(57)【要約】  ＭＭＰ−１３の活性を阻害し得るならば、その活性に起因または関連する病態、特に変形性関節症（ＯＡ）の改善、あるいは進行の防止に大きく寄与すると考えられることから、ＭＭＰ−１３阻害剤の開発が望まれている。  一般式（Ｉ）：2007102392.tif 000056（式中、Ｒ１は、置換されていてもよいアリール等；Ｚは、置換されていてもよく置換基群ａから選択される置換基を介在していてもよいＣ１−Ｃ５アルキレン等；Ａは、式：2007102392.tif 000057（Ｒ６およびＲ７はそれぞれ独立して、ハロゲン、低級アルキル等；ｍおよびｎはそれぞれ独立しては、０、１、または２）；Ｒ２は、水素原子、置換されていてもよい低級アルキル等；Ｒ３は、水素原子、置換されていてもよい低級アルキル等；Ｒ４は、水素原子；またはＲ３およびＲ４は一緒になって、隣接する炭素原子と共に環を形成してもよい；Ｒ５は、ヒドロキシ、低級アルキルオキシ等）で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物、およびそれらを有効成分として含有するＭＭＰ−１３阻害活性を有する医薬組成物を提供する。
2007102392.tif 000002
【特許請求の範囲】
【請求項１】
一般式（Ｉ）：
【化１】
2007102392.tif 000048
［式中、Ｒ１は、置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよい非芳香族炭素環基、または置換されていてもよい非芳香族複素環基；
Ｚは、−Ｏ−、−Ｓ−、−ＳＯ−、−ＳＯ２−、−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−ＳＯ２−、−ＳＯ２−Ｎ（Ｒ１０）−、−Ｃ（＝Ｏ）−、−Ｏ−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｏ−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｓ）−Ｎ（Ｒ１０）−、−Ｏ−Ｎ＝Ｃ（Ｒ８）−、−Ｃ（Ｒ８）＝Ｎ−Ｏ−、−Ｏ−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｏ−、−Ｃ（＝Ｏ）−Ｃ（＝Ｏ）−、置換されていてもよい非芳香族炭素環基、置換されていてもよい非芳香族複素環基、置換されていてもよく置換基群ａから選択される置換基を介在していてもよいＣ１−Ｃ５アルキレン、置換されていてもよく置換基群ａから選択される置換基を介在していてもよいＣ１−Ｃ５アルケニレン、または置換されていてもよく置換基群ａから選択される置換基を介在していてもよいＣ１−Ｃ５アルキニレン、ここで置換基群ａとは−Ｏ−、−Ｓ−、−ＳＯ−、−ＳＯ２−、−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−ＳＯ２−、−ＳＯ２−Ｎ（Ｒ１０）−、−Ｃ（＝Ｏ）−、−Ｏ−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｏ−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｓ）−Ｎ（Ｒ１０）−、−Ｏ−Ｎ＝Ｃ（Ｒ８）−、−Ｃ（Ｒ８）＝Ｎ−Ｏ−、−Ｏ−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｏ−、および−Ｃ（＝Ｏ）−Ｃ（＝Ｏ）−からなり、Ｒ８およびＲ１０はそれぞれ独立して、水素原子または低級アルキル；
Ａは、式：
【化２】
2007102392.tif 000049
（式中、Ｒ６およびＲ７はそれぞれ独立して、ハロゲン、低級アルキル、シクロアルキル、低級アルケニル、低級アルキニル、低級アルキルオキシ、低級アルケニルオキシ、低級アルキルチオ、ハロ低級アルキル、ハロ低級アルキルオキシ、ハロ低級アルキルチオ、ヒドロキシ、ヒドロキシ低級アルキル、メルカプト、カルボキシ、低級アルキルオキシカルボニル、低級アルキルスルホニル、アシル、アシルオキシ、ニトロ、シアノ、置換されていてもよいアミノ、または置換されていてもよいアミノカルボニル；Ｂ環はさらに窒素原子、酸素原子、および／または硫黄原子を環内に含んでいてもよい含窒素複素環；ｍおよびｎはそれぞれ独立しては、０〜３の整数）で示される基；
Ｒ２は、水素原子、置換されていてもよい低級アルキル、置換されていてもよいアラルキル、または置換されていてもよいヘテロアリールアルキル、置換されていてもよいアリール、または置換されていてもよいヘテロアリール；
Ｒ３は、水素原子、置換されていてもよい低級アルキル、置換されていてもよいアラルキル、置換されていてもよいヘテロアリールアルキル、置換されていてもよいアリール、または置換されていてもよいヘテロアリール；
Ｒ４は、水素原子；または 
Ｒ３およびＲ４は一緒になって、隣接する炭素原子と共に、５〜６員の非芳香族炭素環または５〜６員の非芳香族複素環を形成してもよい； 
Ｒ５は、ヒドロキシ、低級アルキルオキシ、または−ＮＨＯＨ；
ただし、Ｂ環がピペラジンおよびＺが−ＣＨ２−Ｏ−の時、Ｒ１はピリジルではない］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【請求項２】
一般式（ＩＩ）：
【化３】
2007102392.tif 000050
（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｚ、ｍ、ｎ、およびＢ環は請求項１と同意義）で示される請求項１記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【請求項３】
一般式（ＩＩＩ）：
【化４】
2007102392.tif 000051
（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｚ、ｍ、ｎ、およびＢ環は請求項１と同意義）で示される請求項１記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【請求項４】
Ｒ１が、置換されていてもよいナフチルまたは置換されていてもよいカルバゾリルである請求項１記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【請求項５】
Ｒ１が、式：
【化５】
2007102392.tif 000052
（式中Ｒ２４は水素原子；カルボキシもしくは低級アルキルオキシイミノで置換されていてもよい低級アルキル；カルボキシで置換されていてもよい低級アルケニル；ヒドロキシ；シクロアルキル、ヒドロキシ、低級アルキルオキシ、カルボキシ、もしくは１ないし２の低級アルキルで置換されていてもよいアミノカルボニルで置換されていてもよい低級アルキルオキシ；カルボキシ；アシル；1ないし２のアシルもしくは低級アルキルスルホニルで置換されていてもよいアミノ；1ないし２の低級アルキルで置換されていてもよいアミノカルボニル；または非芳香族複素環；
Ｒ２５はハロゲン、シアノ、またはアシル；
ｎ１は０〜２の整数であり、Ｒ２５は置換可能な全ての環構成原子上で置換しうる）で示される基である請求項１記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【請求項６】
Ｚが、−Ｃ（Ｒ８）（Ｒ９）−、−Ｏ−、−Ｓ−、−ＳＯ−、−ＳＯ２−、−Ｎ（Ｒ１０）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）＝Ｃ（Ｒ９）−、−Ｃ≡Ｃ−、−Ｏ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｏ−、−Ｓ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｓ−、−ＳＯ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ−、−ＳＯ２−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ２−、−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−ＳＯ２−、−ＳＯ２−Ｎ（Ｒ１０）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（＝Ｏ）−Ｃ（＝Ｏ）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）＝Ｃ（Ｒ９）−、−Ｃ（Ｒ８）＝Ｃ（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ≡Ｃ−、−Ｃ≡Ｃ−Ｃ（Ｒ８）（Ｒ９）−、−Ｏ−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｏ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−Ｏ−、−Ｓ−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｓ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−Ｓ−、−ＳＯ−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−ＳＯ−、−ＳＯ２−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ２−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−ＳＯ２−、−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−、−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−、−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−ＳＯ２−、−Ｎ（Ｒ１０）−ＳＯ２−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ２−Ｎ（Ｒ１０）−、−ＳＯ２−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｓ）−Ｎ（Ｒ１０）−、−Ｏ−Ｎ＝Ｃ（Ｒ８）−、−Ｃ（Ｒ８）＝Ｎ−Ｏ−、−Ｏ−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−Ｏ−、−Ｏ−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、または−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｏ−（式中、Ｒ８、Ｒ９およびＲ１０はそれぞれ独立して、水素原子または低級アルキル）である請求項１記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【請求項７】
式：
【化６】
2007102392.tif 000053
で示される基が、式：
【化７】
2007102392.tif 000054
（式中、Ｘは炭素原子または窒素原子、Ｃ環は５〜８員の含窒素複素環、Ｒ７およびｍは請求項１と同意義）で示される基である、請求項１記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【請求項８】
Ｒ２が水素原子である請求項１記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【請求項９】
Ｒ３が水素原子、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、s−ブチル、イソブチル、t−ブチル、ヒドロキシメチル、１−ヒドロキシエチル、２−ヒドロキシエチル、カルボキシメチル、カルボキシエチル、メチルオキシメチル、メチルチオメチル、２−メチルチオエチル、フェニル、４−ヒドロキシフェニル、４−フルオロフェニル、４−メチルオキシフェニル、ベンジル、４−ヒドロキシベンジル、４−フルオロベンジル、４−クロロベンジル、４−メトキシベンジル、インドール−３−イルメチル、１−カルボキシメチルインドール−３−イルメチル、チアゾール−４−イルメチル、カルボキシメチルオキシベンジル、またはシクロプロピルメチルであり、
Ｒ４が水素原子である；または、
Ｒ３およびＲ４が隣接する炭素と一緒に式：
【化８】
2007102392.tif 000055
で示される環を形成してもよい、
請求項１記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【請求項１０】
Ｒ５がヒドロキシである請求項１記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【請求項１１】
請求項１〜１０のいずれかに記載の化合物を有効成分として含有する医薬組成物。
【請求項１２】
請求項１〜１０のいずれかに記載の化合物を有効成分として含有するＭＭＰ−１３阻害活性を有する医薬組成物。
【請求項１３】
請求項１〜１０のいずれかに記載の化合物の治療上の効果を示す量を人を含む哺乳動物に投与することからなる、哺乳動物のＭＭＰ−１３に起因または関連する疾患を治療する方法。
【請求項１４】
ＭＭＰ−１３に起因または関連する疾患を治療するための医薬を製造するための請求項１〜１０のいずれかに記載の化合物の使用。
【発明の詳細な説明】
【技術分野】
【０００１】
本発明は、ＭＭＰ−１３を選択的に阻害するスルホンアミド誘導体に関する。
【背景技術】
【０００２】
細胞外マトリックスは、コラーゲン、フィブロネクチン、ラミニン、プロテオグリカン等から構成され、組織支持機能、細胞の増殖、分化、接着等の役割を持つ。細胞外マトリックスの分解には、活性中心に金属イオンを含むプロテアーゼであるメタロプロテアーゼ、特にマトリックスメタロプロテアーゼ（ＭＭＰ）が関与している。ＭＭＰにはＭＭＰ−１（Ｉ型コラゲナーゼ）からＭＭＰ−２８まで多くのファミリーが報告され、本来の生理条件下では成長、組織代謝等に作用している。しかし、組織破壊や線維化を伴う各種病態（変形性関節症、関節リウマチ、角膜潰瘍、歯周病、腫瘍の転移又は浸潤、ウイルス感染症（ＨＩＶ感染症））では病態の進行と前記酵素の発現（活性）上昇が相関していることが報告されている。
ＭＭＰ阻害作用を有するスルホンアミド誘導体が、特許文献１、特許文献２、特許文献３および非特許文献１等に記載されている。
ＭＭＰ−１２阻害作用を有し、置換基としてナフチル基を有するスルホンアミド誘導体が、特許文献４に記載されている。
置換基としてナフチル基を有するチアゾールまたはオキサゾールスルホンアミド誘導体が、特許文献５に記載されている。
置換基としてナフチル基を有するチアゾールまたはオキサゾールスルホンアミド誘導体が、特許文献６に記載されている。
アグリカナーゼ阻害作用を有し、置換基としてナフチル基を有するスルホンアミド誘導体が特許文献７に記載されている。
アグリカナーゼ阻害作用およびＭＭＰ−１３阻害作用を有するスルホンアミド誘導体が特許文献８に記載されている。
アグリカナーゼ阻害作用およびＭＭＰ阻害作用を有するスルホンアミド誘導体が特許文献９に記載されている。
ＴＮＦ−α阻害作用およびＭＭＰ阻害作用を有するスルホンアミド誘導体が特許文献１０に記載されている。
【特許文献１】国際公開第９７／２７１７４パンフレット
【特許文献２】国際公開第９９／０４７８０パンフレット
【特許文献３】国際公開第００／１５２１３パンフレット
【特許文献４】国際公開第０１／８３４３１パンフレット
【特許文献５】国際公開第０２／２８８４４パンフレット
【特許文献６】国際公開第０１／８３４６１パンフレット
【特許文献７】国際公開第０３／０８００４２パンフレット
【特許文献８】特開２０００−３１９２５０号公報
【特許文献９】国際公開第０５／０６１４５９パンフレット
【特許文献１０】国際公開第９８／３２７４８パンフレット
【非特許文献１】田村嘉則ら、ジャーナル  オブ  メディシナル  ケミストリー (J. Med. Chem.) 1998年、第41巻、第４号、p.640-649
【発明の開示】
【発明が解決しようとする課題】
【０００３】
ＭＭＰ−１３の活性を阻害し得るならば、その活性に起因または関連する病態、特に変形性関節症（ＯＡ）の改善、あるいは進行の防止に大きく寄与すると考えられることから、ＭＭＰ−１３阻害剤の開発が望まれている。
【課題を解決するための手段】
【０００４】
本発明者らは以上の点に鑑み、鋭意検討を重ねた結果、ある種の新規なスルホンアミド誘導体が、ＭＭＰ−１３選択的阻害活性を示すことを見出し、以下の発明を完成した。【０００５】
本発明は、１）一般式（Ｉ）： 
【化１】
2007102392.tif 000003
［式中、Ｒ１は、置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよい非芳香族炭素環基、または置換されていてもよい非芳香族複素環基；
Ｚは、−Ｏ−、−Ｓ−、−ＳＯ−、−ＳＯ２−、−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−ＳＯ２−、−ＳＯ２−Ｎ（Ｒ１０）−、−Ｃ（＝Ｏ）−、−Ｏ−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｏ−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｓ）−Ｎ（Ｒ１０）−、−Ｏ−Ｎ＝Ｃ（Ｒ８）−、−Ｃ（Ｒ８）＝Ｎ−Ｏ−、−Ｏ−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｏ−、−Ｃ（＝Ｏ）Ｃ（＝Ｏ）−、置換されていてもよい非芳香族炭素環基、置換されていてもよい非芳香族複素環基、置換されていてもよく置換基群ａから選択される置換基を介在していてもよいＣ１−Ｃ５アルキレン、置換されていてもよく置換基群ａから選択される置換基を介在していてもよいＣ１−Ｃ５アルケニレン、または置換されていてもよく置換基群ａから選択される置換基を介在していてもよいＣ１−Ｃ５アルキニレン、ここで置換基群ａとは−Ｏ−、−Ｓ−、−ＳＯ−、−ＳＯ２−、−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−ＳＯ２−、−ＳＯ２−Ｎ（Ｒ１０）−、−Ｃ（＝Ｏ）−、−Ｏ−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｏ−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｓ）−Ｎ（Ｒ１０）−、−Ｏ−Ｎ＝Ｃ（Ｒ８）−、−Ｃ（Ｒ８）＝Ｎ−Ｏ−、−Ｏ−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｏ−、および−Ｃ（＝Ｏ）Ｃ（＝Ｏ）−からなり、Ｒ８およびＲ１０はそれぞれ独立して、水素原子または低級アルキル；
Ａは、式：
【化２】
2007102392.tif 000004
（式中、Ｒ６およびＲ７はそれぞれ独立して、ハロゲン、低級アルキル、シクロアルキル、低級アルケニル、低級アルキニル、低級アルキルオキシ、低級アルケニルオキシ、低級アルキルチオ、ハロ低級アルキル、ハロ低級アルキルオキシ、ハロ低級アルキルチオ、ヒドロキシ、ヒドロキシ低級アルキル、メルカプト、カルボキシ、低級アルキルオキシカルボニル、低級アルキルスルホニル、アシル、アシルオキシ、ニトロ、シアノ、置換されていてもよいアミノ、または置換されていてもよいアミノカルボニル；Ｂ環はさらに窒素原子、酸素原子、および／または硫黄原子を環内に含んでいてもよい含窒素複素環；ｍおよびｎはそれぞれ独立して０〜３の整数）で示される基；
Ｒ２は、水素原子、置換されていてもよい低級アルキル、置換されていてもよいアラルキル、または置換されていてもよいヘテロアリールアルキル、置換されていてもよいアリール、または置換されていてもよいヘテロアリール；
Ｒ３は、水素原子、置換されていてもよい低級アルキル、置換されていてもよいアラルキル、置換されていてもよいヘテロアリールアルキル、置換されていてもよいアリール、または置換されていてもよいヘテロアリール；
Ｒ４は、水素原子；または 
Ｒ３およびＲ４は一緒になって、隣接する炭素原子と共に、５〜６員の非芳香族炭素環または５〜６員の非芳香族複素環を形成してもよい； 
Ｒ５は、ヒドロキシ、低級アルキルオキシ、または−ＮＨＯＨ；
ただし、Ｂ環がピペラジンおよびＺが−ＣＨ２−Ｏ−の時、Ｒ１はピリジルではない］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物、に関する。【０００６】
さらに詳しくは、以下の２）〜２７）に関する。
２）一般式（ＩＩ）：
【化３】
2007102392.tif 000005
（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｚ、ｍ、ｎ、およびＢ環は前記１）と同意義）で示される前記１）記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。【０００７】
３）一般式（ＩＩＩ）：
【化４】
2007102392.tif 000006
（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｚ、ｍ、ｎ、およびＢ環は前記１）と同意義）で示される前記１）記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。【０００８】
４）Ｒ１が、置換されていてもよいナフチルまたは置換されていてもよいカルバゾリルである前記１）〜３）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
５）Ｒ１が、置換されていてもよいナフチルである前記１）〜３）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
６）Ｒ１が、式：
【化５】
2007102392.tif 000007
（式中Ｒ２４は水素原子；カルボキシもしくは低級アルキルオキシイミノで置換されていてもよい低級アルキル；カルボキシで置換されていてもよい低級アルケニル；ヒドロキシ；シクロアルキル、ヒドロキシ、低級アルキルオキシ、カルボキシ、もしくは１ないし２の低級アルキルで置換されていてもよいアミノカルボニルで置換されていてもよい低級アルキルオキシ；カルボキシ；アシル；1ないし２のアシルもしくは低級アルキルスルホニルで置換されていてもよいアミノ；1ないし２の低級アルキルで置換されていてもよいアミノカルボニル；または非芳香族複素環；
Ｒ２５はハロゲン、シアノ、またはアシル；
ｎ１は０〜２の整数であり、Ｒ２５は置換可能な全ての環構成原子上で置換しうる）で示される基である前記５）記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、ｎ１が０である化合物が好ましい。
７）Ｒ１が、式：
【化６】
2007102392.tif 000008
（式中Ｒ２４、Ｒ２５、およびｎ１は前記６）と同意義）で示される基である前記５）記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、ｎ１が０である化合物が好ましい。
８）Ｒ１が、式：
【化７】
2007102392.tif 000009
（式中Ｒ２４、Ｒ２５、およびｎ１は前記６）と同意義）で示される基である前記５）記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、ｎ１が０である化合物が好ましい。
９）Ｒ２４が水素原子、低級アルキルオキシ、またはアミノである前記６）〜８）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
１０）Ｒ１が、置換されていてもよいカルバゾリルである前記１）〜３）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、Ｒ１が非置換のカルバゾリルである化合物が好ましい。【０００９】
