JP2000504713A - キナゾリン化合物 - Google Patents
キナゾリン化合物Info
- Publication number
- JP2000504713A JP2000504713A JP9529073A JP52907397A JP2000504713A JP 2000504713 A JP2000504713 A JP 2000504713A JP 9529073 A JP9529073 A JP 9529073A JP 52907397 A JP52907397 A JP 52907397A JP 2000504713 A JP2000504713 A JP 2000504713A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- amino
- alkoxy
- alkylamino
- 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.)
- Granted
Links
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- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- 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
- C07D213/63—One oxygen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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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
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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
- C07D401/12—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
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- 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
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- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
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- 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
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- 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
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- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- C07D409/12—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 chain containing hetero atoms as chain links
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- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
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- 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
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- 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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- 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
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- Chemical & Material Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 式I 〔式中、X1は、直接結合であるか又は式:CO、C(R2)2、CH(OR2)2 、C(R2)2−C(R2)2、C(R2)=C(R2)、C≡C、CH(CN)、 O、S、SO、SO2、N(R2)、CON(R2)、SO2N(R2)、N(R2) CO、N(R2)SO2、OC(R2)、SC(R2)2、N(R2)C(R2)2、C (R2)2O、C(R2)2S又はC(R2)2N(R2)で示される基であり、それ ぞれのR2は、独立に水素又はC1〜C4−アルキルであり; Q1は、フェニル、ナフチルであるか又は、酸素、窒素及び硫黄から選択され たヘテロ原子3個までを有する5員もしくは6員のへテロアリール成分であり、 この場合、複素環成分は、単環であるか又はベンゼン環と融合しており、かつQ1 は、ハロゲノ、ヒドロキシ、アミノ、トリフルオロメトキシ、トリフルオロメ チル、シアノ、ニトロ、カルボキシ、カルバモイル、C1〜C4−アルコキシカル バモイル、 C1〜C4−アルキル、C1〜C4−アルコキシ、C2〜C4−アルケニルオキシ、C2 〜C4−アルキニルオキシ、C1〜C3−アルキレンジオキシ、C1〜C4−アルキ ルアミノ、ジ−[C1〜C4−アルキル]アミノ、ピロリジン−1−イル、ピペリ ジノ、モルホリノ、ピペラジン−1−イル、4−C1〜C4−アルキルピペラジン −1−イル、C2〜C4−アルカノイルアミノ、N−C1〜C4−アルキルカルバモ イル、N,N−ジ−[C1〜C4−アルキル]カルバモイル、アミノ−C1〜C4− アルキル、C1〜C4−アルキルアミノ−C1〜C4−アルキル、ジ−[C1〜C4− アルキル]アミノ−C1〜C4−アルキル、ピロリジン−1−イル−C1〜C4−ア ルキル、ピペリジノ−C1〜C4−アルキル、モルホリノ−C1〜C4−アルキル、 ピペラジン−1−イル−C1〜C4−アルキル、4−C1〜C4−アルキルピペラジ ン−1−イル−C1〜C4−アルキル、ハロゲノ−C2〜C4−アルコキシ、ヒドロ キシ−C2〜C4−アルコキシ、C1〜C4−アルコキシ−C2〜C4−アルコキシ、 アミノ−C2〜C4−アルコキシ、C1〜C4−アルキルアミノ−C2〜C4−アルコ キシ、ジ−[C1〜C4−アルキル]アミノ−C2〜C4−アルコキシ、ピロリジン −1−イル−C2〜C4−アルコキシ、モルホリノ−C2〜C4−アルコキシ、ピペ ラジン−1−イル−C2〜C4−アルコキシ、4−C1〜C4−アルキルピペ ラジン−1−イル−C2〜C4−アルコキシ、C1〜C4−アルキルチオ−C2〜C4 −アルコキシ、C1〜C4−アルキルスルフィニル−C2〜C4−アルコキシ、C1 〜C4−アルキルスルホニル−C2〜C4−アルコキシ、ハロゲノ−C2〜C4−ア ルキルアミノ、ヒドロキシ−C2〜C4−アルキルアミノ、C1〜C4−アルコキシ −C2〜C4−アルキルアミノ、アミノ−C2〜C4−アルキルアミノ、C1〜C4− アルキルアミノ−C2〜C4−アルキルアミノ、ジ−[C1〜C4−アルキル]アミ ノ−C2〜C4−アルキルアミノ、ピロリジン−1−イル−C2〜C4−アルキルア ミノ、ピペリジノ−C2〜C4−アルキルアミノ、モルホリノ−C2〜C4−アルキ ルアミノ、ピペラジン−1−イル−C2〜C4−アルキルアミノ、4−C1〜C4− アルキルピペラジン−1−イル−C2〜C4−アルキルアミノ、N−C1〜C4−ア ルキル−ハロゲノ−C2〜C4−アルキルアミノ、N−C1〜C4−アルキル−ヒド ロキシ−C2〜C4−アルキルアミノ、N−C1〜C4−アルキル−C1〜C4−アル コキシ−C2〜C4−アルキルアミノ、ハロゲノ−C2〜C4−アルカノイルアミノ 、ヒドロキシ−C2〜C4−アルカノイルアミノ、C1〜C4−アルコキシ−C2〜 C4−アルカノイルアミノ、C3〜C4−アルケノイルアミノ、C3〜C4−アルキ ノイルアミノ、アミノ−C2〜C4−アルカノイルアミノ、C1〜C4−アル キルアミノ−C2〜C4−アルカノイルアミノ、ジ−[C1〜C4−アルキル]アミ ノ−C2〜C4−アルカノイルアミノ、ピロリジン−1−イル−C2〜C4−アルカ ノイルアミノ、ピペリジノ−C2〜C4−アルカノイルアミノ、モルホリノ−C2 〜C4−アルカノイルアミノ、ピペラジン−1−イル−C2〜C4−アルカノイル アミノ及び4−C1〜C4−アルキルピペラジン−1−イルC2〜C4−アルカノイ ルアミノから選択された置換基を3個まで有していてもよく、この場合、上記の 置換基のいずれかは、ハロゲノ、SO又はSO2基あるいはN、O又はS原子に 結合していないCH2(メチレン)基からなり、前記CH2基上に、ヒドロキシ、 アミノ、C1〜C4−アルコキシ、C1〜C4−アルキルアミノ及びジ−[C1〜C4 −アルキル]アミノから選択された置換基を有していてもよく; mは、1又は2であり、それぞれのR1は、独立に水素、ハロゲノ、トリフルオ ロメチル、ヒドロキシ、アミノ、ニトロ、シアノ、カルボキシ、カルバモイル、 C1〜C4−アルコキシカルバモイル、C1〜C4−アルキル、C1〜C4−アルコキ シ、C1〜C4−アルキルアミノ、ジ−[C1〜C4−アルキル]アミノ、C2〜C4 −アルカノイルアミノ、N−C1〜C4−アルキルカルバモイル又はN,N−ジ− [C1〜C4−アルキル]カルバモイルであり; Q2は、フェニルであるか又は窒素ヘテロ原子1個又は2個を有するか又は、酸 素、窒素及び硫黄から選択されたヘテロ原子をもう1個有していてもよい9員も しくは10員の二環式複素環成分であり、かつQ2は、ハロゲノ、トリフルオロ メチル、シアノ、ヒドロキシ、アミノ、ニトロ、カルボキシ、カルバモイル、C1 〜C4−アルコキシカルボニル、C1〜C4−アルキル、C1〜C4−アルコキシ、 C1〜C4−アルキルアミノ、ジ−[C1〜C4−アルキル]アミノ、C2〜C4−ア ルカノイルアミノ、N−C1〜C4−アルキルカルバモイル及びN,N−ジ−[C1 〜C4−アルキルカルバモイルから選択された置換基を3個まで有していてもよ いか又はQ2は、式II: (式中、X2は、式:CO、C(R3)2、CH(OR3)、C(R3)2−C(R3 )2、C(R3)=C(R3)、C≡C、CH(CN)、O、S、SO、SO2、N (R3)、CON(R3)、SO2N(R3)、N(R3)CO、N(R3)SO2、 OC(R3)2、SC(R3)2、C(R3)2O又はC(R3)2Sで 示される基であり、この場合、それぞれのR3は、独立に水素又はC1〜C4−ア ルキルであり、 Q3は、フェニル又はナフチルであるかあるいは、酸素、窒素及び硫黄から選択 されたヘテロ原子3個までを有する5員もしくは6員のヘテロアリール成分であ り、この場合、ヘテロアリール成分は、単環であるか又はベンゼン環と融合して おり、かつ前記フェニル又はナフチル基又はヘロアリール成分は、ハロゲノ、ト リフルオロメチル、シアノ、ヒドロキシ、アミノ、ニトロ、カルボキシ、カルバ モイル、C1〜C4−アルコキシカルボニル、C1〜C4−アルキル、C1〜C4−ア ルコキシ、C1〜C4−アルキルアミノ、ジ−[C1〜C4−アルキル]アミノ、C2 〜C4−アルカノイルアミノ、N−C1〜C4−アルキルカルバモイル及びN,N −ジ−[C1〜C4−アルキル]カルバモイルから選択された置換基を3個まで有 していてもよく、 nは、1、2又は3であり、それぞれのR4は、独立に水素、ハロゲノ、トリフ ルオロメチル、シアノ、ヒドロキシ、アミノ、ニトロ、C1〜C4−アルキル、C1 〜C4−アルコキシ、C1〜C4−アルキルアミノ、ジ−[C1〜C4−アルキル] アミノ又はC2〜C4−アルカノイルアミノである)で示される基である〕で示さ れるキナゾリン誘導体又はその製薬学的に認容性の塩であり、 Q1が、置換されていてもよいフェニルである場合には、X1は、N(R2)C O、N(R2)SO2、OC(R2)2、N(R2)C(R2)2、C(R2)2S又は C(R2)2N(R2)ではなく;X1が、直接結合である場合には、Q1は、窒素 ヘテロ原子を3個まで有する5員もしくは9員の窒素結合したヘテロアリール成 分ではないものとする。 