WO2005123697A1 - Dérivés de quinazoline - Google Patents

Dérivés de quinazoline Download PDF

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Publication number
WO2005123697A1
WO2005123697A1 PCT/JP2005/011174 JP2005011174W WO2005123697A1 WO 2005123697 A1 WO2005123697 A1 WO 2005123697A1 JP 2005011174 W JP2005011174 W JP 2005011174W WO 2005123697 A1 WO2005123697 A1 WO 2005123697A1
Authority
WO
WIPO (PCT)
Prior art keywords
chloro
fluorophenyl
pyrrolidine
substituted
group
Prior art date
Application number
PCT/JP2005/011174
Other languages
English (en)
Japanese (ja)
Inventor
Noriyuki Kawano
Noriko Ishikawa
Hiroyuki Kaizawa
Naoyuki Masuda
Wataru Hamaguchi
Yohei Koganemaru
Koji Kato
Takahiro Miyazaki
Original Assignee
Astellas Pharma 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 Astellas Pharma Inc. filed Critical Astellas Pharma Inc.
Publication of WO2005123697A1 publication Critical patent/WO2005123697A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • 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
    • 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
    • A61P37/08—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
    • 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
    • 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
    • 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
    • C07D405/04—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 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
    • C07D405/14—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 three or more hetero rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
    • 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
    • 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
    • C07D417/14—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 three or more hetero rings

Definitions

  • Chemokines which are cell chemotactic factors, are broadly classified into two types, CXCZ chemokines and CCZ iS chemokines, depending on their structural characteristics.
  • these chemokine receptors belong to the family of seven transmembrane G-protein coupled receptors, and are composed of CXC chemokine receptor and CC chemokine receptor (Pharmacological Reviews, 52, 145, 2000).
  • Non-Patent Document 1 a compound having an ⁇ -blocking effect
  • Patent Document 4 a compound having an antitumor activity
  • Patent Document 5 a compound having a Rho-kinase inhibitory activity
  • any of the documents compounds in which a cyclic amino group substituted at the 2-position is further substituted with a nitrogen-containing heterocyclic ring or an amino group via a carbonyl group are described. No disclosure. There is no disclosure or suggestion of CCR4 inhibitory activity.
  • Patent Document 3 JP-A-2000-281660
  • R QQ lower alkylene
  • “Lower alkylene” means a divalent group (C alkylene) obtained by removing one arbitrary hydrogen atom from the above “lower alkyl”, preferably C alkylene, and more preferably methyl alkylene.
  • any carbon atom may be substituted with an oxo group.
  • Compound (I) may form an acid addition salt or a salt with a base depending on the type of the substituent.
  • the strong salt is a pharmaceutically acceptable salt, specifically, an inorganic acid such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, and propion.
  • the effect on mouthoxazolone-induced contact dermatitis was confirmed by the following method.
  • the abdomen of Balb / c mice (6 to 10 weeks old, female, Nippon Charles' Riva Co., Ltd.) is sensitized by applying a 3% oxazolone / ethanol solution 150 1 (Sigma-Aldrich Japan).
  • Six days after sensitization apply 1% oxazolone / ethanol solution 10 1 to both sides of the right ear.
  • the test drug is administered 12 hours after application of the oxazolone solution (test drug administration group), and the control group receives only the solvent used to dissolve the test drug.
  • the pharmacological action of the compound of the present invention can be confirmed by various evaluation models generally used for evaluating an anti-inflammatory action, such as a mouse LPS-induced TNFa production model.
  • a preparation containing one or more of compound (I) or a salt thereof as an active ingredient is prepared using a carrier, an excipient, and other additives that are usually used for formulation.

