CA2094137C - Novel hydroxamic acid and n-hydroxyurea derivatives and their use - Google Patents

Novel hydroxamic acid and n-hydroxyurea derivatives and their use Download PDF

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Publication number
CA2094137C
CA2094137C CA002094137A CA2094137A CA2094137C CA 2094137 C CA2094137 C CA 2094137C CA 002094137 A CA002094137 A CA 002094137A CA 2094137 A CA2094137 A CA 2094137A CA 2094137 C CA2094137 C CA 2094137C
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CA
Canada
Prior art keywords
nmr
compound according
alkyl
mmol
dmso
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 - Fee Related
Application number
CA002094137A
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English (en)
French (fr)
Other versions
CA2094137A1 (en
Inventor
Takafumi Ikeda
Akiyoshi Kawai
Takashi Mano
Yoshiyuki Okumura
Rodney William Stevens
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.)
Pfizer Ltd
Original Assignee
Pfizer Ltd
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Filing date
Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=18158900&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2094137(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Pfizer Ltd filed Critical Pfizer Ltd
Publication of CA2094137A1 publication Critical patent/CA2094137A1/en
Application granted granted Critical
Publication of CA2094137C publication Critical patent/CA2094137C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
    • C07C323/47—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/40—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of thiourea or isothiourea groups further bound to other hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA002094137A 1990-11-27 1991-11-13 Novel hydroxamic acid and n-hydroxyurea derivatives and their use Expired - Fee Related CA2094137C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2323814A JP3007138B2 (ja) 1990-11-27 1990-11-27 新規なヒドロキサム酸とｎ―ヒドロキシ尿素誘導体およびそれらの組成物
JP323814/90 1990-11-27
PCT/US1991/008246 WO1992009566A1 (en) 1990-11-27 1991-11-13 Novel hydroxamic acid and n-hydroxyurea derivatives and their use

Publications (2)

Publication Number Publication Date
CA2094137A1 CA2094137A1 (en) 1992-05-28
CA2094137C true CA2094137C (en) 2002-07-09

Family

ID=18158900

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002094137A Expired - Fee Related CA2094137C (en) 1990-11-27 1991-11-13 Novel hydroxamic acid and n-hydroxyurea derivatives and their use

Country Status (32)