2. X1が、直接結合であるか又は式:CO、C(R2)2、CH(OR2)、C( R2)2−C(R2)2、C(R2)=C(R2)、C≡C、CH(CN)、O、S、 SO、SO2、N(R2)、CON(R2)、SO2N(R2)、N(R2)CO、N (R2)SO2、OC(R2)2、SC(R2)2、N(R2)C(R2)2、C(R2)2 O、C(R2)2S又はC(R2)2N(R2)で示される基であり、それぞれのR2 は、独立に水素又はC1〜C4−アルキルであり; Q1は、酸素、窒素及び硫黄から選択されたヘテロ原子を3個まで有する5員 もしくは6員のヘテロアリール成分であり、この場合、複素環成分は、単環であ るか又はベンゼン環と融合しており、かつQ1は、ハロゲノ、ヒドロキシ、アミ ノ、トリフルオロメトキシ、トリフルオロメチル、シアノ、ニトロ、カルボキシ 、カルバモイル、C1〜C4−アルコキシカルボニル、C1〜C4−アルキル、C1 〜C4−アルコキシ、C2〜C4−アルケニルオキシ、C2〜C4− アルキニルオキシ、C1〜C3−アルキレンジオキシ、C1〜C4−アルキルアミノ 、ジ−[C1〜C4−アルキル]アミノ、ピロリジン−1−イル、ピペリジノ、モ ルホリノ、ピペラジン−1−イル、4−C1〜C4−アルキルピペラジン−1−イ ル、C2〜C4−アルカノイルアミノ、N−C1〜C4−アルキルカルバモイル、N ,N−ジ−[C1〜C4−アルキル]カルバモイル、アミノ−C1〜C4−アルキル 、C1〜C4−アルキルアミノ−C1〜C4−アルキル、ジ−[C1〜C4−アルキル ]アミノ−C1〜C4−アルキル、ピロリジン−1−イル−C1〜C4−アルキル、 ピペリジノ−C1〜C4−アルキル、モルホリノ−C1〜C4−アルキル、ピペラジ ン−1−イル−C1〜C4−アルキル、4−C1〜C4−アルキルピペラジン−1− イル−C1〜C4−アルキル、ハロゲノ−C2〜C4−アルコキシ、ヒドロキシ−C2 〜C4−アルコキシ、C1〜C4−アルコキシ−C2〜C4−アルコキシ、アミノ− C2〜C4−アルコキシ、C1〜C4−アルキルアミノ−C2〜C4−アルコキシ、ジ −[C1〜C4−アルキル]アミノ−C2〜C4−アルコキシ、ピロリジン−1−イ ル−C2〜C4−アルコキシ、ピペリジノ−C2〜C4−アルコキシ、モルホリノ− C2〜C4−アルコキシ、ピペラジン−1−イル−C2〜C4−アルコキシ、4−C1 〜C4−アルキルピペラジン−1−イル−C2〜C4−アルコキシ、C1 〜C4−アルキルチオ−C2〜C4−アルコキシ、C1〜C4−アルキルスルフィニ ル−C2〜C4−アルコキシ、C1〜C4−アルキルスルホニル−C2〜C4−アルコ キシ、ハロゲノ−C2〜C4−アルキルアミノ、ヒドロキシ−C2〜C4−アルキル アミノ、C1〜C4−アルコキシ−C2〜C4−アルキルアミノ、アミノ−C2〜C4 −アルキルアミノ、C1〜C4−アルキルアミノ−C2〜C4−アルキルアミノ、ジ −[C1〜C4−アルキル]アミノ−C2〜C4−アルキルアミノ、ピロリジン−1 −イル−C2〜C4−アルキルアミノ、ピペリジノ−C2〜C4−アルキルアミノ、 モルホリノ−C2〜C4−アルキルアミノ、ピペラジン−1−イル−C2〜C4−ア ルキルアミノ、4−C1〜C4−アルキルピペラジン−1−イル−C2〜C4−アル キルアミノ、N−C1〜C4−アルキル−ハロゲノ−C2〜C4−アルキルアミノ、 N−C1〜C4−アルキル−ヒドロキシ−C2〜C4−アルキルアミノ、N−C1〜 C4−アルキル−C1〜C4−アルコキシ−C2〜C4−アルキルアミノ、ハロゲノ −C2〜C4−アルカノイルアミノ、ヒドロキシ−C2〜C4−アルカノイルアミノ 、C1〜C4−アルコキシ−C2〜C4−アルカノイルアミノ、C3〜C4−アルケノ イルアミノ、C3〜C4−アルキノイルアミノ、アミノ−C2〜C4−アルカノイル アミノ、C1〜C4−アルキルアミノ−C2〜C4−アルカノイルアミノ、ジ− [C1〜C4−アルキル]アミノ−C2〜C4−アルカノイルアミノ、ピロリジン− 1−イル−C2〜C4−アルカノイルアミノ、ピペリジノ−C2〜C4−アルカノイ ルアミノ、モルホリノ−C2〜C4−アルカノイルアミノ、ピペラジン−1−イル −C2〜C4−アルカノイルアミノ及び4−C1〜C4−アルキルピペラジン−1− イル−C2〜C4−アルカノイルアミノから選択された置換基を3個まで有してい てもよく、この場合、上記の置換基のいずれかは、ハロゲノ、SO又はSO2基 あるいはN、O又はS原子に結合していないCH2(メチレン)基からなり、前 記CH2基上に、ヒドロキシ、アミノ、C1〜C4−アルコキシ、C1〜C4−アル キルアミノ及びジ−[C1〜C4−アルキル]アミノから選択された置換基を有し ていてもよく: mは、1又は2であり、それぞれのR1は、独立に水素、ハロゲノ、トリフルオ ロメチル、ヒドロキシ、アミノ、ニトロ、シアノ、カルボキシ、カルバモイル、 C1〜C4−アルコキシカルバモイル、C1〜C4−アルキル、C1〜C4−アルコキ シ、C1〜C4−アルキルアミノ、ジ−[C1〜C4−アルキル]アミノ、C2〜C4 −アルカノイルアミノ、N−C1〜C4−アルキルカルバモイル又はN,N−ジ− [C1〜C4−アルキル]カルバモイルであり; Q2は、ハロゲノ、トリフルオロメチル、シアノ、 ヒドロキシ、アミノ、ニトロ、カルボキシ、カルバモイル、C1〜C4−アルコキ シカルボニル、C1〜C4−アルキル、C1〜C4−アルコキシ、C1〜C4−アルキ ルアミノ、ジ−[C1〜C4−アルキル]アミノ、C2〜C4−アルカノイルアミノ 、N−C1〜C4−アルキルカルバモイル及びN,N−ジ−[C1〜C4−アルキル カルバモイルから選択された置換基を3個まで有していてもよいフェニルである 、請求項1に記載の式Iのキナゾリン誘導体又はその製薬学的に認容性の塩であ り、 X1が、直接結合である場合には、Q1は窒素ヘテロ原子を3個まで有している 5員もしくは9員の窒素結合したヘテロアリール成分ではないものとする。 3. X1が、直接結合であるか又は式:CH2、CH2CH2、NH、NHCO、N HSO2、OCH2、SCH2、NHCH2、CH2O又はCH2Sで示される基であ り; Q1は、メチル、アミノメチル、2−アミノエチル、メチルアミノメチル、2 −メチルアミノエチル、ジメチルアミノメチル、2−ジメチルアミノエチル、ピ ロリジン−1−イルメチル、2−ピロリジン−1−イルエチル、ピペリジノメチ ル、2−ピペリジノメチル、モルホリノメチル、2−モルホリノエチル、ピペラ ジン−1−イルメチル、2−ピペラジン−1−イルエチル、4−メチルピペラジ ン−1−イ ルメチル及び2−(4−メチルピペラジン−1−イル)エチルから選択された置 換基を有していてもよい2−フリル、3−フリル、2−チエニル、3−チエニル 、2−ピリジル、3−ピリジル、4−ピリジル、2−オキサゾリル、4−オキサ ゾリル、5−イソキサゾリル、3−ピラゾリル、2−イミダゾリル、4−イミダ ゾリル、2−チアゾリル、4−チアゾリル、5−イソチアゾリル又は1,2,3 −トリアゾル−4−イルであり、 mは、1であり、R1は、水素又はメトキシであり; Q2は、フルオロ、クロロ、ブロモ、トリフルオロメチル、シアノメチル及びメ トキシから選択された置換基を1個、2個又は3個有していてもよいフェニルで あるか又はQ2は、式II: 〔式中、X2は、式CO又はOCH2で示される基であり、Q3は、フルオロ、ク ロロ、ブロモ、メチル及びメトキシから選択された置換基1個又は2個を有して いてもよいフェニル又は2−ピリジルであり、nは、1であり、R4は、水素、 フルオロ、クロ ロ、ブロモ又はメチルである〕 で示される基である、請求項1に記載の式Iのキナゾリン誘導体又はその製薬学 的に認容性の酸付加塩。 4. X1が、直接結合であるか又は式:NHCO、OCH2又はNHCH2で示さ れる基であり; Q1は、アミノメチル、モルホリノメチル及び2−モルホリノメチルから選択 された置換基を有していてもよいフリル、3−フリル、2−チエニル、3−チエ ニル、2−ピリジル、3−ピリジル、4−オキサゾリル、5−イソキサゾリル又 は4−イミダゾリルであり; mは、1であり、R1は、水素又はメトキシであり; Q2は、フルオロ、クロロ、ブロモ及びメチルから選択された置換基を1個又 は2個有していてもよいフェニルである、請求項1に記載の式Iのキナゾリン誘 導体又はその製薬学的に認容性の酸付加塩。 5. 4−(3−クロロ−4−フルオロアニリノ)−6−(3−フリル)キナゾリ ン、4−(3−クロロ−4−フルオロアニリノ)6−(2−チエニル)キナゾリ ン、4−(3−クロロ−4−フルオロアニリノ)−6−[5−(2−モルホリノ エチル)チエン−2−イル]キナゾリン、4−(3−クロロ−4−フルオロアニ リノ−6−(5−モルホリノメチルチエ ン−3−イル)キナゾリン及び4−(3−クロロ−4−フルオロアニリノ)−7 −メトキシ−6−(3−ピリジルメトキシ)キナゾリンから選択された、請求項 1に記載の式Iのキナゾリン誘導体又はその製薬学的に認容性の酸付加塩。 