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

Abstract

Composé utile pour la prévention ou le remède de maladies inflammatoires, maladies allergiques ou maladie auto-immunes dans lesquelles participe le récepteur 4 (CCR4) de la chimiokine CC, c’est-à-dire dérivé de la quinalozine ayant un groupe anilino ou cycloalkylamino à la position 4 et un groupe amino cyclique substitué par un groupe hétérocyclique contenant de l’azote ou un groupe amino via le carbonyle tel que le pipérazino en position 2. Du fait d’avoir une activité favorable en tant que contrôleur de la fonction CCR4, le composé décrit ci-dessus est utile en tant que remède ou dans la prévention de maladies inflammatoires, maladies allergiques ou maladies auto-immunes, en particulier des dermatites, etc.
PCT/JP2005/011174 2004-06-21 2005-06-17 Dérivés de quinazoline WO2005123697A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004-183086 2004-06-21
JP2004183086A JP2007269629A (ja) 2004-06-21 2004-06-21 キナゾリン誘導体

Publications (1)

Publication Number Publication Date
WO2005123697A1 true WO2005123697A1 (fr) 2005-12-29

Family

ID=35509608

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2005/011174 WO2005123697A1 (fr) 2004-06-21 2005-06-17 Dérivés de quinazoline

Country Status (2)

Country Link
JP (1) JP2007269629A (fr)
WO (1) WO2005123697A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007071952A1 (fr) * 2005-12-21 2007-06-28 Astrazeneca Ab Pipérazines pouvant être employées en tant qu'antagonistes de chimiokines c-c (ccr2b et ccr5) dans le traitement de maladies inflammatoires
WO2007111227A1 (fr) 2006-03-24 2007-10-04 Astellas Pharma Inc. Compose d'acylaminopiperidine
WO2009037454A2 (fr) 2007-09-18 2009-03-26 Cancer Research Technology Ltd Marqueur du cancer et cible thérapeutique
WO2011048032A1 (fr) * 2009-10-21 2011-04-28 F. Hoffmann-La Roche Ag Dérivés du diazépam en tant que modulateurs des récepteurs des chimiokines
JP2013514990A (ja) * 2009-12-18 2013-05-02 ヤンセン ファーマシューティカ エヌ．ベー． Ｄｐｐ−１の阻害剤として有用な置換ベンゾチアゾール誘導体及び置換ベンゾオキサゾール誘導体
WO2013140148A1 (fr) * 2012-03-19 2013-09-26 Imperial Innovations Limited Composés de quinazoline et leur utilisation thérapeutique
US20140080848A1 (en) * 2012-09-14 2014-03-20 National Taiwan University Aryl amine substituted pyrimidine and quinazoline and their use as anticaner drugs
US9394261B2 (en) 2012-09-14 2016-07-19 National Yang-Ming University Aryl amine substituted pyrimidine and quinazoline and their use as anticancer drugs
US9452990B2 (en) 2012-06-20 2016-09-27 Novartis Ag Complement pathway modulators and uses thereof
WO2018005552A1 (fr) 2016-06-27 2018-01-04 Achillion Pharmaceuticals, Inc. Composés de quinazoline et d'indole destinés au traitement de troubles médicaux
CN111808077A (zh) * 2019-04-12 2020-10-23 浙江海正药业股份有限公司 哌嗪酰胺衍生物，其制备方法及其在医药上的用途
WO2023232130A1 (fr) * 2022-06-02 2023-12-07 西藏海思科制药有限公司 Inhibiteur de ccr4 à composé hétérocyclique et son utilisation

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992014716A1 (fr) * 1991-02-20 1992-09-03 Pfizer Inc. Derives de 2,4-diaminoquinazolines stimulant l'activite anti-tumorale
JP2000281660A (ja) * 1999-03-29 2000-10-10 Sumitomo Pharmaceut Co Ltd キナゾリン誘導体
WO2002076976A2 (fr) * 2001-03-23 2002-10-03 Bayer Corporation Inhibiteurs de rho-kinase

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992014716A1 (fr) * 1991-02-20 1992-09-03 Pfizer Inc. Derives de 2,4-diaminoquinazolines stimulant l'activite anti-tumorale
JP2000281660A (ja) * 1999-03-29 2000-10-10 Sumitomo Pharmaceut Co Ltd キナゾリン誘導体
WO2002076976A2 (fr) * 2001-03-23 2002-10-03 Bayer Corporation Inhibiteurs de rho-kinase

