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WO2000002855A3 - Synthesis of compounds useful in the manufacture of ketorolac - Google Patents

Synthesis of compounds useful in the manufacture of ketorolac Download PDF

Info

Publication number
WO2000002855A3
WO2000002855A3 PCT/US1999/015496 US9915496W WO0002855A3 WO 2000002855 A3 WO2000002855 A3 WO 2000002855A3 US 9915496 W US9915496 W US 9915496W WO 0002855 A3 WO0002855 A3 WO 0002855A3
Authority
WO
WIPO (PCT)
Prior art keywords
ketorolac
synthesis
manufacture
compounds useful
compound
Prior art date
Application number
PCT/US1999/015496
Other languages
French (fr)
Other versions
WO2000002855A2 (en
Inventor
John R Duchek
Henry J Buehler
Douglas C Caskey
Original Assignee
Mallinckrodt Inc
John R Duchek
Henry J Buehler
Douglas C Caskey
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 Mallinckrodt Inc, John R Duchek, Henry J Buehler, Douglas C Caskey filed Critical Mallinckrodt Inc
Priority to DE69930940T priority Critical patent/DE69930940T2/en
Priority to EP99937220A priority patent/EP1097152B1/en
Priority to JP2000559086A priority patent/JP2002520313A/en
Priority to AU52096/99A priority patent/AU5209699A/en
Priority to US09/719,033 priority patent/US6376681B1/en
Publication of WO2000002855A2 publication Critical patent/WO2000002855A2/en
Publication of WO2000002855A3 publication Critical patent/WO2000002855A3/en

Links

Classifications

    • 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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

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

Abstract

A multi-step method of synthesizing ketorolac, an analgesic compound, is shown. Several of the reactions and intermediate compounds are novel. The reaction sequence begins with the known compound N-2-bromoethylpyrrole.
PCT/US1999/015496 1998-07-10 1999-07-08 Synthesis of compounds useful in the manufacture of ketorolac WO2000002855A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DE69930940T DE69930940T2 (en) 1998-07-10 1999-07-08 SYNTHESIS OF COMPOUNDS FOR THE PREPARATION OF KETOROLAC
EP99937220A EP1097152B1 (en) 1998-07-10 1999-07-08 Synthesis of compounds useful in the manufacture of ketorolac
JP2000559086A JP2002520313A (en) 1998-07-10 1999-07-08 Synthesis of compounds useful for the production of ketorolac
AU52096/99A AU5209699A (en) 1998-07-10 1999-07-08 Synthesis of compounds useful in the manufacture of ketorolac
US09/719,033 US6376681B1 (en) 1998-07-10 1999-07-08 Synthesis of compounds useful in the manufacture of ketorolac

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9240898P 1998-07-10 1998-07-10
US60/092,408 1998-07-10

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US09/719,033 A-371-Of-International US6376681B1 (en) 1998-07-10 1999-07-08 Synthesis of compounds useful in the manufacture of ketorolac
US10/072,649 Division US6489491B2 (en) 1998-07-10 2002-02-05 Synthesis of compounds useful in the manufacture of ketorolac

Publications (2)

Publication Number Publication Date
WO2000002855A2 WO2000002855A2 (en) 2000-01-20
WO2000002855A3 true WO2000002855A3 (en) 2000-02-24

Family

ID=22233070

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/015496 WO2000002855A2 (en) 1998-07-10 1999-07-08 Synthesis of compounds useful in the manufacture of ketorolac

Country Status (8)

Country Link
US (3) US6376681B1 (en)
EP (1) EP1097152B1 (en)
JP (1) JP2002520313A (en)
AT (1) ATE323703T1 (en)
AU (1) AU5209699A (en)
DE (1) DE69930940T2 (en)
ES (1) ES2259475T3 (en)
WO (1) WO2000002855A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050070906A1 (en) * 1999-11-30 2005-03-31 Ron Clark Endosteal tibial ligament fixation with adjustable tensioning
GB0000569D0 (en) 2000-01-12 2000-03-01 Ici Plc Organometallic compositions
GB0112901D0 (en) 2001-05-29 2001-07-18 Ici Plc Organometallic compositions
US7341502B2 (en) * 2002-07-18 2008-03-11 Micron Technology, Inc. Methods and systems for planarizing workpieces, e.g., microelectronic workpieces
LU91605B1 (en) 2009-09-07 2011-03-08 Terra Nobilis S A Method for securing the storage of long-lived radioactive waste.
CN113087626A (en) * 2020-01-09 2021-07-09 鲁南制药集团股份有限公司 Ketorolac tromethamine intermediate compound VI
CN113087619A (en) * 2020-01-09 2021-07-09 鲁南制药集团股份有限公司 Ketorolac tromethamine intermediate compound
CN113087710A (en) * 2020-01-09 2021-07-09 鲁南制药集团股份有限公司 Preparation method of ketorolac tromethamine intermediate
CN112898307A (en) * 2021-02-07 2021-06-04 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) Ketorolac impurity C and preparation method and application thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4089969A (en) * 1976-07-14 1978-05-16 Syntex (U.S.A.) Inc. 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof
EP0000649A1 (en) * 1977-07-25 1979-02-07 Syntex (U.S.A.) Inc. 5-substituted-1,2-dihydro-3H-pyrrolo(1,2-a)pyrrole-1-carbonitriles and process for their conversion to the corresponding 1-carboxylic acids
US4458081A (en) * 1980-10-20 1984-07-03 Syntex (U.S.A.) Inc. 5-Aroyl 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-decarboxylates
EP0486807A1 (en) * 1990-10-12 1992-05-27 Syntex (U.S.A.) Inc. Process for preparing 5-aroyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylates
US5532381A (en) * 1994-11-16 1996-07-02 Dong Kook Pharmaceutical Co., Ltd. Process for preparing pyrrolizine derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH616808B (en) * 1978-06-14 Piquerez Sa Ervin METHOD FOR MANUFACTURING A WATCH BOX AND WATCH BOX OBTAINED BY THIS PROCESS.

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4089969A (en) * 1976-07-14 1978-05-16 Syntex (U.S.A.) Inc. 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof
EP0000649A1 (en) * 1977-07-25 1979-02-07 Syntex (U.S.A.) Inc. 5-substituted-1,2-dihydro-3H-pyrrolo(1,2-a)pyrrole-1-carbonitriles and process for their conversion to the corresponding 1-carboxylic acids
US4458081A (en) * 1980-10-20 1984-07-03 Syntex (U.S.A.) Inc. 5-Aroyl 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-decarboxylates
EP0486807A1 (en) * 1990-10-12 1992-05-27 Syntex (U.S.A.) Inc. Process for preparing 5-aroyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylates
US5532381A (en) * 1994-11-16 1996-07-02 Dong Kook Pharmaceutical Co., Ltd. Process for preparing pyrrolizine derivatives

Also Published As

Publication number Publication date
US6559319B2 (en) 2003-05-06
US20020137945A1 (en) 2002-09-26
WO2000002855A2 (en) 2000-01-20
US6376681B1 (en) 2002-04-23
DE69930940T2 (en) 2006-12-14
EP1097152B1 (en) 2006-04-19
EP1097152A2 (en) 2001-05-09
ES2259475T3 (en) 2006-10-01
JP2002520313A (en) 2002-07-09
ATE323703T1 (en) 2006-05-15
US20030036660A1 (en) 2003-02-20
DE69930940D1 (en) 2006-05-24
US6489491B2 (en) 2002-12-03
AU5209699A (en) 2000-02-01

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