AR067198A1 - Procesos para preparar carboxaldehido oxazina biciclico y un compuesto inhibidor de (beta) lactamasa y compuesto preparado durante alguno de los procesos - Google Patents

Procesos para preparar carboxaldehido oxazina biciclico y un compuesto inhibidor de (beta) lactamasa y compuesto preparado durante alguno de los procesos

Info

Publication number
AR067198A1
AR067198A1 ARP080102778A ARP080102778A AR067198A1 AR 067198 A1 AR067198 A1 AR 067198A1 AR P080102778 A ARP080102778 A AR P080102778A AR P080102778 A ARP080102778 A AR P080102778A AR 067198 A1 AR067198 A1 AR 067198A1
Authority
AR
Argentina
Prior art keywords
formula
compound
beta
processes
alkyl
Prior art date
Application number
ARP080102778A
Other languages
English (en)
Inventor
Kenneth KREMER
Lalitha Krishnan
Joseph Zeldis
Meliard Jennings
Aranapakam Vankatesan
Takao Abe
Tarek S Mansour
Original Assignee
Wyeth Corp
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 Wyeth Corp filed Critical Wyeth Corp
Publication of AR067198A1 publication Critical patent/AR067198A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C47/263—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Un primer proceso para preparar el compuesto carboxaldehído oxazina bicíclico, y su uso en la preparacion de inhibidores de beta-lactamasa. Se hace reaccionar un compuesto de formula (2), o una sal de éste, con un compuesto de formula (3) en presencia de un carbonato álcali o una base amina. Se prepara el inhibidor de beta-lactamasa de formula (4), donde R1 es H, una sal de Na K o Ca, o un éster hidrolizable in vivo de un alquilo C1-6, un cicloalquilo C5-6 o un -CHR2OC(O) alquilo C1-6, y R2 es H, un alquilo C1-6, un cicloalquilo C3-6, un arilo, un heteroarilo o una sal aceptable farmacéuticamente o hidrato de éstos, condensando el compuesto preparado segun el primer proceso con el derivado 6-bromo-peneme de formula (5) (donde R3 es para-nitrobencilo, bencilo, para-metoxi bencilo, benzhidrol o tritilo) en la presencia de un ácido Lewis y una base, para formar un producto aldol intermedio de formula (6) haciendo reaccionar este producto aldol intermedio con un cloruro de ácido de la formula R4Cl, un anhídrido de la formula (R4)2s, o C(X1)4 y trifenilfosfina (donde R4 es alquilo C1-6-SO2-, arilo C3-13-SO2-, alquilo C1-6-C(O)-, o arilo C3-14-C(O)- y X1 es Br, I o Cl), para formar un intermedio de formula (7) donde R5 es -OR4 o X1; y convirtiendo este intermedio al compuesto inhibidor de beta-lactamasa, o una sal farmacéuticamente aceptable o hidrato de éste, mediante un proceso de eliminacion reductora.
ARP080102778A 2007-06-28 2008-06-27 Procesos para preparar carboxaldehido oxazina biciclico y un compuesto inhibidor de (beta) lactamasa y compuesto preparado durante alguno de los procesos AR067198A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US93761207P 2007-06-28 2007-06-28

Publications (1)

Publication Number Publication Date
AR067198A1 true AR067198A1 (es) 2009-09-30

Family

ID=39830005

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP080102778A AR067198A1 (es) 2007-06-28 2008-06-27 Procesos para preparar carboxaldehido oxazina biciclico y un compuesto inhibidor de (beta) lactamasa y compuesto preparado durante alguno de los procesos

Country Status (7)

Country Link
US (1) US20090018332A1 (es)
AR (1) AR067198A1 (es)
CL (1) CL2008001893A1 (es)
PA (1) PA8786501A1 (es)
PE (1) PE20090431A1 (es)
TW (1) TW200922939A (es)
WO (1) WO2009006243A2 (es)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102020659B (zh) * 2009-09-11 2013-07-03 中国中化股份有限公司 一种甲缩醛青霉烯中间体的制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2823226A (en) * 1953-08-28 1958-02-11 Mitsubishi Chem Ind Preparation of malondialdehyde derivatives
US5565577A (en) * 1992-09-23 1996-10-15 Smithkline Beecham Corporation Process for preparing 1-alkyaryl-2-alkyl-5-formylimidazole
AR039476A1 (es) * 2002-05-01 2005-02-23 Wyeth Corp Proceso para preparar derivados de 6-alquiliden penem
US20040132708A1 (en) * 2002-05-01 2004-07-08 Wyeth Process for preparing 6-alkylidene penem derivatives
AR039774A1 (es) * 2002-05-01 2005-03-02 Wyeth Corp 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas
WO2006081807A2 (de) * 2005-02-03 2006-08-10 Ratiopharm Gmbh Verfahren zur herstellung von losartan
TW200716102A (en) * 2005-06-01 2007-05-01 Wyeth Corp Bicyclic 6-alkylidene-penems as class-D β -lactamases inhibitors
WO2007016134A1 (en) * 2005-07-27 2007-02-08 Wyeth BICYCLIC 6-ALKYLIDENE-PENEM B-LACTAMASE INHIBITORS AND β-LACTAM ANTIBIOTIC COMBINATION: A BROAD SPECTRUM ANTIBIOTIC

Also Published As

Publication number Publication date
WO2009006243A3 (en) 2009-04-02
PA8786501A1 (es) 2009-01-23
PE20090431A1 (es) 2009-04-09
WO2009006243A8 (en) 2009-11-05
WO2009006243A2 (en) 2009-01-08
TW200922939A (en) 2009-06-01
CL2008001893A1 (es) 2008-08-08
US20090018332A1 (en) 2009-01-15

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