１１）Ｚが、−Ｃ（Ｒ８）（Ｒ９）−、−Ｏ−、−Ｓ−、−ＳＯ−、−ＳＯ２−、−Ｎ（Ｒ１０）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）＝Ｃ（Ｒ９）−、−Ｃ≡Ｃ−、−Ｏ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｏ−、−Ｓ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｓ−、−ＳＯ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ−、−ＳＯ２−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ２−、−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−ＳＯ２−、−ＳＯ２−Ｎ（Ｒ１０）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（＝Ｏ）Ｃ（＝Ｏ）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）＝Ｃ（Ｒ９）−、−Ｃ（Ｒ８）＝Ｃ（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ≡Ｃ−、−Ｃ≡Ｃ−Ｃ（Ｒ８）（Ｒ９）−、−Ｏ−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｏ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−Ｏ−、−Ｓ−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｓ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−Ｓ−、−ＳＯ−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−ＳＯ−、−ＳＯ２−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ２−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−ＳＯ２−、−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−、−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−、−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−ＳＯ２−、−Ｎ（Ｒ１０）−ＳＯ２−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ２−Ｎ（Ｒ１０）−、−ＳＯ２−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｓ）−Ｎ（Ｒ１０）−、−Ｏ−Ｎ＝Ｃ（Ｒ８）−、−Ｃ（Ｒ８）＝Ｎ−Ｏ−、−Ｏ−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−Ｏ−、−Ｏ−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、または−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−Ｏ−（式中、Ｒ８、Ｒ９およびＲ１０はそれぞれ独立して、水素原子または低級アルキル）である前記１）〜１０）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
１２）Ｚが、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）＝Ｃ（Ｒ９）−、−Ｃ≡Ｃ−、−Ｏ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｏ−、−Ｓ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｓ−、−ＳＯ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ−、−ＳＯ２−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ２−、−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−ＳＯ２−、−ＳＯ２−Ｎ（Ｒ１０）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−、または−Ｃ（＝Ｏ）Ｃ（＝Ｏ）−（式中、Ｒ８、Ｒ９およびＲ１０はそれぞれ独立して、水素原子または低級アルキル）である前記１）〜１０）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
１３）Ｚが、−ＣＨ２−ＣＨ２−、−ＣＨ＝ＣＨ−、−Ｃ≡Ｃ−、−Ｏ−ＣＨ２−、または−ＣＨ２−Ｏ−である前記１）〜１０）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
１４）Ｚが、−Ｃ≡Ｃ−である前記１）〜１０）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。【００１０】
１５）式：
【化８】
2007102392.tif 000010
で示される基が、式：
【化９】
2007102392.tif 000011
（式中、Ｘは炭素原子または窒素原子、Ｃ環は５〜８員の含窒素複素環、Ｒ７およびｍは前記１）と同意義）で示される基である、前記１）〜１４）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
１６）式：
【化１０】
2007102392.tif 000012
で示される基が、式：
【化１１】
2007102392.tif 000013
（式中、Ｒ７およびｍは前記１）と同意義）で示される基である、前記１）〜１４）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
１７）Ｒ２が水素原子である前記１）〜１６）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
１８）Ｒ３が水素原子、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、s−ブチル、イソブチル、t−ブチル、ヒドロキシメチル、１−ヒドロキシエチル、２−ヒドロキシエチル、カルボキシメチル、カルボキシエチル、メチルオキシメチル、メチルチオメチル、２−メチルチオエチル、フェニル、４−ヒドロキシフェニル、４−フルオロフェニル、４−メチルオキシフェニル、ベンジル、４−ヒドロキシベンジル、４−フルオロベンジル、４−クロロベンジル、４−メトキシベンジル、インドール−３−イルメチル、１−カルボキシメチルインドール−３−イルメチル、チアゾール−４−イルメチル、カルボキシメチルオキシベンジル、またはシクロプロピルメチルであり、
Ｒ４が水素原子である；または、
Ｒ３およびＲ４が隣接する炭素と一緒に式：
【化１２】
2007102392.tif 000014
で示される環を形成してもよい、前記１）〜１７）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
１９）Ｒ３が水素原子、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、s−ブチル、イソブチル、t−ブチル、ヒドロキシメチル、１−ヒドロキシエチル、２−ヒドロキシエチル、カルボキシメチル、カルボキシエチル、メチルオキシメチル、メチルチオメチル、２−メチルチオエチル、フェニル、４−ヒドロキシフェニル、４−フルオロフェニル、４−メチルオキシフェニル、ベンジル、４−ヒドロキシベンジル、４−フルオロベンジル、４−クロロベンジル、４−メトキシベンジル、インドール−３−イルメチル、１−カルボキシメチルインドール−３−イルメチル、チアゾール−４−イルメチル、カルボキシメチルオキシベンジル、またはシクロプロピルメチルであり、
Ｒ４が水素原子である前記１）〜１７）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
２０）Ｒ５がヒドロキシである前記１）〜１９）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。【００１１】
２１）前記１）〜２０）のいずれかに記載の化合物を有効成分として含有する医薬組成物。
２２）前記１）〜２０）のいずれかに記載の化合物を有効成分として含有するＭＭＰ−１３阻害活性を有する医薬組成物。
２３）前記１）〜２０）のいずれかに記載の化合物を有効成分として含有する変形性関節症の治療又は予防剤。
２４）前記１）〜２０）のいずれかに記載の化合物の治療上の効果を示す量を人を含む哺乳動物に投与することからなる、哺乳動物のＭＭＰ−１３に起因または関連する疾患を治療する方法。
２５）前記１）〜２０）のいずれかに記載の化合物の治療上の効果を示す量を人を含む哺乳動物に投与することからなる、哺乳動物の変形性関節症を治療する方法。
２６）ＭＭＰ−１３に起因または関連する疾患を治療するための医薬を製造するための前記１）〜２０）のいずれかに記載の化合物の使用。
２７）変形性関節症を治療するための医薬を製造するための前記１）〜２０）のいずれかに記載の化合物の使用。【００１２】
本明細書中、単独でもしくは他の用語と組み合わせて用いられる「低級アルキル」なる用語は、炭素原子数１〜８の直鎖または分枝鎖の１価の炭化水素基を包含する。例えば、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、イソブチル、ｓ−ブチル、ｔ−ブチル、ｎ−ペンチル、イソペンチル、ｎｅｏ−ペンチル、ｎ−ヘキシル、イソヘキシル、ｎ−ヘプチル、ｎ−オクチル等が挙げられる。好ましくは、Ｃ１〜Ｃ６アルキルが挙げられる。さらに好ましくは、Ｃ１〜Ｃ３アルキルが挙げられる。
本明細書中、「シクロアルキル」とは、炭素原子数が３〜８個であるシクロアルキルを包含する。例えば、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチルが挙げられる。好ましくはＣ３〜Ｃ６シクロアルキルが挙げられる。
本明細書中、単独でもしくは他の用語と組み合わせて用いられる「低級アルケニル」とは、炭素原子数が２〜８個であり、１個もしくは２個以上の二重結合を有する、直鎖または分枝鎖の１価の炭化水素基を包含する。例えば、ビニル、アリル、プロペニル、クロトニル、イソペンテニル、種々のブテニル異性体等が挙げられる。好ましくは、Ｃ２〜Ｃ６アルケニルが挙げられる。さらに好ましくは、Ｃ２〜Ｃ４アルケニルが挙げられる。
本明細書中、「シクロアルケニル」とは、炭素原子数が３〜８個であり、環内に１個もしくは２個以上の二重結合を有する、シクロアルケニルを包含する。例えば、シクロプロペニル、シクロブテニル、シクロペンテニル、シクロヘキセニル、シクロヘプテニル、シクロオクテニルが挙げられる。好ましくはＣ３〜Ｃ６シクロアルケニルが挙げられる。
本明細書中、「低級アルキニル」とは、炭素原子数が２〜８個であり、１個もしくは２個以上の三重結合を有する、直鎖または分枝鎖の１価の炭化水素基を包含し、二重結合を有していてもよい。例えば、エチニル、２−プロピニル、３−ブチニル、４−ペンチニル、５−ヘキシニル、６−ヘプチニル、７−オクチニル等が挙げられる。好ましくは、Ｃ２〜Ｃ６アルキニルが挙げられる。さらに好ましくは、Ｃ２〜Ｃ４アルキニルが挙げられる。
本明細書中、「シクロアルキニル」とは、炭素原子数が４〜８個であり、環内に１個もしくは２個以上の三重結合を有する、シクロアルキニルを包含し、二重結合を有していてもよい。例えば、シクロブチニル、シクロペンチニル、シクロヘキシニル、シクロヘプチニル、シクロオクチニルが挙げられる。好ましくはＣ３〜Ｃ６シクロアルキニルが挙げられる。
本明細書中、「アルキレン」とは前記「低級アルキル」に対応する２価の炭化水素基を包含する。
本明細書中、「アルケニレン」とは前記「低級アルケニル」に対応する２価の炭化水素基を包含する。
本明細書中、「アルキニレン」とは前記「低級アルキニル」に対応する２価の炭化水素基を包含する。
本明細書中、「置換基群ａから選択される置換基を介在したＣ１−Ｃ５アルキレン」とは、（置換基群ａから選択される置換基）−（Ｃ１−Ｃ５アルキレン）、（Ｃ１−Ｃ５アルキレン）−（置換基群ａから選択される置換基）、（アルキレン）−（置換基群ａから選択される置換基）−（アルキレン）（ただし、両アルキレン鎖の長さの合計は１〜５の整数）を包含する。【００１３】
本明細書中、単独でもしくは他の用語と組み合わせて用いられる「アリール」とは、単環状芳香族炭化水素基または２個ないし３個の芳香環が縮合している縮合環状芳香族炭化水素基を包含する。例えば、フェニル、１−ナフチル、２−ナフチル、アントリル等が挙げられる。
Ｒ１における「アリール」としてはナフチルが好ましい。特に、２−ナフチルが好ましい。
Ｒ２における「アリール」としてはフェニルが好ましい。
Ｒ３における「アリール」としてはフェニルが好ましい。
本明細書中、「ナフチル」とは、１−ナフチルおよび２−ナフチルを包含する。
本明細書中、単独でもしくは他の用語と組み合わせて用いられる「アラルキル」とは、前記「低級アルキル」に前記「アリ−ル」が１またはそれ以上置換したもので、これらは可能な全ての位置で置換しうる。例えば、ベンジル、フェニルエチル（例えば、２−フェニルエチル等）、フェニルプロピル（例えば、３−フェニルプロピル等）、ナフチルメチル（例えば、１−ナフチルメチル、２−ナフチルメチル等）、アントリルメチル（例えば、９−アントリルメチル等）、ビフェニルメチル（例えば、４−ビフェニルメチル等）等が挙げられる。好ましくは、ベンジル、フェニルエチルが挙げられる。
Ｒ２における「アラルキル」としてはフェニルＣ１〜Ｃ３アルキルが好ましい。特に、ベンジルが好ましい。
Ｒ３における「アラルキル」としては、フェニルＣ１〜Ｃ６アルキルおよびナフチルＣ１〜Ｃ６アルキルが好ましい。さらに好ましくは、フェニルＣ１〜Ｃ３アルキルおよびナフチルＣ１〜Ｃ３アルキルが挙げられる。例えば、ベンジル、フェニルエチル、１−ナフチルメチル、２−ナフチルメチルが挙げられる。【００１４】
本明細書中、単独でもしくは他の用語と組み合わせて用いられる「ヘテロアリール」とは、任意に選ばれる、酸素原子、硫黄原子又は窒素原子を環内に１個以上含む５〜６員の芳香環を包含し、これはシクロアルキル、アリール、非芳香族複素環、もしくは他のヘテロアリールと縮合していてもよく、これらは可能な全ての位置で縮合しうる。例えば、ピロリル（例えば、１−ピロリル、２−ピロリル、３−ピロリル）、フリル（例えば、２−フリル、３−フリル）、チエニル（例えば、２−チエニル、３−チエニル）、イミダゾリル（例えば、２−イミダゾリル、４−イミダゾリル）、ピラゾリル（例えば、１−ピラゾリル、３−ピラゾリル）、イソチアゾリル（例えば、３−イソチアゾリル）、イソオキサゾリル（例えば、３−イソオキサゾリル）、オキサゾリル（例えば、２−オキサゾリル）、チアゾリル（例えば、２−チアゾリル）、ピリジル（例えば、２−ピリジル、３−ピリジル、４−ピリジル）、ピラジニル（例えば、２−ピラジニル）、ピリミジニル（例えば、２−ピリミジニル、４−ピリミジニル）、ピリダジニル（例えば、３−ピリダジニル）、テトラゾリル（例えば、１Ｈ−テトラゾリル）、オキサジアゾリル（例えば、１，３，４−オキサジアゾリル）、チアジアゾリル（例えば、１，３，４−チアジアゾリル）、インドリジニル（例えば、２−インドリジニル、６−インドリジニル）、イソインドリル（例えば、２−イソインドリル）、インドリル（例えば、１−インドリル、２−インドリル、３−インドリル、５−インドリル、６−インドリル）、インダゾリル（例えば、３−インダゾリル）、プリニル（例えば、８−プリニル）、キノリジニル（例えば、２−キノリジニル）、イソキノリル（例えば、３−イソキノリル）、キノリル（例えば、２−キノリル、５−キノリル）、フタラジニル（例えば、１−フタラジニル）、ナフチリジニル（例えば、２−ナフチリジニル）、キノキサニル（例えば、２−キノキサニル）、キナゾリニル（例えば、２−キナゾリニル）、シンノリニル（例えば、３−シンノリニル）、プテリジニル（例えば、２−プテリジニル）、カルバゾリル（例えば、２−カルバゾリル、３−カルバゾリル）、フェナントリジニル（例えば、２−フェナントリジニル、３−フェナントリジニル）、アクリジニル（例えば、１−アクリニジル、２−アクリニジル）、ジベンゾフラニル（例えば、１−ジベンゾフラニル、２−ジベンゾフラニル、３−ジベンゾフラニル）、ベンゾイミダゾリル（例えば、２−ベンゾイミダゾリル）、ベンゾイソキサゾリル（例えば、３−ベンゾイソキサゾリル）、ベンゾオキサゾリル（例えば、２−ベンゾオキサゾリル）、ベンゾオキサジアゾリル（例えば、４−ベンゾオキサジアゾリル）、ベンゾイソチアゾリル（例えば、３−ベンゾイソチアゾリル）、ベンゾチアゾリル（例えば、２−ベンゾチアゾリル、５−ベンゾチアゾリル）、ベンゾフリル（例えば、２−ベンゾフリル、３−ベンゾフリル、５−ベンゾフリル）、ベンゾチエニル（例えば、２−ベンゾチエニル）、チエノピリミジニル等が挙げられる。
Ｒ１における「ヘテロアリール」としては、カルバゾリルが好ましい。
Ｒ２における「ヘテロアリール」としては、ピリジル、チエニル、フリル、イミダゾリル等が好ましい。
Ｒ３における「ヘテロアリール」としては、インドリル、イミダゾリル、フリル、チエニル等が好ましい。【００１５】
本明細書中、「ヘテロアリールアルキル」とは、前記「低級アルキル」の任意の位置に前記「ヘテロアリ−ル」が１または２以上置換したもので、これらは可能な全ての位置で置換しうる。例えば、オキサゾリルメチル（例えば、２−オキサゾリルメチル、４−オキサゾリルメチル）、チアゾリルメチル（例えば、２−チアゾリルメチル、４−チアゾリルメチル）、オキサゾリルエチル（例えば、５−オキサゾリル−２−エチル）、チアゾリルエチル（例えば、５−チアゾリル−２−エチル）、ベンゾオキサゾリルメチル（例えば、ベンゾオキサゾール−２−イルメチル）、ベンゾチアゾリルメチル（例えば、ベンゾチアゾール−２−イルメチル）、インドリルメチル（例えば、インドール−３−イルメチル）、イミダゾリルメチル（例えば、４−イミダゾリルメチル）、インダゾリルメチル（例えば、１−インダゾリルメチル）、ベンゾトリアゾリルメチル（例えば、１−ベンゾトリアゾリルメチル）、ベンゾキノリルメチル（例えば、２−ベンゾキノリルメチル）、ベンゾイミダゾリルメチル（例えば、ベンゾイミダゾール−２−メチル）、ピリジルメチル（例えば、４−ピリジルメチル）、フリルメチル（例えば、フラン−２−イルメチル）、チエニルメチル（例えば、チオフェン−２−イルメチル）等が挙げられる。
Ｒ２における「ヘテロアリールアルキル」としては、インドリルメチル（例えば、インドール−３−イルメチル）、イミダゾリルメチル（例えば、イミダゾール−５−イルメチル）、チエニルメチル（例えば、チオフェン−２−イルメチル）、チアゾリルメチル（例えば、２−チアゾリルメチル、４−チアゾリルメチル）、ピリジルメチル等が挙げられる。
Ｒ３における「ヘテロアリールアルキル」としては、インドリルメチル（例えば、インドール−３−イルメチル）、イミダゾリルメチル（例えば、イミダゾール−５−イルメチル）、ベンゾオキサゾリルメチル（例えば、ベンゾオキサゾール−２−イルメチル）、ベンゾチアゾリルメチル（例えば、ベンゾチアゾール−２−イルメチル）、ベンズイミダゾリルメチル（例えば、ベンゾイミダゾール−２−イルメチル）、チエニルメチル（例えば、チオフェン−２−イルメチル）、チアゾリルメチル（例えば、２−チアゾリルメチル、４−チアゾリルメチル）等が挙げられる。【００１６】
本明細書中、単独でもしくは他の用語と組み合わせて用いられる「非芳香族炭素環基」なる用語は、シクロアルキル、シクロアルケニルもしくはシクロアルキニルまたはそれらが前記「アリール」と縮合した環式基を包含する。例えば、シクロブチル、シクロペンチル、シクロヘキシル、インダニル、テトラヒドロナフチル等が挙げられる。
Ｚにおける「非芳香族炭素環基」としては、シクロブチルが好ましい。
Ｒ３およびＲ４が一緒になって隣接する炭素と共に５〜６員の非芳香族炭素環を形成する場合における「非芳香族炭素環」としては、シクロアルカン、シクロアルケンもしくはシクロアルキンが挙げられる。シクロペンタン、シクロヘキサン等が好ましい。
本明細書中、単独でもしくは他の用語と組み合わせて用いられる「非芳香族複素環基」なる用語は、任意に選ばれる、酸素原子、硫黄原子又は窒素原子を環内に１個以上含む非芳香族の５〜７員環もしくはそれらが２個以上縮合した環基、または前記「環」が前記「アリール」と縮合した環基を包含する。例えば、ピロリジニル（例えば、１−ピロリジニル、２−ピロリジニル）、ピロリニル（例えば、３−ピロリニル）、イミダゾリジニル（例えば、２−イミダゾリジニル）、イミダゾリニル（例えば、イミダゾリニル）、ピラゾリジニル（例えば、１−ピラゾリジニル、２−ピラゾリジニル）、ピラゾリニル（例えば、ピラゾリニル）、ピペリジル（例えば、ピペリジノ、２−ピペリジル）、ピペラジニル（例えば、１−ピペラジニル）、インドリニル（例えば、１−インドリニル）、イソインドリニル（例えば、イソインドリニル）、モルホリニル（例えば、モルホリノ、３−モルホリニル）、テトラヒドロキノリル、テトラヒドロフリル、テトラヒドロピラニル、１，３−ベンゾジオキソラニル、１，４−ベンゾジオキサニル、１−ベンゾオキソラニル、オキセタニル、アゼチジニル、ジアゼチジニル、クロマニル等が挙げられる。
Ｚにおける「非芳香族複素環基」としては、オキセタニル、アセチジニル、ジアゼチジニルが好ましい。
Ｒ３およびＲ４が一緒になって隣接する炭素と共に５〜６員の非芳香族複素環を形成する場合における「非芳香族複素環」としては、テトラヒドロピラン等が好ましい。【００１７】
Ｂ環における、「さらに窒素原子、酸素原子、および／または硫黄原子を環内に含んでいてもよい含窒素複素環」とは、Ｂ環上の窒素原子以外に、さらに窒素原子、酸素原子、および／または硫黄原子を環内に含んでいてもよい含窒素複素環を意味する。該「含窒素複素環」は、単環の５〜８員含窒素複素環、橋かけ環式の含窒素複素環を包含する。好ましくは、式：
【化１３】
2007102392.tif 000015
（式中、Ｘは炭素原子または窒素原子、Ｃ環は５〜８員の含窒素複素環または橋かけ環、Ｒ７はハロゲン、低級アルキル、シクロアルキル、低級アルケニル、低級アルキニル、低級アルキルオキシ、低級アルケニルオキシ、低級アルキルチオ、ハロ低級アルキル、ハロ低級アルキルオキシ、ハロ低級アルキルチオ、ヒドロキシ、ヒドロキシ低級アルキル、メルカプト、カルボキシ、低級アルキルオキシカルボニル、低級アルキルスルホニル、アシル、アシルオキシ、ニトロ、シアノ、置換されていてもよいアミノ、または置換されていてもよいアミノカルボニル；ｍは０〜３の整数）で示される含窒素複素環が挙げられる。さらに好ましくは、式：
【化１４】
2007102392.tif 000016
（式中Ｒ７およびｍは前記と同意義）で示される含窒素複素環が挙げられる。特に好ましくは、式：
【化１５】
2007102392.tif 000017
（式中Ｒ７およびｍは前記と同意義）で示される含窒素複素環が挙げられる。【００１８】
本明細書中、「ハロゲン」とはフッ素、塩素、臭素、およびヨウ素を意味する。好ましくは、フッ素、塩素、および臭素が挙げられる。
本明細書中、「低級アルキルオキシ」としては、メチルオキシ、エチルオキシ、ｎ−プロピルオキシ、イソプロピルオキシ、ｎ−ブチルオキシ、イソブチルオキシ、ｓ−ブチルオキシ、ｔ−ブチルオキシ、ｎ−ペンチルオキシ、ｎ−ヘキシルオキシ等が挙げられる。好ましくは、Ｃ１〜Ｃ６アルキルオキシが挙げられる。さらに好ましくは、Ｃ１〜Ｃ３アルキルオキシが挙げられる。
本明細書中、「低級アルケニルオキシ」としては、ビニルオキシ、アリルオキシ、プロペニルオキシ、３−ブテニルオキシ、２−ブテニルオキシ（クロトニルオキシ、イソクロトニルオキシ）、１−ブテニルオキシ、イソペンテニルオキシ等が挙げられる。Ｃ２〜Ｃ３アルケニルオキシが好ましい。
