JPH08508974A - アニリド誘導体 - Google Patents
アニリド誘導体Info
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- JPH08508974A JPH08508974A JP6502977A JP50297794A JPH08508974A JP H08508974 A JPH08508974 A JP H08508974A JP 6502977 A JP6502977 A JP 6502977A JP 50297794 A JP50297794 A JP 50297794A JP H08508974 A JPH08508974 A JP H08508974A
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- 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
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- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/70—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a saturated carbon skeleton containing rings
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- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
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- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
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- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
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- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes 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 in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
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- 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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- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
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- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 下記式(I)の化合物、およびその生理学上許容される塩ならびに溶媒 和物を含むその塩および溶媒和物。 〔上記式中: Aは、酸素、イオウ原子、結合または基(CH2)lNR7(ここで、lは0ま たは1を表し、R7は水素原子またはメチル基を表す)を表し、 Bは、ヒドロキシル基で場合により置換されていてもよいC1-4アルキレン鎖 を表し、但しAが酸素、イオウ原子または基(CH2)lNR7を表す場合に、ヒ ドロキシル基および部分Aは同一炭素原子に結合していてはならず、またAが結 合を表す場合に、BはまたC2-4アルケニレン鎖をも表し、 R1は、水素原子、またはC1-4アルキル基を表し、 mは、1または2を表し、 R2は、水素、ハロゲン原子、C1-4アルキル、C1-4アルコキシ、またはC1-4 アルキルチオ基を表し、 R3は、水素原子、またはC1-4アルコキシ基を表し、 R4は、水素原子、C1-4アルキル、またはC1-4アルコキシ基を表し、 R5は、水素原子を表すか、またはR1およびR5は一緒になって基‐(CH2)n ‐(ここで、nは1または2を表す)を形成し、 R6は、水素原子、またはC1-4アルコキシ基を表し、 下記基 はカルボキサミド置換基に対してベンゼン環の3または4位に結合しているが、 但しこの基がベンゼン環の3位に結合している場合には、R4はベンゼン環の6 位に結合していなければならず、 Zは、Het、 または のいずれかを表し、 Hetは、キノリン‐4‐イル、イソキノリン‐1‐イル、イソキノリン‐3‐ イル、キノリン‐3‐イル、キノリン‐2‐イル、キノキサリン‐2‐イル、ナ フタレン‐1‐イル、ナフタレン‐2‐イル、インドール‐2‐イル、4‐オキ ソ‐4H‐1‐ベンゾピラン‐2‐イル、フェナジン‐1‐イル、およびフェノ チアジン‐1‐イルから選択される場合により置換されていてもよい二環式また は三環式環、または2‐アリール‐4‐チアゾリル、2‐アリール‐5‐チアゾ リル、5‐アリール‐2‐チエニル、2‐アリール‐4‐チアゾリル、および1 ‐アリール‐4‐ピラゾリルから選択されるアリール置換単環式環を表す(ここ で、アリールはハロゲン原子、トリフルオロメチル、C1-4アルキルまたはC1-4 アルコキシ基で場合により置換されていてもよいフェニルまたはピリジル環を表 す)。上記二環式または三環式環は、C1-4アルキルおよびC1-4アルコキシから 選択される1、2または3つの基で置換されていてもよく、 あるいは非置換であってもよい。キノリン‐4‐イル環もまた、フェニルまたは C1-4アルコキシで置換されたフェニルにより環2位で置換されていてよい。イ ンドール‐2‐イル環もまた、ベンゾイルにより環3位で置換されていてよい。 R8は、水素、ハロゲン原子、C1-4アルキル、C1-4アルコキシ、C1-4アルキ ルチオ、アミノ、またはニトロ基を表し、 pは1を表すか、あるいはR8がC1-4アルコキシを表す場合には、pは2また は3をも表し、 R9は、水素、ハロゲン原子、C1-4アルキル、C1-4アルコキシ、またはC1-4 アルキルチオ基を表し、 R10およびR11は各々水素原子を表すか、あるいは一緒になって結合または‐ O‐もしくは‐S‐から選択される結合原子を形成し、 Xは、酸素原子またはNR12を表す(ここで、R12は水素原子またはC1-4ア ルキル基を表す)〕。 2. R2およびR3が各々C1-4アルコキシ基を表し、R6が水素原子を表す、 請求項1に記載の化合物。 3. R4が水素原子を表す、請求項1または2に記載の化合物。 