Country Link
US (1) US6291520B1 (enExample)
EP (1) EP0559743B1 (enExample)
JP (1) JP3007138B2 (enExample)
KR (1) KR100192722B1 (enExample)
CN (1) CN1029230C (enExample)
AT (1) ATE119520T1 (enExample)
AU (1) AU653763B2 (enExample)
BR (1) BR9107124A (enExample)
CA (1) CA2094137C (enExample)
CZ (1) CZ281345B6 (enExample)
DE (2) DE9190171U1 (enExample)
DK (1) DK0559743T3 (enExample)
EG (1) EG20001A (enExample)
ES (1) ES2069410T3 (enExample)
FI (1) FI932390A0 (enExample)
GR (1) GR3015879T3 (enExample)
HU (1) HU221975B1 (enExample)
IE (1) IE64963B1 (enExample)
IL (1) IL100100A (enExample)
MX (1) MX9102209A (enExample)
MY (1) MY107341A (enExample)
NO (1) NO179582C (enExample)
NZ (1) NZ240737A (enExample)
PL (1) PL167584B1 (enExample)
PT (1) PT99597B (enExample)
RU (1) RU2104267C1 (enExample)
SK (1) SK282645B6 (enExample)
TW (1) TW262461B (enExample)
UA (1) UA39166C2 (enExample)
WO (1) WO1992009566A1 (enExample)
YU (1) YU48416B (enExample)
ZA (1) ZA919317B (enExample)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2078126A1 (en) * 1990-03-27 1991-09-28 Jerry Leroy Adams 5-lipoxygenase inhibitors
US5639782A (en) * 1992-03-04 1997-06-17 Center For Innovative Technology Neolignan derivatives as platelet activating factor receptor antagonists and 5-lipoxygenase inhibitors
JPH05294921A (ja) * 1992-04-17 1993-11-09 Pfizer Pharmaceut Co Ltd 新規なフェニル置換シクロアルキル尿素誘導体および組成物
US5326787A (en) * 1992-05-12 1994-07-05 Abbott Laboratories Cycloalkyl N-hydroxy derivatives having lipoxygenase inhibitory activity
JPH08502243A (ja) 1992-07-13 1996-03-12 サイトメッド，インコーポレイテッド 炎症性および免疫性疾患の治療のための２，５‐ジアリールテトラヒドロ‐チオフェン、‐フランおよび類似体
US5434151A (en) * 1992-08-24 1995-07-18 Cytomed, Inc. Compounds and methods for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
US5463083A (en) 1992-07-13 1995-10-31 Cytomed, Inc. Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5648486A (en) * 1992-07-13 1997-07-15 Cytomed, Inc. Compounds and methods for the treatment of inflammatory and immune disorders
US5358938A (en) * 1992-07-13 1994-10-25 Cytomed, Inc. Compounds and methods for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
US5506242A (en) * 1993-01-06 1996-04-09 Ciba-Geigy Corporation Arylsufonamido-substituted hydroxamic acids
US5552419A (en) * 1993-01-06 1996-09-03 Ciba-Geigy Corporation Arylsulfonamido-substituted hydroxamic acids
US5455258A (en) * 1993-01-06 1995-10-03 Ciba-Geigy Corporation Arylsulfonamido-substituted hydroxamic acids
US5646167A (en) * 1993-01-06 1997-07-08 Ciba-Geigy Corporation Arylsulfonamido-substituted hydroxamix acids
WO1994018158A1 (en) * 1993-02-15 1994-08-18 Pfizer Inc. Spiroalkylhydroxyureas for use as lipoxygenase inhibitors
DE69411003T2 (de) * 1993-04-07 1998-10-08 Pfizer Inc., New York, N.Y. Cycloalkylhydroxyharnstoffe und ihre verwendung als lipoxy-genase-inhibitoren
CA2167715C (en) * 1993-07-20 1998-10-06 Akiyoshi Kawai Heteroaryl cycloalkenyl hydroxyureas
TW448144B (en) * 1993-08-19 2001-08-01 Pfizer Phenoxyphenyl cyclopentenyl hydroxyureas
CA2178833A1 (en) * 1993-12-22 1995-06-29 Akiyoshi Kawai Phenylthiophenyl cycloalkenyl hydroxyureas as lipoxygenase inhibitors
US5703093A (en) * 1995-05-31 1997-12-30 Cytomed, Inc. Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5750565A (en) 1995-05-25 1998-05-12 Cytomed, Inc. Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5792776A (en) * 1994-06-27 1998-08-11 Cytomed, Inc., Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
CN1059669C (zh) * 1994-11-10 2000-12-20 辉瑞大药厂 芳氧基环烯基－和芳氧基亚氨基环烯基羟基脲类化合物
CA2205033C (en) * 1994-11-10 2001-12-11 Akiyoshi Kawai Aryloxycycloalkenyl and aryloxyiminocycloalkenylhydroxyureas as 5-lipoxygenase inhibitors
WO1996016054A1 (en) * 1994-11-18 1996-05-30 Pfizer Pharmaceuticals Inc. Cycloalkenyl-n-hydroxyureas
WO1996023772A1 (en) * 1995-02-02 1996-08-08 Nikken Chemicals Co., Ltd. N-hydroxyurea derivatives
CA2176854A1 (en) * 1995-06-07 1996-12-08 Daniel J. Keavy N-acyl-2 aryl cyclopropylmethylamine derivatives as melatonergics
US6828460B2 (en) 1999-03-22 2004-12-07 Pfizer Inc. Resorcinol derivatives
EP1418173A1 (en) * 1999-03-26 2004-05-12 Ucb, S.A. N-(3-butyn-1-yl) N-hydroxyurea
US6521619B2 (en) 2000-06-29 2003-02-18 Icos Corporation Aryl phenylcyclopropyl sulfide derivatives and their use as cell adhesion inhibiting anti-inflammatory and immune suppressive agents
US20040029893A1 (en) * 2002-07-23 2004-02-12 Lane Edward M. Method of treatment of non-invasive mucositis
US20070078116A1 (en) * 2003-08-20 2007-04-05 Fairfield Clinical Trials, Llc Method of treatment of otitis externa
US20050043251A1 (en) * 2003-08-20 2005-02-24 Fairfield Clinical Trials, Llc Method of treatment of otitis externa
US20050159369A1 (en) * 2003-08-20 2005-07-21 Qtm Llc Method of treatment of otitis externa
KR100786479B1 (ko) 2006-09-22 2007-12-17 삼성에스디아이 주식회사 평판표시장치 및 이를 이용한 휴대용 표시기기
MX2009012685A (es) 2007-05-31 2009-12-14 Sepracor Inc Cicloalquilaminas sustituidas con fenilo como inhibidores de la reabsorcion de monoamina.
US8357635B2 (en) 2009-10-16 2013-01-22 Syngenta Crop Protection Llc Microbiocides

