WO2003078432A3 - Process for the synthesis of pergolide - Google Patents

Process for the synthesis of pergolide Download PDF

Info

Publication number
WO2003078432A3
WO2003078432A3 PCT/EP2003/002423 EP0302423W WO03078432A3 WO 2003078432 A3 WO2003078432 A3 WO 2003078432A3 EP 0302423 W EP0302423 W EP 0302423W WO 03078432 A3 WO03078432 A3 WO 03078432A3
Authority
WO
WIPO (PCT)
Prior art keywords
pergolide
synthesis
methylmercaptomethylergo
dihydrolysergic
intermediates
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
PCT/EP2003/002423
Other languages
French (fr)
Other versions
WO2003078432A2 (en
Inventor
Walter Cabri
Paolo Paissoni
Jacopo Roletto
Piera Fonte
Sara Olmo
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.)
Olon SpA
Original Assignee
Antibioticos SpA
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 claimed from IT2002MI000555A external-priority patent/ITMI20020555A1/en
Priority claimed from ITMI20022133 external-priority patent/ITMI20022133A1/en
Application filed by Antibioticos SpA filed Critical Antibioticos SpA
Priority to US10/507,620 priority Critical patent/US7019140B2/en
Priority to JP2003576437A priority patent/JP2005520833A/en
Priority to AU2003221494A priority patent/AU2003221494A1/en
Priority to DE60324776T priority patent/DE60324776D1/en
Priority to EP03717204A priority patent/EP1485382B1/en
Publication of WO2003078432A2 publication Critical patent/WO2003078432A2/en
Publication of WO2003078432A3 publication Critical patent/WO2003078432A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
    • C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
    • C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A process for the synthesis of pergolide (Formula(I)) (D-6-n-propyl-8β­methylmercaptomethylergo line) from acid 9,10-dihydrolysergic is herein disclosed. The process can be carried out without isolating most intermediates and is particularly convenient both from the yield and safety standpoint. Moreover, pergolide thereby obtained is highly pure and can be conveniently transformed into pergolide mesylate.
PCT/EP2003/002423 2002-03-15 2003-03-10 Process for the synthesis of pergolide Ceased WO2003078432A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US10/507,620 US7019140B2 (en) 2002-03-15 2003-03-10 Process for the synthesis of pergolide
JP2003576437A JP2005520833A (en) 2002-03-15 2003-03-10 Method for synthesizing pergolide
AU2003221494A AU2003221494A1 (en) 2002-03-15 2003-03-10 Process for the synthesis of pergolide
DE60324776T DE60324776D1 (en) 2002-03-15 2003-03-10 PROCESS FOR SYNTHESIS OF PERGOLID
EP03717204A EP1485382B1 (en) 2002-03-15 2003-03-10 Process for the synthesis of pergolide

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
ITMI2002A000555 2002-03-15
IT2002MI000555A ITMI20020555A1 (en) 2002-03-15 2002-03-15 PERGOLIDE SYNTHESIS PROCESS
ITMI20022133 ITMI20022133A1 (en) 2002-10-08 2002-10-08 PROCEDURE FOR THE PREPARATION OF THE PERGOLIDE.
ITMI2002A002133 2002-10-08

Publications (2)

Publication Number Publication Date
WO2003078432A2 WO2003078432A2 (en) 2003-09-25
WO2003078432A3 true WO2003078432A3 (en) 2004-01-15

Family

ID=28043508

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/002423 Ceased WO2003078432A2 (en) 2002-03-15 2003-03-10 Process for the synthesis of pergolide

Country Status (7)

Country Link
US (1) US7019140B2 (en)
EP (1) EP1485382B1 (en)
JP (1) JP2005520833A (en)
AT (1) ATE414704T1 (en)
AU (1) AU2003221494A1 (en)
DE (1) DE60324776D1 (en)
WO (1) WO2003078432A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102438981B (en) * 2009-04-17 2015-04-22 德国麦氏大药厂 Synthesis of 1-amino-1,3,3,5,5-pentamethylcyclohexane mesylate