本明細書中、「低級アルキルチオ」としては、メチルチオ、エチルチオ、プロピルチオ、イソプロピルチオ、ブチルチオ、ｓ−ブチルチオ、イソブチルチオ、ｔ―ブチルチオ等が挙げられる。Ｃ１〜Ｃ３アルキルチオが好ましい。【００１９】
本明細書中、単独でもしくは他の用語と組み合わせて用いられる「ハロ低級アルキル」なる用語は、前記「ハロゲン」によって１〜８個所、好ましくは１〜５個所置換された前記「低級アルキル」を包含する。例えば、トリフルオロメチル、トリクロロメチル、ジフルオロエチル、トリフルオロエチル、ジクロロエチル、トリクロロエチル等が挙げられる。好ましくは、前記「ハロゲン」によって１〜５個所置換されたＣ１〜Ｃ３低級アルキルが挙げられる。特に好ましくは、トリフルオロメチルが挙げられる。
本明細書中、「ハロ低級アルキルオキシ」としては、前記「ハロゲン」によって１〜５個所置換されたＣ１〜Ｃ３低級アルキルオキシが好ましい。特に好ましくは、トリフルオロメチルオキシが挙げられる。
本明細書中、「ハロ低級アルキルチオ」としては、前記「ハロゲン」によって１〜５個所置換されたＣ１〜Ｃ３低級アルキルチオが好ましい。特に好ましくは、トリフルオロメチルチオが挙げられる。
本明細書中、「ヒドロキシ低級アルキル」なる用語は、ヒドロキシル基によって置換された前記「低級アルキル」を包含する。例えば、ヒドロキシメチル、１−ヒドロキシエチル、２−ヒドロキシエチル、１−ヒドロキプロピル、２−ヒドロキプロピル、３−ヒドロキシプルピル等が挙げられる。好ましくは、ヒドロキシメチル、１−ヒドロキシエチル、２−ヒドロキシエチルが挙げられる。
本明細書中、「低級アルキルオキシカルボニル」としては、メチルオキシカルボニル、エチルオキシカルボニル、ｎ−プロピルオキシカルボニル、イソプロピルオキシカルボニル等が挙げられる。
本明細書中、「低級アルキルスルホニル」としては、メチルスルホニル、エチルスルホニル等が挙げられる。好ましくはメチルスルホニルが挙げられる。
本明細書中、「アラルキルオキシ」としては、フェニルＣ１〜Ｃ３アルキルオキシ、ナフチルＣ１〜Ｃ３オキシ等が挙げられる。好ましくはベンジルが挙げられる。
本明細書中、「低級アルキルオキシ低級アルキル」なる用語は、前期「低級アルキルオキシ」によって置換された前記「低級アルキル」を包含する。例えば、メチルオキシメチル、エチルオキシメチル、プロピルオキシメチル、１−メチルオキシエチル、２−メチルオキシエチル、１−メチルオキシプロピル、２−メチルオキシプロピル、３−メチルオキシプロピル等が挙げられる。好ましくは、メチルオキシメチルが挙げられる。
本明細書中、「アリールオキシ低級アルキル」としては、フェニルオキシメチル、１−フェニルオキシエチル、２−フェニルオキシエチル、１−ナフチルオキシメチル、２−ナフチルオキシメチル等が挙げられる。
本明細書中、単独でもしくは他の用語と組み合わせて用いられる「アシル」なる用語は、アルキル部分が前記「低級アルキル」であるアルキルカルボニル、アリール部分が前記「アリール」であるアリールカルボニル、またはヘテロアリール部分が前記「ヘテロアリール」であるヘテロアリールカルボニルを包含する。例えば、アセチル、プロピオニル、ベンゾイル、ピリジルカルボニル等が挙げられる。「低級アルキル」および「アリール」は後述の置換基によって置換されていてもよい。
本明細書中、「アシルオキシ」としては、アセチルオキシ、プロピオニルオキシ、ベンゾイルオキシ等が挙げられる。【００２０】
本明細書中、単独でもしくは他の用語と組み合わせて用いられる「置換されていてもよいアミノ」とは、アミノまたは前記「低級アルキル」、前記「アラルキル」、前記「ヘテロアリールアルキル」、前記「低級アルキルスルホニル」、もしくは前記「アシル」で１または２個所置換されているアミノを包含する。好ましくは、非置換アミノ、またはＣ１〜Ｃ６アルキル、フェニルＣ１〜Ｃ３アルキル、ピリジルＣ１〜Ｃ３アルキル、Ｃ１〜Ｃ６アルキルスルホニル、Ｃ１〜Ｃ６アルキルカルボニルおよびアリールカルボニルからなる群から選択される１または２個の置換基で置換されているアミノが挙げられる。例えば、アミノ、メチルアミノ、ジメチルアミノ、エチルメチルアミノ、ジエチルアミノ、ベンジルアミノ、メチルスルホニルアミノ、アセチルアミノ、ベンゾイルアミノ等が挙げられる。好ましくはアミノ、メチルアミノ、ジメチルアミノ、エチルメチルアミノ、ジエチルアミノ、メチルスルホニルアミノ、アセチルアミノが挙げられる。
本明細書中、「置換されていてもよいアミノカルボニル」としては、非置換アミノカルボニル、またはＣ１〜Ｃ６アルキルで１または２個所置換されていてもよいアミノカルボニルが好ましい。アミノカルボニル、メチルアミノカルボニル、ジメチルアミノカルボニル、エチルメチルアミノカルボニル、ジエチルアミノカルボニル等が挙げられる。好ましくは、アミノカルボニル、ジメチルアミノカルボニルが挙げられる。【００２１】
本明細書中、「置換されていてもよい低級アルキル」における置換基としては、低級アルキルチオ、シクロアルキル、カルボキシ、低級アルキルオキシ、ヒドロキシ、メルカプト、ハロゲン、ニトロ、シアノ、低級アルキルオキシカルボニル、ハロ低級アルキル、ハロ低級アルキルオキシ、置換されていてもよいアミノ、置換されていてもよいアミノカルボニル、アシル、アシルオキシ、置換基群ｂから選択される置換基で置換されていてもよい非芳香族複素環基、アリールオキシ、アラルキルオキシ、低級アルキルスルホニル、グアニジノ、アゾ基、置換基群ｂから選択される置換基で置換されていてもよいウレイド、カルバモイル等が挙げられる。これらは、全ての可能な位置で１個以上置換しうる。
置換基群ｂ：低級アルキル、シクロアルキル、低級アルケニル、低級アルキニル、ヒドロキシ、低級アルキルオキシ、メルカプト、低級アルキルチオ、低級アルケニルオキシ、ハロゲン、ニトロ、シアノ、カルボキシ、低級アルキルオキシカルボニル、ハロ低級アルキル、ハロ低級アルキルオキシ、ハロ低級アルキルチオ、置換されていてもよいアミノ、置換されていてもよいアミノカルボニル、アシル、アシルオキシ、アリール、ヘテロアリ−ル、非芳香族複素環、アラルキル、低級アルキルスルホニル、グアニジノ、アゾ基、およびウレイド
Ｒ２における「置換されていてもよい低級アルキル」の置換基としては、ヒドロキシ、低級アルキルオキシ、置換基群ｂから選択される置換基で置換されていてもよい非芳香族複素環基が好ましい。
Ｒ３における「置換されていてもよい低級アルキル」の置換基としては、低級アルキルオキシ、低級アルキルチオ、シクロアルキル、カルボキシ、ハロゲン、ヒドロキシ、カルバモイル、メルカプトが好ましい。【００２２】
本明細書中、Ｒ２およびＲ３における「置換されていてもよいアリール」、「置換されていてもよいヘテロアリール」、「置換されていてもよいアラルキル」、および「置換されていてもよいヘテロアリールアルキル」における置換基としては、置換基群ｂから選択される置換基で置換されていてもよい低級アルキル、シクロアルキル、低級アルケニル、低級アルキニル、ヒドロキシ、低級アルキルオキシ、メルカプト、低級アルキルチオ、低級アルケニルオキシ、ハロゲン、ニトロ、シアノ、カルボキシ、低級アルキルオキシカルボニル、ハロ低級アルキル、ハロ低級アルキルオキシ、ハロ低級アルキルチオ、置換されていてもよいアミノ、置換されていてもよいアミノカルボニル、アシル、アシルオキシ、置換基群ｂから選択される置換基で置換されていてもよいアリール、置換基群ｂから選択される置換基で置換されていてもよいヘテロアリ−ル、置換基群ｂから選択される置換基で置換されていてもよい非芳香族複素環、置換基群ｂから選択される置換基で置換されていてもよいアラルキル、低級アルキルスルホニル、グアニジノ、アゾ基、または置換基群ｂから選択される置換基で置換されていてもよいウレイド等が挙げられる。これらは、全ての可能な位置で１個以上置換しうる。
置換基群ｂ：低級アルキル、シクロアルキル、低級アルケニル、低級アルキニル、ヒドロキシ、低級アルキルオキシ、メルカプト、低級アルキルチオ、低級アルケニルオキシ、ハロゲン、ニトロ、シアノ、カルボキシ、低級アルキルオキシカルボニル、ハロ低級アルキル、ハロ低級アルキルオキシ、ハロ低級アルキルチオ、置換されていてもよいアミノ、置換されていてもよいアミノカルボニル、アシル、アシルオキシ、アリール、ヘテロアリ−ル、非芳香族複素環、アラルキル、低級アルキルスルホニル、グアニジノ、アゾ基、およびウレイド
Ｒ２における「置換されていてもよいアリール」の置換基としては、ヒドロキシ、低級アルキルオキシ、ハロゲン、またはハロ低級アルキルが好ましい。
Ｒ３における「置換されていてもよいアリール」の置換基としては、ヒドロキシが好ましい。
Ｒ２における「置換されていてもよいヘテロアリール」の置換基としては、ヒドロキシ、低級アルキルオキシ、ハロゲン、またはハロ低級アルキルが好ましい。
Ｒ３における「置換されていてもよいヘテロアリール」の置換基としては、ヒドロキシまたはハロゲンが好ましい。
Ｒ２における「置換されていてもよいアラルキル」の置換基としては、ヒドロキシ、低級アルキルオキシ、ハロゲン、ハロ低級アルキル、またはニトロが好ましい。
Ｒ３における「置換されていてもよいアラルキル」の置換基としては、ヒドロキシ、ハロゲン、ニトロ、低級アルキルオキシ、ハロ低級アルキル、またはカルボキシ低級アルキルオキシが好ましい。
Ｒ２における「置換されていてもよいヘテロアリールアルキル」の置換基としては、ヒドロキシ、低級アルキルオキシ、ハロゲン、またはハロ低級アルキルが好ましい。
Ｒ３における「置換されていてもよいヘテロアリールアルキル」の置換基としては、ハロゲン、ヒドロキシ、またはカルボキシが好ましい。【００２３】
本明細書中、Ｒ１における「置換されていてもよいアリール」、「置換されていてもよいヘテロアリール」、「置換されていてもよい非芳香族炭素環基」、「置換されていてもよい非芳香族複素環基」、「置換されていてもよいナフチル」および「置換されていてもよいカルバゾリル」における置換基としては、ハロゲン、置換基群ｅから選択される置換基で置換されていてもよい低級アルキル、置換基群ｆから選択される置換基で置換されていてもよい低級アルキルオキシ、シクロアルキル、カルボキシで置換されていてもよい低級アルケニル、低級アルキニル、低級アルケニルオキシ、低級アルキルチオ、ハロ低級アルキル、ハロ低級アルキルオキシ、ハロ低級アルキルチオ、ヒドロキシ、ヒドロキシ低級アルキル、メルカプト、カルボキシ、低級アルキルオキシカルボニル、低級アルキルスルホニル、アシル、アシルオキシ、ニトロ、シアノ、オキソ、ヒドロキシイミノ、低級アルキルオキシイミノ、置換されていてもよいアミノ、置換されていてもよいアミノカルボニル、置換基群ｂから選択される置換基で置換されていてもよいアリール、置換基群ｂから選択される置換基で置換されていてもよいヘテロアリール、置換基群ｂから選択される置換基で置換されていてもよいアリールオキシ、置換基群ｂから選択される置換基で置換されていてもよいアラルキルオキシ、低級アルキルオキシ低級アルキル、置換基群ｂから選択される置換基で置換されていてもよいアリールオキシ低級アルキル、置換基群ｂから選択される置換基で置換されていてもよいウレイド、置換基群ｂから選択される置換基で置換されていてもよい非芳香族複素環基が挙げられる。これらは、全ての可能な位置で１個以上置換しうる。
置換基群ｂ：低級アルキル、シクロアルキル、低級アルケニル、低級アルキニル、ヒドロキシ、低級アルキルオキシ、メルカプト、低級アルキルチオ、低級アルケニルオキシ、ハロゲン、ニトロ、シアノ、カルボキシ、低級アルキルオキシカルボニル、ハロ低級アルキル、ハロ低級アルキルオキシ、ハロ低級アルキルチオ、置換されていてもよいアミノ、置換されていてもよいアミノカルボニル、アシル、アシルオキシ、アリール、ヘテロアリ−ル、非芳香族複素環、アラルキル、低級アルキルスルホニル、グアニジノ、アゾ基、およびウレイド
置換基群ｅ：カルボキシ、シアノ、低級アルキルオキシイミノ、および置換されていてもよいアミノカルボニル
置換基群ｆ：ヒドロキシ、低級アルキルオキシ、シクロアルキル、アリール、カルボキシ、および置換されていてもよいアミノカルボニル
本明細書中、Ｒ１における「置換されていてもよいナフチル」としては、５位および８位が置換されていない２−ナフチルが好ましい。
本明細書中、Ｒ１における「置換されていてもよいカルバゾリル」としては、置換されていないカルバゾリルが好ましい。【００２４】
本発明化合物としては、特に以下のＡ）〜ＡＣ）で示される化合物が好ましい。
Ａ）一般式（ＩＶ）：
【化１６】
2007102392.tif 000018
［式中、Ｒ１１は、置換されていてもよいナフチルまたは置換されていてもよいカルバゾリル；
Ｚ１は、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）＝Ｃ（Ｒ９）−、−Ｃ≡Ｃ−、−Ｏ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｏ−、−Ｓ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｓ−、−ＳＯ−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ−、−ＳＯ２−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−ＳＯ２−、−Ｎ（Ｒ１０）−Ｃ（Ｒ８）（Ｒ９）−、−Ｃ（Ｒ８）（Ｒ９）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｎ（Ｒ１０）−、−Ｎ（Ｒ１０）−ＳＯ２−、−ＳＯ２−Ｎ（Ｒ１０）−、−Ｃ（Ｒ８）（Ｒ９）−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｃ（Ｒ８）（Ｒ９）−、または−Ｃ（＝Ｏ）Ｃ（＝Ｏ）−（式中、Ｒ８、Ｒ９およびＲ１０はそれぞれ独立して、水素原子または低級アルキル）；
Ｒ１２は、水素原子または低級アルキル；
Ｒ１３は、水素原子、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、s−ブチル、イソブチル、t−ブチル、ヒドロキシメチル、１−ヒドロキシエチル、２−ヒドロキシエチル、カルボキシメチル、カルボキシエチル、メチルオキシメチル、メチルチオメチル、２−メチルチオエチル、フェニル、４−ヒドロキシフェニル、４−フルオロフェニル、４−メチルオキシフェニル、ベンジル、４−ヒドロキシベンジル、４−フルオロベンジル、４−クロロベンジル、４−メトキシベンジル、インドール−３−イルメチル、１−カルボキシメチルインドール−３−イルメチル、チアゾール−４−イルメチル、カルボキシメチルオキシベンジル、またはシクロプロピルメチルであり、
Ｒ１４が水素原子である；または、
Ｒ１３およびＲ１４が隣接する炭素と一緒に式：
【化１７】
2007102392.tif 000019
で示される環を形成してもよい；
Ｒ１５は、ヒドロキシまたは低級アルキルオキシ；
Ｒ１６およびＲ１７はそれぞれ独立して、ハロゲン、低級アルキル、低級アルキルオキシ、またはヒドロキシ；
ｘおよびｙはそれぞれ独立して０〜３の整数］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。【００２５】
Ｂ）一般式（Ｖ）：
【化１８】
2007102392.tif 000020
［式中、Ｒ１１、Ｚ１、Ｒ１２、Ｒ１３、Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７、ｘ、およびｙは前記Ａ）と同意義］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｃ）一般式（ＶＩ）：
【化１９】
2007102392.tif 000021
［式中、Ｒ１１、Ｚ１、Ｒ１２、Ｒ１３、Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７、ｘ、およびｙは前記Ａ）と同意義］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｄ）一般式（ＶＩＩ）：
【化２０】
2007102392.tif 000022
［式中、Ｒ１１、Ｚ１、Ｒ１２、Ｒ１３、Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７、ｘ、およびｙは前記Ａ）と同意義］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｅ）一般式（ＶＩＩＩ）：
【化２１】
2007102392.tif 000023
［式中、Ｒ１１、Ｚ１、Ｒ１２、Ｒ１３、Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７、ｘ、およびｙは前記Ａ）と同意義］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。【００２６】
Ｆ）一般式（ＩＸ）：
【化２２】
2007102392.tif 000024
［式中、Ｒ１１、Ｚ１、Ｒ１２、Ｒ１３、Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７、ｘ、およびｙは前記Ａ）と同意義］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｇ）一般式（Ｘ）：
【化２３】
2007102392.tif 000025
［式中、Ｒ１１、Ｚ１、Ｒ１２、Ｒ１３、Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７、ｘ、およびｙは前記Ａ）と同意義］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｈ）一般式（ＸＩ）：
【化２４】
2007102392.tif 000026
［式中、Ｒ１１、Ｚ１、Ｒ１２、Ｒ１３、Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７、ｘ、およびｙは前記Ａ）と同意義］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｉ）一般式（ＸＩＩ）：
【化２５】
2007102392.tif 000027
［式中、Ｒ１１、Ｚ１、Ｒ１２、Ｒ１３、Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７、ｘ、およびｙは前記Ａ）と同意義］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｊ）一般式（ＸＩＩＩ）：
【化２６】
2007102392.tif 000028
［式中、Ｒ１１、Ｚ１、Ｒ１２、Ｒ１３、Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７、ｘ、およびｙは前記Ａ）と同意義］で示される化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。【００２７】
Ｋ）Ｒ１１が、置換されていてもよいナフチルである、Ａ）〜Ｊ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｌ）Ｒ１１が、式：
【化２７】
2007102392.tif 000029
（式中、Ｒ２６は水素原子、置換されていてもよい低級アルキル、置換されていてもよい低級アルケニル、ヒドロキシ、置換されていてもよい低級アルキルオキシ、カルボキシ、アシル、置換されていてもよいアミノ、置換されていてもよいアミノカルボニル、または非芳香族複素環；
Ｒ２７はハロゲン、シアノ、またはアシル；
ｎ２は０〜２の整数であり、Ｒ２７は置換可能な全ての環構成原子上で置換しうる）で示される基であるＡ）〜Ｋ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、ｎ２が０である化合物が好ましい。
Ｍ）Ｒ１１が、式：
【化２８】
2007102392.tif 000030
（式中、Ｒ２８は水素原子；カルボキシもしくは低級アルキルオキシイミノで置換されていてもよい低級アルキル；カルボキシで置換されていてもよい低級アルケニル；ヒドロキシ；シクロアルキル、ヒドロキシ、低級アルキルオキシ、カルボキシ、もしくは１ないし２の低級アルキルで置換されていてもよいアミノカルボニルで置換されていてもよい低級アルキルオキシ；カルボキシ；アシル；1ないし２のアシルもしくは低級アルキルスルホニルで置換されていてもよいアミノ；1ないし２の低級アルキルで置換されていてもよいアミノカルボニル；または非芳香族複素環；
Ｒ２９はハロゲン、シアノ、またはアシル；
ｎ３は０〜２の整数であり、Ｒ２９は置換可能な全ての環構成原子上で置換しうる）で示される基であるＡ）〜Ｌ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、ｎ３が０である化合物が好ましい。
Ｎ）Ｒ１１が、式：
【化２９】
2007102392.tif 000031
（式中Ｒ２６、Ｒ２７、およびｎ２は前記Ｌ）と同意義）で示される基であるＡ）〜Ｋ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、ｎ２が０である化合物が好ましい。
Ｏ）Ｒ１１が、式：
【化３０】
2007102392.tif 000032
（式中Ｒ２８、Ｒ２９、およびｎ３は前記Ｍ）と同意義）で示される基であるＡ）〜Ｋ）、およびＮ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、ｎ３が０である化合物が好ましい。
Ｐ）Ｒ１１が、式：
【化３１】
2007102392.tif 000033
（式中Ｒ２６、Ｒ２７、およびｎ２は前記Ｌ）と同意義）で示される基であるＡ）〜Ｋ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、ｎ２が０である化合物が好ましい。
Ｑ）Ｒ１１が、式：
【化３２】
2007102392.tif 000034
（式中Ｒ２８、Ｒ２９、およびｎ３は前記Ｍ）と同意義）で示される基であるＡ）〜Ｋ）、およびＰ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、ｎ３が０である化合物が好ましい。
Ｒ）Ｒ１１が、置換されていてもよいカルバゾリルである、Ａ）〜Ｋ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。上記化合物において、Ｒ１１が非置換のカルバゾリルである化合物が好ましい。
Ｓ）Ｚ１が、−ＣＨ２−ＣＨ２−、−ＣＨ＝ＣＨ−、−Ｃ≡Ｃ−、−Ｏ−ＣＨ２−、−ＣＨ２−Ｏ−、−Ｓ−ＣＨ２−、−ＣＨ２−Ｓ−、−ＳＯ−ＣＨ２−、−ＣＨ２−ＳＯ−、−ＳＯ２−ＣＨ２−、−ＣＨ２−ＳＯ２−、−Ｎ（Ｒ１０）−ＣＨ２−、−ＣＨ２−Ｎ（Ｒ１０）−、−ＮＨ−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−ＮＨ−、−ＣＨ２−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−ＣＨ２−、または−Ｃ（＝Ｏ）Ｃ（＝Ｏ）−である、Ａ）〜Ｒ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｔ）Ｚ１が、−ＣＨ２−ＣＨ２−、−ＣＨ＝ＣＨ−、−Ｃ≡Ｃ−、−Ｏ−ＣＨ２−、または−ＣＨ２−Ｏ−である、Ａ）〜Ｓ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｕ）Ｚ１が、−ＣＨ２−ＣＨ２−、−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−である、Ａ）〜Ｔ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｖ）Ｚ１が、−Ｃ≡Ｃ−である、Ａ）〜Ｕ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｗ）Ｒ１２が、水素原子である、Ａ）〜Ｖ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｘ）Ｒ１３が、水素原子、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、s−ブチル、イソブチル、t−ブチル、ヒドロキシメチル、１−ヒドロキシエチル、２−ヒドロキシエチル、カルボキシメチル、カルボキシエチル、メチルオキシメチル、メチルチオメチル、２−メチルチオエチル、フェニル、４−ヒドロキシフェニル、４−フルオロフェニル、４−メチルオキシフェニル、ベンジル、４−ヒドロキシベンジル、４−フルオロベンジル、４−クロロベンジル、４−メトキシベンジル、インドール−３−イルメチル、１−カルボキシメチルインドール−３−イルメチル、チアゾール−４−イルメチル、カルボキシメチルオキシベンジル、またはシクロプロピルメチルであり、Ｒ１４が水素原子であるＡ）〜Ｗ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｙ）Ｒ１３が、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、s−ブチル、イソブチル、t−ブチル、ヒドロキシメチル、１−ヒドロキシエチル、２−ヒドロキシエチル、カルボキシメチル、カルボキシエチル、メチルオキシメチル、メチルチオメチル、２−メチルチオエチル、フェニル、４−ヒドロキシフェニル、４−フルオロフェニル、４−メチルオキシフェニル、ベンジル、４−ヒドロキシベンジル、４−フルオロベンジル、４−クロロベンジル、４−メトキシベンジル、インドール−３−イルメチル、１−カルボキシメチルインドール−３−イルメチル、チアゾール−４−イルメチル、カルボキシメチルオキシベンジル、またはシクロプロピルメチルであり、Ｒ１４が水素原子である、Ａ）〜Ｘ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
Ｚ）Ｒ１３およびＲ１４が隣接する炭素と一緒に式：
【化３３】
2007102392.tif 000035
で示される環を形成する、Ａ）〜Ｗ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。【００２８】
ＡＡ）Ｒ１５が、ヒドロキシである、Ａ）〜Ｚ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
ＡＢ）式：
【化３４】
2007102392.tif 000036
で示される基が、式：
【化３５】
2007102392.tif 000037
（式中、Ｒ１８、Ｒ１９、Ｒ２０、およびＲ２１において、ｉ）すべてが水素原子であるか、ｉｉ）Ｒ１８のみが低級アルキルであり、残りはすべて水素原子であるか、ｉｉｉ）Ｒ１９のみが低級アルキルであり、残りはすべて水素原子であるか、ｉｖ）Ｒ１８およびＲ２０はそれぞれ独立して低級アルキルであり、残りはすべて水素原子であるか、ｖ）Ｒ１８およびＲ２１はそれぞれ独立して低級アルキルであり、残りはすべて水素原子であるか、またはｖｉ）Ｒ１９およびＲ２１はそれぞれ独立して低級アルキルであり、残りはすべて水素原子である）で示される基である、Ａ）、Ｆ）、およびＫ）〜ＡＡ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
ＡＣ）式：
【化３６】
2007102392.tif 000038
で示される基が、式：
【化３７】
2007102392.tif 000039
（式中、Ｒ２２は、水素原子、ハロゲン、ヒドロキシ、または低級アルキルオキシ）で示される基である、Ｂ）、Ｇ）、およびＫ）〜ＡＡ）のいずれかに記載の化合物、その光学活性体、もしくはそれらの製薬上許容される塩、またはそれらの溶媒和物。
【発明の効果】
【００２９】
ある種の新規なスルホンアミド誘導体が、ＭＭＰ−１３選択的阻害活性を示すことを見出した。これら誘導体は、ＭＭＰ−１３に起因または関連する疾患、特に変形性関節症（ＯＡ）の治療または予防剤として利用できる。また、本発明化合物は、タンパク結合率が比較的低い、溶解性に優れる、経口吸収性がよい、および／または毒性が低い等の医薬品として優れた性質を有している。
【発明を実施するための最良の形態】
【００３０】
本発明化合物は、ＷＯ９７／２７１７４、ＷＯ００／４６１８９等に記載の方法および公知の方法に従って合成することができる。以下に本発明化合物の合成方法としてＡ法およびＢ法を例示する。
（Ａ法）
【化３８】
2007102392.tif 000040
（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ６、Ｒ７、ｍ、およびｎは前記と同意義；Ｒ２３はカルボキシル基の保護基；Ｈａｌ１はハロゲン）【００３１】
（第１工程）
原料化合物の式（ｉ）で示される化合物の一部のものは市販品として入手できる。その他のものは、Tetrahedron Lett. 39(1998) 617-620に記載の方法等に従って合成することができる。
原料化合物の式（ｉｉ）で示される化合物の一部のものは市販品として入手できる。
式（ｉ）で示される化合物またはその塩と式（ｉｉ）で示される化合物を、アセトニトリル、テトラヒドロフラン、N,N-ジメチルホルムアミド等の溶媒中、トリエチルアミン、ジイソプロピルエチルアミン、炭酸カリウム等の塩基の存在下、氷冷下〜８０度、好ましくは０度〜３０度で１〜３８時間、好ましくは３〜２４時間反応させて、式（ｉｉｉ）で示される化合物を得ることができる。
（第２工程）
式（ｉｉｉ）で示される化合物を、メチルトリフルオロメタンスルホナートと氷冷下〜室温で、１〜２４時間、好ましくは１〜５時間反応させて式（ｉｖ）で示される化合物を得ることができる。
（第３工程）
原料化合物の式（ｖ）で示されるアミノ酸またはその酸付加塩（例えば、塩酸塩、p-トルエンスルホン酸塩、トリフルオロ酢酸塩）の一部のものは市販品として入手できる。その他のものは実験化学講座２２巻、第４版（日本化学会編）に記載のアミノ酸合成法、 J. Med. Chem. 38, 1689-1700 (1995) Gary M. Ksander et. al.等に従って合成できる。
また、スルホニル化試薬（例えば、スルホン酸ハロゲン化物）の一部のものは市販品として入手可能であり、その他のものは新実験化学講座１４巻、1787頁、(1978)、Synthesis 852-854 (1986) Tatsuo Hamada et. al.等に従って合成できる。
カルボキシル基の保護基としては、例えば、エステル（例えば、メチルエステル、ｔｅｒｔ−ブチルエステル、ベンジルエステル）化されたカルボキシル基が挙げられる。これらの保護基の脱離は、保護基に応じて酸（例えば、塩酸、トリフルオロ酢酸）または塩基（例えば、水酸化ナトリウム等）の存在下に加水分解するか、または接触還元（例えば、10%パラジウム-炭素触媒存在下）することによって実施される。
スルホニル化反応の溶媒としては、ジメチルホルムアミド、テトラヒドロフラン、ジオキサン、ジメチルスルホキシド、アセトニトリル、水もしくはそれら混合溶媒、または水不溶性溶媒（例えば、ベンゼン、ジクロロメタン）と上記溶媒との混合溶媒が挙げられる。
スルホニル化反応に用いられる塩基は、トリエチルアミン、Ｎ−メチルモルホリン等の有機塩基、または水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基等である。反応温度は通常、氷冷〜室温である。尚、Ｒ２およびＲ４がスルホニル化に障害となる置換基（例えば、ヒドロキシ、メルカプト、アミノ、グアニジノ）を有する基である場合には、Protective Groups in Organic Synthesis, Theodora W Green (John Wiley & Sons) 等に記載の方法で予め保護し、望ましい段階でその保護基を除去すればよい。
（第４工程）
化合物（ｖｉ）をジメチルホルムアミド、トルエン、キシレン、ベンゼン、テトラヒドロフラン等の溶媒中、パラジウム触媒（例えば、Pd(Ph3P)2Cl2等）、２価の銅試薬（例えば、CuI等）、有機塩基（例えば、トリエチルアミン、ジイソプロピルエチルアミン等）の存在下、エチニルナフタレン等のエチニル基を有する置換されていてもよいナフチル誘導体等を反応させることにより（薗頭反応）、目的とする化合物へと変換することができる。
反応温度は、室温〜１００℃、好ましくは室温〜８０℃、反応時間は、３〜３０時間、好ましくは１０〜２０時間である。置換されていてもよいナフチル誘導体が本反応の障害となる置換基を有する場合には、Protective Groups in Organic Synthesis, Theodora W Green (John Wiley & Sons) 等に記載の方法で予め保護し、望ましい段階でその保護基を除去すればよい。
（第５工程）
化合物（ｖｉｉ）を、ジメチルホルムアミド、テトラヒドロフラン、ジオキサン等の溶媒中、氷冷下〜８０℃、好ましくは氷冷下〜室温でハロゲン化アルキル（例えば、ヨウ化メチル、ヨウ化エチル等）やハロゲン化アラルキル（例えば、ベンジルクロリド、ベンジルブロミド等）等を加え、３〜３０時間、好ましくは１０〜２０時間攪拌することにより目的のＮ−Ｒ２体を得ることができる。
（第６工程）
化合物（ｖｉｉｉ）の保護基を、常法に従って脱保護することにより、一般式（Ｉ）で表される化合物を合成することができる。【００３２】
（Ｂ法）
【化３９】
2007102392.tif 000041
（式中、Ｒ１、Ｒ３、Ｒ４、Ｒ６、Ｒ７、Ｒ２３、ｍ、およびｎは前記と同意義；Ｒ１０はカルボキシル基の保護基；Ｈａｌ１およびＨａｌ２はそれぞれ独立してハロゲン；ＰｒｏはＢｏｃ等の保護基）【００３３】
（第１工程）
原料化合物の式（ｘ）で示される化合物の一部のものは市販品として入手できる。
原料化合物の式（ｘｉ）で示される化合物の一部のものは市販品として入手できる。その他のものは、Tetrahedron Lett. 37(1996) 6965-6968に記載の方法等に従って合成することができる。
式（ｘ）で示される化合物またはその塩と式（ｘｉ）で示される化合物を、ジメチルホルムアミド、1,4-ジオキサン、ジクロロメタン等の溶媒中、炭酸カリウム、炭酸セシウム、水酸化ナトリウム等の塩基の存在下、氷冷下〜１１０度、好ましくは０度〜８０度で１〜３６時間、好ましくは１〜２４時間反応させて、式（ｘｉｉ）で示される化合物を得ることができる。
（第２工程）
原料化合物の式（ｘｉｉｉ）で示される化合物の一部のものは市販品として入手できる。その他のものは、Angew Chem, Int Ed 37(1998) 325-329.に記載の方法等に従って合成することができる。
式（ｘｉｉ）で示される化合物と式（xiii）で示される化合物を、トルエン−N−メチルピペリドン、N,N-ジメチルホルムアミド、1,4-ジオキサン等の混合溶媒中、t−ブトキシナトリウム、炭酸セシウム等の塩基、酢酸パラジウム等のパラジウム触媒、およびトリ-t-ブチルホスフィン、トリフェニルホスフィン等のリガンドと室温〜１５０度、好ましくは室温〜１２０度で、１〜２４時間、好ましくは１〜８時間反応させて式（ｘｉｖ）で示される化合物を得ることができる。
（第３工程）
保護基を脱保護する工程である。通常行われる方法によって行うことができる。
（第４工程）
Ａ法第１工程と同様の方法で行うことができる。
（第５工程）
Ａ法第２工程と同様の方法で行うことができる。
（第６工程）
Ａ法第３工程と同様の方法で行うことができる。
（第７工程）
Ａ法第６工程と同様の方法で行うことができる。
一般式（ＩＩＩ）で示される化合物も上記の方法、ＷＯ９７／２７１７４、ＷＯ００／４６１８９等に記載の方法および公知の方法に従って合成することができる。【００３４】
変形性関節症およびアジュバント関節炎についての本発明化合物の治療効果は、以下に示す方法によって効果を確認することができる。
Ａ）変形性関節症
１２週齢の雌性Hartley系モルモット（日本チャールズリバー）を用いて、Meacockらの方法（J. Exp. Path. 71: 279-293, 1990）に従い右側膝関節半月板および内側側副靭帯切除を行い、モルモット変形性膝関節症モデルを作製する。手術翌日から溶媒0.5%メチルセルロース溶液、あるいは30mg/kgの被験化合物溶液を1日1回、１０日間連日経口投与する。
投与最終日の翌日、右側大腿骨遠位部および脛骨近位部を採取する。関節軟骨表面をｉｎｄｉａ  ｉｎｋ（呉竹社製）で染色した後、軟骨表面をデジタルカメラ（ニコン社製）で撮影する。化合物の評価は、撮影画像を用いて関節軟骨表面のOA病変の程度を盲検法でスコア化して行う。
また同様にして、１２週齢の雌性ＮＺＷ系ウサギ（北山ラベス）または１２週齢の雌性ＳＤ系ラット（日本クレア）を用いて6週間連日経口投与することによっても、確認することができる。【００３５】
Ｂ）アジュバント関節炎
７週齢の雌性Lewisラット（日本チャールズリバー社製）を用いて、Fletcherらの方法（J. Pharmacol. Exp. Ther. 284(2): 714-721）に従い牛酪死菌を右後肢足蹠へ投与しラットアジュバント関節炎モデルを作製する。投与翌日から溶媒である0.5%メチルセルロース溶液、あるいは30mg/kgの被験化合物溶液を1日1回経口投与する。投与21日後、後肢腫脹の程度を体積記録計（塩野義社製）を用いて測定した後、脾臓および胸腺を採取し重量を測定する。また、両後肢のX線撮影（OHMIC社製）を行う。X線像の判定は関節破壊の程度により0（正常）から３（骨・軟骨完全破壊）までのスコアで盲検法により行う。【００３６】
本明細書中、「溶媒和物」とは、例えば有機溶媒との溶媒和物、水和物等を包含する。水和物を形成する時は、任意の数の水分子と配位していてもよい。
「本発明化合物」という場合には、製薬上許容される塩、またはその溶媒和物も包含される。例えば、アルカリ金属（リチウム、ナトリウム、カリウム等）、アルカリ土類金属（マグネシウム、カルシウム等）、アンモニウム、有機塩基およびアミノ酸との塩、または無機酸（塩酸、臭化水素酸、リン酸、硫酸等）、および有機酸（酢酸、クエン酸、マレイン酸、フマル酸、ベンゼンスルホン酸、ｐ−トルエンスルホン酸等）との塩が挙げられる。これらの塩は、通常行われる方法によって形成させることができる。
また、本発明化合物は特定の異性体に限定するものではなく、全ての可能な異性体（例えば、光学活性体）やラセミ体を含むものである。
本発明化合物は後述する試験例の記載の通り、ＭＭＰ−２およびＭＭＰ−９には阻害活性を示さず、選択的にかつ優れたＭＭＰ−１３阻害活性を示す。
本発明化合物は、変形性関節症、関節リウマチ、アジュバント関節炎、歯周炎、肝硬変、骨粗鬆症、骨吸収、歯肉炎、大腸直腸癌、扁平上皮癌、上皮細胞癌、前立腺癌、卵巣癌、舌癌、子宮内膜癌、胃癌の治療剤として使用することができる。
本発明化合物を、上記の疾患の治療を目的としてヒトに投与する場合は、散剤、顆粒剤、錠剤、カプセル剤、丸剤、液剤等として経口的に、または注射剤、坐剤、経皮吸収剤、吸入剤等として非経口的に投与することができる。また、本化合物の有効量にその剤型に適した賦形剤、結合剤、湿潤剤、崩壊剤、滑沢剤等の医薬用添加剤を必要に応じて混合し、医薬製剤とすることができる。注射剤の場合には、適当な担体と共に滅菌処理を行って製剤とする。
投与量は疾患の状態、投与ルート、患者の年齢、または体重によっても異なるが、成人に経口で投与する場合、通常０．１〜１００mg／kg／日であり、好ましくは１〜２０mg／kg／日である。
以下に実施例および試験例を挙げて本発明をさらに詳しく説明するが、本発明はこれらにより限定されるものではない。
実施例【００３７】
実施例中、以下の略号を使用する。
Ｍｅ：メチル
Ｔｆ：トリフルオロメタンスルホニル
Ｂｏｃ：ｔ−ブトキシカルボニル
【実施例１】
【００３８】
(S)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-ペンタン酸（I-1）の合成
【化４０】
2007102392.tif 000042
【００３９】
第１工程
1−（4−ブロモフェニル）ピペラジン塩酸塩（1）（5g、18.0 mmol）とトリエチルアミン（2.8 mL、20.1 mmol）のアセトニトリル（80mL）溶液に3−（イミダゾール−１−スルホニル）−１−メチル−３Ｈ−イミダゾール−１−イウムトリフレート（2：J. Org. Chem., 68, 115(2003) ） (9.8g、27.0 mmol) を加え、室温で24時間攪拌した。反応液を氷水に注ぎ、酢酸エチルで抽出し、有機層を水洗した。無水硫酸ナトリウムにて乾燥後、減圧濃縮し、残渣をシリカゲルクロマトグラフィーに付し、ヘキサン／酢酸エチル ＝1／1にて溶出する部分を集め、淡茶色の化合物（3）（2.91g、収率43.5%）を得た。化合物（3）は精製することなく次工程に用いた。融点153−154℃
1H NMR (CDCl3) δ: 3.20-3.26 (m, 4H), 3.36-3.40 (m, 4H), 6.76 (d, J = 9.0 Hz, 2H), 7.22 (m, 1H), 7.29 (m, 1H), 7.37 (d, J = 9.0 Hz, 2H), 8.07 (m, 1H).【００４０】
第２工程
化合物（3）（4.82g、13.0 mmol）のジクロロメタン（80 mL）溶液に、メチルトリフルオロメタンスルホナート（1.6 mL、14.1 mmol）を氷冷下に加え、そのまま2.5時間撹拌した。析出した固体を濾取し、ジクロロメタン、次いで nーヘキサンで洗浄し、風乾後、化合物（4）（6.3g、収率90.6%）を得た。化合物（4）は精製することなく次工程に用いた。融点154−156℃
1H-NMR (DMSO-d6) δ: 3.28-3.35 (m, 4H), 3.46-3.53 (m, 4H), 3.88 (s, 3H), 6.93 (d, J = 9.0 Hz, 2H), 7.38 (d, J = 9.0 Hz, 2H), 7.98 (m, 1H), 8.24 (m, 1H), 9.85 (s, 1H).【００４１】
第３工程
化合物（4）（0.8g、1.49 mmol）のアセトニトリル（8 mL）溶液に、室温で L−ノルバリンメチルエステル塩酸塩（5）（0.38g、2.27mmol)、次いでトリエチルアミン（0.31ｍL、2.22mmol）を加え40時間撹拌した。反応液を氷水に注ぎ、酢酸エチルで抽出した。有機層を水洗し、無水硫酸ナトリウムにて乾燥後、減圧濃縮した。残渣をシリカゲルクロマトグラフィーに付し、酢酸エチル／ヘキサン＝1／3にて溶出する部分を集め、淡黄色の化合物（6）（0.35g、収率53.8%）を得た。化合物（6）は精製することなく次工程に用いた。
1H NMR (CDCl3) δ: 0.95 (t, J = 7.2 Hz, 3H), 1.35-1.50 (m, 2H), 1.60-1.85 (m, 2H), 3.13-3.22 (m, 4H), 3.32-3.40 (m, 4H), 3.77 (s, 3H), 3.98 (m, 1H), 4.91 (d, J = 9.6 Hz, 1H), 6.82 (d, J = 9.0 Hz, 2H), 7.37 (d, J = 9.0 Hz, 2H).【００４２】
第4工程
化合物（6）（0.34g、0.78 mmol）のジメチルホルムアミド（5 mL）溶液に、2−エチニル−６−メトキシナフタレン（7）（0.19g、1.04ｍmol）を加え窒素ガス雰囲気下にて脱気した。次いで、ビス(トリフェニルホスフィン)パラジウム（II）クロリド（0.06g、0.08mmol）、ヨウ化銅（I）（0.03g、0.16 mmol）、トリエチルアミン（0.63 ml, 4.50 mmol）を加え、再度窒素ガス雰囲気下にて脱気し、90 ℃で14時間加熱攪拌した。反応液を氷水−2mol/L塩酸に注ぎ、酢酸エチルで抽出した。有機層を飽和炭酸水素ナトリウム水溶液、飽和塩化ナトリウム水溶液で順次洗浄し、無水硫酸ナトリウムにて乾燥後、減圧濃縮した。残渣をシリカゲルクロマトグラフィーに付し、酢酸エチル／n−ヘキサン／クロロホルム＝1／2／1にて溶出する部分を集め、酢酸エチル／n−ヘキサン＝1／３にて結晶化させ淡茶色の化合物（8）（0.09g、収率21.0%）を得た。融点174−176℃
1H NMR (CDCl3) δ: 0.96 (t, J = 7.5 Hz, 3H), 1.35-1.52 (m, 2H), 1.60-1.85 (m, 2H), 3.23-3.40 (m, 8H), 3.77 (s, 3H), 3.93 (s, 3H), 3.99 (m, 1H), 4.92 (d, J = 9.6 Hz, 1H), 6.90 (d, J = 9.0 Hz, 2H), 7.11 (d, J = 2.7 Hz, 1H), 7.16 (dd, J = 2.4, 9.0 Hz, 1H), 7.48 (d, J = 8.7 Hz, 2H), 7.53 (dd, J = 1.8, 8.7 Hz, 1H), 7.69 (d, J = 8.4 Hz, 1H), 7.70 (d, J = 9.0 Hz, 1H), 7.95 (s, 1H).【００４３】
第５工程
化合物（8）（0.08g、0.15 mmol）のジメチルスルホキシド（0.9 mL）溶液に、室温で 1 mol/L水酸化ナトリウム水溶液（0.9 mL）を加え、60℃で14時間加熱撹拌した。反応液を氷水−5%クエン酸水溶液に注ぎ、酢酸エチルで抽出した。有機層を水洗し、無水硫酸ナトリウムにて乾燥後、減圧濃縮した。残渣をアセトン／n−ヘキサンから再結晶することにより、(S)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-ペンタン酸（I-1）（0.07g、収率90.0%）を得た。融点 187−190℃（分解）
1H-NMR (DMSO-d6) δ: 0.88 (t, J = 7.5 Hz, 3H), 1.30-1.50 (m, 2H), 1.50-1.65 (m, 2H), 3.05-3.45 (m, 8H), 3.69 (m, 1H), 3.89 (s, 3H), 7.00 (d, J = 9.0 Hz, 2H), 7.21 (dd, J = 2.7, 9.0 Hz, 1H), 7.35 (d, J = 2.7 Hz, 1H), 7.43 (d, J = 8.7 Hz, 2H), 7.52 (dd, J = 1.5, 8.4 Hz, 1H), 7.82 (d, J = 8.4 Hz, 1H), 7.85 (d, J = 9.0 Hz, 1H), 7.91 (d, J = 9.0 Hz, 1H), 8.04 (s, 1H), 12.78 (br s, 1H).【００４４】
(R)-2-{4-[4-(ナフタレン-2-イルメトキシ)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-2）の合成
【化４１】
2007102392.tif 000043
【００４５】
第１工程
p-ヨードフェノール (9)（10.0 g, 45.6 mmol）と炭酸カリウム（9.42 g, 68.2 mmol）のジメチルホルムアミド（100 mL）の混合溶液をよく脱気して窒素ガス置換した。次いで、2‐ブロモメチルナフタレン (10)（11.1 mg, 50.0mmol）を加え、70℃で1時間攪拌した。反応液を室温まで冷却し、氷−2mol/L塩酸に注ぎ5分間攪拌した。析出した結晶を濾取し、水洗浄することにより化合物 (3)（7.6 g, 収率 46%）を得た。母液から酢酸エチルで抽出し、有機層を水、飽和塩化ナトリウム水溶液で順次洗浄し、無水硫酸ナトリウムにて乾燥後、減圧濃縮した。残渣をテトラヒドロフラン／水にて結晶化することにより、化合物 (11)（8.6g, 収率 53%）を得た。 (総収量 16.2 g, 総収率 99%)  融点 136-137 ℃
1H NMR (CDCl3) δ: 5.20 (s, 2H), 6.80 (dd, J = 2.1 Hz, 9.0 Hz, 2H), 7.48-7.59 (m, 5H), 7.82-7.88 (m, 4H).【００４６】
第２工程
化合物 (11)（3.5 g, 9.7 mmol）、1-t-ブトキシカルボニルピペラジン (12)（10.9 g, 58.3 mmol）およびt-ブトキシドナトリウム（13.1 g, 13.6 mmol）のトルエン（70 mL）溶液とN−メチルピペリドン（7 mL）の混合溶液を、よく脱気し窒素ガス置換した。次いで、酢酸パラジウム（0.11 g, 0.49 mmol）とトリ-t-ブチルホスフィン（0.47 ml, 1.94 mmol）を加え、再度よく窒素ガス置換し、120度で5時間攪拌した。反応液をセライトでろ過し、濾液に水を加え酢酸エチルで抽出した。有機層を飽和塩化ナトリウム水溶液で洗浄し、無水硫酸ナトリウムにて乾燥後、減圧濃縮した。残渣をシリカゲルクロマトグラフィーに付し、酢酸エチル／n-ヘキサン = 2 ／ 3にて溶出する部分を集め減圧濃縮することにより、化合物 (13) を得た。（2.6 g, 収率 64%）融点 147-149 ℃
