EA004434B1 - Кристаллическая форма ii линезолида - Google Patents
Кристаллическая форма ii линезолида Download PDFInfo
- Publication number
- EA004434B1 EA004434B1 EA200200819A EA200200819A EA004434B1 EA 004434 B1 EA004434 B1 EA 004434B1 EA 200200819 A EA200200819 A EA 200200819A EA 200200819 A EA200200819 A EA 200200819A EA 004434 B1 EA004434 B1 EA 004434B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- methyl
- solvent
- phenyl
- morpholinyl
- acetamide
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 52
- 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 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229960003907 linezolid Drugs 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 5
- 238000001228 spectrum Methods 0.000 claims abstract description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002480 mineral oil Substances 0.000 claims abstract description 3
- 235000010446 mineral oil Nutrition 0.000 claims abstract description 3
- 239000008096 xylene Substances 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 5
- 238000002329 infrared spectrum Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- TYZROVQLWOKYKF-UHFFFAOYSA-N N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide Chemical compound O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 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
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension 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
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation 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
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000003828 vacuum filtration Methods 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 |
|---|---|
| EA200200819A1 EA200200819A1 (ru) | 2003-02-27 |
| EA004434B1 true EA004434B1 (ru) | 2004-04-29 |
Family
ID=22658183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200200819A EA004434B1 (ru) | 2000-02-02 | 2001-01-29 | Кристаллическая форма ii линезолида |
Country Status (30)
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. |
| WO2006110155A1 (en) * | 2004-06-29 | 2006-10-19 | Teva Pharmaceutical Industries Ltd | Solid forms of linezolid and processes for preparation thereof |
| CA2572054A1 (en) * | 2004-06-29 | 2006-01-12 | Teva Pharmaceutical Industries Ltd. | Crystalline form iv of linezolid |
| CA2602073A1 (en) * | 2005-02-24 | 2006-08-31 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of linezolid intermediate |
| JP2008514734A (ja) * | 2005-06-22 | 2008-05-08 | テバ ファーマシューティカル インダストリーズ リミティド | マレイン酸テガセロドの多型体 |
| PL1749517T3 (pl) * | 2005-07-20 | 2008-12-31 | Teva Pharma | Trwała farmaceutyczna kompozycja zawierająca linezolid |
| WO2007102082A1 (en) * | 2006-03-09 | 2007-09-13 | Glenmark Pharmaceuticals Limited | High oxazolidinone content solid dosage forms |
| US20080139563A1 (en) * | 2006-10-23 | 2008-06-12 | 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 |
| JP5865898B2 (ja) | 2010-04-30 | 2016-02-17 | インディアナ ユニバーシティー リサーチ アンド テクノロジー コーポレーションＩｎｄｉａｎａ Ｕｎｉｖｅｒｓｉｔｙ Ｒｅｓｅａｒｃｈ Ａｎｄ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏｒｐｏｒａｔｉｏｎ | リネゾリドを調製するためのプロセス |
| EP2690100A1 (en) | 2010-08-11 | 2014-01-29 | Synhton B.V. | Process for making linezolid |
| EP2603505A1 (en) | 2010-08-11 | 2013-06-19 | Synthon BV | Process for making linezolid |
| CN103402990A (zh) * | 2011-02-24 | 2013-11-20 | 李药业有限公司 | 无水利奈唑胺晶型-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 |
| CN102766106A (zh) * | 2011-05-03 | 2012-11-07 | 江苏豪森医药集团有限公司 | 利奈唑胺的新晶型及其制备方法 |
| 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 |
| IN2014DN06213A (cg-RX-API-DMAC7.html) | 2012-01-24 | 2015-10-23 | Jubilant Life Sciences Ltd | |
| 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 |
| WO2014071990A1 (en) | 2012-11-09 | 2014-05-15 | Synthon Bv | Process for making linezolid |
| KR102615354B1 (ko) | 2016-11-16 | 2023-12-21 | 페르시카 파마슈티컬스 리미티드 | 요통을 위한 항생제 제형 |
| RU2771279C2 (ru) | 2017-11-16 | 2022-04-29 | Персика Фармасьютикалз Лтд. | Композиции линезолида |
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 |
| EE04370B1 (et) * | 1997-11-07 | 2004-10-15 | Pharmacia & Upjohn Company | Oksasolidinoonide valmistamismeetod, meetodis kasutatavad vaheühendid ja nende valmistamine |
-
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 MY MYPI20010371A patent/MY122829A/en unknown
- 2001-01-29 CZ CZ20022635A patent/CZ302292B6/cs not_active IP Right Cessation
- 2001-01-29 DK DK01904805T patent/DK1255754T3/da active
- 2001-01-29 PT PT01904805T patent/PT1255754E/pt unknown
- 2001-01-29 KR KR1020077016678A patent/KR100864745B1/ko not_active Expired - Fee Related
- 2001-01-29 SK SK994-2002A patent/SK287025B6/sk not_active IP Right Cessation
- 2001-01-29 BR BR0107667-1A patent/BR0107667A/pt not_active Application Discontinuation
- 2001-01-29 EA EA200200819A patent/EA004434B1/ru not_active IP Right Cessation
- 2001-01-29 IL IL15101001A patent/IL151010A0/xx active IP Right Grant
- 2001-01-29 DE DE60111497T patent/DE60111497T2/de not_active Expired - Lifetime
- 2001-01-29 JP JP2001557867A patent/JP5235256B2/ja not_active Expired - Lifetime
- 2001-01-29 ES ES01904805T patent/ES2242728T3/es not_active Expired - Lifetime
- 2001-01-29 PL PL01356433A patent/PL356433A1/xx unknown
- 2001-01-29 HU HU0301076A patent/HUP0301076A3/hu unknown
- 2001-01-29 AU AU32755/01A patent/AU782138B2/en not_active Ceased
- 2001-01-29 EP EP01904805A patent/EP1255754B1/en not_active Expired - Lifetime
- 2001-01-29 KR KR1020027009923A patent/KR100781815B1/ko not_active Expired - Fee Related
- 2001-01-29 CA CA2395603A patent/CA2395603C/en not_active Expired - Lifetime
- 2001-01-29 WO PCT/US2001/000657 patent/WO2001057035A1/en not_active Ceased
- 2001-01-29 CN CNB018034489A patent/CN1221547C/zh not_active Expired - Fee Related
- 2001-01-29 EE EEP200200420A patent/EE05197B1/xx not_active IP Right Cessation
- 2001-01-29 SI SI200130405T patent/SI1255754T1/sl unknown
- 2001-01-29 KR KR1020087010742A patent/KR20080044358A/ko not_active Ceased
- 2001-01-29 MX MXPA02007471A patent/MXPA02007471A/es active IP Right Grant
- 2001-01-29 NZ NZ520541A patent/NZ520541A/en not_active IP Right Cessation
- 2001-01-29 AT AT01904805T patent/ATE297920T1/de active
- 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 |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |