JP2006273847A

JP2006273847A - Cinnamoyl compound and its application

Info

Publication number: JP2006273847A
Application number: JP2006054781A
Authority: JP
Inventors: Hiroaki Shiraki; 宏明白木; Seishi Azuma; 清史東; Yoshitaka Tomigahara; 祥隆冨ヶ原; Junya Takahashi; 淳也高橋
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2005-03-02
Filing date: 2006-03-01
Publication date: 2006-10-12

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new compound and a medicinal composition (namely an extracellular matrix accumulation inhibitor, a therapeutic agent for fibrosis, a therapeutic agent for cardiac insufficiency, a TGF-β action inhibitor or a hair tonic) for improving fibrosis of a tissue by decreasing expression level of an extracellular matrix gene in the tissue and lowering extracellular matrix accumulation amount. <P>SOLUTION: The present invention provides a cinnamoyl compound represented by formula (I) [wherein α represents an aromatic five-membered ring or an aromatic six-membered ring having two or more nitrogen atoms; X<SB>α</SB>and Y<SB>α</SB>are each a substituent; p and q each represents 0, 1, 2 or 3 and the sum of p and q is ≤3] and an extracellular matrix gene transcription-inhibiting composition containing the compound. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

本発明は、シンナモイル化合物及びその用途等に関する。 The present invention relates to cinnamoyl compounds and uses thereof.

肝硬変、慢性膵炎、スキルス胃癌、間質性肺疾患、喘息、慢性閉塞性肺疾患、糸球体腎炎、ループス腎炎、尿細管間質性腎炎、ＩｇＡ腎症、腎硬化症、糖尿病性腎症、遺伝性腎疾患、心筋線維症、心不全、ＰＴＣＡ後の再狭窄、動脈硬化、骨髄線維症、関節リウマチ、炎症後の過形成痕跡、術後の瘢痕や熱傷性瘢痕、アトピー性皮膚炎、肥厚性瘢痕、子宮筋腫、前立腺肥大症、強皮症、アルツハイマー病、硬化性腹膜炎、糖尿病性網膜症、I型糖尿病においては、コラーゲン及びフィブロネクチンに代表されるような細胞外マトリックスの過度の集積により組織が線維化して硬化し、その結果、臓器・組織の機能低下や瘢痕形成等に至る。このような細胞外マトリックスの過度の集積は、細胞外マトリックスの生合成と分解とのバランスの破綻に基づく細胞外マトリックスの産生亢進によって導かれる。実際、線維化した組織においては、コラーゲン遺伝子（特にＩ型コラーゲン、III型コラーゲン、IV型コラーゲン）や、フィブロネクチン遺伝子、ラミニン遺伝子、プロテオグリカン遺伝子等といった細胞外マトリックス遺伝子の発現量が増加していることが観察されている（例えば、非特許文献１〜６参照）。
また、線維化した組織においては、サイトカインの１種であるＴＧＦ−βの量が上昇していることも観察されている（例えば、非特許文献１、２参照）。ＴＧＦ−βは、細胞外マトリックス遺伝子の発現量を増加させ、細胞外マトリックスタンパクの産生亢進、ひいては、組織の線維化に関与していることが示唆されている（例えば、非特許文献１、７参照）。さらに、組織線維化のモデル動物に対し、抗ＴＧＦ−β抗体や可溶性ＴＧＦ−β受容体を投与することにより、組織の線維化が改善され、それに伴い組織機能が改善されることが明らかにされており（例えば、非特許文献８〜１０参照）、またＴＧＦ−βの細胞内シグナル伝達に対し、抑制的に働く化合物を投与することにより、組織の線維化が改善され、それに伴い組織機能が改善されることも知られている（例えば、非特許文献１１〜１３参照）。
一方、左室拡張不全等の心不全や糖尿病性腎症や腎硬化症等の腎不全の病因は、高血圧状態の心臓線維化がその１つとされている。 Cirrhosis, chronic pancreatitis, Skills gastric cancer, interstitial lung disease, asthma, chronic obstructive pulmonary disease, glomerulonephritis, lupus nephritis, tubulointerstitial nephritis, IgA nephropathy, nephrosclerosis, diabetic nephropathy, heredity Renal disease, myocardial fibrosis, heart failure, restenosis after PTCA, arteriosclerosis, myelofibrosis, rheumatoid arthritis, post-inflammation hyperplasia, postoperative scar or burn scar, atopic dermatitis, hypertrophic scar In uterine fibroids, benign prostatic hyperplasia, scleroderma, Alzheimer's disease, sclerosing peritonitis, diabetic retinopathy, type I diabetes, the tissue is fibrotic due to excessive accumulation of extracellular matrix such as collagen and fibronectin. As a result, the function of organs / tissues decreases and scar formation occurs. Such excessive accumulation of the extracellular matrix is induced by increased production of the extracellular matrix based on the breakdown of the balance between biosynthesis and degradation of the extracellular matrix. In fact, in fibrotic tissues, the expression level of extracellular matrix genes such as collagen genes (particularly type I collagen, type III collagen, type IV collagen), fibronectin gene, laminin gene, proteoglycan gene, etc. has increased. Has been observed (for example, see Non-Patent Documents 1 to 6).
In fibrotic tissues, it has also been observed that the amount of TGF-β, which is a kind of cytokine, is increased (for example, see Non-Patent Documents 1 and 2). It has been suggested that TGF-β increases the expression level of extracellular matrix genes and is involved in the enhancement of extracellular matrix protein production and, consequently, tissue fibrosis (for example, Non-Patent Documents 1 and 7). reference). Furthermore, it has been clarified that administration of anti-TGF-β antibody and soluble TGF-β receptor to tissue fibrosis model animals improves tissue fibrosis and accompanyingly improves tissue function. (For example, see Non-Patent Documents 8 to 10), and by administering a compound that acts to suppress the intracellular signal transduction of TGF-β, tissue fibrosis is improved. It is also known to be improved (for example, see Non-Patent Documents 11 to 13).
On the other hand, heart fibrosis in a hypertensive state is one of the causes of heart failure such as left ventricular diastolic failure and renal failure such as diabetic nephropathy and nephrosclerosis.

Ｊ．Ｉｎｖｅｓｔ．Ｄｅｒｍａｔｏｌ．，９４，３６５，（１９９０）J. et al. Invest. Dermatol. , 94, 365, (1990) Ｐｒｏｃ．Ｎａｔｌ．Ａｃａｄ．Ｓｃｉ．ＵＳＡ，８８，６６４２，（１９９１）Proc. Natl. Acad. Sci. USA, 88, 6642, (1991) Ｊ．Ａｍ．Ｓｏｃ．Ｎｅｐｈｒｏｌ．，１５，２６３７，（２００４）J. et al. Am. Soc. Nephrol. , 15, 2637, (2004) Ｃａｒｄｉｏｖａｓｃ．Ｐａｔｈｏｌ．，１３，１１９，（２００４）Cardiovasc. Pathol. , 13, 119, (2004) Ｃｌｉｎ．Ｎｅｐｈｒｏｌ．，４４，２１１，(１９９５)Clin. Nephrol. , 44, 211, (1995) Ｊ．Ｈｅｐａｔｏｌ．，２９，２６３，（１９９８）J. et al. Hepatol. , 29, 263 (1998) Ｌａｂ．Ｉｎｖｅｓｔ．，６３，１７１，（１９９０）Lab. Invest. , 63, 171, (1990) Ｄｉａｂｅｔｅｓ，４５，５２２−５３０，（１９９６）Diabetes, 45, 522-530, (1996) Ｐｒｏｃ．Ｎａｔｌ．Ａｃａｄ．Ｓｃｉ．ＵＳＡ，９６，１２７１９−１２７２４，（１９９９）Proc. Natl. Acad. Sci. USA, 96, 12719-12724, (1999) Ｐｒｏｃ．Ｎａｔｌ．Ａｃａｄ．Ｓｃｉ．ＵＳＡ，９７，８０１５−８０２０，（２０００）］Proc. Natl. Acad. Sci. USA, 97, 8015-8020, (2000)] Ａｕｔｏｉｍｍｕｎｉｔｙ，３５，２７７−２８２，（２００２）Autoimmunity, 35, 277-282, (2002) Ｊ．Ｈｅｐａｔｏｌ．，３７，３３１−３３９，（２００２）J. et al. Hepatol. , 37, 331-339, (2002) ＬｉｆｅＳｃｉ．，７１，１５５９−１６０６，（２００２）］Life Sci. , 71, 1559-1606, (2002)]

そこで、組織における細胞外マトリックス遺伝子の発現量を減少させ、細胞外マトリックス蓄積量を低下させることにより、組織の線維化を改善させる薬剤（即ち、細胞外マトリックス蓄積抑制剤や、線維症治療剤又は心不全治療剤）の開発・提供が切望されている。 Therefore, an agent that improves tissue fibrosis by decreasing the amount of extracellular matrix gene expression in the tissue and reducing the amount of extracellular matrix accumulation (ie, an agent for inhibiting extracellular matrix accumulation, a therapeutic agent for fibrosis, or The development and provision of therapeutic agents for heart failure) are eagerly desired.

本発明者らは、かかる状況の下、鋭意検討した結果、下記の式（Ｉ）〜（VI）（I'）、（II'）及び（V'）で示される化合物が細胞外マトリックス遺伝子の転写を抑制する能力を有することを見出し、本発明に至った。
即ち、本発明は、
１．式（I）

［式中、
Ｉ．αは、芳香族５員環又は窒素原子を２以上有する芳香族６員環を表し、（Ｙ_α）_ｑにおいて、Ｙ_αは、下記のＸ_０群又はＹ_０群の基を表し、ｑは、０、１、２又は３を表して、ｑが２以上のとき、Ｙ_αは同一又は相異なり、ｑが２以上のとき、隣接している２個の同一又は相異なるＹ_αは、Ｚ_０群の基をなしてα環と縮環してもよく、（Ｘ_α）_ｐにおいて、Ｘ_αは、下記のＸ_０群、Ｙ_０群及びＺ_０群に属さない置換基を表し、ｐは、０、１、２又は３を表し、ｐが２以上のとき、Ｘ_αは同一又は相異なり、ｐとｑとの和は３以下である。
(１)Ｘ_０群：Ｍ_ａ−基［Ｍ_ａは、Ｒ_ｂ−基（Ｒ_ｂは、ハロゲン原子で置換されてもよいC1-C10アルキル基を表す。）、ハロゲン原子、ニトロ基、シアノ基、水酸基、Ｒ_ｃ−Ｂ_ａ−Ｒ_ｄ−基（Ｒ_ｃは、ハロゲン原子で置換されてもよいC1-C10アルキル基を表し、Ｂ_ａは、オキシ基、チオ基、スルフィニル基又はスルホニル基を表し、Ｒ_ｄは、単結合又はC1-C10アルキレン基を表す。）、ＨＯＲ_ｄ−基（Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅ−ＣＯ−Ｒ_ｄ−基（Ｒ_ｅは、水素原子、又は、ハロゲン原子で置換されてもよいC1-C10アルキル基を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅ−ＣＯ−Ｏ−Ｒ_ｄ−基（Ｒ_ｅ及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＯ−ＣＯ−Ｒ_ｄ−基（Ｒ_ｅ及びＲ_ｄは、前記と同一の意味を表す。）、ＨＯ−ＣＯ−ＣＨ＝ＣＨ−基、Ｒ_ｅＲ_ｅ’Ｎ−Ｒ_ｄ−基（Ｒ_ｅ及びＲ_ｅ’は、同一又は相異なり、Ｒ_ｅは、前記と同一の意味を表し、Ｒ_ｅ’は、Ｒ_ｅと同一の意味を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅ−ＣＯ−ＮＲ_ｅ’−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｂＯ−ＣＯ−Ｎ（Ｒ_ｅ）−Ｒ_ｄ−基（Ｒ_ｂ、Ｒ _ｅ及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ_ｅ’Ｎ−ＣＯ−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ_ｅ’Ｎ−ＣＯ−ＮＲ_ｅ’’−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、同一又は相異なり、Ｒ_ｅ及びＲ_ｅ’は、前記と同一の意味を表し、Ｒ_ｅ’’は、Ｒ_ｅと同一の意味を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ_ｅ’Ｎ−Ｃ（＝ＮＲ_ｅ’’）−ＮＲ_ｅ’’’−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’、Ｒ_ｅ’’及びＲ_ｅ’’’は、同一又は相異なり、Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、前記と同一の意味を表し、Ｒ_ｅ’’’は、Ｒ_ｅと同一の意味を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｂ−ＳＯ_２−ＮＲ_ｅ−Ｒ_ｄ−基（Ｒ_ｂ、Ｒ_ｅ及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ _ｅ’Ｎ−ＳＯ_２−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｄは、前記と同一の意味を表す。）、C2-C10アルケニル基又はC2-C10アルキニル基を表す。］である。
(２)Ｙ_０群：Ｍ_ｂ０−Ｒ_ｄ−基［Ｍ_ｂ０は、Ｍ_ｃ０−基｛Ｍ_ｃ０は、Ｍ_ｄ０−Ｒ_ｄ’−基｛Ｍ_ｄ０は、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよい６−１０員環のアリール基、又は、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよい５−１０員環のヘテロアリール基、又は、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよい不飽和結合を含んでもよい３−１０員環の炭化水素環若しくは複素環をなす基、又は、

(ｂ_０) −基（（ｂ_０）において、Ｇ_０は、置換基を有してもよい、飽和又は不飽和の、非芳香族の、５〜１４員の炭化水素環又は複素環をなす。）、

（ｃ_０）−基（（ｃ_０）において、Ｊ_０は、窒素原子を含んでもよく、芳香族５−７員環をなす。）、

（ｄ_０）−基｛ｄ_０は、カルボニル基又はチオカルボニル基で置換され、更に、オキシ基、チオ基、−ＮＲ_１-基｛Ｒ_１は、水素原子、又は、C1-C10アルキル基、又は、ハロゲン原子若しくはＲ_２−Ｂ_１−基（Ｒ_２は、C1-C10アルキル基、C3-C10アルケニル基又はC3-C10アルキニル基を表し、Ｂ_１は、オキシ基、チオ基、スルフィニル基又はスルホニル基を表す。）で置換されたC2-C10アルキル基、又は、C3-C10アルケニル基、又は、C3-C10アルキニル基を表す。｝、スルフィニル基若しくはスルホニル基で置換されてもよい５−１２員の炭化水素環をなす。｝又は

（ｅ_０）−基｛ｅ_０は、カルボニル基、チオカルボニル基、オキシ基、チオ基、−ＮＲ_１-基（Ｒ_１は、前記と同一の意味を表す。）、スルフィニル基若しくはスルホニル基で置換されてもよい５−１２員の炭化水素環をなす。｝を表し、Ｒ_ｄ’は、Ｒ_ｄと同一又は相異なり、Ｒ_ｄと同一の意味を表す。｝を表す。｝、Ｍ_ｃ０−Ｂ_ａ−基（Ｍ_ｃ０及びＢ_ａは、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−Ｏ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｏ−ＣＯ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｏ−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−ＣＯ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−ＣＯ−ＮＲ_ｅ’−基（Ｍ_ｃ０、Ｒ_ｅ及びＲ_ｅ’は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−Ｃ（＝ＮＲ_ｅ’）−ＮＲ_ｅ’’−基（Ｍ_ｃ０、Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、前記と同一の意味を表す。）、Ｍ_ｃ０−ＳＯ_２−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）又はＭ_ｃ０Ｒ_ｅＮ−ＳＯ_２−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）を表し、Ｒ_ｄは、前記と同一の意味を表す。］である。
(３)Ｚ_０群：ハロゲン原子、C1-C10アルコキシ基、C3-C10アルケニルオキシ基、C3-C10アルキニルオキシ基、カルボニル基、チオカルボニル基、オキシ基、チオ基、スルフィニル基若しくはスルホニル基を有してもよい、５−１２員環の炭化水素環又は複素環であって、芳香族又は非芳香族の、単環又は縮環であって、α環と縮環する基である。
ＩＩ．βは、
式（I-1）

［式中、
(１)Ｑ_αは、置換されてもよい水酸基、又は、置換されてもよいアミノ基を表す。
(２)Ｗ_αは、酸素原子又は−ＮＴ_α−基（Ｔ_αは、水素原子、又は、窒素原子上の置換基を表す。）を表す。
(３)Ｋ_α及びＬ_αは、同一又は相異なり、水素原子、又は、炭素原子上の置換基を表し、Ｋ_αとＬ_αとは、置換基を有してもよいC3-C10アルキレン基又は置換基を有してもよいC4-C10アルケニレン基をなすことがある。］
で示される基、
式（I-2）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｌ_βは水酸基又はメチル基を表す。]
で示される基、
式（I-3）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｌ_γは、C1-C10アルキル基を表す。]
で示される基、
式（I-4）

[式中、Ｔ_αは、前記と同一の意味を表す。]
で示される基、
式（I-5）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｋ_βは、シアノ基又はＵＯＣＯ−基（Ｕは、水素原子又はC1-C10アルキル基を表す。）を表す。]
で示される基、
式（I-6）

[式中、Ｗ_αは、前記と同一の意味を表し、Ｋ_γとＬ_δとは、置換基を有してもよいC3-C10アルキレン基又は置換基を有してもよいC4-C10アルケニレン基をなす。]
で示される基、
式（I-7）

[式中、Ｑ_α及びＷ_αは、前記と同一の意味を表し、Ｋ_δとＬ_εとは、−Ｖ_α＝Ｖ_α’−Ｖ_α’’＝Ｖ_α’’’−基（Ｖ_α、Ｖ_α’、Ｖ_α’’及びＶ_α’’’は、同一又は相異なり、置換されてもよいメチン基、又は、−Ｎ＝基を表し、Ｖ_α、Ｖ_α’、Ｖ_α’’及びＶ_α’’’のうち少なくとも一つは−Ｎ＝基を表す。）をなす。]
で示される基、
式（I-8）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｑ_βは、置換されてもよい水酸基を表す。]
で示される基、又は、
式（I-9）

[式中、Ｕ及びＷ_αは、前記と同一の意味を表す。]
で示される基を表す。
尚、複数の置換基の間での同一記号における「前記と同一の意味を表す」とは、当該複数の置換基が互いに独立しながら前記と同一の意味を表すことを示し、当該複数の置換基の間では、選ばれる置換基の選択肢の範囲が同一であるが、その範囲内で選ばれる限り当該選ばれる置換基は同じであっても、異なっていてもよいことを意味するものである。］
で示されるシンナモイル化合物と不活性担体とを含有することを特徴とする細胞外マトリックス遺伝子転写抑制組成物。
２．式（II）

（ｅ_０）−基｛ｅ_０は、カルボニル基、チオカルボニル基、オキシ基、チオ基、−ＮＲ_１-基（Ｒ_１は、前記と同一の意味を表す。）、スルフィニル基若しくはスルホニル基で置換されてもよい５−１２員の炭化水素環をなす。｝を表し、Ｒ_ｄ’は、Ｒ_ｄと同一又は相異なり、Ｒ_ｄと同一の意味を表す。｝を表す。｝、Ｍ_ｃ０−Ｂ_ａ−基（Ｍ_ｃ０及びＢ_ａは、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−Ｏ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｏ−ＣＯ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｏ−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−ＣＯ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−ＣＯ−ＮＲ_ｅ’−基（Ｍ_ｃ０、Ｒ_ｅ及びＲ_ｅ’は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−Ｃ（＝ＮＲ_ｅ’）−ＮＲ_ｅ’’−基（Ｍ_ｃ０、Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、前記と同一の意味を表す。）、Ｍ_ｃ０−ＳＯ_２−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）又はＭ_ｃ０Ｒ_ｅＮ−ＳＯ_２−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）を表し、Ｒ_ｄは、前記と同一の意味を表す。］である。
(３)Ｚ_０群：ハロゲン原子、C1-C10アルコキシ基、C3-C10アルケニルオキシ基、C3-C10アルキニルオキシ基、カルボニル基、チオカルボニル基、オキシ基、チオ基、スルフィニル基若しくはスルホニル基を有してもよい、５−１２員環の炭化水素環又は複素環であって、芳香族又は非芳香族の、単環又は縮環であって、α環と縮環する基である。
ＩＩ．βは、
式（II-1）

［式中、
(１)Ｑ_αは、置換されてもよい水酸基、又は、置換されてもよいアミノ基を表す。
(２)Ｗ_αは、酸素原子又は−ＮＴ_α−基（Ｔ_αは、水素原子、又は、窒素原子上の置換基を表す。）を表す。
(３)Ｋ_α及びＬ_αは、同一又は相異なり、水素原子、又は、炭素原子上の置換基を表し、Ｋ_αとＬ_αとは、置換基を有してもよいC3-C10アルキレン基又は置換基を有してもよいC4-C10アルケニレン基をなすことがある。］
で示される基、
式（II-2）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｌ_βは水酸基又はメチル基を表す。]
で示される基、
式（II-3）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｌ_γは、C1-C10アルキル基を表す。]
で示される基、
式（II-4）

[式中、Ｔ_αは、前記と同一の意味を表す。]
で示される基、
式（II-5）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｋ_βは、シアノ基又はＵＯＣＯ−基（Ｕは、水素原子又はC1-C10アルキル基を表す。）を表す。]
で示される基、
式（II-6）

[式中、Ｗ_αは、前記と同一の意味を表し、Ｋ_γとＬ_δとは、置換基を有してもよいC3-C10アルキレン基又は置換基を有してもよいC4-C10アルケニレン基をなす。]
で示される基、
式（II-7）

[式中、Ｑ_α及びＷ_αは、前記と同一の意味を表し、Ｋ_δとＬ_εとは、−Ｖ_α＝Ｖ_α’−Ｖ_α’’＝Ｖ_α’’’−基（Ｖ_α、Ｖ_α’、Ｖ_α’’及びＶ_α’’’は、同一又は相異なり、置換されてもよいメチン基、又は、−Ｎ＝基を表し、Ｖ_α、Ｖ_α’、Ｖ_α’’及びＶ_α’’’のうち少なくとも一つは−Ｎ＝基を表す。）をなす。]
で示される基、
式（II-8）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｑ_βは、置換されてもよい水酸基を表す。]
で示される基、又は、
式（II-9）

[式中、Ｕ及びＷ_αは、前記と同一の意味を表す。]
で示される基を表す。
但し、αがフラン環又はチオフェン環のとき、ｐ及びｑが同時に０になることはない。
尚、複数の置換基の間での同一記号における「前記と同一の意味を表す」とは、当該複数の置換基が互いに独立しながら前記と同一の意味を表すことを示し、当該複数の置換基の間では、選ばれる置換基の選択肢の範囲が同一であるが、その範囲内で選ばれる限り当該選ばれる置換基は同じであっても、異なっていてもよいことを意味するものである。］
で示されるシンナモイル化合物。
３．式（III）

［式中、
Ｉ．Ａ０は、芳香族５員環又は窒素原子を２以上有する芳香族６員環を表す。
ＩＩ．（Ｘ_Ａ０）_ｐにおいて、Ｘ_Ａ０は、下記のＡ_０群からＮ_０群までのいずれかの群に含まれる基を表し、ｐは、０、１、２又は３を表し、ｐが２以上のとき、Ｘ_Ａ０は、同一又は相異なる。
(１)Ａ_０群：Ｄ_１−Ｒ_４−基［Ｄ_１は、（Ｒ_１−（Ｏ）_ｋ−）Ａ_１Ｎ−（Ｏ）_ｋ’−基｛Ｒ_１は、水素原子、又は、C1-C10アルキル基、又は、ハロゲン原子若しくはＲ_２−Ｂ_１−基（Ｒ_２は、C1-C10アルキル基、C3-C10アルケニル基又はC3-C10アルキニル基を表し、Ｂ_１は、オキシ基、チオ基、スルフィニル基又はスルホニル基を表す。）で置換されたC2-C10アルキル基、又は、C3-C10アルケニル基、又は、C3-C10アルキニル基を表し、ｋは、０又は１を表し、Ａ_１は、Ｒ_３−（ＣＨＲ_０）_ｍ−（Ｂ_２−Ｂ_３）_ｍ’−基｛Ｒ_３は、水素原子、又は、ハロゲン原子若しくはＲ_２−Ｂ_１−基（Ｒ_２及びＢ_１は、前記と同一の意味を表す。）で置換されてもよいC1-C10アルキル基、又は、C2-C10アルケニル基、又は、C2-C10アルキニル基を表し、Ｒ_０は、水素原子、C1-C10アルキル基又はC2-C10ハロアルキル基を表し、ｍは、０又は１を表し、Ｂ_２は、単結合、オキシ基、チオ基又は−Ｎ（（Ｏ）_ｎＲ_１’）−基（Ｒ_１’は、Ｒ_１と同一又は相異なり、Ｒ_１と同一の意味を表し、ｎは、０又は１を表す。）を表し、Ｂ_３は、カルボニル基、チオカルボニル基又はスルホニル基を表し、ｍ’は、０又は１を表し、Ｂ_３がスルホニル基のとき、ｍは０となりかつＲ_３が水素原子となることはない。｝を表し、ｋ’は、０又は１を表す。｝を表し、Ｒ_４は、C1-C10アルキレン基を表す。但し、Ｒ_０’Ｒ_０ ’’Ｎ−Ｒ_４−基（Ｒ_０’及びＲ_０’’は、Ｒ_０と同一又は相異なり、Ｒ_０と同一の意味を表し、Ｒ_４は、前記と同一の意味を表す。）を除く。］、Ｄ_２−Ｒ_４−基［Ｄ_２は、シアノ基、Ｒ_１Ｒ_１’ＮＣ（＝Ｎ−（Ｏ）_ｎ−Ａ_１）−基（Ｒ_１、Ｒ_１’、ｎ、及びＡ_１は、前記と同一の意味を表す。）、Ａ_１Ｎ＝Ｃ（−ＯＲ_２）−基（Ａ_１及びＲ_２は、前記と同一の意味を表す。）又はＮＨ_２−ＣＳ−基を表し、Ｒ_４は前記と同一の意味を表す。］、Ｄ_３−Ｒ_４−基｛Ｄ_３は、ニトロ基又はＲ_１ＯＳＯ_２−基（Ｒ_１は、前記と同一の意味を表す。）を表し、Ｒ_４は、前記と同一の意味を表す。｝又はＲ_１ＯＳＯ_２−基（Ｒ_１は、前記と同一の意味を表す。）である。
(２)Ｂ_０群：

（ａ_０）−基
（（ａ_０）において、Ｅ_０は、置換基を有してもよい、飽和又は不飽和の、芳香族又は非芳香族の、５〜１４員の炭化水素環又は複素環をなし、Ｒ_１は、前記と同一の意味を表す。）である。
(３)Ｃ_０群：ハロゲン原子、Ｒ_２−Ｂ_１−基（Ｒ_２及びＢ_１は、前記と同一の意味を表す。）、Ｄ_４−Ｒ_４−基［Ｄ_４は、水酸基又はＡ_１−Ｏ−基（Ａ_１は、前記と同一の意味を表す。）を表し、Ｒ_４は前記と同一の意味を表す。］、Ｄ_５−基［Ｄ_５は、Ｏ＝Ｃ（Ｒ_３）−基（Ｒ_３は、前記と同一の意味を表す。）、Ａ_１−（Ｏ）_ｎ−Ｎ＝Ｃ（Ｒ_３）−基（Ａ_１、ｎ及びＲ_３は、前記と同一の意味を表す。）、Ｒ_１−Ｂ_０−ＣＯ−Ｒ_４−（Ｏ）_ｎ−Ｎ＝Ｃ（Ｒ_３）−基｛Ｒ_１、Ｒ_４、ｎ及びＲ_３は、前記と同一の意味を表し、Ｂ_０は、オキシ基、チオ基又は−Ｎ（（Ｏ）_ｍＲ_１’）−基（Ｒ_１’及びｍは、前記と同一の意味を表す。）を表す。｝、Ｄ_２−Ｒ_４−（Ｏ）_ｎ−Ｎ＝Ｃ（Ｒ_３）−基（Ｄ_２、Ｒ_４、ｎ及びＲ_３は、前記と同一の意味を表す。）又はＲ_１Ａ_１Ｎ−Ｎ＝Ｃ（Ｒ_３）−基（Ｒ_１、Ａ_１及びＲ_３は、前記と同一の意味を表す。）を表す。］、Ｒ_１Ａ_１Ｎ−Ｏ−Ｒ_４−基（Ｒ_１、Ａ_１及びＲ_４は、前記と同一の意味を表す。）、Ｒ_１（Ａ_１−（Ｏ）_ｎ−）Ｎ−基（Ｒ_１、Ａ_１及びｎは、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）又はＤ_３−基（Ｄ_３は、前記と同一の意味を表す。）で置換されたC2-C10アルケニル基
である。
(４)Ｄ_０群：

(ｂ_０) −Ｒ_４−基（（ｂ_０）において、Ｇ_０は、置換基を有してもよい、飽和又は不飽和の、非芳香族の、５〜１４員の炭化水素環又は複素環をなす。）、

（ｃ_０）−Ｒ_４−基
（（ｃ_０）において、Ｊ_０は、窒素原子を含んでもよく、芳香族５−７員環をなし、Ｒ_４は、前記と同一の意味を表す。）、ハロゲン原子、Ｒ_２−Ｂ_１−Ｒ_４−基（Ｒ_２、Ｂ_１及びＲ_４は、前記と同一の意味を表す。）、Ｄ_４−Ｒ_４−基（Ｄ_４及びＲ_４は、前記と同一の意味を表す。）、Ｄ_５−基（Ｄ_５は、前記と同一の意味を表す。）、Ｄ_１−Ｒ_４−基（Ｄ_１及びＲ_４は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）又はＤ_３−Ｒ_４−基（Ｄ_３及びＲ_４は、前記と同一の意味を表す。）で置換されたC2-C10アルキニル基
である。
(５)Ｅ_０群：Ａ_２−ＣＯ−Ｒ_５−基
である。但し、Ａ_２が水酸基のとき、Ｒ_５がビニレン基ではない。
[Ａ_２は、
(i)Ａ_３−Ｂ_４−基
｛Ａ_３は、水素原子、又は、C1-C10アルキル基、又は、C2-C10ハロアルキル基、又は、ハロゲン原子で置換されてもよいC2-C10アルケニル基、又は、ハロゲン原子で置換されてもよいC3-C10アルキニル基、又は、Ｒ_ａ０−（Ｒ_４）_ｍ−基（Ｒ_ａ０は、置換されてもよい５−７員環のアリール基又はヘテロアリール基を表し、Ｒ_４及びｍは前記と同一の意味を表す。）、又は、（ｂ_０）−Ｒ_４−基（（ｂ_０）及びＲ_４は、前記と同一の意味を表す。）、（ｃ_０）−Ｒ_４−基（（ｃ_０）及びＲ_４は、前記と同一の意味を表す。）、Ｒ_２−Ｂ_１−Ｒ_４−基（Ｒ_２、Ｂ_１及びＲ_４は、前記と同一の意味を表す。）、Ｄ_４−Ｒ_４−基（Ｄ_４及びＲ_４は、前記と同一の意味を表す。）、Ｄ_５−基（Ｄ_５は、前記と同一の意味を表す。）、Ｄ_１−Ｒ_４−基（Ｄ_１及びＲ_４は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）、Ｄ_３−Ｒ_４−基（Ｄ_３及びＲ_４は、前記と同一の意味を表す。）若しくはＡ_４−ＳＯ_２−Ｒ_４−基｛Ａ_４は、（ｂ_０）−基（（ｂ_０）は、前記と同一の意味を表す。）、（ｃ_０）−基（（ｃ_０）は、前記と同一の意味を表す。）又はＲ_１Ｒ_１’Ｎ−基（Ｒ_１及びＲ_１’は、前記と同一の意味を表す。）を表し、Ｒ_４は、前記と同一の意味を表す。｝で置換されたC1-C10アルキル基を表し、
Ｂ_４は、オキシ基、チオ基又は−Ｎ（（Ｏ）_ｍＲ_１）−基（Ｒ_１及びｍは、前記と同一の意味を表す。）を表す。但し、Ｂ_４がチオ基のとき、Ａ_３が水素原子ではない。｝、
(ii)Ｒ_１−Ｂ_４−ＣＯ−Ｒ_４−Ｂ_４’−基（Ｒ_１、Ｂ_４及びＲ_４は、前記と同一の意味を表し、Ｂ_４’は、Ｂ_４と同一又は相異なり、Ｂ_４と同一の意味を表す。但し、Ｂ_４がチオ基のとき、Ｒ_２が水素原子ではない。）又はＤ_２−Ｒ_４−Ｂ_４−基（Ｄ_２、Ｒ_４及びＢ_４は、前記と同一の意味を表す。）、
(iii)Ｒ_２−ＳＯ_２−ＮＲ_１−基（Ｒ_２は、前記と同一の意味を表す。但し、水素原子を除く。Ｒ_１は、前記と同一の意味を表す。）、
(iv)（ｂ_０）−基（（ｂ_０）は、前記と同一の意味を表す。）、
(v)（ｃ_０）−基（（ｃ_０）は、前記と同一の意味を表す。）又は
(vi)Ｒ_１Ａ_１Ｎ−ＮＲ_１’−基（Ｒ_１、Ａ_１及びＲ_１’は、前記と同一の意味を表す。）を表し、Ｒ_５は、ハロゲン原子で置換されてもよいC2-C10アルケニレン基、又は、C2-C10アルキニレン基を表す。］
（６）Ｆ_０群：Ａ_５−Ｂ_５−Ｒ_６−基［Ａ_５は、Ｄ_４−基（Ｄ_４は、前記と同一の意味を表す。）、Ｄ_１−基（Ｄ_１は、前記と同一の意味を表す。）、Ｄ_３−基（Ｄ_３は、前記と同一の意味を表す。）若しくはＡ_４−ＳＯ_２−基（Ａ_４は、前記と同一の意味を表す。）で置換されたC2-C10アルキル基、又は、Ｒ_２−Ｂ_１−基（Ｒ_２及びＢ_１は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）、Ｄ_５−基（Ｄ_５は、前記と同一の意味を表す。）若しくはＡ_２−ＣＯ−基（Ａ_２は、前記と同一の意味を表す。）で置換されたC1-C10アルキル基を表し、Ｂ_５は、Ｂ_１−基（Ｂ_１は、前記と同一の意味を表す。）又は−ＮＡ_１−基（Ａ_１は、前記と同一の意味を表す。）を表し、Ｒ_６は、単結合又はC1-C10アルキレン基を表す。］
である。
（７）Ｇ_０群：Ａ_６−Ｂ_５−Ｒ_６−基
［Ａ_６は、（ａ_０）−Ｒ_４−基（（ａ_０）及びＲ_４は、前記と同一の意味を表す。）、又は、C2-C10アルケニル基、又は、C2-C10アルキニル基、又は、ハロゲン原子、Ｒ_２−Ｂ_１−基（Ｒ_２及びＢ_１は、前記と同一の意味を表す。）、Ｄ_５−基（Ｄ_５は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）若しくはＡ_２−ＣＯ−基（Ａ_２は、前記と同一の意味を表す。）で置換されたC2-C10アルケニル基、又は、ハロゲン原子、Ｒ_２−Ｂ_１−基（Ｒ_２及びＢ_１は、前記と同一の意味を表す。）、Ｄ_５−基（Ｄ_５は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）若しくはＡ_２−ＣＯ−基（Ａ_２は、前記と同一の意味を表す。）で置換されたC2-C10アルキニル基、又は、（ｂ_０）−基（（ｂ_０）は、前記と同一の意味を表す。）、（ｃ_０）−基（（ｃ_０）は、前記と同一の意味を表す。）、Ｄ_４−基（Ｄ_４は、前記と同一の意味を表す。）、Ｄ_１−基（Ｄ_１は、前記と同一の意味を表す。）若しくはＤ_３−基（Ｄ_３は、前記と同一の意味を表す。）で置換されたC3-C10アルケニル基、又は、Ｄ_４−基（Ｄ_４は、前記と同一の意味を表す。）、Ｄ_１−基（Ｄ_１は、前記と同一の意味を表す。）若しくはＤ_３−基（Ｄ_３は、前記と同一の意味を表す。）で置換されたC3-C10アルキニル基を表し、Ｂ_５及びＲ_６は、前記と同一の意味を表す。］
である。
（８）Ｈ_０群：
Ｄ_２−Ｎ（−（Ｏ）_ｎ−Ａ_１）−Ｒ_６−基（Ｄ_２、ｎ、Ａ_１及びＲ_６は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。但し、シアノ基を除く。）、Ｒ_１（Ｒ_１’（Ｏ）_ｎ）Ｎ−ＣＲ_１’’＝Ｎ−Ｒ_６−基（Ｒ_１、Ｒ_１’、ｎ及びＲ_６は、前記と同一の意味を表し、Ｒ_１’’は、Ｒ_１と同一又は相異なり、Ｒ_１と同一の意味を表す。）、Ｒ_１−（Ｏ）_ｎ−Ｎ＝ＣＲ_１’−ＮＲ_２−Ｒ_６−基（Ｒ_１、ｎ、Ｒ_１’、Ｒ_２及びＲ_６は、前記と同一の意味を表す。）、Ｒ_２−Ｂ_３−ＮＲ_１−ＣＯ−ＮＲ_１’−Ｒ_６−基（Ｒ_２、Ｂ_３、Ｒ_１、Ｒ_１’及びＲ_６は、前記と同一の意味を表す。）、Ｄ_２−ＣＯ−ＮＲ_１−Ｒ_６−基（Ｄ_２、Ｒ_１及びＲ_６は、前記と同一の意味を表す。）又はＡ_２−ＣＯＣＯ−ＮＲ_１−Ｒ_６−基（Ａ_２、Ｒ_１及びＲ_６は、前記と同一の意味を表す。）
である。
(９)Ｉ_０群：
Ａ_７−Ｂ_６−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_７は、ハロゲン原子で置換されてもよいC2-C10アルケニル基、C2-C10アルキニル基、C3-C10ハロアルキニル基、Ｒ_２−Ｂ_１−Ｒ_４−基（Ｒ_２、Ｂ_１及びＲ_４は、前記と同一の意味を表す。）、Ｄ_４−Ｒ_４−基（Ｄ_４及びＲ_４は、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−基（Ｄ_５及びＲ_４は、前記と同一の意味を表す。）、Ｄ_１−Ｒ_４−基（Ｄ_１及びＲ_４は、前記と同一の意味を表す。）、（ｂ_０）−Ｒ_４−基（（ｂ_０）及びＲ_４は、前記と同一の意味を表す。）、（ｃ_０）−Ｒ_４−基（（ｃ_０）及びＲ_４は、前記と同一の意味を表す。）、Ｄ_２−Ｒ_４−基（Ｄ_２及びＲ_４は、前記と同一の意味を表す。）、Ｄ_３−Ｒ_４−基（Ｄ_３及びＲ_４は、前記と同一の意味を表す。）、Ａ_４−ＳＯ_２−Ｒ_４−基（Ａ_４及びＲ_４は、前記と同一の意味を表す。）又はＡ_２−ＣＯ−Ｒ_４−基（Ａ_２及びＲ_４は、前記と同一の意味を表す。）を表し、Ｂ_６は、カルボニル基又はチオカルボニル基を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］、Ａ_８−ＣＳ−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_８は、水素原子、又は、ハロゲン原子で置換されてもよいC1-C10アルキル基を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］、
Ａ_７’−Ｂ_２’−Ｂ_３−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_７’は、ハロゲン原子で置換されてもよいC3-C10アルケニル基、ハロゲン原子で置換されてもよいC3-C10アルキニル基、Ｒ_２−Ｂ_１−Ｒ_４’−基（Ｒ_２及びＢ_１は、前記と同一の意味を表し、Ｒ_４’は、C2-C10アルキレン基を表す。）、Ｄ_４−Ｒ_４’−基（Ｄ_４及びＲ_４’は、前記と同一の意味を表す。）、Ｄ_１−Ｒ_４’−基（Ｄ_１及びＲ_４’は、前記と同一の意味を表す。）、（ｂ_０）−Ｒ_４’−基（（ｂ_０）及びＲ_４’は、前記と同一の意味を表す。）、（ｃ_０）−Ｒ_４’−基（（ｃ_０）及びＲ_４’は、前記と同一の意味を表す。）、Ｄ_２−Ｒ_４−基（Ｄ_２及びＲ_４は、前記と同一の意味を表す。）、Ｄ_３−Ｒ_４’−基（Ｄ_３及びＲ_４’は、前記と同一の意味を表す。）又はＡ_２−ＣＯ−Ｒ_４−基（Ａ_２及びＲ_４は、前記と同一の意味を表す。）を表し、Ｂ_２’は、オキシ基、チオ基又は−Ｎ（（Ｏ）_ｎ’Ｒ_１’）−基（ｎ’は、ｎと同一又は相異なり、ｎと同一の意味を表し、Ｒ_１’は、前記と同一の意味を表す。）を表し、Ｂ_３、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］、Ａ_８’−Ｂ_２’−ＣＳ−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_８’は、C1-C10アルキル基又はC2-C10ハロアルキル基を表し、Ｂ_２’は、前記と同一の意味を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］、Ａ_８’−Ｓ−Ｂ_３’−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_８’、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表し、Ｂ_３’は、カルボニル基又はスルホニル基を表す。］又はＡ_７’’−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_７’’は、C2-C10アルケニル基、ハロゲン原子で置換されたC3-C10アルケニル基、ハロゲン原子で置換されてもよいC3-C10アルキニル基、Ｒ_２−Ｂ_１−Ｒ_４’−基（Ｒ_２、Ｂ_１及びＲ_４’は、前記と同一の意味を表す。）、Ｄ_４−Ｒ_４’−基（Ｄ_４及びＲ_４’は、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−基（Ｄ_５及びＲ_４は、前記と同一の意味を表す。）、Ｄ_１−Ｒ_４’−基（Ｄ_１及びＲ_４’は、前記と同一の意味を表す。）、（ｂ_０）−Ｒ_４’−基（（ｂ_０）及びＲ_４’は、前記と同一の意味を表す。）、（ｃ_０）−Ｒ_４’−基（（ｃ_０）及びＲ_４’は、前記と同一の意味を表す。）、Ｄ_２−Ｒ_４−基（Ｄ_２及びＲ_４は、前記と同一の意味を表す。）、ＮＯ_２−Ｒ_４−基（Ｒ_４は、前記と同一の意味を表す。）又はＡ_２−ＣＯ−Ｒ_４−基（Ａ_２及びＲ_４は、前記と同一の意味を表す。）を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］
である。
(１０)Ｊ_０群：Ａ_７−ＣＯ−基（Ａ_７は、前記と同一の意味を表す。）、又は、Ａ_９−ＣＳ−基（Ａ_９は、Ａ_７又はＡ_８を表す。）、又は、Ａ_９’（Ｏ）_ｍＮ＝Ｃ（Ａ_９）−基（Ａ_９’は、Ａ_７’又はＡ_８’を表し、ｍ及びＡ_９は、前記と同一の意味を表す。）、又は、Ｄ_２−ＣＯ−基（Ｄ_２は、前記と同一の意味を表す。）、又は、Ａ_２−ＣＯＣＯ−基（Ａ_２は、前記と同一の意味を表す。）、又は、Ａ_９−ＣＯ−Ｂ_１’−Ｒ_６−基（Ａ_９及びＲ_６は、前記と同一の意味を表し、Ｂ_１’は、オキシ基又はチオ基を表す。但し、Ｂ_１’がオキシ基のとき、Ａ_９は、Ａ_８ではない。）、又は、Ａ_９−ＣＳ−Ｂ_１’−Ｒ_６−基（Ａ_９、Ｂ_１’及びＲ_６は、は、前記と同一の意味を表す。）、又は、Ａ_７’’−ＳＯ_２−Ｂ_１’−Ｒ_６−基（Ａ_７’’、Ｂ_１’及びＲ_６は、は、前記と同一の意味を表す。）、又は、Ａ_８−ＳＯ_２−Ｂ_１’−Ｒ_６−基（Ａ_８、Ｂ_１’及びＲ_６は、は、前記と同一の意味を表す。但し、Ａ_８は、水素原子となることはない。）、又は、Ａ_９’−Ｂ_２’−Ｂ_３−Ｂ_１’−Ｒ_６−基（Ａ_９’、Ｂ_２’、Ｂ_３、Ｂ_１’及びＲ_６は、は、前記と同一の意味を表す。）、又は、（ｂ_０）−基（（ｂ_０）は、前記と同一の意味を表す。）若しくは（ｃ_０）−基（（ｃ_０）は、前記と同一の意味を表す。）で置換されたC2-C10アルケニル基
である。
（１１）Ｋ_０群：Ａ_１０−Ｎ（（Ｏ）_ｎＲ_１）−ＣＯ−Ｒ_６−基［Ａ_１０は、水素原子（但し、ｎは０ではない。）、Ａ_７’’−ＳＯ_２−基（Ａ_７’’は、前記と同一の意味を表す。）、Ａ_８−ＳＯ_２−基（Ａ_８は、前記と同一の意味を表す。但し、Ａ_８は、水素原子とはならない。）、Ａ_９’Ｏ−基（Ａ_９’は、前記と同一の意味を表す。但し、ｎは１ではない。）、Ａ_９’−基（Ａ_９’は、前記と同一の意味を表す。但し、ｎが０のとき、Ａ_８’を除く。）、Ｒ_２ＯＣＨ_２−基（Ｒ_２は、前記と同一の意味を表す。）、Ａ_２−ＣＯ−Ｒ_４−基（Ａ_２及びＲ_４は、前記と同一の意味を表す。）又はＡ_２−ＣＯ−ＣＨ（ＣＨ_２ＣＯ−Ａ_２）−基（Ａ_２は、前記と同一の意味を表す。）を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］
である。
（１２）Ｌ_０群：Ａ_１０’−Ｎ（（Ｏ）_ｎＲ_１）−ＳＯ_２−Ｒ_６−基［Ａ_１０’は、水素原子（但し、ｎは０ではない。）、Ａ_９’Ｏ−基（Ａ_９’は、前記と同一の意味を表す。但し、ｎは１ではない。）、Ａ_９’−基（Ａ_９’は、前記と同一の意味を表す。但し、ｎが０のとき、Ａ_８’を除く。）、Ｒ_２−ＣＯ−基（Ｒ_２は、前記と同一の意味を表す。）、Ａ_２−ＣＯ−Ｒ_４−基（Ａ_２及びＲ_４は、前記と同一の意味を表す。）又はＡ_２−ＣＯ−ＣＨ（ＣＨ_２ＣＯ−Ａ_２）−基（Ａ_２は、前記と同一の意味を表す。）を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］、Ａ_９’’Ｒ_１Ｎ−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ_１’）−Ｒ_６−基［Ａ_９’’は、水素原子又はＡ_９’−基（Ａ_９’は、前記と同一の意味を表す。）を表し、Ｒ_１、ｎ、Ｒ_１’及びＲ_６は、前記と同一の意味を表す。］又は（ｂ_０）−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ_１’）−Ｒ_６−基［（ｂ_０）、ｎ、Ｒ_１’及びＲ_６は、前記と同一の意味を表す。］
である。
（１３）Ｍ_０群：Ｒ_１（Ｒ_２Ｓ）Ｃ＝Ｎ−Ｒ_６−基（Ｒ_１、Ｒ_２及びＲ_６は、前記と同一の意味を表す。）、Ｒ_２Ｂ（Ｒ_２’Ｂ’）Ｃ＝Ｎ−Ｒ_６−基（Ｒ_２及びＲ_６は、前記と同一の意味を表し、Ｒ_２’は、Ｒ_２と同一又は相異なり、Ｒ_２と、同一の意味を表し、Ｂ及びＢ’は、同一又は相異なり、オキシ基又はチオ基を表す。）、Ｒ_１Ｒ_１’Ｎ−（Ｒ_２Ｓ）Ｃ＝Ｎ−Ｒ_６−基（Ｒ_１、Ｒ_１’、Ｒ_２及びＲ_６は、前記と同一の意味を表す。）、Ｒ_１Ｎ＝Ｃ（ＳＲ_２）−ＮＲ_２’−Ｒ_６−基（Ｒ_１、Ｒ_２、Ｒ_２’及びＲ_６は、前記と同一の意味を表す。）又はＲ_１（Ｒ_１’Ｏ）Ｎ−Ｒ_６−基（Ｒ_１、Ｒ_１’及びＲ_６は、前記と同一の意味を表す。）
である。
（１４）Ｎ_０群：Ａ_１１−Ｐ（＝Ｏ）（ＯＲ_１’）−Ｒ_４−基［Ａ_１１は、Ｒ_１−基（Ｒ_１は、前記と同一の意味を表す。）、Ｒ_１Ｏ−Ｒ_６−基（Ｒ_１及びＲ_６は、前記と同一の意味を表す。）又はＲ_１ＯＣＯ−ＣＨＲ_０−基（Ｒ_１及びＲ_０は、前記と同一の意味を表す。）を表し、Ｒ_１’及びＲ_４は、前記と同一の意味を表す。］
である。
ＩＩＩ．（Ｙ_Ａ０）_ｑにおいて、Ｙ_Ａ０は、下記のＸ_０群及びＹ_０群の基を表し、ｑは、０、１、２又は３を表し、ｐ（ｐは、前記と同一の意味を表す。）とｑとの和は３以下であり、ｑが２以上のとき、Ｙ_Ａ０は同一又は相異なり、ｑが２以上のとき、隣接している２個の同一又は相異なるＹ_Ａ０は、Ｚ_０群の基をなして、Ａ０環と縮環してもよい。
(１)Ｘ_０群：
Ｍ_ａ−基［Ｍ_ａは、Ｒ_ｂ−基（Ｒ_ｂは、ハロゲン原子で置換されてもよいC1-C10アルキル基を表す。）、ハロゲン原子、ニトロ基、シアノ基、水酸基、Ｒ_ｃ−Ｂ_ａ−Ｒ_ｄ−基（Ｒ_ｃは、ハロゲン原子で置換されてもよいC1-C10アルキル基を表し、Ｂ_ａは、オキシ基、チオ基、スルフィニル基又はスルホニル基を表し、Ｒ_ｄは、単結合又はC1-C10アルキレン基を表す。）、ＨＯＲ_ｄ−基（Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅ−ＣＯ−Ｒ_ｄ−基（Ｒ_ｅは、水素原子、又は、ハロゲン原子で置換されてもよいC1-C10アルキル基を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅ−ＣＯ−Ｏ−Ｒ_ｄ−基（Ｒ_ｅ及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＯ−ＣＯ−Ｒ_ｄ−基（Ｒ_ｅ及びＲ_ｄは、前記と同一の意味を表す。）、ＨＯ−ＣＯ−ＣＨ＝ＣＨ−基、Ｒ_ｅＲ_ｅ’Ｎ−Ｒ_ｄ−基（Ｒ_ｅ及びＲ_ｅ’は、同一又は相異なり、Ｒ_ｅは、前記と同一の意味を表し、Ｒ_ｅ’は、Ｒ_ｅと同一の意味を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅ−ＣＯ−ＮＲ_ｅ’−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｂＯ−ＣＯ−Ｎ（Ｒ_ｅ）−Ｒ_ｄ−基（Ｒ_ｂ、Ｒ _ｅ及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ_ｅ’Ｎ−ＣＯ−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ_ｅ’Ｎ−ＣＯ−ＮＲ_ｅ’’−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、同一又は相異なり、Ｒ_ｅ及びＲ_ｅ’は、前記と同一の意味を表し、Ｒ_ｅ’’は、Ｒ_ｅと同一の意味を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ_ｅ’Ｎ−Ｃ（＝ＮＲ_ｅ’’）−ＮＲ_ｅ’’’−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’、Ｒ_ｅ’’及びＲ_ｅ’’’は、同一又は相異なり、Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、前記と同一の意味を表し、Ｒ_ｅ’’’は、Ｒ_ｅと同一の意味を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｂ−ＳＯ_２−ＮＲ_ｅ−Ｒ_ｄ−基（Ｒ_ｂ、Ｒ_ｅ及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ _ｅ’Ｎ−ＳＯ_２−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｄは、前記と同一の意味を表す。）、C2-C10アルケニル基又はC2-C10アルキニル基を表す。］である。
(２)Ｙ_０群：
Ｍ_ｂ０−Ｒ_ｄ−基［Ｍ_ｂ０は、Ｍ_ｃ０−基｛Ｍ_ｃ０は、Ｍ_ｄ０−Ｒ_ｄ’−基｛Ｍ_ｄ０は、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよい６−１０員環のアリール基、又は、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよい５−１０員環のヘテロアリール基、又は、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよい不飽和結合を含んでもよい３−１０員環の炭化水素環若しくは複素環をなす基、又は、

