JPH10506894A - 新しいプロスタグランジンシンターゼ阻害剤 - Google Patents
新しいプロスタグランジンシンターゼ阻害剤Info
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- JPH10506894A JPH10506894A JP8511934A JP51193496A JPH10506894A JP H10506894 A JPH10506894 A JP H10506894A JP 8511934 A JP8511934 A JP 8511934A JP 51193496 A JP51193496 A JP 51193496A JP H10506894 A JPH10506894 A JP H10506894A
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.下記式I: 〔式中、J、KおよびLは独立してCR3、CR4またはNであり; Xは単結合(即ちXは存在しない)、-(CHR5)2-、-CH=CR5-、-CH5=CR-、-C ≡C-、-(CHR5)pZ-、-Z(CHR5)p-、-C(=O)CH2または-CH2C(=O)-であり; ZはOまたはSであり; R1は0-2 R7で置換されたフェニル、0-2 R7で置換された2−ナフチル、0-1 R9で置換されたC5-C7シクロアルキル、 C5-C7シクロアルケニルただしR1が直接ヘテロ原子に連結している場合は、 そのヘテロ原子はシクロアルケン環における二重結合を有する炭素には連結して いない、 フリル、チエニル、ピロリル、チアゾリル、オキサゾリル、N−メチルピロ リル、イソオキサゾリル、イソチアゾリル、ピラゾリル、3−ピリジニル、ピリ ダジニル、ピラジニル、インドリル、ベンゾフラニル、ベンゾチエニル、ベンゾ チアゾリル、ベンゾオキサゾリル、ベンゾトリアゾリル、ベンゾイソチアゾリル 、ベンゾイソオキサゾリル、キノリニル、イソキノリニルまたはピペリジニルか ら選択される5〜10員の複素環系、ただし前記複素環系は0-2 R7で置換されてい るものであり; R2は であり; Yは-CH3またはNH2であり; R3はH、F、Br、Cl、I、CN、0-1 R12で置換されたC1-C4アルキル、C1-C4 ハロアルキル、0-1 R13で置換されたC1-C4アルケニル、NO2、NR15R16、S(O)mR11 、SO2NR15aR16、-C(=O)R6、-COOR17、-C(=O)NR15aR16またはOR18であり; R4はH、F、Br、Cl、I、C1-C2アルキル、C1-C2アルコキシ、C1-C2ハロア ルキル、-CF3、-SR10aであるか;または R3およびR4が隣接する炭素原子上の置換基である場合は、R3とR4はそれらが 連結している炭素原子と一緒になって5〜7員の炭素環または複素環系を形成し 、その複素環系はN、OまたはSから選択されるヘテロ原子1〜3個を有するも のであり; R5はC1-C2アルキル、C1-C2アルコキシまたはC1-C2ハロアルキルであり; R6は、水素、0-1 R14で置換されたC1-C6アルキル、0-2 R9で置換されたフェ ニル、0-1 R9で置換されたC5-C7シクロアルキル、 フリル、チエニル、チアゾリル、オキサゾリル、N−メチルピロリル、イソ オキサゾリル、イソチアゾリル、ピラゾリル、ピリジニル、ピペリダジニル、ピ ラジニルまたはピリミジニルから選択される5〜10員の複素環系、ただし前記複 素環系は0-2 R7で置換されているものであり; R7はH、F、Br、Cl、I、C1-C4アルキル、フェニル、CH2OH、 CH2OCH3、C1-C4アルコキシ、C1-C4ハロアルキル、-SR10、NRl5R16、-C(=O)R10、 CH2COOR17またはOR19から選択される炭素上の置換基であるが、ただし、Xが単 結合である場合は、R7はXに対してオルト位ではなく; R8はH、F、Br、Cl、I、ヒドロキシ、C1-C4アルキル、C1-C4アルコキシ、 -(CH2)nCOOR17または-CH=CHCOOR17であり; R9はH、F、Br、Cl、I、ヒドロキシ、C1-C4アルキルまたはC1-C4アルコキ シであり; R10はHまたはC1-C4アルキルであり; R11はC1-C4アルキル、C1-C2フルオロアルキル、フェニルまたはベンジルで あり; R12はF、OR18、NR15R16、0-2 R9で置換されたフェニル、-CN、-C(=O)R6、- COOR17、-C(=O)NR15R16、またはモルホリニル、ピペリジニル、ピロリジニル、 フリル、チエニル、ピリジニル、ピペリダジニル、ピリミジニル、ピラジニルま たはテトラヒドロピリジニルから選択される複素環系であり、この複素環系は0- 2 R9で置換されており; R13は-CN、-C(=O)R6、-COOR17、-NO2またはNR15R16であり; R14はF、OH、C1-C4アルコキシ、NH2、0-2 R9で置換されたフェニル、アル キルカルボニル、アリールカルボニル、-COOR7または-C(=O)NH2であり; R15はH、0-1 R23で置換されたC1-C4アルキル、C6-C10アリール、C3-C7シク ロアルキル、C4-C11シクロアルキルアルキル、C2-C4アルケニル、C1-C4アルコキ シ、C1-C6アルキルカルボニル、C1-C6アルコキシカルボニル、C7-C14アリールア