CO5200782A1 - Las rutas sinteticas eficientes para la preparacion de los inhibidores d ela proteasa del rinovirus y los intermedios claves - Google Patents

Las rutas sinteticas eficientes para la preparacion de los inhibidores d ela proteasa del rinovirus y los intermedios claves

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Publication number
CO5200782A1
CO5200782A1 CO00063457A CO00063457A CO5200782A1 CO 5200782 A1 CO5200782 A1 CO 5200782A1 CO 00063457 A CO00063457 A CO 00063457A CO 00063457 A CO00063457 A CO 00063457A CO 5200782 A1 CO5200782 A1 CO 5200782A1
Authority
CO
Colombia
Prior art keywords
compound
formula
affirmation
jpeg
produce
Prior art date
Application number
CO00063457A
Other languages
English (en)
Inventor
Tian Qingping
K Nayyar Naresh
Babu Srinivasan
Tao Junhua
Jarold Moran Terence
Raymonf Dagnino
Paul Remarchuk Travis
Michael Joseph Melnick
J Mitchell Lennert
Steven Lee Bender
Original Assignee
Agouron Pharma
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 Agouron Pharma filed Critical Agouron Pharma
Publication of CO5200782A1 publication Critical patent/CO5200782A1/es

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2415—Tubular reactors
    • B01J19/2435—Loop-type reactors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2475—Membrane reactors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • 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
    • C07C69/73—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 unsaturated acids
    • C07C69/732—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 unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
    • 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
    • C07D413/12—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 chain containing hetero atoms as chain links
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
    • B01J2219/00099—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor the reactor being immersed in the heat exchange medium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00159—Controlling the temperature controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Enzymes And Modification Thereof (AREA)

Abstract

Un proceso útil en la sintetización de compuestos contra el picornavirus, que consta de:(a) realizar la cianometilación de un compuesto de la fórmula V utilizando bis(trimetisilo)amida y bromoacetonitrilo para producir un compuesto de la fórmula VI; <EMI FILE="00063457_1" ID="1" IMF=JPEG >(b) realizar la disminución, luego la ciclización, y después la desprotección del compuesto de la fórmula VI para producir un compuesto de la fórmula VII; y<EMI FILE="00063457_2" ID="2" IMF=JPEG >(c) realizar la oxidación y olefinación del compuesto de la fórmula VII mediante la reacción del compuesto de la fórmula VII con un complejo de SO3-piridina para producir una mezcla de reacción y reaccionar la mezcla de reacción con un compuesto para la fórmula VIII para formar un compuesto de la fórmula IV:<EMI FILE="00063457_3" ID="3" IMF=JPEG >en donde R1 es H, F, un grupo alquilo, OR, SR, o un grupo O-alquilo;donde cada R41 es independientemente H o un alquilo inferior; y X es cualquier grupo protectivo aceptado para nitrógeno.El proceso de la afirmación 1, en donde el compuesto de la fórmula V es preparado a partir de N-Boc L ácido glutámico ?-benzilo éster.El proceso de la afirmación 1, en donde X es un grupo Boc.El proceso de la afirmación 1, en donde R41 es H.El proceso de la afirmación 1, en donde Z1 es H.El proceso de la afirmación 1, en donde Z es -COOEt.
CO00063457A 1999-08-24 2000-08-24 Las rutas sinteticas eficientes para la preparacion de los inhibidores d ela proteasa del rinovirus y los intermedios claves CO5200782A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US15035899P 1999-08-24 1999-08-24

Publications (1)

Publication Number Publication Date
CO5200782A1 true CO5200782A1 (es) 2002-09-27

Family

ID=22534156

Family Applications (1)

Application Number Title Priority Date Filing Date
CO00063457A CO5200782A1 (es) 1999-08-24 2000-08-24 Las rutas sinteticas eficientes para la preparacion de los inhibidores d ela proteasa del rinovirus y los intermedios claves

Country Status (20)