(ｂ_０) −基（（ｂ_０）は、前記と同一の意味を表す。）、

（ｃ_０）−基（（ｃ_０）は、前記と同一の意味を表す。）、

（ｄ_０）−基｛ｄ_０は、カルボニル基又はチオカルボニル基で置換され、更に、オキシ基、チオ基、−ＮＲ_１-基（Ｒ_１は、前記と同一の意味を表す。）、スルフィニル基若しくはスルホニル基で置換されてもよい５−１２員の炭化水素環をなす。｝又は

（ｅ_０）−基｛ｅ_０は、カルボニル基、チオカルボニル基、オキシ基、チオ基、−ＮＲ_１-基（Ｒ_１は、前記と同一の意味を表す。）、スルフィニル基若しくはスルホニル基で置換されてもよい５−１２員の炭化水素環をなす。｝を表し、Ｒ_ｄ’は、Ｒ_ｄと同一又は相異なり、Ｒ_ｄと同一の意味を表す。｝を表す。｝、Ｍ_ｃ０−Ｂ_ａ−基（Ｍ_ｃ０及びＢ_ａは、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−Ｏ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｏ−ＣＯ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｏ−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−ＣＯ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−ＣＯ−ＮＲ_ｅ’−基（Ｍ_ｃ０、Ｒ_ｅ及びＲ_ｅ’は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−Ｃ（＝ＮＲ_ｅ’）−ＮＲ_ｅ’’−基（Ｍ_ｃ０、Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、前記と同一の意味を表す。）、Ｍ_ｃ０−ＳＯ_２−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）又はＭ_ｃ０Ｒ_ｅＮ−ＳＯ_２−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）を表し、Ｒ_ｄは、前記と同一の意味を表す。］である。
(３)Ｚ_０群：ハロゲン原子、C1-C10アルコキシ基、C3-C10アルケニルオキシ基、C3-C10アルキニルオキシ基、カルボニル基、チオカルボニル基、オキシ基、チオ基、スルフィニル基若しくはスルホニル基を有してもよい、５−１２員環の炭化水素環又は複素環であって、芳香族又は非芳香族の、単環又は縮環であって、Ａ０環と縮環する基である。
ＩＶ．Ｂ０は、
式（III-1）

［式中、
(１)Ｑ_Ａ０は、水酸基、（ｂ_０）−基（（ｂ_０）は、前記と同一の意味を表す。）、Ａ_９−Ｂ_６−Ｂ_ｃ−基［Ａ_９及びＢ_６は、前記と同一の意味を表し、Ｂ_ｃは、オキシ基又は−Ｎ（（Ｏ）_ｍＲ_１）−基（ｍ及びＲ_１は、前記と同一の意味を表す。）を表す。但し、Ａ_９が水素原子のとき、Ｂ_ｃは、スルホニル基ではない。］、Ａ_７’’−ＳＯ_２−Ｂ_ｃ−基（Ａ_７’’及びＢ_ｃは、前記と同一の意味を表す。）、Ａ_８−ＳＯ_２−Ｂ_ｃ−基（Ａ_８及びＢ_ｃは、前記と同一の意味を表す。但し、Ａ_８は水素原子とはならない。）、Ｒ_１Ｒ_１’Ｎ−ＳＯ_２−Ｂ_ｃ−基（Ｒ_１、Ｒ_１’及びＢ_ｃは、前記と同一の意味を表す。）、（ｂ_０）−ＳＯ_２−Ｂ_ｃ−基（（ｂ_０）及びＢ_ｃは、前記と同一の意味を表す。）、Ａ_９’−Ｂ_ｃ−基（Ａ_９’及びＢ_ｃは、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−Ｂ_ｃ−基（Ｄ_５、Ｒ_４及びＢ_ｃは、前記と同一の意味を表す。）、Ｍ_ｃ０−Ｂ_３−Ｂ_ｃ−基（Ｍ_ｃ０、Ｂ_３及びＢ_ｃは、前記と同一の意味を表す。）又はＭ_ｃ０−Ｂ_ｃ−基（Ｍ_ｃ０及びＢ_ｃは、前記と同一の意味を表す。）を表す。
（２）Ｗ_Ａ０は、酸素原子又は−ＮＴ_Ａ０−基［Ｔ_Ａ０は、水素原子、Ａ_９’−基（Ａ_９’は、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−基（Ｄ_５及びＲ_４は、前記と同一の意味を表す。）又はＭ_ｃ０−基（Ｍ_ｃ０は、前記と同一の意味を表す。）を表す。］を表す。
（３）Ｋ_Ａ０は、水素原子、ハロゲン原子又はC1-C10アルキル基を表し、Ｌ_Ａ０は、水素原子、C1-C10アルキル基又はＭ_ｂ０−基（Ｍ_ｂ０は、前記と同一の意味を表す。）を表し、Ｋ_Ａ０とＬ_Ａ０とは、C3-C10アルキレン基、又は、単数又は同一又は相異なる複数のＭａ−基（Ｍａは、前記と同一の意味を表す。）で置換されてもよいC4-C10アルケニレン基をなすことがある。］
で示される基、
式（III-2）

[式中、Ｔ_Ａ０は、前記と同一の意味を表し、Ｌ_Ｂ０は水酸基又はメチル基を表す。]
で示される基、
式（III-3）

[式中、Ｔ_Ａ０は、前記と同一の意味を表し、Ｌ_Ｃ０は、C1-C10アルキル基を表す。]
で示される基、
式（III-4）

[式中、Ｔ_Ａ０は、前記と同一の意味を表す。]
で示される基、
式（III-5）

[式中、Ｔ_Ａ０は、前記と同一の意味を表し、Ｋ_Ｂ０は、シアノ基又はＵＯＣＯ−基（Ｕは、水素原子又はC1-C10アルキル基を表す。）を表す。]
で示される基、
式（III-6）

[式中、Ｗ_Ａ０は、前記と同一の意味を表し、Ｋ_Ｃ０とＬ_Ｄ０とは、C3-C10アルキレン基又は単数又は同一又は相異なる複数のＭａ−基（Ｍａは、前記と同一の意味を表す。）で置換されてもよいC4-C10アルケニレン基をなす。]
で示される基、
式（III-7）

[式中、Ｑ_Ａ０及びＷ_Ａ０は、前記と同一の意味を表し、Ｋ_Ｄ０とＬ_Ｅ０とは、−Ｖ_Ａ０＝Ｖ_Ａ０’−Ｖ_Ａ０’’＝Ｖ_Ａ０’’’−基｛Ｖ_Ａ０、Ｖ_Ａ０’、Ｖ_Ａ０’’及びＶ_Ａ０’’’は、同一又は相異なり、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよいメチン基、又は、−Ｎ＝基を表し、Ｖ_Ａ０、Ｖ_Ａ０’、Ｖ_Ａ０’’及びＶ_Ａ０’’’のうち少なくとも一つは−Ｎ＝基を表す。｝をなす。]
で示される基、
式（III-8）

[式中、Ｔ_Ａ０は、前記と同一の意味を表し、Ｑ_Ｂ０は、水酸基、Ａ_９−Ｂ_６−Ｏ−基［Ａ_９及びＢ_６は、前記と同一の意味を表す。］、Ａ_７’’−ＳＯ_２−Ｏ−基（Ａ_７’’は、前記と同一の意味を表す。）、Ａ_８−ＳＯ_２−Ｏ−基（Ａ_８は、前記と同一の意味を表す。但し、Ａ_８は水素原子とはならない。）、Ｒ_１Ｒ_１’Ｎ−ＳＯ_２−Ｏ−基（Ｒ_１及びＲ_１’は、前記と同一の意味を表す。）、（ｂ_０）−ＳＯ_２−Ｏ−基（（ｂ_０）は、前記と同一の意味を表す。）、Ａ_９’−Ｏ−基（Ａ_９’は、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−Ｏ−基（Ｄ_５及びＲ_４は、前記と同一の意味を表す。）、Ｍ_ｃ０−Ｂ_３−Ｏ−基（Ｍ_ｃ０及びＢ_３は、前記と同一の意味を表す。）又はＭ_ｃ０−Ｏ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）を表す。]
で示される基、又は、
式（III-9）

[式中、Ｕ及びＷ_Ａ０は、前記と同一の意味を表す。]
で示される基を表す。
但し、Ａ０がフラン環又はチオフェン環のとき、ｐ及びｑが同時に０になることはない。
尚、複数の置換基の間での同一記号における「前記と同一の意味を表す」とは、当該複数の置換基が互いに独立しながら前記と同一の意味を表すことを示し、当該複数の置換基の間では、選ばれる置換基の選択肢の範囲が同一であるが、その範囲内で選ばれる限り当該選ばれる置換基は同じであっても、異なっていてもよいことを意味するものである。］
で示されるシンナモイル化合物。
４．式（IV）

［式中、
Ｉ．Ａは、芳香族５員環又は窒素原子を２以上有する芳香族６員環を表す。
ＩＩ．（Ｘ_Ａ）_ｐにおいて、Ｘ_Ａは、下記のＡ群からＮ群までのいずれかの群に含まれる基を表し、ｐは、０、１、２又は３を表し、ｐが２以上のとき、Ｘ_Ａは、同一又は相異なる。
(１)Ａ群：Ｄ_１−Ｒ_４−基［Ｄ_１は、（Ｒ_１−（Ｏ）_ｋ−）Ａ_１Ｎ−（Ｏ）_ｋ’−基｛Ｒ_１は、水素原子、又は、C1-C10アルキル基、又は、ハロゲン原子若しくはＲ_２−Ｂ_１−基（Ｒ_２は、C1-C10アルキル基、C3-C10アルケニル基又はC3-C10アルキニル基を表し、Ｂ_１は、オキシ基、チオ基、スルフィニル基又はスルホニル基を表す。）で置換されたC2-C10アルキル基、又は、C3-C10アルケニル基、又は、C3-C10アルキニル基を表し、ｋは、０又は１を表し、Ａ_１は、Ｒ_３−（ＣＨＲ_０）_ｍ−（Ｂ_２−Ｂ_３）_ｍ’−基｛Ｒ_３は、水素原子、又は、ハロゲン原子若しくはＲ_２−Ｂ_１−基（Ｒ_２及びＢ_１は、前記と同一の意味を表す。）で置換されてもよいC1-C10アルキル基、又は、C2-C10アルケニル基、又は、C2-C10アルキニル基を表し、Ｒ_０は、水素原子、C1-C10アルキル基又はC2-C10ハロアルキル基を表し、ｍは、０又は１を表し、Ｂ_２は、単結合、オキシ基、チオ基又は−Ｎ（（Ｏ）_ｎＲ_１’）−基（Ｒ_１’は、Ｒ_１と同一又は相異なり、Ｒ_１と同一の意味を表し、ｎは、０又は１を表す。）を表し、Ｂ_３は、カルボニル基、チオカルボニル基又はスルホニル基を表し、ｍ’は、０又は１を表し、Ｂ_３がスルホニル基のとき、ｍは０となりかつＲ_３が水素原子となることはない。｝を表し、ｋ’は、０又は１を表す。｝を表し、Ｒ_４は、C1-C10アルキレン基を表す。但し、Ｒ_０’Ｒ_０ ’’Ｎ−Ｒ_４−基（Ｒ_０’及びＲ_０’’は、Ｒ_０と同一又は相異なり、Ｒ_０と同一の意味を表し、Ｒ_４は、前記と同一の意味を表す。）を除く。］、Ｄ_２−Ｒ_４−基［Ｄ_２は、シアノ基、Ｒ_１Ｒ_１’ＮＣ（＝Ｎ−（Ｏ）_ｎ−Ａ_１）−基（Ｒ_１、Ｒ_１’、ｎ、及びＡ_１は、前記と同一の意味を表す。）、Ａ_１Ｎ＝Ｃ（−ＯＲ_２）−基（Ａ_１及びＲ_２は、前記と同一の意味を表す。）又はＮＨ_２−ＣＳ−基を表し、Ｒ_４は前記と同一の意味を表す。］、Ｄ_３−Ｒ_４−基｛Ｄ_３は、ニトロ基又はＲ_１ＯＳＯ_２−基（Ｒ_１は、前記と同一の意味を表す。）を表し、Ｒ_４は、前記と同一の意味を表す。｝又はＲ_１ＯＳＯ_２−基（Ｒ_１は、前記と同一の意味を表す。）である。
(２)Ｂ群：

（ａ）−基
［（ａ）において、Ｅ_１及びＥ_１’は、C1-C10アルキル基若しくはC1-C10アルコキシ基で置換されてもよいメチレン基、又は、カルボニル基を表す。但し、Ｅ_１及びＥ_１’は、同時にカルボニル基となることはない。Ｅ_２は、オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１’−基（Ｒ_１’は、前記と同一の意味を表す。）で置換されてもよいC2-C10アルキレン基、又は、オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１’−基（Ｒ_１’は、前記と同一の意味を表す。）で置換されてもよいC3-C10アルケニレン基を表し、Ｒ_１は、前記と同一の意味を表す。］
である。
(３)Ｃ群：ハロゲン原子、Ｒ_２−Ｂ_１−基（Ｒ_２及びＢ_１は、前記と同一の意味を表す。）、Ｄ_４−Ｒ_４−基［Ｄ_４は、水酸基又はＡ_１−Ｏ−基（Ａ_１は、前記と同一の意味を表す。）を表し、Ｒ_４は前記と同一の意味を表す。］、Ｄ_５−基［Ｄ_５は、Ｏ＝Ｃ（Ｒ_３）−基（Ｒ_３は、前記と同一の意味を表す。）、Ａ_１−（Ｏ）_ｎ−Ｎ＝Ｃ（Ｒ_３）−基（Ａ_１、ｎ及びＲ_３は、前記と同一の意味を表す。）、Ｒ_１−Ｂ_０−ＣＯ−Ｒ_４−（Ｏ）_ｎ−Ｎ＝Ｃ（Ｒ_３）−基｛Ｒ_１、Ｒ_４、ｎ及びＲ_３は、前記と同一の意味を表し、Ｂ_０は、オキシ基、チオ基又は−Ｎ（（Ｏ）_ｍＲ_１’）−基（Ｒ_１’及びｍは、前記と同一の意味を表す。）を表す。｝、Ｄ_２−Ｒ_４−（Ｏ）_ｎ−Ｎ＝Ｃ（Ｒ_３）−基（Ｄ_２、Ｒ_４、ｎ及びＲ_３は、前記と同一の意味を表す。）又はＲ_１Ａ_１Ｎ−Ｎ＝Ｃ（Ｒ_３）−基（Ｒ_１、Ａ_１及びＲ_３は、前記と同一の意味を表す。）を表す。］、Ｒ_１Ａ_１Ｎ−Ｏ−Ｒ_４−基（Ｒ_１、Ａ_１及びＲ_４は、前記と同一の意味を表す。）、Ｒ_１（Ａ_１−（Ｏ）_ｎ−）Ｎ−基（Ｒ_１、Ａ_１及びｎは、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）又はＤ_３−基（Ｄ_３は、前記と同一の意味を表す。）で置換されたC2-C10アルケニル基
である。
(４)Ｄ群：

(ｂ) −Ｒ_４−基［（ｂ）において、Ｇ_１、Ｇ_２、Ｇ_４及びＧ_５は、隣接原子と単結合で結ばれた、メチル基で置換されてもよいメチレン基、又は、隣接原子と二重結合で結ばれた、メチル基で置換されてもよいメチン基を表し、Ｇ_３は、単結合、又は、二重結合、又は、メチル基、オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１−基（Ｒ_１は、前記と同一の意味を表す。）で置換されてもよいC1-C10アルキレン基、又は、メチル基、オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１−基（Ｒ_１は、前記と同一の意味を表す。）で置換されてもよいC2-C10アルケニレン基を表し、Ｒ_４は、前記と同一の意味を表す。］、

（ｃ）−Ｒ_４−基
（（ｃ）において、Ｊ_１、Ｊ_２及びＪ_３は、同一又は相異なり、メチル基で置換されてもよいメチン基、又は、窒素原子を表し、Ｒ_４は、前記と同一の意味を表す。）、ハロゲン原子、Ｒ_２−Ｂ_１−Ｒ_４−基（Ｒ_２、Ｂ_１及びＲ_４は、前記と同一の意味を表す。）、Ｄ_４−Ｒ_４−基（Ｄ_４及びＲ_４は、前記と同一の意味を表す。）、Ｄ_５−基（Ｄ_５は、前記と同一の意味を表す。）、Ｄ_１−Ｒ_４−基（Ｄ_１及びＲ_４は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）又はＤ_３−Ｒ_４−基（Ｄ_３及びＲ_４は、前記と同一の意味を表す。）で置換されたC2-C10アルキニル基
である。
(５)Ｅ群：Ａ_２−ＣＯ−Ｒ_５−基
である。但し、Ａ_２が水酸基のとき、Ｒ_５がビニレン基ではない。
[Ａ_２は、
(i)Ａ_３−Ｂ_４−基
｛Ａ_３は、水素原子、又は、C1-C10アルキル基、又は、C2-C10ハロアルキル基、又は、ハロゲン原子で置換されてもよいC2-C10アルケニル基、又は、ハロゲン原子で置換されてもよいC3-C10アルキニル基、又は、Ｒ_ａ−（Ｒ_４）_ｍ−基（Ｒ_ａは、ハロゲン原子、C1-C10アルキル基、C1-C10アルコキシ基若しくはニトロ基で置換されてもよい、フェニル基、ピリジル基、フリル基若しくはチエニル基を表し、Ｒ_４及びｍは前記と同一の意味を表す。）、又は、（ｂ）−Ｒ_４−基（（ｂ）及びＲ_４は、前記と同一の意味を表す。）、（ｃ）−Ｒ_４−基（（ｃ）及びＲ_４は、前記と同一の意味を表す。）、Ｒ_２−Ｂ_１−Ｒ_４−基（Ｒ_２、Ｂ_１及びＲ_４は、前記と同一の意味を表す。）、Ｄ_４−Ｒ_４−基（Ｄ_４及びＲ_４は、前記と同一の意味を表す。）、Ｄ_５−基（Ｄ_５は、前記と同一の意味を表す。）、Ｄ_１−Ｒ_４−基（Ｄ_１及びＲ_４は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）、Ｄ_３−Ｒ_４−基（Ｄ_３及びＲ_４は、前記と同一の意味を表す。）若しくはＡ_４−ＳＯ_２−Ｒ_４−基｛Ａ_４は、（ｂ）−基（（ｂ）は、前記と同一の意味を表す。）、（ｃ）−基（（ｃ）は、前記と同一の意味を表す。）又はＲ_１Ｒ_１’Ｎ−基（Ｒ_１及びＲ_１’は、前記と同一の意味を表す。）を表し、Ｒ_４は、前記と同一の意味を表す。｝で置換されたC1-C10アルキル基を表し、
Ｂ_４は、オキシ基、チオ基又は−Ｎ（（Ｏ）_ｍＲ_１）−基（Ｒ_１及びｍは、前記と同一の意味を表す。）を表す。但し、Ｂ_４がチオ基のとき、Ａ_３が水素原子ではない。｝、
(ii)Ｒ_１−Ｂ_４−ＣＯ−Ｒ_４−Ｂ_４’−基（Ｒ_１、Ｂ_４及びＲ_４は、前記と同一の意味を表し、Ｂ_４’は、Ｂ_４と同一又は相異なり、Ｂ_４と同一の意味を表す。但し、Ｂ_４がチオ基のとき、Ｒ_２が水素原子ではない。）又はＤ_２−Ｒ_４−Ｂ_４−基（Ｄ_２、Ｒ_４及びＢ_４は、前記と同一の意味を表す。）、
(iii)Ｒ_２−ＳＯ_２−ＮＲ_１−基（Ｒ_２は、前記と同一の意味を表す。但し、水素原子を除く。Ｒ_１は、前記と同一の意味を表す。）、
(iv)（ｂ）−基（（ｂ）は、前記と同一の意味を表す。）、
(v)（ｃ）−基（（ｃ）は、前記と同一の意味を表す。）又は
(vi)Ｒ_１Ａ_１Ｎ−ＮＲ_１’−基（Ｒ_１、Ａ_１及びＲ_１’は、前記と同一の意味を表す。）を表し、Ｒ_５は、ハロゲン原子で置換されてもよいC2-C10アルケニレン基、又は、C2-C10アルキニレン基を表す。］
（６）Ｆ群：Ａ_５−Ｂ_５−Ｒ_６−基［Ａ_５は、Ｄ_４−基（Ｄ_４は、前記と同一の意味を表す。）、Ｄ_１−基（Ｄ_１は、前記と同一の意味を表す。）、Ｄ_３−基（Ｄ_３は、前記と同一の意味を表す。）若しくはＡ_４−ＳＯ_２−基（Ａ_４は、前記と同一の意味を表す。）で置換されたC2-C10アルキル基、又は、Ｒ_２−Ｂ_１−基（Ｒ_２及びＢ_１は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）、Ｄ_５−基（Ｄ_５は、前記と同一の意味を表す。）若しくはＡ_２−ＣＯ−基（Ａ_２は、前記と同一の意味を表す。）で置換されたC1-C10アルキル基を表し、Ｂ_５は、Ｂ_１−基（Ｂ_１は、前記と同一の意味を表す。）又は−ＮＡ_１−基（Ａ_１は、前記と同一の意味を表す。）を表し、Ｒ_６は、単結合又はC1-C10アルキレン基を表す。］
である。
（７）Ｇ群：Ａ_６−Ｂ_５−Ｒ_６−基
［Ａ_６は、（ａ）−Ｒ_４−基（（ａ）及びＲ_４は、前記と同一の意味を表す。）、又は、C2-C10アルケニル基、又は、C2-C10アルキニル基、又は、ハロゲン原子、Ｒ_２−Ｂ_１−基（Ｒ_２及びＢ_１は、前記と同一の意味を表す。）、Ｄ_５−基（Ｄ_５は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）若しくはＡ_２−ＣＯ−基（Ａ_２は、前記と同一の意味を表す。）で置換されたC2-C10アルケニル基、又は、ハロゲン原子、Ｒ_２−Ｂ_１−基（Ｒ_２及びＢ_１は、前記と同一の意味を表す。）、Ｄ_５−基（Ｄ_５は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。）若しくはＡ_２−ＣＯ−基（Ａ_２は、前記と同一の意味を表す。）で置換されたC2-C10アルキニル基、又は、（ｂ）−基（（ｂ）は、前記と同一の意味を表す。）、（ｃ）−基（（ｃ）は、前記と同一の意味を表す。）、Ｄ_４−基（Ｄ_４は、前記と同一の意味を表す。）、Ｄ_１−基（Ｄ_１は、前記と同一の意味を表す。）若しくはＤ_３−基（Ｄ_３は、前記と同一の意味を表す。）で置換されたC3-C10アルケニル基、又は、Ｄ_４−基（Ｄ_４は、前記と同一の意味を表す。）、Ｄ_１−基（Ｄ_１は、前記と同一の意味を表す。）若しくはＤ_３−基（Ｄ_３は、前記と同一の意味を表す。）で置換されたC3-C10アルキニル基を表し、Ｂ_５及びＲ_６は、前記と同一の意味を表す。］
である。
（８）Ｈ群：
Ｄ_２−Ｎ（−（Ｏ）_ｎ−Ａ_１）−Ｒ_６−基（Ｄ_２、ｎ、Ａ_１及びＲ_６は、前記と同一の意味を表す。）、Ｄ_２−基（Ｄ_２は、前記と同一の意味を表す。但し、シアノ基を除く。）、Ｒ_１（Ｒ_１’（Ｏ）_ｎ）Ｎ−ＣＲ_１’’＝Ｎ−Ｒ_６−基（Ｒ_１、Ｒ_１’、ｎ及びＲ_６は、前記と同一の意味を表し、Ｒ_１’’は、Ｒ_１と同一又は相異なり、Ｒ_１と同一の意味を表す。）、Ｒ_１−（Ｏ）_ｎ−Ｎ＝ＣＲ_１’−ＮＲ_２−Ｒ_６−基（Ｒ_１、ｎ、Ｒ_１’、Ｒ_２及びＲ_６は、前記と同一の意味を表す。）、Ｒ_２−Ｂ_３−ＮＲ_１−ＣＯ−ＮＲ_１’−Ｒ_６−基（Ｒ_２、Ｂ_３、Ｒ_１、Ｒ_１’及びＲ_６は、前記と同一の意味を表す。）、Ｄ_２−ＣＯ−ＮＲ_１−Ｒ_６−基（Ｄ_２、Ｒ_１及びＲ_６は、前記と同一の意味を表す。）又はＡ_２−ＣＯＣＯ−ＮＲ_１−Ｒ_６−基（Ａ_２、Ｒ_１及びＲ_６は、前記と同一の意味を表す。）
である。
(９)Ｉ群：
Ａ_７−Ｂ_６−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_７は、ハロゲン原子で置換されてもよいC2-C10アルケニル基、C2-C10アルキニル基、C3-C10ハロアルキニル基、Ｒ_２−Ｂ_１−Ｒ_４−基（Ｒ_２、Ｂ_１及びＲ_４は、前記と同一の意味を表す。）、Ｄ_４−Ｒ_４−基（Ｄ_４及びＲ_４は、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−基（Ｄ_５及びＲ_４は、前記と同一の意味を表す。）、Ｄ_１−Ｒ_４−基（Ｄ_１及びＲ_４は、前記と同一の意味を表す。）、（ｂ）−Ｒ_４−基（（ｂ）及びＲ_４は、前記と同一の意味を表す。）、（ｃ）−Ｒ_４−基（（ｃ）及びＲ_４は、前記と同一の意味を表す。）、Ｄ_２−Ｒ_４−基（Ｄ_２及びＲ_４は、前記と同一の意味を表す。）、Ｄ_３−Ｒ_４−基（Ｄ_３及びＲ_４は、前記と同一の意味を表す。）、Ａ_４−ＳＯ_２−Ｒ_４−基（Ａ_４及びＲ_４は、前記と同一の意味を表す。）又はＡ_２−ＣＯ−Ｒ_４−基（Ａ_２及びＲ_４は、前記と同一の意味を表す。）を表し、Ｂ_６は、カルボニル基又はチオカルボニル基を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］、Ａ_８−ＣＳ−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_８は、水素原子、又は、ハロゲン原子で置換されてもよいC1-C10アルキル基を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］、
Ａ_７’−Ｂ_２’−Ｂ_３−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_７’は、ハロゲン原子で置換されてもよいC3-C10アルケニル基、ハロゲン原子で置換されてもよいC3-C10アルキニル基、Ｒ_２−Ｂ_１−Ｒ_４’−基（Ｒ_２及びＢ_１は、前記と同一の意味を表し、Ｒ_４’は、C2-C10アルキレン基を表す。）、Ｄ_４−Ｒ_４’−基（Ｄ_４及びＲ_４’は、前記と同一の意味を表す。）、Ｄ_１−Ｒ_４’−基（Ｄ_１及びＲ_４’は、前記と同一の意味を表す。）、（ｂ）−Ｒ_４’−基（（ｂ）及びＲ_４’は、前記と同一の意味を表す。）、（ｃ）−Ｒ_４’−基（（ｃ）及びＲ_４’は、前記と同一の意味を表す。）、Ｄ_２−Ｒ_４−基（Ｄ_２及びＲ_４は、前記と同一の意味を表す。）、Ｄ_３−Ｒ_４’−基（Ｄ_３及びＲ_４’は、前記と同一の意味を表す。）又はＡ_２−ＣＯ−Ｒ_４−基（Ａ_２及びＲ_４は、前記と同一の意味を表す。）を表し、Ｂ_２’は、オキシ基、チオ基又は−Ｎ（（Ｏ）_ｎ’Ｒ_１’）−基（ｎ’は、ｎと同一又は相異なり、ｎと同一の意味を表し、Ｒ_１’は、前記と同一の意味を表す。）を表し、Ｂ_３、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］、Ａ_８’−Ｂ_２’−ＣＳ−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_８’は、C1-C10アルキル基又はC2-C10ハロアルキル基を表し、Ｂ_２’は、前記と同一の意味を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］、Ａ_８’−Ｓ−Ｂ_３’−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_８’、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表し、Ｂ_３’は、カルボニル基又はスルホニル基を表す。］又はＡ_７’’−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ_７’’は、C2-C10アルケニル基、ハロゲン原子で置換されたC3-C10アルケニル基、ハロゲン原子で置換されてもよいC3-C10アルキニル基、Ｒ_２−Ｂ_１−Ｒ_４’−基（Ｒ_２、Ｂ_１及びＲ_４’は、前記と同一の意味を表す。）、Ｄ_４−Ｒ_４’−基（Ｄ_４及びＲ_４’は、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−基（Ｄ_５及びＲ_４は、前記と同一の意味を表す。）、Ｄ_１−Ｒ_４’−基（Ｄ_１及びＲ_４’は、前記と同一の意味を表す。）、（ｂ）−Ｒ_４’−基（（ｂ）及びＲ_４’は、前記と同一の意味を表す。）、（ｃ）−Ｒ_４’−基（（ｃ）及びＲ_４’は、前記と同一の意味を表す。）、Ｄ_２−Ｒ_４−基（Ｄ_２及びＲ_４は、前記と同一の意味を表す。）、ＮＯ_２−Ｒ_４−基（Ｒ_４は、前記と同一の意味を表す。）又はＡ_２−ＣＯ−Ｒ_４−基（Ａ_２及びＲ_４は、前記と同一の意味を表す。）を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］
である。
(１０)Ｊ群：Ａ_７−ＣＯ−基（Ａ_７は、前記と同一の意味を表す。）、又は、Ａ_９−ＣＳ−基（Ａ_９は、Ａ_７又はＡ_８を表す。）、又は、Ａ_９’（Ｏ）_ｍＮ＝Ｃ（Ａ_９）−基（Ａ_９’は、Ａ_７’又はＡ_８’を表し、ｍ及びＡ_９は、前記と同一の意味を表す。）、又は、Ｄ_２−ＣＯ−基（Ｄ_２は、前記と同一の意味を表す。）、又は、Ａ_２−ＣＯＣＯ−基（Ａ_２は、前記と同一の意味を表す。）、又は、Ａ_９−ＣＯ−Ｂ_１’−Ｒ_６−基（Ａ_９及びＲ_６は、前記と同一の意味を表し、Ｂ_１’は、オキシ基又はチオ基を表す。但し、Ｂ_１’がオキシ基のとき、Ａ_９は、Ａ_８ではない。）、又は、Ａ_９−ＣＳ−Ｂ_１’−Ｒ_６−基（Ａ_９、Ｂ_１’及びＲ_６は、は、前記と同一の意味を表す。）、又は、Ａ_７’’−ＳＯ_２−Ｂ_１’−Ｒ_６−基（Ａ_７’’、Ｂ_１’及びＲ_６は、は、前記と同一の意味を表す。）、又は、Ａ_８−ＳＯ_２−Ｂ_１’−Ｒ_６−基（Ａ_８、Ｂ_１’及びＲ_６は、は、前記と同一の意味を表す。但し、Ａ_８は、水素原子となることはない。）、又は、Ａ_９’−Ｂ_２’−Ｂ_３−Ｂ_１’−Ｒ_６−基（Ａ_９’、Ｂ_２’、Ｂ_３、Ｂ_１’及びＲ_６は、は、前記と同一の意味を表す。）、又は、（ｂ）−基（（ｂ）は、前記と同一の意味を表す。）若しくは（ｃ）−基（（ｃ）は、前記と同一の意味を表す。）で置換されたC2-C10アルケニル基
である。
（１１）Ｋ群：Ａ_１０−Ｎ（（Ｏ）_ｎＲ_１）−ＣＯ−Ｒ_６−基［Ａ_１０は、水素原子（但し、ｎは０ではない。）、Ａ_７’’−ＳＯ_２−基（Ａ_７’’は、前記と同一の意味を表す。）、Ａ_８−ＳＯ_２−基（Ａ_８は、前記と同一の意味を表す。但し、Ａ_８は、水素原子とはならない。）、Ａ_９’Ｏ−基（Ａ_９’は、前記と同一の意味を表す。但し、ｎは１ではない。）、Ａ_９’−基（Ａ_９’は、前記と同一の意味を表す。但し、ｎが０のとき、Ａ_８’を除く。）、Ｒ_２ＯＣＨ_２−基（Ｒ_２は、前記と同一の意味を表す。）、Ａ_２−ＣＯ−Ｒ_４−基（Ａ_２及びＲ_４は、前記と同一の意味を表す。）又はＡ_２−ＣＯ−ＣＨ（ＣＨ_２ＣＯ−Ａ_２）−基（Ａ_２は、前記と同一の意味を表す。）を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］
である。
（１２）Ｌ群：Ａ_１０’−Ｎ（（Ｏ）_ｎＲ_１）−ＳＯ_２−Ｒ_６−基［Ａ_１０’は、水素原子（但し、ｎは０ではない。）、Ａ_９’Ｏ−基（Ａ_９’は、前記と同一の意味を表す。但し、ｎは１ではない。）、Ａ_９’−基（Ａ_９’は、前記と同一の意味を表す。但し、ｎが０のとき、Ａ_８’を除く。）、Ｒ_２−ＣＯ−基（Ｒ_２は、前記と同一の意味を表す。）、Ａ_２−ＣＯ−Ｒ_４−基（Ａ_２及びＲ_４は、前記と同一の意味を表す。）又はＡ_２−ＣＯ−ＣＨ（ＣＨ_２ＣＯ−Ａ_２）−基（Ａ_２は、前記と同一の意味を表す。）を表し、ｎ、Ｒ_１及びＲ_６は、前記と同一の意味を表す。］、Ａ_９’’Ｒ_１Ｎ−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ_１’）−Ｒ_６−基［Ａ_９’’は、水素原子又はＡ_９’−基（Ａ_９’は、前記と同一の意味を表す。）を表し、Ｒ_１、ｎ、Ｒ_１’及びＲ_６は、前記と同一の意味を表す。］又は（ｂ）−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ_１’）−Ｒ_６−基［（ｂ）、ｎ、Ｒ_１’及びＲ_６は、前記と同一の意味を表す。］
である。
（１３）Ｍ群：Ｒ_１（Ｒ_２Ｓ）Ｃ＝Ｎ−Ｒ_６−基（Ｒ_１、Ｒ_２及びＲ_６は、前記と同一の意味を表す。）、Ｒ_２Ｂ（Ｒ_２’Ｂ’）Ｃ＝Ｎ−Ｒ_６−基（Ｒ_２及びＲ_６は、前記と同一の意味を表し、Ｒ_２’は、Ｒ_２と同一又は相異なり、Ｒ_２と、同一の意味を表し、Ｂ及びＢ’は、同一又は相異なり、オキシ基又はチオ基を表す。）、Ｒ_１Ｒ_１’Ｎ−（Ｒ_２Ｓ）Ｃ＝Ｎ−Ｒ_６−基（Ｒ_１、Ｒ_１’、Ｒ_２及びＲ_６は、前記と同一の意味を表す。）、Ｒ_１Ｎ＝Ｃ（ＳＲ_２）−ＮＲ_２’−Ｒ_６−基（Ｒ_１、Ｒ_２、Ｒ_２’及びＲ_６は、前記と同一の意味を表す。）又はＲ_１（Ｒ_１’Ｏ）Ｎ−Ｒ_６−基（Ｒ_１、Ｒ_１’及びＲ_６は、前記と同一の意味を表す。）
である。
（１４）Ｎ群：Ａ_１１−Ｐ（＝Ｏ）（ＯＲ_１’）−Ｒ_４−基［Ａ_１１は、Ｒ_１−基（Ｒ_１は、前記と同一の意味を表す。）、Ｒ_１Ｏ−Ｒ_６−基（Ｒ_１及びＲ_６は、前記と同一の意味を表す。）又はＲ_１ＯＣＯ−ＣＨＲ_０−基（Ｒ_１及びＲ_０は、前記と同一の意味を表す。）を表し、Ｒ_１’及びＲ_４は、前記と同一の意味を表す。］
である。
ＩＩＩ．（Ｙ_Ａ）_ｑにおいて、Ｙ_Ａは、下記のＸ群又はＹ群の基を表し、ｑは、０、１、２又は３を表し、ｐ（ｐは、前記と同一の意味を表す。）とｑとの和は３以下であり、ｑが２以上のとき、Ｙ_Ａは、同一又は相異なり、ｑが２以上のとき、隣接している２個の同一又は相異なるＹ_Ａは、Ｚ群の基をなして、Ａ環と縮環してもよい。
(１)Ｘ群：Ｍ_ａ−基［Ｍ_ａは、Ｒ_ｂ−基（Ｒ_ｂは、ハロゲン原子で置換されてもよいC1-C10アルキル基を表す。）、ハロゲン原子、ニトロ基、シアノ基、Ｒ_ｃ−Ｂ_ａ−Ｒ_ｄ−基（Ｒ_ｃは、ハロゲン原子で置換されてもよいC1-C10アルキル基を表し、Ｂ_ａは、オキシ基、チオ基、スルフィニル基又はスルホニル基を表し、Ｒ_ｄは、単結合又はC1-C10アルキレン基を表す。）、ＨＯ−Ｒ_ｄ−基（Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅ−ＣＯ−Ｒ_ｄ−基（Ｒ_ｅは、水素原子、又は、ハロゲン原子で置換されてもよいC1-C10アルキル基を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅ−ＣＯ−Ｏ−Ｒ_ｄ−基（Ｒ_ｅ及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＯ−ＣＯ−Ｒ_ｄ−基（Ｒ_ｅ及びＲ_ｄは、前記と同一の意味を表す。）、ＨＯ−ＣＯ−ＣＨ＝ＣＨ−基、Ｒ_ｅＲ_ｅ’Ｎ−Ｒ_ｄ−基（Ｒ_ｅ及びＲ_ｅ’は、同一又は相異なり、Ｒ_ｅは、前記と同一の意味を表し、Ｒ_ｅ’は、Ｒ_ｅと同一の意味を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅ−ＣＯ−ＮＲ_ｅ’−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｂＯ−ＣＯ−Ｎ（Ｒ_ｅ）−Ｒ_ｄ−基（Ｒ_ｂ、Ｒ _ｅ及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ_ｅ’Ｎ−ＣＯ−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ_ｅ’Ｎ−ＣＯ−ＮＲ_ｅ’’−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、同一又は相異なり、Ｒ_ｅ及びＲ_ｅ’は、前記と同一の意味を表し、Ｒ_ｅ’’は、Ｒ_ｅと同一の意味を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ_ｅ’Ｎ−Ｃ（＝ＮＲ_ｅ’’）−ＮＲ_ｅ’’’−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’、Ｒ_ｅ’’及びＲ_ｅ’’’は、同一又は相異なり、Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、前記と同一の意味を表し、Ｒ_ｅ’’’は、Ｒ_ｅと同一の意味を表し、Ｒ_ｄは、前記と同一の意味を表す。）、Ｒ_ｂ−ＳＯ_２−ＮＲ_ｅ−Ｒ_ｄ−基（Ｒ_ｂ、Ｒ_ｅ及びＲ_ｄは、前記と同一の意味を表す。）、Ｒ_ｅＲ _ｅ’Ｎ−ＳＯ_２−Ｒ_ｄ−基（Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｄは、前記と同一の意味を表す。）、C2-C10アルケニル基又はC2-C10アルキニル基を表す。]である。
(２)Ｙ群：Ｍ_ｂ−Ｒ_ｄ−基［Ｍ_ｂは、Ｍ_ｃ−基｛Ｍ_ｃは、Ｍ_ｄ−Ｒ_ｄ’−基｛Ｍ_ｄは、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよいフェニル基、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよいピリジル基、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよいナフチル基、（ｂ）−基（（ｂ）は、前記と同一の意味を表す。）、（ｃ）−基（（ｃ）は、前記と同一の意味を表す。）、

