AR035511A1 - Procedimiento para preparar una cefalosporina e intermediarios de sintesis - Google Patents
Procedimiento para preparar una cefalosporina e intermediarios de sintesisInfo
- Publication number
- AR035511A1 AR035511A1 ARP010105609A ARP010105609A AR035511A1 AR 035511 A1 AR035511 A1 AR 035511A1 AR P010105609 A ARP010105609 A AR P010105609A AR P010105609 A ARP010105609 A AR P010105609A AR 035511 A1 AR035511 A1 AR 035511A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- aryl
- formula
- carboxylate
- mono
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- HOKIDJSKDBPKTQ-UHFFFAOYSA-N 3-(acetyloxymethyl)-7-[(5-amino-5-carboxypentanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 HOKIDJSKDBPKTQ-UHFFFAOYSA-N 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 14
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 5
- 150000007942 carboxylates Chemical class 0.000 abstract 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- -1 carboxylate salt Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 125000001271 cephalosporin group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000007822 coupling agent Substances 0.000 abstract 1
- 150000004292 cyclic ethers Chemical group 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000006502 nitrobenzyl group Chemical group 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
- C07D501/06—Acylation of 7-aminocephalosporanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Un procedimiento para preparar una cefalosporina sustituida con un éter cíclico en la posición 3 de fórmula (1) o una de las sales farmacéuticamente aceptables de la misma, en la que el grupo CO2R1 es un ácido carboxílico o una sal carboxilato; y R2 tiene una fórmula (2) en la que A1 se selecciona del grupo formado por arilo C6-10, heteroarilo C1-10 y heterociclilo C1-10; A2 se selecciona del grupo formado por hidrógeno, alquilo C1-6, cicloalquilo C3-10, arilo C6-10, (alquil C1-6)(CO)(alquil C1-6)-O-, HO(CO)(alquilo C1-6), mono(aril C6-10)(alquilo C1-6), di-(aril C6-10)(alquilo C1-6) y tri-(aril C6-10)(alquilo C1-6); que comprende hacer reaccionar un compuesto de fórmula (3) con un compuesto de fórmula (4): R2L en la que R2 es como se ha definido antes; y L se selecciona del grupo formado por hidroxilo, halo, azido, mono(alquil C1-6) carbonato, (alquil C1-6) carboxilato, (aril C6-10) carboxilato, mono- (aril C6-10)(alquil C1-6) carboxilato, di-(aril C6-10)(alquil C1-6)carboxilato, di-(alquil C1-6) fosforotioato, (alquil C1-6) sulfonilo, mono- (alquil C1-6)(aril C6-10) sulfonilo, di-(alquil C1-6)(aril C6-10)sulfonilo, (alquil C1-6)-(CO)-S-, ciano-alcoxi C1-6, ariloxi C6-10, 3-benzotiazoliloxi, 8-quinoliniloxi y N-oxi-succinimidilo; en presencia de un disolvente, una base, un agente de acoplamiento opcional y un catalizador opcional. Se describe también otro procedimiento para preparar el compuesto de fórmula (1), que comprende hacer reaccionar un compuesto de fórmula (5), en la que R2 es como se ha definido antes; y R3 es para nitrobencilo o alilo; con un agente de desprotección adecuado en presencia de un disolvente. Se describen también dos intermediarios (3) y (5) según se describió anteriormente. Estos compuestos tienen niveles prolongados y elevados de actualidad antibacteriana y poseen buena absorción parenteral en seres humanos y animales.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25101400P | 2000-12-04 | 2000-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR035511A1 true AR035511A1 (es) | 2004-06-02 |
