AR035830A1 - Proceso para preparar oxazolidinonas e intermediarios usados en dicho proceso - Google Patents
Proceso para preparar oxazolidinonas e intermediarios usados en dicho procesoInfo
- Publication number
- AR035830A1 AR035830A1 ARP020101390A ARP020101390A AR035830A1 AR 035830 A1 AR035830 A1 AR 035830A1 AR P020101390 A ARP020101390 A AR P020101390A AR P020101390 A ARP020101390 A AR P020101390A AR 035830 A1 AR035830 A1 AR 035830A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- aryl
- optionally substituted
- ch3c
- och2c
- Prior art date
Links
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
Abstract
Un proceso para preparar una oxazolidinona de fórmula (1) o una de sus sales, que comprende hacer reaccionar un N-aril-O-alquilcarbamato de fórmula (2) o una de sus sales, con un compuesto de fórmula (3) o una de sus sales, en presencia de catión litio, una base y un nucleófilo, en donde: X e Y son independientemente H o F; W1 es Cl, Br u -OS(O)2-R; W2 es H o -C(O)-R1; R es arilo o alquilo, estando el alquilo sustituido opcionalmente con uno o más F, Cl, Br o I; R1 es CH3, opcionalmente sustituido con entre uno y tres átomos de flúor o cloro; R2 es cicloalquilo, fenilo, -CH2-fenilo, alquenilo C2-6 o alquilo C1-12 opcionalmente sustituido con entre uno y tres F, Br, Cl, -O-alquilo C1-6 y NR2aR2b; cada R2a y R2b es independientemente H o alquilo C1-4; Q es la estructura (4), (5), (6), (7) y (8) o Q y X tomados en conjunto son dihidropirrolidina, opcionalmente sustituida con R5; Z1 es CH2(CH2)p, CH(OH)(CH2)p o C(O); Z2 es S, SO, SO2, O o N(R6); Z3 es S, SO, SO2 u O; R3 es H o CH3; R4 es H, HO, alquilo C1-3, alcoxi C1-4, R7OCH2=C(O)NH-, R8OC(O)NH-, alquilo C1-3-OC(O)-, HOCH2-, CH3ONH, CH3C(O)-, CH3C(O)CH2-, CH3C(OCH2CH2O)- o CH3C(OCH2CH2O)CH2-; R3 y R4 tomados junto con el átomos de carbono al cual se unen forman C(O) o C(=NR9); R5 es: CH3C(O)-, HC(O)-, Cl2CHC(O)-, CHOCH2C(O)-, CH3SO2-, F2CHC(O)-, H3CC(O)OCH2C(O)-, HC(O)OCH2C(O)-, R10C(O)OCH2C(O)-, H3CCHCH2OCH2C(O)- o bencil-OCH2C(O)-; R6 es: H, alquilo C1-6, opcionalmente sustituido con uno o más OH, CN o halo, -(CH2)h-arilo, -COR11, -COOR12, -CO(CH2)h-COR11,-SO2-alquilo C1-6, -SO2-(CH2)h-arilo o -(CO)i-Het; R7 es H, CH3, bencilo o CH3C(O)-; R8 es alquilo C1-3, arilo, o bencilo; R9 es: HO-, CH3O-, H2N-, CH3OC(O)O-, CH3C(O)OCH2C(O)O-, aril-CH2OCH2C(O)O-, HO(CH2)2O-, CH3OCH2O(CH2)2O- o CH3OCH2O-; R10 es: CH3-, HOCH2-, fenil-NH- o (CH3)2-N-CH2-; R11 es: H, alquilo C1-6, opcionalmente sustituido con uno o más OH, CN o halo, -(CH2)h-arilo o -(CH2)h-OR13; R12 es: alquilo C1-6, opcionalmente sustituido con uno o más OH, CN o halo, -(CH2)h-arilo o -(CH2)h-OR13; R13 es: H, alquilo C1-6, -(CH2)h-arilo o -CO(alquilo C1-6);arilo es fenilo, piridilo o naftilo; en cada caso, el arilo o fenilo puede sustituirse opcionalmente con uno o más F, Cl, Br, I, CN, OH, SH, alquilo C1-6, -O-alquilo C1-6 o S-alquilo C1-6, u OC(O)CH3; het representa anillos heterocíclicos de 5 a 10 miembros, que contienen uno o más átomos de oxígeno, nitrógeno y azufre; h es 1, 2, 3 o 4; i es 0 o 1; m es 0 o 1; n es 1, 2 o 3; y p es 0, 1 o 2. También se dan a conocer: un intermediario de fórmula (9) en donde R1 es CHCl2, CHBr2, Cl, CH2Cl, CH2Br, CCl3, CBr3, CHF2, CHF2 o CF3; y un intermediario de fórmula (10) en donde: W3 es -OS(O)2-R; W4 es H o -C(O)-R1; R es arilo o alquilo, estando sustituido opcionalmente el alquilo con uno o más F, Cl, Br o I, y estando sustituido opcionalmente el arilo con uno o más F, Cl, Br, I, CN, OH, NO2, SH, alquilo C1-6, O-alquilo C1-6 o S-alquilo C1-6 u OC(O)CH3; y R1 es CH3, opcionalmente sustituido con entre uno y tres átomos de flúor o cloro. Estos intermediarios son útiles en dicho proceso.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28558601P | 2001-04-20 | 2001-04-20 | |
