WO1999043643A3 - Metal-catalyzed arylations and vinylations of hydrazines, hydrazones, hydroxylamines and oximes - Google Patents

Metal-catalyzed arylations and vinylations of hydrazines, hydrazones, hydroxylamines and oximes Download PDF

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Publication number
WO1999043643A3
WO1999043643A3 PCT/US1999/004217 US9904217W WO9943643A3 WO 1999043643 A3 WO1999043643 A3 WO 1999043643A3 US 9904217 W US9904217 W US 9904217W WO 9943643 A3 WO9943643 A3 WO 9943643A3
Authority
WO
WIPO (PCT)
Prior art keywords
hydrazones
hydrazines
vinylations
hydroxylamines
oximes
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/US1999/004217
Other languages
French (fr)
Other versions
WO1999043643A2 (en
Inventor
Stephen L Buchwald
Seble Wagaw
Oliver Geis
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.)
Massachusetts Institute of Technology
Original Assignee
Massachusetts Institute of Technology
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 US09/030,936 external-priority patent/US6235936B1/en
Application filed by Massachusetts Institute of Technology filed Critical Massachusetts Institute of Technology
Priority to DE69904448T priority Critical patent/DE69904448T2/en
Priority to EP99908515A priority patent/EP1058678B1/en
Priority to JP2000533402A priority patent/JP4647780B2/en
Priority to CA2322194A priority patent/CA2322194C/en
Priority to AT99908515T priority patent/ATE229499T1/en
Publication of WO1999043643A2 publication Critical patent/WO1999043643A2/en
Publication of WO1999043643A3 publication Critical patent/WO1999043643A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or 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 to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C07D213/77—Hydrazine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C241/02—Preparation of hydrazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C241/04—Preparation of hydrazides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
    • C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
    • 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
    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Indole Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

A method is provided for the transition metal-catalyzed arylation, or vinylation, of hydrazines, hydrazones, and the like. Additionally, the invention provides a conceptually novel strategy, the cornerstone of which is the transition metal-catalyzed arylation or vinylation method, for the synthesis of indoles, carbazoles, and the like. The methods and strategies of the invention may be utilized in standard, parallel, and combinatorial synthetic protocols.
PCT/US1999/004217 1998-02-26 1999-02-26 Metal-catalyzed arylations and vinylations of hydrazines, hydrazones, hydroxylamines and oximes Ceased WO1999043643A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DE69904448T DE69904448T2 (en) 1998-02-26 1999-02-26 METAL-CATALYZED ARYLATIONS AND VINYLATIONS OF HYDRAZINES, HYDRAZONES, HYDROXYLAMINES AND OXIMES
EP99908515A EP1058678B1 (en) 1998-02-26 1999-02-26 Metal-catalyzed arylations and vinylations of hydrazines, hydrazones, hydroxylamines and oximes
JP2000533402A JP4647780B2 (en) 1998-02-26 1999-02-26 Metal-catalyzed arylation and vinylation of hydrazine, hydrazone, hydroxylamine and oximes
CA2322194A CA2322194C (en) 1998-02-26 1999-02-26 Metal-catalyzed arylations and vinylations of hydrazines, hydrazones, hydroxylamines and oximes
AT99908515T ATE229499T1 (en) 1998-02-26 1999-02-26 METAL-CATALYzed ARYLATIONS AND VINYLATIONS OF HYDRAZINES, HYDRAZONES, HYDROXYLAMINES AND OXIMES

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US09/030,936 US6235936B1 (en) 1998-02-26 1998-02-26 Metal-catalyzed arylations of hydrazines, hydrazones, and related substrates
US5555798A 1998-04-06 1998-04-06
US09/030,936 1998-04-06
US09/055,557 1998-04-06

Publications (2)

Publication Number Publication Date
WO1999043643A2 WO1999043643A2 (en) 1999-09-02
WO1999043643A3 true WO1999043643A3 (en) 1999-10-21

Family

ID=26706608

Family Applications (1)

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PCT/US1999/004217 Ceased WO1999043643A2 (en) 1998-02-26 1999-02-26 Metal-catalyzed arylations and vinylations of hydrazines, hydrazones, hydroxylamines and oximes

Country Status (6)

Country Link
EP (1) EP1058678B1 (en)
JP (1) JP4647780B2 (en)
AT (1) ATE229499T1 (en)
CA (1) CA2322194C (en)
DE (1) DE69904448T2 (en)
WO (1) WO1999043643A2 (en)

