ES2187025T3 - Nuevos agentes quelantes de hierro (iii) activos via oral. - Google Patents

Nuevos agentes quelantes de hierro (iii) activos via oral.

Info

Publication number
ES2187025T3
ES2187025T3 ES98922968T ES98922968T ES2187025T3 ES 2187025 T3 ES2187025 T3 ES 2187025T3 ES 98922968 T ES98922968 T ES 98922968T ES 98922968 T ES98922968 T ES 98922968T ES 2187025 T3 ES2187025 T3 ES 2187025T3
Authority
ES
Spain
Prior art keywords
hydrogen
aryl
group
aralkyl
alkyl
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.)
Expired - Lifetime
Application number
ES98922968T
Other languages
English (en)
Inventor
Robert Charles Hider
Gary Stuart Tilbrook
Zudong Liu
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.)
BTG International Ltd
Original Assignee
BTG International 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 BTG International Ltd filed Critical BTG International Ltd
Application granted granted Critical
Publication of ES2187025T3 publication Critical patent/ES2187025T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06—Antianaemics
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
    • 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
    • C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Se presenta un nuevo compuesto 3-hidroxipiridin-4-ona de la fórmula (I), en la que R es hidrógeno o un grupo que es eliminado metabólicamente in vivo para suministrar un compuesto hidróxido libre, R{sup,1} es un grupo hidrocarburo alifático o un grupo hidrocarburo alifático sustituido por un grupo hidróxido o un éster de ácido carboxílico, un éster de ácido sulfo o un éter alcóxido C{sub,6} o aralcóxido C{sub, 7-10} del mismo, R{sup,3} se selecciona entre hidrógeno y alquilo C{sub,1-6} y R{sup,4} se selecciona entre hidrógeno y alquilo C{sub,1-6ç, alquilo C{sub,1-6} y un grupo como el descrito para R{sup,2}; que se caracteriza en que R{sup,2} se selecciona entre los grupos (i) -CONH-R{sup,5}, (ii) -CH{sub,2}NHCO-R{sup,5}, (iii) -SO{sub,2}NH-R{sup,5}, (iv) -CH{sub,2}NHSO{sub,2}R{sup,5}, (v) -CR{sup,6}R{sup,6}OR{sup,7}, (viii) -CONHCOR{sup,5}, en donde R{sup,5} se selecciona entre hidrógeno y alquilo C{sub,1-13}, arilo y aralquilo C{sub,7-13} opcionalmente sustituidos por hidróxido, alcóxidoo aralcóxido, R{sup,6} se selecciona independiente entre hidrógeno, alquilo C{sub,1-13}, arilo y aralquilo C{sub, 7-13} y R{sup,7} se selecciona entre hidrógeno, alquilo C{sub,1-13}, arilo y aralquilo C{sub,7-13}; también se presenta una sal farmacológicamente aceptable del compuesto con la condición de que cuando R{sup,7} sea hidrógeno, R{sup,6} no se seleccione entre arilo y con la condición de que el compuesto no sea 1-etil-2(1''-hidroxietil)-3-hidroxipiridin-4-ona.
ES98922968T 1997-05-29 1998-05-26 Nuevos agentes quelantes de hierro (iii) activos via oral. Expired - Lifetime ES2187025T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GBGB9711093.6A GB9711093D0 (en) 1997-05-29 1997-05-29 Novel orally active iron (III) chelators

Publications (1)

Publication Number Publication Date
ES2187025T3 true ES2187025T3 (es) 2003-05-16

Family

ID=10813233

Family Applications (1)

Application Number Title Priority Date Filing Date
ES98922968T Expired - Lifetime ES2187025T3 (es) 1997-05-29 1998-05-26 Nuevos agentes quelantes de hierro (iii) activos via oral.

Country Status (12)