1H NMR (CDCl3) δ: 1.48 (s, 9H), 3.01 (bs, 4H), 3.57 (bs, 4H), 5.19 (s, 2H), 6.91-6.98 (m, 4H), 7.26-7.55 (m, 3H), 7.82-7.88 (m, 4H).【００４７】
第３工程
化合物 (13) に4mol/L塩酸酢酸エチル溶液（50 mL）を加え、室温で30分間攪拌した。反応液を減圧濃縮し、残渣をメタノールに溶解後、再び減圧濃縮した。残渣を酢酸エチルで洗浄後濾取することにより、化合物 (14) を得た。（2.4 g, 99%）融点 200-201 ℃
1H NMR (DMSO-d6) δ: 3.24 (bs, 8H), 5.22 (s, 2H), 4.98 (s, 4H), 7.51-7.57 (m, 3H), 7.90-7.96 (m, 4H), 9.13 (bs, 2H).【００４８】
第４工程
化合物 (14) および化合物（2）を用い、実施例1の第1工程に準じて反応を行い、化合物（15）を得た。
1H NMR (CDCl3) δ: 3.15 (t, J = 4.8 Hz, 4H), 3.38 (t, J = 4.8 Hz, 4H), 5.19 (s, 2H), 6.88-6.97 (m, 4H), 7.18 (bs, 1H), 7.27 (bs, 1H), 7.47-7.53 (m, 3H), 7.82-7.87 (m, 5H), 7.95 (s, 1H).【００４９】
第５工程
化合物 (15) を用い、実施例1の第2工程に準じて反応を行い、化合物（16）を得た。
1H NMR (DMSO-d6) δ: 3.16 (bs, 4H), 3.51 (bs, 4H), 3.89 (s, 3H), 5.21 (s, 2H), 6.90-6.93 (m, 4H), 7.50-7.54 (m, 3H), 7.90-7.99 (m, 5H), 8.23 (t, J = 1.8 Hz, 1H), 9.85 (s, 1H).【００５０】
第６工程
化合物（16）および化合物 (17) を用い、実施例1の第3工程に準じて反応を行い、化合物（18）を得た。
1H NMR (DMSO-d6) δ: 1.30 (d, J = 6.8 Hz, 2H), 3.04 (bs, 4H), 3.14 (bs, 4H), 3.65 (s, 3H), 3.83-3.95 (m, 1H), 5.21 (s, 2H), 6.90-6.97 (m, 4H), 7.51-7.57 (m, 3H), 7.91-7.99 (m, 4H), 8.03 (d, J = 8.8 Hz, 1H).【００５１】
第７工程
化合物 (18) を用い、実施例1の第5工程に準じて反応を行い、(R)-2-{4-[4-(ナフタレン-2-イルメトキシ)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-2）を得た。融点 167-171℃
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2Hz, 3H), 3.01 (bs, 4H), 3.14 (bs, 4H), 3.81 (t, J=7.2Hz, 1H), 5.21 (s, 2H), 6.91-6.98 (m, 4H), 7.51-7.57 (m, 3H), 7.86-7.95 (m, 5H), 12.69 (bs, 1H).【００５２】
前記と同様にして以下の化合物を合成した。
(S) -2-{4-[4-(ナフタレン-2-イルメトキシ)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-3）の合成
1H NMR (DMSO-d6) δ: 1.29 (d, J=4.8Hz, 3H), 3.05 (bs, 4H), 3.14 (bs, 4H), 5.21 (s, 2H), 6.92-6.95 (m, 4H), 7.51-7.60 (m, 3H), 7.85-7.95 (m, 5H) 【００５３】
(R)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-3-メチル-ブタン酸（I-4）の合成
1H NMR (DMSO-d6) δ: 0.80-0.97 (m, 6H), 1.98 (m, 1H), 3.00-3.60 (m, 9H), 3.89 (s, 3H), 7.00 (d, J=8.7 Hz, 2H), 7.21 (m, 1H), 7.35 (m, 1H), 7.43 (d, J = 8.7 Hz, 2H), 7.52 (m, 1H), 7.68-7.90 (m, 3H), 8.04 (s, 1H)【００５４】
(S)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-3-メチル-ブタン酸（I-5）の合成
1H NMR (DMSO-d6) δ: 0.91 (d, J=6.6 Hz, 3H),  0.93 (d, J=6.6 Hz, 3H), 1.98 (m, 1H),  3.05-3.35 (m, 8H), 3.50 (m, 1H), 3.89 (s, 3H), 7.00 (d, J=9.0 Hz, 2H), 7.21 (dd, J=2.4, 9.0 Hz, 1H), 7.35 (m, 1H), 7.43 (d, J = 9.3 Hz, 2H), 7.52 (m, 1H), 7.78-7.90 (m, 3H), 8.03 (s, 1H), 12.74 (br s, 1H)【００５５】
(S)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-ヘキサン酸（I-6）の合成
1H NMR (DMSO-d6) δ: 0.86 (t, J=7.2 Hz, 3H), 1.20-1.44 (m, 4H), 1.50-1.72 (m, 2H), 3.05-3.35 (m, 8H), 3.66 (m, 1H), 3.88 (s, 3H), 6.99 (d, J=9.0 Hz, 2H), 7.20 (dd, J=2.4, 9.0 Hz, 1H), 7.34 (d, J=2.7 Hz, 1H), 7.42 (d, J=8.7 Hz, 2H), 7.51 (dd, J=1.8, 8.4 Hz, 1H), 7.81 (d, J=8.7 Hz, 1H), 7.84 (d, J=9.3 Hz, 1H), 7.90 (d, J=8.1 Hz, 1H), 8.02 (s, 1H), 12.76 (br s, 1H)【００５６】
(R)-2-{4-[4-(ナフタレン-2-イルオキシメチル)- フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-7）の合成
1H-NMR (DMSO-d6) δ: 1.30 (d, J=8.8Hz, 3H), 3.17-3.20 (m, 8H), 3.80 (bs, 1H), 5.10 (s, 2H), 6.99 (d, J=7.7Hz, 2H), 7.20 (d, J=9.6Hz, 1H), 7.34-47 (m, 5H), 7.78-7.83 (4H, m)【００５７】
(R)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-8）の合成
1H-NMR (DMSO-d6) δ: 1.30 (d, J=6.9 Hz, 3H), 3.05-3.40 (m, 8H), 3.80 (m, 1H), 3.88 (s, 3H), 6.99 (d, J=8.7 Hz, 2H), 7.20 (dd, J=2.4, 9.0 Hz, 1H), 7.34 (d, J=2.1 Hz, 1H), 7.42 (d, J=8.7 Hz, 2H), 7.51 (dd, J=1.5, 8.1 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.83 (d, J=9.0 Hz, 1H), 7.91 (d, J=8.1 Hz, 1H), 8.02 (s, 1H), 12.72 (br s, 1H)【００５８】
(S)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-4-メチル-ペンタン酸（I-9）の合成
1H-NMR (DMSO-d6) δ: 0.89 (d, J=6.3 Hz, 3H), 0.90 (d, J=6.6 Hz, 3H), 1.35-1.60 (m, 2H), 1.74 (m, 1H), 3.05-3.40 (m, 8H), 3.70 (m, 1H), 3.89 (s, 3H), 7.00 (d, J=9.0 Hz, 2H), 7.20 (dd, J=2.4, 9.0 Hz, 1H), 7.35 (d, J=3.0 Hz, 1H), 7.43 (d, J=9.0 Hz, 2H), 7.52 (m, 1H), 7.82 (d, J=8.7 Hz, 1H), 7.84 (d, J=9.0 Hz, 1H), 7.95 (d, J=8.1 Hz, 1H), 8.03 (s, 1H), 12.76 (br s, 1H)【００５９】
(R)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-3,6-ジヒドロ-2H-ピリジン-1-スルホニルアミノ}-プロピオン酸（I-10）の合成
1H-NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 2.50-2.60 (m, 2H), 3.20-3.30 (m, 2H), 3.70-3.90 (m, 3H),  3.90 (s, 3H), 6.32 (m, 1H), 7.22 (dd, J=2.4, 8.7 Hz, 1H), 7.37 (d, J=2.4 Hz, 1H), 7.50-7.60 (m, 5H), 7.80-7.95 (m, 3H), 8.10 (s, 1H), 12.71 (br s, 1H)【００６０】
(R)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペリジン-1-スルホニルアミノ}-プロピオン酸（I-11）の合成
1H-NMR (DMSO-d6) δ: 1.31 (d, J=7.2 Hz, 3H), 1.55-1.75 (m, 2H), 1.75-1.92 (m, 2H), 2.60-2.80 (m, 3H), 3.58-3.70 (m, 2H), 3.79 (m, 1H), 3.90 (s, 3H), 7.22 (dd, J=2.7, 9.3 Hz, 1H), 7.32 (d, J=8.4 Hz, 1H), 7.37 (d, J=2.4 Hz, 2H), 7.52 (d, J=8.4 Hz, 1H), 7.56 (m, 1H), 7.77 (d, J=7.8 Hz, 1H), 7.85 (d, J=8.4 Hz, 1H), 7.87 (d, J=9.3 Hz, 1H), 8.09 (s, 1H), 12.75 (br s, 1H)【００６１】
(R)-2-{4-ヒドロキシ-4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]- ピペリジン-1-スルホニルアミノ}-プロピオン酸（I-12）の合成
1H-NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 1.60-1.75 (m, 2H), 1.85-2.02 (m, 2H), 2.95-3.15 (m, 2H), 3.30-3.50 (m, 2H), 3.79 (m, 1H), 3.89 (s, 3H), 5.18 (s, 1H), 7.21 (dd, J=2.7, 8.7 Hz, 1H), 7.36 (d, J=2.4 Hz, 1H), 7.48-7.58 (m, 5H), 7.74 (d, J=7.2 Hz, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.86 (d, J=8.7 Hz, 1H), 8.08 (s, 1H), 12.69 (br s, 1H)【００６２】
(S)-2-{4-[4-((E)-2-ナフタレン-2-イル-ビニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-ペンタン酸（I-13）の合成
1H-NMR (DMSO-d6) δ: 0.89 (t, J=6.8 Hz, 3H), 1.32-1.44 (m, 2H), 1.54-1.63 (m, 2H), 3.16-3.33 (m, 8H), 3.66-3.74 (m, 1H), 7.00 (d, J=7.2 Hz, 2H), 7.23 (d, J=16.8 Hz, 1H), 7.32 (d, J=16.8 Hz, 1H), 7.43-7.54 (m, 4H), 7.82-7.88 (m, 5H), 7.94(s, 1H), 12.70 (br s, 1H)【００６３】
(S)-2-{4-[4-(2-ナフタレン-2-イル-エチル)-フェニル]-ピペラジン-1-スルホニルアミノ}-ペンタン酸（I-14）の合成
1H-NMR (DMSO-d6) δ: 0.88 (t, J=6.8 Hz, 3H), 1.32-1.44 (m, 2H), 1.54-1.63 (m, 2H), 2.87-2.91 (m, 2H), 2.96-3.02 (m, 2H), 3.11 (s, 4H), 3.32 (s, 4H), 3.63-3.71 (m, 1H), 6.86 (d, J=7.2 Hz, 2H), 7.11 (d, J=7.2 Hz, 2H), 7.41-7.48 (m, 3H), 7.70 (s, 1H), 7.81-7.86 (m, 4H), 12.70 (br s, 1H)【００６４】
(S)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルメトキシ)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-15）の合成
1H-NMR (DMSO-d6) δ: 1.20 (d, J = 6.3 Hz, 3H), 3.03 (bs, 4H), 3.16 (bs, 4H), 3.88 (s, 3H), 5.14 (s, 2H), 6.89-6.93 (m, 4H), 7.17 (d, J = 8.8 Hz, 1H), 7.32 (s, 1H), 7.51 (d, J = 8.3 Hz, 1H), 7.85 (d, J = 8.8 Hz, 2H), 7.92 (s, 1H).【００６５】
(R)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルメトキシ)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-16）の合成
1H-NMR (DMSO-d6) δ: 1.20 (d, J = 6.3 Hz, 3H), 3.03 (bs, 4H), 3.16 (bs, 4H), 3.88 (s, 3H), 5.14 (s, 2H), 6.93 (d, J = 7.3 Hz, 4H), 7.17 (d, J = 8.8 Hz, 1H), 7.32 (s, 1H), 7.51 (d, J = 8.3 Hz, 1H), 7.83 (d, J = 8.8 Hz, 2H), 7.87 (s, 1H).【００６６】
(S)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペリジン-1-スルホニルアミノ}-ペンタン酸（I-17）の合成
1H-NMR (DMSO-d6) δ: 0.90 (d, J=7.2 Hz, 3H), 1.30-1.74 (m, 6H), 1.74-1.92 (m, 2H), 2.56-2.80 (m, 3H), 3.58-3.73 (m, 3H), 3.89 (s, 3H), 7.22 (dd, J=2.4, 8.7 Hz, 1H), 7.32 (d, J=8.4 Hz, 1H), 7.37 (d, J=2.1 Hz, 2H), 7.49-7.58 (m, 3H), 7.77 (d, J=9.0 Hz, 1H), 7.85 (d, J=8.4 Hz, 1H), 7.87 (d, J=8.7 Hz, 1H), 8.09 (s, 1H), 12.73 (br s, 1H).【００６７】
(R)-2-{4-フルオロ-4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペリジン-1-スルホニルアミノ}-プロピオン酸（I-18）の合成
1H-NMR (DMSO-d6) δ: 1.31 (d, J=6.9 Hz, 3H), 1.90-2.30 (m, 4H), 2.85-3.05 (m, 2H), 3.50-3.63 (m, 2H), 3.83 (m, 1H), 3.89 (s, 3H), 7.22 (dd, J=2.4, 9.0 Hz, 1H), 7.36 (d, J=2.4 Hz, 1H), 7.49 (d, J=8.4 Hz, 2H), 7.56 (m, 1H), 7.61 (d, J=8.4 Hz, 1H), 7.80-7.95 (m, 3H), 8.10 (s, 1H), 12.83 (br s, 1H).【００６８】
(R)-2-{4-[4-(6-メトキシ-ナフタレン-2-イルメトキシ)-フェニル]-ピペリジン-1-スルホニルアミノ}-プロピオン酸（I-19）の合成
1H-NMR (DMSO-d6) δ: 1.30 (d, J = 7.2 Hz, 2H), 1.57 (t, J = 8.8Hz, 2H), 1.78 (t, J = 11.2 Hz, 2H), 2.62-2.73 (m, 2H), 3.60 (bs, 2H), 3.79 (t, J = 7.2 Hz1H), 3.88 (s, 3H), 5.19 (s, 2H), 6.98 (d, J = 8.6 Hz, 2H), 7.16 (t, J = 7.1 Hz, 3H), 7.32 (s, 1H), 7.52 (d, J = 9.1 Hz, 1H), 7.71 (d, J = 9.1 Hz, 1H), 7.83 (d, J = 8.8 Hz, 2H), 7.89 (s, 1H).【００６９】
(S)-2-(4-{4-[2-(6-メトキシ-ナフタレン-2-イル)-エチル]-フェニル}-ピペリジン-1-スルホニルアミノ)-ペンタン酸（I-20）の合成
1H NMR (DMSO-d6) δ: 0.90 (d, J = 6.6 Hz, 3H), 1.38-1.40 (m, 2H), 1.58-1.61 (m, 4H), 1.75-1.79 (m, 2H), 2.65-2.72 (m, 2H), 2.95 (d, J = 12.1 Hz, 4H), 3.61-3.63 (m, 3H), 3.83 (s, 3H), 7.14-7.17 (m, 5H), 7.27 (s, 1H), 7.38 (d, J = 6.6 Hz, 1H), 7.63 (s, 1H), 7.71 (t, J = 9.7 Hz, 3H).【００７０】
(S)-2-(4-{4-[(E)-2-(6-メトキシ-ナフタレン-2-イル)-ビニル]-フェニル}-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-21）の合成
1H NMR (DMSO-d6) δ: 1.27 (d, J = 6.8 Hz, 3H), 3.38-3.28 (m, 8H), 3.65 (bs, 1H), 3.86 (s, 3H), 6.98 (d, J = 8.4 Hz, 2H), 7.14-7.16 (m, 1H), 7.20 (d, J=9.6 Hz, 2H), 7.14-7.16 (m, 1H), 7.20 (d, J=9.6 Hz, 2H), 7.29(s, 1H), 7.50 (d, J = 8.4 Hz, 2H), 7.73-7.80(m, 3H), 7.87 (s, 1H).【００７１】
(S)-2-(4-{4-[2-(6-メトキシ-ナフタレン-2-イル)-エチル]-フェニル}-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-22）の合成
1H NMR (DMSO-d6) δ: 1.29 (d, J = 7.6 Hz, 3H), 2.86-2.91 (m, 2H), 2.93-2.95 (m, 2H), 3.12 (bs, 8H), 3.80-3.82 (bs, 1H), 3.85 (s, 3H), 6.86 (d, J = 8.4 Hz, 2H), 7.09 (bs, 3H), 7.26 (s, 1H), 7.35 (d, J=7.2 Hz, 1H), 7.61 (s, 1H), 7.72 (d, J = 9.2Hz, 2H), 7.83-7.84(m, 1H).【００７２】
(R)-2-{4-メトキシ-4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペリジン-1-スルホニルアミノ)-プロピオン酸（I-23）の合成
1H NMR (DMSO-d6) δ: 1.29 (d, J=6.9 Hz, 3H), 1.80-2.15 (m, 4H), 2.91 (s, 3H), 2.90-3.05 (m, 2H), 3.78 (m, 1H), 3.90 (s, 3H), 7.23 (dd, J=2.7, 9.3 Hz, 1H), 7.38 (d, J=2.4 Hz, 1H), 7.46 (d, J=8.4 Hz, 2H), 7.56 (dd, J=1.8, 8.7 Hz, 1H), 7.60 (d, J=8.4 Hz, 2H), 7.79 (m, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.88 (d, J=8.7 Hz, 1H), 8.11 (s, 1H)【００７３】
(S)-2-(4-{4-[(E)-2-(6-メトキシ-ナフタレン-2-イル)-ビニル]-フェニル}-ピペリジン-1-スルホニルアミノ)-ペンタン酸（I-24）の合成
1H NMR (DMSO-d6) δ: 0.88 (t, J=7.2 Hz, 3H), 1.38 (t, J = 7.2 Hz, 2H), 1.58-1.62 (m, 4H), 2.64-2.76 (m, 3H), 3.61-3.64 (m, 2H),  3.69 (s, 3H), 3.77-3.81 (m, 1H), 7.27 (d, J = 8.0 Hz, 2H), 7.38 (s, 2H), 7.47-7.52 (m, 2H), 7.59 (d, J=6.8 Hz, 2H), 7.85-7.92 (m, 4H), 8.00(bs, 1H).【００７４】
(S)-2-{4-[4-((E)-2-ナフタレン-2-イル-ビニル)-フェニル]-ピペリジン-1-スルホニルアミノ)-ペンタン酸（I-25）の合成
1H NMR (DMSO-d6) δ: 0.90 (d, J=7.6 Hz, 3H), 1.36-1.40 (m, 2H), 1.58-1.68 (m, 4H), 1.81-1.84 (m, 2H), 2.64-2.74 (m, 3H), 3.64-3.66 (m, 2H),  7.27 (bs, 2H), 7.38 (d, J=4.4 Hz, 2H), 7.46-7.50 (m, 2H), 7.56-7.60 (m, 2H), 7.69-7.72 (m, 1H), 7.86-7.89 (m,4H), 7.99-8.01 (m, 1H).【００７５】
(R)-2-{4-[4-((E)-2-ナフタレン-2-イル-ビニル)-フェニル]-ピペリジン-1-スルホニルアミノ)-プロピオン酸（I-26）の合成
1H NMR (DMSO-d6) δ: 1.31 (d, J=6.8 Hz, 3H), 1.59-1.66 (m, 2H), 1.84-1.87 (m, 2H), 2.57-2.77 (m, 4H), 3.65 (bs, 2H),  3.79 (bs, 1H), 7.28 (d, J=7.2Hz, 2H), 7.38 (s, 2H), 7.49-7.51 (m, 2H), 7.68-7.72 (m, 1H), 7.85-7.90 (m, 4H), 7.99 (bs, 1H).【００７６】