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US11844757B2 (en) 2016-01-26 2023-12-19 Intra-Cellular Therapies, Inc. Organic compounds
US12195464B2 (en) 2018-06-06 2025-01-14 Intra-Cellular Therapies, Inc. Lumateperone bis-tosylate salts and crystals and methods for manufacture thereof
US12624036B2 (en) 2012-04-14 2026-05-12 Intra-Cellular Therapies, Inc. Method of treating post-traumatic stress disorder

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US6764858B2 (en) 1999-09-29 2004-07-20 Pharmacia & Upjohn Company Methods for creating a compound library
AU1494401A (en) * 1999-09-29 2001-04-30 Pharmacia & Upjohn Company Methods for creating a compound library and identifying lead chemical templates and ligands for target molecules
US6677160B1 (en) 1999-09-29 2004-01-13 Pharmacia & Upjohn Company Methods for creating a compound library and identifying lead chemical templates and ligands for target molecules
EP1130009A1 (en) * 2000-03-01 2001-09-05 Therascope AG Generation and screening of a dynamic combinatorial library
US6706895B1 (en) 2002-11-14 2004-03-16 Uniroyal Chemical Company, Inc. 4-methoxybiphenyl hydrazone derivatives
CN1835800B (en) 2003-07-25 2010-04-28 旭化成化学株式会社 Oxidation catalyst
FR2899897B1 (en) 2006-04-13 2008-06-27 Oreal SINGLE-PARTICULATE MONOCATIONIC COMPOUNDS OF THE HYDRAZONE TYPE COMPRISING A 2-, 4-PYRIDINIUM OR 2-, 4-QUINOLINIUM PATTERN, THEIR SYNTHESIS, TINCTORIAL COMPOSITIONS COMPRISING SAME, PROCESS FOR COLORING KERATIN FIBERS
CA2679754C (en) 2007-03-12 2018-08-07 Intra-Cellular Therapies, Inc. Substituted heterocycle fused gamma-carbolines synthesis
WO2009000411A1 (en) * 2007-06-26 2008-12-31 Sanofi-Aventis A transition metal catalyzed synthesis of 2h-indazoles
WO2012009699A2 (en) 2010-07-16 2012-01-19 Abbott Laboratories Process for preparing antiviral compounds
BR112013001138A2 (en) 2010-07-16 2016-07-05 Abbvie Inc phosphine binders for catalytic reactions
US8975443B2 (en) 2010-07-16 2015-03-10 Abbvie Inc. Phosphine ligands for catalytic reactions
US9255074B2 (en) 2010-07-16 2016-02-09 Abbvie Inc. Process for preparing antiviral compounds
JP6166996B2 (en) * 2013-09-27 2017-07-19 株式会社日本ファインケム Method for producing hydrazinoarylcarboxylic acids
CA3148303C (en) 2013-12-03 2024-02-27 Intra-Cellular Therapies, Inc. Heterocycle fused gamma-carboline compounds for use in treatment of bipolar disorders
CA2944512C (en) 2014-04-04 2018-04-24 Intra-Cellular Therapies, Inc. Heterocycle fused gamma-carbolines for treatment of central nervous system disorders
CA2944755A1 (en) 2014-04-04 2015-10-08 Intra-Cellular Therapies, Inc. Organic compounds
SI3407889T1 (en) 2016-03-25 2021-09-30 Intra-Cellular Therapies, Inc. Organic compounds and their use in the treatment or prevention of central nervous system disorders
EP3436016B1 (en) 2016-03-28 2022-04-27 Intra-Cellular Therapies, Inc. Novel co-crystals
US10682354B2 (en) 2016-03-28 2020-06-16 Intra-Cellular Therapies, Inc. Compositions and methods
EP3436455A4 (en) 2016-03-28 2019-09-04 Intra-Cellular Therapies, Inc. NEW SALTS AND CRYSTALS
JP7013454B2 (en) 2016-10-12 2022-02-15 イントラ－セルラー・セラピーズ・インコーポレイテッド Amorphous solid dispersion
WO2018126143A1 (en) 2016-12-29 2018-07-05 Intra-Cellular Therapies, Inc. Organic compounds
WO2018126140A1 (en) 2016-12-29 2018-07-05 Intra-Cellular Therapies, Inc. Organic compounds
IL304026B2 (en) 2017-03-24 2024-11-01 Intra Cellular Therapies Inc A PHARMACEUTICAL FORMULATION COMPRISING 1-(4-FLUORO-PHENYL)-4-((6bR,10aS)-2,2-D2-3-METHYL-2,3,6b,9,10,10a-HEXAHYDRO-1H,7H-PYRIDO[3',4':4,5]PYRROLO[1,2,3-de]QUINOXALIN-8-YL)-BUTAN-1-ONE AND USES THEREOF
US11427587B2 (en) 2017-07-26 2022-08-30 Intra-Cellular Therapies, Inc. Organic compounds
JP7223742B2 (en) 2017-07-26 2023-02-16 イントラ－セルラー・セラピーズ・インコーポレイテッド organic compound
IL277504B1 (en) 2018-03-23 2026-02-01 Intra Cellular Therapies Inc (6br,10as)-8-(3-(4-fluorophenoxy)propyl)-6b,7,8,9,10,10a-hexahydro-1h-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-2(3h)-one compounds substituted with deuterium, pharmaceutical composition comprising them and their use
WO2019237037A1 (en) 2018-06-08 2019-12-12 Intra-Cellular Therapies, Inc. Novel methods
US12144808B2 (en) 2018-08-29 2024-11-19 Intra-Cellular Therapies, Inc. Compositions and methods
AU2019328528B2 (en) 2018-08-31 2025-01-23 Intra-Cellular Therapies, Inc. Novel methods
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US4374271A (en) * 1974-12-04 1983-02-15 United States Borax & Chemical Corporation Nitrophenylhydrazine compounds
EP0078768A1 (en) * 1981-11-04 1983-05-11 Ciba-Geigy Ag Process for the catalytic Pd arylation of olefines with aryl halogenides
EP0187285A2 (en) * 1984-12-22 1986-07-16 Bayer Ag Process for the preparation of substituted phenyl hydrazines
EP0224831A2 (en) * 1985-12-05 1987-06-10 Bayer Ag 5-Dichloroacetamido-4-nitro-1-aryl-pyrazoles
EP0790233A2 (en) * 1996-02-16 1997-08-20 Fuji Photo Film Co., Ltd. Method of producing 2-hydrazinonaphtalene compound