Country Link
US (2) US6335353B1 (es)
EP (1) EP0984934B1 (es)
JP (1) JP2002500663A (es)
AT (1) ATE230728T1 (es)
AU (1) AU751600B2 (es)
CA (1) CA2287907C (es)
DE (1) DE69810619T2 (es)
DK (1) DK0984934T3 (es)
ES (1) ES2187025T3 (es)
GB (1) GB9711093D0 (es)
WO (1) WO1998054138A1 (es)
ZA (1) ZA984635B (es)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7592304B2 (en) 1999-10-01 2009-09-22 Dmi Life Sciences, Inc. Metal-binding compounds and uses therefor
KR20100075503A (ko) 1999-10-01 2010-07-02 디엠아이 바이오사이언시스, 인크 금속 결합 화합물 및 그의 용도
US7632803B2 (en) 1999-10-01 2009-12-15 Dmi Life Sciences, Inc. Metal-binding compounds and uses therefor
US6426418B1 (en) 2001-11-02 2002-07-30 Apotex, Inc. Processes for the manufacturing of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide
JP2005516987A (ja) 2002-02-05 2005-06-09 ブリストル−マイヤーズ　スクイブ　カンパニー Ｎ−置換された３−ヒドロキシ−４−ピリジノン化合物およびそれを含む医薬
AU2003282337B2 (en) 2002-11-07 2009-07-16 Technion Research And Development Foundation Ltd. Neuroprotective iron chelators and pharmaceutical compositions comprising them
NZ529657A (en) * 2003-11-20 2004-07-30 Apotex Inc Iron chelating cycloalkyl derivatives of 3-hydroxy-4-pyridinones
CA2488034C (en) * 2004-11-19 2009-10-06 Apotex Inc. Process for the manufacture of 3-hydroxy-n-alkyl-1-cycloalkyl-6-alkyl-4-oxo-1,4-dihydropyridine-2-carboxamide and its related analogues
GB0506677D0 (en) * 2005-04-01 2005-05-11 Btg Int Ltd Iron modulators
CA2681545C (en) 2007-03-28 2013-10-01 Apotex Technologies Inc. Fluorinated derivatives of deferiprone
GB0803019D0 (en) * 2008-02-19 2008-03-26 Btg Int Ltd Fluorinated compounds
PL2268282T3 (pl) 2008-04-25 2015-04-30 Apotex Tech Inc Płynny preparat deferypronu o przyjemnym smaku
CN103951643B (zh) 2008-07-25 2015-12-09 盐野义制药株式会社 用作hiv整合酶抑制剂的化合物
KR101678563B1 (ko) 2008-12-11 2016-11-22 비이브 헬쓰케어 컴퍼니 카르바모일피리돈 ｈｉｖ 인테그라제 억제제를 위한 제조방법 및 중간체
KR101733625B1 (ko) 2008-12-11 2017-05-10 시오노기세야쿠 가부시키가이샤 카르바모일피리돈 ｈｉｖ 인테그라제 억제제 및 중간체의 합성
TWI518084B (zh) 2009-03-26 2016-01-21 鹽野義製藥股份有限公司 哌喃酮與吡啶酮衍生物之製造方法
ME01911B (me) 2009-07-03 2014-12-20 Apotex Tech Inc Fluorisani derivati 3-hidroksipiridin-4-ona
TWI582097B (zh) 2010-03-23 2017-05-11 Ｖｉｉｖ醫療保健公司 製備胺甲醯吡啶酮衍生物及中間體之方法
CN109438405B (zh) * 2018-12-24 2023-04-07 广东莱佛士制药技术有限公司 一种3-(苄氧基)-4-氧代-4h-吡喃-2-羧酸的合成方法
WO2020132820A1 (zh) * 2018-12-24 2020-07-02 广东莱佛士制药技术有限公司 一种3-(苄氧基)-4-氧代-4h-吡喃-2-羧酸的合成方法
CN111606879A (zh) * 2020-05-25 2020-09-01 安徽金禾实业股份有限公司 一锅法制备2-羟甲基-3-烷氧基-4h-吡喃-4-酮的方法
CN114736155B (zh) * 2021-03-10 2023-12-05 浙江工业大学 Ala杂合3-羟基吡啶酮衍生物及其制备方法与应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1518098A1 (de) * 1963-09-19 1969-04-10 Pfizer & Co C Verfahren zur Herstellung von Pyromekonsaeurederivaten
US3468915A (en) * 1966-04-18 1969-09-23 Pfizer & Co C Novel 2-substituted-6-methylpyromeconic acids
JPS5921954B2 (ja) * 1980-02-13 1984-05-23 新日本製鐵株式会社 鋼材の防錆処理方法
US5112968A (en) * 1989-07-28 1992-05-12 E. R. Squibb & Sons, Inc. Monobactam hydrazide derivatives
GB9006522D0 (en) * 1990-03-23 1990-05-23 Hider Robert C Metal complexes
ES2244967T3 (es) * 1995-09-29 2005-12-16 Novartis Ag Nuevas hidroxipiridinonas.

Also Published As

Publication number Publication date
WO1998054138A1 (en) 1998-12-03
DK0984934T3 (da) 2003-05-05
DE69810619T2 (de) 2003-09-25
US6335353B1 (en) 2002-01-01
US6506911B2 (en) 2003-01-14
CA2287907A1 (en) 1998-12-03
EP0984934B1 (en) 2003-01-08
EP0984934A1 (en) 2000-03-15
US20020068758A1 (en) 2002-06-06
ATE230728T1 (de) 2003-01-15
AU751600B2 (en) 2002-08-22
CA2287907C (en) 2009-01-13
ZA984635B (en) 1999-11-29
AU7542798A (en) 1998-12-30
JP2002500663A (ja) 2002-01-08
GB9711093D0 (en) 1997-07-23
DE69810619D1 (de) 2003-02-13

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