| US36558102P | 2002-03-19 | 2002-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR035830A1 true AR035830A1 (es) | 2004-07-14 |
Family
ID=26963272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP020101390A AR035830A1 (es) | 2001-04-20 | 2002-04-17 | Proceso para preparar oxazolidinonas e intermediarios usados en dicho proceso |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US6887995B2 (es) |
| EP (1) | EP1380121B1 (es) |
| JP (1) | JP2005504007A (es) |
| AR (1) | AR035830A1 (es) |
| AT (1) | ATE374463T1 (es) |
| AU (1) | AU2002255803B2 (es) |
| CA (1) | CA2440600A1 (es) |
| CY (1) | CY1107003T1 (es) |
| DE (1) | DE60222645T2 (es) |
| DK (1) | DK1380121T3 (es) |
| ES (1) | ES2291465T3 (es) |
| MX (1) | MXPA03009645A (es) |
| MY (1) | MY129372A (es) |
| NZ (1) | NZ528996A (es) |
| PE (1) | PE20021057A1 (es) |
| PT (1) | PT1380121E (es) |
| TW (1) | TWI252229B (es) |
| WO (1) | WO2002085849A2 (es) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2535796A1 (en) * | 2003-08-22 | 2005-03-03 | Pharmacia & Upjohn Company Llc | N-aryl-2-cyanooxazolidinones and their derivatives |
| ES2803516T3 (es) | 2003-10-16 | 2021-01-27 | Symed Labs Ltd | Una forma cristalina de linezolid |
| US7186844B2 (en) * | 2004-01-13 | 2007-03-06 | Mitsubishi Gas Chemical Co., Inc. | Method for producing cyclic carbamate ester |
| CN100369909C (zh) * | 2004-03-23 | 2008-02-20 | 中国科学院上海药物研究所 | N-[4（r）－（1，3－二噁烷基）甲基]苯胺、制备方法和用途 |
| WO2005099353A2 (en) | 2004-04-19 | 2005-10-27 | Symed Labs Limited | A novel process for the preparation of linezolid and related compounds |
| AU2006231919A1 (en) | 2005-04-06 | 2006-10-12 | Pharmacia & Upjohn Company Llc | 7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents |
| EP2033960A3 (en) * | 2007-09-04 | 2009-04-29 | Dipharma Francis S.r.l. | Linezolid crystalline hydrate form and linezolid salts |
| ITMI20072359A1 (it) * | 2007-12-18 | 2009-06-19 | Dipharma Francis Srl | Procedimento per la preparazione di derivati ossazolidinonici |
| EP2163547A1 (en) | 2008-09-16 | 2010-03-17 | Unión Químico Farmacéutica, S.A. (UQUIFA) | Process for the preparation of an oxazolidinone antibacterial agent and intermediates thereof |
| CA2785620A1 (en) * | 2009-12-26 | 2011-06-30 | Alembic Pharmaceuticals Limited | Process for the preparation of linezolid |
| CA2816515A1 (en) | 2010-11-03 | 2012-05-10 | Wockhardt Limited | Process for the preparation of phosphoric acid mono-(1-{4-[(s)-5-(acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2,6-difluorophenyl}-4-methoxymethylpiperidin-4-yl) ester |
| CN102731336B (zh) | 2011-04-12 | 2014-05-07 | 浙江医药股份有限公司新昌制药厂 | 利奈唑胺中间体及合成利奈唑胺的方法 |
| CN102267955A (zh) * | 2011-06-02 | 2011-12-07 | 山东鲁抗医药股份有限公司 | 一种利奈唑胺的制备方法 |
| CN103130733B (zh) * | 2011-12-02 | 2015-07-01 | 重庆圣华曦药业股份有限公司 | 制备利奈唑胺的方法 |
| CN102516191B (zh) * | 2011-12-21 | 2014-03-26 | 吉林省博大伟业制药有限公司 | 一种利奈唑胺的制备方法 |
| CN102977056B (zh) * | 2012-11-28 | 2014-11-26 | 深圳万乐药业有限公司 | N-苄氧羰基-3-氟-4-吗啉基苯胺的合成方法 |
| CN104140399A (zh) * | 2013-05-08 | 2014-11-12 | 江苏豪森药业股份有限公司 | 利奈唑胺的制备方法 |
| CN103483294B (zh) * | 2013-08-12 | 2015-01-28 | 四川大学 | 3-氨基-2-丙醇乙酰胺类化合物的盐、其制备方法和用途 |
| WO2015173664A1 (en) | 2014-05-14 | 2015-11-19 | Wockhardt Limited | Process for the preparation of (5s)-n-{3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide |
| CN105111160B (zh) * | 2015-09-11 | 2017-04-12 | 浙江新东港药业股份有限公司 | 一种利奈唑胺的制备方法 |
| US20170217911A1 (en) * | 2015-12-18 | 2017-08-03 | Mankind Research Centre | Process For Preparation Of Linezolid |
| CN111077248A (zh) * | 2019-12-24 | 2020-04-28 | 江苏乾元生物科技有限公司 | Uplc-ms/ms检测(s)-1-氨基-3-氯-2-丙醇盐酸盐的方法 |
| CN115219632B (zh) * | 2022-07-29 | 2024-04-05 | 山东达因海洋生物制药股份有限公司 | 一种(s)-1-氨基-3-氯-2-丙醇盐酸盐的hplc-elsd检测方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5688792A (en) * | 1994-08-16 | 1997-11-18 | Pharmacia & Upjohn Company | Substituted oxazine and thiazine oxazolidinone antimicrobials |
| JPH10508844A (ja) * | 1994-11-15 | 1998-09-02 | ファルマシア・アンド・アップジョン・カンパニー | 二環式オキサジンおよびチアジンオキサゾリジノン抗菌剤 |
| EP0856002B1 (en) * | 1995-09-01 | 2001-10-24 | PHARMACIA & UPJOHN COMPANY | Phenyloxazolidinones having a c-c bond to 4-8 membered heterocyclic rings |
| MX9703040A (es) * | 1995-09-12 | 1997-07-31 | Upjohn Co | Antimicrobianos de feniloxazolidinona. |
| EP1114819B1 (en) * | 1996-04-11 | 2008-01-09 | Pharmacia & Upjohn Company LLC | Process to prepare oxazolidinones |
| CA2634657A1 (en) | 1997-11-07 | 1999-05-20 | Pharmacia & Upjohn Company | Process to produce oxazolidinones |
| PE20020044A1 (es) | 2000-06-16 | 2002-01-30 | Upjohn Co | Tiazina oxazolidinona |
-
2002
- 2002-04-15 US US10/122,852 patent/US6887995B2/en not_active Expired - Fee Related
- 2002-04-15 JP JP2002583376A patent/JP2005504007A/ja active Pending
- 2002-04-15 CA CA002440600A patent/CA2440600A1/en not_active Abandoned
- 2002-04-15 EP EP02725224A patent/EP1380121B1/en not_active Expired - Lifetime
- 2002-04-15 AT AT02725224T patent/ATE374463T1/de not_active IP Right Cessation
- 2002-04-15 PT PT02725224T patent/PT1380121E/pt unknown
- 2002-04-15 AU AU2002255803A patent/AU2002255803B2/en not_active Ceased
- 2002-04-15 DK DK02725224T patent/DK1380121T3/da active
- 2002-04-15 NZ NZ528996A patent/NZ528996A/en unknown
- 2002-04-15 MX MXPA03009645A patent/MXPA03009645A/es not_active Application Discontinuation
- 2002-04-15 ES ES02725224T patent/ES2291465T3/es not_active Expired - Lifetime
- 2002-04-15 WO PCT/US2002/008261 patent/WO2002085849A2/en active IP Right Grant
- 2002-04-15 DE DE60222645T patent/DE60222645T2/de not_active Expired - Fee Related
- 2002-04-16 PE PE2002000317A patent/PE20021057A1/es not_active Application Discontinuation
- 2002-04-17 AR ARP020101390A patent/AR035830A1/es unknown
- 2002-04-18 MY MYPI20021437A patent/MY129372A/en unknown
- 2002-04-19 TW TW091108112A patent/TWI252229B/zh not_active IP Right Cessation
-
2004
- 2004-03-25 US US10/809,125 patent/US7087784B2/en not_active Expired - Fee Related
-
2007
- 2007-11-13 CY CY20071101463T patent/CY1107003T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE60222645T2 (de) | 2008-07-17 |
| MY129372A (en) | 2007-03-30 |
| WO2002085849A2 (en) | 2002-10-31 |
| NZ528996A (en) | 2006-01-27 |
| EP1380121A2 (en) | 2004-01-14 |
| US7087784B2 (en) | 2006-08-08 |
| TWI252229B (en) | 2006-04-01 |
| PE20021057A1 (es) | 2002-11-27 |
| US20020169312A1 (en) | 2002-11-14 |
| PT1380121E (pt) | 2007-11-21 |
| ATE374463T1 (de) | 2007-10-15 |
| ES2291465T3 (es) | 2008-03-01 |
| DK1380121T3 (da) | 2007-12-27 |
| MXPA03009645A (es) | 2004-01-29 |
| AU2002255803B2 (en) | 2008-07-03 |
| CY1107003T1 (el) | 2012-09-26 |
| US20040220407A1 (en) | 2004-11-04 |
| WO2002085849A3 (en) | 2003-03-06 |
| EP1380121B1 (en) | 2007-09-26 |
| DE60222645D1 (de) | 2007-11-08 |
| US6887995B2 (en) | 2005-05-03 |
| JP2005504007A (ja) | 2005-02-10 |
| CA2440600A1 (en) | 2002-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |