118 Jiangnan Road, Hengdian Industrial Zone, Dongyang, Jinhua, Zhejiang 519 Co-patentee before: YOSEMADE PHARMACEUTICAL CO., LTD. Patentee before: Zhejiang Puluo Debang Pharmaceutical Co., Ltd. |
|
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180417 Termination date: 20180909 |