（ｄ）−基（ｌは、２、３又は４であり、Ｂ_ｂは、オキシ基又はチオ基を表す。）又は

（ｅ）−基（ｌ及びＢ_ｂは、前記と同一の意味を表す。）を表し、Ｒ_ｄ’は、Ｒ_ｄと同一又は相異なり、Ｒ_ｄと同一の意味を表す。｝を表す。｝、Ｍ_ｃ−Ｂ_ａ−基（Ｍ_ｃ及びＢ_ａは、前記と同一の意味を表す。）、Ｍ_ｃ−ＣＯ−基（Ｍ_ｃは、前記と同一の意味を表す。）、Ｍ_ｃ−ＣＯ−Ｏ−基（Ｍ_ｃは、前記と同一の意味を表す。）、Ｍ_ｃＯ−ＣＯ−基（Ｍ_ｃは、前記と同一の意味を表す。）、Ｍ_ｃＲ_ｅＮ−基（Ｍ_ｃ及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃＯ−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃＲ_ｅＮ−ＣＯ−基（Ｍ_ｃ及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃＲ_ｅＮ−ＣＯ−ＮＲ_ｅ’−基（Ｍ_ｃ、Ｒ_ｅ及びＲ_ｅ’は、前記と同一の意味を表す。）、Ｍ_ｃＲ_ｅＮ−Ｃ（＝ＮＲ_ｅ’）−ＮＲ_ｅ’’−基（Ｍ_ｃ、Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、前記と同一の意味を表す。）、Ｍ_ｃ−ＳＯ_２−ＮＲ_ｅ−基（Ｍ_ｃ及びＲ_ｅは、前記と同一の意味を表す。）又はＭ_ｃＲ_ｅＮ−ＳＯ_２−基（Ｍ_ｃ及びＲ_ｅは、前記と同一の意味を表す。）を表し、Ｒ_ｄは、前記と同一の意味を表す。］である。
（３）Ｚ群：−Ｙ_ａ’’＝Ｃ（Ｙ_ａ）−Ｙ_ａ’−基（Ｙ_ａは、水素原子、又は、ハロゲン原子で置換されてもよいC1-C10アルキル基、又は、C1-C10アルコキシ基を表し、Ｙ_ａ’は、オキシ基、又は、チオ基、又は、C1-C10アルキル基で置換されてもよいイミノ基を表し、Ｙ_ａ’’は、−Ｎ＝基又はメチン基を表す。）、C3-C10アルキレン基又は−Ｙ_ｂ＝Ｙ_ｂ’−Ｙ_ｂ’’＝Ｙ_ｂ’’’−基［Ｙ_ｂ、Ｙ_ｂ’、Ｙ_ｂ’’及びＹ_ｂ’’’は、同一又は相異なり、Ｍａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよいメチン基、又は、−Ｎ＝基を表す。］である。
ＩＶ．Ｂは、
式（IV-1）

［式中、
(１)Ｑ_Ａは、水酸基、（ｂ）−基（（ｂ）は、前記と同一の意味を表す。）、Ａ_９−Ｂ_６−Ｂ_ｃ−基［Ａ_９及びＢ_６は、前記と同一の意味を表し、Ｂ_ｃは、オキシ基又は−Ｎ（（Ｏ）_ｍＲ_１）−基（ｍ及びＲ_１は、前記と同一の意味を表す。）を表す。但し、Ａ_９が水素原子のとき、Ｂ_ｃは、スルホニル基ではない。］、Ａ_７’’−ＳＯ_２−Ｂ_ｃ−基（Ａ_７’’及びＢ_ｃは、前記と同一の意味を表す。）、Ａ_８−ＳＯ_２−Ｂ_ｃ−基（Ａ_８及びＢ_ｃは、前記と同一の意味を表す。但し、Ａ_８は水素原子とはならない。）、Ｒ_１Ｒ_１’Ｎ−ＳＯ_２−Ｂ_ｃ−基（Ｒ_１、Ｒ_１’及びＢ_ｃは、前記と同一の意味を表す。）、（ｂ）−ＳＯ_２−Ｂ_ｃ−基（（ｂ）及びＢ_ｃは、前記と同一の意味を表す。）、Ａ_９’−Ｂ_ｃ−基（Ａ_９’及びＢ_ｃは、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−Ｂ_ｃ−基（Ｄ_５、Ｒ_４及びＢ_ｃは、前記と同一の意味を表す。）、Ｍ_ｃ−Ｂ_３−Ｂ_ｃ−基（Ｍ_ｃ、Ｂ_３及びＢ_ｃは、前記と同一の意味を表す。）又はＭ_ｃ−Ｂ_ｃ−基（Ｍ_ｃ及びＢ_ｃは、前記と同一の意味を表す。）を表す。
（２）Ｗ_Ａは、酸素原子又は−ＮＴ_Ａ−基［Ｔ_Ａは、水素原子、Ａ_９’−基（Ａ_９’は、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−基（Ｄ_５及びＲ_４は、前記と同一の意味を表す。）又はＭ_ｃ−基（Ｍ_ｃは、前記と同一の意味を表す。）を表す。］を表す。Ｔ_Ａは、水素原子、Ａ_９’−基（Ａ_９’は、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−基（Ｄ_５及びＲ_４は、前記と同一の意味を表す。）又はＭ_ｃ−基（Ｍ_ｃは、前記と同一の意味を表す。）を表す。
（３）Ｋ_Ａは、水素原子、ハロゲン原子又はC1-C10アルキル基を表し、Ｌ_Ａは、水素原子、C1-C10アルキル基又はＭ_ｂ−基（Ｍ_ｂは、前記と同一の意味を表す。）を表し、Ｋ_ＡとＬ_Ａとは、C3-C10アルキレン基又は−Ｃ（Ｍ_ａ’）＝Ｃ（Ｍ_ａ’’）−Ｃ（Ｍ_ａ’’’）＝Ｃ（Ｍ_ａ’’’’）−基（Ｍ_ａ’、Ｍ_ａ’’、Ｍ_ａ’’’及びＭ_ａ’’’’は、同一又は相異なり、Ｍ_ａと同一又は相異なり、水素原子又はＭ_ａを表す。）をなすことがある。］
で示される基、
式（IV-2）

[式中、Ｔ_Ａは、前記と同一の意味を表し、Ｌ_Ｂは水酸基又はメチル基を表す。]
で示される基、
式（IV-3）

[式中、Ｔ_Ａは、前記と同一の意味を表し、Ｌ_Ｃは、C1-C10アルキル基を表す。]
で示される基、
式（IV-4）

[式中、Ｔ_Ａは、前記と同一の意味を表す。]
で示される基、
式（IV-5）

[式中、Ｔ_Ａは、前記と同一の意味を表し、Ｋ_Ｂは、シアノ基又はＵＯＣＯ−基（Ｕは、水素原子又はC1-C10アルキル基を表す。）を表す。]
で示される基、
式（IV-6）

[式中、Ｗ_Ａは、前記と同一の意味を表し、Ｋ_ＣとＬ_Ｄとは、C3-C10アルキレン基又は単数又は同一又は相異なる複数のＭａ−基（Ｍａは、前記と同一の意味を表す。）で置換されてもよいC4-C10アルケニレン基をなす。]
で示される基、
式（IV-7）

[式中、Ｑ_Ａ及びＷ_Ａは、前記と同一の意味を表し、Ｋ_ＤとＬ_Ｅとは、−Ｖ_Ａ＝Ｖ_Ａ’−Ｖ_Ａ’’＝Ｖ_Ａ’’’−基｛Ｖ_Ａ、Ｖ_Ａ’、Ｖ_Ａ’’及びＶ_Ａ’’’は、同一又は相異なり、Ｍ_ａ−基（Ｍ_ａは、前記と同一の意味を表す。）で置換されてもよいメチン基、又は、−Ｎ＝基を表し、Ｖ_Ａ、Ｖ_Ａ’、Ｖ_Ａ’’及びＶ_Ａ’’’のうち少なくとも一つは−Ｎ＝基を表す。｝をなす。]
で示される基、
式（IV-8）

[式中、Ｔ_Ａは、前記と同一の意味を表し、Ｑ_Ｂは、水酸基、Ａ_９−Ｂ_６−Ｏ−基［Ａ_９及びＢ_６は、前記と同一の意味を表す。］、Ａ_７’’−ＳＯ_２−Ｏ−基（Ａ_７’’は、前記と同一の意味を表す。）、Ａ_８−ＳＯ_２−Ｏ−基（Ａ_８は、前記と同一の意味を表す。但し、Ａ_８は水素原子とはならない。）、Ｒ_１Ｒ_１’Ｎ−ＳＯ_２−Ｏ−基（Ｒ_１及びＲ_１’は、前記と同一の意味を表す。）、（ｂ）−ＳＯ_２−Ｏ−基（（ｂ）は、前記と同一の意味を表す。）、Ａ_９’−Ｏ−基（Ａ_９’は、前記と同一の意味を表す。）、Ｄ_５−Ｒ_４−Ｏ−基（Ｄ_５及びＲ_４は、前記と同一の意味を表す。）、Ｍ_ｃ−Ｂ_３−Ｏ−基（Ｍ_ｃ及びＢ_３は、前記と同一の意味を表す。）又はＭ_ｃ−Ｏ−基（Ｍ_ｃは、前記と同一の意味を表す。）を表す。]
で示される基、又は、
式（IV-9）

[式中、Ｕ及びＷ_Ａは、前記と同一の意味を表す。]
で示される基を表す。
但し、Ａがフラン環又はチオフェン環のとき、ｐ及びｑが同時に０になることはない。
尚、複数の置換基の間での同一記号における「前記と同一の意味を表す」とは、当該複数の置換基が互いに独立しながら前記と同一の意味を表すことを示し、当該複数の置換基の間では、選ばれる置換基の選択肢の範囲が同一であるが、その範囲内で選ばれる限り当該選ばれる置換基は同じであっても、異なっていてもよいことを意味するものである。］
で示されるシンナモイル化合物。
５．式（V）

［式中、
Ｉ．ａは、チオフェン環、フラン環、ピロール環、ピラゾール環、１，２，３−トリアゾール環、テトラゾール環、イソオキサゾール環、チアゾール環、ピリダジン環又はピリミジン環を表し、Ｘ_ａは、シアノ基で置換されたC1-C10アルキル基、又は、テトラヒドロピラン−４−イリデン基で置換されたC1-C10アルキル基、又は、ハロゲン原子若しくはシアノ基で置換されたC2-C10アルケニル基、又は、C1-C10アルコキシカルボニル基で置換されたC2-C10アルケニル基、又は、ヒドロキシ基で置換されたC3-C10アルキニル基、又は、ａ_０−ｒ_１−ｂ−ｒ_１’−基｛ａ_０は、C1-C10アルキルチオ基で置換されたメチル基、C1-C10アルキルスルフィニル基で置換されたメチル基、C1-C10アルキルスルホニル基で置換されたメチル基、C2-C10アルケニル基、C2-C10アルキニル基、ｒ_２Ｏ−ＣＯ−基（ｒ_２は、C1-C10アルキル基又は水酸基で置換されたC2-C10アルキル基を表す。）、カルボキシ基、ｒｒ’Ｎ−ＣＯ−基（ｒ及びｒ’は、同一又は相異なり、水素原子又はC1-C10アルキル基を表す。）、ａ_１−ＮＨ−ＣＯ−基（ａ_１は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表す。）、ａ_１’−ＣＯ−基（ａ_１’は、モルホリノ基を表す。）、ｒｒ’Ｎ−ＣＨ_２−基（ｒ及びｒ’は、前記と同一の意味を表す。）、ｒ_０−（Ｏ）_ｌ−ＣＯＮＨ−ＣＨ_２−基（ｒ_０は、C1-C10アルキル基を表し、ｌは０又は１を表す。）、ｒ−ＯＣＨ_２−基（ｒは、前記と同一の意味を表す。）、ｒ_０−ＣＯ−基（ｒ_０は、前記と同一の意味を表す。）、シアノ基又はスルホメチル基を表し、ｒ_１は、C1-C10アルキレン基を表し、ｒ_１’は、単結合又はC1-C10アルキレン基を表し、ｂは、オキシ基、チオ基、スルフィニル基、スルホニル基又はメチル基で置換されてもよいイミノ基を表す。｝、又は、ａ_２−ｙ−ＣＯ−ＮＨ−基（ａ_２は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表し、ｙは、オキシ基又はイミノ基を表す。）、又は、ｒＯ−ＣＯＣＯ−ＮＨ−基（ｒは、前記と同一の意味を表す。）、又は、ａ_３−z−ＮＨ−基（ａ_３は、C2-C10アルケニル基、又は、C1-C10アルコキシ基、C1-C10アルコキシカルボニル基、カルボキシ基若しくはシアノ基で置換されたC1-C10アルキル基を表し、ｚは、カルボニル基又はスルホニル基を表す。）、又は、ａ_４−Ｎｒ’ＣＯ−基｛ａ_４は、C1-C10アルコキシ基、又は、C3-C10アルケニルオキシ基、又は、ｒ_０−ＳＯ_２−基（ｒ_０は、前記と同一の意味を表す。）、又は、水酸基若しくはC1-C10アルコキシ基で置換されたC2-C10アルキル基、又は、ｒ_０ｒ_０’Ｎ−基（ｒ_０は、前記と同一の意味を表し、ｒ_０’は、ｒ_０と同一又は相異なり、ｒ_０と同一の意味を表す。）で置換されたC2-C10アルキル基、又は、ｒＯ−ＣＯ−基（ｒは、前記と同一の意味を表す。）、シアノ基若しくはアミノカルボニル基で置換されたC1-C10アルキル基、又は、ｒＯ−ＣＯ−（ｒＯ−ＣＯＣＨ_２）ＣＨ−基（ｒは、前記と同一の意味を表す。）を表し、ｒ’は、前記と同一の意味を表す。｝、又は、ａ_５−ＮＨＳＯ_２−基（ａ_５は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表す。）、又は、ｒ_０ＯＮ＝ＣＨ−基（ｒ_０は、前記と同一の意味を表す。）、又は、ｒ_０ＮＨＣＳＮＨ−基（ｒ_０は、前記と同一の意味を表す。）、又は、ｒ_０ＮＨＣ（−Ｓｒ_０’）＝Ｎ−基（ｒ_０及びｒ_０’は、前記と同一の意味を表す。）、又は、（ｒＯ）_２Ｐ（＝Ｏ）ＣＨ_２−基（ｒは、前記と同一の意味を表す。）を表し、ｐは、０、１、２又は３を表し、ｐが２以上のとき、Ｘ_ａは、同一又は相異なり、
Ｙ_ａは、ハロゲン原子、又は、ハロゲン原子で置換されてもよいC1-C10アルキル基、又は、C1-C10アルコキシ基で置換されてもよいC1-C10アルキル基、又は、C2-C10アルケニル基、又は、C2-C10アルキニル基、又は、２−オキソ−オキサゾリジン−３−イル基、又は、[１,３]ジオキソラン−２−イル基、又は、モルホリノ基で置換されたC1-C10アルコキシ基、又は、ａ_０’−ｂ’−基（ａ_０’は、ハロゲン原子で置換されてもよいC1-C10アルキル基を表し、ｂ’は、オキシ基、チオ基、スルフィニル基又はスルホニル基を表す。）、又は、ニトロ基、又は、シアノ基、又は、ｒＯ−ＣＯ−基（ｒは、前記と同一の意味を表す。）、又は、ｒ_０ｒ_０’Ｎ−基（ｒ_０及びｒ_０’は、前記と同一の意味を表す。）、又は、ｒ_０ＣＯ−ＮＨ−基（ｒ_０は、前記と同一の意味を表す。）、又は、ｒ_０ｒ_０’ＮＣＯＮＨ−基（ｒ_０及びｒ_０’は、前記と同一の意味を表す。）、又は、ｒｒ’ＮＣＯ−基（ｒ及びｒ’は、前記と同一の意味を表す。）、又は、水酸基を表し、ｑは、０、１、２又は３を表し、ｑが２以上のとき、Ｙ_ａは、同一又は相異なり、ｑが２以上のとき、隣接しているＹ_ａは、ａ環と縮環して４,５,６,７−テトラヒドロベンゾ[ｂ]チオフェン環をなしてもよい。
ＩＩ．ｂは、
式（V-1）

［式中、Ｑ_ａは、ｒ_ａ−Ｏ−基｛ｒ_ａは、水素原子、又は、C1-C10アルキル基、又は、C3-C10アルケニル基、又は、C3-C10アルキニル基、又は、ｒ_０ｒ_０’Ｎ−ＣＨ_２−基（ｒ_０及びｒ_０’は、前記と同一の意味を表す。）、ｒＯＣＨ_２−基（ｒは、前記と同一の意味を表す。）、ｒ_０−ＣＯ−基（ｒ_０は、前記と同一の意味を表す。）、C1-C10アルコキシカルボニル基、カルボキシ基、アミノカルボニル基若しくはシアノ基で置換されたC1-C10アルキル基、又は、ｒ_３−ｒ_１−基（ｒ_３は、フェニル基又はピリジル基を表し、ｒ_１は、前記と同一の意味を表す。）を表す。｝、又は、ピペリジノ基、又は、モルホリノ基、又は、ｒ_４ｒ_４’Ｎ−基（ｒ_４及びｒ_４’は、同一又は相異なり、水素原子、又は、C1-C10アルキル基、又は、C3-C10アルケニル基、又は、C3-C10アルキニル基、又は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表す。但し、同時に水素原子となることはない。）を表し、Ｗ_ａは、酸素原子又は−ＮＴ_ａ−基［Ｔ_ａは、ｒ_ｂ−基（ｒ_ｂは、ｒ_ａと同一又は相異なり、ｒ_ａと同一の意味を表す。）又はｒ_３’−基（ｒ_３’は、ｒ_３と同一又は相異なり、ｒ_３と同一の意味を表す。）を表す。］を表し、Ｋ_ａは、水素原子、ハロゲン原子又はC1-C10アルキル基を表し、Ｌ_ａは、水素原子又はC1-C10アルキル基を表し、Ｋ_ａとＬ_ａとは、C3-C10アルキレン基又は１，３−ブタジエニレン基をなすことがある。］
で示される基、
式（V-2）

[式中、Ｔ_ａは、前記と同一の意味を表し、Ｌ_ｂは水酸基又はメチル基を表す。]
で示される基、
式（V-3）

[式中、Ｔ_ａは、前記と同一の意味を表し、Ｌ_ｃは、C1-C10アルキル基を表す。]
で示される基、
式（V-4）

[式中、Ｔ_ａは、前記と同一の意味を表す。]
で示される基、
式（V-5）

[式中、Ｔ_ａは、前記と同一の意味を表し、Ｋ_ｂは、シアノ基又はＵＯＣＯ−基（Ｕは、水素原子又はC1-C10アルキル基を表す。）を表す。]
で示される基、
式（V-6）

[式中、Ｗ_ａは、前記と同一の意味を表し、Ｋ_ｃとＬ_ｄとは、C3-C10アルキレン基又はC4-C10アルケニレン基をなす。]
で示される基、
式（V-7）

[式中、Ｑ_ａ及びＷ_ａは、前記と同一の意味を表し、Ｋ_ｄとＬ_ｅとは、−Ｖ_ａ＝Ｖ_ａ’−Ｖ_ａ’’＝Ｖ_ａ’’’−基（Ｖ_ａ、Ｖ_ａ’、Ｖ_ａ’’及びＶ_ａ’’’は、同一又は相異なり、メチン基、又は、−Ｎ＝基を表し、Ｖ_ａ、Ｖ_ａ’、Ｖ_ａ’’及びＶ_ａ’’’のうち少なくとも一つは−Ｎ＝基を表す。）をなす。]
で示される基、
式（V-8）

[式中、Ｔ_ａは、前記と同一の意味を表し、Ｑ_ｂは、ｒ_ａ−Ｏ−基（ｒ_ａは、前記と同一の意味を表す。）を表す。]
で示される基、又は、
式（V-9）

[式中、Ｕ及びＷ_ａは、前記と同一の意味を表す。]
で示される基を表す。
但し、ａがフラン環又はチオフェン環のとき、ｐ及びｑが同時に０になることはない。
尚、複数の置換基の間での同一記号における「前記と同一の意味を表す」とは、当該複数の置換基が互いに独立しながら前記と同一の意味を表すことを示し、当該複数の置換基の間では、選ばれる置換基の選択肢の範囲が同一であるが、その範囲内で選ばれる限り当該選ばれる置換基は同じであっても、異なっていてもよいことを意味するものである。］
で示されるシンナモイル化合物。
６．式（VI）

［式中、ａ１は、チオフェン環、フラン環、ピロール環又はチアゾール環を表し、Ｘ_ａ1は、ａ_０’−ｒ_１−ｂ_０−ｒ_１’−基｛ａ_０’は、ｒＯ−ＣＯ−基（ｒは、水素原子又はC1-C10アルキル基を表す。）、ｒ_０ｒ_０’Ｎ−ＣＨ_２−基（ｒ_０及びｒ_０’は、同一又は相異なり、C1-C10アルキル基を表す。）、又は、ヒドロキシメチル基を表し、ｒ_１は、C1-C10アルキレン基を表し、ｒ_１’は、単結合又はC1-C10アルキレン基を表し、ｂ_０は、オキシ基、チオ基、スルフィニル基、スルホニル基又は１個のメチル基で置換されたイミノ基を表す。｝、又は、ａ_２−Ｏ−ＣＯ−ＮＨ−基（ａ_２は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表す。）、又は、ａ_３’−ＣＯ−ＮＨ−基（ａ_３’は、C1-C10アルコキシ基で置換されたC1-C10アルキル基を表す。）、又は、ａ_４’−ＮｒＣＯ−基
（ａ_４’は、水酸基若しくはC1-C10アルコキシ基で置換されたC2-C10アルキル基、又は、
アミノカルボニル基で置換されたC1-C10アルキル基を表し、ｒは、前記と同一の意味を表す。）を表し、ｂ１は、
式（VI-1）

（式中、ｒ_ｂ１は、水素原子又はC1-C10アルキル基を表し、Ｋ_ａ１は、水素原子を表し、Ｌ_ａ１は、C1-C10アルキル基を表し、Ｋ_ａ１とＬ_ａ１とは、１，３−ブタジエニレン基をなすことがある。）
で示される基、
式（VI-7）

（式中、ｒ_ｂ１は、前記と同一の意味を表す。）
で示される基、又は、
式（VI-8）

（式中、ｒ_ｂ１は、前記と同一の意味を表す。）
で示される基を表す。
尚、複数の置換基の間での同一記号における「前記と同一の意味を表す」とは、当該複数の置換基が互いに独立しながら前記と同一の意味を表すことを示し、当該複数の置換基の間では、選ばれる置換基の選択肢の範囲が同一であるが、その範囲内で選ばれる限り当該選ばれる置換基は同じであっても、異なっていてもよいことを意味するものである。］
で示されるシンナモイル化合物。
７．式（VII）

［式中、ａ１は、チオフェン環、フラン環、ピロール環又はチアゾール環を表し、Ｘ_ａ１は、ａ_０’−ｒ_１−ｂ_０−ｒ_１’−基｛ａ_０’は、ｒ_０Ｏ−ＣＯ−基（ｒ_０は、C1-C10アルキル基を表す。）、ｒ_０ｒ_０’Ｎ−ＣＨ_２−基（ｒ_０及びｒ_０’は、同一又は相異なり、ｒ_０’は、ｒ_０と同一の意味を表す。）、又は、ヒドロキシメチル基を表し、ｒ_１は、C1-C10アルキレン基を表し、ｒ_１’は、単結合又はC1-C10アルキレン基を表し、ｂ_０は、オキシ基、チオ基、スルフィニル基、スルホニル基又は１個のメチル基で置換されたイミノ基を表す。｝、又は、ａ_２−Ｏ−ＣＯ−ＮＨ−基（ａ_２は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表す。）、又は、ａ_３’−ＣＯ−ＮＨ−基（ａ_３’は、C1-C10アルコキシ基で置換されたC1-C10アルキル基を表す。）、又は、ａ_４’−ＮｒＣＯ−基
（ａ_４’は、水酸基若しくはC1-C10アルコキシ基で置換されたC2-C10アルキル基、又は、
アミノカルボニル基で置換されたC1-C10アルキル基を表し、ｒは、水素原子又はC1-C10アルキル基を表す。）を表す。但し、ａ１がチオフェン環のとき、同時に、ａ_０’がジメチルアミノメチル基又はヒドロキシメチル基であって、同時に、ｒ_１がメチレン基であって、同時に、ｒ_１’が単結合であって、同時に、ｂ_０は、オキシ基、チオ基又は１個のメチル基で置換されたイミノ基であることはなく、また、ａ１がチオフェン環のとき、ａ_０’がメトキシカルボニル基であって、同時に、ｒ_１がメチレン基であって、同時に、ｒ_１’が単結合であって、同時に、ｂ_０は、チオ基であることはない。］
で示されるアルデヒド誘導体。
８．式（VIII）

［式中、ａ１は、チオフェン環、フラン環、ピロール環又はチアゾール環を表し、Ｘ_ａ１は、ａ_０’−ｒ_１−ｂ_０−ｒ_１’−基｛ａ_０’は、ｒ_０Ｏ−ＣＯ−基（ｒ_０は、C1-C10アルキル基を表す。）、ｒ_０ｒ_０’Ｎ−ＣＨ_２−基（ｒ_０及びｒ_０’は、同一又は相異なり、ｒ_０’は、ｒ_０と同一の意味を表す。）、又は、ヒドロキシメチル基を表し、ｒ_１は、C1-C10アルキレン基を表し、ｒ_１’は、単結合又はC1-C10アルキレン基を表し、ｂ_０は、オキシ基、チオ基、スルフィニル基、スルホニル基又は１個のメチル基で置換されたイミノ基を表す。｝、又は、ａ_２−Ｏ−ＣＯ−ＮＨ−基（ａ_２は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表す。）、又は、ａ_３’−ＣＯ−ＮＨ−基（ａ_３’は、C1-C10アルコキシ基で置換されたC1-C10アルキル基を表す。）、又は、ａ_４’−ＮｒＣＯ−基
（ａ_４’は、水酸基若しくはC1-C10アルコキシ基で置換されたC2-C10アルキル基、又は、
アミノカルボニル基で置換されたC1-C10アルキル基を表し、ｒは、水素原子又はC1-C10アルキル基を表す。）を表す。但し、ａ１がチオフェン環のとき、同時に、ａ_０’がジメチルアミノメチル基又はヒドロキシメチル基であって、同時に、ｒ_１がメチレン基であって、同時に、ｒ_１’が単結合であって、同時に、ｂ_０は、オキシ基、チオ基又は１個のメチル基で置換されたイミノ基であることはなく、また、ａ１がチオフェン環のとき、ａ_０’がメトキシカルボニル基であって、同時に、ｒ_１がメチレン基であって、同時に、ｒ_１’が単結合であって、同時に、ｂ_０は、チオ基であることはない。］
で示されるアルデヒド誘導体と、式（VIII’）

［式中、ｂ１は、
式（VIII-1）

（式中、ｒ_ｂ１は、水素原子又はC1-C10アルキル基を表し、Ｋ_ａ１は、水素原子を表し、Ｌ_ａ１は、C1-C10アルキル基を表し、Ｋ_ａ１とＬ_ａ１とは、１，３−ブタジエニレン基をなすことがある。）
で示される基、
式（VIII-7）

（式中、ｒ_ｂ１は、前記と同一の意味を表す。）
で示される基、又は、
式（VIII-8）

（式中、ｒ_ｂ１は、前記と同一の意味を表す。）
で示される基を表す。]
で示される化合物とを反応させることを特徴とする、式（VIII’’）

［式中、ａ１、Ｘ_ａ１及びｂ１は、前記と同一の意味を表す。］
で示されるシンナモイル化合物の製造法。
９．式（I'）

（ｅ_０）−基｛ｅ_０は、カルボニル基、チオカルボニル基、オキシ基、チオ基、−ＮＲ_１-基（Ｒ_１は、前記と同一の意味を表す。）、スルフィニル基若しくはスルホニル基で置換されてもよい５−１２員の炭化水素環をなす。｝を表し、Ｒ_ｄ’は、Ｒ_ｄと同一又は相異なり、Ｒ_ｄと同一の意味を表す。｝を表す。｝、Ｍ_ｃ０−Ｂ_ａ−基（Ｍ_ｃ０及びＢ_ａは、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−Ｏ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｏ−ＣＯ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｏ−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−ＣＯ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−ＣＯ−ＮＲ_ｅ’−基（Ｍ_ｃ０、Ｒ_ｅ及びＲ_ｅ’は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−Ｃ（＝ＮＲ_ｅ’）−ＮＲ_ｅ’’−基（Ｍ_ｃ０、Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、前記と同一の意味を表す。）、Ｍ_ｃ０−ＳＯ_２−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）又はＭ_ｃ０Ｒ_ｅＮ−ＳＯ_２−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）を表し、Ｒ_ｄは、前記と同一の意味を表す。］である。
(３)Ｚ_０群：ハロゲン原子、C1-C10アルコキシ基、C3-C10アルケニルオキシ基、C3-C10アルキニルオキシ基、カルボニル基、チオカルボニル基、オキシ基、チオ基、スルフィニル基若しくはスルホニル基を有してもよい、５−１２員環の炭化水素環又は複素環であって、芳香族又は非芳香族の、単環又は縮環であって、α環と縮環する基である。
ＩＩ．β'は、
式（I'-1）

［式中、
(１)Ｑ_αは、置換されてもよい水酸基、又は、置換されてもよいアミノ基を表す。
(２)Ｗ_αは、酸素原子又は−ＮＴ_α−基（Ｔ_αは、水素原子、又は、窒素原子上の置換基を表す。）を表す。
(３)Ｋ_α及びＬ_αは、同一又は相異なり、水素原子、又は、炭素原子上の置換基を表し、Ｋ_αとＬ_αとは、置換基を有してもよいC3-C10アルキレン基又は置換基を有してもよいC4-C10アルケニレン基をなすことがある。］
で示される基、
式（I'-2）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｌ_βは水酸基又はメチル基を表す。]
で示される基、
式（I'-3）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｌ_γは、C1-C10アルキル基を表す。]
で示される基、
式（I'-4）

[式中、Ｔ_αは、前記と同一の意味を表す。]
で示される基、
式（I'-5）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｋ_βは、シアノ基又はＵＯＣＯ−基（Ｕは、水素原子又はC1-C10アルキル基を表す。）を表す。]
で示される基、
式（I'-6）

[式中、Ｗ_αは、前記と同一の意味を表し、Ｋ_γとＬ_δとは、置換基を有してもよいC3-C10アルキレン基又は置換基を有してもよいC4-C10アルケニレン基をなす。]
で示される基、
式（I'-7）

[式中、Ｑ_α及びＷ_αは、前記と同一の意味を表し、Ｋ_δとＬ_εとは、−Ｖ_α＝Ｖ_α’−Ｖ_α’’＝Ｖ_α’’’−基（Ｖ_α、Ｖ_α’、Ｖ_α’’及びＶ_α’’’は、同一又は相異なり、置換されてもよいメチン基、又は、−Ｎ＝基を表し、Ｖ_α、Ｖ_α’、Ｖ_α’’及びＶ_α’’’のうち少なくとも一つは−Ｎ＝基を表す。）をなす。]
で示される基、
式（I'-8）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｑ_βは、置換されてもよい水酸基を表す。]
で示される基、又は、
式（I'-9）

[式中、Ｗ_αは、前記と同一の意味を表す。]
で示される基を表す。
尚、複数の置換基の間での同一記号における「前記と同一の意味を表す」とは、当該複数の置換基が互いに独立しながら前記と同一の意味を表すことを示し、当該複数の置換基の間では、選ばれる置換基の選択肢の範囲が同一であるが、その範囲内で選ばれる限り当該選ばれる置換基は同じであっても、異なっていてもよいことを意味するものである。］
で示されるシンナモイル化合物と不活性担体とを含有することを特徴とする細胞外マトリックス遺伝子転写抑制組成物。
１０．式（II'）

（ｅ_０）−基｛ｅ_０は、カルボニル基、チオカルボニル基、オキシ基、チオ基、−ＮＲ_１-基（Ｒ_１は、前記と同一の意味を表す。）、スルフィニル基若しくはスルホニル基で置換されてもよい５−１２員の炭化水素環をなす。｝を表し、Ｒ_ｄ’は、Ｒ_ｄと同一又は相異なり、Ｒ_ｄと同一の意味を表す。｝を表す。｝、Ｍ_ｃ０−Ｂ_ａ−基（Ｍ_ｃ０及びＢ_ａは、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−Ｏ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｏ−ＣＯ−基（Ｍ_ｃ０は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｏ−ＣＯ−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−ＣＯ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−ＣＯ−ＮＲ_ｅ’−基（Ｍ_ｃ０、Ｒ_ｅ及びＲ_ｅ’は、前記と同一の意味を表す。）、Ｍ_ｃ０Ｒ_ｅＮ−Ｃ（＝ＮＲ_ｅ’）−ＮＲ_ｅ’’−基（Ｍ_ｃ０、Ｒ_ｅ、Ｒ_ｅ’及びＲ_ｅ’’は、前記と同一の意味を表す。）、Ｍ_ｃ０−ＳＯ_２−ＮＲ_ｅ−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）又はＭ_ｃ０Ｒ_ｅＮ−ＳＯ_２−基（Ｍ_ｃ０及びＲ_ｅは、前記と同一の意味を表す。）を表し、Ｒ_ｄは、前記と同一の意味を表す。］である。
(３)Ｚ_０群：ハロゲン原子、C1-C10アルコキシ基、C3-C10アルケニルオキシ基、C3-C10アルキニルオキシ基、カルボニル基、チオカルボニル基、オキシ基、チオ基、スルフィニル基若しくはスルホニル基を有してもよい、５−１２員環の炭化水素環又は複素環であって、芳香族又は非芳香族の、単環又は縮環であって、α環と縮環する基である。
ＩＩ．β'は、
式（II'-1）

［式中、
(１)Ｑ_αは、置換されてもよい水酸基、又は、置換されてもよいアミノ基を表す。
(２)Ｗ_αは、酸素原子又は−ＮＴ_α−基（Ｔ_αは、水素原子、又は、窒素原子上の置換基を表す。）を表す。
(３)Ｋ_α及びＬ_αは、同一又は相異なり、水素原子、又は、炭素原子上の置換基を表し、Ｋ_αとＬ_αとは、置換基を有してもよいC3-C10アルキレン基又は置換基を有してもよいC4-C10アルケニレン基をなすことがある。］
で示される基、
式（II'-2）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｌ_βは水酸基又はメチル基を表す。]
で示される基、
式（II'-3）

[式中、Ｔ_αは、前記と同一の意味を表す。]
で示される基、
式（II'-5）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｋ_βは、シアノ基又はＵＯＣＯ−基（Ｕは、水素原子又はC1-C10アルキル基を表す。）を表す。]
で示される基、
式（II'-6）

[式中、Ｗ_αは、前記と同一の意味を表し、Ｋ_γとＬ_δとは、置換基を有してもよいC3-C10アルキレン基又は置換基を有してもよいC4-C10アルケニレン基をなす。]
で示される基、
式（II'-7）

[式中、Ｑ_α及びＷ_αは、前記と同一の意味を表し、Ｋ_δとＬ_εとは、−Ｖ_α＝Ｖ_α’−Ｖ_α’’＝Ｖ_α’’’−基（Ｖ_α、Ｖ_α’、Ｖ_α’’及びＶ_α’’’は、同一又は相異なり、置換されてもよいメチン基、又は、−Ｎ＝基を表し、Ｖ_α、Ｖ_α’、Ｖ_α’’及びＶ_α’’’のうち少なくとも一つは−Ｎ＝基を表す。）をなす。]
で示される基、
式（II'-8）

[式中、Ｔ_αは、前記と同一の意味を表し、Ｑ_βは、置換されてもよい水酸基を表す。]
で示される基、又は、
式（II'-9）

[式中、Ｗ_αは、前記と同一の意味を表す。]
で示される基を表す。
但し、αがフラン環又はチオフェン環のとき、ｐ及びｑが同時に０になることはない。
尚、複数の置換基の間での同一記号における「前記と同一の意味を表す」とは、当該複数の置換基が互いに独立しながら前記と同一の意味を表すことを示し、当該複数の置換基の間では、選ばれる置換基の選択肢の範囲が同一であるが、その範囲内で選ばれる限り当該選ばれる置換基は同じであっても、異なっていてもよいことを意味するものである。］
で示されるシンナモイル化合物。
１１．式（V'）

［式中、
Ｉ．ａは、チオフェン環、フラン環、ピロール環又はテトラゾール環を表し、Ｘ_ａは、シアノ基で置換されたC1-C10アルキル基、又は、テトラヒドロピラン−４−イリデン基で置換されたC1-C10アルキル基、又は、ハロゲン原子若しくはシアノ基で置換されたC2-C10アルケニル基、又は、C1-C10アルコキシカルボニル基で置換されたC2-C10アルケニル基、又は、ヒドロキシ基で置換されたC3-C10アルキニル基、又は、ａ_０−ｒ_１−ｂ−ｒ_１’−基｛ａ_０は、C1-C10アルキルチオ基で置換されたメチル基、C1-C10アルキルスルフィニル基で置換されたメチル基、C1-C10アルキルスルホニル基で置換されたメチル基、C2-C10アルケニル基、C2-C10アルキニル基、ｒ_２Ｏ−ＣＯ−基（ｒ_２は、C1-C10アルキル基又は水酸基で置換されたC2-C10アルキル基を表す。）、カルボキシ基、ｒｒ’Ｎ−ＣＯ−基（ｒ及びｒ’は、同一又は相異なり、水素原子又はC1-C10アルキル基を表す。）、ａ_１−ＮＨ−ＣＯ−基（ａ_１は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表す。）、ａ_１’−ＣＯ−基（ａ_１’は、モルホリノ基を表す。）、ｒｒ’Ｎ−ＣＨ_２−基（ｒ及びｒ’は、前記と同一の意味を表す。）、ｒ_０−（Ｏ）_ｌ−ＣＯＮＨ−ＣＨ_２−基（ｒ_０は、C1-C10アルキル基を表し、ｌは０又は１を表す。）、ｒ−ＯＣＨ_２−基（ｒは、前記と同一の意味を表す。）、ｒ_０−ＣＯ−基（ｒ_０は、前記と同一の意味を表す。）、シアノ基又はスルホメチル基を表し、ｒ_１は、C1-C10アルキレン基を表し、ｒ_１’は、単結合又はC1-C10アルキレン基を表し、ｂは、オキシ基、チオ基、スルフィニル基、スルホニル基又はイミノ基を表す。｝、又は、ａ_２−ｙ−ＣＯ−ＮＨ−基（ａ_２は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表し、ｙは、オキシ基又はイミノ基を表す。）、又は、ｒＯ−ＣＯＣＯ−ＮＨ−基（ｒは、前記と同一の意味を表す。）、又は、ａ_３−z−ＮＨ−基（ａ_３は、C2-C10アルケニル基、又は、C1-C10アルコキシ基、C1-C10アルコキシカルボニル基、カルボキシ基若しくはシアノ基で置換されたC1-C10アルキル基を表し、ｚは、カルボニル基又はスルホニル基を表す。）、又は、ａ_４−Ｎｒ’ＣＯ−基｛ａ_４は、C1-C10アルコキシ基、又は、C3-C10アルケニルオキシ基、又は、ｒ_０−ＳＯ_２−基（ｒ_０は、前記と同一の意味を表す。）、又は、水酸基若しくはC1-C10アルコキシ基で置換されたC2-C10アルキル基、又は、ｒ_０ｒ_０’Ｎ−基（ｒ_０は、前記と同一の意味を表し、ｒ_０’は、ｒ_０と同一又は相異なり、ｒ_０と同一の意味を表す。）で置換されたC2-C10アルキル基、又は、ｒＯ−ＣＯ−基（ｒは、前記と同一の意味を表す。）、シアノ基若しくはアミノカルボニル基で置換されたC1-C10アルキル基、又は、ｒＯ−ＣＯ−（ｒＯ−ＣＯＣＨ_２）ＣＨ−基（ｒは、前記と同一の意味を表す。）を表し、ｒ’は、前記と同一の意味を表す。｝、又は、ａ_５−ＮＨＳＯ_２−基（ａ_５は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表す。）、又は、ｒ_０ＯＮ＝ＣＨ−基（ｒ_０は、前記と同一の意味を表す。）、又は、ｒ_０ＮＨＣＳＮＨ−基（ｒ_０は、前記と同一の意味を表す。）、又は、ｒ_０ＮＨＣ（−Ｓｒ_０’）＝Ｎ−基（ｒ_０及びｒ_０’は、前記と同一の意味を表す。）、又は、（ｒＯ）_２Ｐ（＝Ｏ）ＣＨ_２−基（ｒは、前記と同一の意味を表す。）を表し、ｐは、０、１、２又は３を表し、ｐが２以上のとき、Ｘ_ａは、同一又は相異なり、
Ｙ_ａは、ハロゲン原子、又は、ハロゲン原子で置換されてもよいC1-C10アルキル基、又は、C1-C10アルコキシ基で置換されてもよいC1-C10アルキル基、又は、C2-C10アルケニル基、又は、C2-C10アルキニル基、又は、２−オキソ−オキサゾリジン−３−イル基、又は、[１,３]ジオキソラン−２−イル基、又は、モルホリノ基で置換されたC1-C10アルコキシ基、又は、ａ_０’−ｂ’−基（ａ_０’は、ハロゲン原子で置換されてもよいC1-C10アルキル基を表し、ｂ’は、オキシ基、チオ基、スルフィニル基又はスルホニル基を表す。）、又は、ニトロ基、又は、シアノ基、又は、ｒＯ−ＣＯ−基（ｒは、前記と同一の意味を表す。）、又は、ｒ_０ｒ_０’Ｎ−基（ｒ_０及びｒ_０’は、前記と同一の意味を表す。）、又は、ｒ_０ＣＯ−ＮＨ−基（ｒ_０は、前記と同一の意味を表す。）、又は、ｒ_０ｒ_０’ＮＣＯＮＨ−基（ｒ_０及びｒ_０’は、前記と同一の意味を表す。）、又は、ｒｒ’ＮＣＯ−基（ｒ及びｒ’は、前記と同一の意味を表す。）、又は、水酸基を表し、ｑは、０、１、２又は３を表し、ｑが２以上のとき、Ｙ_ａは、同一又は相異なり、ｑが２以上のとき、隣接しているＹ_ａは、ａ環と縮環して２,３−ジヒドロ−ベンゾ[１,４]ジオキシン環をなしてもよい。
ＩＩ．ｂ'は、
式（V'-1）