Family
ID=22950114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP010105609A AR035511A1 (es) | 2000-12-04 | 2001-12-03 | Procedimiento para preparar una cefalosporina e intermediarios de sintesis |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US20020198375A1 (es) |
| EP (1) | EP1339722A1 (es) |
| JP (1) | JP2004520293A (es) |
| KR (1) | KR100526379B1 (es) |
| CN (1) | CN1243755C (es) |
| AR (1) | AR035511A1 (es) |
| AU (2) | AU2002223943B2 (es) |
| BR (1) | BR0115870A (es) |
| CA (1) | CA2436848C (es) |
| CZ (1) | CZ20031525A3 (es) |
| HU (1) | HUP0400642A3 (es) |
| IL (1) | IL155714A0 (es) |
| MX (1) | MXPA03004937A (es) |
| PL (1) | PL362144A1 (es) |
| RU (1) | RU2237670C1 (es) |
| WO (1) | WO2002046198A1 (es) |
| ZA (1) | ZA200303670B (es) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002046175A1 (en) * | 2000-12-04 | 2002-06-13 | Fujisawa Pharmaceutical Co., Ltd. | Process for producing anhydride of aminothiazole derivative |
| US7378408B2 (en) * | 2001-11-30 | 2008-05-27 | Pfizer Inc. | Methods of treatment and formulations of cephalosporin |
| AU2005225626B2 (en) * | 2004-03-09 | 2008-03-13 | Pfizer Products Inc. | Process for preparing cephalosporin intermediates using alpha-iodo-1-azetidineacetic acid esters and trialkylphosphites |
| CN103797053B (zh) | 2011-05-04 | 2017-06-20 | 康奈尔大学 | 多嵌段共聚物膜及其制备方法和用途 |
| CN103874697A (zh) | 2011-08-03 | 2014-06-18 | 协和发酵麒麟株式会社 | 二苯并氧杂*衍生物 |
| CN102718779B (zh) * | 2012-05-25 | 2015-07-29 | 深圳致君制药有限公司 | 注射用头孢唑肟钠及其制备方法、原料药头孢唑肟钠的合成方法 |
| CN105254648B (zh) * | 2015-11-13 | 2018-04-03 | 广东温氏大华农生物科技有限公司 | 一种头孢维星及其钠盐的合成方法 |
| WO2018229580A1 (en) * | 2017-06-14 | 2018-12-20 | Aurobindo Pharma Ltd | An improved process for the preparation of cefovecin sodium |
| SG11202002333SA (en) | 2017-09-19 | 2020-04-29 | Terapore Tech Inc | Chemically resistant isoporous crosslinked block copolymer structure |
| JP7495353B2 (ja) * | 2018-04-04 | 2024-06-04 | テラポア テクノロジーズ，インコーポレイテッド | カプセル化粒子分画装置、それらのシステム及び使用方法 |
| US11051804B2 (en) * | 2018-07-02 | 2021-07-06 | DePuy Synthes Products, Inc. | Orthopedic fixation system and method of use thereof |
| GB2575261B (en) | 2018-07-02 | 2022-03-09 | Norbrook Lab Ltd | Intermediates in the synthesis of C3-substituted cephalosporins |
| CN110396034A (zh) * | 2019-07-31 | 2019-11-01 | 上海应用技术大学 | 一种烯丙基化合物的制备方法 |
| CN111187284A (zh) * | 2020-03-10 | 2020-05-22 | 赵俊瑶 | 一种头孢克洛的制备方法 |
| CN111892612A (zh) * | 2020-07-31 | 2020-11-06 | 重庆医药高等专科学校 | 一种以青霉素钾盐为原料制备头孢维星的中间体异构化物及其制备方法 |
| CN112321611B (zh) * | 2020-10-29 | 2022-05-06 | 湖北凌晟药业有限公司 | 一种头孢沙定母核的制备方法 |
| CN115873021A (zh) * | 2022-12-19 | 2023-03-31 | 华北制药集团动物保健品有限责任公司 | 一种头孢维星钠的制备方法 |
