CO5200782A1 - THE EFFICIENT SYNTHETIC ROUTES FOR THE PREPARATION OF THE INHIBITORS OF THE PROTEIN OF THE RINOVIRUS AND THE KEY INTERMEDIATES - Google Patents

THE EFFICIENT SYNTHETIC ROUTES FOR THE PREPARATION OF THE INHIBITORS OF THE PROTEIN OF THE RINOVIRUS AND THE KEY INTERMEDIATES

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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
Spanish (es)
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/en

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Peptides Or Proteins (AREA)
  • Pyrrole Compounds (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.A useful process in the synthesis of compounds against picornavirus, which consists of: (a) performing the cyanomethylation of a compound of the formula V using bis (trimethylsyl) amide and bromoacetonitrile to produce a compound of the formula VI; <EMI FILE = "00063457_1" ID = "1" MFI = JPEG> (b) perform the decrease, then the cyclization, and then the deprotection of the compound of the formula VI to produce a compound of the formula VII; and <EMI FILE = "00063457_2" ID = "2" MFI = JPEG> (c) perform oxidation and olefination of the compound of formula VII by reacting the compound of formula VII with a complex of SO3-pyridine to produce a reaction mixture and react the reaction mixture with a compound for formula VIII to form a compound of formula IV: <EMI FILE = "00063457_3" ID = "3" IMF = JPEG> where R1 is H, F, a alkyl group, OR, SR, or an O-alkyl group, wherein each R41 is independently H or a lower alkyl; and X is any protective group accepted for nitrogen. The process of claim 1, wherein the compound of formula V is prepared from N-Boc L glutamic acid? -benzyl ester. The process of claim 1, wherein X is a Boc group. The process of affirmation 1, where R41 is H. The process of affirmation 1, where Z1 is H. The process of affirmation 1, where Z is -COOEt.

CO00063457A 1999-08-24 2000-08-24 THE EFFICIENT SYNTHETIC ROUTES FOR THE PREPARATION OF THE INHIBITORS OF THE PROTEIN OF THE RINOVIRUS AND THE KEY INTERMEDIATES CO5200782A1 (en)

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 (en) 2002-09-27

Family

ID=22534156

Family Applications (1)

Application Number Title Priority Date Filing Date
CO00063457A CO5200782A1 (en) 1999-08-24 2000-08-24 THE EFFICIENT SYNTHETIC ROUTES FOR THE PREPARATION OF THE INHIBITORS OF THE PROTEIN OF THE RINOVIRUS AND THE KEY INTERMEDIATES

Country Status (20)

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

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AP2000001934A0 (en) 1998-04-30 2000-12-31 Agouron Pharma Antipicornaviral compounds, their preparation and use.
ES2230135T3 (en) 1999-08-04 2005-05-01 Agouron Pharmaceuticals, Inc. ANTI-PICORNAVIRAL COMPOUNDS AND COMPOSITIONS; PHARMACEUTICAL AND MATERIAL USES USED FOR SYNTHESIS.
PA8507801A1 (en) 1999-12-03 2002-08-26 Agouron Pharma ANTIPICORNAVIRAL COMPOUNDS AND COMPOSITIONS, THEIR PHARMACEUTICAL USES AND THE MATERIALS FOR SYNTHESIS
PA8515201A1 (en) 2000-04-14 2002-10-24 Agouron Pharma ANTIPICORNAVIRAL COMPOUNDS AND COMPOSITIONS; YOUR PHARMACEUTICAL USES AND MATERIALS FOR SYNTHESIS
HUP0301331A3 (en) 2000-06-14 2004-03-01 Agouron Pharmaceuticals Inc La Antipicornaviral compounds process for their preparation and compositions containing them, their pharmaceutical uses, and intermediates for their synthesis
CN1309712C (en) * 2004-04-02 2007-04-11 中国科学院上海有机化学研究所 Precursor of key intermediate of AG 7088 class compound and its sythetic process
CA3174069A1 (en) 2020-03-06 2021-09-10 Pfizer Inc. Methods of inhibiting sars-cov-2 replication and treating coronavirus disease 2019
CN115322130B (en) * 2022-08-02 2024-05-14 南京正济医药研究有限公司 Preparation of (S) -2- (BOC-amino) -3- [ (S) -2-oxo-3-pyrrolidinyl ] propanoic acid methyl ester
CN115260074B (en) * 2022-08-02 2024-06-21 爱斯特（成都）生物制药股份有限公司 Preparation method of oral antiviral drug Paxlovid intermediate

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
DE69817798T2 (en) * 1997-03-28 2004-08-05 Agouron Pharmaceuticals, Inc., La Jolla COMPOUNDS AGAINST PICORNA VIRUSES, COMPOSITIONS THAT CONTAIN THESE COMPOUNDS 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
AP2000001934A0 (en) * 1998-04-30 2000-12-31 Agouron Pharma Antipicornaviral compounds, their preparation and use.

Also Published As

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

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