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007071952A1 (fr) * 2005-12-21 2007-06-28 Astrazeneca Ab Pipérazines pouvant être employées en tant qu'antagonistes de chimiokines c-c (ccr2b et ccr5) dans le traitement de maladies inflammatoires
US7943768B2 (en) 2005-12-21 2011-05-17 Astrazeneca Ab Piperazine compounds useful as antagonists of C-C chemokines (Ccr2b and CcrS) for the treatment of inflammatory diseases
WO2007111227A1 (fr) 2006-03-24 2007-10-04 Astellas Pharma Inc. Compose d'acylaminopiperidine
US7790884B2 (en) 2006-03-24 2010-09-07 Astellas Pharma Inc. Acylaminopiperidine compound
JP5067364B2 (ja) * 2006-03-24 2012-11-07 アステラス製薬株式会社 アシルアミノピペリジン化合物
WO2009037454A2 (fr) 2007-09-18 2009-03-26 Cancer Research Technology Ltd Marqueur du cancer et cible thérapeutique
EP2533047A1 (fr) 2007-09-18 2012-12-12 Cancer Research Technology Ltd CCR4 en tant que cible thérapeutique pour le cancer.
EP2535716A2 (fr) 2007-09-18 2012-12-19 Cancer Research Technology Limited Marqueur de cancer et cible thérapeutique
WO2011048032A1 (fr) * 2009-10-21 2011-04-28 F. Hoffmann-La Roche Ag Dérivés du diazépam en tant que modulateurs des récepteurs des chimiokines
CN102762541A (zh) * 2009-10-21 2012-10-31 霍夫曼-拉罗奇有限公司 作为趋化因子受体的调节剂的二氮杂*衍生物
US8445674B2 (en) 2009-10-21 2013-05-21 Hoffmann-La Roche Inc Heterocyclyl compounds
JP2013514990A (ja) * 2009-12-18 2013-05-02 ヤンセン ファーマシューティカ エヌ．ベー． Ｄｐｐ−１の阻害剤として有用な置換ベンゾチアゾール誘導体及び置換ベンゾオキサゾール誘導体
WO2013140148A1 (fr) * 2012-03-19 2013-09-26 Imperial Innovations Limited Composés de quinazoline et leur utilisation thérapeutique
US9452990B2 (en) 2012-06-20 2016-09-27 Novartis Ag Complement pathway modulators and uses thereof
US20140080848A1 (en) * 2012-09-14 2014-03-20 National Taiwan University Aryl amine substituted pyrimidine and quinazoline and their use as anticaner drugs
US9394261B2 (en) 2012-09-14 2016-07-19 National Yang-Ming University Aryl amine substituted pyrimidine and quinazoline and their use as anticancer drugs
WO2018005552A1 (fr) 2016-06-27 2018-01-04 Achillion Pharmaceuticals, Inc. Composés de quinazoline et d'indole destinés au traitement de troubles médicaux
US10961252B2 (en) 2016-06-27 2021-03-30 Achillion Pharmaceuticals, Inc. Quinazoline and indole compounds to treat medical disorders
EP3939591A1 (fr) 2016-06-27 2022-01-19 Achillion Pharmaceuticals, Inc. Composés de quinazoline et d'indole pour traiter des troubles médicaux
US11248000B2 (en) 2016-06-27 2022-02-15 Achillion Pharmaceuticals, Inc. Quinazoline and indole compounds to treat medical disorders
CN111808077A (zh) * 2019-04-12 2020-10-23 浙江海正药业股份有限公司 哌嗪酰胺衍生物，其制备方法及其在医药上的用途
JP2022528437A (ja) * 2019-04-12 2022-06-10 浙江海正薬業股▲ふん▼有限公司 ピペラジンアミド誘導体、その製造方法及び医薬におけるその用途
CN111808077B (zh) * 2019-04-12 2023-05-02 浙江海正药业股份有限公司 哌嗪酰胺衍生物，其制备方法及其在医药上的用途
JP7335972B2 (ja) 2019-04-12 2023-08-30 浙江海正薬業股▲ふん▼有限公司 ピペラジンアミド誘導体、その製造方法及び医薬におけるその用途
WO2023232130A1 (fr) * 2022-06-02 2023-12-07 西藏海思科制药有限公司 Inhibiteur de ccr4 à composé hétérocyclique et son utilisation

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