ルコキシカルボ ニル、C6-C10アリールオキシカルボニル、C1-C6アルキルアミノカルボニル、C6- C10アリールカルボニル、C1-C6アルキルスルホニル、C6-C10アリールスルホニル 、C7-C14アルキルアリールスルホニル、C7-C14アリールアルキルスルホニルであ り; R15aはH、0-1 R23で置換されたC1-C4アルキル、C6-C10アリール、C3-C7シ クロアルキル、C4-C11シクロアルキルアルキル、C2-C4アルケニル、C1-C4アルコ キシであり; R16はHまたはC1-C4アルキルであるか;または R15とR16は一緒になって-(CH2)4-、-(CH2)5-、-(CH2)2O(CH2)2-または-(CH2 )2-NR21(CH2)2-を形成し; R17はC1-C4アルキルまたはアリールアルキルであり; R18は0-2 R24で置換されたC1-C4アルキル、C6-C10アリール、C3-C7シクロア ルキル、C1-C6アルキルカルボニル、C1-C6アルキルアミノカルボニル、C7-C14ア リールアルキルカルボニルまたは0-2 R9で置換されたC6-C10アリールカルボニル であり; R19はC1-C4アルキル、C1-C4ハロアルキル、C1-C4アルコキシアルキル、C1-C6 アルキルカルボニル、C1-C6アルキルアミノカルボニル、C7-C14アリールアルキ ルカルボニルまたは0-2 R9で置換されたC6-C10アリールカルボニルであり; R20はH、C1-C4アルキル、C1-C4ハロアルキル、C1-C4アルコキシアルキル、 C6-C10アリール、C3-C7シクロアルキル、C1-C6アルキルカルボニル、C1-C6アル キルアミノカルボニル、C7-C14アリールアルキルカルボニルまたは0-2 R9で置換 されたC6-C10アリールカルボニルであり; R21はC1-C4アルキルまたはベンジルであり; R22はH、R2、R1、C1-C4アルキル、C4-C10シクロアルキルアルキル、C7-C14 アリールアルキルまたはC6-C10ヘテロアリールアルキルであり; R23はH、F、0-2 R9で置換されたフェニル、-C(=O)R6、-COOR17、-C(=O)NH R16またはモルホリニル、ピペリジニル、ピロリジニル、フリル、チエニルまた はテトラヒドロピリジニルから選択される複素環系であり、この複素環系は0-2 R9で置換されており; R24は、H、F、NR15R16、0-2 R9で置換されたフェニル、C1-C4アルコキシ 、C1-C4アルキルカルボニルオキシ、C(=O)R6、-COOR17、-C(=O)NR15R16であるか 、またはモルホリニル、ピペリジニル、ピロリジニル、フリル、チエニル、ピペ リジニルまたはテトラヒドロピリジニルから選択される複素環系であり、この複 素環系は0-2 R9で置換されており; mは0〜2であり;そして、 pは0〜1であるが; ただし、JおよびLが共に窒素でありKがCR4である場合は、R4はSR10では ない〕の化合物または薬学的に許容されるその塩またはプロドラッグ。 2.JがCHまたはNであり; KおよびLの各々が独立してCR3またはCR4であり; Xは単結合(即ちXは存在しない)、-C≡C-、または-(CHR5)pZ-であり; R3はH、F、Br、CN、0-1 R12で置換されたC1-C4アルキル、C1-C4ハロアル キル、NO2、SOmR11、-C(=O)R6またはOR18であり; R4はH、F、CH3であるか、または R3およびR4が隣接する炭素原子上の置換基である場合は、R3とR4はそれらが 連結されている炭素原子と一緒になって5〜7員の炭素環系を形成し; R6は、水素、0-1 R14で置換されたC1-C6アルキル、または0-2 R9で置換され たフェニルであり;そして R7はH、F、Br、C1-C4アルキル、CH2OH、CH2OCH3、C1-C4アルコキシ、C1-C4 ハロアルキル、NR15R16または-C(=O)R10から選択される炭素上の置換基である ような請求項1記載の化合物または薬学的に許容されるその塩またはプロドラ ッグ。 3.R8がHであり; R9がHであり; R12がF、OR18、CN、-COOR17であり; R14がHであり; R15がHまたはC1-C4アルキルであり; R16がHまたはC1-C4アルキルであり; R18がHまたはC1-C4アルキルであり; R19がC1-C4アルキルである ような請求項2記載の化合物または薬学的に許容されるその塩またはプロドラ ッグ。 4.下記式Ia: 〔式中R1Xはフェニル、4−フルオロフェニル、3−メトキシフェニル、4− メトキシフェニル、3,4−ジメトキシフェニル、4−ヒドロキシメチルフェニル 、4−メトキシメチルフェニル、4−ジメチルアミノフェニル、4−ホルミルフ ェニル、2−ナフチル、5−メトキシ−2−ナフチル、2−キノリニル、3−キ ノリニル、2−ベンゾチエニル、5−ベンゾチエニル、3−ピリジル、フェニル アセチレニル、フェノキシ、シクロヘキセニル、シクロヘキシル、4−フルオロ フェノキシ、シクロヘキシルオキシ、ベンジルオキシ、1−ピロリルまたは1− ピペリジニルであり;そして、 R3は水素、4−ヒドロキシ、4−ニトロ、5−ニトロまたは4−アセトであ る〕の請求項1記載の化合物。 