［式中、Ｑ_ａは、ｒ_ａ−Ｏ−基｛ｒ_ａは、水素原子、又は、C1-C10アルキル基、又は、C3-C10アルケニル基、又は、C3-C10アルキニル基、又は、ｒ_０ｒ_０’Ｎ−ＣＨ_２−基（ｒ_０及びｒ_０’は、前記と同一の意味を表す。）、ｒＯＣＨ_２−基（ｒは、前記と同一の意味を表す。）、ｒ_０−ＣＯ−基（ｒ_０は、前記と同一の意味を表す。）、C1-C10アルコキシカルボニル基、カルボキシ基、アミノカルボニル基若しくはシアノ基で置換されたC1-C10アルキル基、又は、ｒ_３−ｒ_１−基（ｒ_３は、フェニル基又はピリジル基を表し、ｒ_１は、前記と同一の意味を表す。）を表す。｝、又は、ピペリジノ基、又は、モルホリノ基、又は、ｒ_４ｒ_４’Ｎ−基（ｒ_４及びｒ_４’は、同一又は相異なり、水素原子、又は、C1-C10アルキル基、又は、C3-C10アルケニル基、又は、C3-C10アルキニル基、又は、C1-C10アルコキシ基で置換されたC2-C10アルキル基を表す。但し、同時に水素原子となることはない。）を表し、Ｗ_ａは、酸素原子又は−ＮＴ_ａ−基［Ｔ_ａは、ｒ_ｂ−基（ｒ_ｂは、ｒ_ａと同一又は相異なり、ｒ_ａと同一の意味を表す。）又はｒ_３’−基（ｒ_３’は、ｒ_３と同一又は相異なり、ｒ_３と同一の意味を表す。）を表す。］を表し、Ｋ_ａは、水素原子、ハロゲン原子又はC1-C10アルキル基を表し、Ｌ_ａは、水素原子又はC1-C10アルキル基を表し、Ｋ_ａとＬ_ａとは、C3-C10アルキレン基又は１，３−ブタジエニレン基をなすことがある。］
で示される基、
式（V'-2）

[式中、Ｔ_ａは、前記と同一の意味を表し、Ｌ_ｂは水酸基又はメチル基を表す。]
で示される基、
式（V'-3）

[式中、Ｔ_ａは、前記と同一の意味を表し、Ｌ_ｃは、C1-C10アルキル基を表す。]
で示される基、
式（V'-4）

[式中、Ｔ_ａは、前記と同一の意味を表す。]
で示される基、
式（V'-5）

[式中、Ｔ_ａは、前記と同一の意味を表し、Ｋ_ｂは、シアノ基又はＵＯＣＯ−基（Ｕは、水素原子又はC1-C10アルキル基を表す。）を表す。]
で示される基、
式（V'-6）

[式中、Ｗ_ａは、前記と同一の意味を表し、Ｋ_ｃとＬ_ｄとは、C3-C10アルキレン基又はC4-C10アルケニレン基をなす。]
で示される基、
式（V'-7）

[式中、Ｑ_ａ及びＷ_ａは、前記と同一の意味を表し、Ｋ_ｄとＬ_ｅとは、−Ｖ_ａ＝Ｖ_ａ’−Ｖ_ａ’’＝Ｖ_ａ’’’−基（Ｖ_ａ、Ｖ_ａ’、Ｖ_ａ’’及びＶ_ａ’’’は、同一又は相異なり、メチン基、又は、−Ｎ＝基を表し、Ｖ_ａ、Ｖ_ａ’、Ｖ_ａ’’及びＶ_ａ’’’のうち少なくとも一つは−Ｎ＝基を表す。）をなす。]
で示される基、
式（V'-8）

[式中、Ｔ_ａは、前記と同一の意味を表し、Ｑ_ｂは、ｒ_ａ−Ｏ−基（ｒ_ａは、前記と同一の意味を表す。）を表す。]
で示される基、又は、
式（V-9'）

[式中、Ｗ_ａは、前記と同一の意味を表す。]
で示される基を表す。
但し、ａがフラン環又はチオフェン環のとき、ｐ及びｑが同時に０になることはない。
尚、複数の置換基の間での同一記号における「前記と同一の意味を表す」とは、当該複数の置換基が互いに独立しながら前記と同一の意味を表すことを示し、当該複数の置換基の間では、選ばれる置換基の選択肢の範囲が同一であるが、その範囲内で選ばれる限り当該選ばれる置換基は同じであっても、異なっていてもよいことを意味するものである。］
で示されるシンナモイル化合物。
１２．前項２〜６、１０及び１１記載の化合物と不活性担体とを含有することを特徴とする細胞外マトリックス遺伝子転写抑制組成物。
１３．前項５及び１１記載の化合物と不活性担体とを含有することを特徴とする細胞外マトリックス遺伝子転写抑制組成物。
１４．細胞外マトリックス遺伝子の転写を抑制するための有効成分としての、前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物の使用。
１５．細胞外マトリックス遺伝子の転写を抑制するための有効成分としての、前項２〜６、１０及び１１記載の化合物の使用。
１６．細胞外マトリックス遺伝子の転写を抑制するための有効成分としての、前項５及び１１記載の化合物の使用。
１７．細胞外マトリックス遺伝子の発現量を減少させて細胞外マトリックス蓄積量の低下を導くことにより組織の線維化を改善するための有効成分としての、前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物の使用。
１８．細胞外マトリックス遺伝子の発現量を減少させて細胞外マトリックス蓄積量の低下を導くことにより組織の線維化を改善するための有効成分としての、前項２〜６、１０及び１１記載の化合物の使用。
１９．有効量の、前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物を、組織の線維化を改善させる処置を必要とする哺乳動物患者に投与することを特徴とする組織線維化改善方法。
２０．有効量の前項２〜６、１０及び１１記載の化合物を、組織の線維化を改善させる処置を必要とする哺乳動物患者に投与することを特徴とする組織線維化改善方法。
２１．前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物、又は、前項２〜６、１０及び１１記載の化合物と、不活性担体とを含有することを特徴とする慢性腎不全治療剤。
２２．慢性腎不全を治療するための有効成分としての、前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物、又は、前項２〜６、１０及び１１記載の化合物の使用。
２３．有効量の、前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物、又は、前項２〜６、１０及び１１記載の化合物を、慢性腎不全治療処置を必要とする哺乳動物患者に投与することを特徴とする慢性腎不全治療方法。
２４．前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物、又は、前項２〜６、１０及び１１記載の化合物と、不活性担体とを含有することを特徴とする心不全治療剤。
２５．心不全を治療するための有効成分としての、前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物、又は、前項２〜６、１０及び１１記載の化合物の使用。
２６．有効量の、前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物、又は、前項２〜６、１０及び１１記載の化合物を、心不全治療処置を必要とする哺乳動物患者に投与することを特徴とする心不全治療方法。
２７．前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物と不活性担体とを含有することを特徴とするＴＧＦ−β作用抑制組成物。
２８．前項２〜６、１０及び１１記載の化合物と不活性担体とを含有することを特徴とするＴＧＦ−β作用抑制組成物。
２９．ＴＧＦ−βの作用を抑制するための有効成分としての、前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物の使用。
３０．ＴＧＦ−βの作用を抑制するための有効成分としての、前項２〜６、１０及び１１記載の化合物の使用。
３１．前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物、又は、前項２〜６、１０及び１１記載の化合物と、不活性担体とを含有することを特徴とする養毛組成物。
３２．ＴＧＦ−βによる毛髪退行期への移行促進を阻害して毛髪成長期の延長を導くことにより養毛効果を得るための有効成分としての、前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物、又は、前項２〜６、１０及び１１記載の化合物の使用。
３３．有効量の、前項１及び９記載の組成物に有効成分として含有されるシンナモイル化合物、又は、前項２〜６、１０及び１１記載の化合物を、養毛処置を必要とする哺乳動物患者に投与することを特徴とする養毛方法；
等を提供するものである。 As a result of intensive studies under these circumstances, the present inventors have found that compounds represented by the following formulas (I) to (VI) (I ′), (II ′) and (V ′) are extracellular matrix genes. It has been found that it has the ability to suppress transcription, and has led to the present invention.
That is, the present invention
1. Formula (I)

[Where:
I. α represents an aromatic 5-membered ring or an aromatic 6-membered ring having two or more nitrogen atoms, and (Y _α ) _q Y _α Is the following X ₀ Group or Y ₀ Represents a group of groups, q represents 0, 1, 2 or 3, and when q is 2 or more, Y _α Are the same or different, and when q is 2 or more, two adjacent Y same or different Y _α Is Z ₀ It may be condensed with an α ring as a group, and (X _α ) _p X _α Is the following X ₀ Group, Y ₀ Group and Z ₀ Represents a substituent not belonging to the group, p represents 0, 1, 2 or 3, and when p is 2 or more, X _α Are the same or different, and the sum of p and q is 3 or less.
(1) X ₀ Group: M _a -Group [M _a Is R _b -Group (R _b Represents a C1-C10 alkyl group which may be substituted with a halogen atom. ), Halogen atom, nitro group, cyano group, hydroxyl group, R _c -B _a -R _d -Group (R _c Represents a C1-C10 alkyl group which may be substituted with a halogen atom; _a Represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group, and R _d Represents a single bond or a C1-C10 alkylene group. ), HOR _d -Group (R _d Represents the same meaning as described above. ), R _e -CO-R _d -Group (R _e Represents a hydrogen atom or a C1-C10 alkyl group which may be substituted with a halogen atom; _d Represents the same meaning as described above. ), R _e -CO-O-R _d -Group (R _e And R _d Represents the same meaning as described above. ), R _e O-CO-R _d -Group (R _e And R _d Represents the same meaning as described above. ), HO—CO—CH═CH— group, R _e R _e 'N-R _d -Group (R _e And R _e 'Is the same or different, R _e Represents the same meaning as above, R _e 'R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _e -CO-NR _e '-R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), R _b O-CO-N (R _e -R _d -Group (R _b , R _e And R _d Represents the same meaning as described above. ), R _e R _e 'N-CO-R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), R _e R _e 'N-CO-NR _e '' -R _d -Group (R _e , R _e 'And R _e '' Is the same or different, R _e And R _e 'Represents the same meaning as described above, and R _e '' Is R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _e R _e 'N-C (= NR _e '') -NR _e '''-R _d -Group (R _e , R _e ', R _e '' And R _e '''Is the same or different, R _e , R _e 'And R _e '' Represents the same meaning as above, R _e '''Is R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _b -SO ₂ -NR _e -R _d -Group (R _b , R _e And R _d Represents the same meaning as described above. ), R _e R _e 'N-SO ₂ -R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), A C2-C10 alkenyl group or a C2-C10 alkynyl group. ].
(2) Y ₀ Group: M _b0 -R _d -Group [M _b0 Is M _c0 -Group {M _c0 Is M _d0 -R _d '-Group {M _d0 Is M _a -Group (M _a Represents the same meaning as described above. 6-10 membered aryl group optionally substituted with M), or M _a -Group (M _a Represents the same meaning as described above. 5-10 membered heteroaryl group optionally substituted with M), or M _a -Group (M _a Represents the same meaning as described above. 3-10-membered hydrocarbon ring or heterocyclic group which may contain an unsaturated bond which may be substituted, or

(b ₀ ) -Group ((b ₀ ) G ₀ Forms a saturated or unsaturated, non-aromatic, 5- to 14-membered hydrocarbon ring or heterocyclic ring which may have a substituent. ),

(C ₀ ) -Group ((c ₀ ) ₀ May contain a nitrogen atom and form an aromatic 5- to 7-membered ring. ),

(D ₀ ) -Group {d ₀ Is substituted with a carbonyl group or a thiocarbonyl group, and further, an oxy group, a thio group, —NR ₁ -Group {R ₁ Is a hydrogen atom, a C1-C10 alkyl group, a halogen atom or R ₂ -B ₁ -Group (R ₂ Represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl group; ₁ Represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group. ) Represents a C2-C10 alkyl group, a C3-C10 alkenyl group, or a C3-C10 alkynyl group. }, A 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group. } Or

(E ₀ ) -Group {e ₀ Is a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, -NR ₁ -Group (R ₁ Represents the same meaning as described above. ), A 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group. }, R _d 'R _d Same or different from R _d Represents the same meaning as }. }, M _c0 -B _a -Group (M _c0 And B _a Represents the same meaning as described above. ), M _c0 —CO— group (M _c0 Represents the same meaning as described above. ), M _c0 -CO-O- group (M _c0 Represents the same meaning as described above. ), M _c0 O-CO- group (M _c0 Represents the same meaning as described above. ), M _c0 R _e N-group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 -CO-NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 O-CO-NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 R _e N-CO- group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 R _e N-CO-NR _e '-Group (M _c0 , R _e And R _e 'Represents the same meaning as described above. ), M _c0 R _e N-C (= NR _e ') -NR _e '' -Group (M _c0 , R _e , R _e 'And R _e '' Represents the same meaning as described above. ), M _c0 -SO ₂ -NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ) Or M _c0 R _e N-SO ₂ -Group (M _c0 And R _e Represents the same meaning as described above. ) And R _d Represents the same meaning as described above. ].
(3) Z ₀ Group: may have a halogen atom, C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group, A 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring and a group condensed with the α ring.
II. β is
Formula (I-1)

[Where:
(1) Q _α Represents an optionally substituted hydroxyl group or an optionally substituted amino group.
(2) W _α Is an oxygen atom or -NT _α -Group (T _α Represents a hydrogen atom or a substituent on a nitrogen atom. ).
(3) K _α And L _α Are the same or different and each represents a hydrogen atom or a substituent on a carbon atom; _α And L _α And may be a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (I-2)

[Where T _α Represents the same meaning as described above, and L _β Represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (I-3)

[Where T _α Represents the same meaning as described above, and L _γ Represents a C1-C10 alkyl group. ]
A group represented by
Formula (I-4)

[Where T _α Represents the same meaning as described above. ]
A group represented by
Formula (I-5)

[Where T _α Represents the same meaning as described above, and K _β Represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (I-6)

[Where W _α Represents the same meaning as described above, and K _γ And L _δ Is a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (I-7)

[Where Q _α And W _α Represents the same meaning as described above, and K _δ And L _ε Is -V _α = V _α '-V _α '' = V _α '''-Group (V _α , V _α ', V _α '' And V _α '''Represents the same or different methine group which may be substituted, or -N = group, and V _α , V _α ', V _α '' And V _α At least one of '''represents a -N = group. ). ]
A group represented by
Formula (I-8)

[Where T _α Represents the same meaning as above, Q _β Represents a hydroxyl group which may be substituted. ]
Or a group represented by
Formula (I-9)

[Where U and W _α Represents the same meaning as described above. ]
Represents a group represented by
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A composition for inhibiting transcription of an extracellular matrix gene, comprising a cinnamoyl compound represented by the formula (1) and an inert carrier.
2. Formula (II)

(E ₀ ) -Group {e ₀ Is a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, -NR ₁ -Group (R ₁ Represents the same meaning as described above. ), A 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group. }, R _d 'R _d Same or different from R _d Represents the same meaning as }. }, M _c0 -B _a -Group (M _c0 And B _a Represents the same meaning as described above. ), M _c0 —CO— group (M _c0 Represents the same meaning as described above. ), M _c0 -CO-O- group (M _c0 Represents the same meaning as described above. ), M _c0 O-CO- group (M _c0 Represents the same meaning as described above. ), M _c0 R _e N-group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 -CO-NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 O-CO-NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 R _e N-CO- group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 R _e N-CO-NR _e '-Group (M _c0 , R _e And R _e 'Represents the same meaning as described above. ), M _c0 R _e N-C (= NR _e ') -NR _e '' -Group (M _c0 , R _e , R _e 'And R _e '' Represents the same meaning as described above. ), M _c0 -SO ₂ -NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ) Or M _c0 R _e N-SO ₂ -Group (M _c0 And R _e Represents the same meaning as described above. ) And R _d Represents the same meaning as described above. ].
(3) Z ₀ Group: may have a halogen atom, C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group, A 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring and a group condensed with the α ring.
II. β is
Formula (II-1)

[Where:
(1) Q _α Represents an optionally substituted hydroxyl group or an optionally substituted amino group.
(2) W _α Is an oxygen atom or -NT _α -Group (T _α Represents a hydrogen atom or a substituent on a nitrogen atom. ).
(3) K _α And L _α Are the same or different and each represents a hydrogen atom or a substituent on a carbon atom; _α And L _α And may be a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (II-2)

[Where T _α Represents the same meaning as described above, and L _β Represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (II-3)

[Where T _α Represents the same meaning as described above, and L _γ Represents a C1-C10 alkyl group. ]
A group represented by
Formula (II-4)

[Where T _α Represents the same meaning as described above. ]
A group represented by
Formula (II-5)

[Where T _α Represents the same meaning as described above, and K _β Represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (II-6)

[Where W _α Represents the same meaning as described above, and K _γ And L _δ Is a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (II-7)

[Where Q _α And W _α Represents the same meaning as described above, and K _δ And L _ε Is -V _α = V _α '-V _α '' = V _α '''-Group (V _α , V _α ', V _α '' And V _α '''Represents the same or different methine group which may be substituted, or -N = group, and V _α , V _α ', V _α '' And V _α At least one of '''represents a -N = group. ). ]
A group represented by
Formula (II-8)

[Where T _α Represents the same meaning as above, Q _β Represents a hydroxyl group which may be substituted. ]
Or a group represented by
Formula (II-9)

[Where U and W _α Represents the same meaning as described above. ]
Represents a group represented by
However, when α is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:
3. Formula (III)

[Where:
I. A0 represents an aromatic 5-membered ring or an aromatic 6-membered ring having two or more nitrogen atoms.
II. (X _A0 ) _p X _A0 Is the following A ₀ N from the group ₀ Represents a group included in any group up to the group, p represents 0, 1, 2 or 3, and when p is 2 or more, X _A0 Are the same or different.
(1) A ₀ Group: D ₁ -R ₄ -Group [D ₁ (R ₁ -(O) _k -) A ₁ N- (O) _{k '} -Group {R ₁ Is a hydrogen atom, a C1-C10 alkyl group, a halogen atom or R ₂ -B ₁ -Group (R ₂ Represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl group; ₁ Represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group. ) Represents a C2-C10 alkyl group, a C3-C10 alkenyl group, or a C3-C10 alkynyl group, and k represents 0 or 1; ₁ Is R ₃ -(CHR ₀ ) _m -(B ₂ -B ₃ ) _{m '} -Group {R ₃ Is a hydrogen atom, a halogen atom or R ₂ -B ₁ -Group (R ₂ And B ₁ Represents the same meaning as described above. ) Represents a C1-C10 alkyl group, a C2-C10 alkenyl group, or a C2-C10 alkynyl group optionally substituted by R) ₀ Represents a hydrogen atom, a C1-C10 alkyl group or a C2-C10 haloalkyl group, m represents 0 or 1, B ₂ Is a single bond, an oxy group, a thio group or —N ((O) _n R ₁ ') -Group (R ₁ 'R ₁ Same or different from R ₁ And n represents 0 or 1. ) And B ₃ Represents a carbonyl group, a thiocarbonyl group or a sulfonyl group, m ′ represents 0 or 1, and B ₃ When is a sulfonyl group, m is 0 and R ₃ Does not become a hydrogen atom. }, And k ′ represents 0 or 1. }, R ₄ Represents a C1-C10 alkylene group. However, R ₀ 'R ₀ '' N-R ₄ -Group (R ₀ 'And R ₀ '' Is R ₀ Same or different from R ₀ Represents the same meaning as R ₄ Represents the same meaning as described above. )except for. ], D ₂ -R ₄ -Group [D ₂ Is a cyano group, R ₁ R ₁ 'NC (= N- (O) _n -A ₁ ) -Group (R ₁ , R ₁ ', N, and A ₁ Represents the same meaning as described above. ), A ₁ N = C (-OR ₂ ) -Group (A ₁ And R ₂ Represents the same meaning as described above. Or NH ₂ Represents -CS- group, R ₄ Represents the same meaning as described above. ], D ₃ -R ₄ -Group {D ₃ Is a nitro group or R ₁ OSO ₂ -Group (R ₁ Represents the same meaning as described above. ) And R ₄ Represents the same meaning as described above. } Or R ₁ OSO ₂ -Group (R ₁ Represents the same meaning as described above. ).
(2) B ₀ group:

(A ₀ ) -Group
((A ₀ ) In E ₀ Is a saturated or unsaturated, aromatic or non-aromatic 5- to 14-membered hydrocarbon ring or heterocyclic ring which may have a substituent, R ₁ Represents the same meaning as described above. ).
(3) C ₀ Group: Halogen atom, R ₂ -B ₁ -Group (R ₂ And B ₁ Represents the same meaning as described above. ), D ₄ -R ₄ -Group [D ₄ Is a hydroxyl group or A ₁ —O— group (A ₁ Represents the same meaning as described above. ) And R ₄ Represents the same meaning as described above. ], D ₅ -Group [D ₅ Is O = C (R ₃ ) -Group (R ₃ Represents the same meaning as described above. ), A ₁ -(O) _n -N = C (R ₃ ) -Group (A ₁ , N and R ₃ Represents the same meaning as described above. ), R ₁ -B ₀ -CO-R ₄ -(O) _n -N = C (R ₃ ) -Group {R ₁ , R ₄ , N and R ₃ Represents the same meaning as above, B ₀ Is an oxy group, a thio group or -N ((O) _m R ₁ ') -Group (R ₁ 'And m represent the same meaning as described above. ). }, D ₂ -R ₄ -(O) _n -N = C (R ₃ ) -Group (D ₂ , R ₄ , N and R ₃ Represents the same meaning as described above. Or R ₁ A ₁ N−N = C (R ₃ ) -Group (R ₁ , A ₁ And R ₃ Represents the same meaning as described above. ). ], R ₁ A ₁ N-O-R ₄ -Group (R ₁ , A ₁ And R ₄ Represents the same meaning as described above. ), R ₁ (A ₁ -(O) _n -) N-group (R ₁ , A ₁ And n represent the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. Or D ₃ -Group (D ₃ Represents the same meaning as described above. C2-C10 alkenyl group substituted with
It is.
(4) D ₀ group:

(b ₀ -R ₄ -Group ((b ₀ ) G ₀ Forms a saturated or unsaturated, non-aromatic, 5- to 14-membered hydrocarbon ring or heterocyclic ring which may have a substituent. ),

(C ₀ -R ₄ -Group
((C ₀ ) ₀ May contain a nitrogen atom, form an aromatic 5-7 membered ring, R ₄ Represents the same meaning as described above. ), Halogen atom, R ₂ -B ₁ -R ₄ -Group (R ₂ , B ₁ And R ₄ Represents the same meaning as described above. ), D ₄ -R ₄ -Group (D ₄ And R ₄ Represents the same meaning as described above. ), D ₅ -Group (D ₅ Represents the same meaning as described above. ), D ₁ -R ₄ -Group (D ₁ And R ₄ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. Or D ₃ -R ₄ -Group (D ₃ And R ₄ Represents the same meaning as described above. C2-C10 alkynyl group substituted with
It is.
(5) E ₀ Group: A ₂ -CO-R ₅ -Group
It is. However, A ₂ When R is a hydroxyl group, R ₅ Is not a vinylene group.
[A ₂ Is
(i) A ₃ -B ₄ -Group
{A ₃ Is a hydrogen atom, a C1-C10 alkyl group, a C2-C10 haloalkyl group, a C2-C10 alkenyl group optionally substituted with a halogen atom, or a C3-C10 optionally substituted with a halogen atom. Alkynyl group or R _a0 -(R ₄ ) _m -Group (R _a0 Represents an optionally substituted 5-7 membered aryl or heteroaryl group, R ₄ And m represent the same meaning as described above. ) Or (b ₀ -R ₄ -Group ((b ₀ ) And R ₄ Represents the same meaning as described above. ), (C ₀ -R ₄ -Group ((c ₀ ) And R ₄ Represents the same meaning as described above. ), R ₂ -B ₁ -R ₄ -Group (R ₂ , B ₁ And R ₄ Represents the same meaning as described above. ), D ₄ -R ₄ -Group (D ₄ And R ₄ Represents the same meaning as described above. ), D ₅ -Group (D ₅ Represents the same meaning as described above. ), D ₁ -R ₄ -Group (D ₁ And R ₄ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. ), D ₃ -R ₄ -Group (D ₃ And R ₄ Represents the same meaning as described above. Or A ₄ -SO ₂ -R ₄ -Group {A ₄ (B ₀ ) -Group ((b ₀ ) Represents the same meaning as described above. ), (C ₀ ) -Group ((c ₀ ) Represents the same meaning as described above. Or R ₁ R ₁ 'N-group (R ₁ And R ₁ 'Represents the same meaning as described above. ) And R ₄ Represents the same meaning as described above. } Represents a C1-C10 alkyl group substituted with
B ₄ Is an oxy group, a thio group or -N ((O) _m R ₁ ) -Group (R ₁ And m represent the same meaning as described above. ). However, B ₄ When is a thio group, A ₃ Is not a hydrogen atom. },
(ii) R ₁ -B ₄ -CO-R ₄ -B ₄ '-Group (R ₁ , B ₄ And R ₄ Represents the same meaning as above, B ₄ 'B ₄ Same or different from B ₄ Represents the same meaning as However, B ₄ When is a thio group, R ₂ Is not a hydrogen atom. Or D ₂ -R ₄ -B ₄ -Group (D ₂ , R ₄ And B ₄ Represents the same meaning as described above. ),
(iii) R ₂ -SO ₂ -NR ₁ -Group (R ₂ Represents the same meaning as described above. However, a hydrogen atom is excluded. R ₁ Represents the same meaning as described above. ),
(iv) (b ₀ ) -Group ((b ₀ ) Represents the same meaning as described above. ),
(v) (c ₀ ) -Group ((c ₀ ) Represents the same meaning as described above. Or
(vi) R ₁ A ₁ N-NR ₁ '-Group (R ₁ , A ₁ And R ₁ 'Represents the same meaning as described above. ) And R ₅ Represents a C2-C10 alkenylene group or a C2-C10 alkynylene group which may be substituted with a halogen atom. ]
(6) F ₀ Group: A ₅ -B ₅ -R ₆ -Group [A ₅ D ₄ -Group (D ₄ Represents the same meaning as described above. ), D ₁ -Group (D ₁ Represents the same meaning as described above. ), D ₃ -Group (D ₃ Represents the same meaning as described above. Or A ₄ -SO ₂ -Group (A ₄ Represents the same meaning as described above. Or a C2-C10 alkyl group substituted with R) or R ₂ -B ₁ -Group (R ₂ And B ₁ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. ), D ₅ -Group (D ₅ Represents the same meaning as described above. Or A ₂ -CO- group (A ₂ Represents the same meaning as described above. ) Represents a C1-C10 alkyl group substituted with ₅ Is B ₁ -Group (B ₁ Represents the same meaning as described above. ) Or -NA ₁ -Group (A ₁ Represents the same meaning as described above. ) And R ₆ Represents a single bond or a C1-C10 alkylene group. ]
It is.
(7) G ₀ Group: A ₆ -B ₅ -R ₆ -Group
[A ₆ (A ₀ -R ₄ -Group ((a ₀ ) And R ₄ Represents the same meaning as described above. ), A C2-C10 alkenyl group, a C2-C10 alkynyl group, a halogen atom, R ₂ -B ₁ -Group (R ₂ And B ₁ Represents the same meaning as described above. ), D ₅ -Group (D ₅ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. Or A ₂ -CO- group (A ₂ Represents the same meaning as described above. ) Substituted C2-C10 alkenyl group, or halogen atom, R ₂ -B ₁ -Group (R ₂ And B ₁ Represents the same meaning as described above. ), D ₅ -Group (D ₅ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. Or A ₂ -CO- group (A ₂ Represents the same meaning as described above. ) Substituted C2-C10 alkynyl group, or (b ₀ ) -Group ((b ₀ ) Represents the same meaning as described above. ), (C ₀ ) -Group ((c ₀ ) Represents the same meaning as described above. ), D ₄ -Group (D ₄ Represents the same meaning as described above. ), D ₁ -Group (D ₁ Represents the same meaning as described above. Or D ₃ -Group (D ₃ Represents the same meaning as described above. C3-C10 alkenyl group substituted with) or D ₄ -Group (D ₄ Represents the same meaning as described above. ), D ₁ -Group (D ₁ Represents the same meaning as described above. Or D ₃ -Group (D ₃ Represents the same meaning as described above. ) Represents a C3-C10 alkynyl group substituted with ₅ And R ₆ Represents the same meaning as described above. ]
It is.
(8) H ₀ group:
D ₂ -N (-(O) _n -A ₁ -R ₆ -Group (D ₂ , N, A ₁ And R ₆ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. However, the cyano group is excluded. ), R ₁ (R ₁ '(O) _n ) N-CR ₁ '' = N-R ₆ -Group (R ₁ , R ₁ ', N and R ₆ Represents the same meaning as above, R ₁ '' Is R ₁ Same or different from R ₁ Represents the same meaning as ), R ₁ -(O) _n -N = CR ₁ '-NR ₂ -R ₆ -Group (R ₁ , N, R ₁ ', R ₂ And R ₆ Represents the same meaning as described above. ), R ₂ -B ₃ -NR ₁ -CO-NR ₁ '-R ₆ -Group (R ₂ , B ₃ , R ₁ , R ₁ 'And R ₆ Represents the same meaning as described above. ), D ₂ -CO-NR ₁ -R ₆ -Group (D ₂ , R ₁ And R ₆ Represents the same meaning as described above. ) Or A ₂ -COCO-NR ₁ -R ₆ -Group (A ₂ , R ₁ And R ₆ Represents the same meaning as described above. )
It is.
(9) I ₀ group:
A ₇ -B ₆ -N ((O) _n R ₁ -R ₆ -Group [A ₇ Is a C2-C10 alkenyl group, C2-C10 alkynyl group, C3-C10 haloalkynyl group, R which may be substituted with a halogen atom, ₂ -B ₁ -R ₄ -Group (R ₂ , B ₁ And R ₄ Represents the same meaning as described above. ), D ₄ -R ₄ -Group (D ₄ And R ₄ Represents the same meaning as described above. ), D ₅ -R ₄ -Group (D ₅ And R ₄ Represents the same meaning as described above. ), D ₁ -R ₄ -Group (D ₁ And R ₄ Represents the same meaning as described above. ), (B ₀ -R ₄ -Group ((b ₀ ) And R ₄ Represents the same meaning as described above. ), (C ₀ -R ₄ -Group ((c ₀ ) And R ₄ Represents the same meaning as described above. ), D ₂ -R ₄ -Group (D ₂ And R ₄ Represents the same meaning as described above. ), D ₃ -R ₄ -Group (D ₃ And R ₄ Represents the same meaning as described above. ), A ₄ -SO ₂ -R ₄ -Group (A ₄ And R ₄ Represents the same meaning as described above. ) Or A ₂ -CO-R ₄ -Group (A ₂ And R ₄ Represents the same meaning as described above. ) And B ₆ Represents a carbonyl group or a thiocarbonyl group, and n, R ₁ And R ₆ Represents the same meaning as described above. ], A ₈ -CS-N ((O) _n R ₁ -R ₆ -Group [A ₈ Represents a hydrogen atom or a C1-C10 alkyl group which may be substituted with a halogen atom, and n, R ₁ And R ₆ Represents the same meaning as described above. ],
A ₇ '-B ₂ '-B ₃ -N ((O) _n R ₁ -R ₆ -Group [A ₇ 'Is a C3-C10 alkenyl group which may be substituted with a halogen atom, a C3-C10 alkynyl group which may be substituted with a halogen atom, R ₂ -B ₁ -R ₄ '-Group (R ₂ And B ₁ Represents the same meaning as above, R ₄ 'Represents a C2-C10 alkylene group. ), D ₄ -R ₄ '-Group (D ₄ And R ₄ 'Represents the same meaning as described above. ), D ₁ -R ₄ '-Group (D ₁ And R ₄ 'Represents the same meaning as described above. ), (B ₀ -R ₄ '-Group ((b ₀ ) And R ₄ 'Represents the same meaning as described above. ), (C ₀ -R ₄ '-Group ((c ₀ ) And R ₄ 'Represents the same meaning as described above. ), D ₂ -R ₄ -Group (D ₂ And R ₄ Represents the same meaning as described above. ), D ₃ -R ₄ '-Group (D ₃ And R ₄ 'Represents the same meaning as described above. ) Or A ₂ -CO-R ₄ -Group (A ₂ And R ₄ Represents the same meaning as described above. ) And B ₂ 'Represents an oxy group, a thio group, or -N ((O) _{n '} R ₁ ') -Group (n' is the same as or different from n and represents the same meaning as n, R ₁ 'Represents the same meaning as described above. ) And B ₃ , N, R ₁ And R ₆ Represents the same meaning as described above. ], A ₈ '-B ₂ '-CS-N ((O) _n R ₁ -R ₆ -Group [A ₈ 'Represents a C1-C10 alkyl group or a C2-C10 haloalkyl group, and B ₂ 'Represents the same meaning as described above, and n, R ₁ And R ₆ Represents the same meaning as described above. ], A ₈ '-SB ₃ '-N ((O) _n R ₁ -R ₆ -Group [A ₈ ', N, R ₁ And R ₆ Represents the same meaning as above, B ₃ 'Represents a carbonyl group or a sulfonyl group. ] Or A ₇ '' -SO ₂ -N ((O) _n R ₁ -R ₆ -Group [A ₇ '' Is a C2-C10 alkenyl group, a C3-C10 alkenyl group substituted with a halogen atom, a C3-C10 alkynyl group optionally substituted with a halogen atom, R ₂ -B ₁ -R ₄ '-Group (R ₂ , B ₁ And R ₄ 'Represents the same meaning as described above. ), D ₄ -R ₄ '-Group (D ₄ And R ₄ 'Represents the same meaning as described above. ), D ₅ -R ₄ -Group (D ₅ And R ₄ Represents the same meaning as described above. ), D ₁ -R ₄ '-Group (D ₁ And R ₄ 'Represents the same meaning as described above. ), (B ₀ -R ₄ '-Group ((b ₀ ) And R ₄ 'Represents the same meaning as described above. ), (C ₀ -R ₄ '-Group ((c ₀ ) And R ₄ 'Represents the same meaning as described above. ), D ₂ -R ₄ -Group (D ₂ And R ₄ Represents the same meaning as described above. ), NO ₂ -R ₄ -Group (R ₄ Represents the same meaning as described above. ) Or A ₂ -CO-R ₄ -Group (A ₂ And R ₄ Represents the same meaning as described above. ), N, R ₁ And R ₆ Represents the same meaning as described above. ]
It is.
(10) J ₀ Group: A ₇ -CO- group (A ₇ Represents the same meaning as described above. ) Or A ₉ -CS- group (A ₉ A ₇ Or A ₈ Represents. ) Or A ₉ '(O) _m N = C (A ₉ ) -Group (A ₉ 'A ₇ 'Or A ₈ 'And m and A ₉ Represents the same meaning as described above. ) Or D ₂ —CO— group (D ₂ Represents the same meaning as described above. ) Or A ₂ -COCO- group (A ₂ Represents the same meaning as described above. ) Or A ₉ -CO-B ₁ '-R ₆ -Group (A ₉ And R ₆ Represents the same meaning as above, B ₁ 'Represents an oxy group or a thio group. However, B ₁ When 'is an oxy group, A ₉ A ₈ is not. ) Or A ₉ -CS-B ₁ '-R ₆ -Group (A ₉ , B ₁ 'And R ₆ Represents the same meaning as described above. ) Or A ₇ '' -SO ₂ -B ₁ '-R ₆ -Group (A ₇ '' 、 B ₁ 'And R ₆ Represents the same meaning as described above. ) Or A ₈ -SO ₂ -B ₁ '-R ₆ -Group (A ₈ , B ₁ 'And R ₆ Represents the same meaning as described above. However, A ₈ Does not become a hydrogen atom. ) Or A ₉ '-B ₂ '-B ₃ -B ₁ '-R ₆ -Group (A ₉ ', B ₂ ', B ₃ , B ₁ 'And R ₆ Represents the same meaning as described above. ) Or (b ₀ ) -Group ((b ₀ ) Represents the same meaning as described above. ) Or (c ₀ ) -Group ((c ₀ ) Represents the same meaning as described above. C2-C10 alkenyl group substituted with
It is.
(11) K ₀ Group: A ₁₀ -N ((O) _n R ₁ ) -CO-R ₆ -Group [A ₁₀ Is a hydrogen atom (where n is not 0), A ₇ '' -SO ₂ -Group (A ₇ '' Represents the same meaning as described above. ), A ₈ -SO ₂ -Group (A ₈ Represents the same meaning as described above. However, A ₈ Does not become a hydrogen atom. ), A ₉ 'O-group (A ₉ 'Represents the same meaning as described above. However, n is not 1. ), A ₉ '-Group (A ₉ 'Represents the same meaning as described above. However, when n is 0, A ₈ 'except for. ), R ₂ OCH ₂ -Group (R ₂ Represents the same meaning as described above. ), A ₂ -CO-R ₄ -Group (A ₂ And R ₄ Represents the same meaning as described above. ) Or A ₂ -CO-CH (CH ₂ CO-A ₂ ) -Group (A ₂ Represents the same meaning as described above. ), N, R ₁ And R ₆ Represents the same meaning as described above. ]
It is.
(12) L ₀ Group: A ₁₀ '-N ((O) _n R ₁ -SO ₂ -R ₆ -Group [A ₁₀ 'Is a hydrogen atom (where n is not 0), A ₉ 'O-group (A ₉ 'Represents the same meaning as described above. However, n is not 1. ), A ₉ '-Group (A ₉ 'Represents the same meaning as described above. However, when n is 0, A ₈ 'except for. ), R ₂ —CO— group (R ₂ Represents the same meaning as described above. ), A ₂ -CO-R ₄ -Group (A ₂ And R ₄ Represents the same meaning as described above. ) Or A ₂ -CO-CH (CH ₂ CO-A ₂ ) -Group (A ₂ Represents the same meaning as described above. ), N, R ₁ And R ₆ Represents the same meaning as described above. ], A ₉ '' R ₁ N-SO ₂ -N ((O) _n R ₁ ') -R ₆ -Group [A ₉ '' Is a hydrogen atom or A ₉ '-Group (A ₉ 'Represents the same meaning as described above. ) And R ₁ , N, R ₁ 'And R ₆ Represents the same meaning as described above. ] Or (b ₀ -SO ₂ -N ((O) _n R ₁ ') -R ₆ -Group [(b ₀ ), N, R ₁ 'And R ₆ Represents the same meaning as described above. ]
It is.
(13) M ₀ Group: R ₁ (R ₂ S) C = N-R ₆ -Group (R ₁ , R ₂ And R ₆ Represents the same meaning as described above. ), R ₂ B (R ₂ 'B') C = N-R ₆ -Group (R ₂ And R ₆ Represents the same meaning as above, R ₂ 'R ₂ Same or different from R ₂ And B and B ′ are the same or different and represent an oxy group or a thio group. ), R ₁ R ₁ 'N- (R ₂ S) C = N-R ₆ -Group (R ₁ , R ₁ ', R ₂ And R ₆ Represents the same meaning as described above. ), R ₁ N = C (SR ₂ -NR ₂ '-R ₆ -Group (R ₁ , R ₂ , R ₂ 'And R ₆ Represents the same meaning as described above. Or R ₁ (R ₁ 'O) N-R ₆ -Group (R ₁ , R ₁ 'And R ₆ Represents the same meaning as described above. )
It is.
(14) N ₀ Group: A ₁₁ -P (= O) (OR ₁ ') -R ₄ -Group [A ₁₁ Is R ₁ -Group (R ₁ Represents the same meaning as described above. ), R ₁ O-R ₆ -Group (R ₁ And R ₆ Represents the same meaning as described above. Or R ₁ OCO-CHR ₀ -Group (R ₁ And R ₀ Represents the same meaning as described above. ) And R ₁ 'And R ₄ Represents the same meaning as described above. ]
It is.
III. (Y _A0 ) _q Y _A0 Is the following X ₀ Group and Y ₀ Represents a group of groups, q represents 0, 1, 2 or 3, the sum of p (p represents the same meaning as described above) and q is 3 or less, and q is 2 or more , Y _A0 Are the same or different, and when q is 2 or more, two adjacent Y same or different Y _A0 Is Z ₀ A group may be formed to be condensed with the A0 ring.
(1) X ₀ group:
M _a -Group [M _a Is R _b -Group (R _b Represents a C1-C10 alkyl group which may be substituted with a halogen atom. ), Halogen atom, nitro group, cyano group, hydroxyl group, R _c -B _a -R _d -Group (R _c Represents a C1-C10 alkyl group which may be substituted with a halogen atom; _a Represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group, and R _d Represents a single bond or a C1-C10 alkylene group. ), HOR _d -Group (R _d Represents the same meaning as described above. ), R _e -CO-R _d -Group (R _e Represents a hydrogen atom or a C1-C10 alkyl group which may be substituted with a halogen atom; _d Represents the same meaning as described above. ), R _e -CO-O-R _d -Group (R _e And R _d Represents the same meaning as described above. ), R _e O-CO-R _d -Group (R _e And R _d Represents the same meaning as described above. ), HO—CO—CH═CH— group, R _e R _e 'N-R _d -Group (R _e And R _e 'Is the same or different, R _e Represents the same meaning as above, R _e 'R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _e -CO-NR _e '-R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), R _b O-CO-N (R _e -R _d -Group (R _b , R _e And R _d Represents the same meaning as described above. ), R _e R _e 'N-CO-R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), R _e R _e 'N-CO-NR _e '' -R _d -Group (R _e , R _e 'And R _e '' Is the same or different, R _e And R _e 'Represents the same meaning as described above, and R _e '' Is R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _e R _e 'NC (= NR _e '') -NR _e '''-R _d -Group (R _e , R _e ', R _e '' And R _e '''Is the same or different, R _e , R _e 'And R _e '' Represents the same meaning as above, R _e '''Is R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _b -SO ₂ -NR _e -R _d -Group (R _b , R _e And R _d Represents the same meaning as described above. ), R _e R _e 'N-SO ₂ -R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), A C2-C10 alkenyl group or a C2-C10 alkynyl group. ].
(2) Y ₀ group:
M _b0 -R _d -Group [M _b0 Is M _c0 -Group {M _c0 Is M _d0 -R _d '-Group {M _d0 Is M _a -Group (M _a Represents the same meaning as described above. 6-10 membered aryl group optionally substituted with M), or M _a -Group (M _a Represents the same meaning as described above. 5-10 membered heteroaryl group optionally substituted with M), or M _a -Group (M _a Represents the same meaning as described above. 3-10-membered hydrocarbon ring or heterocyclic group which may contain an unsaturated bond which may be substituted, or

