WO2001014576B1 - Process and intermediates for the preparation of isoxazolecaroxamides and analogues - Google Patents

Process and intermediates for the preparation of isoxazolecaroxamides and analogues

Info

Publication number
WO2001014576B1
WO2001014576B1 PCT/US2000/023032 US0023032W WO0114576B1 WO 2001014576 B1 WO2001014576 B1 WO 2001014576B1 US 0023032 W US0023032 W US 0023032W WO 0114576 B1 WO0114576 B1 WO 0114576B1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
alkali metal
addition salts
acid addition
Prior art date
Application number
PCT/US2000/023032
Other languages
French (fr)
Other versions
WO2001014576A2 (en
WO2001014576A3 (en
WO2001014576A8 (en
Inventor
Junhua Tao
Srinivasan Babu
Raymond Dagnino Jr
Qingping Tian
Travis Paul Remarchuk
Kevin Scott Mcgee
Naresh K Nayyar
Terence Jarold Moran
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
Priority to EP00955830A priority Critical patent/EP1206470A2/en
Priority to IL14786200A priority patent/IL147862A0/en
Priority to KR1020027002323A priority patent/KR20020030795A/en
Priority to HU0203315A priority patent/HUP0203315A3/en
Priority to AU67970/00A priority patent/AU778062B2/en
Priority to BR0013323-0A priority patent/BR0013323A/en
Priority to CA002376509A priority patent/CA2376509A1/en
Priority to MXPA02001947A priority patent/MXPA02001947A/en
Application filed by Agouron Pharma filed Critical Agouron Pharma
Priority to JP2001518887A priority patent/JP2003511350A/en
Publication of WO2001014576A2 publication Critical patent/WO2001014576A2/en
Publication of WO2001014576A3 publication Critical patent/WO2001014576A3/en
Publication of WO2001014576B1 publication Critical patent/WO2001014576B1/en
Publication of WO2001014576A8 publication Critical patent/WO2001014576A8/en
Priority to HK03103445A priority patent/HK1051363A1/en

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Classifications

    • 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
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • 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
    • 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
    • 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
    • B01J2219/00002—Chemical plants
    • B01J2219/00027—Process aspects
    • B01J2219/00033—Continuous processes
    • 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
    • B01J2219/00074—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
    • B01J2219/00103—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor in a heat exchanger separate from the reactor
    • 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
    • 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
    • B01J2219/00162—Controlling or regulating processes controlling the pressure
    • 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
    • B01J2219/00177—Controlling or regulating processes controlling the pH
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Abstract

Efficient synthetic routes for the preparation of rhinovirus protease inhibitors of formula (I), particulary (I'), key intermediates useful in those synthetic routes, as well as a continuous membrane reactor useful for those synthetic routes. These compounds of formula (I), as well as pharmaceutical compositions that contain these compounds, are suitable for treating patients or hosts infected with one or more picornaviruses.

Claims

AMENDED CLAIMS
[received by the International Bureau on 1 May 2001 (01.05.01 ); original claims 45-49 and 57-63 cancelled; remaining claims unchanged (4 pages)]
43. The process according to claim 41, wherein step (b) is performed at about 80°C.
44. The process according to claim 41, wherein the palladium-mediated reduction step is done in the presence of formic acid at about room temperature.
45. A compound of the following formula:
Figure imgf000003_0001
and acid addition salts thereof.
46. A compound of the following formula:
Figure imgf000003_0002
and acid addition salts thereof. 47. A compound of the following formula:
Figure imgf000003_0003
and acid addition salts thereof.
48. A compound of the following formula:
Figure imgf000004_0001
and acid addition salts thereof.
49. A process for preparing a compound of formula VLT:
Figure imgf000004_0002
wherein R10 is a halogen or an alkyl group; comprising:
Step A: converting a compound of formula NI to a compound of formula V comprising the substeps of:
(a) reacting a R10 substituted benzaldehyde of formula VI:
Figure imgf000004_0003
with hydantoin in an aqueous medium in the presence of a catalyst at reflux temperature to form a reaction mixture;
(b) treating the reaction mixture with an excess of an alkali metal hydroxide at reflux temperature to form a alkali metal hydroxide-treated solution;
(c) adding an alkali metal halide to the alkali metal hydroxide-treated solution to give a solution;
(d) acidifying the solution with a concentrated acid to give a precipitate of formula V:
Figure imgf000005_0001
Step B: the enzymatic reduction of the compound of formula V to the compound of formula VII.
50. A process for preparing a compound of formula VTI
Figure imgf000005_0002
comprising the steps:
(a) converting serine to potassium glycidate by a standard process;
(b) carrying out a regioselective epoxide ring-opening reaction with a compound of formula R10-phenyl-Q to yield the compound of formula VII, wherein R10 is a halogen or an alkyl group; and
Q is an activated bromide, a sulfate, or a primary iodide.
51. The process according to claim 50, wherein the potassium glycidate formed from step (a) is converted to a glycidic acid before the regioselective epoxide ring- opening reaction of step (b) is performed.
PCT/US2000/023032 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues WO2001014576A2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
CA002376509A CA2376509A1 (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues
KR1020027002323A KR20020030795A (en) 1999-08-24 2000-08-23 Process and Intermediates for the Preparation of Isoxazolecaroxamides and Analogues
HU0203315A HUP0203315A3 (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues
AU67970/00A AU778062B2 (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues
BR0013323-0A BR0013323A (en) 1999-08-24 2000-08-23 Useful processes for the preparation of antipicornaviral agents, processes useful for the preparation of a compound, compounds, processes for the preparation of a compound and processes for carrying out a reaction catalyzed by a large catalyst
EP00955830A EP1206470A2 (en) 1999-08-24 2000-08-23 Processes and intermediates for the preparation of isoxazolecarboxamides and analogues
MXPA02001947A MXPA02001947A (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues.
IL14786200A IL147862A0 (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation os isoxazolecaroxamides and analogues
JP2001518887A JP2003511350A (en) 1999-08-24 2000-08-23 Process for preparing isoxazole carboxamides and analogs and intermediates
HK03103445A HK1051363A1 (en) 1999-08-24 2003-05-15 Efficient methods for the preparation of rhinovirus protease inhibitors, key intermediates and a continuous membrane reactor useful for preparing the same.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15036599P 1999-08-24 1999-08-24
US60/150,365 1999-08-24