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3901894A (en) * 1974-06-06 1975-08-26 Lilly Co Eli 8-thiomethylergolines
US4166182A (en) * 1978-02-08 1979-08-28 Eli Lilly And Company 6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds
EP0026671A1 (en) * 1979-10-01 1981-04-08 Eli Lilly And Company Novel ergoline derivatives, compositions containing them, their preparation and use as pharmaceuticals
EP0571202A1 (en) * 1992-05-21 1993-11-24 Eli Lilly And Company One-pot process for preparing pergolide
WO2000044748A1 (en) * 1999-01-27 2000-08-03 Poli Industria Chimica Spa Process for the preparation of alkyl mercapto methyl ergoline derivatives
CZ287962B6 (en) * 1999-06-15 2001-03-14 Galena A. S. Process for preparing 8{beta}-methylthiomethyl derivatives of ergoline

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3901894A (en) * 1974-06-06 1975-08-26 Lilly Co Eli 8-thiomethylergolines
US4166182A (en) * 1978-02-08 1979-08-28 Eli Lilly And Company 6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds
EP0026671A1 (en) * 1979-10-01 1981-04-08 Eli Lilly And Company Novel ergoline derivatives, compositions containing them, their preparation and use as pharmaceuticals
EP0571202A1 (en) * 1992-05-21 1993-11-24 Eli Lilly And Company One-pot process for preparing pergolide
US5463060A (en) * 1992-05-21 1995-10-31 Eli Lilly And Company One-pot process
WO2000044748A1 (en) * 1999-01-27 2000-08-03 Poli Industria Chimica Spa Process for the preparation of alkyl mercapto methyl ergoline derivatives
CZ287962B6 (en) * 1999-06-15 2001-03-14 Galena A. S. Process for preparing 8{beta}-methylthiomethyl derivatives of ergoline

Also Published As

Publication number Publication date
US20050124812A1 (en) 2005-06-09
ATE414704T1 (en) 2008-12-15
US7019140B2 (en) 2006-03-28
EP1485382A2 (en) 2004-12-15
AU2003221494A1 (en) 2003-09-29
WO2003078432A2 (en) 2003-09-25
DE60324776D1 (en) 2009-01-02
JP2005520833A (en) 2005-07-14
EP1485382B1 (en) 2008-11-19

Similar Documents

Publication Publication Date Title
WO2003084938A3 (en) Pyrimidone derivatives useful for the treatment of inflammatin and immunological diseases
IL165155A0 (en) Process for the manufacture of quinoline derivatives
HU9601857D0 (en) New benzyl-piperidine- or -tetrahydro-pyridine derivatives and processes for producing them
MY138263A (en) Therapeutic chroman compounds
YU94103A (en) Novel sulfonic acid derivatives
WO2002092564A3 (en) Synthesis of cyclopentadiene derivatives
WO2003011849A8 (en) Process for the production of beraprost and its salts
WO2002044194A1 (en) L-nucleic acid derivatives and processes for the synthesis thereof
AU2003255483A1 (en) Process for the conversion of polysulfanes
WO2004041167A3 (en) Antiprotozoal ring-substituted phospholipids
WO2002066449A3 (en) Process for the preparation of mesylates of piperazine derivatives
AU2003298178A1 (en) Process for the preparation of an essentially pure polymorph of an n-pyrazolyl-n'-naphthyl-urea
AU2002328835A1 (en) Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation
IL186014A0 (en) Process for the preparation of 2-azabicyclo[3.3.0] octane-3-carboxylic acid derivatives
SI1102765T1 (en) PROCESS FOR THE SYNTHESIS OF (1$i(H))-BENZO C)QUINOLIZIN-3-ONES DERIVATIVES
AU2003221494A1 (en) Process for the synthesis of pergolide
WO2002053537A8 (en) Process for preparing (±) trans-4-p-fluorophenyl-3-hydroxymethyl-1-methylpiperidine
WO2001035900A3 (en) Synthesis of 3-ethoxy-4-ethoxycarbonyl phenyl acetic acid, a key acid synthon of repaglinide
EP2497776A3 (en) Process for the production of tibolone
WO2004024681A3 (en) Novel compounds comprising a thiocarbonyl-sulfanyl group, which can be used for the radical synthesis of alpha-perfluoroalkylamines
WO2001083423A3 (en) 2,6-diamino-6-methyl-heptanoic acid and derivatives, process for the preparation thereof and use thereof
HU0102118D0 (en) Process for chloromethylation
MY139289A (en) Process for the synthesis of perindopril and pharmaceutically acceptable salts thereof
AU2002247949A1 (en) Process for synthesis of trans-alkenoic acid, use thereof
WO2004096828A3 (en) Novel method and intermediates for the preparation of 19-nor-steroid compounds

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 2003576437

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 10507620

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 2003717204

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2003717204

Country of ref document: EP