(b ₀ ) -Group ((b ₀ ) Represents the same meaning as described above. ),

(C ₀ ) -Group ((c ₀ ) Represents the same meaning as described above. ),

(D ₀ ) -Group {d ₀ Is substituted with a carbonyl group or a thiocarbonyl group, and further, an oxy group, a thio group, —NR ₁ -Group (R ₁ Represents the same meaning as described above. ), A 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group. } Or

(E ₀ ) -Group {e ₀ Is a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, -NR ₁ -Group (R ₁ Represents the same meaning as described above. ), A 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group. }, R _d 'R _d Same or different from R _d Represents the same meaning as }. }, M _c0 -B _a -Group (M _c0 And B _a Represents the same meaning as described above. ), M _c0 —CO— group (M _c0 Represents the same meaning as described above. ), M _c0 -CO-O- group (M _c0 Represents the same meaning as described above. ), M _c0 O-CO- group (M _c0 Represents the same meaning as described above. ), M _c0 R _e N-group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 -CO-NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 O-CO-NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 R _e N-CO- group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 R _e N-CO-NR _e '-Group (M _c0 , R _e And R _e 'Represents the same meaning as described above. ), M _c0 R _e N-C (= NR _e ') -NR _e '' -Group (M _c0 , R _e , R _e 'And R _e '' Represents the same meaning as described above. ), M _c0 -SO ₂ -NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ) Or M _c0 R _e N-SO ₂ -Group (M _c0 And R _e Represents the same meaning as described above. ) And R _d Represents the same meaning as described above. ].
(3) Z ₀ Group: may have a halogen atom, C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group, A 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring, and a group condensed with the A0 ring.
IV. B0 is
Formula (III-1)

[Where:
(1) Q _A0 Is a hydroxyl group (b ₀ ) -Group ((b ₀ ) Represents the same meaning as described above. ), A ₉ -B ₆ -B _c -Group [A ₉ And B ₆ Represents the same meaning as above, B _c Is an oxy group or -N ((O) _m R ₁ ) -Group (m and R ₁ Represents the same meaning as described above. ). However, A ₉ When is a hydrogen atom, B _c Is not a sulfonyl group. ], A ₇ '' -SO ₂ -B _c -Group (A ₇ '' And B _c Represents the same meaning as described above. ), A ₈ -SO ₂ -B _c -Group (A ₈ And B _c Represents the same meaning as described above. However, A ₈ Does not become a hydrogen atom. ), R ₁ R ₁ 'N-SO ₂ -B _c -Group (R ₁ , R ₁ 'And B _c Represents the same meaning as described above. ), (B ₀ -SO ₂ -B _c -Group ((b ₀ ) And B _c Represents the same meaning as described above. ), A ₉ '-B _c -Group (A ₉ 'And B _c Represents the same meaning as described above. ), D ₅ -R ₄ -B _c -Group (D ₅ , R ₄ And B _c Represents the same meaning as described above. ), M _c0 -B ₃ -B _c -Group (M _c0 , B ₃ And B _c Represents the same meaning as described above. ) Or M _c0 -B _c -Group (M _c0 And B _c Represents the same meaning as described above. ).
(2) W _A0 Is an oxygen atom or -NT _A0 -Group [T _A0 Is a hydrogen atom, A ₉ '-Group (A ₉ 'Represents the same meaning as described above. ), D ₅ -R ₄ -Group (D ₅ And R ₄ Represents the same meaning as described above. ) Or M _c0 -Group (M _c0 Represents the same meaning as described above. ). ].
(3) K _A0 Represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group; _A0 Is a hydrogen atom, a C1-C10 alkyl group or M _b0 -Group (M _b0 Represents the same meaning as described above. ) And K _A0 And L _A0 Is a C3-C10 alkylene group, or a C4-C10 alkenylene group which may be substituted with one or a plurality of Ma-groups (Ma represents the same meaning as described above). is there. ]
A group represented by
Formula (III-2)

[Where T _A0 Represents the same meaning as described above, and L _B0 Represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (III-3)

[Where T _A0 Represents the same meaning as described above, and L _C0 Represents a C1-C10 alkyl group. ]
A group represented by
Formula (III-4)

[Where T _A0 Represents the same meaning as described above. ]
A group represented by
Formula (III-5)

[Where T _A0 Represents the same meaning as described above, and K _B0 Represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (III-6)

[Where W _A0 Represents the same meaning as described above, and K _C0 And L _D0 Is a C3-C10 alkylene group or a C4-C10 alkenylene group which may be substituted with one or a plurality of Ma-groups (Ma represents the same meaning as described above). ]
A group represented by
Formula (III-7)

[Where Q _A0 And W _A0 Represents the same meaning as described above, and K _D0 And L _E0 Is -V _A0 = V _A0 '-V _A0 '' = V _A0 '''-Group {V _A0 , V _A0 ', V _A0 '' And V _A0 '''Is the same or different, M _a -Group (M _a Represents the same meaning as described above. ) Represents a methine group which may be substituted, or -N = group, and V _A0 , V _A0 ', V _A0 '' And V _A0 At least one of '''represents a -N = group. }. ]
A group represented by
Formula (III-8)

[Where T _A0 Represents the same meaning as above, Q _B0 Is a hydroxyl group, A ₉ -B ₆ —O— group [A ₉ And B ₆ Represents the same meaning as described above. ], A ₇ '' -SO ₂ —O— group (A ₇ '' Represents the same meaning as described above. ), A ₈ -SO ₂ —O— group (A ₈ Represents the same meaning as described above. However, A ₈ Does not become a hydrogen atom. ), R ₁ R ₁ 'N-SO ₂ —O— group (R ₁ And R ₁ 'Represents the same meaning as described above. ), (B ₀ -SO ₂ —O— group ((b ₀ ) Represents the same meaning as described above. ), A ₉ '-O- group (A ₉ 'Represents the same meaning as described above. ), D ₅ -R ₄ —O— group (D ₅ And R ₄ Represents the same meaning as described above. ), M _c0 -B ₃ —O— group (M _c0 And B ₃ Represents the same meaning as described above. ) Or M _c0 —O— group (M _c0 Represents the same meaning as described above. ). ]
Or a group represented by
Formula (III-9)

[Where U and W _A0 Represents the same meaning as described above. ]
Represents a group represented by
However, when A0 is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:
4). Formula (IV)

[Where:
I. A represents an aromatic 5-membered ring or an aromatic 6-membered ring having two or more nitrogen atoms.
II. (X _A ) _p X _A Represents a group included in any of the following groups A to N, p represents 0, 1, 2 or 3, and when p is 2 or more, X represents _A Are the same or different.
(1) Group A: D ₁ -R ₄ -Group [D ₁ (R ₁ -(O) _k -) A ₁ N- (O) _{k '} -Group {R ₁ Is a hydrogen atom, a C1-C10 alkyl group, a halogen atom or R ₂ -B ₁ -Group (R ₂ Represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl group; ₁ Represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group. ) Represents a C2-C10 alkyl group, a C3-C10 alkenyl group, or a C3-C10 alkynyl group, and k represents 0 or 1; ₁ Is R ₃ -(CHR ₀ ) _m -(B ₂ -B ₃ ) _{m '} -Group {R ₃ Is a hydrogen atom, a halogen atom or R ₂ -B ₁ -Group (R ₂ And B ₁ Represents the same meaning as described above. ) Represents a C1-C10 alkyl group, a C2-C10 alkenyl group, or a C2-C10 alkynyl group optionally substituted by R) ₀ Represents a hydrogen atom, a C1-C10 alkyl group or a C2-C10 haloalkyl group, m represents 0 or 1, B ₂ Is a single bond, an oxy group, a thio group or —N ((O) _n R ₁ ') -Group (R ₁ 'R ₁ Same or different from R ₁ And n represents 0 or 1. ) And B ₃ Represents a carbonyl group, a thiocarbonyl group or a sulfonyl group, m ′ represents 0 or 1, and B ₃ When is a sulfonyl group, m is 0 and R ₃ Does not become a hydrogen atom. }, And k ′ represents 0 or 1. }, R ₄ Represents a C1-C10 alkylene group. However, R ₀ 'R ₀ '' N-R ₄ -Group (R ₀ 'And R ₀ '' Is R ₀ Same or different from R ₀ Represents the same meaning as R ₄ Represents the same meaning as described above. )except for. ], D ₂ -R ₄ -Group [D ₂ Is a cyano group, R ₁ R ₁ 'NC (= N- (O) _n -A ₁ ) -Group (R ₁ , R ₁ ', N, and A ₁ Represents the same meaning as described above. ), A ₁ N = C (-OR ₂ ) -Group (A ₁ And R ₂ Represents the same meaning as described above. Or NH ₂ Represents -CS- group, R ₄ Represents the same meaning as described above. ], D ₃ -R ₄ -Group {D ₃ Is a nitro group or R ₁ OSO ₂ -Group (R ₁ Represents the same meaning as described above. ) And R ₄ Represents the same meaning as described above. } Or R ₁ OSO ₂ -Group (R ₁ Represents the same meaning as described above. ).
(2) Group B:

(A) -group
[In (a), E ₁ And E ₁ 'Represents a methylene group which may be substituted with a C1-C10 alkyl group or a C1-C10 alkoxy group, or a carbonyl group. However, E ₁ And E ₁ 'Is not a carbonyl group at the same time. E ₂ Is an oxy group, thio group, sulfinyl group, sulfonyl group or -NR ₁ '-Group (R ₁ 'Represents the same meaning as described above. C2-C10 alkylene group which may be substituted with ₁ '-Group (R ₁ 'Represents the same meaning as described above. ) Represents a C3-C10 alkenylene group optionally substituted by ₁ Represents the same meaning as described above. ]
It is.
(3) Group C: halogen atom, R ₂ -B ₁ -Group (R ₂ And B ₁ Represents the same meaning as described above. ), D ₄ -R ₄ -Group [D ₄ Is a hydroxyl group or A ₁ —O— group (A ₁ Represents the same meaning as described above. ) And R ₄ Represents the same meaning as described above. ], D ₅ -Group [D ₅ Is O = C (R ₃ ) -Group (R ₃ Represents the same meaning as described above. ), A ₁ -(O) _n -N = C (R ₃ ) -Group (A ₁ , N and R ₃ Represents the same meaning as described above. ), R ₁ -B ₀ -CO-R ₄ -(O) _n -N = C (R ₃ ) -Group {R ₁ , R ₄ , N and R ₃ Represents the same meaning as above, B ₀ Is an oxy group, a thio group or -N ((O) _m R ₁ ') -Group (R ₁ 'And m represent the same meaning as described above. ). }, D ₂ -R ₄ -(O) _n -N = C (R ₃ ) -Group (D ₂ , R ₄ , N and R ₃ Represents the same meaning as described above. Or R ₁ A ₁ N−N = C (R ₃ ) -Group (R ₁ , A ₁ And R ₃ Represents the same meaning as described above. ). ], R ₁ A ₁ N-O-R ₄ -Group (R ₁ , A ₁ And R ₄ Represents the same meaning as described above. ), R ₁ (A ₁ -(O) _n -) N-group (R ₁ , A ₁ And n represent the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. Or D ₃ -Group (D ₃ Represents the same meaning as described above. C2-C10 alkenyl group substituted with
It is.
(4) Group D:

(b) -R ₄ -In the group [(b) G ₁ , G ₂ , G ₄ And G ₅ Represents a methylene group which may be substituted with a methyl group which is bonded to an adjacent atom with a single bond, or a methine group which is bonded to an adjacent atom with a double bond and which may be substituted with a methyl group; ₃ Is a single bond, a double bond, a methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group or —NR ₁ -Group (R ₁ Represents the same meaning as described above. C1-C10 alkylene group optionally substituted with a methyl group, oxy group, thio group, sulfinyl group, sulfonyl group or —NR ₁ -Group (R ₁ Represents the same meaning as described above. ) Represents a C2-C10 alkenylene group which may be substituted with R) ₄ Represents the same meaning as described above. ],

(C) -R ₄ -Group
(In (c), J ₁ , J ₂ And J ₃ Are the same or different and each represents a methine group which may be substituted with a methyl group or a nitrogen atom; ₄ Represents the same meaning as described above. ), Halogen atom, R ₂ -B ₁ -R ₄ -Group (R ₂ , B ₁ And R ₄ Represents the same meaning as described above. ), D ₄ -R ₄ -Group (D ₄ And R ₄ Represents the same meaning as described above. ), D ₅ -Group (D ₅ Represents the same meaning as described above. ), D ₁ -R ₄ -Group (D ₁ And R ₄ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. Or D ₃ -R ₄ -Group (D ₃ And R ₄ Represents the same meaning as described above. C2-C10 alkynyl group substituted with
It is.
(5) Group E: A ₂ -CO-R ₅ -Group
It is. However, A ₂ When R is a hydroxyl group, R ₅ Is not a vinylene group.
[A ₂ Is
(i) A ₃ -B ₄ -Group
{A ₃ Is a hydrogen atom, a C1-C10 alkyl group, a C2-C10 haloalkyl group, a C2-C10 alkenyl group optionally substituted with a halogen atom, or a C3-C10 optionally substituted with a halogen atom. Alkynyl group or R _a -(R ₄ ) _m -Group (R _a Represents a phenyl group, a pyridyl group, a furyl group or a thienyl group, which may be substituted with a halogen atom, a C1-C10 alkyl group, a C1-C10 alkoxy group or a nitro group, and R ₄ And m represent the same meaning as described above. ) Or (b) -R ₄ -Groups ((b) and R ₄ Represents the same meaning as described above. ), (C) -R ₄ -Groups ((c) and R ₄ Represents the same meaning as described above. ), R ₂ -B ₁ -R ₄ -Group (R ₂ , B ₁ And R ₄ Represents the same meaning as described above. ), D ₄ -R ₄ -Group (D ₄ And R ₄ Represents the same meaning as described above. ), D ₅ -Group (D ₅ Represents the same meaning as described above. ), D ₁ -R ₄ -Group (D ₁ And R ₄ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. ), D ₃ -R ₄ -Group (D ₃ And R ₄ Represents the same meaning as described above. Or A ₄ -SO ₂ -R ₄ -Group {A ₄ Is a (b) -group ((b) is as defined above), (c) -group ((c) is as defined above) or R ₁ R ₁ 'N-group (R ₁ And R ₁ 'Represents the same meaning as described above. ) And R ₄ Represents the same meaning as described above. } Represents a C1-C10 alkyl group substituted with
B ₄ Is an oxy group, a thio group or -N ((O) _m R ₁ ) -Group (R ₁ And m represent the same meaning as described above. ). However, B ₄ When is a thio group, A ₃ Is not a hydrogen atom. },
(ii) R ₁ -B ₄ -CO-R ₄ -B ₄ '-Group (R ₁ , B ₄ And R ₄ Represents the same meaning as above, B ₄ 'B ₄ Same or different from B ₄ Represents the same meaning as However, B ₄ When is a thio group, R ₂ Is not a hydrogen atom. Or D ₂ -R ₄ -B ₄ -Group (D ₂ , R ₄ And B ₄ Represents the same meaning as described above. ),
(iii) R ₂ -SO ₂ -NR ₁ -Group (R ₂ Represents the same meaning as described above. However, a hydrogen atom is excluded. R ₁ Represents the same meaning as described above. ),
(iv) (b) -group ((b) represents the same meaning as described above),
(v) (c) -group ((c) represents the same meaning as described above) or
(vi) R ₁ A ₁ N-NR ₁ '-Group (R ₁ , A ₁ And R ₁ 'Represents the same meaning as described above. ) And R ₅ Represents a C2-C10 alkenylene group or a C2-C10 alkynylene group which may be substituted with a halogen atom. ]
(6) Group F: A ₅ -B ₅ -R ₆ -Group [A ₅ D ₄ -Group (D ₄ Represents the same meaning as described above. ), D ₁ -Group (D ₁ Represents the same meaning as described above. ), D ₃ -Group (D ₃ Represents the same meaning as described above. Or A ₄ -SO ₂ -Group (A ₄ Represents the same meaning as described above. Or a C2-C10 alkyl group substituted with R) or R ₂ -B ₁ -Group (R ₂ And B ₁ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. ), D ₅ -Group (D ₅ Represents the same meaning as described above. Or A ₂ -CO- group (A ₂ Represents the same meaning as described above. ) Represents a C1-C10 alkyl group substituted with ₅ Is B ₁ -Group (B ₁ Represents the same meaning as described above. ) Or -NA ₁ -Group (A ₁ Represents the same meaning as described above. ) And R ₆ Represents a single bond or a C1-C10 alkylene group. ]
It is.
(7) Group G: A ₆ -B ₅ -R ₆ -Group
[A ₆ (A) -R ₄ -Groups ((a) and R ₄ Represents the same meaning as described above. ), A C2-C10 alkenyl group, a C2-C10 alkynyl group, a halogen atom, R ₂ -B ₁ -Group (R ₂ And B ₁ Represents the same meaning as described above. ), D ₅ -Group (D ₅ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. Or A ₂ -CO- group (A ₂ Represents the same meaning as described above. ) Substituted C2-C10 alkenyl group or halogen atom, R ₂ -B ₁ -Group (R ₂ And B ₁ Represents the same meaning as described above. ), D ₅ -Group (D ₅ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. Or A ₂ -CO- group (A ₂ Represents the same meaning as described above. ) -Substituted C2-C10 alkynyl group or (b) -group ((b) represents the same meaning as described above), (c) -group ((c) represents the same meaning as described above) D) ₄ -Group (D ₄ Represents the same meaning as described above. ), D ₁ -Group (D ₁ Represents the same meaning as described above. Or D ₃ -Group (D ₃ Represents the same meaning as described above. C3-C10 alkenyl group substituted with) or D ₄ -Group (D ₄ Represents the same meaning as described above. ), D ₁ -Group (D ₁ Represents the same meaning as described above. Or D ₃ -Group (D ₃ Represents the same meaning as described above. ) Represents a C3-C10 alkynyl group substituted with ₅ And R ₆ Represents the same meaning as described above. ]
It is.
(8) Group H:
D ₂ -N (-(O) _n -A ₁ -R ₆ -Group (D ₂ , N, A ₁ And R ₆ Represents the same meaning as described above. ), D ₂ -Group (D ₂ Represents the same meaning as described above. However, the cyano group is excluded. ), R ₁ (R ₁ '(O) _n ) N-CR ₁ '' = N-R ₆ -Group (R ₁ , R ₁ ', N and R ₆ Represents the same meaning as above, R ₁ '' Is R ₁ Same or different from R ₁ Represents the same meaning as ), R ₁ -(O) _n -N = CR ₁ '-NR ₂ -R ₆ -Group (R ₁ , N, R ₁ ', R ₂ And R ₆ Represents the same meaning as described above. ), R ₂ -B ₃ -NR ₁ -CO-NR ₁ '-R ₆ -Group (R ₂ , B ₃ , R ₁ , R ₁ 'And R ₆ Represents the same meaning as described above. ), D ₂ -CO-NR ₁ -R ₆ -Group (D ₂ , R ₁ And R ₆ Represents the same meaning as described above. ) Or A ₂ -COCO-NR ₁ -R ₆ -Group (A ₂ , R ₁ And R ₆ Represents the same meaning as described above. )
It is.
(9) Group I:
A ₇ -B ₆ -N ((O) _n R ₁ -R ₆ -Group [A ₇ Is a C2-C10 alkenyl group, C2-C10 alkynyl group, C3-C10 haloalkynyl group, R which may be substituted with a halogen atom, ₂ -B ₁ -R ₄ -Group (R ₂ , B ₁ And R ₄ Represents the same meaning as described above. ), D ₄ -R ₄ -Group (D ₄ And R ₄ Represents the same meaning as described above. ), D ₅ -R ₄ -Group (D ₅ And R ₄ Represents the same meaning as described above. ), D ₁ -R ₄ -Group (D ₁ And R ₄ Represents the same meaning as described above. ), (B) -R ₄ -Groups ((b) and R ₄ Represents the same meaning as described above. ), (C) -R ₄ -Groups ((c) and R ₄ Represents the same meaning as described above. ), D ₂ -R ₄ -Group (D ₂ And R ₄ Represents the same meaning as described above. ), D ₃ -R ₄ -Group (D ₃ And R ₄ Represents the same meaning as described above. ), A ₄ -SO ₂ -R ₄ -Group (A ₄ And R ₄ Represents the same meaning as described above. ) Or A ₂ -CO-R ₄ -Group (A ₂ And R ₄ Represents the same meaning as described above. ) And B ₆ Represents a carbonyl group or a thiocarbonyl group, and n, R ₁ And R ₆ Represents the same meaning as described above. ], A ₈ -CS-N ((O) _n R ₁ -R ₆ -Group [A ₈ Represents a hydrogen atom or a C1-C10 alkyl group which may be substituted with a halogen atom, and n, R ₁ And R ₆ Represents the same meaning as described above. ],
A ₇ '-B ₂ '-B ₃ -N ((O) _n R ₁ -R ₆ -Group [A ₇ 'Is a C3-C10 alkenyl group which may be substituted with a halogen atom, a C3-C10 alkynyl group which may be substituted with a halogen atom, R ₂ -B ₁ -R ₄ '-Group (R ₂ And B ₁ Represents the same meaning as above, R ₄ 'Represents a C2-C10 alkylene group. ), D ₄ -R ₄ '-Group (D ₄ And R ₄ 'Represents the same meaning as described above. ), D ₁ -R ₄ '-Group (D ₁ And R ₄ 'Represents the same meaning as described above. ), (B) -R ₄ '-Group ((b) and R ₄ 'Represents the same meaning as described above. ), (C) -R ₄ '-Group ((c) and R ₄ 'Represents the same meaning as described above. ), D ₂ -R ₄ -Group (D ₂ And R ₄ Represents the same meaning as described above. ), D ₃ -R ₄ '-Group (D ₃ And R ₄ 'Represents the same meaning as described above. ) Or A ₂ -CO-R ₄ -Group (A ₂ And R ₄ Represents the same meaning as described above. ) And B ₂ 'Represents an oxy group, a thio group, or -N ((O) _{n '} R ₁ ') -Group (n' is the same as or different from n and represents the same meaning as n, R ₁ 'Represents the same meaning as described above. ) And B ₃ , N, R ₁ And R ₆ Represents the same meaning as described above. ], A ₈ '-B ₂ '-CS-N ((O) _n R ₁ -R ₆ -Group [A ₈ 'Represents a C1-C10 alkyl group or a C2-C10 haloalkyl group, and B ₂ 'Represents the same meaning as described above, and n, R ₁ And R ₆ Represents the same meaning as described above. ], A ₈ '-SB ₃ '-N ((O) _n R ₁ -R ₆ -Group [A ₈ ', N, R ₁ And R ₆ Represents the same meaning as above, B ₃ 'Represents a carbonyl group or a sulfonyl group. ] Or A ₇ '' -SO ₂ -N ((O) _n R ₁ -R ₆ -Group [A ₇ '' Is a C2-C10 alkenyl group, a C3-C10 alkenyl group substituted with a halogen atom, a C3-C10 alkynyl group optionally substituted with a halogen atom, R ₂ -B ₁ -R ₄ '-Group (R ₂ , B ₁ And R ₄ 'Represents the same meaning as described above. ), D ₄ -R ₄ '-Group (D ₄ And R ₄ 'Represents the same meaning as described above. ), D ₅ -R ₄ -Group (D ₅ And R ₄ Represents the same meaning as described above. ), D ₁ -R ₄ '-Group (D ₁ And R ₄ 'Represents the same meaning as described above. ), (B) -R ₄ '-Group ((b) and R ₄ 'Represents the same meaning as described above. ), (C) -R ₄ '-Group ((c) and R ₄ 'Represents the same meaning as described above. ), D ₂ -R ₄ -Group (D ₂ And R ₄ Represents the same meaning as described above. ), NO ₂ -R ₄ -Group (R ₄ Represents the same meaning as described above. ) Or A ₂ -CO-R ₄ -Group (A ₂ And R ₄ Represents the same meaning as described above. ), N, R ₁ And R ₆ Represents the same meaning as described above. ]
It is.
(10) Group J: A ₇ -CO- group (A ₇ Represents the same meaning as described above. ) Or A ₉ -CS- group (A ₉ A ₇ Or A ₈ Represents. ) Or A ₉ '(O) _m N = C (A ₉ ) -Group (A ₉ 'A ₇ 'Or A ₈ 'And m and A ₉ Represents the same meaning as described above. ) Or D ₂ —CO— group (D ₂ Represents the same meaning as described above. ) Or A ₂ -COCO- group (A ₂ Represents the same meaning as described above. ) Or A ₉ -CO-B ₁ '-R ₆ -Group (A ₉ And R ₆ Represents the same meaning as above, B ₁ 'Represents an oxy group or a thio group. However, B ₁ When 'is an oxy group, A ₉ A ₈ is not. ) Or A ₉ -CS-B ₁ '-R ₆ -Group (A ₉ , B ₁ 'And R ₆ Represents the same meaning as described above. ) Or A ₇ '' -SO ₂ -B ₁ '-R ₆ -Group (A ₇ '' 、 B ₁ 'And R ₆ Represents the same meaning as described above. ) Or A ₈ -SO ₂ -B ₁ '-R ₆ -Group (A ₈ , B ₁ 'And R ₆ Represents the same meaning as described above. However, A ₈ Does not become a hydrogen atom. ) Or A ₉ '-B ₂ '-B ₃ -B ₁ '-R ₆ -Group (A ₉ ', B ₂ ', B ₃ , B ₁ 'And R ₆ Represents the same meaning as described above. ) Or (b) -group ((b) represents the same meaning as described above) or (c) -group ((c) represents the same meaning as described above) substituted C2 -C10 alkenyl group
It is.
(11) Group K: A ₁₀ -N ((O) _n R ₁ ) -CO-R ₆ -Group [A ₁₀ Is a hydrogen atom (where n is not 0), A ₇ '' -SO ₂ -Group (A ₇ '' Represents the same meaning as described above. ), A ₈ -SO ₂ -Group (A ₈ Represents the same meaning as described above. However, A ₈ Does not become a hydrogen atom. ), A ₉ 'O-group (A ₉ 'Represents the same meaning as described above. However, n is not 1. ), A ₉ '-Group (A ₉ 'Represents the same meaning as described above. However, when n is 0, A ₈ 'except for. ), R ₂ OCH ₂ -Group (R ₂ Represents the same meaning as described above. ), A ₂ -CO-R ₄ -Group (A ₂ And R ₄ Represents the same meaning as described above. ) Or A ₂ -CO-CH (CH ₂ CO-A ₂ ) -Group (A ₂ Represents the same meaning as described above. ), N, R ₁ And R ₆ Represents the same meaning as described above. ]
It is.
(12) L group: A ₁₀ '-N ((O) _n R ₁ -SO ₂ -R ₆ -Group [A ₁₀ 'Is a hydrogen atom (where n is not 0), A ₉ 'O-group (A ₉ 'Represents the same meaning as described above. However, n is not 1. ), A ₉ '-Group (A ₉ 'Represents the same meaning as described above. However, when n is 0, A ₈ 'except for. ), R ₂ —CO— group (R ₂ Represents the same meaning as described above. ), A ₂ -CO-R ₄ -Group (A ₂ And R ₄ Represents the same meaning as described above. ) Or A ₂ -CO-CH (CH ₂ CO-A ₂ ) -Group (A ₂ Represents the same meaning as described above. ), N, R ₁ And R ₆ Represents the same meaning as described above. ], A ₉ '' R ₁ N-SO ₂ -N ((O) _n R ₁ ') -R ₆ -Group [A ₉ '' Is a hydrogen atom or A ₉ '-Group (A ₉ 'Represents the same meaning as described above. ) And R ₁ , N, R ₁ 'And R ₆ Represents the same meaning as described above. Or (b) -SO ₂ -N ((O) _n R ₁ ') -R ₆ -Group [(b), n, R ₁ 'And R ₆ Represents the same meaning as described above. ]
It is.
(13) M group: R ₁ (R ₂ S) C = N-R ₆ -Group (R ₁ , R ₂ And R ₆ Represents the same meaning as described above. ), R ₂ B (R ₂ 'B') C = N-R ₆ -Group (R ₂ And R ₆ Represents the same meaning as above, R ₂ 'R ₂ Same or different from R ₂ And B and B ′ are the same or different and represent an oxy group or a thio group. ), R ₁ R ₁ 'N- (R ₂ S) C = N-R ₆ -Group (R ₁ , R ₁ ', R ₂ And R ₆ Represents the same meaning as described above. ), R ₁ N = C (SR ₂ -NR ₂ '-R ₆ -Group (R ₁ , R ₂ , R ₂ 'And R ₆ Represents the same meaning as described above. Or R ₁ (R ₁ 'O) N-R ₆ -Group (R ₁ , R ₁ 'And R ₆ Represents the same meaning as described above. )
It is.
(14) Group N: A ₁₁ -P (= O) (OR ₁ ') -R ₄ -Group [A ₁₁ Is R ₁ -Group (R ₁ Represents the same meaning as described above. ), R ₁ O-R ₆ -Group (R ₁ And R ₆ Represents the same meaning as described above. Or R ₁ OCO-CHR ₀ -Group (R ₁ And R ₀ Represents the same meaning as described above. ) And R ₁ 'And R ₄ Represents the same meaning as described above. ]
It is.
III. (Y _A ) _q Y _A Represents a group of the following X group or Y group, q represents 0, 1, 2 or 3, and the sum of p (p represents the same meaning as described above) and q is 3 or less. Yes, when q is 2 or more, Y _A Are the same or different, and when q is 2 or more, two adjacent Ys that are the same or different _A May form a group Z and may be condensed with the A ring.
(1) Group X: M _a -Group [M _a Is R _b -Group (R _b Represents a C1-C10 alkyl group which may be substituted with a halogen atom. ), Halogen atom, nitro group, cyano group, R _c -B _a -R _d -Group (R _c Represents a C1-C10 alkyl group which may be substituted with a halogen atom; _a Represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group, and R _d Represents a single bond or a C1-C10 alkylene group. ), HO-R _d -Group (R _d Represents the same meaning as described above. ), R _e -CO-R _d -Group (R _e Represents a hydrogen atom or a C1-C10 alkyl group which may be substituted with a halogen atom; _d Represents the same meaning as described above. ), R _e -CO-O-R _d -Group (R _e And R _d Represents the same meaning as described above. ), R _e O-CO-R _d -Group (R _e And R _d Represents the same meaning as described above. ), HO—CO—CH═CH— group, R _e R _e 'N-R _d -Group (R _e And R _e 'Is the same or different, R _e Represents the same meaning as above, R _e 'R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _e -CO-NR _e '-R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), R _b O-CO-N (R _e -R _d -Group (R _b , R _e And R _d Represents the same meaning as described above. ), R _e R _e 'N-CO-R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), R _e R _e 'N-CO-NR _e '' -R _d -Group (R _e , R _e 'And R _e '' Is the same or different, R _e And R _e 'Represents the same meaning as described above, and R _e '' Is R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _e R _e 'NC (= NR _e '') -NR _e '''-R _d -Group (R _e , R _e ', R _e '' And R _e '''Is the same or different, R _e , R _e 'And R _e '' Represents the same meaning as above, R _e '''Is R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _b -SO ₂ -NR _e -R _d -Group (R _b , R _e And R _d Represents the same meaning as described above. ), R _e R _e 'N-SO ₂ -R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), A C2-C10 alkenyl group or a C2-C10 alkynyl group. ].
(2) Y group: M _b -R _d -Group [M _b Is M _c -Group {M _c Is M _d -R _d '-Group {M _d Is M _a -Group (M _a Represents the same meaning as described above. A phenyl group optionally substituted with M) _a -Group (M _a Represents the same meaning as described above. Pyridyl group optionally substituted with M) _a -Group (M _a Represents the same meaning as described above. ) May be substituted with a naphthyl group, (b) -group ((b) represents the same meaning as described above), (c) -group ((c) represents the same meaning as described above. ),

(D) -group (l is 2, 3 or 4; B _b Represents an oxy group or a thio group. Or

(E) -group (l and B _b Represents the same meaning as described above. ) And R _d 'R _d Same or different from R _d Represents the same meaning as }. }, M _c -B _a -Group (M _c And B _a Represents the same meaning as described above. ), M _c —CO— group (M _c Represents the same meaning as described above. ), M _c -CO-O- group (M _c Represents the same meaning as described above. ), M _c O-CO- group (M _c Represents the same meaning as described above. ), M _c R _e N-group (M _c And R _e Represents the same meaning as described above. ), M _c -CO-NR _e -Group (M _c And R _e Represents the same meaning as described above. ), M _c O-CO-NR _e -Group (M _c And R _e Represents the same meaning as described above. ), M _c R _e N-CO- group (M _c And R _e Represents the same meaning as described above. ), M _c R _e N-CO-NR _e '-Group (M _c , R _e And R _e 'Represents the same meaning as described above. ), M _c R _e N-C (= NR _e ') -NR _e '' -Group (M _c , R _e , R _e 'And R _e '' Represents the same meaning as described above. ), M _c -SO ₂ -NR _e -Group (M _c And R _e Represents the same meaning as described above. ) Or M _c R _e N-SO ₂ -Group (M _c And R _e Represents the same meaning as described above. ) And R _d Represents the same meaning as described above. ].
(3) Z group: -Y _a '' = C (Y _a -Y _a '-Group (Y _a Represents a hydrogen atom or a C1-C10 alkyl group which may be substituted with a halogen atom or a C1-C10 alkoxy group; _a 'Represents an imino group that may be substituted with an oxy group, a thio group, or a C1-C10 alkyl group; _a '' Represents a -N = group or a methine group. ), C3-C10 alkylene group or -Y _b = Y _b '-Y _b '' = Y _b '''-Group [Y _b , Y _b ', Y _b '' And Y _b '''Is the same or different, and Ma-group (M _a Represents the same meaning as described above. ) Represents a methine group which may be substituted or -N = group. ].
IV. B is
Formula (IV-1)

[Where:
(1) Q _A Is a hydroxyl group, (b) -group ((b) represents the same meaning as described above), A ₉ -B ₆ -B _c -Group [A ₉ And B ₆ Represents the same meaning as above, B _c Is an oxy group or -N ((O) _m R ₁ ) -Group (m and R ₁ Represents the same meaning as described above. ). However, A ₉ When is a hydrogen atom, B _c Is not a sulfonyl group. ], A ₇ '' -SO ₂ -B _c -Group (A ₇ '' And B _c Represents the same meaning as described above. ), A ₈ -SO ₂ -B _c -Group (A ₈ And B _c Represents the same meaning as described above. However, A ₈ Does not become a hydrogen atom. ), R ₁ R ₁ 'N-SO ₂ -B _c -Group (R ₁ , R ₁ 'And B _c Represents the same meaning as described above. ), (B) -SO ₂ -B _c -Groups ((b) and B _c Represents the same meaning as described above. ), A ₉ '-B _c -Group (A ₉ 'And B _c Represents the same meaning as described above. ), D ₅ -R ₄ -B _c -Group (D ₅ , R ₄ And B _c Represents the same meaning as described above. ), M _c -B ₃ -B _c -Group (M _c , B ₃ And B _c Represents the same meaning as described above. ) Or M _c -B _c -Group (M _c And B _c Represents the same meaning as described above. ).
(2) W _A Is an oxygen atom or -NT _A -Group [T _A Is a hydrogen atom, A ₉ '-Group (A ₉ 'Represents the same meaning as described above. ), D ₅ -R ₄ -Group (D ₅ And R ₄ Represents the same meaning as described above. ) Or M _c -Group (M _c Represents the same meaning as described above. ). ]. T _A Is a hydrogen atom, A ₉ '-Group (A ₉ 'Represents the same meaning as described above. ), D ₅ -R ₄ -Group (D ₅ And R ₄ Represents the same meaning as described above. ) Or M _c -Group (M _c Represents the same meaning as described above. ).
(3) K _A Represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group; _A Is a hydrogen atom, a C1-C10 alkyl group or M _b -Group (M _b Represents the same meaning as described above. ) And K _A And L _A Is a C3-C10 alkylene group or -C (M _a ') = C (M _a '') -C (M _a ''') = C (M _a '''') -Group (M _a ', M _a '', M _a '''And M _a '''' Is the same or different, M _a Same as or different from, hydrogen atom or M _a Represents. ). ]
A group represented by
Formula (IV-2)

[Where T _A Represents the same meaning as described above, and L _B Represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (IV-3)

[Where T _A Represents the same meaning as described above, and L _C Represents a C1-C10 alkyl group. ]
A group represented by
Formula (IV-4)

[Where T _A Represents the same meaning as described above. ]
A group represented by
Formula (IV-5)

[Where T _A Represents the same meaning as described above, and K _B Represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (IV-6)

[Where W _A Represents the same meaning as described above, and K _C And L _D Is a C3-C10 alkylene group or a C4-C10 alkenylene group which may be substituted with one or a plurality of Ma-groups (Ma represents the same meaning as described above). ]
A group represented by
Formula (IV-7)

[Where Q _A And W _A Represents the same meaning as described above, and K _D And L _E Is -V _A = V _A '-V _A '' = V _A '''-Group {V _A , V _A ', V _A '' And V _A '''Is the same or different, M _a -Group (M _a Represents the same meaning as described above. ) Represents a methine group which may be substituted, or -N = group, and V _A , V _A ', V _A '' And V _A At least one of '''represents a -N = group. }. ]
A group represented by
Formula (IV-8)

[Where T _A Represents the same meaning as above, Q _B Is a hydroxyl group, A ₉ -B ₆ —O— group [A ₉ And B ₆ Represents the same meaning as described above. ], A ₇ '' -SO ₂ —O— group (A ₇ '' Represents the same meaning as described above. ), A ₈ -SO ₂ —O— group (A ₈ Represents the same meaning as described above. However, A ₈ Does not become a hydrogen atom. ), R ₁ R ₁ 'N-SO ₂ —O— group (R ₁ And R ₁ 'Represents the same meaning as described above. ), (B) -SO ₂ -O- group ((b) represents the same meaning as described above), A ₉ '-O- group (A ₉ 'Represents the same meaning as described above. ), D ₅ -R ₄ —O— group (D ₅ And R ₄ Represents the same meaning as described above. ), M _c -B ₃ —O— group (M _c And B ₃ Represents the same meaning as described above. ) Or M _c —O— group (M _c Represents the same meaning as described above. ). ]
Or a group represented by
Formula (IV-9)

[Where U and W _A Represents the same meaning as described above. ]
Represents a group represented by
However, when A is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:
5. Formula (V)

[Where:
I. a represents a thiophene ring, furan ring, pyrrole ring, pyrazole ring, 1,2,3-triazole ring, tetrazole ring, isoxazole ring, thiazole ring, pyridazine ring or pyrimidine ring; _a Is a C1-C10 alkyl group substituted with a cyano group, a C1-C10 alkyl group substituted with a tetrahydropyran-4-ylidene group, or a C2-C10 alkenyl group substituted with a halogen atom or a cyano group, Or a C2-C10 alkenyl group substituted with a C1-C10 alkoxycarbonyl group, a C3-C10 alkynyl group substituted with a hydroxy group, or a ₀ -R ₁ -B-r ₁ '-Group {a ₀ Is a methyl group substituted with a C1-C10 alkylthio group, a methyl group substituted with a C1-C10 alkylsulfinyl group, a methyl group substituted with a C1-C10 alkylsulfonyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group Group, r ₂ O—CO— group (r ₂ Represents a C1-C10 alkyl group or a C2-C10 alkyl group substituted with a hydroxyl group. ), A carboxy group, an rr′N—CO— group (r and r ′ are the same or different and each represents a hydrogen atom or a C1-C10 alkyl group), a ₁ -NH-CO- group (a ₁ Represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group. ), A ₁ '-CO- group (a ₁ 'Represents a morpholino group. ), Rr'N-CH ₂ -Group (r and r 'are as defined above), r ₀ -(O) _l -CONH-CH ₂ -Group (r ₀ Represents a C1-C10 alkyl group, and l represents 0 or 1. ), R-OCH ₂ -Group (r represents the same meaning as described above), r ₀ —CO— group (r ₀ Represents the same meaning as described above. ), A cyano group or a sulfomethyl group, r ₁ Represents a C1-C10 alkylene group, r ₁ 'Represents a single bond or a C1-C10 alkylene group, and b represents an imino group which may be substituted with an oxy group, a thio group, a sulfinyl group, a sulfonyl group or a methyl group. } Or a ₂ -Y-CO-NH- group (a ₂ Represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group, and y represents an oxy group or an imino group. ) Or rO—COCO—NH— group (where r represents the same meaning as described above), or a ₃ -Z-NH- group (a ₃ Represents a C2-C10 alkenyl group, or a C1-C10 alkoxy group substituted with a C1-C10 alkoxy group, a C1-C10 alkoxycarbonyl group, a carboxy group or a cyano group, and z represents a carbonyl group or a sulfonyl group. . ) Or a ₄ -Nr'CO- group {a ₄ Is a C1-C10 alkoxy group, a C3-C10 alkenyloxy group, or r ₀ -SO ₂ -Group (r ₀ Represents the same meaning as described above. ), Or a C2-C10 alkyl group substituted with a hydroxyl group or a C1-C10 alkoxy group, or r ₀ r ₀ 'N-group (r ₀ Represents the same meaning as described above, and r ₀ 'R ₀ Same as or different from r ₀ Represents the same meaning as ) -Substituted C2-C10 alkyl group, or rO-CO- group (where r represents the same meaning as described above), a C1-C10 alkyl group substituted with a cyano group or an aminocarbonyl group, or rO-CO- (rO-COCH ₂ ) CH— group (wherein r represents the same meaning as described above), and r ′ represents the same meaning as described above. } Or a ₅ -NHSO ₂ -Group (a ₅ Represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group. ) Or r ₀ ON = CH-group (r ₀ Represents the same meaning as described above. ) Or r ₀ NHCSNH-group (r ₀ Represents the same meaning as described above. ) Or r ₀ NHC (-Sr ₀ ') = N-group (r ₀ And r ₀ 'Represents the same meaning as described above. ) Or (rO) ₂ P (= O) CH ₂ -Represents a group (r represents the same meaning as described above), p represents 0, 1, 2, or 3, and when p is 2 or more, X _a Are the same or different,
Y _a Is a halogen atom, a C1-C10 alkyl group that may be substituted with a halogen atom, a C1-C10 alkyl group that may be substituted with a C1-C10 alkoxy group, or a C2-C10 alkenyl group, or A C2-C10 alkynyl group, a 2-oxo-oxazolidin-3-yl group, a [1,3] dioxolan-2-yl group, or a C1-C10 alkoxy group substituted with a morpholino group, or a ₀ '-B'-group (a ₀ 'Represents a C1-C10 alkyl group which may be substituted with a halogen atom, and b' represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group. ), A nitro group, a cyano group, or an rO—CO— group (where r represents the same meaning as described above), or r ₀ r ₀ 'N-group (r ₀ And r ₀ 'Represents the same meaning as described above. ) Or r ₀ CO—NH— group (r ₀ Represents the same meaning as described above. ) Or r ₀ r ₀ 'NCONH-group (r ₀ And r ₀ 'Represents the same meaning as described above. ) Or rr′NCO— group (r and r ′ represent the same meaning as described above) or a hydroxyl group, q represents 0, 1, 2 or 3, and q is 2 or more. When Y _a Are the same or different, and when q is 2 or more, adjacent Y _a May be condensed with a ring to form a 4,5,6,7-tetrahydrobenzo [b] thiophene ring.
II. b is
Formula (V-1)