Country Link
EP (1) EP1206450A1 (es)
JP (1) JP2003507453A (es)
KR (1) KR20020046283A (es)
CN (1) CN1168713C (es)
AR (1) AR025380A1 (es)
AU (1) AU770221B2 (es)
BR (1) BR0013306A (es)
CA (1) CA2376452A1 (es)
CO (1) CO5200782A1 (es)
CZ (1) CZ2002632A3 (es)
HK (1) HK1049336B (es)
HU (1) HUP0203365A3 (es)
IL (1) IL147674A0 (es)
MX (1) MXPA02001944A (es)
PE (1) PE20010517A1 (es)
PL (1) PL353997A1 (es)
TW (1) TWI245040B (es)
UY (1) UY26307A1 (es)
WO (1) WO2001014329A1 (es)
ZA (1) ZA200200504B (es)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL351250A1 (en) 1998-04-30 2003-04-07 Agouron Pharma Antipicornaviral compounds, their preparation and use
JP2003506457A (ja) 1999-08-04 2003-02-18 アグロン・ファーマシュウティカルズ・インコーポレーテッド 抗ピコルナウィルス化合物及び組成物、その医薬的使用、並びにその合成のための物質
PA8507801A1 (es) 1999-12-03 2002-08-26 Agouron Pharma Compuestos y composiciones antipicornavirales, sus usos farmaceuticos y los materiales para su sintesis
PE20011277A1 (es) 2000-04-14 2002-01-07 Agouron Pharma Compuestos y composiciones antipicornavirales, sus usos farmaceuticos y los materiales para su sintesis
MXPA02012456A (es) 2000-06-14 2004-01-26 Agouron Pharma Compuestos y composiciones antipicornavirales, sus usos farmaceuticos y materiales para su sintesis.
CN1309712C (zh) * 2004-04-02 2007-04-11 中国科学院上海有机化学研究所 Ag7088类化合物的关键中间体的前体及其合成方法
CA3174069A1 (en) 2020-03-06 2021-09-10 Pfizer Inc. Methods of inhibiting sars-cov-2 replication and treating coronavirus disease 2019
CN115260074A (zh) * 2022-08-02 2022-11-01 爱斯特（成都）生物制药股份有限公司 一种口服抗病毒药物Paxlovid中间体的制备方法
CN115322130B (zh) * 2022-08-02 2024-05-14 南京正济医药研究有限公司 制备(s)-2-(boc-氨基)-3-[(s)-2-氧代-3-吡咯烷基]丙酸甲酯

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2254343A1 (en) * 1996-05-14 1997-11-20 Agouron Pharmaceuticals, Inc. Inhibitors of picornavirus 3c proteases and methods for their use and preparation
WO1998043950A1 (en) * 1997-03-28 1998-10-08 Agouron Pharmaceuticals, Inc. Antipicornaviral compouds, compositions containing them, and methods for their use
US5962487A (en) * 1997-12-16 1999-10-05 Agouron Pharmaceuticals, Inc. Antipicornaviral compounds and methods for their use and preparation
PL351250A1 (en) * 1998-04-30 2003-04-07 Agouron Pharma Antipicornaviral compounds, their preparation and use

Also Published As

Publication number Publication date
CN1168713C (zh) 2004-09-29
UY26307A1 (es) 2001-04-30
IL147674A0 (en) 2002-08-14
KR20020046283A (ko) 2002-06-20
CA2376452A1 (en) 2001-03-01
WO2001014329A1 (en) 2001-03-01
CZ2002632A3 (cs) 2003-04-16
EP1206450A1 (en) 2002-05-22
HUP0203365A3 (en) 2003-12-29
PL353997A1 (en) 2003-12-15
HUP0203365A2 (hu) 2003-02-28
PE20010517A1 (es) 2001-05-16
JP2003507453A (ja) 2003-02-25
TWI245040B (en) 2005-12-11
CN1374947A (zh) 2002-10-16
ZA200200504B (en) 2003-03-26
MXPA02001944A (es) 2002-10-31
HK1049336A1 (en) 2003-05-09
HK1049336B (zh) 2005-05-20
AU6797100A (en) 2001-03-19
AU770221B2 (en) 2004-02-19
BR0013306A (pt) 2002-05-28
AR025380A1 (es) 2002-11-20

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