(R)-2-{4-[4-(6-エトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-27）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 1.40 (t, J=6.9 Hz, 3H), 3.05-3.40 (m, 8H), 3.81 (m, 1H), 4.16 (q, J=6.9Hz, 2H), 7.00 (d, J=9.0 Hz, 2H), 7.19 (dd, J=2.7, 9.3 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 7.43 (d, J=8.7 Hz, 2H), 7.51 (dd, J=1.5, 8.4 Hz, 1H), 7.76-7.88 (m, 2H), 7.93 (d, J=9.0 Hz, 1H), 8.03 (s, 1H), 12.72 (br s, 1H).【００７７】
(S)-2-{4-[4-(6-エトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-ペンタン酸（I-28）の合成
1H NMR (DMSO-d6) δ: 0.88 (t, J=7.2 Hz, 3H), 1.40 (t, J=7.2 Hz, 3H), 1.28-1.48 (m, 2H), 1.50-1.68 (m, 2H), 3.05-3.40 (m, 8H), 3.68 (m, 1H), 4.15 (q, J=6.9Hz, 2H), 6.99 (d, J=9.0 Hz, 2H), 7.18 (dd, J=2.4, 9.0 Hz, 1H), 7.32 (d, J=2.4 Hz, 1H), 7.42 (d, J=8.4 Hz, 2H), 7.50 (dd, J=1.5, 8.7 Hz, 1H), 7.76-7.86 (m, 2H), 7.91 (d, J=9.0 Hz, 1H), 8.02 (s, 1H), 12.71 (br s, 1H).【００７８】
(R)-2-{4-[4-(ナフタレン-2-イルメトキシ)-フェニル]-ピペリジン-1-スルホニルアミノ)-プロピオン酸（I-29）の合成
1H NMR (DMSO-d6) δ: 1.29-1.31 (m, 3H), 1.57-1.59 (m, 2H), 1.75-1.78 (m, 2H), 2.65-2.77 (m, 2H), 3.60 (bs, 2H),  3.78 (bs, 1H), 6.99 (d, J=6.8 Hz, 2H), 7.15-7.17 (m, 2H), 7.51-7.58 (m, 3H), 7.69-7.74 (m, 4H).【００７９】
(S)-2-{4-[4-(ナフタレン-2-イルメトキシ)-フェニル]-ピペリジン-1-スルホニルアミノ)-ペンタン酸（I-30）の合成
1H NMR (DMSO-d6) δ: 0.89 (t, J=7.2 Hz, 3H), 1.37-1.40 (m, 2H), 1.53-1.58 (m, 3H), 1.74-1.81 (m, 2H), 2.60-2.72 (m, 2H), 3.59-3.69 (m, 2H),  5.25 (s, 2H), 6.99 (d, J=7.2 Hz, 2H), 7.15 (d, J=7.2 Hz, 2H), 7.51-7.58 (m, 3H), 7.68 (d, J=5.6 Hz, 1H), 7.92-7.97 (m, 4H).【００８０】
(S)-2-{4-[4-(6-メトキシメトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-31）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 3.05-3.40 (m, 8H), 3.42 (s, 3H), 3.80 (m, 1H), 5.33 (s, 2H), 7.00 (d, J=8.7 Hz, 2H), 7.28 (dd, J=2.1, 8.4 Hz, 1H), 7.36-7.56 (m, 4H), 7.81 (d, J=8.7 Hz, 1H), 7.87 (d, J=9.0 Hz, 1H), 7.92 (m, 1H), 8.04 (s, 1H), 12.70 (br s, 1H).【００８１】
(R)-2-{4-[4-(6-シクロプロピルメトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-32）の合成
1H NMR (DMSO-d6) δ: 0.32-0.42 (m, 2H), 0.56-0.66 (m, 2H), 1.30 (d, J=7.2 Hz, 3H), 3.05-3.40 (m, 8H), 3.81 (m, 1H), 3.95 (d, J=6.9 Hz, 2H), 7.00 (d, J=9.0 Hz, 2H), 7.22 (dd, J=2.1, 8.7 Hz, 1H), 7.36 (d, J=2.4 Hz, 1H), 7.43 (d, J=9.0 Hz, 2H), 7.50 (dd, J=1.2, 8.7 Hz, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.84 (d, J=9.3 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 8.02 (m, 1H), 12.72 (br s, 1H).【００８２】
(R)-2-{4-[4-(6-ヒドロキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-33）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=6.9 Hz, 3H), 3.05-3.40 (m, 8H), 3.81 (m, 1H), 7.00 (d, J=8.7 Hz, 2H), 7.08-7.16 (m, 2H), 7.38-7.48 (m, 3H), 7.69 (d, J=9.0 Hz, 1H), 7.78 (d, J=9.0 Hz, 1H), 7.93 (d, J=8.1 Hz, 1H), 7.97 (s, 1H), 9.94 (s, 1H), 12.75 (br s, 1H).【００８３】
(R)-2-{4-[4-(ナフタレン-2-イルメチルスルファニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-34）の合成
1H NMR (DMSO-d6) δ: 1.28 (d, J=6.8 Hz, 3H), 3.32 (bs, 8H), 3.79 (bs, 1H), 4.24 (s, 2H), 6.86 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 7.46-7.47 (m, 3H), 7.70 (s, 1H), 7.79-7.85 (m, 4H).【００８４】
(R)-2-{4-[4-(ナフタレン-2-イルメタンスルフィニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-35）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=6.8 Hz, 3H), 3.14-3.17 (m, 4H), 3.79-3.83 (m, 1H), 4.20 (d, J=8.4 Hz, 1H), 4.33 (d, J=8.4 Hz, 1H), 7.06 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.0 Hz, 1H), 7.39 (d, J=8.8 Hz, 2H), 7.47-7.52 (m, 2H), 7.65 (s, 1H), 7.81 (d, J=7.2 Hz, 2H), 7.89 (bs, 2H).【００８５】
(R)-2-{4-[4-(6-ヒドロキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-36）の合成
1H NMR (DMSO-d6) δ: 1.31 (d, J=6.8 Hz, 3H), 1.60-1.65 (m, 2H), 1.81-1.84 (m, 2H), 2.62-2.76 (m, 3H), 3.64 (bs, 2H), 3.80 (bs, 1H), 7.14 (d, J=8.0 Hz, 2H), 7.31 (d, J=8.0 Hz, 2H), 7.46-7.52 (m, 3H), 7.71 (d, J=8.8 Hz, 2H), 7.79 (d, J=8.8 Hz, 1H), 8.02 (bs, 1H).【００８６】
(R)-2-{4-[4-(ナフタレン-2-イルメタンスルホニル)-フェニル]-4-オキシ-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-37）の合成
1H NMR (DMSO-d6) δ: 1.28 (d, J=7.2 Hz, 3H), 3.24 (d, J=9.2 Hz, 2H), 3.53 (t, J=13.6 Hz, 2H), 3.70-3.82 (m, 3H), 4.00-4.06 (m, 2H), 4.94 (s, 2H), 7.31 (d, J=8.4 Hz, 2H), 7.53 (d, J=4.0 Hz, 2H), 7.69 (s, 1H), 7.82-7.92 (m, 6H), 8.38 (d, J=8.4 Hz, 2H).【００８７】
(R)-2-{4-[4-(ナフタレン-2-イルメタンスルホニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-38）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 3.09-3.17 (m, 4H), 3.37-3.39 (m, 4H), 3.77-3.83 (m, 1H), 4.70 (s, 2H), 7.02 (d, J=8.8 Hz, 2H), 7.27 (d, J=8.8 Hz, 1H), 7.47-7.53 (m, 4H), 7.69 (bs, 1H), 7.82 (d, J=8.0 Hz, 2H), 7.88-7.93 (m, 4H).【００８８】
(R)-2-(4-{4-[6-(2-ヒドロキシ-エトキシ)-ナフタレン-2-イルエチニル]-フェニル}-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-39）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 3.10-3.40 (m, 8H), 3.74-3.86 (m, 3H), 4.12 (t, J=5.4 Hz, 2H), 4.94 (m, 1H), 7.10 (d, J=9.0 Hz, 2H),  7.22 (dd, J=2.4, 9.3 Hz, 1H), 7.35 (d, J=2.4 Hz, 1H), 7.43 (d, J=8.7 Hz, 2H), 7.51 (d, J=8.7 Hz, 1H), 7.79-7.88 (m, 2H), 7.92 (d, J=7.2 Hz, 1H), 8.03 (s, 1H), 12.77 (br s, 1H).【００８９】
(R)-2-{(R)-3-メチル-4-[4-(ナフタレン-2-イルメトキシ)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-40）の合成
1H NMR (DMSO-d6) δ: 0.85 (d, J=5.6 Hz, 3H), 1.32 (d, J=6.8 Hz, 3H), 2.96-2.98 (m, 2H), 3.08 (bs, 3H), 3.66 (bs, 1H), 3.82 (bs, 1H), 5.20 (s, 2H), 6.94 (dd, J=8.0 Hz, 9.2 Hz, 4H), 7.52-7.58 (m, 3H), 7.79 (bs, 1H), 7.92-7.94 (m, 4H).【００９０】
(R)-2-{(2R,6S)-2,6-ジメチル-4-[4-(ナフタレン-2-イルメトキシ)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-41）の合成
1H NMR (DMSO-d6) δ: 1.27 (d, J=7.2 Hz, 3H), 1.40 (t, J=6.4 Hz, 6H), 2.97-2.71 (m, 2H), 3.62-3.66 (m, 1H), 3.91 (bs, 2H), 5.22 (s, 2H), 6.93 (dd, J=8.8 Hz, 9.2 Hz, 4H), 7.51-7.58 (m, 4H), 7.91-7.96 (m, 4H).【００９１】
(R)-2-(4-{4-[4-(ナフタレン-2-カルボニル)-アミノ]-フェニル}-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-42）の合成
1H NMR (DMSO-d6) δ: 1.31 (d, J=6.8 Hz, 3H), 3.18 (s, 8H), 3.80-3.85 (m, 1H), 6.99 (d, J=8.0 Hz, 2H), 7.61-7.71 (m, 4H), 7.91 (d, J=8.4 Hz, 1H), 7.99-8.09 (m, 4H), 8.56 (s, 1H), 10.27 (s, 1H), 12.73 (br s, 1H).【００９２】
(R)-2-{4-[4-(メチル-ナフタレン-2-イルメチル-アミノ)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-43）の合成
1H NMR (DMSO-d6) δ: 1.29 (d, J=6.8 Hz, 3H), 2.96 (s, 7H), 3.12 (s, 4H), 3.77-3.83 (m, 1H), 4.70 (s, 2H), 6.72 (d, J=7.6 Hz, 2H), 6.83 (d, J=7.6 Hz, 2H), 7.38 (d, J=8.0 Hz, 1H), 7.46-7.48 (m, 2H), 7.70 (s, 1H), 7.82-7.87 (m, 4H), 12.69 (br s, 1H).【００９３】
(R)-2-(4-{4-[4-(ナフタレン-2-イルメチル)-アミノ]-フェニル}-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-44）の合成
1H NMR (DMSO-d6) δ: 1.28 (d, J=6.8 Hz, 3H), 2.93 (s, 4H), 3.10 (s, 4H), 3.76-3.80 (m, 1H), 4.38 (s, 2H), 6.56 (d, J=7.6 Hz, 2H), 6.73 (d, J=7.6 Hz, 2H), 7.46-7.53 (m, 3H), 7.81-7.87 (m, 5H), 12.61 (br s, 1H).【００９４】
(R)-2-(4-{4-[4-(6-メトキシ-ナフタレン-2-イルメチル)-アミノ]-フェニル}-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-45）の合成
1H NMR (DMSO-d6) δ: 1.28 (d, J=6.8 Hz, 3H), 2.92 (s, 4H), 3.10 (s, 4H), 3.76-3.80 (m, 1H), 3.85 (s, 3H), 4.32 (s, 2H), 6.54 (d, J=7.6 Hz, 2H), 6.72 (d, J=7.6 Hz, 2H), 7.12 (d, J=8.6 Hz, 1H), 7.28 (s, 1H), 7.46 (d, J=8.6 Hz, 1H), 7.76 (s, 3H), 7.82 (d, J=7.6 Hz, 1H), 12.12 (br s, 1H).【００９５】
(R)-2-(4-{4-[4-(6-カルボキシメトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-46）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=6.6 Hz, 3H), 3.05-3.40 (m, 8H), 3.81 (m, 1H), 4.82 (s, 2H), 7.00 (d, J=8.4 Hz, 2H), 7.20-7.32 (m, 2H), 7.43 (d, J=8.1 Hz, 2H), 7.51 (d, J=8.7 Hz, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.87 (d, J=9.3 Hz, 1H), 7.93 (m, 1H), 8.04 (s, 1H), 12.40-13.40 (m, 2H).【００９６】
(R)-2-(4-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-2-メチル-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-47）の合成
1H NMR (DMSO-d6) δ: 1.22-1.32 (m, 6H), 2.65-3.30 (m, 4H), 3.55-3.80 (m, 3H), 3.89 (s, 3H), 3.95 (m, 1H), 6.97 (d, J=9.0 Hz, 2H), 7.21 (dd, J=2.7, 9.0 Hz, 1H), 7.35 (d, J=2.1 Hz, 1H), 7.42 (d, J=8.7 Hz, 2H), 7.52 (dd, J=1.5, 8.7 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.84 (d, J=9.3 Hz, 1H), 7.92 (m, 1H), 8.03 (s, 1H), 12.72 (br s, 1H).【００９７】
(R)-2-(4-{4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-[1,4]ジアゼパン-1-スルホニルアミノ}-プロピオン酸（I-48）の合成
1H NMR (DMSO-d6) δ: 1.25 (d, J=7.1 Hz, 3H), 3.22-3.61 (m, 11H), 3.93 (s, 3H), 6.81-6.84 (m, 2H), 7.23-7.26 (m, 1H), 7.39-7.42 (m, 3H), 7.52-7.64 (m, 2H), 7.81-7.91 (m, 2H), 8.03 (br s, 1H).【００９８】
(S)-2-(4-{4-[(E)-2-(6-メトキシメトキシ-ナフタレン-2-イル)-ビニル]-フェニル}-ピペラジン-1-スルホニルアミノ)-ペンタン酸（I-49）の合成
1H NMR (DMSO-d6) δ: 0.89 (t, J=6.8 Hz, 3H), 1.33-1.43 (m, 2H), 1.55-1.62 (m, 2H), 3.14-3.26 (m, 8H), 3.44-3.71 (m, 4H), 5.32 (s, 2H), 7.00 (d, J=8.4 Hz, 2H), 7.17-7,28 (m, 3H), 7.42 (s, 1H), 7.51 (d, J=8.4 Hz, 2H), 7.78 (s, 2H), 7.82-7.92 (m, 3H).【００９９】
(S)-2-(4-{4-[(E)-2-(6-ヒドロキシ-ナフタレン-2-イル)-ビニル]-フェニル}-ピペラジン-1-スルホニルアミノ)-ペンタン酸（I-50）の合成
1H NMR (DMSO-d6) δ: 0.89 (t, J=6.8 Hz, 3H), 1.33-1.43 (m, 2H), 1.55-1.62 (m, 2H), 3.14-3.26 (m, 8H), 3.67-3.71 (m, 1H), 6.98 (d, J=8.0 Hz, 2H), 7.05-7.23 (m, 4H), 7.49 (d, J=8.4 Hz, 2H), 7.64-7.73 (m, 3H) 7.81 (s, 1H), 7.90 (d, J=8.8 Hz, 1H), 9.75 (s, 1H), 12.73 (s, br s, 1H). 【０１００】
(S)-2-(4-{4-[(E)-2-(6-メトキシ-ナフタレン-2-イル)-ビニル]-フェニル}-[1,4]ジアゼパン-1-スルホニルアミノ)-ペンタン酸（I-51）の合成
1H NMR (DMSO-d6) δ: 0.84-0.87 (m, 3H), 1.25-1.35 (m, 3H), 1.48-1.58 (m, 2H), 1.84-1.94 (m, 2H), 3.10-3.63 (m, 11H), 3.89 (s, 3H), 6.77-6.80 (m, 2H), 7.18-7.22 (m, 1H), 7.35-7.38 (m, 3H), 7.49-7.51 (m, 1H), 7.60-7.63 (m, 1H), 7.80-7.85 (m, 2H), 8.00 (br s, 1H).【０１０１】
(R)-2-{4-[4-(6-エトキシ-ナフタレン-2-イルメトキシ)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-52）の合成
1H NMR (DMSO-d6) δ: 1.29 (d, J=8.0 Hz, 3H), 1.39 (t, J=8.0 Hz, 3H), 3.04-3.17 (m, 8H), 3.77-3.81 (m, 1H), 4.14 (dd, J=8.0 Hz, 12.0 Hz, 2H), 5.14 (s, 2H), 6.89-6.95 (m, 4H), 7.15 (d, J=8.4 Hz, 1H), 7.30 (s, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.79-7.86 (m, 4H).【０１０２】
(R)-2-{(S)-4-[4-(6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-3-メチルピペラジン-1-スルホニルアミノ}-プロピオン酸（I-53）の合成
1H NMR (DMSO-d6) δ: 1.02 (d, J=6.3 Hz, 3H), 1.28-1.35 (m, 3H), 2.60-3.10 (m, 4H), 3.45-3.60 (m, 2H), 3.85 (m, 1H), 3.89 (s, 3H), 4.25 (m, 1H), 6.94 (d, J=8.7 Hz, 2H), 7.21 (dd, J=2.7, 9.0 Hz, 1H), 7.35 (d, J=2.1 Hz, 1H), 7.42 (d, J=8.7 Hz, 2H), 7.52 (d, J=9.0 Hz, 1H), 7.78-7.88 (m, 2H), 8.00 (m, 1H), 8.03 (s, 1H), 12.70 (br s, 1H).【０１０３】
(R)-2-(4-{4-[6-((E)-3-ヒドロキシ-ブタ-1,3-ジエニル)-ナフタレン-2-イルエチニル]-フェニル}-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-55）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 3.13-3.33 (m, 8H), 3.81 (br s, 1H), 6.69 (d, J=15.9 Hz, 1H), 7.02 (d, J=8.7 Hz, 2H), 7.46 (d, J=8.7 Hz, 2H), 
7.59-7.62 (m, 1H), 7.74 (d, J=15.9 Hz, 1H), 7.90-7.97 (m, 4H), 8.13 (s, 1H), 8.20 (s, 1H), 12.6(br s, 1H).【０１０４】
(R)-2-{4-[4-(6-アセチルアミノ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-56）の合成