[Where Q _a R _a —O— group {r _a Is a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, or r ₀ r ₀ 'N-CH ₂ -Group (r ₀ And r ₀ 'Represents the same meaning as described above. ), ROCH ₂ -Group (r represents the same meaning as described above), r ₀ —CO— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group, a C1-C10 alkyl group substituted with a cyano group, or r ₃ -R ₁ -Group (r ₃ Represents a phenyl group or a pyridyl group, and r ₁ Represents the same meaning as described above. ). }, Or a piperidino group, or a morpholino group, or r ₄ r ₄ 'N-group (r ₄ And r ₄ 'Is the same or different and is a C2-C10 alkyl substituted with a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C1-C10 alkoxy group. Represents a group. However, it does not become a hydrogen atom at the same time. ) And W _a Is an oxygen atom or -NT _a -Group [T _a R _b -Group (r _b R _a Same as or different from r _a Represents the same meaning as Or r ₃ '-Group (r ₃ 'R ₃ Same as or different from r ₃ Represents the same meaning as ). ] And K _a Represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group; _a Represents a hydrogen atom or a C1-C10 alkyl group, and K _a And L _a And may form a C3-C10 alkylene group or a 1,3-butadienylene group. ]
A group represented by
Formula (V-2)

[Where T _a Represents the same meaning as described above, and L _b Represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (V-3)

[Where T _a Represents the same meaning as described above, and L _c Represents a C1-C10 alkyl group. ]
A group represented by
Formula (V-4)

[Where T _a Represents the same meaning as described above. ]
A group represented by
Formula (V-5)

[Where T _a Represents the same meaning as described above, and K _b Represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (V-6)

[Where W _a Represents the same meaning as described above, and K _c And L _d And C3-C10 alkylene group or C4-C10 alkenylene group. ]
A group represented by
Formula (V-7)

[Where Q _a And W _a Represents the same meaning as described above, and K _d And L _e Is -V _a = V _a '-V _a '' = V _a '''-Group (V _a , V _a ', V _a '' And V _a '''Is the same or different and represents a methine group or -N = group; _a , V _a ', V _a '' And V _a At least one of '''represents a -N = group. ). ]
A group represented by
Formula (V-8)

[Where T _a Represents the same meaning as above, Q _b R _a —O— group (r _a Represents the same meaning as described above. ). ]
Or a group represented by
Formula (V-9)

[Where U and W _a Represents the same meaning as described above. ]
Represents a group represented by
However, when a is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:
6). Formula (VI)

[Wherein, a1 represents a thiophene ring, a furan ring, a pyrrole ring or a thiazole ring; _a1 Is a ₀ '-R ₁ -B ₀ -R ₁ '-Group {a ₀ 'Represents an rO-CO- group (r represents a hydrogen atom or a C1-C10 alkyl group), r ₀ r ₀ 'N-CH ₂ -Group (r ₀ And r ₀ 'Is the same or different and represents a C1-C10 alkyl group. ) Or a hydroxymethyl group, r ₁ Represents a C1-C10 alkylene group, r ₁ 'Represents a single bond or a C1-C10 alkylene group, b ₀ Represents an imino group substituted with an oxy group, a thio group, a sulfinyl group, a sulfonyl group or one methyl group. } Or a ₂ -O-CO-NH- group (a ₂ Represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group. ) Or a ₃ '-CO-NH- group (a ₃ 'Represents a C1-C10 alkyl group substituted with a C1-C10 alkoxy group. ) Or a ₄ '-NrCO- group
(A ₄ Is a C2-C10 alkyl group substituted with a hydroxyl group or a C1-C10 alkoxy group, or
Represents a C1-C10 alkyl group substituted with an aminocarbonyl group, and r represents the same meaning as described above. ) And b1 is
Formula (VI-1)

(Where r _b1 Represents a hydrogen atom or a C1-C10 alkyl group, and K _a1 Represents a hydrogen atom and L _a1 Represents a C1-C10 alkyl group and K _a1 And L _a1 May form a 1,3-butadienylene group. )
A group represented by
Formula (VI-7)

(Where r _b1 Represents the same meaning as described above. )
Or a group represented by
Formula (VI-8)

(Where r _b1 Represents the same meaning as described above. )
Represents a group represented by
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:
7). Formula (VII)

[Wherein, a1 represents a thiophene ring, a furan ring, a pyrrole ring or a thiazole ring; _a1 Is a ₀ '-R ₁ -B ₀ -R ₁ '-Group {a ₀ 'R ₀ O—CO— group (r ₀ Represents a C1-C10 alkyl group. ), R ₀ r ₀ 'N-CH ₂ -Group (r ₀ And r ₀ 'Is the same or different, r ₀ 'R ₀ Represents the same meaning as ) Or a hydroxymethyl group, r ₁ Represents a C1-C10 alkylene group, r ₁ 'Represents a single bond or a C1-C10 alkylene group, b ₀ Represents an imino group substituted with an oxy group, a thio group, a sulfinyl group, a sulfonyl group or one methyl group. } Or a ₂ -O-CO-NH- group (a ₂ Represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group. ) Or a ₃ '-CO-NH- group (a ₃ 'Represents a C1-C10 alkyl group substituted with a C1-C10 alkoxy group. ) Or a ₄ '-NrCO- group
(A ₄ Is a C2-C10 alkyl group substituted with a hydroxyl group or a C1-C10 alkoxy group, or
Represents a C1-C10 alkyl group substituted with an aminocarbonyl group, and r represents a hydrogen atom or a C1-C10 alkyl group. ). However, when a1 is a thiophene ring, ₀ Is a dimethylaminomethyl group or a hydroxymethyl group, and at the same time, r ₁ Is a methylene group and at the same time r ₁ 'Is a single bond and at the same time b ₀ Is not an oxy group, a thio group or an imino group substituted with one methyl group, and when a1 is a thiophene ring, ₀ 'Is a methoxycarbonyl group and at the same time r ₁ Is a methylene group and at the same time r ₁ 'Is a single bond and at the same time b ₀ Is not a thio group. ]
An aldehyde derivative represented by
8). Formula (VIII)

[Wherein, a1 represents a thiophene ring, a furan ring, a pyrrole ring or a thiazole ring; _a1 Is a ₀ '-R ₁ -B ₀ -R ₁ '-Group {a ₀ 'R ₀ O—CO— group (r ₀ Represents a C1-C10 alkyl group. ), R ₀ r ₀ 'N-CH ₂ -Group (r ₀ And r ₀ 'Is the same or different, r ₀ 'R ₀ Represents the same meaning as ) Or a hydroxymethyl group, r ₁ Represents a C1-C10 alkylene group, r ₁ 'Represents a single bond or a C1-C10 alkylene group, b ₀ Represents an imino group substituted with an oxy group, a thio group, a sulfinyl group, a sulfonyl group or one methyl group. } Or a ₂ -O-CO-NH- group (a ₂ Represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group. ) Or a ₃ '-CO-NH- group (a ₃ 'Represents a C1-C10 alkyl group substituted with a C1-C10 alkoxy group. ) Or a ₄ '-NrCO- group
(A ₄ Is a C2-C10 alkyl group substituted with a hydroxyl group or a C1-C10 alkoxy group, or
Represents a C1-C10 alkyl group substituted with an aminocarbonyl group, and r represents a hydrogen atom or a C1-C10 alkyl group. ). However, when a1 is a thiophene ring, ₀ Is a dimethylaminomethyl group or a hydroxymethyl group, and at the same time, r ₁ Is a methylene group and at the same time r ₁ 'Is a single bond and at the same time b ₀ Is not an oxy group, a thio group or an imino group substituted with one methyl group, and when a1 is a thiophene ring, ₀ 'Is a methoxycarbonyl group and at the same time r ₁ Is a methylene group and at the same time r ₁ 'Is a single bond and at the same time b ₀ Is not a thio group. ]
An aldehyde derivative represented by formula (VIII ′)

[Wherein b1 is
Formula (VIII-1)

(Where r _b1 Represents a hydrogen atom or a C1-C10 alkyl group, and K _a1 Represents a hydrogen atom and L _a1 Represents a C1-C10 alkyl group and K _a1 And L _a1 May form a 1,3-butadienylene group. )
A group represented by
Formula (VIII-7)

(Where r _b1 Represents the same meaning as described above. )
Or a group represented by
Formula (VIII-8)

(Where r _b1 Represents the same meaning as described above. )
Represents a group represented by ]
Characterized by reacting with a compound of formula (VIII ″)

[Wherein a1, X _a1 And b1 represent the same meaning as described above. ]
The manufacturing method of the cinnamoyl compound shown by these.
9. Formula (I ')

[Where:
I. α represents an aromatic 5-membered ring or an aromatic 6-membered ring having two or more nitrogen atoms, and (Y _α ) _q Y _α Is the following X ₀ Group or Y ₀ Represents a group of groups, q represents 0, 1, 2 or 3, and when q is 2 or more, Y _α Are the same or different, and when q is 2 or more, two adjacent Y same or different Y _α Is Z ₀ It may be condensed with an α ring as a group, and (X _α ) _p X _α Is the following X ₀ Group, Y ₀ Group and Z ₀ Represents a substituent not belonging to the group, p represents 0, 1, 2 or 3, and when p is 2 or more, X _α Are the same or different, and the sum of p and q is 3 or less.
(1) X ₀ Group: M _a -Group [M _a Is R _b -Group (R _b Represents a C1-C10 alkyl group which may be substituted with a halogen atom. ), Halogen atom, nitro group, cyano group, hydroxyl group, R _c -B _a -R _d -Group (R _c Represents a C1-C10 alkyl group which may be substituted with a halogen atom; _a Represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group, and R _d Represents a single bond or a C1-C10 alkylene group. ), HOR _d -Group (R _d Represents the same meaning as described above. ), R _e -CO-R _d -Group (R _e Represents a hydrogen atom or a C1-C10 alkyl group which may be substituted with a halogen atom; _d Represents the same meaning as described above. ), R _e -CO-O-R _d -Group (R _e And R _d Represents the same meaning as described above. ), R _e O-CO-R _d -Group (R _e And R _d Represents the same meaning as described above. ), HO—CO—CH═CH— group, R _e R _e 'N-R _d -Group (R _e And R _e 'Is the same or different, R _e Represents the same meaning as above, R _e 'R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _e -CO-NR _e '-R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), R _b O-CO-N (R _e -R _d -Group (R _b , R _e And R _d Represents the same meaning as described above. ), R _e R _e 'N-CO-R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), R _e R _e 'N-CO-NR _e '' -R _d -Group (R _e , R _e 'And R _e '' Is the same or different, R _e And R _e 'Represents the same meaning as described above, and R _e '' Is R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _e R _e 'NC (= NR _e '') -NR _e '''-R _d -Group (R _e , R _e ', R _e '' And R _e '''Is the same or different, R _e , R _e 'And R _e '' Represents the same meaning as above, R _e '''Is R _e Represents the same meaning as R _d Represents the same meaning as described above. ), R _b -SO ₂ -NR _e -R _d -Group (R _b , R _e And R _d Represents the same meaning as described above. ), R _e R _e 'N-SO ₂ -R _d -Group (R _e , R _e 'And R _d Represents the same meaning as described above. ), A C2-C10 alkenyl group or a C2-C10 alkynyl group. ].
(2) Y ₀ Group: M _b0 -R _d -Group [M _b0 Is M _c0 -Group {M _c0 Is M _d0 -R _d '-Group {M _d0 Is M _a -Group (M _a Represents the same meaning as described above. 6-10 membered aryl group optionally substituted with M), or M _a -Group (M _a Represents the same meaning as described above. 5-10 membered heteroaryl group optionally substituted with M), or M _a -Group (M _a Represents the same meaning as described above. 3-10-membered hydrocarbon ring or heterocyclic group which may contain an unsaturated bond which may be substituted, or

(E ₀ ) -Group {e ₀ Is a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, -NR ₁ -Group (R ₁ Represents the same meaning as described above. ), A 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group. }, R _d 'R _d Same or different from R _d Represents the same meaning as }. }, M _c0 -B _a -Group (M _c0 And B _a Represents the same meaning as described above. ), M _c0 —CO— group (M _c0 Represents the same meaning as described above. ), M _c0 -CO-O- group (M _c0 Represents the same meaning as described above. ), M _c0 O-CO- group (M _c0 Represents the same meaning as described above. ), M _c0 R _e N-group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 -CO-NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 O-CO-NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 R _e N-CO- group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 R _e N-CO-NR _e '-Group (M _c0 , R _e And R _e 'Represents the same meaning as described above. ), M _c0 R _e N-C (= NR _e ') -NR _e '' -Group (M _c0 , R _e , R _e 'And R _e '' Represents the same meaning as described above. ), M _c0 -SO ₂ -NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ) Or M _c0 R _e N-SO ₂ -Group (M _c0 And R _e Represents the same meaning as described above. ) And R _d Represents the same meaning as described above. ].
(3) Z ₀ Group: may have a halogen atom, C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group, A 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring and a group condensed with the α ring.
II. β 'is
Formula (I'-1)

[Where:
(1) Q _α Represents an optionally substituted hydroxyl group or an optionally substituted amino group.
(2) W _α Is an oxygen atom or -NT _α -Group (T _α Represents a hydrogen atom or a substituent on a nitrogen atom. ).
(3) K _α And L _α Are the same or different and each represents a hydrogen atom or a substituent on a carbon atom; _α And L _α And may be a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (I'-2)

[Where T _α Represents the same meaning as described above, and L _β Represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (I'-3)

[Where T _α Represents the same meaning as described above, and L _γ Represents a C1-C10 alkyl group. ]
A group represented by
Formula (I'-4)

[Where T _α Represents the same meaning as described above. ]
A group represented by
Formula (I'-5)

[Where T _α Represents the same meaning as described above, and K _β Represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (I'-6)

[Where W _α Represents the same meaning as described above, and K _γ And L _δ Is a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (I'-7)

[Where Q _α And W _α Represents the same meaning as described above, and K _δ And L _ε Is -V _α = V _α '-V _α '' = V _α '''-Group (V _α , V _α ', V _α '' And V _α '''Represents the same or different methine group which may be substituted, or -N = group, and V _α , V _α ', V _α '' And V _α At least one of '''represents a -N = group. ). ]
A group represented by
Formula (I'-8)

[Where T _α Represents the same meaning as above, Q _β Represents a hydroxyl group which may be substituted. ]
Or a group represented by
Formula (I'-9)

[Where W _α Represents the same meaning as described above. ]
Represents a group represented by
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A composition for inhibiting transcription of an extracellular matrix gene, comprising a cinnamoyl compound represented by the formula (1) and an inert carrier.
10. Formula (II ')

(E ₀ ) -Group {e ₀ Is a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, -NR ₁ -Group (R ₁ Represents the same meaning as described above. ), A 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group. }, R _d 'R _d Same or different from R _d Represents the same meaning as }. }, M _c0 -B _a -Group (M _c0 And B _a Represents the same meaning as described above. ), M _c0 —CO— group (M _c0 Represents the same meaning as described above. ), M _c0 -CO-O- group (M _c0 Represents the same meaning as described above. ), M _c0 O-CO- group (M _c0 Represents the same meaning as described above. ), M _c0 R _e N-group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 -CO-NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 O-CO-NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 R _e N-CO- group (M _c0 And R _e Represents the same meaning as described above. ), M _c0 R _e N-CO-NR _e '-Group (M _c0 , R _e And R _e 'Represents the same meaning as described above. ), M _c0 R _e N-C (= NR _e ') -NR _e '' -Group (M _c0 , R _e , R _e 'And R _e '' Represents the same meaning as described above. ), M _c0 -SO ₂ -NR _e -Group (M _c0 And R _e Represents the same meaning as described above. ) Or M _c0 R _e N-SO ₂ -Group (M _c0 And R _e Represents the same meaning as described above. ) And R _d Represents the same meaning as described above. ].
(3) Z ₀ Group: may have a halogen atom, C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group, A 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring and a group condensed with the α ring.
II. β 'is
Formula (II'-1)

[Where:
(1) Q _α Represents an optionally substituted hydroxyl group or an optionally substituted amino group.
(2) W _α Is an oxygen atom or -NT _α -Group (T _α Represents a hydrogen atom or a substituent on a nitrogen atom. ).
(3) K _α And L _α Are the same or different and each represents a hydrogen atom or a substituent on a carbon atom; _α And L _α And may be a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (II'-2)

[Where T _α Represents the same meaning as described above, and L _β Represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (II'-3)

[Where T _α Represents the same meaning as described above. ]
A group represented by
Formula (II'-5)

[Where T _α Represents the same meaning as described above, and K _β Represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (II'-6)

[Where W _α Represents the same meaning as described above, and K _γ And L _δ Is a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (II'-7)

[Where Q _α And W _α Represents the same meaning as described above, and K _δ And L _ε Is -V _α = V _α '-V _α '' = V _α '''-Group (V _α , V _α ', V _α '' And V _α '''Represents the same or different methine group which may be substituted, or -N = group, and V _α , V _α ', V _α '' And V _α At least one of '''represents a -N = group. ). ]
A group represented by
Formula (II'-8)

[Where T _α Represents the same meaning as above, Q _β Represents a hydroxyl group which may be substituted. ]
Or a group represented by
Formula (II'-9)

[Where W _α Represents the same meaning as described above. ]
Represents a group represented by
However, when α is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:
11. Formula (V ')

[Where:
I. a represents a thiophene ring, a furan ring, a pyrrole ring or a tetrazole ring; _a Is a C1-C10 alkyl group substituted with a cyano group, a C1-C10 alkyl group substituted with a tetrahydropyran-4-ylidene group, or a C2-C10 alkenyl group substituted with a halogen atom or a cyano group, Or a C2-C10 alkenyl group substituted with a C1-C10 alkoxycarbonyl group, a C3-C10 alkynyl group substituted with a hydroxy group, or a ₀ -R ₁ -B-r ₁ '-Group {a ₀ Is a methyl group substituted with a C1-C10 alkylthio group, a methyl group substituted with a C1-C10 alkylsulfinyl group, a methyl group substituted with a C1-C10 alkylsulfonyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group Group, r ₂ O—CO— group (r ₂ Represents a C1-C10 alkyl group or a C2-C10 alkyl group substituted with a hydroxyl group. ), A carboxy group, an rr′N—CO— group (r and r ′ are the same or different and each represents a hydrogen atom or a C1-C10 alkyl group), a ₁ -NH-CO- group (a ₁ Represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group. ), A ₁ '-CO- group (a ₁ 'Represents a morpholino group. ), Rr'N-CH ₂ -Group (r and r 'are as defined above), r ₀ -(O) _l -CONH-CH ₂ -Group (r ₀ Represents a C1-C10 alkyl group, and l represents 0 or 1. ), R-OCH ₂ -Group (r represents the same meaning as described above), r ₀ —CO— group (r ₀ Represents the same meaning as described above. ), A cyano group or a sulfomethyl group, r ₁ Represents a C1-C10 alkylene group, r ₁ 'Represents a single bond or a C1-C10 alkylene group, and b represents an oxy group, a thio group, a sulfinyl group, a sulfonyl group, or an imino group. } Or a ₂ -Y-CO-NH- group (a ₂ Represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group, and y represents an oxy group or an imino group. ) Or rO—COCO—NH— group (where r represents the same meaning as described above), or a ₃ -Z-NH- group (a ₃ Represents a C2-C10 alkenyl group, or a C1-C10 alkoxy group substituted with a C1-C10 alkoxy group, a C1-C10 alkoxycarbonyl group, a carboxy group or a cyano group, and z represents a carbonyl group or a sulfonyl group. . ) Or a ₄ -Nr'CO- group {a ₄ Is a C1-C10 alkoxy group, a C3-C10 alkenyloxy group, or r ₀ -SO ₂ -Group (r ₀ Represents the same meaning as described above. ), Or a C2-C10 alkyl group substituted with a hydroxyl group or a C1-C10 alkoxy group, or r ₀ r ₀ 'N-group (r ₀ Represents the same meaning as described above, and r ₀ 'R ₀ Same as or different from r ₀ Represents the same meaning as ) -Substituted C2-C10 alkyl group, or rO-CO- group (where r represents the same meaning as described above), a C1-C10 alkyl group substituted with a cyano group or an aminocarbonyl group, or rO-CO- (rO-COCH ₂ ) CH— group (wherein r represents the same meaning as described above), and r ′ represents the same meaning as described above. } Or a ₅ -NHSO ₂ -Group (a ₅ Represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group. ) Or r ₀ ON = CH-group (r ₀ Represents the same meaning as described above. ) Or r ₀ NHCSNH-group (r ₀ Represents the same meaning as described above. ) Or r ₀ NHC (-Sr ₀ ') = N-group (r ₀ And r ₀ 'Represents the same meaning as described above. ) Or (rO) ₂ P (= O) CH ₂ -Represents a group (r represents the same meaning as described above), p represents 0, 1, 2 or 3, and when p is 2 or more, X _a Are the same or different,
Y _a Is a halogen atom, a C1-C10 alkyl group that may be substituted with a halogen atom, a C1-C10 alkyl group that may be substituted with a C1-C10 alkoxy group, or a C2-C10 alkenyl group, or A C2-C10 alkynyl group, a 2-oxo-oxazolidin-3-yl group, a [1,3] dioxolan-2-yl group, or a C1-C10 alkoxy group substituted with a morpholino group, or a ₀ '-B'-group (a ₀ 'Represents a C1-C10 alkyl group which may be substituted with a halogen atom, and b' represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group. ), A nitro group, a cyano group, or an rO—CO— group (where r represents the same meaning as described above), or r ₀ r ₀ 'N-group (r ₀ And r ₀ 'Represents the same meaning as described above. ) Or r ₀ CO—NH— group (r ₀ Represents the same meaning as described above. ) Or r ₀ r ₀ 'NCONH-group (r ₀ And r ₀ 'Represents the same meaning as described above. ) Or rr′NCO— group (r and r ′ represent the same meaning as described above) or a hydroxyl group, q represents 0, 1, 2 or 3, and q is 2 or more. When Y _a Are the same or different, and when q is 2 or more, adjacent Y _a May be condensed with ring a to form a 2,3-dihydro-benzo [1,4] dioxin ring.
II. b '
Formula (V'-1)

[Where Q _a R _a —O— group {r _a Is a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, or r ₀ r ₀ 'N-CH ₂ -Group (r ₀ And r ₀ 'Represents the same meaning as described above. ), ROCH ₂ -Group (r represents the same meaning as described above), r ₀ —CO— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group, a C1-C10 alkyl group substituted with a cyano group, or r ₃ -R ₁ -Group (r ₃ Represents a phenyl group or a pyridyl group, and r ₁ Represents the same meaning as described above. ). }, Or a piperidino group, or a morpholino group, or r ₄ r ₄ 'N-group (r ₄ And r ₄ 'Is the same or different and is a C2-C10 alkyl substituted with a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C1-C10 alkoxy group. Represents a group. However, it does not become a hydrogen atom at the same time. ) And W _a Is an oxygen atom or -NT _a -Group [T _a R _b -Group (r _b R _a Same as or different from r _a Represents the same meaning as Or r ₃ '-Group (r ₃ 'R ₃ Same as or different from r ₃ Represents the same meaning as ). ] And K _a Represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group; _a Represents a hydrogen atom or a C1-C10 alkyl group, and K _a And L _a And may form a C3-C10 alkylene group or a 1,3-butadienylene group. ]
A group represented by
Formula (V'-2)

[Where T _a Represents the same meaning as described above, and L _b Represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (V'-3)

[Where T _a Represents the same meaning as described above, and L _c Represents a C1-C10 alkyl group. ]
A group represented by
Formula (V'-4)

[Where T _a Represents the same meaning as described above. ]
A group represented by
Formula (V'-5)

[Where T _a Represents the same meaning as described above, and K _b Represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (V'-6)

[Where W _a Represents the same meaning as described above, and K _c And L _d And C3-C10 alkylene group or C4-C10 alkenylene group. ]
A group represented by
Formula (V'-7)

[Where Q _a And W _a Represents the same meaning as described above, and K _d And L _e Is -V _a = V _a '-V _a '' = V _a '''-Group (V _a , V _a ', V _a '' And V _a '''Is the same or different and represents a methine group or -N = group; _a , V _a ', V _a '' And V _a At least one of '''represents a -N = group. ). ]
A group represented by
Formula (V'-8)

[Where T _a Represents the same meaning as above, Q _b R _a —O— group (r _a Represents the same meaning as described above. ). ]
Or a group represented by
Formula (V-9 ')

[Where W _a Represents the same meaning as described above. ]
Represents a group represented by
However, when a is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:
12 An extracellular matrix gene transcription repressing composition comprising the compound according to any one of 2 to 6, 10 and 11 and an inert carrier.
13. 12. An extracellular matrix gene transcription repressing composition comprising the compound according to 5 or 11 above and an inert carrier.
14 10. Use of a cinnamoyl compound contained as an active ingredient in the composition according to 1 or 9 above as an active ingredient for suppressing transcription of an extracellular matrix gene.
15. 12. Use of the compound according to the above items 2 to 6, 10 and 11 as an active ingredient for suppressing transcription of an extracellular matrix gene.
16. Use of the compound according to 5 or 11 above as an active ingredient for suppressing transcription of an extracellular matrix gene.
17. It is contained as an active ingredient in the composition of the preceding paragraphs 1 and 9 as an active ingredient for improving tissue fibrosis by reducing the amount of extracellular matrix gene expression and reducing the amount of extracellular matrix accumulation. Use of cinnamoyl compounds.
18. 12. Use of the compound according to the above item 2-6, 10 or 11 as an active ingredient for improving tissue fibrosis by reducing the amount of extracellular matrix gene expression and reducing the amount of extracellular matrix accumulation.
19. 10. An improvement in tissue fibrosis, comprising administering an effective amount of a cinnamoyl compound contained as an active ingredient in the composition according to the above 1 and 9 to a mammalian patient in need of a treatment that improves tissue fibrosis. Method.
20. 12. A method for improving tissue fibrosis, comprising administering an effective amount of the compound described in the above item 2-6, 10 or 11 to a mammalian patient in need of treatment for improving tissue fibrosis.
21. A therapeutic agent for chronic renal failure, comprising a cinnamoyl compound contained as an active ingredient in the composition according to items 1 and 9, or a compound according to items 2 to 6, 10 and 11, and an inert carrier. .
22. Use of the cinnamoyl compound contained as an active ingredient in the composition of the preceding clause 1 and 9, or the compound of the preceding clause 2-6, 10 and 11 as an active ingredient for treating chronic renal failure.
23. An effective amount of the cinnamoyl compound contained as an active ingredient in the composition according to 1 or 9 above or the compound according to 2 to 6, 10 or 11 above to a mammalian patient in need of treatment for chronic renal failure. A method for treating chronic renal failure, comprising administering.
24. A therapeutic agent for heart failure, comprising a cinnamoyl compound contained as an active ingredient in the composition according to the above 1 or 9, or a compound according to the above 2 to 6, 10 and 11, and an inert carrier.
25. Use of the cinnamoyl compound contained as an active ingredient in the composition of the preceding clause 1 and 9, or the compound of the preceding clause 2-6, 10 and 11 as an active ingredient for treating heart failure.
26. An effective amount of the cinnamoyl compound contained as an active ingredient in the composition according to 1 or 9 above or the compound according to 2 to 6, 10 or 11 above is administered to a mammalian patient in need of therapeutic treatment for heart failure. A method for treating heart failure characterized by the above.
27. 10. A TGF-β action-suppressing composition comprising a cinnamoyl compound contained as an active ingredient in the composition according to the above 1 and 9 and an inert carrier.
28. 12. A TGF-β action-suppressing composition comprising the compound according to the above 2-6, 10 and 11 and an inert carrier.
29. Use of the cinnamoyl compound contained as an active ingredient in the composition of said 1 and 9 as an active ingredient for suppressing the effect | action of TGF- (beta).
30. 12. Use of the compound according to the above item 2 to 6, 10 and 11 as an active ingredient for suppressing the action of TGF-β.
31. 10. A hair nourishing composition comprising a cinnamoyl compound contained as an active ingredient in the composition according to the preceding item 1 or 9, or a compound according to the preceding item 2-6, 10 and 11, and an inert carrier.
32. It is contained as an active ingredient in the composition of the preceding paragraphs 1 and 9 as an active ingredient for obtaining a hair nourishing effect by inhibiting the promotion of the transition to the hair regression stage by TGF-β and leading to the extension of the hair growth stage. Cinnamoyl compound, or the use of a compound according to the preceding items 2-6, 10 and 11.
33. An effective amount of the cinnamoyl compound contained as an active ingredient in the composition according to the above 1 or 9 or the compound according to the above 2 to 6, 10 or 11 is administered to a mammalian patient in need of hair restoration treatment. A hair nourishing method characterized by:
Etc. are provided.

本発明により、組織における細胞外マトリックス遺伝子の発現量を減少させ、細胞外マトリックス蓄積量を低下させることにより、組織の線維化を改善させる組成物（即ち、細胞外マトリックス蓄積抑制剤や、線維症治療剤又は心不全治療剤）等の開発・提供が可能となる。 According to the present invention, a composition for improving tissue fibrosis by reducing the amount of extracellular matrix gene expression in a tissue and decreasing the amount of extracellular matrix accumulation (ie, an extracellular matrix accumulation inhibitor, fibrosis) Development or provision of therapeutic agents or therapeutic agents for heart failure).

以下、本発明を詳細に説明する。
本発明において、アルキル基、ハロアルキル基、アルコキシ基、アルコキシカルボニル基、アルキルチオ基、アルキルスルフィニル基、アルキルスルホニル基及びアルキレン基における飽和炭化水素基は、分枝していてもよく、またその炭素原子の一部又は全部で環を形成してもよく、アルケニル基、アルケニルオキシ基、アルキニル基、アルキニルオキシ基、アルケニレン基及びアルキニレン基における不飽和炭化水素基は、分枝をもっていてもよく、またその炭素原子の一部又は全部で環を形成してもよく、その不飽和結合数は単数又は複数である。
本発明において、アルキル基としては、例えば、メチル基、エチル基、イソプロピル基、シクロヘキシル基、シクロプロピルメチル基等があげられ、ハロアルキル基としては、例えば、２，２，２−トリフルオロエチル基等があげられ、アルコキシ基としては、例えば、メトキシ基、エトキシ基、シクロペンチルオキシ基、２−シクロヘキシルエトキシ等があげられ、アルキルチオ基としては、例えば、メチルチオ基等があげられ、アルキルスルフィニル基としては、例えば、メチルスルフィニル基等があげられ、アルキルスルホニル基としては、例えば、メチルスルホニル基等があげられ、アルキレン基としては、例えば、メチレン基、エチルエチレン基、１，４−シクロヘキシレン基等があげられ、、アルケニル基としては、例えば、ビニル基、２−プロペニル基、３−メチル−２−ブテニル基、１，３−ブタジエニル基、３−シクロヘキセニル基等があげられ、アルキニル基としては、例えば、エチニル基、２−プロピニル基、２−ペンテン−４−イニル基等があげられ、アルケニレン基としては、例えば、ビニレン基、プロペニレン、１，３−ブタジエニレン基等があげられ、アルキニレン基としては、例えば、エチニレン基、プロピニレン基等があげられる。
本発明において、ハロゲン原子としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子があげられる。
本発明において、ピリジル基は、２−ピリジル基、３−ピリジル基及び４−ピリジル基を含み、フリル基は、２−フリル基及び３−フリル基を含み、チエニル基は、２−チエニル基及び３−チエニル基を含み、ナフチル基は、１−ナフチル基及び２−ナフチル基を含む。 Hereinafter, the present invention will be described in detail.
In the present invention, the saturated hydrocarbon group in the alkyl group, haloalkyl group, alkoxy group, alkoxycarbonyl group, alkylthio group, alkylsulfinyl group, alkylsulfonyl group and alkylene group may be branched, and The unsaturated hydrocarbon group in the alkenyl group, alkenyloxy group, alkynyl group, alkynyloxy group, alkenylene group and alkynylene group may have a branch, and the carbon thereof may form a ring partially or entirely. A part or all of the atoms may form a ring, and the number of unsaturated bonds is one or more.
In the present invention, examples of the alkyl group include a methyl group, an ethyl group, an isopropyl group, a cyclohexyl group, and a cyclopropylmethyl group. Examples of the haloalkyl group include a 2,2,2-trifluoroethyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, a cyclopentyloxy group, 2-cyclohexylethoxy, and the like. Examples of the alkylthio group include a methylthio group. Examples of the alkylsulfinyl group include: For example, a methylsulfinyl group and the like can be mentioned. Examples of the alkylsulfonyl group include a methylsulfonyl group. Examples of the alkylene group include a methylene group, an ethylethylene group, and a 1,4-cyclohexylene group. As the alkenyl group, for example, bi Group, 2-propenyl group, 3-methyl-2-butenyl group, 1,3-butadienyl group, 3-cyclohexenyl group and the like. Examples of the alkynyl group include ethynyl group, 2-propynyl group, 2 -Pentene-4-ynyl group and the like, examples of the alkenylene group include vinylene group, propenylene, 1,3-butadienylene group, and examples of the alkynylene group include ethynylene group and propynylene group. It is done.
In the present invention, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
In the present invention, the pyridyl group includes a 2-pyridyl group, a 3-pyridyl group and a 4-pyridyl group, the furyl group includes a 2-furyl group and a 3-furyl group, the thienyl group includes a 2-thienyl group and It includes a 3-thienyl group, and the naphthyl group includes a 1-naphthyl group and a 2-naphthyl group.

式（I）、（II）、（III）、（IV）、（V）、（I’）及び（II’）で示されるシンナモイル化合物（以下、各々、化合物（I）、（II）、（III）、（IV）、（V）、（I’）及び（II’）と記すこともある）において、α環、Ａ０環、Ａ環及びａ環が窒素原子を２以上有する芳香族６員環の場合は、そのＮ−オキシドも含む。
化合物（I）〜（V）、（I’）及び（II’）のα環、Ａ０環、Ａ環及びａ環において、芳香族５員環としては、例えば、チオフェン環、フラン環、ピロール環、イミダゾール環、ピラゾール環、１，２，３−トリアゾール環、１，２，４−トリアゾール環、テトラゾール環、オキサゾール環、イソオキサゾール環、チアゾール環、イソチアゾール環、フラザン環、１，２，５−チアジアゾール環等があげられ、窒素原子を２以上有する芳香族６員環としては、例えば、ピリダジン環、ピリミジン環、ピラジン環、１，３，５−トリアジン環、１，２，４−トリアジン環等があげられる。 Cinnamoyl compounds represented by formulas (I), (II), (III), (IV), (V), (I ′) and (II ′) (hereinafter referred to as compounds (I), (II), ( (III), (IV), (V), (I ′) and (II ′)), the α ring, the A0 ring, the A ring and the a ring have 6 or more aromatic nitrogen atoms. In the case of a ring, the N-oxide is also included.
In the α ring, A0 ring, A ring and a ring of the compounds (I) to (V), (I ′) and (II ′), examples of the aromatic 5-membered ring include a thiophene ring, a furan ring and a pyrrole ring. Imidazole ring, pyrazole ring, 1,2,3-triazole ring, 1,2,4-triazole ring, tetrazole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, furazane ring, 1,2,5 -Thiadiazole ring and the like, and examples of the aromatic 6-membered ring having two or more nitrogen atoms include pyridazine ring, pyrimidine ring, pyrazine ring, 1,3,5-triazine ring, 1,2,4-triazine ring Etc.

式（I）〜（VI）、（I’）、（II’）及び（V’）で示されるシンナモイル化合物（以下、化合物（I）〜（VI）、（I’）、（II’）及び（V’）と記すこともある）は、それらの薬理学上許容されうる塩も、同時に表す。薬理学上許容されうる塩とは、化合物（I）〜（VI）、（I’）、（II’）及び（V’）（以下、本発明化合物と記すこともある）の、無機酸との塩、有機酸との塩、無機塩基との塩又は有機塩基との塩を表す。無機酸との塩とは、例えば、塩酸塩、臭化水素酸塩等があげられ、有機酸との塩とは、例えば、酢酸塩、安息香酸塩等があげられ、無機塩基との塩とは、例えば、カリウム塩、ナトリウム塩等があげられ、有機塩基との塩とは、例えば、ピリジン塩、モルホリン塩等があげられる。 Cinnamoyl compounds represented by the formulas (I) to (VI), (I ′), (II ′) and (V ′) (hereinafter, compounds (I) to (VI), (I ′), (II ′) and (Sometimes referred to as (V ′)) also represents their pharmacologically acceptable salts. The pharmacologically acceptable salt is an inorganic acid of the compounds (I) to (VI), (I ′), (II ′) and (V ′) (hereinafter sometimes referred to as the compound of the present invention). A salt with an organic acid, a salt with an inorganic base, or a salt with an organic base. Examples of the salt with an inorganic acid include hydrochloride and hydrobromide. Examples of the salt with an organic acid include acetate and benzoate. Examples include potassium salts and sodium salts, and examples of salts with organic bases include pyridine salts and morpholine salts.

化合物（III）におけるＸ_Ａ０、Ｙ_Ａ０、Ｑ_Ａ０、Ｋ_Ａ０、Ｌ_Ａ０及びＴ_Ａ０は、互いに独立に、Ｄ_１、Ｄ_２、Ｄ_３，Ｄ_４，Ｄ_５、Ｒ_０、Ｒ_０’、Ｒ_０’’、Ｒ_１、Ｒ_１’、Ｒ_１’’、Ｒ_２、Ｒ_２’、Ｒ_３、Ｒ_４、Ｒ_４’、Ｒ_５、Ｒ_６、Ａ_１、Ａ_２、Ａ_３、Ａ_４、Ａ_５、Ａ_６、Ａ_７、Ａ_７’、Ａ_７’’、Ａ_８、Ａ_８’、Ａ_９、Ａ_９’、Ａ_９’’、Ａ_１０、Ａ_１０’、Ａ_１１、Ｂ、Ｂ’、Ｂ_０、Ｂ_１、Ｂ_１’、Ｂ_２、Ｂ_２’、Ｂ_３、Ｂ_３’、Ｂ_４、Ｂ_４’、Ｂ_５、Ｂ_６、（ａ_０）、（ｂ_０）、（ｃ_０）、（ｄ_０）、（ｅ_０）、Ｍ_ａ、Ｍ_ａ’、Ｍ_ａ’’、Ｍ_ａ’’’、Ｍ_ａ’’’’、Ｍ_ｂ０、Ｍ_ｃ０、Ｍ_ｄ０、Ｒ_ａ０、Ｒ_ｂ、Ｒ_ｃ、Ｒ_ｄ、Ｒ_ｄ’、Ｒ_e、Ｒ_e’、Ｒ_e’’、Ｒ_e’’’、Ｂ_ａ、Ｂ_ｂ、Ｂ_ｃ、Ｙ_ａ、Ｙ_ａ’、Ｙ_ｂ、Ｙ_ｂ’、Ｙ_ｂ’’、Ｙ_ｃ及びＹ_ｃ’で表される基、及び、ｋ、ｋ’、ｌ、ｍ、ｍ’、ｎ及びｎ’で表される整数によって表される。
化合物（IV）におけるＸ_Ａ、Ｙ_Ａ、Ｑ_Ａ、Ｋ_Ａ、Ｌ_Ａ及びＴ_Ａは、互いに独立に、Ｄ_１、Ｄ_２、Ｄ_３，Ｄ_４，Ｄ_５、Ｒ_０、Ｒ_０’、Ｒ_０’’、Ｒ_１、Ｒ_１’、Ｒ_１’’、Ｒ_２、Ｒ_２’、Ｒ_３、Ｒ_４、Ｒ_４’、Ｒ_５、Ｒ_６、Ａ_１、Ａ_２、Ａ_３、Ａ_４、Ａ_５、Ａ_６、Ａ_７、Ａ_７’、Ａ_７’’、Ａ_８、Ａ_８’、Ａ_９、Ａ_９’、Ａ_９’’、Ａ_１０、Ａ_１０’、Ａ_１１、Ｂ、Ｂ’、Ｂ_０、Ｂ_１、Ｂ_１’、Ｂ_２、Ｂ_２’、Ｂ_３、Ｂ_３’、Ｂ_４、Ｂ_４’、Ｂ_５、Ｂ_６、（ａ）、（ｂ）、（ｃ）、（ｄ）、（ｅ）、Ｍ_ａ、Ｍ_ａ’、Ｍ_ａ’’、Ｍ_ａ’’’、Ｍ_ａ’’’’、Ｍ_ｂ、Ｍ_ｃ、Ｍ_ｄ、Ｒ_ａ、Ｒ_ｂ、Ｒ_ｃ、Ｒ_ｄ、Ｒ_ｄ’、Ｒ_e、Ｒ_e’、Ｒ_e’’、Ｒ_e’’’、Ｂ_ａ、Ｂ_ｂ、Ｂ_ｃ、Ｙ_ａ、Ｙ_ａ’、Ｙ_ｂ、Ｙ_ｂ’、Ｙ_ｂ’’、Ｙ_ｃ及びＹ_ｃ’で表される基、及び、ｋ、ｋ’、ｌ、ｍ、ｍ’、ｎ及びｎ’で表される整数によって表される。
化合物（V）及び（V’）におけるＸ_ａ、Ｙ_ａ、ｑ_ａ及びｔ_ａは、互いに独立に、ａ_０、ａ_０’、ａ_１、ａ_１’、ａ_２、ａ_３、ａ_４、ａ_５、ｂ、ｂ’、ｒ、ｒ’、ｒ_０、ｒ_０’、ｒ_１、ｒ_１’、ｒ_２、ｒ_３、ｒ_３’、ｒ_４、ｒ_４’、ｒ_ａ、ｒ_ｂ、ｙ及びｚで表される基、及び、ｌで表される整数によって表される。 X _A0 , Y _A0 , Q _A0 , K _A0 , L _A0 and T _A0 in the compound (III) are each independently D ₁ , D ₂ , D ₃ , D ₄ , D ₅ , R ₀ , R ₀ ′, _{_{R 0 '', R 1,}} R 1 ', R 1'', R 2, R 2', R 3, R 4, R 4 ', R 5, R 6, A 1, A 2, A 3, A ₄ , A ₅ , A ₆ , A ₇ , A ₇ ′, A ₇ ″, A ₈ , A ₈ ′, A ₉ , A ₉ ′, A ₉ ″, A ₁₀ , A ₁₀ ′, A ₁₁ , B , B ′, B ₀ , B ₁ , B ₁ ′, B ₂ , B ₂ ′, B ₃ , B ₃ ′, B ₄ , B ₄ ′, B ₅ , B ₆ , (a ₀ ), (b ₀ ) , (C ₀ ), (d ₀ ), (e ₀ ), M _a , M _a ′, M _a ″, M _a ″ ″, M _a ″ ″, M _b0 , M _c0 , M _d0 , _{_{_{_{R a0, R b, R c}}}} , R d, R d ', R e, R e', R e '', R e ''', B a, B b _{_{_{B c, Y a, Y a}}} ', Y b, Y b', Y b ' groups represented by', _{Y c} and _{Y c} ', and, k, k', l, m, m ', n and It is represented by an integer represented by n ′.
In the compound (IV), X _A , Y _A , Q _A , K _A , L _A and T _A are independently of each other, D ₁ , D ₂ , D ₃ , D ₄ , D ₅ , R ₀ , R ₀ ′, _{_{R 0 '', R 1,}} R 1 ', R 1'', R 2, R 2', R 3, R 4, R 4 ', R 5, R 6, A 1, A 2, A 3, A ₄ , A ₅ , A ₆ , A ₇ , A ₇ ′, A ₇ ″, A ₈ , A ₈ ′, A ₉ , A ₉ ′, A ₉ ″, A ₁₀ , A ₁₀ ′, A ₁₁ , B , B ′, B ₀ , B ₁ , B ₁ ′, B ₂ , B ₂ ′, B ₃ , B ₃ ′, B ₄ , B ₄ ′, B ₅ , B ₆ , (a), (b), ( c), (d), (e), M _a , M _a ′, M _a ″, M _a ″ ″, M _a ″ ″, M _b , M _c , M _d , R _a , R _b , R _c , R _d , R _d ′, R _e , R _e ′, R _e ″, R _e ′ ″, B _a , B _b , B _c , Y _a , Y _a ′, Y _b , Y _b ' , Y _b ″, Y _c and Y _c ′, and integers represented by k, k ′, l, m, m ′, n and n ′.
Compound (V) and (V ') _X a _in, Y a, _{q a} and _{t a} are, independently of one _{_{_{another, a 0, a 0',}}} a 1, a 1 ', a 2, a 3, a 4, a ₅ , b, b ′, r, r ′, r ₀ , r ₀ ′, r ₁ , r ₁ ′, r ₂ , r ₃ , r ₃ ′, r ₄ , r ₄ ′, r _a , r _b , It is represented by a group represented by y and z and an integer represented by l.

