WO2013056684A3 - Thiazole derivative as dhodh inhibitor and use thereof - Google Patents

Thiazole derivative as dhodh inhibitor and use thereof Download PDF

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Publication number
WO2013056684A3
WO2013056684A3 PCT/CN2012/086816 CN2012086816W WO2013056684A3 WO 2013056684 A3 WO2013056684 A3 WO 2013056684A3 CN 2012086816 W CN2012086816 W CN 2012086816W WO 2013056684 A3 WO2013056684 A3 WO 2013056684A3
Authority
WO
WIPO (PCT)
Prior art keywords
thiazole derivative
dhodh inhibitor
dhodh
inhibitor
psoriasis
Prior art date
Application number
PCT/CN2012/086816
Other languages
French (fr)
Chinese (zh)
Other versions
WO2013056684A2 (en
Inventor
赵振江
黄瑾
李洪林
徐玉芳
朱丽丽
韩乐
许鸣豪
高瑞
刁妍妍
朱俊生
曹贤文
崔坤强
Original Assignee
华东理工大学
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 华东理工大学 filed Critical 华东理工大学
Priority to CN201280048338.3A priority Critical patent/CN103998434B/en
Publication of WO2013056684A2 publication Critical patent/WO2013056684A2/en
Publication of WO2013056684A3 publication Critical patent/WO2013056684A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • A61P37/02—Immunomodulators
    • 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
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • 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
    • 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
    • C07D417/12—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 chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Rheumatology (AREA)
  • Transplantation (AREA)
  • Pain & Pain Management (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A thiazole derivative, as represented in formula I, as a DHODH inhibitor and a use thereof. The compound of the present invention can be used for treating or preventing DHODH-mediated diseases, including, but not limited to, rheumatoid arthritis and autoimmune diseases such as anti-tumor, anti-organ transplant rejection, and anti-psoriasis.
PCT/CN2012/086816 2011-10-18 2012-12-18 Thiazole derivative as dhodh inhibitor and use thereof WO2013056684A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201280048338.3A CN103998434B (en) 2011-10-18 2012-12-18 Thiazole and application thereof as DHODH inhibitor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201110317124.9 2011-10-18
CN2011103171249A CN103058949A (en) 2011-10-18 2011-10-18 Thiazole derivative acting as DHODH inhibitor and its application

Publications (2)

Publication Number Publication Date
WO2013056684A2 WO2013056684A2 (en) 2013-04-25
WO2013056684A3 true WO2013056684A3 (en) 2013-06-13

Family

ID=48101881

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2012/086816 WO2013056684A2 (en) 2011-10-18 2012-12-18 Thiazole derivative as dhodh inhibitor and use thereof

Country Status (2)

Country Link
CN (2) CN103058949A (en)
WO (1) WO2013056684A2 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104418821A (en) * 2013-08-22 2015-03-18 四川大学华西医院 2, 4-substituted 5- (3,4, 5-trimethoxyphenyl) thiazole derivative and preparation method and application thereof
CN103772315B (en) * 2014-01-07 2015-10-21 山东汇海医药化工有限公司 A kind of method of one-step synthesis 4-methylthiazole-5-carboxylate
CN105777739B (en) * 2016-02-23 2018-05-08 湖南大学 Naphthylamino thiazole methyl qualone derivative and its medical usage
CN107382902B (en) 2016-05-17 2022-08-12 华东理工大学 Thiazole derivative and application thereof
CN107375279B (en) * 2016-05-17 2022-11-01 华东理工大学 Use of novel thiazole derivatives for the treatment of inflammatory bowel disease
WO2018089902A1 (en) * 2016-11-13 2018-05-17 Apogee Biotechnology Corporation Diaminothiazole compounds, compositions and methods of use
CN108721283A (en) * 2017-04-20 2018-11-02 华东理工大学 Application of the thiazole in treating non-lymphocytic leukemia
CN110180488B (en) * 2019-05-07 2020-05-01 东北大学 High-adsorption-activity BiOI and preparation method and application thereof
WO2021214019A1 (en) 2020-04-24 2021-10-28 Bayer Aktiengesellschaft Substituted aminothiazoles as dgkzeta inhibitors for immune activation
CN115701427A (en) * 2021-08-02 2023-02-10 上海汇伦医药股份有限公司 Polysubstituted thiazole derivatives and their use in the treatment of diseases
CN115448863B (en) * 2022-10-09 2024-03-26 浙江迪邦化工有限公司 Continuous preparation process of 3, 4-dichlorophenyl thiourea

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004009017A2 (en) * 2002-07-18 2004-01-29 Bristol-Myers Squibb Company Modulators of the glucocorticoid receptor and method
CN1546034A (en) * 2003-12-08 2004-11-17 南昌弘益科技有限公司 Dripping pills of meloxicam and its preparation
CN1617870A (en) * 2001-09-28 2005-05-18 西克拉塞尔有限公司 N-(4-(4-methylthiazol-5-yl) pyrimidin-2-yl) -n-phenylamines as antiproliferative compounds
CN101248054A (en) * 2005-05-24 2008-08-20 雪兰诺实验室有限公司 Thiazole derivatives and use thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3547917A (en) * 1966-12-07 1970-12-15 Uniroyal Inc 2-amino-4-methylthiazole-5-carboxamides
EP1983980A4 (en) * 2006-01-25 2010-05-05 Synta Pharmaceuticals Corp Thiazole and thiadiazole compounds for inflammation and immune-related uses
ES2557465T3 (en) * 2010-03-17 2016-01-26 Taivex Therapeutics Inc. Modulators of HEC 1 activity and procedures for it
WO2011115758A1 (en) * 2010-03-18 2011-09-22 Takeda San Diego, Inc. Process for the production of 2-amino-5-fluorothiazole

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1617870A (en) * 2001-09-28 2005-05-18 西克拉塞尔有限公司 N-(4-(4-methylthiazol-5-yl) pyrimidin-2-yl) -n-phenylamines as antiproliferative compounds
WO2004009017A2 (en) * 2002-07-18 2004-01-29 Bristol-Myers Squibb Company Modulators of the glucocorticoid receptor and method
CN1546034A (en) * 2003-12-08 2004-11-17 南昌弘益科技有限公司 Dripping pills of meloxicam and its preparation
CN101248054A (en) * 2005-05-24 2008-08-20 雪兰诺实验室有限公司 Thiazole derivatives and use thereof

Also Published As

Publication number Publication date
CN103058949A (en) 2013-04-24
CN103998434B (en) 2016-10-12
WO2013056684A2 (en) 2013-04-25
CN103998434A (en) 2014-08-20

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