PE20090758A1 - Un proceso para la preparacion de compuestos de aminodiol protegidos con oxazolina, utiles como intermediarios para florfenicol - Google Patents

Un proceso para la preparacion de compuestos de aminodiol protegidos con oxazolina, utiles como intermediarios para florfenicol

Info

Publication number
PE20090758A1
PE20090758A1 PE2008000910A PE2008000910A PE20090758A1 PE 20090758 A1 PE20090758 A1 PE 20090758A1 PE 2008000910 A PE2008000910 A PE 2008000910A PE 2008000910 A PE2008000910 A PE 2008000910A PE 20090758 A1 PE20090758 A1 PE 20090758A1
Authority
PE
Peru
Prior art keywords
oxazoline
reaction
compound
preparation
florphenicol
Prior art date
Application number
PE2008000910A
Other languages
English (en)
Inventor
James C Towson
Original Assignee
Schering Plough Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering Plough Ltd filed Critical Schering Plough Ltd
Publication of PE20090758A1 publication Critical patent/PE20090758A1/es

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
    • C07D263/10—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

REFERIDO A UN PROCESO PARA LA PREPARACION DE AMINODIOL PROTEGIDO CON OXAZOLINA DE FORMULA (IV): DONDE R2 ES H, METILO, METILSULFONILO, ENTRE OTROS; R4 S H, ALQUILO C1-C6, DIHALOALQUILO C1-C6, ENTRE OTROS; QUE COMPRENDE A) REACCION DEL COMPUESTO DE FORMULA (V) O UNA SAL DE ADICION DE ACIDO TAL COMO HCL, DONDE R2 ES COMO SE DEFINIO; R3 ES H, ALQUILO(C1-C6), BENCILO(C3-C8), ENTRE OTROS; CON UN REACTIVO PROMOTOR DE AMIDA TAL COMO CARBONATO DE K, PARA FORMAR UN ESTER AMIDA CORRESPONDIENTE; B) REACCION DEL COMPUESTO OBTENIDO CON UN REACTIVO PROMOTOR DE OXAZOLINA TAL COMO CLORURO DE TIONILO PARA FORMAR ESTER OXAZOLINA; C) REACCION DEL COMPUESTO OBETENIDO CON UNA BASE TAL COMO METANOL; D) REACCION DEL COMPUESTO OBTENIDO CON UN AGENTE REDUCTOR TAL COMO NABH4 PARA FORMAR EL COMPUESTO. TAMBIEN SE REFIERE A METODOS DE PREPARACION. DICHO COMPUESTO TIENE ACTIVIDAD ANTIMICROBIANA DE AMPLIO ESPECTRO Y ES UTIL EL LA ELABORACION DE FLORFENICOL Y COMPUESTOS RELACIONADOS
PE2008000910A 2007-05-30 2008-05-28 Un proceso para la preparacion de compuestos de aminodiol protegidos con oxazolina, utiles como intermediarios para florfenicol PE20090758A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US94078607P 2007-05-30 2007-05-30

Publications (1)

Publication Number Publication Date
PE20090758A1 true PE20090758A1 (es) 2009-06-24

Family

ID=39705084

Family Applications (1)

Application Number Title Priority Date Filing Date
PE2008000910A PE20090758A1 (es) 2007-05-30 2008-05-28 Un proceso para la preparacion de compuestos de aminodiol protegidos con oxazolina, utiles como intermediarios para florfenicol

Country Status (16)