1H NMR (DMSO-d6) δ: 1.31 (d, J=7.2 Hz, 3H), 2.12 (s, 3H), 3.14-3.22 (m, 4H), 3.79-3.84 (m, 1H), 7.00 (d, J=8.8 Hz, 2H), 7.44 (d, J=8.4 Hz, 2H), 7.49-7.65 (m, 3H), 7.80-7.92 (m, 2H), 8.02 (s, 1H), 8.30 (s, 1H).【０１０５】
(R)-2-{4-[4-(6-アミノ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-57）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 2.54 (s, 2H), 3.15-3.17 (m, 4H), 3.80-3.84 (m, 1H), 6.95-7.00 (m, 3H), 7.40 (d, J=8.4 Hz, 2H), 7.49 (d, J=8.4 Hz, 1H), 7.60 (d, J=8.8 Hz, 1H), 7.81 (bs, 1H), 7.90 (d, J=8.4 Hz, 1H).【０１０６】
(R)-2-[4-(4-{2-[6-(2-カルボキシ-エチル)-ナフタレン-2-イル]エチル}-フェニル)-ピペラジン-1-スルホニルアミノ]-プロピオン酸（I-58）の合成
1H NMR (DMSO-d6) δ: 1.29 (d, J=7.2 Hz, 3H), 2.59-2.65 (m, 2H), 2.84-2.91 (m, 2H), 2.94-2.99 (m, 4H), 3.07-3.17 (m, 8H), 3.79 (br s, 1H),6.86 (d, J=8.4 Hz, 2H), 7.10 (d, J=8.4 Hz, 2H),7.34-7.40 (m, 2H), 7.63-7.67 (m, 2H), 7.71-7.76 (m, 2H), 7.86 (br s, 1H).【０１０７】
(R)-2-{4-[4-(6-ジメチルカルバモイルメトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-59）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=6.8 Hz, 3H), 2.87 (s, 3H), 3.05 (s, 3H), 3.13-3.22 (m, 4H), 3.25-3.31 (m, 4H), 3.78-3.82 (m, 1H), 4.94 (s, 2H), 7.00 (d, J=8.4 Hz, 2H), 7.23-7.29 (m, 2H), 7.43 (d, J=8.4 Hz, 2H), 7.51 (d, J=8.4 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.84-7.91(m, 2H), 8.03 (s, 1H).【０１０８】
6-{4-[4-((R)-1-カルボキシ-エチルスルファモイル)-ピペラジン-1-イル]-フェニルエチニル}-ナフタレン-2-カルボン酸（I-60）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.5 Hz, 3H), 3.05-3.40 (m, 8H), 3.81 (m, 1H), 7.02 (d, J=8.7 Hz, 2H), 7.47 (d, J=8.7 Hz, 2H), 7.65 (d, J=8.4 Hz, 1H), 7.92 (m, 1H), 8.01 (s, 2H), 8.14 (d, J=9.0 Hz, 1H), 8.19 (s, 1H), 8.61 (s, 1H), 13.00 (m, 1H).【０１０９】
(R)-2-[4-(4-ナフタレン-2-イルエチニル-フェニル)-ピペラジン-1-スルホニルアミノ]-プロピオン酸（I-61）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 3.08-3.35 (m, 8H), 3.81 (m, 1H), 7.02 (d, J=9.0 Hz, 2H), 7.46 (d, J=8.7 Hz, 2H), 7.52-7.60 (m, 3H), 7.88-7.98 (m, 4H), 8.12 (s, 1H), 12.69 (br s, 1H).【０１１０】
(R)-2-{4-[4-(6-メタンスルホニルアミノ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-62）の合成
1H NMR (DMSO-d6) δ: 1.31 (d, J=7.2 Hz, 3H), 3.09 (s, 3H), 3.16-3.20 (m, 4H), 3.30 (bs, 4H), 7.01 (d, J=8.8 Hz, 2H), 7.41-7.45 (m, 3H), 7.54 (d, J=8.4 Hz, 1H), 7.69 (s, 1H), 7.84-7.92 (m, 3H), 8.05 (s, 1H).【０１１１】
(S)-2-(4-{4-[(E)-2-(6-カルボキシメトキシ-ナフタレン-2-イル)-ビニル]-フェニル}-ピペラジン-1-スルホニルアミノ)-ペンタン酸（I-63）の合成
1H NMR (DMSO-d6) δ: 0.84-0.91 (m, 3H), 1.34-1.44 (m, 2H), 1.57-1.64 (m, 2H), 3.16-3.24 (m, 8H), 3.70-3.73 (m, 1H), 4.80 (s, 2H), 7.15-7.25 (m, 4H), 7.50 (d, J=8.4 Hz, 2H), 7.50 (d, J=8.4 Hz, 2H), 7.77-7.88 (m, 5H).【０１１２】
(R)-2-(4-{4-[6-(2-カルボキシ-エチル)-ナフタレン-2-イルエチニル]-フェニル}-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-64）の合成
1H NMR (DMSO-d6) δ: 1.29 (d, J=7.0 Hz, 3H), 2.64 (t, J=7.5 Hz, 2H), 2.99 (t, J=7.5 Hz, 2H), 3.10-3.42 (m, 8H), 3.79 (br s, 1H), 6.99 (d, J=8.7 Hz, 2H), 7.41-7.47 (m, 3H), 7.51 (d, J=7.6 Hz, 1H), 7.72 (s, 1H), 7.83 (d, J=8.7 Hz, 2H), 7.88 (br s, 1H), 8.05 (s, 1H).【０１１３】
(R)-2-(4-{4-[6-(メトキシイミノ-メチル)-ナフタレン-2-イルエチニル]-フェニル}-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-66）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 3.10-3.40 (m, 8H), 3.80 (m, 1H), 3.95 (s, 3H), 7.02 (d, J=9.0 Hz, 2H), 7.46 (d, J=8.7 Hz, 2H), 7.61 (d, J=8.7 Hz, 1H), 7.80-8.20 (m, 4H), 8.10 (d, J=12.6 Hz, 1H), 8.38 (s, 1H).【０１１４】
(R)-2-{4-[4-(6-モルホリン-4-イル-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ)-プロピオン酸（I-67）の合成
1H NMR (DMSO-d6) δ: 1.29 (d, J=7.2 Hz, 3H), 3.15-3.20 (m, 4H), 3.75-3.79 (m, 4H), 6.99 (d, J=8.4 Hz, 2H), 7.19 (s, 1H), 7.41-7.48 (m, 4H), 7.71 (d, J=8.0 Hz, 2H), 7.94 (s, 1H).【０１１５】
(R)-2-{4-[4-(6-ジメチルカルバモイル-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-68）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 2.98 (s, 3H), 3.04 (s, 3H), 3.12-3.40 (m, 8H), 3.80 (br s, 1H), 7.02 (d, J=8.9 Hz, 2H), 7.46 (d, J=8.9 Hz, 2H), 7.53-7.58 (m, 1H), 7.60-7.66 (m, 1H), 7.90 (br s, 1H), 7.96-8.02 (m, 3H), 8.16 (s, 1H).【０１１６】
(R)-2-{4-[4-(4-シアノ-6-メトキシメトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-83）の合成
1H NMR (DMSO-d6) δ: 1.31 (d, J=6.8 Hz, 3H), 3.15-3.21 (m, 4H), 3.46 (s, 3H), 3.82 (bs, 1H), 5.42 (s, 2H), 7.02 (d, J=8.8 Hz, 2H), 7.45-7.48 (m, 3H), 7.45-7.48 (m, 3H), 7.56 (s, 1H), 7.91 (bs, 1H), 8.08 (d, J=8.8, 1H),  8.20 (s, 1H), 8.41 (s, 1H).【０１１７】
(R)-2-{4-[4-(4-シアノ-6-ヒドロキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-84）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=6.8 Hz, 3H), 3.14-3.17 (m, 4H), 3.82 (bs, 1H), 7.01 (d, J=7.6 Hz, 2H), 7.28 (d, J=8.0 Hz, 1H), 7.36 (s, 1H), 7.44 (d, J=7.6 Hz, 2H), 7.99 (d, J=8.8, 1H),  8.12 (s, 1H), 8.34 (s, 1H).【０１１８】
3-{4-[4-((R)-1-カルボキシ-エチルスルファモイル)-ピペラジン-1-イル]-フェニルエチニル}-ナフタレン-2-カルボン酸（I-97）の合成
1H NMR (DMSO-d6) δ: 1.32 (d, J=6.8 Hz, 3H), 3.18 (bs, 8H), 3.81-3.85 (m, 1H), 7.03 (d, J=8.0 Hz, 2H), 7.43 (d, J=8.4 Hz, 2H), 7.61-7.69 (m, 2H),  7.91 (d, J=8.0 Hz, 1H), 7.99 (d, J=8.0 Hz, 1H), 8.08 (d, J=8.4 Hz, 1H), 8.22 (s, 1H), 8.52 (s, 1H).【０１１９】
(R)-2-{4-[4-(6-アセチル-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-116）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 2.71 (s, 3H), 3.05-3.40 (m, 8H), 3.81 (m, 1H), 7.03 (d, J=9.0 Hz, 2H), 7.47 (d, J=9.0 Hz, 2H), 7.67 (d, J=1.5, 8.4 Hz, 1H), 7.92 (m, 1H), 7.96-8.06 (m, 2H), 8.15 (d, J=8.4 Hz, 1H), 8.19(s, 1H), 8.68 (s, 1H), 12.77 (br s, 1H).【０１２０】
(R)-2-{4-[4-(9H-カルバゾール-3-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-129）の合成
1H NMR (DMSO-d6) δ: 1.30 (d, J=7.2 Hz, 3H), 3.15-3.21 (m, 4H), 3.82 (bs, 1H), 6.99 (d, J=8.8 Hz, 2H), 7.19 (d, J=7.2 Hz, 1H), 7.42 (d, J=8.8 Hz, 3H),  7.49-7.51 (m, 1H), 8.18 (d, J=8.4 Hz, 1H), 8.32 (s, 1H).【０１２１】
(S)-2-[4-(4-ナフタレン-2-イルエチニル-フェニル)-ピペラジン-1-スルホニルアミノ]-ペンタン酸（I-132）の合成
1H NMR (DMSO-d6) δ: 0.88 (t, J=6.9 Hz, 3H), 1.30-1.70 (m, 4H), 3.05-3.40 (m, 8H), 3.69 (m, 1H), 7.02 (d, J=9.0 Hz, 2H), 7.46 (d, J=8.7 Hz, 2H), 7.52-7.60 (m, 3H), 7.86-8.00 (m, 4H), 8.12 (s, 1H), 12.77 (br s, 1H).【０１２２】
(R)-2-{4-[4-(4-シアノ-6-メトキシ-ナフタレン-2-イルエチニル)-フェニル]-ピペラジン-1-スルホニルアミノ}-プロピオン酸（I-133）の合成
1H NMR (DMSO-d6) δ: 1.31 (d, J=7.2 Hz, 3H), 3.15-3.20 (m, 4H), 3.81(t, J=6.0 Hz, 1H), 3.98 (s, 3H), 7.02 (d, J=8.4 Hz, 2H), 7.34 (s, 1H), 7.40 (d, J=9.2 Hz, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.92 (d, J=9.2 Hz, 1H), 8.05 (d, J=9.2 Hz, 1H), 8.20 (s, 1H), 8.41(s, 1H).【０１２３】
上記と同様の方法で、一般式（Ｉ’）： 
【化４２】
2007102392.tif 000044
［式中、Ｒ１は、
【化４３】
2007102392.tif 000045
で示される基；
Ｚは、(b1)−ＣＨ２Ｏ−、(b2) −ＯＣＨ２−、(b3) −ＮＨＣＨ２−、(b4) −ＣＨ２ＮＨ−、(b5) −ＣＨ２Ｓ−、(b6) −ＣＨ２ＳＯ−、(b7) −ＣＨ２ＳＯ２−、(b8) −ＳＣＨ２−、(b9) −ＳＯＣＨ２−、(b10) −ＳＯ２ＣＨ２−、(b11) −Ｃ（＝Ｏ）Ｃ（＝Ｏ）−、(b12) −ＣＨ２ＣＨ２−、 (b 13) −ＣＨ＝ＣＨ−、(b14) −Ｃ≡Ｃ−、または(b15) −ＮＨ−Ｃ（＝Ｏ）−；
Ａは、
【化４４】
2007102392.tif 000046
で示される基；
Ｒ３は、(d1)ベンジル、(d2)インドール−３−イルメチル、(d3)イソブチル、(d4)メチル、(d5)２−メチルチオエチル、(d6)イソプロピル、(d7)ｓｅｃ−ブチル、(d8) ｔ−ブチル、(d9) ｎ−プロピル、(d10) ｎ−ブチル、(d11)ヒドロキシメチル、または(d12) ４−ヒドロキシベンジル］で表される化合物において、
（Ｒ１，Ｚ，Ａ，Ｒ３）＝(a1, b1, c1, d1), (a1, b1, c1, d2), (a1, b1, c1, d3), (a1, b1, c1, d4), (a1, b1, c1, d5), (a1, b1, c1, d6), (a1, b1, c1, d7), (a1, b1, c1, d8), (a1, b1, c1, d9), (a1, b1, c1, d10), (a1, b1, c1, d11), (a1, b1, c1, d12), (a1, b1, c2, d1), (a1, b1, c2, d2), (a1, b1, c2, d3), (a1, b1, c2, d4), (a1, b1, c2, d5), (a1, b1, c2, d6), (a1, b1, c2, d7), (a1, b1, c2, d8), (a1, b1, c2, d9), (a1, b1, c2, d10), (a1, b1, c2, d11), (a1, b1, c2, d12), (a1, b1, c3, d1), (a1, b1, c3, d2), (a1, b1, c3, d3), (a1, b1, c3, d4), (a1, b1, c3, d5), (a1, b1, c3, d6), (a1, b1, c3, d7), (a1, b1, c3, d8), (a1, b1, c3, d9), (a1, b1, c3, d10), (a1, b1, c3, d11), (a1, b1, c3, d12), (a1, b1, c4, d1), (a1, b1, c4, d2), (a1, b1, c4, d3), (a1, b1, c4, d4), (a1, b1, c4, d5), (a1, b1, c4, d6), (a1, b1, c4, d7), (a1, b1, c4, d8), (a1, b1, c4, d9), (a1, b1, c4, d10), (a1, b1, c4, d11), (a1, b1, c4, d12), (a1, b1, c5, d1), (a1, b1, c5, d2), (a1, b1, c5, d3), (a1, b1, c5, d4), (a1, b1, c5, d5), (a1, b1, c5, d6), (a1, b1, c5, d7), (a1, b1, c5, d8), (a1, b1, c5, d9), (a1, b1, c5, d10), (a1, b1, c5, d11), (a1, b1, c5, d12), (a1, b1, c6, d1), (a1, b1, c6, d2), (a1, b1, c6, d3), (a1, b1, c6, d4), (a1, b1, c6, d5), (a1, b1, c6, d6), (a1, b1, c6, d7), (a1, b1, c6, d8), (a1, b1, c6, d9), (a1, b1, c6, d10), (a1, b1, c6, d11), (a1, b1, c6, d12), (a1, b1, c7, d1), (a1, b1, c7, d2), (a1, b1, c7, d3), (a1, b1, c7, d4), (a1, b1, c7, d5), (a1, b1, c7, d6), (a1, b1, c7, d7), (a1, b1, c7, d8), (a1, b1, c7, d9), (a1, b1, c7, d10), (a1, b1, c7, d11), (a1, b1, c7, d12), (a1, b1, c8, d1), (a1, b1, c8, d2), (a1, b1, c8, d3), (a1, b1, c8, d4), (a1, b1, c8, d5), (a1, b1, c8, d6), (a1, b1, c8, d7), (a1, b1, c8, d8), (a1, b1, c8, d9), (a1, b1, c8, d10), (a1, b1, c8, d11), (a1, b1, c8, d12), (a1, b1, c9, d1), (a1, b1, c9, d2), (a1, b1, c9, d3), (a1, b1, c9, d4), (a1, b1, c9, d5), (a1, b1, c9, d6), (a1, b1, c9, d7), (a1, b1, c9, d8), (a1, b1, c9, d9), (a1, b1, c9, d10), (a1, b1, c9, d11), (a1, b1, c9, d12), (a1, b1, c10, d1), (a1, b1, c10, d2), (a1, b1, c10, d3), (a1, b1, c10, d4), (a1, b1, c10, d5), (a1, b1, c10, d6), (a1, b1, c10, d7), (a1, b1, c10, d8), (a1, b1, c10, d9), (a1, b1, c10, d10), (a1, b1, c10, d11), (a1, b1, c10, d12), (a1, b1, c11, d1), (a1, b1, c11, d2), (a1, b1, c11, d3), (a1, b1, c11, d4), (a1, b1, c11, d5), (a1, b1, c11, d6), (a1, b1, c11, d7), (a1, b1, c11, d8), (a1, b1, c11, d9), (a1, b1, c11, d10), (a1, b1, c11, d11), (a1, b1, c11, d12), (a1, b1, c12, d1), (a1, b1, c12, d2), (a1, b1, c12, d3), (a1, b1, c12, d4), (a1, b1, c12, d5), (a1, b1, c12, d6), (a1, b1, c12, d7), (a1, b1, c12, d8), (a1, b1, c12, d9), (a1, b1, c12, d10), (a1, b1, c12, d11), (a1, b1, c12, d12), (a1, b1, c13, d1), (a1, b1, c13, d2), (a1, b1, c13, d3), (a1, b1, c13, d4), (a1, b1, c13, d5), (a1, b1, c13, d6), (a1, b1, c13, d7), (a1, b1, c13, d8), (a1, b1, c13, d9), (a1, b1, c13, d10), (a1, b1, c13, d11), (a1, b1, c13, d12), (a1, b2, c1, d1), (a1, b2, c1, d2), (a1, b2, c1, d3), (a1, b2, c1, d4), (a1, b2, c1, d5), (a1, b2, c1, d6), (a1, b2, c1, d7), (a1, b2, c1, d8), (a1, b2, c1, d9), (a1, b2, c1, d10), (a1, b2, c1, d11), (a1, b2, c1, d12), (a1, b2, c2, d1), (a1, b2, c2, d2), (a1, b2, c2, d3), (a1, b2, c2, d4), (a1, b2, c2, d5), (a1, b2, c2, d6), (a1, b2, c2, d7), (a1, b2, c2, d8), (a1, b2, c2, d9), (a1, b2, c2, d10), (a1, b2, c2, d11), (a1, b2, c2, d12), (a1, b2, c3, d1), (a1, b2, c3, d2), (a1, b2, c3, d3), (a1, b2, c3, d4), (a1, b2, c3, d5), (a1, b2, c3, d6), (a1, b2, c3, d7), (a1, b2, c3, d8), (a1, b2, c3, d9), (a1, b2, c3, d10), (a1, b2, c3, d11), (a1, b2, c3, d12), (a1, b2, c4, d1), (a1, b2, c4, d2), (a1, b2, c4, d3), (a1, b2, c4, d4), (a1, b2, c4, d5), (a1, b2, c4, d6), (a1, b2, c4, d7), (a1, b2, c4, d8), (a1, b2, c4, d9), (a1, b2, c4, d10), (a1, b2, c4, d11), (a1, b2, c4, d12), (a1, b2, c5, d1), (a1, b2, c5, d2), (a1, b2, c5, d3), (a1, b2, c5, d4), (a1, b2, c5, d5), (a1, b2, c5, d6), (a1, b2, c5, d7), (a1, b2, c5, d8), (a1, b2, c5, d9), (a1, b2, c5, d10), (a1, b2, c5, d11), (a1, b2, c5, d12), (a1, b2, c6, d1), (a1, b2, c6, d2), (a1, b2, c6, d3), (a1, b2, c6, d4), (a1, b2, c6, d5), (a1, b2, c6, d6), (a1, b2, c6