TWI297687B - Linezolid-crystal form ii - Google Patents
Linezolid-crystal form ii Download PDFInfo
- Publication number
- TWI297687B TWI297687B TW090102231A TW90102231A TWI297687B TW I297687 B TWI297687 B TW I297687B TW 090102231 A TW090102231 A TW 090102231A TW 90102231 A TW90102231 A TW 90102231A TW I297687 B TWI297687 B TW I297687B
- Authority
- TW
- Taiwan
- Prior art keywords
- solvent
- phenyl
- fluoro
- acetamide
- methyl
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 claims description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 12
- 239000002904 solvent Substances 0.000 claims 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 239000011877 solvent mixture Substances 0.000 claims 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 claims 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 239000002480 mineral oil Substances 0.000 claims 1
- 235000010446 mineral oil Nutrition 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 230000000242 pagocytic effect Effects 0.000 claims 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 210000003296 saliva Anatomy 0.000 claims 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 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
- 238000013019 agitation Methods 0.000 description 1
- 238000003339 best practice Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000000376 reactant Substances 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17983700P | 2000-02-02 | 2000-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI297687B true TWI297687B (en) | 2008-06-11 |
Family
ID=22658183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090102231A TWI297687B (en) | 2000-02-02 | 2001-02-02 | Linezolid-crystal form ii |
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
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI297687B (en) | Linezolid-crystal form ii | |
| ES2803516T3 (es) | Una forma cristalina de linezolid | |
| JP7684409B2 (ja) | 有機スズ化合物を調製する方法 | |
| JP6511346B2 (ja) | ハロゲン化環式化合物の合成方法 | |
| JP7368365B2 (ja) | Ｐ３００／ｃｂｐ ｈａｔ阻害剤及びそれらの使用の方法 | |
| CN107735398A (zh) | 用于合成雷帕霉素衍生物的方法 | |
| JP4328528B2 (ja) | ピペラジン誘導体のメシラートの製造方法 | |
| TWI311135B (en) | Process for producing 2-azetidinone derivative | |
| JP6504530B2 (ja) | 光学活性な２−（２−フルオロビフェニル−４−イル）プロパン酸の製造法 | |
| CN1317265C (zh) | 氰基丙烯酸酯衍生物及制备方法和生物活性 | |
| JPH05194491A (ja) | イミダゾリルメチル−ピリジン | |
| JP3850471B2 (ja) | アリールグリシンから４−アリール−２−ペルフルオロアルキル−３−オキサゾリン−５−オンの製造 | |
| WO1991017979A1 (en) | Process for the preparation of 2-n-acylaminopyridines and 2-aminopyridines from 5-oxoalkanenitrile oximes | |
| JP4538993B2 (ja) | β−ケトニトリル誘導体の製法 | |
| EP1539751A1 (en) | Process for the preparation of imidazo(1,2-a)pyridine-3-acetamides | |
| JP5375288B2 (ja) | ピラゾリン誘導体の製造方法 | |
| CA1085846A (en) | Process for producing 3-substituted 1,2,4-triazines | |
| JPS6335584A (ja) | 珪素の部分エステルハロゲン化物の製造法 | |
| US20090140200A1 (en) | Substituted alkylmetal compositions and methods of preparing the same | |
| JPH0826009B2 (ja) | 選択性除草剤として有用な新規１，２，４―オキサジアゾール誘導体 | |
| CA2008079A1 (en) | Halogenation process | |
| JPH0242822B2 (cg-RX-API-DMAC7.html) | ||
| IL94658A (en) | 1,5-Diazabicyclo [3,3,0] octanediones and pharmaceutical compositions containing them | |
| JP2002308840A (ja) | ３−アリール−３−イミノプロピオン酸エステルの立体選択的還元方法 | |
| Tran | Synthetic applications of silicon Lewis acids: Total synthesis of MS-153 and manzacidin C |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |