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WO2008121861A3 - Pyrazole and pyrrole compounds useful in treating iron disorders - Google Patents

Pyrazole and pyrrole compounds useful in treating iron disorders Download PDF

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Publication number
WO2008121861A3
WO2008121861A3 PCT/US2008/058730 US2008058730W WO2008121861A3 WO 2008121861 A3 WO2008121861 A3 WO 2008121861A3 US 2008058730 W US2008058730 W US 2008058730W WO 2008121861 A3 WO2008121861 A3 WO 2008121861A3
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WO
WIPO (PCT)
Prior art keywords
pyrazole
compounds useful
iron disorders
pyrrole compounds
treating iron
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/US2008/058730
Other languages
French (fr)
Other versions
WO2008121861A2 (en
Inventor
Jean-Jacques Cadieux
Jianmin Fu
Rajender Kamboj
Kashinath Sadalapure
Zaihui Zhang
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.)
Xenon Pharmaceuticals Inc
Original Assignee
Xenon Pharmaceuticals Inc
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 Xenon Pharmaceuticals Inc filed Critical Xenon Pharmaceuticals Inc
Publication of WO2008121861A2 publication Critical patent/WO2008121861A2/en
Publication of WO2008121861A3 publication Critical patent/WO2008121861A3/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
    • C07D401/04—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/38—Nitrogen atoms
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • 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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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

Abstract

This invention is directed to pyrazole and pyrrole compounds, for example, compounds of formula (I): wherein R1, R2, R3 and R4 are as defined herein, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of iron disorders. This invention is also directed to pharmaceutical compositions comprising the compounds and methods of using the compounds to treat iron disorders.
PCT/US2008/058730 2007-03-28 2008-03-28 Pyrazole and pyrrole compounds useful in treating iron disorders Ceased WO2008121861A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US90866007P 2007-03-28 2007-03-28
US60/908,660 2007-03-28

Publications (2)

Publication Number Publication Date
WO2008121861A2 WO2008121861A2 (en) 2008-10-09
WO2008121861A3 true WO2008121861A3 (en) 2008-12-24

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11325903B2 (en) 2016-11-30 2022-05-10 Bantam Pharmaceutical, Llc Substituted pyrazole compounds and methods of using them for treatment of hyperproliferative diseases
US11602526B2 (en) 2015-06-01 2023-03-14 Bantam Pharmaceutical, Llc Substituted pyrazole and pyrrole compounds and methods for using them for inhibition of initiation of translation and treatment of diseases and disorders relating thereto

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WO2008130619A2 (en) * 2007-04-20 2008-10-30 Trustees Of Boston College A composition comprising an inhibitor of pde4 and/or pde7
WO2010005851A1 (en) * 2008-07-08 2010-01-14 Xenon Pharmaceuticals Inc. Combination therapy for treating iron disorders
FR2949466A1 (en) * 2009-08-28 2011-03-04 Sanofi Aventis New 2-pyridin-2-yl-pyrazol-3(2H)-one compounds are hypoxia inducible factor activators useful to treat e.g. lower limb ischemia, angina pectoris, myocardial infarction, atherosclerosis, pulmonary hypertension, glaucoma and kidney diseases
FR2940651B1 (en) * 2008-12-29 2013-05-03 Sanofi Aventis 2-PYRIDIN-2-YL-PYRAZOL-3 (2H) -ONE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC USE AS HIF ACTIVATORS
EP2467361A1 (en) 2009-08-20 2012-06-27 Vifor (International) Ag Novel quinoline-hepcidine antagonists
AR077958A1 (en) 2009-08-27 2011-10-05 Vifor Int Ag ANTOGONIST QUINOXALINONES OF HEPCIDINE
AR077999A1 (en) 2009-09-02 2011-10-05 Vifor Int Ag ANTIGONISTS OF PYRIMIDIN AND TRIAZIN-HEPCIDINE
US20120214798A1 (en) 2009-09-07 2012-08-23 Vifor (International) Ag Novel Ethanediamone Hepcidine Antagonists
AR078278A1 (en) 2009-09-09 2011-10-26 Vifor Int Ag ANTAGONISTS OF TIAZOL AND OXAZOL HEPCIDINE, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND USE OF THE SAME FOR THE TREATMENT OF ANEMIAS AND ILLNESSES ASSOCIATED WITH IRON DEFICIENCIES.
JP5743418B2 (en) * 2010-04-09 2015-07-01 Ｏａｔアグリオ株式会社 Novel pyrazole compound, its production method and pest control agent
US20120214803A1 (en) 2011-02-18 2012-08-23 Vifor (International) Ag Novel Sulfonaminoquinoline Hepcidin Antagonists
KR101302315B1 (en) * 2011-07-19 2013-08-30 이화여자대학교 산학협력단 Composition comprising the pyrezole derivatives for prevention and treatment of respiratory diseases
US9403833B2 (en) 2014-05-14 2016-08-02 Novartis Ag Carboxamide derivatives
US9403810B2 (en) 2014-05-14 2016-08-02 Novartis Ag Carboxamide derivatives
CN104262257A (en) * 2014-10-12 2015-01-07 湖南华腾制药有限公司 Preparation method of pyrazole derivative
CN104557711B (en) * 2014-12-26 2017-12-15 南通大学 The preparation and application of the pyrazoles oxime compound of the structure containing FTS
WO2016109559A2 (en) 2014-12-29 2016-07-07 The United States Of America As Represented By The Secretary, Department Of Health And Human Services Small molecule inhibitors of lactate dehydrogenase and methods of use thereof
CN110769823A (en) * 2016-11-30 2020-02-07 班塔姆制药有限责任公司 Use of substituted pyrazole and pyrrole compounds and methods of treating hyperproliferative disorders
MX2020004994A (en) * 2017-11-15 2020-10-12 Metabomed Ltd Acss2 inhibitors and methods of use thereof.
CN108147996B (en) * 2018-01-12 2021-09-24 扬州大学 A kind of synthetic method of arylmethylene bispyrazole ester monopotassium salt
MY202639A (en) 2018-04-25 2024-05-13 Bayer Ag Novel heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides
MY208580A (en) 2019-07-23 2025-05-16 Bayer Ag Novel heteroaryl-triazole compounds as pesticides
EP4003974A1 (en) 2019-07-23 2022-06-01 Bayer Aktiengesellschaft Novel heteroaryl-triazole compounds as pesticides
AU2021240044A1 (en) * 2020-03-20 2022-11-17 Akebia Therapeutics, Inc. PHD inhibitor compounds, compositions, and use
WO2022040005A1 (en) * 2020-08-17 2022-02-24 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Profilin1:actin inhibitor an anti-angiogenic compound
CN114085152A (en) * 2021-12-02 2022-02-25 华东医药（西安）博华制药有限公司 A kind of method for preparing 2-(4-nitrophenyl) butyric acid

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11602526B2 (en) 2015-06-01 2023-03-14 Bantam Pharmaceutical, Llc Substituted pyrazole and pyrrole compounds and methods for using them for inhibition of initiation of translation and treatment of diseases and disorders relating thereto
US11325903B2 (en) 2016-11-30 2022-05-10 Bantam Pharmaceutical, Llc Substituted pyrazole compounds and methods of using them for treatment of hyperproliferative diseases

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