6. X1が、直接結合であり; Q1は、アミノ−C1〜C4−アルキル、C1〜C4−アルキルアミノ−C1〜C4 −アルキル、ジ−[C1〜C4−アルキル]アミノ−C1〜C4−アルキル、ピロリ ジン−1−イル−C1〜C4−アルキル、ピペリジノ−C1〜C4−アルキル、モル ホリノ−C1〜C4−アルキル、ピペラジン−1−イル−C1〜C4−アルキル及び 4−C1〜C4−アルキルピペラジン−1−イル−C1〜C4−アルキルから選択さ れた置換基を有しているチエニルであり、 mは、1であり、R1は、水素であり; Q2は、ハロゲノ、トリフルオロメチル、シアノ、ヒドロキシ、アミノ、ニト ロ、カルボキシ、カルバモイル、C1〜C4−アルコキシカルボニル、C1〜C4− アルキル、C1〜C4−アルコキシ、C1〜C4−アルキルアミノ、ジ−[C1〜C4 −アルキル]アミノ、C2〜C4−アルカノイルアミノ、N−C1〜C4−アルキル カルバモイル及びN,N−ジ−C1〜C4−アルキルカルバモイルから選択された 置換基を3個まで有していてもよいフェニルである、請求 項1に記載の式Iのキナゾリン誘導体又はその製薬学的に認容性の塩。 7. X1が、直接結合であり; Q1は、メチル、アミノメチル、2−アミノエチル、メチルアミノメチル、2 −メチルアミノエチル、ジメチルアミノメチル、2−ジメチルアミノエチル、ピ ロリジン−1−イルメチル、2−ピロリジン−1−イルエチル、ピペリジノメチ ル、2−ピペリジノエチル、モルホリノメチル、2−モルホリノメチル、ピペラ ジン−1−イルメチル、2−ピペラジン−1−イルエチル、4−メチルピペラジ ン−1−イルメチル及び2−(4−メチルピペラジン−1−イル)エチルから選 択された置換基を有していてもよい2−チエニルであり; mは、1であり、R1は、水素又はメトキシであり; Q2は、フルオロ、クロロ、ブロモ、トリフルオロメチル、シアノ、メチル及 びメトキシから選択された置換基を1個、2個又は3個有していてもよいフェニ ルである、請求項1に記載の式Iのキナゾリン誘導体又はその製薬学的に認容性 の酸付加塩。 8. X1が、直接結合であり; Q1は、アミノメチル、モルホリノメチル及び2−モルホリノエチルから選択 された置換基を有していてもよい2−チエニルであり; mは、1であり、R1は、水素又はメトキシであり; Q2は、フルオロ、クロロ、ブロモ及びメチルから選択された置換基を1個又 は2個有していてもよいフェニルである、請求項1に記載の式Iのキナゾリン誘 導体又はその製薬学的に認容性の酸付加塩。 9. 4−(3−クロロ−4−フルオロアニリノ)−6−[5−(2−モルホリノ エチル)チエン−2−イル]キナゾリンである、請求項1に記載の式Iのキナゾ リン誘導体又はその製薬学的に認容性の酸付加塩。 10. X1が、直接結合であるか又は式:Oで示される基であり; Q1は、フルオロ、クロロ、ブロモ、アミノ、シアノ、ニトロ、アミノメチル 、メチルアミノメチル、ジメチルアミノメチル、ジエチルアミノメチル、ピロリ ジン−1−イルメチル、ピペリジノメチル、モルホリノメチル、ピペラジン−1 −イルメチル及び4−メチルピペラジン−1−イルメチルから選択された置換基 を1個又は2個有していてもよいフェニルであり; Q2は、フルオロ、クロロ、ブロモ、トリフルオロメチル、シアノ、メチル及 びメトキシから選択された置換基1個、2個又は3個を有していてもよいフェニ ルであるか又はQ2は、式II:〔式中、X2は、式:OCH2で示される基であり、 Q3は、2−ピリジルであり、nは、1であり、R4は、水素、フルオロ、クロ ロ又はメチルである〕で示される基である、請求項1に記載の式Iのキナゾリン 誘導体又はその製薬学的に認容性の酸付加塩。 11. X1が、直接結合であるか又は式:Oで示される基であり; Q1は、アミノ、アミノメチル、ジエチルアミノメチル、ピロリジン−1−イ ルメチル、ピペリジノメチル及びモルホリノメチルから選択された置換基1個又 は2個を有していてもよいフェニルであり; mは、1であり、R1は、水素であり; Q2は、フルオロ、クロロ及びメチルから選択された置換基1個又は2個を有 していてもよいフェニルである、請求項1に記載の式Iのキナゾリン誘導体又は その製薬学的に認容性の酸付加塩。 12. 4−(3−メチルアニリノ)−6−フェニルキナゾリン、6−(4−アミ ノメチルフェニル)−4−(3−クロロ−4−フルオロアニリノ)キナゾリン、 6−(4−アミノフェノキシ)−4−(3−クロ ロ−4−フルオロアニリノ)キナゾリン、6−(4−アミノメチルフェノキシ) −4−(3−クロロ−4−フルオロアニリノ)キナゾリン又は4−(3−クロロ −4−フルオロアニリノ)−6-(4−モルホリノメチルフェノキシ)キナゾリ ンから選択された、請求項1に記載の式Iのキナゾリン誘導体又はその製薬学的 に認容性の酸付加塩。 13. 