Country Link
US (1) US20080319200A1 (es)
EP (1) EP2155702A1 (es)
JP (1) JP2010529016A (es)
KR (1) KR20100022999A (es)
CN (1) CN101784534A (es)
AR (1) AR066748A1 (es)
AU (1) AU2008260595A1 (es)
BR (1) BRPI0812297A2 (es)
CA (1) CA2688432A1 (es)
CL (1) CL2008001562A1 (es)
MX (1) MX2009013016A (es)
PE (1) PE20090758A1 (es)
RU (1) RU2009148864A (es)
TW (1) TW200904783A (es)
WO (1) WO2008150406A1 (es)
ZA (1) ZA200908404B (es)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR044437A1 (es) * 2003-05-29 2005-09-14 Schering Plough Ltd Composiciones y metodo para el tratamiento de infecciones en ganado vacuno y porcino
CA2672795A1 (en) * 2006-12-13 2008-06-26 Schering-Plough Ltd. Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof
CA2732017A1 (en) 2008-07-30 2010-02-04 Intervet International B.V. Process for preparing oxazoline-protected aminodiol compounds useful as intermediates to florfenicol
CA2777741A1 (en) 2009-10-16 2011-04-21 Rib-X Pharmaceuticals, Inc. Antimicrobial compounds and methods of making and using the same
CN102712657A (zh) 2009-10-16 2012-10-03 Rib-X制药公司 抗微生物化合物和其制备和使用方法
WO2012150520A1 (en) 2011-05-02 2012-11-08 Pfizer Inc. Novel cephalosporins useful as antibacterial agents
CN103254103A (zh) * 2013-06-05 2013-08-21 南通金利油脂工业有限公司 氟化剂在制备氟苯尼考工艺中的应用
JP2016529325A (ja) 2013-09-09 2016-09-23 メリンタ セラピューティクス，インコーポレイテッド 抗微生物化合物ならびにそれの製造方法および使用方法
JP2016536338A (ja) 2013-09-09 2016-11-24 メリンタ セラピューティクス，インコーポレイテッド 抗微生物化合物ならびにそれの製造方法および使用方法
CN103980166B (zh) * 2014-04-17 2016-06-22 天津大学 一种氟苯尼考的新晶型及其制备方法
CA2979342A1 (en) 2015-03-11 2016-09-15 Melinta Therapeutics, Inc. Antimicrobial compounds and methods of making and using the same
CN105218474B (zh) * 2015-10-22 2017-12-05 山东国邦药业股份有限公司 (4r,5r)‑2‑二氯甲基‑4,5‑二氢‑5‑(4‑甲砜基苯基)‑4‑恶唑甲醇的合成方法
CA3023317A1 (en) 2016-05-06 2017-11-09 Melinta Therapeutics, Inc. Antimicrobials and methods of making and using same
CN106187837B (zh) * 2016-07-05 2020-03-20 和鼎（南京）医药技术有限公司 一种氟苯尼考中间体、及其制备方法和氟苯尼考的制备方法
CN106631872A (zh) * 2016-12-13 2017-05-10 浙江普洛家园药业有限公司 一种氟苯尼考类似物中间体的合成方法
CN109678811B (zh) * 2019-01-25 2020-12-29 湖北中牧安达药业有限公司 一种氟苯尼考中间体环合物的不对称制备方法
CN110330463B (zh) * 2019-08-02 2021-05-14 山东国邦药业有限公司 一种氟苯尼考中间体的制备方法
CN111285789A (zh) * 2020-03-16 2020-06-16 和鼎（南京）医药技术有限公司 制备氟苯尼考中间体的方法及由该方法得到的化合物
CN111423391A (zh) * 2020-03-18 2020-07-17 浙江康牧药业有限公司 一种氟苯尼考中间体的制备方法
CN118084747B (zh) * 2024-04-28 2024-07-09 山东国邦药业有限公司 一种氟苯尼考的制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE957484C (de) * 1950-03-24 1957-02-07 Parke Davis & Co Verfahren zur Herstellung von neuen Oxazolinabkoemmlingen
DE830956C (de) * 1950-05-23 1952-02-07 Parke Davis & Co Verfahren zur Herstellung von Aminodiolen
US2768972A (en) * 1951-03-13 1956-10-30 Centre Nat Rech Scient Preparation of n-acyl-beta aryl-serinols
US2816915A (en) * 1953-11-20 1957-12-17 Du Pont Separation of phenyl-serines
US5663361A (en) * 1996-08-19 1997-09-02 Schering Corporation Process for preparing intermediates to florfenicol
CN1173933C (zh) * 2001-06-01 2004-11-03 中国科学院上海有机化学研究所 一种从l型取代苯丝氨酸酯制备d－（－）－苏式1－r－取代苯基－2－二氯乙酰氨基－3－氟－1－丙醇的方法
CN1155553C (zh) * 2001-12-07 2004-06-30 中国科学院上海有机化学研究所 2－氟－α－甲基－[1，1’－二苯基]－4－乙酸的对映体的制备方法
CN1649829A (zh) * 2002-03-08 2005-08-03 先灵-普劳有限公司 新型氟苯尼考类抗生素

Also Published As

Publication number Publication date
CL2008001562A1 (es) 2008-12-05
EP2155702A1 (en) 2010-02-24
RU2009148864A (ru) 2011-07-10
CA2688432A1 (en) 2008-12-11
AR066748A1 (es) 2009-09-09
AU2008260595A1 (en) 2008-12-11
CN101784534A (zh) 2010-07-21
BRPI0812297A2 (pt) 2014-11-25
JP2010529016A (ja) 2010-08-26
KR20100022999A (ko) 2010-03-03
US20080319200A1 (en) 2008-12-25
ZA200908404B (en) 2010-08-25
WO2008150406A1 (en) 2008-12-11
MX2009013016A (es) 2010-02-17
TW200904783A (en) 2009-02-01
AU2008260595A2 (en) 2010-01-07

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