SK287025B6 - Linezolid - kryštalická forma II a spôsob jeho prípravy - Google Patents
Linezolid - kryštalická forma II a spôsob jeho prípravy Download PDFInfo
- Publication number
- SK287025B6 SK287025B6 SK994-2002A SK9942002A SK287025B6 SK 287025 B6 SK287025 B6 SK 287025B6 SK 9942002 A SK9942002 A SK 9942002A SK 287025 B6 SK287025 B6 SK 287025B6
- Authority
- SK
- Slovakia
- Prior art keywords
- solvent
- methyl
- phenyl
- oxazolidinyl
- morpholinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000013078 crystal Substances 0.000 title abstract description 9
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims abstract description 56
- 229960003907 linezolid Drugs 0.000 claims abstract description 39
- 239000002904 solvent Substances 0.000 claims description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 239000002362 mulch Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims 6
- 239000003242 anti bacterial agent Substances 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17983700P | 2000-02-02 | 2000-02-02 | |
| PCT/US2001/000657 WO2001057035A1 (en) | 2000-02-02 | 2001-01-29 | Linezolid-crystal form ii |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK9942002A3 SK9942002A3 (en) | 2002-11-06 |
| SK287025B6 true SK287025B6 (sk) | 2009-10-07 |
Family
ID=22658183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK994-2002A SK287025B6 (sk) | 2000-02-02 | 2001-01-29 | Linezolid - kryštalická forma II a spôsob jeho prípravy |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1255754B1 (enExample) |
| JP (1) | JP5235256B2 (enExample) |
| KR (3) | KR100781815B1 (enExample) |
| CN (1) | CN1221547C (enExample) |
| AR (1) | AR027261A1 (enExample) |
| AT (1) | ATE297920T1 (enExample) |
| AU (1) | AU782138B2 (enExample) |
| BR (1) | BR0107667A (enExample) |
| CA (1) | CA2395603C (enExample) |
| CO (1) | CO5261555A1 (enExample) |
| CZ (1) | CZ302292B6 (enExample) |
| DE (1) | DE60111497T2 (enExample) |
| DK (1) | DK1255754T3 (enExample) |
| EA (1) | EA004434B1 (enExample) |
| EE (1) | EE05197B1 (enExample) |
| ES (1) | ES2242728T3 (enExample) |
| HU (1) | HUP0301076A3 (enExample) |
| IL (1) | IL151010A0 (enExample) |
| MX (1) | MXPA02007471A (enExample) |
| MY (1) | MY122829A (enExample) |
| NO (2) | NO323459B1 (enExample) |
| NZ (1) | NZ520541A (enExample) |
| PE (1) | PE20011086A1 (enExample) |
| PL (1) | PL356433A1 (enExample) |
| PT (1) | PT1255754E (enExample) |
| SI (1) | SI1255754T1 (enExample) |
| SK (1) | SK287025B6 (enExample) |
| TW (1) | TWI297687B (enExample) |
| WO (1) | WO2001057035A1 (enExample) |
| ZA (1) | ZA200205162B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100490643B1 (ko) * | 2002-10-29 | 2005-05-19 | 한국과학기술연구원 | 새로운 메틸리덴 피페리딘일 옥사졸리딘온 유도체 및이들의 제조방법 |
| ES2803516T3 (es) | 2003-10-16 | 2021-01-27 | Symed Labs Ltd | Una forma cristalina de linezolid |
| ES2294494T3 (es) | 2004-04-19 | 2008-04-01 | Symed Labs Limited | Un nuevo procedimiento para la preparacion de linezolid y compuestos relacionados. |