化合物（I）、（II）、（I’）及び（II’）のＹ_αのとりうる置換基Ｙ_０群において、「６−１０員環のアリール基」とは、単環又は縮合環の芳香族炭化水素環をなす基を表し、例えば、フェニル基、１−ナフチル基、２−ナフチル基、６−インダニル基等があげられ、「５−１０員環のヘテロアリール基」とは、単環又は縮合環の芳香族複素環をなす基を表し、例えば、２−フリル基、３−フリル基、２−チエニル基、３−チエニル基２−ピリジル基、３−ピリジル基、４−ピリジル基、２−キノリル基等があげられ、「不飽和結合を含んでもよい３−１０員環の炭化水素環若しくは複素環をなす基」とは、単環又は縮合環を含み、２−シクロヘキセニル基、２−モルホリニル基、４−ピペリジル基等があげられ、これらは単数又は同一又は相異なる複数の前記のＭ_ａ−基で置換されてもよい。
化合物（I）及び（II）のＹ_αのとりうる置換基Ｚ_０群において、「Ａ環と縮環する基」は、ハロゲン原子、C1-C10アルコキシ基、C3-C10アルケニルオキシ基、C3-C10アルキニルオキシ基、カルボニル基、チオカルボニル基、オキシ基、チオ基、スルフィニル基若しくはスルホニル基から選ばれる、単数又は同一又は相異なる複数の原子又は基を有してもよい。
化合物（III）のＸ_Ａ０のとりうる置換基Ｅ_０群のＲ_ａ０において、「置換されてもよい５−７員環のアリール基又はヘテロアリール基」とは、単環又は縮合環の芳香族炭化水素環をなす基又は単環又は縮合環の芳香族複素環をなす基を表し、例えば、フェニル基、１−ナフチル基、２−ナフチル基、６−インダニル基、２−フリル基、３−フリル基、２−チエニル基、３−チエニル基、２−ピリジル基、３−ピリジル基、４−ピリジル基、２−キノリル基等があげられ、これらは単数又は同一又は相異なる複数の前記のＭ_ａ−基で置換されてもよい。 In the group Y ₀ that Y _α of compounds (I), (II), (I ′) and (II ′) can take, “6- to 10-membered aryl group” means a monocyclic or condensed ring Represents a group that forms an aromatic hydrocarbon ring, and includes, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 6-indanyl group, and the like. Represents a group forming a ring or condensed aromatic heterocycle, for example, 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group 2-pyridyl group, 3-pyridyl group, 4-pyridyl group , 2-quinolyl group, etc., and “the group that forms a 3-10 membered hydrocarbon ring or heterocyclic ring that may contain an unsaturated bond” includes a monocyclic ring or a condensed ring, and includes a 2-cyclohexenyl group , 2-morpholinyl group, 4-piperidyl group, etc., which are singular or the same or phase Comprising a plurality of said M _a - may be substituted with group.
In the group Z _{0 of} possible substituents of Y _{α in} the compounds (I) and (II), the “group condensed with the A ring” is a halogen atom, a C1-C10 alkoxy group, a C3-C10 alkenyloxy group, a C3- A C10 alkynyloxy group, a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a sulfinyl group or a sulfonyl group may have a single atom, or the same or different plural atoms or groups.
In the R _a0 group of the substituent E ₀ group that can be taken by X _A0 of the compound (III), the “ _optionally substituted 5- to 7-membered aryl group or heteroaryl group” means a monocyclic or condensed aromatic ring Represents a group forming a hydrocarbon ring or a group forming a monocyclic or condensed aromatic heterocyclic ring, such as a phenyl group, 1-naphthyl group, 2-naphthyl group, 6-indanyl group, 2-furyl group, 3- A furyl group, a 2-thienyl group, a 3-thienyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-quinolyl group, and the like. These include one or a plurality of the same or different Ms. _It may be substituted with _a group.

化合物（I）、（II）、（III）、（I’）及び（II’）の、Ｙ_α及びＹ_Ａ０のとりうる置換基Ｙ_０群の（ｄ_０）において、「カルボニル基又はチオカルボニル基で置換され、更に、オキシ基、チオ基、−ＮＲ_１-基（Ｒ_１は、前記と同一の意味を表す。）、スルフィニル基若しくはスルホニル基で置換されてもよい５−１２員の炭化水素環をなす」は、炭素原子の一つ又は複数が、カルボニル基又はチオカルボニル基で置き換えられ、更に、炭素原子の一つ又は複数が、オキシ基、チオ基、−ＮＲ_１-基（Ｒ_１は、前記と同一の意味を表す。）、スルフィニル基若しくはスルホニル基から選ばれた、単数又は同一又は相異なる複数の基で置き換えられてもよい５−１２員の炭化水素環をなすことを表す。
化合物（I）、（II）、（III）、（I’）及び（II’）の、Ｙ_α及びＹ_Ａ０のとりうる置換基Ｙ_０群の（ｅ_０）において、「カルボニル基、チオカルボニル基、オキシ基、チオ基、−ＮＲ_１-基（Ｒ_１は、前記と同一の意味を表す。）、スルフィニル基若しくはスルホニル基で置換されてもよい５−１２員の炭化水素環をなす。」とは、炭素原子の一つ又は複数が、カルボニル基、チオカルボニル基、オキシ基、チオ基、−ＮＲ_１-基（Ｒ_１は、前記と同一の意味を表す。）、スルフィニル基若しくはスルホニル基から選ばれた、単数又は同一又は相異なる複数の基で置き換えられてもよい５−１２員の炭化水素環をなすことを表す。 In the compound (I), (II), (III), (I ′) and (II ′) (d ₀ ) of the substituent Y ₀ group that Y _α and Y _A0 can take, “carbonyl group or thiocarbonyl” A 5- to 12-membered carbon atom which may be further substituted with an oxy group, a thio group, an —NR ₁ — group (R ₁ represents the same meaning as described above), a sulfinyl group or a sulfonyl group. In the “forming a hydrogen ring”, one or more of carbon atoms are replaced with a carbonyl group or a thiocarbonyl group, and one or more of carbon atoms are replaced with an oxy group, a thio group, a —NR ₁ — group (R ₁ represents the same meaning as described above), and forms a 5- to 12-membered hydrocarbon ring which may be replaced with a single group or a plurality of the same or different groups selected from a sulfinyl group or a sulfonyl group. To express.
In the compounds (I), (II), (III), (I ′) and (II ′) (e ₀ ) in the group Y _{0 which} Y _α and Y _A0 can take, “carbonyl group, thiocarbonyl” It forms a 5- to 12-membered hydrocarbon ring which may be substituted with a group, an oxy group, a thio group, an —NR ₁ — group (R ₁ represents the same meaning as described above), a sulfinyl group or a sulfonyl group. "Means that one or more of the carbon atoms are a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a -NR ₁ -group (R ₁ is as defined above), a sulfinyl group or a sulfonyl group. It represents forming a 5- to 12-membered hydrocarbon ring which may be replaced by a single group or a plurality of the same or different groups selected from the group.

化合物（IV）の、Ｘ_Ａのとりうる置換基Ｂ群の（ａ）において、「オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１’−基（Ｒ_１’は、前記と同一の意味を表す。）で置換されてもよいC2-C10アルキレン基」とは、炭素原子の一つ又は複数が、オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１’−基（Ｒ_１’は、前記と同一の意味を表す。）から選ばれた、単数又は同一又は相異なる複数の基で置き換えられてもよいC2-C10アルキレン基を表し、また「オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１’−基（Ｒ_１’は、前記と同一の意味を表す。）で置換されてもよいC3-C10アルケニレン基」とは、炭素原子の一つ又は複数が、オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１’−基（Ｒ_１’は、前記と同一の意味を表す。）から選ばれた、単数又は同一又は相異なる複数の基で置き換えられてもよいC3-C10アルケニレン基を表す。
化合物（IV）の、Ｘ_Ａのとりうる置換基Ｄ群の（ｂ）において、「メチル基、オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１−基（Ｒ_１は、前記と同一の意味を表す。）で置換されてもよいC1-C10アルキレン基」とは、炭素原子の一つ又は複数がメチル基で置換されてもよい、又は、炭素原子の一つ又は複数が、オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１−基（Ｒ_１は、前記と同一の意味を表す。）から選ばれた、単数又は同一又は相異なる複数の基で置き換えられてもよいC2-C10アルキレン基を表し、「メチル基、オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１−基（Ｒ_１は、前記と同一の意味を表す。）で置換されてもよいC2-C10アルケニレン基」とは、炭素原子の一つ又は複数がメチル基で置換されてもよい、又は、炭素原子の一つ又は複数が、オキシ基、チオ基、スルフィニル基、スルホニル基若しくは−ＮＲ_１−基（Ｒ_１は、前記と同一の意味を表す。）から選ばれた、単数又は同一又は相異なる複数の基で置き換えられてもよいC2-C10アルケニレン基を表す。 In the group (a) of the substituent B group that X _A can take in the compound (IV), “oxy group, thio group, sulfinyl group, sulfonyl group or —NR ₁ ′ -group (R ₁ ′ is the same as defined above. . meaning representative of the may also be C2-C10 alkylene group "is substituted with) one or more carbon atoms, oxy, thio, sulfinyl group, a sulfonyl group or a -NR 1 _'- group (R ₁ 'Represents the same meaning as described above), and represents a C2-C10 alkylene group which may be replaced by a single group or a plurality of groups which are the same or different from each other, and “oxy group, thio group, sulfinyl group” , A sulfonyl group or a —NR ₁ ′ -group (R ₁ ′ represents the same meaning as described above), and “a C3-C10 alkenylene group which may be substituted” means that one or more carbon atoms are oxy Group, thio group, sulfinyl group, sulfonyl group -NR 1 _'- group (R _1', the a represents the same meaning.) Represents a member selected from, one or the same or different plural may be replaced with a group C3-C10 alkenylene group.
The compounds of (IV), the substituent D group can take _{X A} (b), the "methylated group, oxy group, a thio group, a sulfinyl group, a sulfonyl group or an -NR ₁ - group _{(R 1,} the same The C1-C10 alkylene group optionally substituted with a) represents that one or more carbon atoms may be substituted with a methyl group, or one or more carbon atoms may be substituted with oxy The group may be replaced with a single group or a plurality of the same or different groups selected from a group, a thio group, a sulfinyl group, a sulfonyl group, or a —NR ₁ — group (R ₁ represents the same meaning as described above). Represents a C2-C10 alkylene group, and may be substituted with a methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, or a —NR ₁ — group (where R ₁ represents the same meaning as described above). -C10 alkenylene group means a carbon atom One or more may be substituted by a methyl group, or one or more carbon atoms, oxy, thio, sulfinyl group, a sulfonyl group or an -NR 1 _- group (R ₁ is the same as the Represents a C2-C10 alkenylene group which may be replaced by a single group or a plurality of the same or different groups selected from.

化合物（I）、（II）、（I’）及び（II’）のＹ_αのとりうるＸ_０群、Ｙ_０群及びＺ_０群に属する基を、各々，下記の表２３、表２４及び表２５〜２６に例示する。
化合物（III）のＸ_Ａ０のとりうるＡ_０群、Ｂ_０群、Ｃ_０群、Ｄ_０群、Ｅ_０群、Ｆ_０群、Ｇ_０群、Ｈ_０群、Ｉ_０群、Ｊ_０群、Ｋ_０群、Ｌ_０群、Ｍ_０群及びＮ_０群に属する基を、、各々，下記の表１、表２、表３、表４、表５〜７、表８〜１１、表１２〜１５、表１６、表１７、表１８、表１９、表２０、表２１及び表２２に例示し、Ｙ_Ａ０のとりうるＸ_０群、Ｙ_０群及びＺ_０群に属する基を、各々，下記の表２３、表２４及び表２５〜２６に例示し、Ｑ_Ａ０及びＴ_Ａ０を、各々，下記の表２７〜表２８及び表２９に例示する。
化合物（IV）のＸ_ＡのとりうるＡ群、Ｂ群、Ｃ群、Ｄ群、Ｅ群、Ｆ群、Ｇ群、Ｈ群、Ｉ群、Ｊ群、Ｋ群、Ｌ群、Ｍ群及びＮ群に属する基を、、各々，下記の表１、表２、表３、表４、表５〜７、表８〜１１、表１２〜１５、表１６、表１７、表１８、表１９、表２０、表２１及び表２２に例示し、Ｙ_ＡのとりうるＸ群、Ｙ群及びＺ群に属する基を、各々，下記の表２３、表２４及び表２５〜２６に例示し、Ｑ_Ａ及びＴ_Ａを、各々，下記の表２７〜表２８及び表２９に例示する。 In the compounds (I), (II), (I ′) and (II ′), the groups belonging to the X ₀ group, the Y ₀ group and the Z ₀ group which Y _α can take are shown in the following Table 23, Table 24 and Examples are shown in Tables 25-26.
A ₀ group, B ₀ group, C ₀ group, D ₀ group, E ₀ group, F ₀ group, G ₀ group, H ₀ group, I ₀ group, J ₀ group that X _A0 of compound (III) can take, The groups belonging to the K ₀ group, the L ₀ group, the M ₀ group, and the N ₀ group are represented by the following Table 1, Table 2, Table 3, Table 4, Tables 5 to 7, Tables 8 to 11, and Tables 12 to 12, respectively. 15, Table 16, Table 17, Table 18, Table 19, Table 20, illustrated in Table 21 and Table _22, _{X 0} group can take _{Y A0,} belonging group _{Y 0} group and _{Z 0} group, respectively, the following Table 23, Table 24, and Tables 25 to 26 are exemplified, and Q _A0 and T _A0 are exemplified in the following Tables 27 to 28 and Table 29, respectively.
A, B, C, D, E, F, G, H, I, J, K, L, M, and N of Compound (IV) X _A The groups belonging to the groups are respectively shown in Table 1, Table 2, Table 3, Table 4, Table 5 to 7, Table 8 to 11, Table 12 to 15, Table 16, Table 17, Table 18, Table 19, Examples exemplified in Table 20, Table 21 and Table 22 and groups belonging to the X group, Y group and Z group that Y _A can take are exemplified in the following Table 23, Table 24 and Tables 25 to 26, respectively, and Q _A and _{T a,} respectively, illustrated in Table 27 to Table 28 and Table 29 below.

前記の、Ａ_０群〜Ｎ_０群及びＡ群〜Ｎ群に属する基を、以下の表１〜表２２に例示するが、幾何異性が可能な基の場合はその全ての幾何異性体を意味し、互変異性が可能な基の場合はその全ての互変異性体を意味する。
Ａ_０群及びＡ群に属する基を、表１に例示する。 The groups belonging to the groups A _{0 to} N _{0 and} groups A to N are exemplified in the following Tables 1 to 22. However, in the case of groups capable of geometric isomerism, all the geometric isomers are meant. In the case of a group capable of tautomerization, all tautomers thereof are meant.
Table 1 shows examples of groups belonging to the _A0 group and the A group.

Ｂ_０群及びＢ群に属する基を、表２に例示する。

Table 2 shows examples of groups belonging to the _B0 group and the B group.

Ｃ_０群及びＣ群に属する基を、表３に例示する。

Table 3 shows the groups belonging to the _C0 group and the C group.

Ｄ_０群及びＤ群に属する基を、表４に例示する。

Table 4 shows the groups belonging to the _D0 group and the D group.

Ｅ_０群及びＥ群に属する基を、表５〜表７に例示する。

Belonging group E ₀ group and E group, exemplified in Tables 5 to 7.

Ｆ_０群及びＦ群に属する基を、表８〜表１１に例示する。

Belonging group F ₀ group and F group, exemplified in Tables 8 to 11.

Ｇ_０群及びＧ群に属する基を、表１２〜表１５に例示する。

The group belonging to G ₀ group and G group, are illustrated in Table 12 to Table 15.

Ｈ_０群及びＨ群に属する基を、表１６に例示する。

Belonging group H ₀ group and H group, exemplified in Table 16.

Ｉ_０群及びＩ群に属する基を、表１７に例示する。

Table 17 illustrates the groups belonging to the _I0 group and the I group.

Ｊ_０群及びＪ群に属する基を、表１８に例示する。

Table 18 shows the groups belonging to the _J0 group and the J group.

Ｋ_０群及びＫ群に属する基を、表１９に例示する。

Table 19 shows the groups belonging to the _K0 group and the K group.

Ｌ_０群及びＬ群に属する基を、表２０に例示する。

Table 20 shows groups belonging to the _L0 group and the L group.

Ｍ_０群及びＭ群に属する基を、表２１に例示する。

Table 21 shows the groups belonging to the _M0 group and the M group.

Ｎ_０群及びＮ群に属する基を、表２２に例示する。

Table 22 shows the groups belonging to the _N0 group and the N group.

前記の、Ｘ_０群〜Ｚ_０群及びＸ群〜Ｚ群に属する基を、以下の表２３〜表２５に例示するが、幾何異性が可能な基の場合はその全ての幾何異性体を意味し、互変異性が可能な基の場合はその全ての互変異性体を意味する。
Ｘ_０群及びＸ群に属する基を、表２３に例示する。 Said, the group belonging to X ₀ group ~Z ₀ group and X groups ~Z group will be illustrated in the following table 23 to table 25, in the case of geometric isomerism group capable meaning that all geometric isomers In the case of a group capable of tautomerization, all tautomers thereof are meant.
Table 23 shows the groups belonging to the _X0 group and the X group.

Ｙ_０群及びＹ群に属する基を、表２４に例示する。

Belonging group Y ₀ group and Y group is exemplified in table 24.

Ｚ_０群又はＺ群と縮環したα環、Ａ０環又はＡ環を、表２５〜表２６に例示する。

Table 25 to Table 26 illustrate α ring, A0 ring or A ring condensed with Z ₀ group or Z group.

Ｑ_Ａ０及びＱ_Ａを、表２７〜表２８に例示する。 Q _A0 and Q _A are exemplified in Table 27 to Table 28.

Ｔ_Ａ０及びＴ_Ａを、表２９に例示する。

T _A0 and T _A are illustrated in Table 29.

化合物（II）として、例えば、βが式（II-1）、式（II-7）又は式（II-8）で示される基の場合があげられ、具体的には、式（II''）

［式中、α''は、芳香族５員環を表し、Ｘ_αは、前記と同一の意味を表し、ｘは、メチン基、酸素原子、硫黄原子、−Ｎ＝基又は１個のメチル基で置換されてもよいイミノ基を表し、β''は、
式（II''-1）

（式中、Ｔ_α、Ｋ_α及びＬ_αは、前記と同一の意味を表す。）
で示される基、
式（II''-7）

（式中、Ｔ_αは、前記と同一の意味を表す。）
で示される基、又は、
式（II''-8）

（式中、Ｌ_γは、前記と同一の意味を表す。）
で示される基を表す。］
で示されるシンナモイル化合物があげられる。シンナモイル化合物（II''）において、ｘがメチン基の場合、ｘは置換基を有さない。
更に具体的には、シンナモイル化合物（II''）において、α''がチオフェン環の場合があげられる。
より具体的には、シンナモイル化合物（II''）において、α''がチオフェン環であり、β''が基（II''-1）であって、Ｔ_αがメチル基であって、Ｋ_αが、水素原子であって、Ｌ_αが、メチル基である場合があげられる。
また具体的には、シンナモイル化合物（II''）において、α''がチオフェン環であり、β''が基（II''-7）であって、Ｔ_αがメチル基である場合があげられる。
一層具体的には、シンナモイル化合物（II''）において、α''がチオフェン環であり、β''が基（II''-8）であって、Ｌ_γがメチル基である場合があげられる。 Examples of the compound (II) include a case where β is a group represented by the formula (II-1), the formula (II-7) or the formula (II-8). )

[Wherein _{α ″} represents an aromatic 5-membered ring, X _α represents the same meaning as described above, and x represents a methine group, an oxygen atom, a sulfur atom, —N = group or one methyl group. Represents an imino group which may be substituted with a group, β ''
Formula (II ''-1)

(In the formula, T _α , K _α and L _α represent the same meaning as described above.)
A group represented by
Formula (II ''-7)

(In the formula, T _α represents the same meaning as described above.)
Or a group represented by
Formula (II ''-8)

(Wherein L _γ represents the same meaning as described above.)
Represents a group represented by ]
The cinnamoyl compound shown by these is mention | raise | lifted. In the cinnamoyl compound (II ″), when x is a methine group, x has no substituent.
More specifically, in the cinnamoyl compound (II ″), α ″ is a thiophene ring.
More specifically, in the cinnamoyl compound (II ″), α ″ is a thiophene ring, β ″ is a group (II ″ -1), T _α is a methyl group, and K _Examples include a case where _α is a hydrogen atom and L _α is a methyl group.
More specifically, in the cinnamoyl compound (II ″), α ″ is a thiophene ring, β ″ is a group (II ″ -7), and T _α is a methyl group. It is done.
More specifically, in the cinnamoyl compound (II ″), α ″ is a thiophene ring, β ″ is a group (II ″ -8), and L _γ is a methyl group. It is done.

化合物（III）として、例えば、Ｂ０が式（III-1）、式（III-7）又は式（III-8）で示される基の場合があげられ、具体的には、式（III’）

［式中、Ａ０'は、芳香族５員環を表し、Ｘ_ＡＯ及びｘは、前記と同一の意味を表し、Ｂ０'は、式（III'-1）

（式中、Ｔ_ＡＯ、Ｋ_ＡＯ及びＬ_ＡＯは、前記と同一の意味を表す。）
で示される基、
式（III'-7）

（式中、Ｔ_ＡＯは、前記と同一の意味を表す。）
で示される基、又は、
式（III'-8）

（式中、Ｌ_Ｃ０は、前記と同一の意味を表す。）
で示される基を表す。］
で示されるシンナモイル化合物があげられる。シンナモイル化合物（III’）において、ｘがメチン基の場合、ｘは置換基を有さない。
更に具体的には、シンナモイル化合物（III’）において、Ａ０'がチオフェン環の場合があげられる。
より具体的には、シンナモイル化合物（III'）において、Ａ０'がチオフェン環であり、Ｂ０'が基（III'-1）であって、Ｔ_ＡＯがメチル基であって、Ｋ_ＡＯが、水素原子であって、Ｌ_ＡＯが、メチル基である場合があげられる。
また具体的には、シンナモイル化合物（III'）において、Ａ０'がチオフェン環であり、Ｂ０'が基（III'-7）であって、Ｔ_ＡＯがメチル基である場合があげられる。
一層具体的には、シンナモイル化合物（III'）において、α''がチオフェン環であり、β''が基（III'-8）であって、Ｌ_ＣＯがメチル基である場合があげられる。 Examples of the compound (III) include a case where B0 is a group represented by the formula (III-1), the formula (III-7) or the formula (III-8), specifically, the formula (III ′)

[Wherein, A0 ′ represents an aromatic 5-membered ring, X _AO and x represent the same meaning as described above, and B0 ′ represents the formula (III′-1)

(In the formula, T _AO , K _AO and L _AO represent the same meaning as described above.)
A group represented by
Formula (III'-7)

(In the formula, T _AO represents the same meaning as described above.)
Or a group represented by
Formula (III'-8)

(Wherein L _C0 represents the same meaning as described above.)
Represents a group represented by ]
The cinnamoyl compound shown by these is mention | raise | lifted. In the cinnamoyl compound (III ′), when x is a methine group, x has no substituent.
More specifically, in the cinnamoyl compound (III ′), A0 ′ is a thiophene ring.
More specifically, in the cinnamoyl compound (III ′), A0 ′ is a thiophene ring, B0 ′ is a group (III′-1), T _AO is a methyl group, and K _AO is hydrogen. An example is an atom in which L _AO is a methyl group.
Further Specifically, 'in, A0 cinnamoyl compound (III)' is a thiophene ring, B0 'is a group (III'-7), if T _AO is a methyl group.
More specifically, in the cinnamoyl compound (III ′), α ″ is a thiophene ring, β ″ is a group (III′-8), and L _{2 CO} is a methyl group.

化合物（IV）として、例えば、Ｂが式（IV-1）、式（IV-7）又は式（IV-8）で示される基の場合があげられ、具体的には、式（IV’）

［式中、Ａ’は、芳香族５員環を表し、Ｘ_Ａ及びｘは、前記と同一の意味を表し、Ｂ’は、式（IV'-1）

（式中、Ｔ_Ａ、Ｋ_Ａ及びＬ_Ａは、前記と同一の意味を表す。）
で示される基、
式（IV'-7）

（式中、Ｔ_Ａは、前記と同一の意味を表す。）
で示される基、又は、
式（IV'-8）

（式中、Ｌ_Ｃは、前記と同一の意味を表す。）
で示される基を表す。］
で示されるシンナモイル化合物があげられる。シンナモイル化合物（IV’）において、ｘがメチン基の場合、ｘは置換基を有さない。
更に具体的には、シンナモイル化合物（IV’）において、Ａ’がチオフェン環である場合があげられる。
より具体的には、シンナモイル化合物（IV'）において、Ａ’がチオフェン環であり、Ｂ’が基（IV'-1）であって、Ｔ_Ａがメチル基であって、Ｋ_Ａが、水素原子であって、Ｌ_Ａが、メチル基である場合があげられる。
また具体的には、シンナモイル化合物（IV'）において、Ａ’がチオフェン環であり、Ｂ'が基（IV'-7）であって、Ｔ_Ａがメチル基である場合があげられる。
一層具体的には、シンナモイル化合物（IV'）において、Ａ’がチオフェン環であり、Ｂ'が基（III'-8）であって、Ｌ_Ｃがメチル基である場合があげられる。 Examples of the compound (IV) include a case where B is a group represented by the formula (IV-1), formula (IV-7) or formula (IV-8), specifically, the formula (IV ′)

[Wherein, A ′ represents an aromatic 5-membered ring, X _A and x represent the same meaning as described above, and B ′ represents the formula (IV′-1)

(In the formula, T _A , K _A and L _A represent the same meaning as described above.)
A group represented by
Formula (IV'-7)

(Wherein, _{T A} represents the same meaning as above.)
Or a group represented by
Formula (IV'-8)

(Wherein L _C represents the same meaning as described above.)
Represents a group represented by ]
The cinnamoyl compound shown by these is mention | raise | lifted. In the cinnamoyl compound (IV ′), when x is a methine group, x has no substituent.
More specifically, in the cinnamoyl compound (IV ′), A ′ is a thiophene ring.
More specifically, 'in, A cinnamoyl compound (IV)' is a thiophene ring, B 'is a group (IV'-1), T _A is a methyl group, K _A is hydrogen an atomic, L _a may be mentioned be a methyl group.
More specifically, in the cinnamoyl compound (IV ′), A ′ is a thiophene ring, B ′ is a group (IV′-7), and T _A is a methyl group.
In more specifically, 'in, A cinnamoyl compound (IV)' is a thiophene ring, B 'is a group (III'-8), if L _C is a methyl group.

化合物（V）として、例えば、ｂが式（V-1）、式（V-7）又は式（V-8）で示される基の場合があげられ、具体的には、式（V''）

［式中、ａ''は、チオフェン環、フラン環、ピロール環又はチアゾール環を表し、Ｘ_ａ及びｘは、前記と同一の意味を表し、ｂ''は、式（V''-1）

（式中、Ｔ_ａ、Ｋ_ａ及びＬ_ａは、前記と同一の意味を表す。）
で示される基、
式（V''-7）

（式中、Ｔ_ａは、前記と同一の意味を表す。）
で示される基、又は、
式（V''-8）

（式中、Ｌ_ｃは、前記と同一の意味を表す。）
で示される基を表す。］
で示されるシンナモイル化合物があげられる。
更に具体的には、シンナモイル化合物（V''）において、ａ''がチオフェン環である場合があげられる。
より具体的には、シンナモイル化合物（V''）において、ａ''がチオフェン環であり、ｂ''が基（V''-1）であって、Ｔ_ａがメチル基であって、Ｋ_ａが、水素原子であって、Ｌ_ａが、メチル基である場合があげられる。
また具体的には、シンナモイル化合物（V''）において、ａ''がチオフェン環であり、ｂ''が基（V''-7）であって、Ｔ_ａがメチル基である場合があげられる。
一層具体的には、シンナモイル化合物（V''）において、ａ''がチオフェン環であり、ｂ''が基（V''-8）であって、Ｌ_ｃがメチル基である場合があげられる。
Examples of the compound (V) include the case where b is a group represented by the formula (V-1), the formula (V-7) or the formula (V-8). )

[Wherein _{a ″} represents a thiophene ring, a furan ring, a pyrrole ring or a thiazole ring, X _a and x represent the same meaning as described above, and b ″ represents a formula (V ″ -1)

(In the formula, T _a , K _a and L _a represent the same meaning as described above.)
A group represented by
Formula (V ''-7)

(Wherein, _{T a} represents the same meaning as above.)
Or a group represented by
Formula (V ''-8)

(Wherein L _c represents the same meaning as described above.)
Represents a group represented by ]
The cinnamoyl compound shown by these is mention | raise | lifted.
More specifically, in the cinnamoyl compound (V ″), a ″ is a thiophene ring.
More specifically, in the cinnamoyl compound (V ″), a ″ is a thiophene ring, b ″ is a group (V ″ -1), _Ta is a methyl group, and K _{A case where a} is a hydrogen atom and L _a is a methyl group can be mentioned.
More specifically, in the cinnamoyl compound (V ″), a ″ is a thiophene ring, b ″ is a group (V ″ -7), and _Ta is a methyl group. It is done.
More specifically, in the cinnamoyl compound (V ″), a ″ is a thiophene ring, b ″ is a group (V ″ -8), and L _c is a methyl group. It is done.

化合物（VI）として、例えば、ａ１がチオフェン環であり、ｂ１が基（VI-1）であって、ｒ_ｂ１がメチル基であって、Ｋ_ａ１が水素原子であって、Ｌ_ａ１がメチル基である場合、ａ１がチオフェン環であり、ｂ１が基（VI-7）であって、ｒ_ｂ１がメチル基である場合、又は、ａ１がチオフェン環であり、ｂ１が基（VI-8）であって、ｒ_ｂ１がメチル基である場合があげられる。 As the compound (VI), for example, a1 is a thiophene ring, b1 is a group (VI-1), _rb1 is a methyl group, _Ka1 is a hydrogen atom, and _La1 is a methyl group. A1 is a thiophene ring, b1 is a group (VI-7) and _rb1 is a methyl group, or a1 is a thiophene ring and b1 is a group (VI-8). In this case, _rb1 is a methyl group.

ＷＯ９７／３５５６５号公報、ＪＰ０９２２７５４７号公報、ＷＯ００／２０３７１号公報、ＪＰ２００２３７１０７８号公報、ＷＯ０１／７９１８７号公報及びＷＯ９２／１８４８３号公報にある種の概念的な骨格を有する化合物が開示されているが、当該文献には組織内における細胞外マトリックス遺伝子の転写抑制の効果、ひいては細胞外マトリックス蓄積量抑制の効果についての記載は無い。 WO97 / 35565, JP09227547, WO00 / 20371, JP20022371078, WO01 / 79187 and WO92 / 18483 disclose compounds having a certain conceptual skeleton. There is no description in the literature about the effect of suppressing transcription of extracellular matrix genes in tissues, and hence the effect of suppressing the amount of extracellular matrix accumulation.

化合物（I）又は（II）は、例えば、式（α）（式中、α、Ｘ_α、Ｙ_α、ｐ及びｑは前記と同一の意味を表す。）で示される化合物と、式（β）（式中、βは前記と同一の意味を表す。）で示される化合物とを反応させる（ＲｕｓｓｉａｎＪ．ＧｅｎｅｒａｌＣｈｅｍ.（２００１），７１，１２５７、ＩｎｄｉａｎＪ．Ｃｈｅｍ.（１９７４），１２，９５６及びＪＰ５００４６６６６号公報参照）ことにより製造することができる。

化合物（III）は、例えば、式（AO）（式中、Ａ、Ｘ_Ａ０、Ｙ_Ａ０、ｐ及びｑは前記と同一の意味を表す。）で示される化合物と、式（BO）（式中、Ｂ０は前記と同一の意味を表す。）で示される化合物とを、上記と同様に反応させることにより製造することができる。

化合物（IV）は、例えば、式（A）（式中、Ａ、Ｘ_Ａ、Ｙ_Ａ、ｐ及びｑは前記と同一の意味を表す。）で示される化合物と、式（B）（式中、Ｂは前記と同一の意味を表す。）で示される化合物とを、上記と同様に反応させることにより製造することができる。

化合物（V）は、例えば、式（ａ）（式中、a、Ｘ_ａ、Ｙ_ａ、ｐ及びｑは前記と同一の意味を表す。）で示される化合物と、式（ｂ）（式中、ｂは前記と同一の意味を表す。）で示される化合物とを、上記と同様に反応させることにより製造することができる。

化合物（VI）は、例えば、式（ａ１）（式中、ａ１及びＸ_ａ1は前記と同一の意味を表す。）で示される化合物と、式（ｂ１）（式中、ｂ１は前記と同一の意味を表す。）で示される化合物とを、上記と同様に反応させることにより製造することができる。

Compound (I) or (II) includes, for example, a compound represented by the formula (α) (wherein α, X _α , Y _α , p and q represent the same meanings as described above) and a formula (β ) (Wherein β represents the same meaning as described above) (Russian J. General Chem. (2001), 71, 1257, Indian J. Chem. (1974), 12, 956 and JP50046666).

Compound (III) includes, for example, a compound represented by formula (AO) (wherein A, X _A0 , Y _A0 , p and q represent the same meaning as described above), and formula (BO) (wherein , B0 represents the same meaning as described above) and can be produced by reacting in the same manner as described above.

Compound (IV) includes, for example, a compound represented by formula (A) (wherein A, X _A , Y _A , p and q represent the same meaning as described above), and formula (B) (wherein , B represents the same meaning as described above) and can be produced by reacting in the same manner as described above.

Compound (V) includes, for example, a compound represented by formula (a) (wherein a, X _a , Y _a , p and q represent the same meaning as described above), and formula (b) (wherein , B represents the same meaning as described above.) And can be produced by reacting in the same manner as described above.

Compound (VI) includes, for example, a compound represented by formula (a1) (wherein a1 and _Xa1 represent the same meaning as described above), and formula (b1) (wherein b1 is the same as defined above). Can be produced by reacting the compound represented by the above) in the same manner as described above.

式（ａ１）で示される化合物の一部は公知物質であるが、前記の式（VII）で示されるアルデヒド誘導体（以下、本発明アルデヒド誘導体と記すこともある。）は、これまで報告された例はなく新規物質である。 Some of the compounds represented by the formula (a1) are known substances, but the aldehyde derivatives represented by the above formula (VII) (hereinafter sometimes referred to as the aldehyde derivatives of the present invention) have been reported so far. There is no example and it is a new substance.

本発明アルデヒド誘導体のうち、式（VII-1）

［式中、Ｗ_ｂは、酸素原子、硫黄原子又は−ＮＭｅ−基を表し、ｒ_５は、水酸基、C1-C10アルコキシ基又はｒｒ’Ｎ−基（ｒ及びｒ’は、前記と同一の意味を表す。）を表し、Ｗ_ｃは、−ＣＯ−基又は−ＣＨ_２−基を表し、ｒ_６は、水素原子又はC1-C10アルキル基を表す。但し、Ｗ_ｃが−ＣＨ_２−基のとき、ｒ及びｒ’は水素原子となることはない。］
で示される化合物は、例えば、式（VII-2）

［式中、Ｗ_ｂは、前記と同一の意味を表す。］
で示される化合物を、式（VII-3）

［式中、ｒ_５、Ｗ_ｃ及びｒ_６は、前記と同一の意味を表す。］
で示される化合物と反応させることで製造することができる。当該反応において、反応温度の範囲は、通常，室温〜溶媒還流温度であり、反応時間の範囲は、通常，瞬時〜約２４時間である。当該反応は、通常、脱水剤の存在下で行うが、用いられる脱水剤としては、カルボニルジイミダゾール等があげられる。当該反応に供せられる試剤の量は、化合物（VII-2）１モルに対して、化合物（VII-3）は通常１〜２モル、脱水剤は通常１〜７モルである。上記反応において、溶媒は必ずしも必要ではないが、通常は溶媒の存在下に行われる。当該反応に使用しうる溶媒としては、ヘキサン、石油エーテル等の脂肪族炭化水素類、ベンゼン、トルエン等の芳香族炭化水素類、クロロホルム、ジクロロエタン等のハロゲン化炭化水素類、ジエチルエーテル、ジオキサン、テトラヒドロフラン等のエーテル類、アセトン、メチルエチルケトン等のケトン類、酢酸エチル、炭酸ジエチル等のエステル類、アセトニトリル、イソブチルニトリル等のニトリル類、ホルムアミド、Ｎ，Ｎ−ジメチルホルムアミド等のアミド類、ジメチルスルホキシド等の硫黄化合物類等又はそれらの混合物があげられる。反応終了後の反応液は、有機溶媒抽出、水洗後、有機層を減圧濃縮する等の通常の後処理を行い、必要に応じ、クロマトグラフィー、再結晶等の操作によって精製することにより、本発明ベンズアルデヒド誘導体を得ることができる。化合物（VII-2）は、例えば、Ｔｅｔｒａｈｅｄｒｏｎ（１９８５）４１，３８０３等の文献に記載されており公知である。化合物（VII-3）としては、例えば、２−メトキシエチルアミン、２−アミノエタノール、Ｎ−（２−メトキシエチル）メチルアミン、２−（メチルアミノ）エタノール、グリシン、グリシンメチルエステル、グリシンアミド及びＮ,Ｎ−ジメチルエチレンジアミン等が挙げられる。
具体的には、化合物（VII-2）と、化合物（VII-3）として、２−メトキシエチルアミン、２−アミノエタノール、Ｎ−（２−メトキシエチル）メチルアミン又はグリシンアミドを反応させることで、（VII-1）を製造することがあげられる。 Among the aldehyde derivatives of the present invention, the formula (VII-1)

[Wherein, W _b represents an oxygen atom, a sulfur atom or a —NMe— group, r ₅ represents a hydroxyl group, a C 1 -C 10 alkoxy group or an rr′N— group (where r and r ′ have the same meanings as described above). represents represents) a, _{W c} is -CO- group or a -CH ₂ -. a group, _{r 6} represents a hydrogen atom or a C1-C10 alkyl group. However, when W _c is a —CH ₂ — group, r and r ′ do not become a hydrogen atom. ]
The compound represented by the formula is, for example, the formula (VII-2)

[Wherein W _b represents the same meaning as described above. ]
A compound represented by the formula (VII-3)

[Wherein, r ₅ , W _c and r ₆ represent the same meaning as described above. ]
It can manufacture by making it react with the compound shown by these. In the reaction, the reaction temperature range is usually from room temperature to the solvent reflux temperature, and the reaction time range is usually from instantaneous to about 24 hours. The reaction is usually carried out in the presence of a dehydrating agent, and examples of the dehydrating agent used include carbonyldiimidazole. The amount of the reagent used for the reaction is usually 1 to 2 mol for compound (VII-3) and 1 to 7 mol for dehydrating agent, relative to 1 mol of compound (VII-2). In the above reaction, a solvent is not always necessary, but it is usually performed in the presence of a solvent. Solvents that can be used for the reaction include aliphatic hydrocarbons such as hexane and petroleum ether, aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as chloroform and dichloroethane, diethyl ether, dioxane, and tetrahydrofuran. Ethers such as acetone and methyl ethyl ketone, esters such as ethyl acetate and diethyl carbonate, nitriles such as acetonitrile and isobutyl nitrile, amides such as formamide and N, N-dimethylformamide, sulfur such as dimethyl sulfoxide Examples thereof include compounds and the like or mixtures thereof. The reaction solution after completion of the reaction is subjected to usual post-treatment such as organic solvent extraction, washing with water, and concentration of the organic layer under reduced pressure, etc., and if necessary, it is purified by operations such as chromatography, recrystallization, etc. A benzaldehyde derivative can be obtained. Compound (VII-2) is known in the literature such as Tetrahedron (1985) 41, 3803. Examples of the compound (VII-3) include 2-methoxyethylamine, 2-aminoethanol, N- (2-methoxyethyl) methylamine, 2- (methylamino) ethanol, glycine, glycine methyl ester, glycinamide and N , N-dimethylethylenediamine and the like.
Specifically, by reacting compound (VII-2) with 2-methoxyethylamine, 2-aminoethanol, N- (2-methoxyethyl) methylamine or glycinamide as compound (VII-3), (VII-1) can be produced.

また、本発明アルデヒド誘導体のうち、式（VII'-1）

［式中、Ｗ_ｄは、酸素原子又は硫黄原子を表し、Ｗ_ｃは前記と同一の意味を表し、ｒ_７は、水酸基又はC1-C10アルコキシ基を表す。］
で示される化合物は、例えば、式（VII'-2）

［式中、ｒ_ｘはハロゲン原子を表す。］
で示される化合物を、式（VII'-3）

［式中、ｒ_７、Ｗ_ｃ及びＷ_ｄは、前記と同一の意味を表す。］
で示される化合物と反応させることで製造することができる。当該反応において、反応温度の範囲は、通常，室温〜溶媒還流温度であり、反応時間の範囲は、通常，瞬時〜約２４時間である。当該反応は、通常、塩基の存在下で行うが、用いられる塩基としては、水素化ナトリウム、水酸化カリウム、炭酸カリウム、ノルマルブチルリチウム等があげられる。当該反応に供せられる試剤の量は、化合物（VII'-2）１モルに対して、化合物（VII'-3）は通常１〜２モル、塩基は通常１〜７モルである。上記反応において、溶媒は必ずしも必要ではないが、通常は溶媒の存在下に行われる。当該反応に使用しうる溶媒としては、ジエチルエーテル、ジオキサン、テトラヒドロフラン等のエーテル類、アセトン、メチルエチルケトン等のケトン類、酢酸エチル、炭酸ジエチル等のエステル類、アセトニトリル、イソブチルニトリル等のニトリル類、ホルムアミド、Ｎ，Ｎ−ジメチルホルムアミド等のアミド類、ジメチルスルホキシド等の硫黄化合物類等又はそれらの混合物があげられる。反応終了後、前記と同様にして、本発明ベンズアルデヒド誘導体を得ることができる。化合物（VII'-2）は、例えば、ＷＯ００／３２５９８号公報等の文献に記載されており公知である。化合物（VII'-3）としては、例えば、エチレングリコール、２−メトキシエタノール、グリコール酸メチル、チオグリコール酸メチル等が挙げられる。
具体的には、化合物（VII'-2）と、化合物（VII'-3）として、エチレングリコール又はチオグリコール酸メチルを反応させることで、（VII'-1）を製造することがあげられる。 Among the aldehyde derivatives of the present invention, the formula (VII′-1)

[Wherein, W _d represents an oxygen atom or a sulfur atom, W _c represents the same meaning as described above, and r ₇ represents a hydroxyl group or a C1-C10 alkoxy group. ]
The compound represented by the formula is, for example, the formula (VII′-2)

[Wherein r _x represents a halogen atom. ]
A compound represented by the formula (VII'-3)

[Wherein, r ₇ , W _c and W _d represent the same meaning as described above. ]
It can manufacture by making it react with the compound shown by these. In the reaction, the reaction temperature range is usually from room temperature to the solvent reflux temperature, and the reaction time range is usually from instantaneous to about 24 hours. The reaction is usually performed in the presence of a base. Examples of the base used include sodium hydride, potassium hydroxide, potassium carbonate, and normal butyl lithium. The amount of the reagent used for the reaction is usually 1 to 2 mol for compound (VII′-3) and 1 to 7 mol for base, relative to 1 mol of compound (VII′-2). In the above reaction, a solvent is not always necessary, but it is usually performed in the presence of a solvent. Solvents that can be used in the reaction include ethers such as diethyl ether, dioxane and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, esters such as ethyl acetate and diethyl carbonate, nitriles such as acetonitrile and isobutyl nitrile, formamide, Examples thereof include amides such as N, N-dimethylformamide, sulfur compounds such as dimethyl sulfoxide, and the like, or a mixture thereof. After completion of the reaction, the benzaldehyde derivative of the present invention can be obtained in the same manner as described above. Compound (VII′-2) is publicly known, for example, described in documents such as WO00 / 32598. Examples of the compound (VII′-3) include ethylene glycol, 2-methoxyethanol, methyl glycolate, methyl thioglycolate and the like.
Specifically, (VII'-1) can be produced by reacting compound (VII'-2) with ethylene glycol or methyl thioglycolate as compound (VII'-3).

