WO2001044182A3 - New synthesis of spla2 inhibitors - Google Patents

New synthesis of spla2 inhibitors Download PDF

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Publication number
WO2001044182A3
WO2001044182A3 PCT/US2000/032446 US0032446W WO0144182A3 WO 2001044182 A3 WO2001044182 A3 WO 2001044182A3 US 0032446 W US0032446 W US 0032446W WO 0144182 A3 WO0144182 A3 WO 0144182A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
individually
new synthesis
spla2 inhibitors
Prior art date
Application number
PCT/US2000/032446
Other languages
French (fr)
Other versions
WO2001044182A2 (en
Inventor
Douglas Wade Beight
Jason Scott Sawyer
Original Assignee
Lilly Co Eli
Douglas Wade Beight
Jason Scott Sawyer
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, Douglas Wade Beight, Jason Scott Sawyer filed Critical Lilly Co Eli
Priority to AU22521/01A priority Critical patent/AU2252101A/en
Publication of WO2001044182A2 publication Critical patent/WO2001044182A2/en
Publication of WO2001044182A3 publication Critical patent/WO2001044182A3/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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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

Abstract

A method of making a compound, comprises deprotecting a compound of formula (I), to form the compound of formula (II); where formula (I) isand, formula (II) isand where Rr is H, R10 or -C(O)R10; R2 is R20 -OR20, -SR20, -NR20R20'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; each R' and R20' is individually H, alkyl, alkenyl, alkynyl, aryl or heterocyclic radical; and P is a protecting group. The method provides an alternative route to indole-3-glyoxyamide compounds.
PCT/US2000/032446 1999-12-16 2000-12-11 New synthesis of spla2 inhibitors WO2001044182A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU22521/01A AU2252101A (en) 1999-12-16 2000-12-11 New synthesis of SPLA2 inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17123699P 1999-12-16 1999-12-16
US60/171,236 1999-12-16

Publications (2)

Publication Number Publication Date
WO2001044182A2 WO2001044182A2 (en) 2001-06-21
WO2001044182A3 true WO2001044182A3 (en) 2002-03-07

Family

ID=22623044

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/032446 WO2001044182A2 (en) 1999-12-16 2000-12-11 New synthesis of spla2 inhibitors

Country Status (2)

Country Link
AU (1) AU2252101A (en)
WO (1) WO2001044182A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7781478B2 (en) 2004-07-14 2010-08-24 Ptc Therapeutics, Inc. Methods for treating hepatitis C
EA018724B1 (en) 2006-08-07 2013-10-30 Айронвуд Фармасьютикалз, Инк. Indole compounds
CN101838232B (en) * 2009-07-07 2012-02-22 爱斯医药科技(南京)有限公司 Preparation method for varespladib
SG182662A1 (en) 2010-01-28 2012-08-30 Harvard College Compositions and methods for enhancing proteasome activity
AR084433A1 (en) 2010-12-22 2013-05-15 Ironwood Pharmaceuticals Inc FAAH INHIBITORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
WO2012154967A1 (en) 2011-05-12 2012-11-15 Proteostasis Therapeutics, Inc. Proteostasis regulators
WO2014116228A1 (en) 2013-01-25 2014-07-31 President And Fellows Of Harvard College Usp14 inhibitors for treating or preventing viral infections
JP2016531874A (en) 2013-09-26 2016-10-13 ファーマケア，インク． Autotaxin inhibitor compounds
WO2015073528A1 (en) 2013-11-12 2015-05-21 Proteostasis Therapeutics, Inc. Proteasome activity enhancing compounds

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
ADAMS ET AL.: "Quinone imides", J. AM. CHEM. SOC., vol. 80, 1958, pages 3291 - 3, XP002174613 *
CHIEN ET AL: "A novel synthesis of 1-acylindoxyls", CHEM. PHARM. BULL., vol. 34, no. 4, 1986, pages 1493 - 6, XP002174615 *
CLARK ET AL: "Preparation of Indoles and Oxindoles from N-(tert-Butoxycarbonyl)-2-alkylanilines", SYNTHESIS, vol. 10, 1991, pages 871 - 8, XP002174610 *
COATES ET AL.: "Decarboxylative 1-Aza-1'-oxa[3,3]Sigmatropic Rearrangements of Enolizable or Enolized N-Aryl-N,O,diacylhydroxylamines to o-(N-Acylamino)aryl Ketones, Esters and Amides", J. AM. CHEM. SOC., vol. 99, 1977, pages 2355 - 7, XP002174611 *
DILLARD ET AL.: "Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A2. 1. Indole-3-acetamides", J. MED. CHEM., vol. 39, 1996, pages 5119 - 36, XP002174609 *
DRAHEIM ET AL.: "Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A2. 3. Indole-3-glyoxamides", J. MED. CHEM., vol. 39, 1966, pages 5159 - 75, XP002174612 *
MOHRI ET AL.: "Meldrum's acid in organic synthesis", CHEM. PHAR. BULL, vol. 30, no. 9, 1982, pages 3097 - 3105, XP002174614 *
MOHRI ET AL: "Meldrum's acid in organic synthesis", HETEROCYCLES, vol. 19, no. 3, 1982, pages 515 - 20, XP001015692 *
RANER ET AL.: "Reactions of Epoxides derived form 2'-(3''-methylbut-2-enyl)trifluoroaccetanilides", AUST. J. CHEM., vol. 43, no. 3, 1990, pages 609 - 16, XP001015687 *

Also Published As

Publication number Publication date
AU2252101A (en) 2001-06-25
WO2001044182A2 (en) 2001-06-21

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