4. mが1を表し、R1およびR5が一緒になって基‐(CH2)2‐を形成し ている、請求項1〜3のいずれか一項に記載の化合物。 5. 下記式(Ia)の化合物: (上記式中、Zは請求項1で定義されたとおりであり、 Aは、酸素、イオウ原子、または結合を表し、 Bは、非置換C1-4アルキレン鎖を表し、 R2およびR3は各々独立してC1-4アルコキシ基を表す)、およびその生理学上 許容される塩ならびに溶媒和物。 6. Zが請求項1で定義されたようなHetを表す、請求項5に記載の化合物 。 7. Zが (上記式中、R8は水素、ハロゲン原子、C1-4アルキル、C1-4アルコキシ、C1 -4 アルキルチオ、またはニトロ基を表し、R9は水素、ハロゲン原子、C1-4アル キル、C1-4アルコキシ、またはC1-4アルキルチオ基を表し、R10およびR11は 請求項1で既に定義されたとおりである)を表す、請求項5に記載の化合物。 8. Zが (上記式中、R8は水素、ハロゲン原子、C1-4アルキル、C1-4アルコキシ、C1 -4 アルキルチオ、またはニトロ基を表し、R9は水素、ハロゲン原子、C1-4アル キル、C1-4アルコキシ、またはC1-4アルキルチオ基を表し、Xは酸素原子また はNHを表す)を表す、請求項5に記載の化合物。 9. R8が水素、フッ素原子、C1-4アルコキシ、またはC1-4アルキル基を 表し、R9が水素原子を表す、請求項7または8に記載の化合物。 10. 治療に用いられる、請求項1〜9のいずれか一項に記載の化合物。 11. 抗腫瘍剤の効力を改善または増加させるか、抗腫瘍剤に対する腫瘍の 感受性を増加または復活させるか、または抗腫瘍剤に対する腫瘍の耐性を逆転ま たは減少させる、癌にかかった哺乳動物の治療に用いられる、請求項1〜9のい ずれか一項に記載の化合物。 12. 抗腫瘍剤の効力を改善または増加させるか、抗腫瘍剤に対する腫瘍の 感受性を増加または復活させる か、または抗腫瘍剤に対する腫瘍の耐性を逆転または減少させる、癌にかかった 哺乳動物の治療用薬剤の製造のための、請求項1〜9のいずれか一項に記載の化 合物の使用。 13. 抗腫瘍剤の効力を改善または増加させるか、抗腫瘍剤に対する腫瘍の 感受性を増加または復活させるか、または抗腫瘍剤に対する腫瘍の耐性を逆転ま たは減少させるために、請求項1〜9のいずれか一項に記載の化合物の有効量を 哺乳動物に投与することを含んでなる、癌にかかった哺乳動物の治療方法。 14. 請求項1〜9のいずれか一項に記載の化合物を1種以上の生理学上許 容されるキャリアまたは賦形剤とともに含んでなる、医薬組成物。 15. 抗腫瘍剤の効力を改善または増加させるか、抗腫瘍剤に対する腫瘍の 感受性を増加または復活させるか、または抗腫瘍剤に対する腫瘍の耐性を逆転ま たは減少させる、癌にかかった哺乳動物の治療に用いられる、請求項1〜9のい ずれか一項に記載の化合物の活性量を含んでなる医薬組成物。 16. 経口、経口腔、非経口または直腸投与用に適した形態の、請求項14 または15に記載の医薬組成物。 17. 単位剤形の、請求項14〜16のいずれか一項に記載の医薬組成物。 18. 癌を治療する上で同時、別々、または逐次使用のための組合せ製剤と しての、請求項1〜9のいずれか一項に記載の化合物と抗腫瘍剤とを含有してな る製品。 19. 癌を治療する上で、ヒトまたは非ヒト動物の体内に互いに存在する、 請求項1〜9のいずれか一項に記載の化合物および抗腫瘍剤。 20. 抗腫瘍剤が、ビンカアルカロイド類、アントラサイクリン類、タキソ ールおよびその誘導体、ポドフィロトキシン類、ミトキサントロン、アクチノマ イシン、コルヒチン、グラミシジンD、アムサクリンまたはいわゆるMDR表現 型で特徴付けられる上記薬物との交差耐性を有する薬物である、請求項11〜1 9(請求項14を除く)のいずれか一項に記載の製品または方法。 21. 請求項1に記載の化合物の製造方法であって、 (A)下記式(II)の化合物: Z‐CO2H (II) をカップリング試薬の存在下で、下記式(III)の化合物: と反応させるか、または (B)下記式(IV)の化合物: (上記式中Qはハロゲン原子を表す)を酸受容体の存在下で、下記式(V)の化 合物: またはその塩と反応させ、工程(A)または(B)の後に任意工程として塩形成さ せることを含んでなる、方法。 22. 実質上本明細書で記載されている、請求項1〜9のいずれか一項に記 載の化合物。 23. 実質上本明細書で記載されている、請求項14〜17のいずれか一項 に記載の組成物。
Applications Claiming Priority (6)
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GB9214668.7 | 1992-07-10 | ||
GB929214675A GB9214675D0 (en) | 1992-07-10 | 1992-07-10 | Chemical compounds |
GB9214667.9 | 1992-07-10 | ||
GB929214667A GB9214667D0 (en) | 1992-07-10 | 1992-07-10 | Chemical compounds |
GB929214668A GB9214668D0 (en) | 1992-07-10 | 1992-07-10 | Chemical compounds |
GB9214675.2 | 1992-07-10 |
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US (1) | US5663179A (ja) |
EP (1) | EP0649410B1 (ja) |
JP (1) | JP2718830B2 (ja) |
AT (1) | ATE152443T1 (ja) |
AU (1) | AU4567193A (ja) |
DE (1) | DE69310367T2 (ja) |
DK (1) | DK0649410T3 (ja) |
ES (1) | ES2103479T3 (ja) |
GR (1) | GR3024073T3 (ja) |
WO (1) | WO1994001408A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003508524A (ja) * | 1999-09-03 | 2003-03-04 | インデナ・ソチエタ・ペル・アツィオーニ | フラボン類、キサントン類およびクマリン類の新規誘導体 |
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Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5387685A (en) * | 1993-07-16 | 1995-02-07 | American Cyanamid Co | MDR reversal agents |
GB2311781B (en) * | 1994-12-23 | 1998-09-16 | Xenova Ltd | Piperazine 2,5 dione derivatives as modulators of multi-drug resistance |
GB9426224D0 (en) * | 1994-12-23 | 1995-02-22 | Xenova Ltd | Pharmaceutical compounds |
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GB9426071D0 (en) * | 1994-12-23 | 1995-02-22 | Xenova Ltd | Pharmaceutical compounds |
GB2310854B (en) * | 1994-12-23 | 1998-09-09 | Xenova Ltd | Piperazine-2,5-dione derivatives as modulators of multi-drug resistance |
AU1597197A (en) * | 1996-02-01 | 1997-08-22 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Thienoquinolines |
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JP6746569B2 (ja) | 2014-10-07 | 2020-08-26 | バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated | 嚢胞性線維症膜貫通コンダクタンス制御因子のモジュレーターの共結晶 |
KR20230104151A (ko) | 2020-10-07 | 2023-07-07 | 아테넥스, 인크. | 아세트아미도-페닐테트라졸 유도체 및 그의 사용 방법 |
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Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0172744A2 (en) * | 1984-08-16 | 1986-02-26 | Development Finance Corporation Of New Zealand | Phenazinecarboxamide compounds |
NZ212525A (en) * | 1985-06-24 | 1989-02-24 | Dfc New Zealand Ltd Formerly D | Nitrogen-containing heterocyclic compounds, and pharmaceutical compositions containing such |
AU652996B2 (en) * | 1991-01-11 | 1994-09-15 | Laboratoires Glaxo S.A. | Acridine derivatives |
-
1993
- 1993-07-08 DK DK93915865.5T patent/DK0649410T3/da active
- 1993-07-08 JP JP6502977A patent/JP2718830B2/ja not_active Expired - Fee Related
- 1993-07-08 US US08/356,323 patent/US5663179A/en not_active Expired - Lifetime
- 1993-07-08 ES ES93915865T patent/ES2103479T3/es not_active Expired - Lifetime
- 1993-07-08 EP EP93915865A patent/EP0649410B1/en not_active Expired - Lifetime
- 1993-07-08 AU AU45671/93A patent/AU4567193A/en not_active Abandoned
- 1993-07-08 DE DE69310367T patent/DE69310367T2/de not_active Expired - Fee Related
- 1993-07-08 WO PCT/EP1993/001802 patent/WO1994001408A1/en active IP Right Grant
- 1993-07-08 AT AT93915865T patent/ATE152443T1/de not_active IP Right Cessation
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003508524A (ja) * | 1999-09-03 | 2003-03-04 | インデナ・ソチエタ・ペル・アツィオーニ | フラボン類、キサントン類およびクマリン類の新規誘導体 |
JP4782337B2 (ja) * | 1999-09-03 | 2011-09-28 | インデナ・ソチエタ・ペル・アツィオーニ | フラボン類、キサントン類およびクマリン類の新規誘導体 |
JP2013032357A (ja) * | 2006-12-07 | 2013-02-14 | China Medical Univ | 2−セレノフェン−4−キノロンの化合物および抗癌剤としてのこの使用 |
JP2012504149A (ja) * | 2008-09-29 | 2012-02-16 | サートリス ファーマシューティカルズ, インコーポレイテッド | サーチュインモジュレーターとしてのキナゾリノン、キノロンおよび関連するアナログ |
Also Published As
Publication number | Publication date |
---|---|
US5663179A (en) | 1997-09-02 |
EP0649410A1 (en) | 1995-04-26 |
GR3024073T3 (en) | 1997-10-31 |
DE69310367T2 (de) | 1997-08-14 |
DE69310367D1 (de) | 1997-06-05 |
EP0649410B1 (en) | 1997-05-02 |
DK0649410T3 (da) | 1997-09-15 |
ES2103479T3 (es) | 1997-09-16 |
ATE152443T1 (de) | 1997-05-15 |
JP2718830B2 (ja) | 1998-02-25 |
AU4567193A (en) | 1994-01-31 |
WO1994001408A1 (en) | 1994-01-20 |
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