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2559699B2 (ja) 1985-03-16 1996-12-04 ザ ウエルカム フアウンデ−シヨン リミテツド 新規なアリ−ル誘導体
ES2053609T3 (es) 1987-04-24 1994-08-01 Abbott Lab Derivados de urea inhibidores de lipoxigenasa.
GB8830427D0 (en) * 1988-12-30 1989-03-01 Fujisawa Pharmaceutical Co New hydroxylamine derivatives,a process for the preparation thereof and pharmaceutical composition comprising the same
US5120752A (en) * 1989-12-28 1992-06-09 Abbott Laboratories Cyclopropyl derivative lipoxygenase inhibitors
GB9025514D0 (en) 1990-11-23 1991-01-09 Wellcome Found Anti-inflammatory compounds
DE4124345A1 (de) * 1991-07-23 1993-01-28 Gruenenthal Gmbh Substituierte 3,4-dihydronaphthaline, diese verbindungen enthaltende arzneimittel und verfahren zur herstellung dieser verbindungen und arzneimittel
US5187192A (en) 1992-03-13 1993-02-16 Abbott Laboratories Cyclobutyl derivatives having lipoxygenase inhibitory activity

Also Published As

Publication number Publication date
CZ99093A3 (en) 1994-07-13
DE9190171U1 (de) 1993-08-12
IL100100A (en) 1998-03-10
DE69108048D1 (de) 1995-04-13
ATE119520T1 (de) 1995-03-15
HU9301550D0 (en) 1993-09-28
YU48416B (sh) 1998-07-10
MX9102209A (es) 1992-06-01
GR3015879T3 (en) 1995-07-31
SK282645B6 (sk) 2002-10-08
AU653763B2 (en) 1994-10-13
FI932390L (fi) 1993-05-26
FI932390A7 (fi) 1993-05-26
PL167584B1 (pl) 1995-09-30
TW262461B (enExample) 1995-11-11
YU186291A (sh) 1994-01-20
FI932390A0 (fi) 1993-05-26
CA2094137A1 (en) 1992-05-28
ZA919317B (en) 1993-05-26
EP0559743B1 (en) 1995-03-08
US6291520B1 (en) 2001-09-18
PT99597A (pt) 1992-10-30
NO179582B (no) 1996-07-29
CZ281345B6 (cs) 1996-08-14
MY107341A (en) 1995-11-30
IE914101A1 (en) 1992-06-03
IL100100A0 (en) 1992-08-18
SK54793A3 (en) 1993-10-06
JPH04193857A (ja) 1992-07-13
NO931921D0 (no) 1993-05-26
JP3007138B2 (ja) 2000-02-07
ES2069410T3 (es) 1995-05-01
EP0559743A1 (en) 1993-09-15
HUT67436A (en) 1995-04-28
WO1992009566A1 (en) 1992-06-11
PT99597B (pt) 2000-08-31
CN1029230C (zh) 1995-07-05
NO931921L (no) 1993-05-26
NO179582C (no) 1996-11-06
UA39166C2 (uk) 2001-06-15
HU221975B1 (hu) 2003-03-28
CN1061775A (zh) 1992-06-10
AU9053591A (en) 1992-06-25
EG20001A (en) 1997-03-27
DK0559743T3 (da) 1995-07-03
NZ240737A (en) 1994-07-26
RU2104267C1 (ru) 1998-02-10
KR100192722B1 (ko) 1999-06-15
BR9107124A (pt) 1993-11-09
IE64963B1 (en) 1995-09-20
DE69108048T2 (de) 1995-07-06

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