| EP1658275A1 (en) * | 2004-06-29 | 2006-05-24 | Teva Pharmaceutical Industries Ltd | Crystalline form iv of linezolid |
| EP1745028A2 (en) * | 2004-06-29 | 2007-01-24 | Teva Pharmaceutical Industries Ltd | Solid forms of linezolid and processes for preparation thereof |
| WO2006091731A2 (en) * | 2005-02-24 | 2006-08-31 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of linezolid intermediate |
| KR20070062504A (ko) * | 2005-06-22 | 2007-06-15 | 테바 파마슈티컬 인더스트리즈 리미티드 | 테가세로드 말레이트의 다형태 |
| DK1749517T3 (da) * | 2005-07-20 | 2008-11-03 | Teva Pharma | Stabil farmaceutiske sammensætning af linezolid form IV |
| WO2007102082A1 (en) * | 2006-03-09 | 2007-09-13 | Glenmark Pharmaceuticals Limited | High oxazolidinone content solid dosage forms |
| WO2008127300A2 (en) * | 2006-10-23 | 2008-10-23 | Concert Pharmaceuticals Inc. | Oxazolidinone derivatives and methods of use |
| WO2011050826A1 (en) | 2009-10-28 | 2011-05-05 | Synthon B.V. | Process for making crystalline form a of linezolid |
| CN103025730A (zh) | 2010-04-30 | 2013-04-03 | 印第安纳大学研究及科技有限公司 | 制备利奈唑胺的方法 |
| EP2690100A1 (en) | 2010-08-11 | 2014-01-29 | Synhton B.V. | Process for making linezolid |
| WO2012019632A1 (en) | 2010-08-11 | 2012-02-16 | Synthon B.V. | Process for making linezolid |
| EP2593440A1 (en) * | 2011-02-24 | 2013-05-22 | Lee Pharma Limited | Anhydrous linezolid crystalline form-ii |
| WO2012119653A1 (en) | 2011-03-09 | 2012-09-13 | Synthon Bv | Process for making crystalline form a of linezolid |
| CN102731341A (zh) * | 2011-04-13 | 2012-10-17 | 上海医药工业研究院 | 用于制备利奈唑胺的中间体及其制备方法 |
| CN105461648B (zh) * | 2011-05-03 | 2018-01-12 | 江苏豪森药业集团有限公司 | 利奈唑胺的晶型及其制备方法 |
| CN102399200B (zh) * | 2011-12-14 | 2013-12-04 | 浙江新东港药业股份有限公司 | 一种利用悬浮结晶法制备利奈唑胺晶型ⅰ的方法 |
| WO2013111048A1 (en) | 2012-01-24 | 2013-08-01 | Jubilant Life Sciences Limited | Improved process for the preparation of stable crystalline form-i of linezolid, substantially free of residual solvent |
| WO2013120496A1 (en) | 2012-02-14 | 2013-08-22 | Pharmathen S.A. | Process for the preparation of linezolid in crystalline form and salts thereof |
| CN102643245A (zh) * | 2012-04-10 | 2012-08-22 | 杭州华东医药集团生物工程研究所有限公司 | 一种利奈唑胺晶型及其制备方法 |
| ES2603252T3 (es) | 2012-11-09 | 2017-02-24 | Synthon Bv | Proceso para preparar linezolid |
| US20190343761A1 (en) | 2016-11-16 | 2019-11-14 | Persica Pharmaceuticals Ltd. | Antibiotic formulations for lower back pain |
| EP3709970B1 (en) * | 2017-11-16 | 2025-05-14 | Persica Pharmaceuticals Ltd. | Linezolid formulations |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK283420B6 (sk) * | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
| MY115155A (en) * | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| US5688792A (en) * | 1994-08-16 | 1997-11-18 | Pharmacia & Upjohn Company | Substituted oxazine and thiazine oxazolidinone antimicrobials |
| SG85683A1 (en) * | 1996-04-11 | 2002-01-15 | Upjohn Co | Process to prepare oxazolidinones |
| NZ504372A (en) * | 1997-11-07 | 2002-12-20 | Upjohn Co | Process to produce N-[3-fluoro-4(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinones |
-
2001
