WO2001014374A3 - Processes for the prepration of exo- and endo-indolotropanes - Google Patents

Processes for the prepration of exo- and endo-indolotropanes Download PDF

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Publication number
WO2001014374A3
WO2001014374A3 PCT/EP2000/007697 EP0007697W WO0114374A3 WO 2001014374 A3 WO2001014374 A3 WO 2001014374A3 EP 0007697 W EP0007697 W EP 0007697W WO 0114374 A3 WO0114374 A3 WO 0114374A3
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxycarbonyl
carboxy
mono
alkoxy
Prior art date
Application number
PCT/EP2000/007697
Other languages
French (fr)
Other versions
WO2001014374A2 (en
Inventor
Ian Thomson Forbes
Original Assignee
Smithkline Beecham Plc
Ian Thomson Forbes
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 Smithkline Beecham Plc, Ian Thomson Forbes filed Critical Smithkline Beecham Plc
Priority to AU72730/00A priority Critical patent/AU7273000A/en
Publication of WO2001014374A2 publication Critical patent/WO2001014374A2/en
Publication of WO2001014374A3 publication Critical patent/WO2001014374A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

Novel processes for the stereoselective preparation of exo- and endo- indolotropanes of formulae (IA) and (IB) wherein: R1 is hydrogen or (C¿1-6?)alkyl; R?2 and R3¿, which may be the same or different, are selected from the group consisting of hydrogen, halogen, cyano, (C¿1-6?)alkyl, (C3-7)cycloalkyl, (C1-6)alkoxy, halo(C1-6)alkyl, hydroxy, oxo, amino, mono- or di-(C1-6)alkylamino, acylamino, nitro, carboxy, (C1-6)alkoxycarbonyl, (C1-6)alkenyloxycarbonyl, (C1-6)alkoxycarbonyl(C1-6)alkyl, carboxy(C1-6)alkyl, (C1-6)alkylcarbonyloxy, carboxy(C1-6)alkyloxy, (C1-6)alkoxycarbonyl(C1-6)alkoxy, (C1-6)alkylthio, (C1-6)alkylsulphinyl, (C1-6)alkylsulphonyl, sulphamoyl, mono- and di-(C1-6)-alkylsulphamoyl, carbamoyl, mono- and di-(C1-6)alkylcarbamoyl, (C1-6)alkylsulphonamido, arylsulphonamido, aryl, aryl(C1-6)alkyl, aryl(C1-6)alkoxy, aryloxy, and heterocyclyl; Y is hydrogen, a nitrogen protecting group or an organic substituent; and Nq represents optional ring nitrogen atoms in positions 4, 5, 6, and 7; wherein q is O, 1 or 2.
PCT/EP2000/007697 1999-08-20 2000-08-08 Processes for the prepration of exo- and endo-indolotropanes WO2001014374A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU72730/00A AU7273000A (en) 1999-08-20 2000-08-08 Novel processes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9919843.4 1999-08-20
GBGB9919843.4A GB9919843D0 (en) 1999-08-20 1999-08-20 Novel compounds

Publications (2)

Publication Number Publication Date
WO2001014374A2 WO2001014374A2 (en) 2001-03-01
WO2001014374A3 true WO2001014374A3 (en) 2001-10-11

Family

ID=10859582

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/007697 WO2001014374A2 (en) 1999-08-20 2000-08-08 Processes for the prepration of exo- and endo-indolotropanes

Country Status (3)

Country Link
AU (1) AU7273000A (en)
GB (1) GB9919843D0 (en)
WO (1) WO2001014374A2 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9345708B2 (en) 2009-06-17 2016-05-24 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication
US9394302B2 (en) 2011-08-01 2016-07-19 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2013006836A (en) 2010-12-16 2013-09-26 Vertex Pharma Inhibitors of influenza viruses replication.
ES2741444T3 (en) 2013-11-13 2020-02-11 Vertex Pharma Inhibitors of influenza virus replication
ES2684755T3 (en) 2013-11-13 2018-10-04 Vertex Pharmaceuticals Incorporated Methods for preparing influenza virus replication inhibitors
JP6857617B2 (en) 2015-05-13 2021-04-14 バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ Influenza virus replication inhibitor
JP6704416B2 (en) 2015-05-13 2020-06-03 バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ Methods for preparing inhibitors of influenza virus replication

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999065492A1 (en) * 1998-06-19 1999-12-23 Eli Lilly And Company Inhibition of serotonin reuptake
WO2000004017A1 (en) * 1998-07-15 2000-01-27 Merck Sharp & Dohme Limited Azabicycle-substituted phenylindole derivatives as ligands for 5-ht2a receptors

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999065492A1 (en) * 1998-06-19 1999-12-23 Eli Lilly And Company Inhibition of serotonin reuptake
WO2000004017A1 (en) * 1998-07-15 2000-01-27 Merck Sharp & Dohme Limited Azabicycle-substituted phenylindole derivatives as ligands for 5-ht2a receptors

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
FORBES I T: "Highly stereoselective synthesis of exo and endo indolotropanes", TETRAHEDRON LETTERS,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 40, no. 52, 24 December 1999 (1999-12-24), pages 9293 - 9295, XP004183654, ISSN: 0040-4039 *
FRETER K: "3-CYCLOALKENYLINDOLES", JOURNAL OF ORGANIC CHEMISTRY,US,AMERICAN CHEMICAL SOCIETY. EASTON, vol. 40, no. 17, 22 August 1975 (1975-08-22), pages 2525 - 2529, XP000612178, ISSN: 0022-3263 *
JUNKO NAKAO: "Trialkylmanganate-Induced Cyclization of Allyl 2-Iodophenyl Ether, N,N-Diallyl-2-iodoaniline, and alfa-Iodo Acetal", JOURNAL OF ORGANIC CHEMISTRY, 1997, pages 1910 - 1911, XP002165072 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9345708B2 (en) 2009-06-17 2016-05-24 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication
US9518056B2 (en) 2009-06-17 2016-12-13 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication
US9394302B2 (en) 2011-08-01 2016-07-19 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication

Also Published As

Publication number Publication date
WO2001014374A2 (en) 2001-03-01
GB9919843D0 (en) 1999-10-27
AU7273000A (en) 2001-03-19

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