請求項1から12までのいずれか1項に記載の式Iのキナゾリン誘導体又 はその製薬学的に認容性の塩の製造法において、 (a)式III: 〔式中、Zは、置換可能な基である〕で示されるキナゾリンと式:Q2− NH2で示されるアニリンとの反応: (b)X1が、直接結合である式Iの前記化合物の製造のための式IV: 〔式中、Zは、置換可能な基である〕で示されるキナゾリンと式:Q1− B(L1)(L2)〔式中、L1及びL2のそれぞれは、同一であるか又は異なって いてもよく、適当な配位子である〕で示される有機ホウ素試薬との反応; (c)X1が、直接結合である式Iの前記化合物の製造のための式V: 〔式中、L1及びL2のそれぞれは、同一であるか又は異なっていてもよく 、適当な配位子である〕で示されるキナゾリンと式:Q1−Z〔式中、Zは、置 換可能な基である〕で示される化合物との反応; (d)好ましくは、X1が、式:N(R2)CO又は N(R2)SO2で示される基である式Iの前記化合物の製造のための、式 :Q1−CO2Hで示されるカルボン酸又はその反応性誘導体あるいは式:Q1− SO2OHで示されるスルホン酸又はその反応性誘導体を用いる式VI: で示されるアミンのアシル化; (e)X1が、式:OC(R2)2、SC(R2)2又はN(R2)C(R2)2で示さ れる基である式Iの前記化合物の製造のための、式:Z−C(R2)2−Q1〔式 中、Zは、置換可能な基である〕で示されるアルキル化剤を用いる、適当なフェ ノール、チオフェノール又はアニリンのアルキル化; (f)X1が、式:C(R2)2O、C(R2)2S又はC(R2)2N(R2)で示さ れる基である式Iの前記化合物の製造のための、式VII 〔式中、Zは、置換可能な基である〕で示されるアルキル化剤を用いる、 式:HO−Q1で示される適当なフェノール、式:SH−Q1で示されるチオフェ ノール又は式:R2NH−Q1で示されるアニリンのアルキル化; (g)好ましくは、アミノメチル置換基を有するか又はX1が、式:N(R2)C H2又はCH2N(R2)で示される基である式Iの前記化合物の製造のための、 シアノ置換基を有するか又はX1が、式:N(R2)CO又はCON(R2)で示 される基である式Iの化合物の還元; (h)アミノ置換基を有する式Iの前記化合物の製造のための、ニトロ置換基を 有する式Iの化合物の還元; (i)X1が、式:NHCH(R2)で示される基である式Iの前記化合物の製造 のための、式VIII: で示されるアミンを用いる、式R2−CO−Q1で示されるケト化合物の還元 アミン化又は (j)X1が、式:O、S又はN(R2)で示される基である式Iの前記化合 物の製造のための、式Z−Q1〔式中、Zは、置換可能な基である〕で示される 化合物を用いる、適当なフェノール、チオフェノール又はアニリンのカップリン グからなり、 式Iのキナゾリン誘導体の製薬学的に認容性の塩が必要である場合には、常 法を用いる前記化合物の反応によって得ることができることを特徴とする、請求 項1から12までのいずれか1項に記載の式Iのキナゾリン誘導体又はその製薬 学的に認容性の塩の製造法。 14.請求項1から12までのいずれか1項に記載の式Iのキナゾリン誘導体又は その製薬学的に認容性の塩とともに製薬学的に認容性の希釈剤又は担持剤を含有 する医薬調剤において、 15.温血動物、例えばヒトにおいて抗増殖性効果の発 生に使用するための医薬品の製造の際の、請求項1から12までのいずれか1項 に記載の式Iのキナゾリン誘導体又はその製薬学的に認容性の塩の使用。
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- 1997-02-10 ES ES97902496T patent/ES2239351T3/es not_active Expired - Lifetime
- 1997-02-10 WO PCT/GB1997/000344 patent/WO1997030034A1/en active IP Right Grant
- 1997-02-10 AT AT97902496T patent/ATE293103T1/de active
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JP2005515176A (ja) * | 2001-11-03 | 2005-05-26 | アストラゼネカ アクチボラグ | 抗腫瘍剤としてのキナゾリン誘導体 |