- 2001-01-22 AR ARP010100269A patent/AR027261A1/es not_active Application Discontinuation
- 2001-01-25 PE PE2001000080A patent/PE20011086A1/es not_active Application Discontinuation
- 2001-01-26 CO CO01005901A patent/CO5261555A1/es not_active Application Discontinuation
- 2001-01-29 JP JP2001557867A patent/JP5235256B2/ja not_active Expired - Lifetime
- 2001-01-29 AT AT01904805T patent/ATE297920T1/de active
- 2001-01-29 BR BR0107667-1A patent/BR0107667A/pt not_active Application Discontinuation
- 2001-01-29 NZ NZ520541A patent/NZ520541A/en not_active IP Right Cessation
- 2001-01-29 MX MXPA02007471A patent/MXPA02007471A/es active IP Right Grant
- 2001-01-29 WO PCT/US2001/000657 patent/WO2001057035A1/en not_active Ceased
- 2001-01-29 ES ES01904805T patent/ES2242728T3/es not_active Expired - Lifetime
- 2001-01-29 EA EA200200819A patent/EA004434B1/ru not_active IP Right Cessation
- 2001-01-29 DE DE60111497T patent/DE60111497T2/de not_active Expired - Lifetime
- 2001-01-29 HU HU0301076A patent/HUP0301076A3/hu unknown
- 2001-01-29 AU AU32755/01A patent/AU782138B2/en not_active Ceased
- 2001-01-29 PT PT01904805T patent/PT1255754E/pt unknown
- 2001-01-29 EP EP01904805A patent/EP1255754B1/en not_active Expired - Lifetime
- 2001-01-29 CA CA2395603A patent/CA2395603C/en not_active Expired - Lifetime
- 2001-01-29 KR KR1020027009923A patent/KR100781815B1/ko not_active Expired - Fee Related
- 2001-01-29 DK DK01904805T patent/DK1255754T3/da active
- 2001-01-29 KR KR1020087010742A patent/KR20080044358A/ko not_active Ceased
- 2001-01-29 EE EEP200200420A patent/EE05197B1/xx not_active IP Right Cessation
- 2001-01-29 IL IL15101001A patent/IL151010A0/xx active IP Right Grant
- 2001-01-29 CZ CZ20022635A patent/CZ302292B6/cs not_active IP Right Cessation
- 2001-01-29 CN CNB018034489A patent/CN1221547C/zh not_active Expired - Fee Related
- 2001-01-29 MY MYPI20010371A patent/MY122829A/en unknown
- 2001-01-29 SK SK994-2002A patent/SK287025B6/sk not_active IP Right Cessation
- 2001-01-29 PL PL01356433A patent/PL356433A1/xx unknown
- 2001-01-29 KR KR1020077016678A patent/KR100864745B1/ko not_active Expired - Fee Related
- 2001-01-29 SI SI200130405T patent/SI1255754T1/sl unknown
- 2001-02-02 TW TW090102231A patent/TWI297687B/zh not_active IP Right Cessation
-
2002
- 2002-06-27 ZA ZA200205162A patent/ZA200205162B/en unknown
- 2002-08-01 NO NO20023654A patent/NO323459B1/no not_active IP Right Cessation
-
2006
- 2006-12-15 NO NO20065836A patent/NO20065836L/no not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SPCF | Filing of an spc |
Free format text: PRODUCT NAME: LINEZOLID; NAT. REGISTRATION NO/DATE: 15/0358/00-S - 15/0361/00-S 20001215; FIRST REGISTRATION: GB PL 00032/0259 20010105 Spc suppl protection certif: 5001-2010 Filing date: 20100208 |
|
| SPCR | Rejection of an spc |
Free format text: PRODUCT NAME: LINEZOLID; NAT. REGISTRATION NO/DATE: 15/0358/00-S 15/0359/00-S 15/0360/00-S 15/0361/00-S 20001215 Spc suppl protection certif: 5001-2010 Filing date: 20100208 |
|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20120129 |