NO323459B1 - (S)-N[[3-[3-fluor-4-(morfolinyl)fenyl]-2-okso-5-oksazolidinyl]metyl]acetamid ,krystall form II - Google Patents
(S)-N[[3-[3-fluor-4-(morfolinyl)fenyl]-2-okso-5-oksazolidinyl]metyl]acetamid ,krystall form II Download PDFInfo
- Publication number
- NO323459B1 NO323459B1 NO20023654A NO20023654A NO323459B1 NO 323459 B1 NO323459 B1 NO 323459B1 NO 20023654 A NO20023654 A NO 20023654A NO 20023654 A NO20023654 A NO 20023654A NO 323459 B1 NO323459 B1 NO 323459B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- phenyl
- oxo
- fluoro
- acetamide
- Prior art date
Links
- 239000013078 crystal Chemical group 0.000 title claims description 21
- TYZROVQLWOKYKF-UHFFFAOYSA-N N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide Chemical group O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-UHFFFAOYSA-N 0.000 title 1
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims description 49
- 229960003907 linezolid Drugs 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000001228 spectrum Methods 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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
- 239000008096 xylene Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 5
- 238000002329 infrared spectrum 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
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000000428 dust Substances 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000006104 solid solution Substances 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
- 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
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 (3)
| Publication Number | Publication Date |
|---|---|
| NO20023654L NO20023654L (no) | 2002-08-01 |
| NO20023654D0 NO20023654D0 (no) | 2002-08-01 |
| NO323459B1 true NO323459B1 (no) | 2007-05-14 |
Family
ID=22658183
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20023654A NO323459B1 (no) | 2000-02-02 | 2002-08-01 | (S)-N[[3-[3-fluor-4-(morfolinyl)fenyl]-2-okso-5-oksazolidinyl]metyl]acetamid ,krystall form II |
| NO20065836A NO20065836L (no) | 2000-02-02 | 2006-12-15 | Linezolidkrystallform |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20065836A NO20065836L (no) | 2000-02-02 | 2006-12-15 | Linezolidkrystallform |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP1255754B1 (es) |
| JP (1) | JP5235256B2 (es) |
| KR (3) | KR100864745B1 (es) |
| CN (1) | CN1221547C (es) |
| AR (1) | AR027261A1 (es) |
| AT (1) | ATE297920T1 (es) |
| AU (1) | AU782138B2 (es) |
| BR (1) | BR0107667A (es) |
| CA (1) | CA2395603C (es) |
| CO (1) | CO5261555A1 (es) |
| CZ (1) | CZ302292B6 (es) |
| DE (1) | DE60111497T2 (es) |
| DK (1) | DK1255754T3 (es) |
| EA (1) | EA004434B1 (es) |
| EE (1) | EE05197B1 (es) |
| ES (1) | ES2242728T3 (es) |
| HK (1) | HK1051196A1 (es) |
| HU (1) | HUP0301076A3 (es) |
| IL (1) | IL151010A0 (es) |
| MX (1) | MXPA02007471A (es) |
| MY (1) | MY122829A (es) |
| NO (2) | NO323459B1 (es) |
| NZ (1) | NZ520541A (es) |
| PE (1) | PE20011086A1 (es) |
| PL (1) | PL356433A1 (es) |
| PT (1) | PT1255754E (es) |
| SI (1) | SI1255754T1 (es) |
| SK (1) | SK287025B6 (es) |
| TW (1) | TWI297687B (es) |
| WO (1) | WO2001057035A1 (es) |
| ZA (1) | ZA200205162B (es) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100490643B1 (ko) * | 2002-10-29 | 2005-05-19 | 한국과학기술연구원 | 새로운 메틸리덴 피페리딘일 옥사졸리딘온 유도체 및이들의 제조방법 |
| EP2100884A1 (en) | 2003-10-16 | 2009-09-16 | Symed Labs Limited | Crystalline form of linezolid |
| DE602004009344T2 (de) | 2004-04-19 | 2008-07-10 | Symed Labs Ltd., Hyderabad | Neues verfahren zur herstellung von linezolid und verwandten verbindungen |
| JP2007504173A (ja) * | 2004-06-29 | 2007-03-01 | 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 | リネゾリドのｉｖ型結晶 |
| WO2006110155A1 (en) * | 2004-06-29 | 2006-10-19 | Teva Pharmaceutical Industries Ltd | Solid forms of linezolid and processes for preparation thereof |
| CA2602073A1 (en) | 2005-02-24 | 2006-08-31 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of linezolid intermediate |
| MX2007002113A (es) * | 2005-06-22 | 2007-04-27 | Teva Pharma | Formas polimorfas de maleato de tegaserod. |