JP2005511603A (ja) * | 2001-11-03 | 2005-04-28 | アストラゼネカ アクチボラグ | 抗腫瘍薬としてのキナゾリン誘導体 |
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JP2010518045A (ja) * | 2007-02-06 | 2010-05-27 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 二環式へテロ環、それらの化合物を含む薬剤、その使用及びその製法 |
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JP2019206549A (ja) * | 2014-12-15 | 2019-12-05 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | Egfr及びpi3kの小分子阻害剤 |
KR102139496B1 (ko) | 2014-12-15 | 2020-07-30 | 더 리젠츠 오브 더 유니버시티 오브 미시간 | Egfr 및 pi3k의 소분자 억제제 |
US10842791B2 (en) | 2014-12-15 | 2020-11-24 | The Regents Of The University Of Michigan | Small molecule inhibitors of EGFR and PI3K |
US11607414B2 (en) | 2014-12-15 | 2023-03-21 | The Regents Of The University Of Michigan | Small molecule inhibitors of EGFR and PI3K |
JP2019519580A (ja) * | 2016-06-30 | 2019-07-11 | ギリアード サイエンシーズ, インコーポレイテッド | Cotモジュレーターとしての4,6−ジアミノキナゾリン類およびその使用方法 |
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Also Published As
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ZA971231B (en) | 1997-08-14 |
US20030018029A1 (en) | 2003-01-23 |
EP0880507B1 (en) | 2005-04-13 |
JP4074342B2 (ja) | 2008-04-09 |
NO983707D0 (no) | 1998-08-13 |
KR100494824B1 (ko) | 2005-11-23 |
ATE293103T1 (de) | 2005-04-15 |
IL125685A0 (en) | 1999-04-11 |
GB9603095D0 (en) | 1996-04-10 |
DE69733008D1 (de) | 2005-05-19 |
DE69733008T2 (de) | 2006-02-16 |
NZ330816A (en) | 2000-05-26 |
US6399602B1 (en) | 2002-06-04 |
EP0880507A1 (en) | 1998-12-02 |
US6897214B2 (en) | 2005-05-24 |
ES2239351T3 (es) | 2005-09-16 |
US5866572A (en) | 1999-02-02 |
IL125685A (en) | 2002-11-10 |
NO983707L (no) | 1998-10-13 |
CN1211240A (zh) | 1999-03-17 |
AU707339B2 (en) | 1999-07-08 |
MY119992A (en) | 2005-08-30 |
KR19990082583A (ko) | 1999-11-25 |
PT880507E (pt) | 2005-07-29 |
CN1142919C (zh) | 2004-03-24 |
WO1997030034A1 (en) | 1997-08-21 |
NO311936B1 (no) | 2002-02-18 |
AU1612697A (en) | 1997-09-02 |
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