5.R1Xがフェニルであり;そして R3が水素、4−ヒドロキシ、4−ニトロ、5−ニトロまたは4−アセトであ るか、または R1が4−フルオロフェニル、3−メトキシフェニル、4−メトキシフェニル 、3,4−ジメトキシフェニル、4−ヒドロキシメチルフェニル、4−メトキシメ チルフェニル、4−ジメチルアミノフェニル、4−ホルミルフェニル、2−ナフ チル、5−メトキシ−2−ナフチル、2−キノリニル、3−キノリニル、2−ベ ンゾチエニル、5−ベンゾチエニル、3−ピリジル、フェニルアセチレニル、フ ェノキシ、シクロヘキセニル、シクロヘキシル、4−フルオロフェノキシ、シク ロヘキシルオキシ、ベンジルオキシ、1−ピロリルまたは1−ピペリジニルであ り;そして R3は水素である ような請求項4記載の化合物または薬学的に許容されるその塩またはプロドラ ッグ。 6.2−(4−メチルスルホニルフェニル)−3−フェニルナフタレン、3−( 4−メチルスルホニルフェニル)−2−フェニルピリジル、および2−(4−ア ミノスルホニルフェニル)−1−ビフェニルである請求項1記載の化合物。 7.請求項1記載の化合物の抗炎症量および薬学的に許容される担体を含有する 薬学的組成物。 8.請求項2の化合物の抗炎症量および薬学的に許容される担体を含有する薬学 的組成物。 9.請求項3の化合物の抗炎症量および薬学的に許容される担体を含有する薬学 的組成物。 10.請求項4の化合物の抗炎症量および薬学的に許容される担体を含有する薬学 的組成物。 11.請求項5の化合物の抗炎症量および薬学的に許容される担体を含有する薬学 的組成物。 12.請求項1の化合物の有効量哺乳類に投与することを包含する哺乳類における プロスタグランジンHシンターゼを阻害する方法。 13.請求項1記載の化合物の治療有効量を炎症性疾患の治療の必要な哺乳類に投 与することを包含する哺乳類における上記疾患の治療方法。 14.請求項1記載の化合物の治療有効量を発熱性疾患の治療の必要な哺乳類に投 与することを包含する哺乳類における上記疾患の治療方法。
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Cited By (2)
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JP2012184222A (ja) * | 2011-02-14 | 2012-09-27 | Asahi Kasei E-Materials Corp | ハロゲン原子を有する多環式芳香族化合物の製造方法 |
JP2012184223A (ja) * | 2011-02-14 | 2012-09-27 | Asahi Kasei E-Materials Corp | 多環式芳香族化合物の製造方法 |
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UA70275C2 (en) | 2004-10-15 |
DE69512797T2 (de) | 2000-04-27 |
CA2200707A1 (en) | 1996-04-04 |
EP0783486B1 (en) | 1999-10-13 |
US5593994A (en) | 1997-01-14 |
CZ87297A3 (cs) | 1998-02-18 |
KR100367378B1 (ko) | 2003-11-22 |
WO1996010012A1 (en) | 1996-04-04 |
HUT77344A (hu) | 1998-03-30 |
ES2139943T3 (es) | 2000-02-16 |
MX9701893A (es) | 1997-06-28 |
AU3640995A (en) | 1996-04-19 |
GR3031763T3 (en) | 2000-02-29 |
FI116568B (fi) | 2005-12-30 |
SK283023B6 (sk) | 2003-02-04 |
BR9509212A (pt) | 1998-01-27 |
EP0783486A1 (en) | 1997-07-16 |
NZ293859A (en) | 1998-08-26 |
SK40497A3 (en) | 1998-05-06 |
JP3753434B2 (ja) | 2006-03-08 |
CZ296974B6 (cs) | 2006-08-16 |
PL180948B1 (pl) | 2001-05-31 |
US5932586A (en) | 1999-08-03 |
PL319385A1 (en) | 1997-08-04 |
AU703105B2 (en) | 1999-03-18 |
CA2200707C (en) | 2006-08-08 |
HU227862B1 (en) | 2012-05-02 |
DK0783486T3 (da) | 2000-01-31 |
RU2184109C2 (ru) | 2002-06-27 |
DE69512797D1 (en) | 1999-11-18 |
FI971312A (fi) | 1997-03-27 |
FI971312A0 (fi) | 1997-03-27 |
CN1125044C (zh) | 2003-10-22 |
ATE185558T1 (de) | 1999-10-15 |
CN1166167A (zh) | 1997-11-26 |
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