| CA2612481A1 (en) * | 2005-07-20 | 2007-02-15 | Teva Pharmaceutical Industries Ltd. | Stable pharmaceutical composition comprising linezolid form iv |
| WO2007102082A1 (en) * | 2006-03-09 | 2007-09-13 | Glenmark Pharmaceuticals Limited | High oxazolidinone content solid dosage forms |
| EP2099299A4 (en) * | 2006-10-23 | 2011-11-30 | Concert Pharmaceuticals Inc | OXAZOLIDINONE DERIVATIVES AND METHOD FOR THEIR USE |
| WO2011050826A1 (en) | 2009-10-28 | 2011-05-05 | Synthon B.V. | Process for making crystalline form a of linezolid |
| BR112012027901A2 (pt) | 2010-04-30 | 2015-09-08 | Univ Indiana Res & Tech Corp | processos para preparar linezolida |
| EP2690100A1 (en) | 2010-08-11 | 2014-01-29 | Synhton B.V. | Process for making linezolid |
| CN103140487A (zh) | 2010-08-11 | 2013-06-05 | 斯索恩有限公司 | 制备利奈唑胺的方法 |
| WO2012114354A1 (en) * | 2011-02-24 | 2012-08-30 | Lee Pharma Limited | Anhydrous linezolid crystalline form-ii |
| EP2683696A1 (en) | 2011-03-09 | 2014-01-15 | 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 |
| US20150025236A1 (en) | 2012-01-24 | 2015-01-22 | Jubilant Life Sciences Limited | 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 |
| EP2917189B1 (en) | 2012-11-09 | 2016-08-17 | Synthon BV | Process for making linezolid |
| US11517574B2 (en) * | 2017-11-16 | 2022-12-06 | 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 |
| US5688792A (en) * | 1994-08-16 | 1997-11-18 | Pharmacia & Upjohn Company | Substituted oxazine and thiazine oxazolidinone antimicrobials |
| MY115155A (en) * | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| JP2000508312A (ja) * | 1996-04-11 | 2000-07-04 | ファルマシア・アンド・アップジョン・カンパニー | オキサゾリジノンの製法 |
| KR100619639B1 (ko) * | 1997-11-07 | 2006-09-06 | 파마시아 앤드 업존 캄파니 엘엘씨 | 옥사졸리디논의 제조 방법 |
-
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 SI SI200130405T patent/SI1255754T1/sl unknown
- 2001-01-29 DE DE60111497T patent/DE60111497T2/de not_active Expired - Lifetime
- 2001-01-29 EE EEP200200420A patent/EE05197B1/xx not_active IP Right Cessation
- 2001-01-29 ES ES01904805T patent/ES2242728T3/es not_active Expired - Lifetime
- 2001-01-29 JP JP2001557867A patent/JP5235256B2/ja not_active Expired - Lifetime
- 2001-01-29 PL PL01356433A patent/PL356433A1/xx unknown
- 2001-01-29 MY MYPI20010371A patent/MY122829A/en unknown
- 2001-01-29 KR KR1020077016678A patent/KR100864745B1/ko not_active IP Right Cessation
- 2001-01-29 BR BR0107667-1A patent/BR0107667A/pt not_active Application Discontinuation
- 2001-01-29 IL IL15101001A patent/IL151010A0/xx active IP Right Grant
- 2001-01-29 CN CNB018034489A patent/CN1221547C/zh not_active Expired - Fee Related
- 2001-01-29 AU AU32755/01A patent/AU782138B2/en not_active Ceased
- 2001-01-29 PT PT01904805T patent/PT1255754E/pt unknown
- 2001-01-29 NZ NZ520541A patent/NZ520541A/en not_active IP Right Cessation
- 2001-01-29 HU HU0301076A patent/HUP0301076A3/hu unknown
- 2001-01-29 DK DK01904805T patent/DK1255754T3/da active
- 2001-01-29 KR KR1020027009923A patent/KR100781815B1/ko not_active IP Right Cessation
- 2001-01-29 MX MXPA02007471A patent/MXPA02007471A/es active IP Right Grant
- 2001-01-29 EA EA200200819A patent/EA004434B1/ru not_active IP Right Cessation
- 2001-01-29 AT AT01904805T patent/ATE297920T1/de active
- 2001-01-29 WO PCT/US2001/000657 patent/WO2001057035A1/en active IP Right Grant
- 2001-01-29 SK SK994-2002A patent/SK287025B6/sk not_active IP Right Cessation
- 2001-01-29 KR KR1020087010742A patent/KR20080044358A/ko not_active Application Discontinuation
- 2001-01-29 CA CA2395603A patent/CA2395603C/en not_active Expired - Lifetime
- 2001-01-29 CZ CZ20022635A patent/CZ302292B6/cs not_active IP Right Cessation
- 2001-01-29 EP EP01904805A patent/EP1255754B1/en not_active Expired - Lifetime
- 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
-
2003
- 2003-05-16 HK HK03103460A patent/HK1051196A1/xx not_active IP Right Cessation
-
2006
- 2006-12-15 NO NO20065836A patent/NO20065836L/no not_active Application Discontinuation
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| MM1K | Lapsed by not paying the annual fees |