| CN116731039B (zh) * | 2023-06-12 | 2025-02-18 | 重庆汉佩生物科技有限公司 | 头孢维星衍生物的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY106399A (en) * | 1990-07-24 | 1995-05-30 | Pfizer | Cephalosporins and homologeus, preparation and pharmaceutical composition |
| US6001997A (en) * | 1990-07-24 | 1999-12-14 | Bateson; John Hargreaves | Cephalosporins and homologues, preparations and pharmaceutical compositions |
| GB9212609D0 (en) * | 1992-06-13 | 1992-07-29 | Smithkline Beecham Plc | Novel compounds |
| GB9424847D0 (en) * | 1994-12-09 | 1995-02-08 | Smithkline Beecham Plc | Novel process |
| GB2300856A (en) * | 1995-05-16 | 1996-11-20 | Pfizer Ltd | Beta-lactam preparation |
| GB0019124D0 (en) * | 2000-08-03 | 2000-09-27 | Pfizer | Novel process |
| DE60117876T2 (de) * | 2000-12-04 | 2006-08-31 | Pfizer Products Inc., Groton | Verfahren und esterderivate zur herstellung von cephalosphorinen |
-
2001
- 2001-11-22 HU HU0400642A patent/HUP0400642A3/hu unknown
- 2001-11-22 EP EP01999227A patent/EP1339722A1/en not_active Withdrawn
- 2001-11-22 WO PCT/IB2001/002225 patent/WO2002046198A1/en not_active Ceased
- 2001-11-22 BR BR0115870-8A patent/BR0115870A/pt not_active IP Right Cessation
- 2001-11-22 CA CA002436848A patent/CA2436848C/en not_active Expired - Fee Related
- 2001-11-22 PL PL01362144A patent/PL362144A1/xx not_active Application Discontinuation
- 2001-11-22 JP JP2002547935A patent/JP2004520293A/ja active Pending
- 2001-11-22 AU AU2002223943A patent/AU2002223943B2/en not_active Ceased
- 2001-11-22 MX MXPA03004937A patent/MXPA03004937A/es active IP Right Grant
- 2001-11-22 CZ CZ20031525A patent/CZ20031525A3/cs unknown
- 2001-11-22 KR KR10-2003-7007396A patent/KR100526379B1/ko not_active Expired - Fee Related
- 2001-11-22 AU AU2394302A patent/AU2394302A/xx active Pending
- 2001-11-22 RU RU2003116519/04A patent/RU2237670C1/ru active
- 2001-11-22 CN CNB018199623A patent/CN1243755C/zh not_active Expired - Fee Related
- 2001-11-22 IL IL15571401A patent/IL155714A0/xx unknown
- 2001-12-03 AR ARP010105609A patent/AR035511A1/es not_active Application Discontinuation
- 2001-12-04 US US10/006,279 patent/US20020198375A1/en not_active Abandoned
-
2003
- 2003-05-13 ZA ZA200303670A patent/ZA200303670B/en unknown
-
2004
- 2004-02-11 US US10/776,795 patent/US7129350B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2436848C (en) | 2008-12-02 |
| US20020198375A1 (en) | 2002-12-26 |
| IL155714A0 (en) | 2003-11-23 |
| AU2002223943B2 (en) | 2006-10-05 |
| PL362144A1 (en) | 2004-10-18 |
| AU2394302A (en) | 2002-06-18 |
| HK1059435A1 (en) | 2004-07-02 |
| CN1243755C (zh) | 2006-03-01 |
| CZ20031525A3 (cs) | 2004-04-14 |
| WO2002046198A1 (en) | 2002-06-13 |
| HUP0400642A3 (en) | 2010-03-29 |
| BR0115870A (pt) | 2004-02-03 |
| US7129350B2 (en) | 2006-10-31 |
| RU2237670C1 (ru) | 2004-10-10 |
| JP2004520293A (ja) | 2004-07-08 |
| CN1478093A (zh) | 2004-02-25 |
| KR20030070043A (ko) | 2003-08-27 |
| HUP0400642A2 (hu) | 2004-06-28 |
| MXPA03004937A (es) | 2003-09-10 |
| KR100526379B1 (ko) | 2005-11-08 |
| ZA200303670B (en) | 2004-05-13 |
| EP1339722A1 (en) | 2003-09-03 |
| US20040167327A1 (en) | 2004-08-26 |
| CA2436848A1 (en) | 2002-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC | Refusal | ||
| FB | Suspension of granting procedure |