, d7), (a1, b2, c6, d8), (a1, b2, c6, d9), (a1, b2, c6, d10), (a1, b2, c6, d11), (a1, b2, c6, d12), (a1, b2, c7, d1), (a1, b2, c7, d2), (a1, b2, c7, d3), (a1, b2, c7, d4), (a1, b2, c7, d5), (a1, b2, c7, d6), (a1, b2, c7, d7), (a1, b2, c7, d8), (a1, b2, c7, d9), (a1, b2, c7, d10), (a1, b2, c7, d11), (a1, b2, c7, d12), (a1, b2, c8, d1), (a1, b2, c8, d2), (a1, b2, c8, d3), (a1, b2, c8, d4), (a1, b2, c8, d5), (a1, b2, c8, d6), (a1, b2, c8, d7), (a1, b2, c8, d8), (a1, b2, c8, d9), (a1, b2, c8, d10), (a1, b2, c8, d11), (a1, b2, c8, d12), (a1, b2, c9, d1), (a1, b2, c9, d2), (a1, b2, c9, d3), (a1, b2, c9, d4), (a1, b2, c9, d5), (a1, b2, c9, d6), (a1, b2, c9, d7), (a1, b2, c9, d8), (a1, b2, c9, d9), (a1, b2, c9, d10), (a1, b2, c9, d11), (a1, b2, c9, d12), (a1, b2, c10, d1), (a1, b2, c10, d2), (a1, b2, c10, d3), (a1, b2, c10, d4), (a1, b2, c10, d5), (a1, b2, c10, d6), (a1, b2, c10, d7), (a1, b2, c10, d8), (a1, b2, c10, d9), (a1, b2, c10, d10), (a1, b2, c10, d11), (a1, b2, c10, d12), (a1, b2, c11, d1), (a1, b2, c11, d2), (a1, b2, c11, d3), (a1, b2, c11, d4), (a1, b2, c11, d5), (a1, b2, c11, d6), (a1, b2, c11, d7), (a1, b2, c11, d8), (a1, b2, c11, d9), (a1, b2, c11, d10), (a1, b2, c11, d11), (a1, b2, c11, d12), (a1, b2, c12, d1), (a1, b2, c12, d2), (a1, b2, c12, d3), (a1, b2, c12, d4), (a1, b2, c12, d5), (a1, b2, c12, d6), (a1, b2, c12, d7), (a1, b2, c12, d8), (a1, b2, c12, d9), (a1, b2, c12, d10), (a1, b2, c12, d11), (a1, b2, c12, d12), (a1, b2, c13, d1), (a1, b2, c13, d2), (a1, b2, c13, d3), (a1, b2, c13, d4), (a1, b2, c13, d5), (a1, b2, c13, d6), (a1, b2, c13, d7), (a1, b2, c13, d8), (a1, b2, c13, d9), (a1, b2, c13, d10), (a1, b2, c13, d11), (a1, b2, c13, d12), (a1, b3, c1, d1), (a1, b3, c1, d2), (a1, b3, c1, d3), (a1, b3, c1, d4), (a1, b3, c1, d5), (a1, b3, c1, d6), (a1, b3, c1, d7), (a1, b3, c1, d8), (a1, b3, c1, d9), (a1, b3, c1, d10), (a1, b3, c1, d11), 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c2, d12), (a6, b14, c3, d1), (a6, b14, c3, d2), (a6, b14, c3, d3), (a6, b14, c3, d4), (a6, b14, c3, d5), (a6, b14, c3, d6), (a6, b14, c3, d7), (a6, b14, c3, d8), (a6, b14, c3, d9), (a6, b14, c3, d10), (a6, b14, c3, d11), (a6, b14, c3, d12), (a6, b14, c4, d1), (a6, b14, c4, d2), (a6, b14, c4, d3), (a6, b14, c4, d4), (a6, b14, c4, d5), (a6, b14, c4, d6), (a6, b14, c4, d7), (a6, b14, c4, d8), (a6, b14, c4, d9), (a6, b14, c4, d10), (a6, b14, c4, d11), (a6, b14, c4, d12), (a6, b14, c5, d1), (a6, b14, c5, d2), (a6, b14, c5, d3), (a6, b14, c5, d4), (a6, b14, c5, d5), (a6, b14, c5, d6), (a6, b14, c5, d7), (a6, b14, c5, d8), (a6, b14, c5, d9), (a6, b14, c5, d10), (a6, b14, c5, d11), (a6, b14, c5, d12), (a6, b14, c6, d1), (a6, b14, c6, d2), (a6, b14, c6, d3), (a6, b14, c6, d4), (a6, b14, c6, d5), (a6, b14, c6, d6), (a6, b14, c6, d7), (a6, b14, c6, d8), (a6, b14, c6, d9), (a6, b14, c6, d10), (a6, b14, c6, d11), (a6, b14, c6, d12), (a6, b14, c7, d1), (a6, b14, c7, d2), (a6, b14, c7, d3), (a6, b14, c7, d4), (a6, b14, c7, d5), (a6, b14, c7, d6), (a6, b14, c7, d7), (a6, b14, c7, d8), (a6, b14, c7, d9), (a6, b14, c7, d10), (a6, b14, c7, d11), (a6, b14, c7, d12), (a6, b14, c8, d1), (a6, b14, c8, d2), (a6, b14, c8, d3), (a6, b14, c8, d4), (a6, b14, c8, d5), (a6, b14, c8, d6), (a6, b14, c8, d7), (a6, b14, c8, d8), (a6, b14, c8, d9), (a6, b14, c8, d10), (a6, b14, c8, d11), (a6, b14, c8, d12), (a6, b14, c9, d1), (a6, b14, c9, d2), (a6, b14, c9, d3), (a6, b14, c9, d4), (a6, b14, c9, d5), (a6, b14, c9, d6), (a6, b14, c9, d7), (a6, b14, c9, d8), (a6, b14, c9, d9), (a6, b14, c9, d10), (a6, b14, c9, d11), (a6, b14, c9, d12), (a6, b14, c10, d1), (a6, b14, c10, d2), (a6, b14, c10, d3), (a6, b14, c10, d4), (a6, b14, c10, d5), (a6, b14, c10, d6), (a6, b14, c10, d7), (a6, b14, c10, d8), (a6, b14, c10, d9), (a6, b14, c10, d10), (a6, b14, c10, d11), (a6, b14, c10, d12), (a6, b14, c11, d1), (a6, b14, c11, d2), (a6, b14, c11, d3), (a6, b14, c11, d4), (a6, b14, c11, d5), (a6, b14, c11, d6), (a6, b14, c11, d7), (a6, b14, c11, d8), (a6, b14, c11, d9), (a6, b14, c11, d10), (a6, b14, c11, d11), (a6, b14, c11, d12), (a6, b14, c12, d1), (a6, b14, c12, d2), (a6, b14, c12, d3), (a6, b14, c12, d4), (a6, b14, c12, d5), (a6, b14, c12, d6), (a6, b14, c12, d7), 
(a6, b14, c12, d8), (a6, b14, c12, d9), (a6, b14, c12, d10), (a6, b14, c12, d11), (a6, b14, c12, d12), (a6, b14, c13, d1), (a6, b14, c13, d2), (a6, b14, c13, d3), (a6, b14, c13, d4), (a6, b14, c13, d5), (a6, b14, c13, d6), (a6, b14, c13, d7), (a6, b14, c13, d8), (a6, b14, c13, d9), (a6, b14, c13, d10), (a6, b14, c13, d11), (a6, b14, c13, d12), (a6, b15, c1, d1), (a6, b15, c1, d2), (a6, b15, c1, d3), (a6, b15, c1, d4), (a6, b15, c1, d5), (a6, b15, c1, d6), (a6, b15, c1, d7), (a6, b15, c1, d8), (a6, b15, c1, d9), (a6, b15, c1, d10), (a6, b15, c1, d11), (a6, b15, c1, d12), (a6, b15, c2, d1), (a6, b15, c2, d2), (a6, b15, c2, d3), (a6, b15, c2, d4), (a6, b15, c2, d5), (a6, b15, c2, d6), (a6, b15, c2, d7), (a6, b15, c2, d8), (a6, b15, c2, d9), (a6, b15, c2, d10), (a6, b15, c2, d11), (a6, b15, c2, d12), (a6, b15, c3, d1), (a6, b15, c3, d2), (a6, b15, c3, d3), (a6, b15, c3, d4), (a6, b15, c3, d5), (a6, b15, c3, d6), (a6, b15, c3, d7), (a6, b15, c3, d8), (a6, b15, c3, d9), (a6, b15, c3, d10), (a6, b15, c3, d11), (a6, b15, c3, d12), (a6, b15, c4, d1), (a6, b15, c4, d2), (a6, b15, c4, d3), (a6, b15, c4, d4), (a6, b15, c4, d5), (a6, b15, c4, d6), (a6, b15, c4, d7), (a6, b15, c4, d8), (a6, b15, c4, d9), (a6, b15, c4, d10), (a6, b15, c4, d11), (a6, b15, c4, d12), (a6, b15, c5, d1), (a6, b15, c5, d2), (a6, b15, c5, d3), (a6, b15, c5, d4), (a6, b15, c5, d5), (a6, b15, c5, d6), (a6, b15, c5, d7), (a6, b15, c5, d8), (a6, b15, c5, d9), (a6, b15, c5, d10), (a6, b15, c5, d11), (a6, b15, c5, d12), (a6, b15, c6, d1), (a6, b15, c6, d2), (a6, b15, c6, d3), (a6, b15, c6, d4), (a6, b15, c6, d5), (a6, b15, c6, d6), (a6, b15, c6, d7), (a6, b15, c6, d8), (a6, b15, c6, d9), (a6, b15, c6, d10), (a6, b15, c6, d11), (a6, b15, c6, d12), (a6, b15, c7, d1), (a6, b15, c7, d2), (a6, b15, c7, d3), (a6, b15, c7, d4), (a6, b15, c7, d5), (a6, b15, c7, d6), (a6, b15, c7, d7), (a6, b15, c7, d8), (a6, b15, c7, d9), (a6, b15, c7, d10), (a6, b15, c7, d11), (a6, b15, c7, d12), (a6, b15, c8, d1), (a6, b15, c8, d2), (a6, b15, c8, d3), (a6, b15, c8, d4), (a6, b15, c8, d5), (a6, b15, c8, d6), (a6, b15, c8, d7), (a6, b15, c8, d8), (a6, b15, c8, d9), (a6, b15, c8, d10), (a6, b15, c8, d11), (a6, b15, c8, d12), (a6, b15, c9, d1), (a6, b15, c9, d2), (a6, b15, c9, d3), (a6, b15, c9, d4), (a6, b15, c9, d5), (a6, b15, c9, d6), (a6, b15, c9, d7), (a6, b15, c9, d8), (a6, b15, c9, d9), (a6, b15, c9, d10), (a6, b15, c9, d11), (a6, b15, c9, d12), (a6, b15, c10, d1), (a6, b15, c10, d2), (a6, b15, c10, d3), (a6, b15, c10, d4), (a6, b15, c10, d5), (a6, b15, c10, d6), (a6, b15, c10, d7), (a6, b15, c10, d8), (a6, b15, c10, d9), (a6, b15, c10, d10), (a6, b15, c10, d11), (a6, b15, c10, d12), (a6, b15, c11, d1), (a6, b15, c11, d2), (a6, b15, c11, d3), (a6, b15, c11, d4), (a6, b15, c11, d5), (a6, b15, c11, d6), (a6, b15, c11, d7), (a6, b15, c11, d8), (a6, b15, c11, d9), (a6, b15, c11, d10), (a6, b15, c11, d11), (a6, b15, c11, d12), (a6, b15, c12, d1), (a6, b15, c12, d2), (a6, b15, c12, d3), (a6, b15, c12, d4), (a6, b15, c12, d5), (a6, b15, c12, d6), (a6, b15, c12, d7), (a6, b15, c12, d8), (a6, b15, c12, d9), (a6, b15, c12, d10), (a6, b15, c12, d11), (a6, b15, c12, d12), (a6, b15, c13, d1), (a6, b15, c13, d2), (a6, b15, c13, d3), (a6, b15, c13, d4), (a6, b15, c13, d5), (a6, b15, c13, d6), (a6, b15, c13, d7), (a6, b15, c13, d8), (a6, b15, c13, d9), (a6, b15, c13, d10), (a6, b15, c13, d11), (a6, b15, c13, d12)で示される化合物を合成する。【０１２４】
試験例１  ＭＭＰの調製
各種ヒトMMP（MMP-2，MMP-9およびMMP-13）はCalbiochem （EMD/MERCK Biosciences）社より購入した。
MMP-13はProenzymeのため，酵素溶液にアッセイ用Buffer（50 mM Tris-HCl (pH7.6), 0.3 M NaCl, 10 mM CaCl2, 0.005% Brij35含有）を加えた後APMA（終濃度１mＭ）を添加し，37℃で2時間インキュベートして活性化したものを使用する。【０１２５】
試験例２  各種MMPの酵素阻害活性の測定方法
MMPの酵素活性測定法は、C. Graham Knight, Frances Willenbrock and Gillian Murphy ：A novel coumarin-labelled peptide for sensitive continuous assays of the matrix metalloproteinases： FEBS LETT., 296, (1992), 263-266の方法に準じた。基質はMOCAc-Pro-Leu-Gly-Leu-A2Pr(DNP)-Ala-Arg-NH2（Peptide Institute、Inc．Osaka、Japan）を用い、阻害活性の測定には1つの化合物(阻害剤)について次の4つのアッセイを行う。
（Ａ）基質(合成基質)、酵素(MMPs)、阻害剤
（Ｂ）基質(合成基質)、阻害剤
（Ｃ）基質(合成基質)、酵素(MMPs)
（Ｄ）基質(合成基質)
それぞれについて蛍光強度を測定し、次式により阻害(%)を求めた。
阻害(%)=｛1−(A−B)／(C−D)｝Ｘ100
IC50は阻害(%)が50%になる濃度を示す。
上記の方法により測定したMMP-2、MMP-9およびMMP-13に対する阻害活性値を表１に示した。【０１２６】
【表１】
2007102392.tif 000047
製剤例【０１２７】
製剤例１
以下の成分を含有する顆粒剤を製造する。
成分        活性成分                                   10 mg
乳糖                                      700 mg
コーンスターチ                            274 mg
HPC-L                                     16 mg
1000 mg
活性成分と乳糖を６０メッシュのふるいに通す。コーンスターチを１２０メッシュのふるいに通す。これらをV型混合機にて混合する。混合末にＨＰＣ−Ｌ（低粘度ヒドロキシプロピルセルロース）水溶液を添加し、練合、造粒（押し出し造粒  孔径０．５〜１ｍｍ）したのち、乾燥する。得られた乾燥顆粒を振動ふるい（１２／６０メッシュ）で櫛過し顆粒剤を得る。【０１２８】
製剤例２
以下の成分を含有するカプセル充填用散剤を製造する。
成分        活性成分                                  10 mg
乳糖                                      79 mg
コーンスターチ                            10 mg
ステアリン酸マグネシウム                   1 mg
100 mg
活性成分、乳糖を６０メッシュのふるいに通す。コーンスターチは１２０メッシュのふるいに通す。これらとステアリン酸マグネシウムをV型混合機にて混合する。１０倍散１００ｍｇを５号硬ゼラチンカプセルに充填する。【０１２９】
製剤例３
以下の成分を含有する錠剤を製造する。
成分        活性成分                                  10 mg
乳糖                                      90 mg
微結晶セルロース                          30 mg
CMC-Na                                  15 mg
ステアリン酸マグネシウム                   5 mg
150 mg
活性成分、乳糖、微結晶セルロース、ＣＭＣ−Ｎａ（カルボキシメチルセルロース  ナトリウム塩）を６０メッシュのふるいに通し、混合する。混合末にステアリン酸マグネシウム混合し、製錠用混合末を得る。本混合末を直打し、１５０ｍｇの錠剤を得る。【０１３０】
製剤例４
以下の成分を含有するエアロゾル溶液を製造する：
重量      
活性成分                                          ０．２５
エタノール                                      ２５．７５
プロペラント２２（クロロジフルオロメタン）      ７４．００  
合計                                        １００．００
活性成分とエタノールを混合し、この混合物をプロペラント２２の一部に加え、−３０℃に冷却し、充填装置に移す。ついで必要量をステンレススチール容器へ供給し、残りのプロペラントで希釈する。バブルユニットを容器に取り付ける。【０１３１】
製剤例５
静脈用製剤は次のように製造する：
活性成分                                    １００ｍｇ
生理食塩水                                １０００ｍｌ
上記成分の溶液は通常、１分間に１ｍｌの速度で患者に静脈内投与される。【０１３２】
製剤例６
以下の成分を含有する経皮製剤を製造する。
活性成分                                      １０ｍｇ
ミリスチン酸イソプロピル                    ９９０ｍｇ
１０００ｍｇ
式（Ｉ）で表わされる化合物をミリスチン酸イソプロピルに分散後、アクリル系粘着剤（例えばニカゾール）に混合し、貼付用支持体に添付することにより、経皮製剤を得る。【０１３３】
製剤例７
以下の成分を含有する軟膏剤を製造する。
活性成分                                    １０ｍｇ
流動パラフィン                              ７５ｍｇ
白色ワセリン                              ９２５ｍｇ
１０００ｍｇ
式（Ｉ）で表わされる化合物と流動パラフィンを分散させ、白色ワセリンと練合し軟膏剤を得る。
【産業上の利用可能性】
【０１３４】
本発明のＭＭＰ−１３選択的阻害活性を有するスルホンアミド誘導体は、ＭＭＰ−１３が関連する疾患、とりわけ変形性関節症の治療または予防のための医薬品として有用である。
【国際調査報告】
2007102392.tif 000058
2007102392.tif 000059
2007102392.tif 000060
2007102392.tif 000061
2007102392.tif 000062
2007102392.tif 000063
2007102392.tif 000064
2007102392.tif 000065