WO2001081306A3 - Azide cyclization-based synthesis and intermediates for spla2 inhibitors - Google Patents

Azide cyclization-based synthesis and intermediates for spla2 inhibitors Download PDF

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Publication number
WO2001081306A3
WO2001081306A3 PCT/US2001/008644 US0108644W WO0181306A3 WO 2001081306 A3 WO2001081306 A3 WO 2001081306A3 US 0108644 W US0108644 W US 0108644W WO 0181306 A3 WO0181306 A3 WO 0181306A3
Authority
WO
WIPO (PCT)
Prior art keywords
intermediates
individually
based synthesis
spla2 inhibitors
compounds
Prior art date
Application number
PCT/US2001/008644
Other languages
French (fr)
Other versions
WO2001081306A2 (en
Inventor
Jason Scott Sawyer
Edward C R Smith
Original Assignee
Lilly Co Eli
Jason Scott Sawyer
Edward C R Smith
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 Lilly Co Eli, Jason Scott Sawyer, Edward C R Smith filed Critical Lilly Co Eli
Priority to AU2001252922A priority Critical patent/AU2001252922A1/en
Publication of WO2001081306A2 publication Critical patent/WO2001081306A2/en
Publication of WO2001081306A3 publication Critical patent/WO2001081306A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—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
    • C07D209/22—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 with an aralkyl radical attached to the ring nitrogen atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A process of preparing sPLA2 inhibitor compounds of formula (X)via an azide cyclization reaction that forms the intermediate indole compounds of formula (II) wherein R2 is R20, -OR20, -SR20, -NR20R20', -C(O)OR20, or -C(O)R20; R3, R4, R5, R6 and R7 are each individually H, halogen, R, -OR, -SR, -NRR', -C(O)R, -C(O)OR, -S(O)R or -S(O)2R; provided that at least one of R4 and R5 is not H; each R, R10 and R20 is individually alkyl, alkenyl, alkynyl, aryl or heterocyclic radical; and each R' and R20' is individually H, alkyl, alkenyl, alkynyl, aryl or heterocyclic radical. The method provides an alternative route to indole-3-glyoxyamide compounds.
PCT/US2001/008644 2000-04-19 2001-04-05 Azide cyclization-based synthesis and intermediates for spla2 inhibitors WO2001081306A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001252922A AU2001252922A1 (en) 2000-04-19 2001-04-05 Azide cyclization-based synthesis and intermediates for spla2 inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US19818200P 2000-04-19 2000-04-19
US60/198,182 2000-04-19

Publications (2)

Publication Number Publication Date
WO2001081306A2 WO2001081306A2 (en) 2001-11-01
WO2001081306A3 true WO2001081306A3 (en) 2002-05-02

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/008644 WO2001081306A2 (en) 2000-04-19 2001-04-05 Azide cyclization-based synthesis and intermediates for spla2 inhibitors

Country Status (2)

Country Link
AU (1) AU2001252922A1 (en)
WO (1) WO2001081306A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8277849B2 (en) 2006-01-19 2012-10-02 Solazyme, Inc. Microalgae-derived compositions for improving the health and appearance of skin
JP5406716B2 (en) 2006-08-07 2014-02-05 アイアンウッド ファーマシューティカルズ インコーポレイテッド Indole compounds
AR084433A1 (en) 2010-12-22 2013-05-15 Ironwood Pharmaceuticals Inc FAAH INHIBITORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
CN104621106B (en) * 2015-01-28 2017-07-14 云南省烟草公司玉溪市公司 Application and preparation method of the 4 methoxy-Indole solution in preventing and treating tobacco black shank
WO2017163263A1 (en) 2016-03-22 2017-09-28 Council Of Scientific & Industrial Research Indole derivatives, preparation and use thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996035805A2 (en) * 1995-05-09 1996-11-14 Institut National De La Sante Et De La Recherche Medicale (Inserm) Tripeptidylpeptidase inhibitors
US5654326A (en) * 1994-04-01 1997-08-05 Eli Lilly And Company 1H-indole-3-glyoxylamide SPLA2 inhibitors
WO1998042343A1 (en) * 1997-03-26 1998-10-01 Eli Lilly And Company Method for treatment of chronic bronchitis

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5654326A (en) * 1994-04-01 1997-08-05 Eli Lilly And Company 1H-indole-3-glyoxylamide SPLA2 inhibitors
WO1996035805A2 (en) * 1995-05-09 1996-11-14 Institut National De La Sante Et De La Recherche Medicale (Inserm) Tripeptidylpeptidase inhibitors
WO1998042343A1 (en) * 1997-03-26 1998-10-01 Eli Lilly And Company Method for treatment of chronic bronchitis

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
ALLEN ET AL, SYNTH. COMMUN., vol. 22, no. 14, 1992, pages 2077 - 2102 *
CHEMICAL AND PHARMACEUTICAL BULLETIN., vol. 47, no. 9, 1999, PHARMACEUTICAL SOCIETY OF JAPAN. TOKYO., JP, pages 1227 - 1231, ISSN: 0009-2363 *
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002186627 *
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002186629 *
KAZUHIRO ET AL: "Synthetic utility of tert-Butyl Azidoacetate on the Hemetsberger-Knittel reaction", CHEMICAL AND PHARMACEUTICAL BULLETIN., vol. 47, no. 9, 1999, PHARMACEUTICAL SOCIETY OF JAPAN. TOKYO., JP, pages 1227 - 1231, XP002187152, ISSN: 0009-2363 *
KIM P T ET AL: "SYNTHESE DE DERIVES INDOLIQUES SUBSTITUES IN 7", JOURNAL OF HETEROCYCLIC CHEMISTRY, HETEROCORPORATION. PROVO, US, vol. 18, no. 7, 1 November 1981 (1981-11-01), pages 1373 - 1377, XP000674275, ISSN: 0022-152X *
TANI M ET AL: "REGIOSELECTIVE BROMINATION OF METHOXY DERIVATIVES OF ETHYL INDOLE-2-CARBOXYLATE USYNTHETIC STUDIES OF INDOLES AND RELATED COMPOUNDS", HETEROCYCLES, vol. 34, no. 12, 1992, pages 2349 - 2362, XP000674898, ISSN: 0006-3002 *

Also Published As

Publication number Publication date
AU2001252922A1 (en) 2001-11-07
WO2001081306A2 (en) 2001-11-01

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