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US3867452A (en) * 1970-12-30 1975-02-18 Merrill Wilcox 2-Nitrophenylhydrazines
US4374271A (en) * 1974-12-04 1983-02-15 United States Borax & Chemical Corporation Nitrophenylhydrazine compounds
EP0078768A1 (en) * 1981-11-04 1983-05-11 Ciba-Geigy Ag Process for the catalytic Pd arylation of olefines with aryl halogenides
EP0187285A2 (en) * 1984-12-22 1986-07-16 Bayer Ag Process for the preparation of substituted phenyl hydrazines
EP0224831A2 (en) * 1985-12-05 1987-06-10 Bayer Ag 5-Dichloroacetamido-4-nitro-1-aryl-pyrazoles
EP0790233A2 (en) * 1996-02-16 1997-08-20 Fuji Photo Film Co., Ltd. Method of producing 2-hydrazinonaphtalene compound

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12624036B2 (en) 2012-04-14 2026-05-12 Intra-Cellular Therapies, Inc. Method of treating post-traumatic stress disorder
US12624037B2 (en) 2012-04-14 2026-05-12 Intra-Cellular Therapies, Inc. Method of treating agitation, aggressive behavior, and impulse control disorder
US11844757B2 (en) 2016-01-26 2023-12-19 Intra-Cellular Therapies, Inc. Organic compounds
US12195464B2 (en) 2018-06-06 2025-01-14 Intra-Cellular Therapies, Inc. Lumateperone bis-tosylate salts and crystals and methods for manufacture thereof

Also Published As

Publication number Publication date
JP4647780B2 (en) 2011-03-09
CA2322194C (en) 2011-04-26
EP1058678B1 (en) 2002-12-11
DE69904448D1 (en) 2003-01-23
CA2322194A1 (en) 1999-09-02
DE69904448T2 (en) 2003-10-23
WO1999043643A2 (en) 1999-09-02
EP1058678A2 (en) 2000-12-13
JP2002504535A (en) 2002-02-12
ATE229499T1 (en) 2002-12-15

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