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WO2004004730A3 - 2-aminopyrazine derivatives as inhibitors of cyclin dependent kinases for the treatment of proliferative disorders - Google Patents

2-aminopyrazine derivatives as inhibitors of cyclin dependent kinases for the treatment of proliferative disorders Download PDF

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Publication number
WO2004004730A3
WO2004004730A3 PCT/GB2003/002905 GB0302905W WO2004004730A3 WO 2004004730 A3 WO2004004730 A3 WO 2004004730A3 GB 0302905 W GB0302905 W GB 0302905W WO 2004004730 A3 WO2004004730 A3 WO 2004004730A3
Authority
WO
WIPO (PCT)
Prior art keywords
ring members
cyclin dependent
dependent kinases
inhibitors
group
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/GB2003/002905
Other languages
French (fr)
Other versions
WO2004004730A2 (en
Inventor
Alison Jo-Anne Woolford
Valerio Berdini
Marc Oreilly
Alessandro Padova
Gordon Saxty
Paul Graham Wyatt
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.)
Astex Technology Ltd
Original Assignee
Astex Technology Ltd
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 Astex Technology Ltd filed Critical Astex Technology Ltd
Priority to AU2003242860A priority Critical patent/AU2003242860A1/en
Publication of WO2004004730A2 publication Critical patent/WO2004004730A2/en
Publication of WO2004004730A3 publication Critical patent/WO2004004730A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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

Abstract

The invention provides a compound of the general formula (I) wherein R1 is selected from hydrogen, cycloalkyl and cycloalkenyl having 3 to 7 ring members; phenyl-C1-4 alkyl or a group R4-A-CH2-, R2 is selected from aryl and heteroaryl having five to twelve ring members; cycloalkyl and cycloalkenyl having 3 to 7 ring members; a group (CR6R7)pE-R8, or R1 and R2 together with the nitrogen atom to which they are attached form a heterocyclic group having 5 to 10 ring members; R3 is a substituent selected from halogen, CN, N-linked monocyclic nitrogen-containing heterocyclic groups having from 3 to 7 ring members and containing up to three heteroatoms; and a group Ra-Rb. The substituents R4-R, Ra and Rb are defined in claim 1. The compounds have activity as inhibitors of cyclin dependent kinases and are useful in the treatment of disease states and conditions, such as proliferative diseases, mediated by cyclin dependent kinases.
PCT/GB2003/002905 2002-07-06 2003-07-04 2-aminopyrazine derivatives as inhibitors of cyclin dependent kinases for the treatment of proliferative disorders Ceased WO2004004730A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003242860A AU2003242860A1 (en) 2002-07-06 2003-07-04 2-aminopyrazine derivatives as inhibitors of cyclin dependent kinases for the treatment of proliferative disorders

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0215775A GB0215775D0 (en) 2002-07-06 2002-07-06 Pharmaceutical compounds
GB0215775.8 2002-07-06

Publications (2)

Publication Number Publication Date
WO2004004730A2 WO2004004730A2 (en) 2004-01-15
WO2004004730A3 true WO2004004730A3 (en) 2004-04-29

Family

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Family Applications (1)

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PCT/GB2003/002905 Ceased WO2004004730A2 (en) 2002-07-06 2003-07-04 2-aminopyrazine derivatives as inhibitors of cyclin dependent kinases for the treatment of proliferative disorders

Country Status (3)

Country Link
AU (1) AU2003242860A1 (en)
GB (1) GB0215775D0 (en)
WO (1) WO2004004730A2 (en)

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EP1511742B1 (en) 2002-05-23 2010-02-03 Cytopia Research Pty Ltd Kinase inhibitors
US20080194574A1 (en) * 2003-12-16 2008-08-14 Axxima Pharmaceuticals Ag Pyrazine Derivatives As Effective Compounds Against Infectious Diseases
AU2005230847B2 (en) * 2004-03-31 2012-11-08 Exelixis, Inc. Anaplastic lymphoma kinase modulators and methods of use
AU2005252160A1 (en) 2004-04-13 2005-12-22 Astellas Pharma Inc. Polycyclic pyrazines as potassium ion channel modulators
JP2008517061A (en) * 2004-10-20 2008-05-22 コンパス ファーマシューティカルズ リミティド ライアビリティ カンパニー Compounds as antitumor agents and their use
GB0719644D0 (en) * 2007-10-05 2007-11-14 Cancer Rec Tech Ltd Therapeutic compounds and their use
DE102008022788A1 (en) * 2008-05-08 2009-11-12 Süd-Chemie AG New 2,6-pyrazine bridged transition metal carbene complex useful as a catalyst for oxidation of hydrocarbons
JP5756457B2 (en) * 2009-04-06 2015-07-29 アジオス ファーマシューティカルズ， インコーポレイテッド Pyruvate kinase M2 modulators, therapeutic compositions and related methods of use
PL2427441T3 (en) 2009-05-04 2017-06-30 Agios Pharmaceuticals, Inc. Pkm2 activators for use in the treatment of cancer
JP5764555B2 (en) 2009-06-29 2015-08-19 アジオス ファーマシューティカルズ， インコーポレイテッド Therapeutic compositions and related methods of use
NZ622505A (en) 2009-06-29 2015-12-24 Agios Pharmaceuticals Inc Therapeutic compounds and compositions
JP5837091B2 (en) 2010-12-17 2015-12-24 アジオス ファーマシューティカルズ， インコーポレイテッド Novel N- (4- (azetidine-1-carbonyl) phenyl)-(hetero-) arylsulfonamide derivatives as modulators of pyruvate kinase M2 (PKM2)
WO2012088314A1 (en) 2010-12-21 2012-06-28 Agios Pharmaceuticals, Inc. Bicyclic pkm2 activators
TWI549947B (en) 2010-12-29 2016-09-21 阿吉歐斯製藥公司 Therapeutic compounds and compositions
WO2012151440A1 (en) 2011-05-03 2012-11-08 Agios Pharmaceuticals, Inc. Pyruvate kinase activators for use for increasing lifetime of the red blood cells and treating anemia
PT2704721T (en) 2011-05-03 2018-06-14 Agios Pharmaceuticals Inc Pyruvate kinase activators for use in therapy
JP2016506921A (en) 2013-01-30 2016-03-07 バイエル ファーマ アクチエンゲゼルシャフト Amino-substituted isothiazole
WO2014139144A1 (en) 2013-03-15 2014-09-18 Agios Pharmaceuticals, Inc. Therapeutic compounds and compositions
CN105985322A (en) * 2015-03-03 2016-10-05 苏州翔实医药发展有限公司 Amino pyrazine compound and application thereof
RS64777B1 (en) 2015-06-11 2023-11-30 Agios Pharmaceuticals Inc Methods of using pyruvate kinase activators
CN112142716B (en) * 2020-10-29 2021-08-31 山东新时代药业有限公司 5-membered heteroaryl substituted pyrazine derivative and application thereof
WO2024050374A2 (en) * 2022-09-02 2024-03-07 Miralogx Llc Anti-inflammatory compounds, pharmaceutical compositions, and methods of treating hemochromatosis, and other disorders