Publications (4)

Publication Number Publication Date
WO2001014576A2 WO2001014576A2 (en) 2001-03-01
WO2001014576A3 WO2001014576A3 (en) 2001-08-30
WO2001014576B1 true WO2001014576B1 (en) 2001-09-27
WO2001014576A8 WO2001014576A8 (en) 2002-06-20

Family

ID=22534191

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/023032 WO2001014576A2 (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues

Country Status (15)

Country Link
EP (1) EP1206470A2 (en)
JP (1) JP2003511350A (en)
KR (1) KR20020030795A (en)
CN (2) CN1524960A (en)
AU (1) AU778062B2 (en)
BR (1) BR0013323A (en)
CA (1) CA2376509A1 (en)
CZ (1) CZ2002634A3 (en)
HK (1) HK1051363A1 (en)
HU (1) HUP0203315A3 (en)
IL (1) IL147862A0 (en)
MX (1) MXPA02001947A (en)
PL (1) PL357162A1 (en)
WO (1) WO2001014576A2 (en)
ZA (1) ZA200200506B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EA003856B1 (en) 1998-04-30 2003-10-30 Агурон Фармасьютикалз, Инк. 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.
US6774243B2 (en) 1999-08-24 2004-08-10 Agouron Pharmaceuticals, Inc. Efficient synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates
PE20020157A1 (en) 1999-12-03 2002-02-22 Agouron Pharma PYRIDONE DERIVED COMPOUNDS AS PICORNAVIRAL 3C PROTEASE INHIBITORS, COMPOSITIONS, THEIR PHARMACEUTICAL USES AND MATERIALS FOR THEIR SYNTHESIS
PA8515201A1 (en) 2000-04-14 2002-10-24 Agouron Pharma ANTIPICORNAVIRAL COMPOUNDS AND COMPOSITIONS; YOUR PHARMACEUTICAL USES AND MATERIALS FOR SYNTHESIS
MXPA02012456A (en) 2000-06-14 2004-01-26 Agouron Pharma Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis.
DE10208007A1 (en) * 2002-02-26 2003-09-18 Forschungszentrum Juelich Gmbh Process for the production of alcohols from substrates by means of oxidoreductases, two-phase system comprising an aqueous phase and an organic phase and device for carrying out the process
CN106831657B (en) * 2017-02-23 2019-07-16 江苏工程职业技术学院 A kind of preparation method of glycidic acid potassium

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2426651C3 (en) * 1974-06-01 1982-04-08 Bayer Ag, 5090 Leverkusen (-) - Antipode of methyl 3- (p-chlorophenyl) -2-chloropropionate, process for its preparation and its use as a herbicide
DE2930087A1 (en) * 1979-07-25 1981-02-26 Biotechnolog Forschung Gmbh METHOD FOR THE CONTINUOUS ENCYMATIC CONVERSION OF WATER-SOLUBLE ALPHA KETOCARBONIC ACIDS INTO THE CORRESPONDING ALPHA HYDROXYCARBONIC ACIDS
JPH0623131B2 (en) * 1984-08-07 1994-03-30 三井東圧化学株式会社 Process for producing alkali metal salt of α-keto acid
JPH066539B2 (en) * 1986-03-14 1994-01-26 三共株式会社 Process for producing α-hydroxycarboxylic acid derivative
FR2686897B1 (en) * 1992-02-05 1995-07-13 Sonertec CONTINUOUS PROCESS FOR THE MANUFACTURE OF ORGANIC ACIDS.
US5360927A (en) * 1994-01-24 1994-11-01 Development Center For Biotechnology Process for the preparation of monohydrated sodium phenylpyruvate
US5869697A (en) * 1994-05-02 1999-02-09 Council Of Scientific & Industrial Research Process for preparing diltiazem

Also Published As

Publication number Publication date
KR20020030795A (en) 2002-04-25
CA2376509A1 (en) 2001-03-01
CN1524960A (en) 2004-09-01
HUP0203315A3 (en) 2003-12-29
WO2001014576A2 (en) 2001-03-01
CN1382139A (en) 2002-11-27
IL147862A0 (en) 2002-08-14
MXPA02001947A (en) 2002-10-31
WO2001014576A3 (en) 2001-08-30
HUP0203315A2 (en) 2003-02-28
HK1051363A1 (en) 2003-08-01
WO2001014576A8 (en) 2002-06-20
BR0013323A (en) 2002-04-02
CN1157391C (en) 2004-07-14
ZA200200506B (en) 2003-06-25
AU778062B2 (en) 2004-11-11
AU6797000A (en) 2001-03-19
EP1206470A2 (en) 2002-05-22
JP2003511350A (en) 2003-03-25
CZ2002634A3 (en) 2002-09-11
PL357162A1 (en) 2004-07-26

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