AU770221B2 - Synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates - Google Patents

Synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates Download PDF

Info

Publication number
AU770221B2
AU770221B2 AU67971/00A AU6797100A AU770221B2 AU 770221 B2 AU770221 B2 AU 770221B2 AU 67971/00 A AU67971/00 A AU 67971/00A AU 6797100 A AU6797100 A AU 6797100A AU 770221 B2 AU770221 B2 AU 770221B2
Authority
AU
Australia
Prior art keywords
group
formula
compound
cycloalkyl
independently
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
AU67971/00A
Other languages
English (en)
Other versions
AU6797100A (en
Inventor
Srinivasan Babu
Steven Lee Bender
Raymond Dagnino Jr.
Michael Joseph Melnick
Lennert J. Mitchell
Terence Jarold Moran
Naresh K. Nayyar
Travis Paul Remarchuk
Junhua Tao
Qingping Tian
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Agouron Pharmaceuticals LLC
Original Assignee
Agouron Pharmaceuticals LLC
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 Pharmaceuticals LLC filed Critical Agouron Pharmaceuticals LLC
Publication of AU6797100A publication Critical patent/AU6797100A/en
Application granted granted Critical
Publication of AU770221B2 publication Critical patent/AU770221B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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)
  • 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)
  • Pyrrole Compounds (AREA)
  • Peptides Or Proteins (AREA)
AU67971/00A 1999-08-24 2000-08-23 Synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates Ceased AU770221B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US15035899P 1999-08-24 1999-08-24
US60/150358 1999-08-24
PCT/US2000/023033 WO2001014329A1 (en) 1999-08-24 2000-08-23 Synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates

Publications (2)

Publication Number Publication Date
AU6797100A AU6797100A (en) 2001-03-19
AU770221B2 true AU770221B2 (en) 2004-02-19

Family

ID=22534156

Family Applications (1)

Application Number Title Priority Date Filing Date
AU67971/00A Ceased AU770221B2 (en) 1999-08-24 2000-08-23 Synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates

Country Status (20)

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

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUP0400624A2 (hu) 1998-04-30 2004-06-28 Agouron Pharmaceuticals, Inc. Picornavírus-ellenes vegyületek, előállításuk és alkalmazásuk
CA2380647A1 (en) 1999-08-04 2001-02-15 Agouron Pharmaceuticals, Inc. Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis
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
JP2004503533A (ja) 2000-06-14 2004-02-05 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 抗ピコルナウイ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
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
US20230157998A1 (en) 2020-03-06 2023-05-25 Pfizer Inc. Methods of Inhibiting SARS-CoV-2 Replication and Treating Corona Virus 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
GT199700061A (es) * 1996-05-14 1998-11-04 Procedimiento para la obtencion de "compuestos antipicornavirales y metodos para su uso y preparacion".
ES2206907T3 (es) * 1997-03-28 2004-05-16 Agouron Pharmaceuticals, Inc. Compuestos anti-picornavirus, composiciones que contienen estos compuestos y sus procedimientos de utilizacion.
US5962487A (en) * 1997-12-16 1999-10-05 Agouron Pharmaceuticals, Inc. Antipicornaviral compounds and methods for their use and preparation
HUP0400624A2 (hu) * 1998-04-30 2004-06-28 Agouron Pharmaceuticals, Inc. Picornavírus-ellenes vegyületek, előállításuk és alkalmazásuk

Also Published As

Publication number Publication date
CO5200782A1 (es) 2002-09-27
CZ2002632A3 (cs) 2003-04-16
HUP0203365A3 (en) 2003-12-29
WO2001014329A1 (en) 2001-03-01
EP1206450A1 (en) 2002-05-22
PL353997A1 (en) 2003-12-15
HK1049336B (zh) 2005-05-20
UY26307A1 (es) 2001-04-30
KR20020046283A (ko) 2002-06-20
MXPA02001944A (es) 2002-10-31
HUP0203365A2 (hu) 2003-02-28
CA2376452A1 (en) 2001-03-01
PE20010517A1 (es) 2001-05-16
BR0013306A (pt) 2002-05-28
AU6797100A (en) 2001-03-19
TWI245040B (en) 2005-12-11
ZA200200504B (en) 2003-03-26
IL147674A0 (en) 2002-08-14
JP2003507453A (ja) 2003-02-25
CN1374947A (zh) 2002-10-16
CN1168713C (zh) 2004-09-29
AR025380A1 (es) 2002-11-20
HK1049336A1 (en) 2003-05-09

Similar Documents

Publication Publication Date Title
AU599636B2 (en) Transglutaminase inhibitors
Webb et al. Conformationally restricted arginine analogs
MX2015006458A (es) Sintesis de derivados de isoxazolina espirociclicos.
OA11503A (en) Antipicornaviral compounds, their preparation and use.
RU2730006C1 (ru) Способ получения 5r-[(бензилокси)амино]пиперидин-2s-карбоновой кислоты или её производного
AU770221B2 (en) Synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates
US6514997B2 (en) Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis
MX2007015418A (es) Procedimiento para preparar inhibidores de renina.
EP3507282B1 (en) Process for preparing indole carboxamide compounds
CN106573919B (zh) 制备吲哚化合物的方法
JPH02218663A (ja) 新規なプロリン誘導体
US6355807B1 (en) Efficient synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates
AU2019391942B2 (en) Macrocyclic compound and use thereof
US6774243B2 (en) Efficient synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates
WO2021106864A1 (en) Process for the preparation of producing pyrazolo[1,5-a] pyrimidine derivatives
WO2001014576A2 (en) Process and intermediates for the preparation of isoxazolecaroxamides and analogues
JPWO2002048153A1 (ja) Ｇｍ−９５物質の製法
AU2005252111A1 (en) Highly selective novel amidation method
Rodríguez et al. Synthesis of enantiomerically pure δ-benzylproline derivatives
CN117466796A (zh) 一种((2R,7aS)-2-氟六氢-1H-吡咯嗪-7a-基)甲醇的制备方法
JP4180366B2 (ja) 抗菌性化合物製造用原料化合物の製法およびその中間体
JPH08283289A (ja) ペプチド誘導体の製造方法
JPH11199562A (ja) １−（３−アルカノイルチオ−２−アルキルプロパノイル）−プロリルフェニルアラニンの製造方法

Legal Events

Date Code Title Description
FGA Letters patent sealed or granted (standard patent)