Citations (10)

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EP0254259A2 (en) * 1986-07-21 1988-01-27 Otsuka Pharmaceutical Factory, Inc. p-Aminophenol derivatives
WO1990014338A1 (en) * 1989-05-20 1990-11-29 Fisons Plc Anti-inflammatory 4-aminophenol derivatives
WO1999062885A1 (en) * 1998-06-05 1999-12-09 Boehringer Ingelheim Pharmaceuticals, Inc. Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents
WO2001030749A1 (en) * 1999-10-28 2001-05-03 New Pharma Research Sweden Ab Novel compounds
WO2001036408A1 (en) * 1999-11-15 2001-05-25 New Pharma Research Sweden Ab Compounds with antibacterial and antiparasitic properties
WO2002024681A2 (en) * 2000-09-20 2002-03-28 Ortho-Mcneil Pharmaceutical, Inc. Pyrazine derivatives as modulators of tyrosine kinases
WO2002040456A1 (en) * 2000-11-20 2002-05-23 Biovitrum Ab Piperazinylpyrazine compounds as agonist or antagonist of serotonin 5ht-2 receptor
WO2002060492A1 (en) * 2001-01-30 2002-08-08 Cytopia Pty Ltd Methods of inhibiting kinases
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WO2003032971A1 (en) * 2001-10-17 2003-04-24 Glaxo Group Limited 5’-acylamino-1,1’-biphenyl-4-carboxamide derivatives and their use as p38 kinase inhibitors

Patent Citations (10)

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EP0254259A2 (en) * 1986-07-21 1988-01-27 Otsuka Pharmaceutical Factory, Inc. p-Aminophenol derivatives
WO1990014338A1 (en) * 1989-05-20 1990-11-29 Fisons Plc Anti-inflammatory 4-aminophenol derivatives
WO1999062885A1 (en) * 1998-06-05 1999-12-09 Boehringer Ingelheim Pharmaceuticals, Inc. Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents
WO2001030749A1 (en) * 1999-10-28 2001-05-03 New Pharma Research Sweden Ab Novel compounds
WO2001036408A1 (en) * 1999-11-15 2001-05-25 New Pharma Research Sweden Ab Compounds with antibacterial and antiparasitic properties
WO2002024681A2 (en) * 2000-09-20 2002-03-28 Ortho-Mcneil Pharmaceutical, Inc. Pyrazine derivatives as modulators of tyrosine kinases
WO2002040456A1 (en) * 2000-11-20 2002-05-23 Biovitrum Ab Piperazinylpyrazine compounds as agonist or antagonist of serotonin 5ht-2 receptor
WO2002060492A1 (en) * 2001-01-30 2002-08-08 Cytopia Pty Ltd Methods of inhibiting kinases
WO2003031406A2 (en) * 2001-10-12 2003-04-17 Irm Llc Kinase inhibitor scaffolds and methods for their preparation
WO2003032971A1 (en) * 2001-10-17 2003-04-24 Glaxo Group Limited 5’-acylamino-1,1’-biphenyl-4-carboxamide derivatives and their use as p38 kinase inhibitors

Non-Patent Citations (2)

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Title
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; DING, SHENG ET AL: "A Combinatorial Scaffold Approach toward Kinase-Directed Heterocycle Libraries", XP002257088, retrieved from STN Database accession no. 136:294745 *
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002), 124(8), 1594-1596 *

Also Published As

Publication number Publication date
WO2004004730A2 (en) 2004-01-15
GB0215775D0 (en) 2002-08-14
AU2003242860A8 (en) 2004-01-23
AU2003242860A1 (en) 2004-01-23

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