また、本発明アルデヒド誘導体のうち、式（VII''-1）

［式中、ｒ_８は、C1-C10アルコキシ基で置換されたC1-C10アルキル基又はC1-C10アルコキシ基で置換されたC2-C10アルコキシ基を表す。］
で示される化合物は、例えば、式（VII''-2）

［式中、ｒ_ｘは前記と同一の意味を表す。］
で示される化合物を、式（VII'-3）

［式中、ｒ_８は、前記と同一の意味を表す。］
で示される化合物と反応させることで製造することができる。当該反応において、反応温度の範囲は、通常，室温〜溶媒還流温度であり、反応時間の範囲は、通常，瞬時〜約２４時間である。当該反応は、通常、塩基及び銅触媒の存在下で行うが、用いられる塩基としては、水素化ナトリウム、水酸化カリウム、炭酸カリウム等があげられ、銅触媒としては、銅（粉末）、臭化銅（Ｉ）、よう化銅（Ｉ）があげられる。Ｎ，Ｎ’−ジメチルエチレンジアミンなどの脂肪族アミンを加えることで、収率よく製造することができる。当該反応に供せられる試剤の量は、化合物（VII''-2）１モルに対して、化合物（VII''-3）は通常１〜２モル、塩基は通常１〜７モルであり、銅触媒は通常０．１〜２モルである。上記反応において、溶媒は必ずしも必要ではないが、通常は溶媒の存在下に行われる。当該反応に使用しうる溶媒としては、ジエチルエーテル、ジオキサン、テトラヒドロフラン等のエーテル類、アセトン、メチルエチルケトン等のケトン類、酢酸エチル、炭酸ジエチル等のエステル類、アセトニトリル、イソブチルニトリル等のニトリル類、ホルムアミド、Ｎ，Ｎ−ジメチルホルムアミド等のアミド類、ジメチルスルホキシド等の硫黄化合物類等又はそれらの混合物があげられる。反応終了後、前記と同様にして、本発明ベンズアルデヒド誘導体を得ることができる。化合物（VII''-3）は、例えば、ＵＳ３４４９４０６号公報等の文献に記載されており公知である。化合物（VII'-3）としては、例えば、メトキシアセトアミド、カルバミン酸２−メトキシエチル等が挙げられる。 Among the aldehyde derivatives of the present invention, the formula (VII ″ -1)

[Wherein r ₈ represents a C1-C10 alkyl group substituted with a C1-C10 alkoxy group or a C2-C10 alkoxy group substituted with a C1-C10 alkoxy group. ]
The compound represented by the formula is, for example, formula (VII ″ -2)

[Wherein r _x represents the same meaning as described above. ]
A compound represented by the formula (VII'-3)

[Wherein r ₈ represents the same meaning as described above. ]
It can manufacture by making it react with the compound shown by these. In the reaction, the reaction temperature range is usually from room temperature to the solvent reflux temperature, and the reaction time range is usually from instantaneous to about 24 hours. The reaction is usually carried out in the presence of a base and a copper catalyst. Examples of the base used include sodium hydride, potassium hydroxide, potassium carbonate and the like, and examples of the copper catalyst include copper (powder), bromide. Examples include copper (I) and copper (I) iodide. By adding an aliphatic amine such as N, N′-dimethylethylenediamine, it can be produced with good yield. The amount of the reagent used for the reaction is usually 1 to 2 mol for compound (VII ″ -3) and 1 to 7 mol for base, relative to 1 mol for compound (VII ″ -2). A copper catalyst is 0.1-2 mol normally. In the above reaction, a solvent is not always necessary, but it is usually performed in the presence of a solvent. Solvents that can be used in the reaction include ethers such as diethyl ether, dioxane and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, esters such as ethyl acetate and diethyl carbonate, nitriles such as acetonitrile and isobutyl nitrile, formamide, Examples thereof include amides such as N, N-dimethylformamide, sulfur compounds such as dimethyl sulfoxide, and the like, or a mixture thereof. After completion of the reaction, the benzaldehyde derivative of the present invention can be obtained in the same manner as described above. Compound (VII ″ -3) is known and described in documents such as US Pat. No. 3,449,406. Examples of compound (VII′-3) include methoxyacetamide, 2-methoxyethyl carbamate and the like.

また、本発明アルデヒド誘導体のうち、式（VII'''-1）

［式中、Ｗ_ｅは、メチン基又は−Ｎ＝基を表し、ｒ_８は、前記と同一の意味を表す。］
で示される化合物は、例えば、式（VII'''-2）

［式中、Ｗ_ｅは前記と同一の意味を表す。］
で示される化合物を、式（VII''-3）

［式中、ｒ_ｘは、前記と同一の意味を表す。］
で示される化合物と反応させることで製造することができる。当該反応において、反応温度の範囲は、通常，室温〜溶媒還流温度であり、反応時間の範囲は、通常，瞬時〜約２４時間である。当該反応は、通常、塩基の存在下で行うが、用いられる塩基としては、水酸化カリウム、炭酸カリウム等の無機塩基、ピリジン、トリエチルアミン、Ｎ，Ｎ−ジエチルアニリン等の有機塩基があげられる。当該反応に供せられる試剤の量は、化合物（VII'''-2）１モルに対して、化合物（VII'''-3）は通常１〜２モル、塩基は通常１〜７モルである。上記反応において、溶媒は必ずしも必要ではないが、通常は溶媒の存在下に行われる。当該反応に使用しうる溶媒としては、ジエチルエーテル、ジオキサン、テトラヒドロフラン等のエーテル類、アセトン、メチルエチルケトン等のケトン類、酢酸エチル、炭酸ジエチル等のエステル類、アセトニトリル、イソブチルニトリル等のニトリル類、ホルムアミド、Ｎ，Ｎ−ジメチルホルムアミド等のアミド類、ジメチルスルホキシド等の硫黄化合物類等又はそれらの混合物があげられる。反応終了後、前記と同様にして、本発明ベンズアルデヒド誘導体を得ることができる。化合物（VII'''-2）は、例えば、Ｂｉｏｏｒｇ．Ｍｅｄ．Ｃｈｅｍ．Ｌｅｔｔ．１４（１），２３５（２００４）等の文献に記載されており公知である。化合物（VII'''-3）としては、例えば、メトキシアセチルクロリド、クロロぎ酸２−メトキシエチル等が挙げられる。 Among the aldehyde derivatives of the present invention, the formula (VII '''-1)

[Wherein W _e represents a methine group or —N═ group, and r ₈ represents the same meaning as described above. ]
For example, the compound represented by the formula (VII '''-2)

[Wherein W _e represents the same meaning as described above. ]
A compound of formula (VII ''-3)

[Wherein r _x represents the same meaning as described above. ]
It can manufacture by making it react with the compound shown by these. In the reaction, the reaction temperature range is usually from room temperature to the solvent reflux temperature, and the reaction time range is usually from instantaneous to about 24 hours. The reaction is usually performed in the presence of a base. Examples of the base used include inorganic bases such as potassium hydroxide and potassium carbonate, and organic bases such as pyridine, triethylamine, and N, N-diethylaniline. The amount of the reagent used for the reaction is usually 1 to 2 moles for compound (VII '''-3) and 1 to 7 moles for base relative to 1 mole of compound (VII'''-2). is there. In the above reaction, a solvent is not always necessary, but it is usually performed in the presence of a solvent. Solvents that can be used in the reaction include ethers such as diethyl ether, dioxane and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, esters such as ethyl acetate and diethyl carbonate, nitriles such as acetonitrile and isobutyl nitrile, formamide, Examples thereof include amides such as N, N-dimethylformamide, sulfur compounds such as dimethyl sulfoxide, and the like, or a mixture thereof. After completion of the reaction, the benzaldehyde derivative of the present invention can be obtained in the same manner as described above. Compound (VII ′ ″-2) is described in, for example, Bioorg. Med. Chem. Lett. 14 (1), 235 (2004) and the like, which are publicly known. Examples of the compound (VII ′ ″-3) include methoxyacetyl chloride, 2-methoxyethyl chloroformate and the like.

本発明アルデヒド誘導体と、前記の化合物（VIII'）とを反応させることにより、前記の化合物（VIII''）を製造することができる。 The compound (VIII ″) can be produced by reacting the aldehyde derivative of the present invention with the compound (VIII ′).

表３０〜表３１に、化合物番号（ａ）〜（ｐ）で表される新規な本発明アルデヒド誘導体（VII-1）を例示する。 Tables 30 to 31 exemplify novel aldehyde derivatives (VII-1) of the present invention represented by compound numbers (a) to (p).

表３２に、化合物番号（ｑ）〜（ｒ）で表される新規な本発明アルデヒド誘導体（VII'-1）を例示する。 Table 32 exemplifies the novel aldehyde derivative (VII′-1) of the present invention represented by compound numbers (q) to (r).

表３３〜表３４に、化合物番号（ｓ）〜（ｖ）で表される新規な本発明アルデヒド誘導体（VII''-1）を例示する。 Tables 33 to 34 exemplify novel aldehyde derivatives (VII ″ -1) of the present invention represented by compound numbers (s) to (v).

表３５に、化合物番号（ｗ）で表される新規な本発明アルデヒド誘導体（VII'''-1）を例示する。 Table 35 illustrates a novel aldehyde derivative (VII ′ ″-1) of the present invention represented by the compound number (w).

化合物(V)のうち、化合物番号（１ａ-1）〜（７２ａ-1）で表される化合物(Va-1)、化合物番号（１ａ-2）〜（１６ａ-2）で表される化合物(Va-2)及び化合物番号（１ａ-3）〜（１１ａ-3）で表される化合物(Va-3)を、表３６〜表４３に例示する。
（表３６〜表４３）
本発明化合物(Va-1)、(Va-2)及び(Va-3)

Among the compounds (V), compounds (Va-1) represented by compound numbers (1a-1) to (72a-1), compounds represented by compound numbers (1a-2) to (16a-2) ( The compounds (Va-3) represented by Va-2) and compound numbers (1a-3) to (11a-3) are exemplified in Tables 36 to 43.
(Table 36 to Table 43)
Compounds of the present invention (Va-1), (Va-2) and (Va-3)

化合物(V)のうち、化合物番号（１ａ’）〜（３０ａ’）で表される化合物(Va’)を、表４４〜４５に例示する。
（表４４〜４５）
化合物(Va’)

Of compounds (V), compounds (Va ′) represented by compound numbers (1a ′) to (30a ′) are exemplified in Tables 44 to 45.
(Tables 44-45)
Compound (Va ')

化合物(V)のうち、化合物番号（１ｂ）〜（１３ｂ）で表される化合物(Vb)を、表４６に例示する。
（表４６）
化合物(Vb)

Of the compounds (V), compounds (Vb) represented by compound numbers (1b) to (13b) are exemplified in Table 46.
(Table 46)
Compound (Vb)

化合物(V)のうち、化合物番号（１ｃ）〜（１１ｃ）で表される化合物(Vc)を、表４７に例示する。
（表４７）
化合物(Vc)

Of the compounds (V), compounds (Vc) represented by compound numbers (1c) to (11c) are exemplified in Table 47.
(Table 47)
Compound (Vc)

化合物(V)のうち、化合物番号（１ｄ）〜（３ｄ）で表される化合物(Vd)を、表４８に例示する。
（表４８）
化合物(Vd)

Among the compounds (V), compounds (Vd) represented by compound numbers (1d) to (3d) are exemplified in Table 48.
(Table 48)
Compound (Vd)

化合物(V)のうち、化合物番号（１e）〜（７０e）で表される化合物（Ve）を、表４９〜表５１に例示する。
（表４９〜表５１）
本発明化合物（Ve）

Of compound (V), compounds (Ve) represented by compound numbers (1e) to (70e) are exemplified in Table 49 to Table 51.
(Table 49 to Table 51)
Compound of the present invention (Ve)

化合物（V）のうち、化合物番号（１ｆ）〜（７０ｆ）で表される化合物（Vｆ）を、表５２〜５４に例示する。
（表５２〜５４）
本発明化合物（Vｆ）

Of compounds (V), compounds (Vf) represented by compound numbers (1f) to (70f) are exemplified in Tables 52 to 54.
(Tables 52-54)
Compound of the present invention (Vf)

化合物（V）のうち、化合物番号（１ｇ）〜（７０ｇ）で表される化合物（Vｇ）を、表５５〜５７に例示する。
（表５５〜５７）
本発明化合物（Vｇ）

Of compound (V), compounds (Vg) represented by compound numbers (1 g) to (70 g) are exemplified in Tables 55 to 57.
(Tables 55-57)
Compound of the present invention (Vg)

化合物（V）のうち、化合物番号（１ｈ）〜（１６ｈ）で表される化合物（Vｈ）を、表５８〜表５９に例示する。
（表５８〜表５９）
化合物（Vｈ）

Of compound (V), compounds (Vh) represented by compound numbers (1h) to (16h) are exemplified in Tables 58 to 59.
(Table 58 to Table 59)
Compound (Vh)

化合物（V）のうち、化合物番号（１ｉ）〜（４ｉ）で表される化合物（Vｉ）を、表６０に例示する。
（表６０）
化合物（Vｉ）

Table 60 shows compounds (Vi) represented by compound numbers (1i) to (4i) among the compounds (V).
(Table 60)
Compound (Vi)

化合物（I）〜（VI）、（I’）、（II’）及び（V’）は、Ｉ型コラーゲン遺伝子、フィブロネクチン遺伝子等の細胞外マトリックス遺伝子の転写を抑制する能力を有する。当該能力は、Ｉ型コラーゲン遺伝子、フィブロネクチン遺伝子等の細胞外マトリックス遺伝子の発現量を減少させて、コラーゲン、フィブロネクチン等の細胞外マトリックスの蓄積量の低下を導くことにより組織の線維化を改善するために重要である。よって、化合物（I）〜（VI）、（I’）、（II’）及び（V’）は、Ｉ型コラーゲン遺伝子、フィブロネクチン遺伝子等の細胞外マトリックス遺伝子の発現量を減少させてコラーゲン、フィブロネクチン等の細胞外マトリックスの蓄積量の低下を導くことにより組織の線維化を改善するための組成物（医薬品、化粧品、食品添加物等）の有効成分として利用することができる。
本発明転写抑制組成物や本発明線維化改善組成物の適用可能な疾患としては、例えば、コラーゲン、フィブロネクチン等の細胞外マトリックスの過度の集積により組織が線維化することにより硬化し、その結果、臓器等の組織の機能低下や瘢痕形成等を来たす疾患（即ち、線維症等）をあげることができる。具体的には例えば、肝硬変、慢性膵炎、スキルス胃癌、間質性肺疾患、喘息、慢性閉塞性肺疾患、糸球体腎炎、ループス腎炎、尿細管間質性腎炎、ＩｇＡ腎症、腎硬化症、糖尿病性腎症、遺伝性腎疾患、心筋線維症、心不全、ＰＴＣＡ後の再狭窄、動脈硬化、骨髄線維症、関節リウマチ、炎症後の過形成痕跡、術後の瘢痕や熱傷性瘢痕、アトピー性皮膚炎、肥厚性瘢痕、子宮筋腫、前立腺肥大症、強皮症、アルツハイマー病、硬化性腹膜炎、糖尿病性網膜症、I型糖尿病等をあげることができる。因みに、肝硬変においては、１つの例として、Ｃ型又はＢ型肝炎ウイルスが慢性的な炎症を誘発し、ＴＧＦ−βの量が上昇することにより、肝線維化（特に、Ｉ型・III型コラーゲンの蓄積）を引き起こして当該疾患となることがすでに知られている（例えば、Ｃｌｉｎ．ＬｉｖｅｒＤｉｓ．，７，１９５−２１０（２００３）参照）。間質性肺疾患においては、１つの例として、ダニ・ウイルス・結核菌等による肺炎を誘発してＴＧＦ-βの量が上昇し、肺線維化を引き起こして当該疾患となると考えられている。糖尿病性腎症やＩｇＡ腎症等の慢性腎不全においては、前者では高血糖によって腎糸球体でＴＧＦ−βの量が上昇し、後者ではＩｇＡが腎糸球体に蓄積することにより、腎炎を誘発してＴＧＦ−βの量が上昇し、腎線維化（特に、Ｉ型・IV型コラーゲンの蓄積）を引き起こして当該疾患となることがすでに示唆されている（例えば、Ａｍ．Ｊ．Ｐｈｙｓｉｏｌ．ＲｅｎａｌＰｈｓｉｏｌ．，２７８，Ｆ８３０−Ｆ８３８（２０００）、ＫｉｄｎｅｙＩｎｔ．，６４，１４９−１５９（２００３）参照）。尚、糖尿病性腎症のモデル動物であるｄｂ／ｄｂマウスとは、摂食を抑制するレプチン受容体に変異をもつため、過食により高血糖となり自然発症的に糖尿病を併発するものである。ｄｂ／ｄｂマウスは、正常マウスに比較して血中グルコース濃度が約４倍高く、腎糸球体線維化とＴＧＦ−β量との増加が認められている（例えば、Ａｍ．Ｊ．Ｐａｔｈｏｌ．，１５８，１６５３−１６６３（２００１）参照）。またＩｇＡ腎症のモデル動物である抗Ｔｈｙ−１ラットとは、抗Ｔｈｙ−１抗体を正常ラットに投与することにより、人工的に腎線維化を引き起こさせたものである。当該モデル動物に対して抗ＴＧＦ−β受容体抗体を投与することにより、腎線維化が抑制されることが示されている（例えば、ＫｉｄｎｅｙＩｎｔ．，６０，１７４５−１７５５（２００１）参照）。強皮症においては、その原因は不明だが、そのモデル動物であるＴｓｋマウスに対し、ＴＧＦ−β阻害剤を投与することにより皮膚線維化の改善が認められている（例えば、Ｊ．Ｉｎｖｅｓｔ．Ｄｅｒｍａｔｏｌ．，１１８，４６１−４７０（２００１）参照）。以上のことから、ＴＧＦ−βの作用を抑制する化合物は、ＴＧＦ−βによるコラーゲン合成促進を阻害して組織の線維化を抑制し、線維症治療効果を得るための組成物（医薬品、化粧品、食品添加物等）の有効成分として利用することができるのである。一方、左室拡張不全等の心不全の病因は、高血圧状態の心臓線維化がその１つとされている。以上のことから、ＴＧＦ−βによるフィブロネクチン合成促進を阻害して組織の線維化を抑制し、心不全治療効果を得るための組成物（医薬品等）の有効成分として利用することができるのである。
かかる本発明転写抑制組成物や本発明線維化改善組成物は、化合物（I）〜（VI）、（I’）、（II’）及び（V’）と不活性担体とを含有する。これらの組成物中に含有される化合物（I）〜（VI）、（I’）、（II’）及び（V’）は、通常、０．０１重量％〜９９．９９重量％であり、不活性担体は、通常、９９．９９重量％〜０．０１重量％である。該不活性担体は、薬学的に許容される担体や賦形剤であり、本発明転写抑制組成物や本発明線維化改善組成物はさらに、医薬品添加剤、化粧品添加剤、食品添加剤等を含有してもよい。 Compounds (I) to (VI), (I ′), (II ′) and (V ′) have the ability to suppress transcription of extracellular matrix genes such as type I collagen gene and fibronectin gene. This ability is to improve tissue fibrosis by reducing the expression level of extracellular matrix genes such as type I collagen gene and fibronectin gene, leading to a decrease in the accumulated amount of extracellular matrix genes such as collagen and fibronectin. Is important to. Therefore, the compounds (I) to (VI), (I ′), (II ′) and (V ′) reduce the expression level of extracellular matrix genes such as type I collagen gene and fibronectin gene, thereby reducing collagen and fibronectin. It can be used as an active ingredient of a composition (pharmaceutical, cosmetic, food additive, etc.) for improving tissue fibrosis by leading to a decrease in the amount of extracellular matrix accumulated.
Examples of the diseases to which the transcription repressing composition of the present invention and the composition for improving fibrosis of the present invention can be applied include, for example, hardening by tissue fibrosis due to excessive accumulation of extracellular matrix such as collagen and fibronectin. Diseases (ie, fibrosis, etc.) that cause decreased function of tissues such as organs and scar formation can be mentioned. Specifically, for example, cirrhosis, chronic pancreatitis, Skills gastric cancer, interstitial lung disease, asthma, chronic obstructive pulmonary disease, glomerulonephritis, lupus nephritis, tubulointerstitial nephritis, IgA nephropathy, nephrosclerosis, Diabetic nephropathy, hereditary kidney disease, myocardial fibrosis, heart failure, restenosis after PTCA, arteriosclerosis, myelofibrosis, rheumatoid arthritis, post-inflammation hyperplasia, postoperative scar or burn scar, atopic Examples include dermatitis, hypertrophic scar, uterine fibroids, prostatic hypertrophy, scleroderma, Alzheimer's disease, sclerosing peritonitis, diabetic retinopathy, type I diabetes and the like. Incidentally, in cirrhosis, as an example, hepatitis C virus or hepatitis B induces chronic inflammation and increases the amount of TGF-β, resulting in liver fibrosis (particularly type I and type III collagen). (See, for example, Clin. Liver Dis., 7, 195-210 (2003)). In interstitial lung disease, as an example, it is considered that pneumonia caused by mites, viruses, tuberculosis bacteria, and the like is induced to increase the amount of TGF-β, causing pulmonary fibrosis and causing the disease. In chronic renal failure such as diabetic nephropathy and IgA nephropathy, the amount of TGF-β increases in the glomeruli due to hyperglycemia in the former, and the latter induces nephritis by accumulation of IgA in the glomeruli. It has already been suggested that the amount of TGF-β increases and causes renal fibrosis (particularly, accumulation of type I and type IV collagen), resulting in the disease (for example, Am. J. Physiol. Phsiol., 278, F830-F838 (2000), Kidney Int., 64, 149-159 (2003)). The db / db mouse, which is a model animal for diabetic nephropathy, has a mutation in the leptin receptor that suppresses feeding, and thus hyperglycemia occurs due to overeating and spontaneously accompanies diabetes. In db / db mice, blood glucose concentration is about 4 times higher than in normal mice, and glomerular fibrosis and increase in TGF-β amount are observed (for example, Am. J. Pathol.,). 158, 1653-1663 (2001)). The anti-Thy-1 rat, which is a model animal of IgA nephropathy, is an artificially induced renal fibrosis by administering an anti-Thy-1 antibody to a normal rat. It has been shown that renal fibrosis is suppressed by administering an anti-TGF-β receptor antibody to the model animal (see, for example, Kidney Int., 60, 1745-1755 (2001)). Although the cause of scleroderma is unknown, improvement of skin fibrosis has been observed by administering a TGF-β inhibitor to the Tsk mouse, which is the model animal (for example, J. Invest. Dermatol). , 118, 461-470 (2001)). From the above, the compound that suppresses the action of TGF-β inhibits the promotion of collagen synthesis by TGF-β, suppresses tissue fibrosis, and obtains a fibrosis therapeutic effect (pharmaceuticals, cosmetics, It can be used as an active ingredient of food additives and the like. On the other hand, heart fibrosis in a hypertensive state is one of the causes of heart failure such as left ventricular diastolic failure. From the above, it can be used as an active ingredient of a composition (medicine or the like) for inhibiting fibronectin synthesis promotion by TGF-β to suppress tissue fibrosis and obtaining a therapeutic effect on heart failure.
Such a transcription repressing composition of the present invention and a composition for improving fibrosis of the present invention contain compounds (I) to (VI), (I ′), (II ′) and (V ′) and an inert carrier. The compounds (I) to (VI), (I ′), (II ′) and (V ′) contained in these compositions are usually 0.01% to 99.99% by weight, The inert carrier is usually 99.99% to 0.01% by weight. The inert carrier is a pharmaceutically acceptable carrier or excipient, and the transcription inhibitor composition or the fibrosis improving composition of the present invention further contains a pharmaceutical additive, a cosmetic additive, a food additive, etc. You may contain.

また、化合物（I）〜（VI）、（I’）、（II’）及び（V’）は、後述する実施例３，４にも示されるように、ＴＧＦ−βが有するＩ型コラーゲン遺伝子の転写促進能力を阻害する。即ち、化合物（I）〜（VI）、（I’）、（II’）及び（V’）はＴＧＦ−βの作用を抑制する能力を有するＴＧＦ−βアンタゴニストである。よって、化合物（I）〜（VI）、（I’）、（II’）及び（V’）は、ＴＧＦ−β作用抑制組成物の有効成分として利用することもできる。ＴＧＦ−βは、毛髪の成長サイクルにおける成長期（以下、毛髪成長期と記すこともある。）から退行期（以下、毛髪退行期と記すこともある。）への移行を促進する能力を有することが知られている［Ｊ．Ｉｎｖｅｓｔ．Ｄｅｒｍａｔｏｌ．，１１１，９４８−９５４（１９９８）、ＦＡＳＥＢＪ．，１６，１９６７−１９６９（２００２）］。さらに、抗ＴＧＦ−β抗体や、ＴＧＦ−β阻害剤であるＦｅｔｕｉｎ等は、ＴＧＦ−βによる毛の伸長抑制作用に対して拮抗的に働き、毛の伸長促進作用を示すことが報告されている［Ｊ．Ｉｎｖｅｓｔ．Ｄｅｒｍａｔｏｌ．，１１８，９９３−９９７（２００２）、公開特許公報特開２０００−３４２２９６］。よって、本発明化合物（及びこれを有効成分として含有するＴＧＦ−β作用抑制組成物）は、ＴＧＦ−βによる毛髪退行期への移行促進を阻害して毛髪成長期の延長を導くことにより養毛効果を得るために利用してもよい。
かかる本発明ＴＧＦ−β抑制組成物や本発明養毛組成物は、化合物（I）〜（VI）、（I’）、（II’）及び（V’）と不活性担体とを含有する。これらの組成物中に含有される化合物（I）〜（VI）、（I’）、（II’）及び（V’）は、通常、０．０１重量％〜９９．９９重量％であり、不活性担体は、通常、９９．９９重量％〜０．０１重量％である。当該不活性担体は、薬学的に許容される担体や賦形剤であり、本発明ＴＧＦ−β抑制組成物や本発明養毛組成物はさらに、医薬品添加剤、化粧品添加剤、食品添加剤等を含有してもよい。 In addition, compounds (I) to (VI), (I ′), (II ′) and (V ′) are a type I collagen gene possessed by TGF-β as shown in Examples 3 and 4 described later. Inhibits the ability to promote transcription. That is, compounds (I) to (VI), (I ′), (II ′) and (V ′) are TGF-β antagonists having an ability to suppress the action of TGF-β. Therefore, the compounds (I) to (VI), (I ′), (II ′) and (V ′) can also be used as active ingredients of the TGF-β action inhibitory composition. TGF-β has the ability to promote the transition from the growth phase (hereinafter sometimes referred to as hair growth phase) to the regression phase (hereinafter also referred to as hair regression phase) in the hair growth cycle. It is known [J. Invest. Dermatol. 111, 948-954 (1998), FASEB J. et al. 16, 1967-1969 (2002)]. Furthermore, it has been reported that anti-TGF-β antibody, Teutin, which is a TGF-β inhibitor, act antagonistically to TGF-β to suppress hair elongation and show hair elongation promoting effect. [J. Invest. Dermatol. , 118, 993-997 (2002), published patent publication JP 2000-342296]. Therefore, the compound of the present invention (and the TGF-β action-suppressing composition containing this as an active ingredient) inhibits the promotion of the transition to the hair regression phase by TGF-β and leads to the extension of the hair growth phase. It may be used to obtain an effect.
Such a TGF-β inhibitory composition of the present invention and a hair nourishing composition of the present invention contain compounds (I) to (VI), (I ′), (II ′) and (V ′) and an inert carrier. The compounds (I) to (VI), (I ′), (II ′) and (V ′) contained in these compositions are usually 0.01% to 99.99% by weight, The inert carrier is usually 99.99% to 0.01% by weight. The inert carrier is a pharmaceutically acceptable carrier or excipient, and the TGF-β-suppressing composition of the present invention and the hair nourishing composition of the present invention further include pharmaceutical additives, cosmetic additives, food additives, etc. It may contain.

上記組成物に用いられる薬学的に許容される担体、賦形剤、医薬品添加剤、食品添加剤、化粧品添加剤等は、当該組成物の具体的用途に応じて適宜選択することができる。また、当該組成物の形態も、具体的用途に応じて、例えば、種々の固体、液体等の形態とすることができる。
例えば、化合物（I）〜（VI）、（I’）、（II’）及び（V’）を医薬品の有効成分として用いる場合には、具体的な形態として、例えば、散剤、細粒剤、顆粒剤、錠剤、シロップ剤、カプセル剤、懸濁化剤、エマルジョン剤、エキス剤及び丸剤等の経口剤、注射剤、外用液剤や軟膏剤等の経皮吸収剤、坐剤及び局所剤等の非経口剤等をあげることができる。
経口剤は、例えば、ゼラチン、アルギン酸ナトリウム、澱粉、コーンスターチ、白糖、乳糖、ぶどう糖、マンニット、カルボキシメチルセルロース、デキストリン、ポリビニルピロリドン、結晶セルロース、大豆レシチン、ショ糖、脂肪酸エステル、タルク、ステアリン酸マグネシウム、ポリエチレングリコール、ケイ酸マグネシウム、無水ケイ酸等の担体や賦形剤、結合剤、崩壊剤、界面活性剤、滑沢剤、流動性促進剤、希釈剤、保存剤、着色剤、香料、安定化剤、保湿剤、防腐剤、酸化防止剤等の医薬品添加剤を用いて、通常の方法に従って製造することができる。
投与量は、投与される哺乳動物の年令、性別、体重、疾患の程度、本発明の組成物の種類、投与形態等によって異なるが、通常は経口の場合にはヒト成人で１日あたり有効成分量として約１ｍｇ〜約２ｇ、好ましくは有効成分量として約５ｍｇ〜約１ｇを投与すればよい。また、前記の１日の投与量を１回又は数回に分けて投与することができる。
非経口剤のうち、注射剤は、生理食塩水、滅菌水リンゲル液等の水溶性溶剤、植物油、脂肪酸エステル等の非水溶性溶剤、ブドウ糖、塩化ナトリウム等の等張化剤、溶解補助剤、安定化剤、防腐剤、懸濁化剤、乳化剤等の医薬品添加剤を用いて、通常の方法に従って製造することができる。外用液剤、ゲル状軟膏等の経皮吸収剤、直腸内投与のための坐剤等も通常の方法に従って製造することができる。このような非経口剤を投与するには、注射（皮下、静脈内等）、経皮投与、直腸投与すればよい。局所剤は、例えば、化合物（I）〜（VI）、（I’）、（II’）及び（V’）をエチレンビニル酢酸ポリマー等の徐放性ポリマーのペレットに取り込ませて製造することができる。このペレットを治療すべき組織中に外科的に移植すればよい。
投与量は、投与される哺乳動物の年令、性別、体重、疾患の程度、本発明の組成物の種類、投与形態等によって異なるが、通常は注射の場合にはヒト成人で有効成分量として約０．１ｍｇ〜約５００ｍｇを投与すればよい。また、前記の１日の投与量を１回又は数回に分けて投与することができる。
化合物（I）〜（VI）、（I’）、（II’）及び（V’）を化粧品に添加して用いる場合には、当該化合物が添加された化粧品の具体的な形態としては、例えば、液状、乳状、クリーム、ローション、軟膏、ゲル、エアゾール、ムース等をあげることができる。ローションは、例えば、懸濁剤、乳化剤、保存剤等の化粧品添加剤を用いて、通常の方法に従って製造することができる。
投与量は、投与される哺乳動物の年令、性別、体重、疾患の程度、本発明の組成物の種類、投与形態等によって異なるが、通常ヒト成人で有効成分量として約０．０１ｍｇ〜約５０ｍｇを投与すればよい。また、前記の１日の投与量を１回又は数回に分けて投与することができる。
化合物（I）〜（VI）、（I’）、（II’）及び（V’）を食品添加物として用いる場合には、当該添加物が添加された食品の具体的な形態としては、例えば、粉末、錠剤、飲料、摂取可能なゲル若しくはシロップとの混合液状物、例えば、調味料、和菓子、洋菓子、氷菓、飲料、スプレッド、ペースト、漬物、ビン缶詰、畜肉加工品、魚肉・水産加工品、乳・卵加工品、野菜加工品、果実加工品、穀類加工品等の一般的な飲食物や嗜好物等をあげることができる。また、家畜、家禽、蜜蜂、蚕、魚等の飼育動物のための飼料や餌料への添加も可能である。
投与量は、投与される哺乳動物の年令、性別、体重、疾患の程度、本発明の組成物の種類、投与形態等によって異なるが、通常ヒト成人で有効成分量として約０．１ｍｇ〜約５００ｍｇを投与すればよい。また、前記の１日の投与量を１回又は数回に分けて投与することができる。 The pharmaceutically acceptable carrier, excipient, pharmaceutical additive, food additive, cosmetic additive and the like used in the composition can be appropriately selected depending on the specific use of the composition. Moreover, the form of the said composition can also be made into forms, such as various solid and liquid, according to a specific use, for example.
For example, when the compounds (I) to (VI), (I ′), (II ′) and (V ′) are used as active ingredients of pharmaceuticals, as specific forms, for example, powders, fine granules, Oral preparations such as granules, tablets, syrups, capsules, suspending agents, emulsions, extracts and pills, transdermal absorption agents such as injections, external liquids and ointments, suppositories, and topical agents Parenteral preparations and the like.
Oral preparations include, for example, gelatin, sodium alginate, starch, corn starch, sucrose, lactose, glucose, mannitol, carboxymethylcellulose, dextrin, polyvinylpyrrolidone, crystalline cellulose, soy lecithin, sucrose, fatty acid ester, talc, magnesium stearate, Carriers and excipients such as polyethylene glycol, magnesium silicate, and silicic anhydride, binders, disintegrants, surfactants, lubricants, fluidity promoters, diluents, preservatives, colorants, fragrances, stabilization It can be produced according to a usual method using a pharmaceutical additive such as an agent, a humectant, a preservative, and an antioxidant.
The dose varies depending on the age, sex, weight, disease level, type of composition of the present invention, dosage form, etc., but is usually effective for human adults per day. About 1 mg to about 2 g may be administered as the component amount, preferably about 5 mg to about 1 g may be administered as the active component amount. In addition, the above-mentioned daily dose can be administered once or divided into several times.
Among parenterals, injections are water-soluble solvents such as physiological saline and sterile water Ringer's solution, water-insoluble solvents such as vegetable oils and fatty acid esters, isotonic agents such as glucose and sodium chloride, solubilizing agents, stable It can be produced according to a usual method using a pharmaceutical additive such as an agent, a preservative, a suspending agent and an emulsifier. External liquid preparations, transdermal absorption agents such as gel ointments, suppositories for rectal administration, and the like can also be produced according to ordinary methods. In order to administer such a parenteral preparation, injection (subcutaneous, intravenous, etc.), transdermal administration, or rectal administration may be used. The topical agent can be produced, for example, by incorporating the compounds (I) to (VI), (I ′), (II ′) and (V ′) into pellets of a sustained release polymer such as ethylene vinyl acetate polymer. it can. This pellet may be surgically implanted into the tissue to be treated.
The dose varies depending on the age, sex, weight, disease level, type of composition of the present invention, dosage form, etc. of the mammal to be administered. About 0.1 mg to about 500 mg may be administered. In addition, the above-mentioned daily dose can be administered once or divided into several times.
When the compounds (I) to (VI), (I ′), (II ′) and (V ′) are used by being added to cosmetics, as specific forms of the cosmetics to which the compounds are added, for example, , Liquid, milky, cream, lotion, ointment, gel, aerosol, mousse and the like. Lotions can be produced according to conventional methods using cosmetic additives such as suspending agents, emulsifying agents, preservatives and the like.
The dosage varies depending on the age, sex, weight, disease level, type of composition of the present invention, dosage form, etc. of the mammal to be administered. 50 mg may be administered. In addition, the above-mentioned daily dose can be administered once or divided into several times.
When the compounds (I) to (VI), (I ′), (II ′) and (V ′) are used as food additives, specific forms of foods to which the additives are added include, for example, , Powders, tablets, beverages, mixed liquids with ingestible gel or syrup, such as seasonings, Japanese confectionery, Western confectionery, ice confectionery, beverages, spreads, pastes, pickles, canned bottles, processed meat products, processed fish and fishery products And general foods and beverages such as processed milk / eggs, processed vegetables, processed fruits, processed cereals, and the like. Further, it can be added to feed and feed for domestic animals such as domestic animals, poultry, bees, cormorants and fish.
The dose varies depending on the age, sex, body weight, degree of disease, type of composition of the present invention, dosage form, etc. of the mammal to be administered, but it is usually about 0.1 mg to about 0.1 mg as an active ingredient in human adults. 500 mg may be administered. In addition, the above-mentioned daily dose can be administered once or divided into several times.

以下に実施例を挙げ、本発明を更に具体的に説明する。
実施例１実施例１−１から１−１５に、本発明アルデヒド誘導体の合成を記す。 Hereinafter, the present invention will be described in more detail with reference to examples.
Example 1 Synthesis of the aldehyde derivative of the present invention is described in Examples 1-1 to 1-15.

実施例１−１本発明アルデヒド誘導体［化合物番号（ａ）］の合成
5-ホルミルチオフェン-2-カルボン酸１．５６ｇのテトラヒドロフラン４０ｍｌ溶液に、カルボニルジイミダゾール２．１１ｇを添加し、室温で２時間３０分攪拌した。ここに、2-メトキシエチルアミン１ｍｌを添付し、室温で１時間３０分攪拌した後、減圧濃縮した。得られた残渣を酢酸エチル７０ｍｌに溶解して２規定塩酸、飽和重曹水の順に洗浄し、無水硫酸ナトリウムで乾燥した後、減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに供することにより、5-ホルミルチオフェン-2-カルボン酸 2-メトキシエチルアミド［化合物番号（ａ）］の白色固体０．８８ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．２７（ｓ，３Ｈ），３．３８〜３．５０（ｍ，４Ｈ），７．８９（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），８．０１（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），８．９１（ｂｒｏａｄ，１Ｈ），９．９５（ｓ，１Ｈ） Example 1-1 Synthesis of the present aldehyde derivative [Compound No. (a)]
To a solution of 1.56 g of 5-formylthiophene-2-carboxylic acid in 40 ml of tetrahydrofuran was added 2.11 g of carbonyldiimidazole, and the mixture was stirred at room temperature for 2 hours and 30 minutes. To this was added 1 ml of 2-methoxyethylamine, and the mixture was stirred at room temperature for 1 hour 30 minutes, and then concentrated under reduced pressure. The obtained residue was dissolved in 70 ml of ethyl acetate, washed with 2N hydrochloric acid and saturated aqueous sodium bicarbonate in this order, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.88 g of white solid of 5-formylthiophene-2-carboxylic acid 2-methoxyethylamide [Compound No. (a)].
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.27 (s, 3H), 3.38 to 3.50 (m, 4H), 7.89 (d, 1H, J = 4) .1 Hz), 8.01 (d, 1 H, J = 4.1 Hz), 8.91 (broad, 1 H), 9.95 (s, 1 H)

実施例１−２本発明アルデヒド誘導体［化合物番号（ｂ）］の合成
5-ホルミルフラン-2-カルボン酸２．８０ｇのテトラヒドロフラン３０ｍｌ及びジメチルホルムアミド３０ｍｌ溶液に、カルボニルジイミダゾール４．２２ｇを添加し、室温で１時間攪拌し、2-メトキシエチルアミン６ｍｌを添加して、室温で一夜攪拌した。還流下で５時間加熱した後、２規定塩酸を加えて酢酸エチルで抽出し、有機層を飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥して減圧濃縮し、5-ホルミルフラン-2-カルボン酸 2-メトキシエチルアミド［化合物番号（ｂ）］の白色固体３．０１ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．２６（ｓ，３Ｈ），３．３７〜３．４８（ｍ，４Ｈ），７．３２（ｄ，１Ｈ，Ｊ＝３．６Ｈｚ），７．６０（ｄ，１Ｈ，Ｊ＝３．６Ｈｚ），８．７７（ｂｒｏａｄ，１Ｈ），９．７０（ｓ，１Ｈ） Example 1-2 Synthesis of the present aldehyde derivative [Compound No. (b)]
To a solution of 2.80 g of 5-formylfuran-2-carboxylic acid in 30 ml of tetrahydrofuran and 30 ml of dimethylformamide, 4.22 g of carbonyldiimidazole is added and stirred at room temperature for 1 hour, and 6 ml of 2-methoxyethylamine is added. And stirred overnight. After heating at reflux for 5 hours, 2N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 5-formylfuran-2- 3.01 g of a white solid of carboxylic acid 2-methoxyethylamide [Compound No. (b)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.26 (s, 3H), 3.37 to 3.48 (m, 4H), 7.32 (d, 1H, J = 3) .6 Hz), 7.60 (d, 1 H, J = 3.6 Hz), 8.77 (broad, 1 H), 9.70 (s, 1 H)

実施例１−３本発明アルデヒド誘導体［化合物番号（ｃ）］の合成
5-ホルミルチオフェン-2-カルボン酸の代わりに、5-ホルミル-1-メチル-1H-ピロール-2-カルボン酸２．３０ｇを用いた以外は実施例１−１と同様にして、5-ホルミル-1-メチル-1H-ピロール-2-カルボン酸 2-メトキシエチルアミド［化合物番号（ｃ）］の黄色結晶１．１０ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．２８（ｓ，３Ｈ），３．３１〜３．５４（ｍ，４Ｈ），４．１４（ｓ，３Ｈ），６．８２（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），７．０２（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），８．５５（ｂｒｏａｄｔ，１Ｈ，Ｊ＝４．９Ｈｚ），９．６８（ｓ，１Ｈ） Example 1-3 Synthesis of the present aldehyde derivative [Compound No. (c)]
5-Formyl was obtained in the same manner as in Example 1-1 except that 2.30 g of 5-formyl-1-methyl-1H-pyrrole-2-carboxylic acid was used instead of 5-formylthiophene-2-carboxylic acid. 1.10 g of yellow crystals of -1-methyl-1H-pyrrole-2-carboxylic acid 2-methoxyethylamide [Compound No. (c)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.28 (s, 3H), 3.31 to 3.54 (m, 4H), 4.14 (s, 3H), 6. 82 (d, 1H, J = 4.1 Hz), 7.02 (d, 1H, J = 4.1 Hz), 8.55 (broad t, 1H, J = 4.9 Hz), 9.68 (s, 1H)

実施例１−４本発明アルデヒド誘導体［化合物番号（ｄ）］の合成
5-ホルミルチオフェン-2-カルボン酸の代わりに、4-ホルミル-1-メチル-1H-ピロール-2-カルボン酸２．００ｇを用いた以外は実施例１−１と同様にして、4-ホルミル-1-メチル-1H-ピロール-2-カルボン酸 2-メトキシエチルアミド［化合物番号（ｄ）］の白色結晶０．５２ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＣＤＣｌ₃）δ（ｐｐｍ）：３．３７（ｓ，３Ｈ），３．４９〜３．６５（ｍ，４Ｈ），４．００（ｓ，３Ｈ），６．３８（ｂｒｏａｄ，１Ｈ），７．０１（ｄ，１Ｈ，Ｊ＝１．６Ｈｚ），７．３３（ｄ，１Ｈ，Ｊ＝１．６Ｈｚ），９．７５（ｓ，１Ｈ） Example 1-4 Synthesis of the present aldehyde derivative [Compound No. (d)]
4-Formyl was obtained in the same manner as in Example 1-1 except that 2.00 g of 4-formyl-1-methyl-1H-pyrrole-2-carboxylic acid was used instead of 5-formylthiophene-2-carboxylic acid. 0.52 g of white crystals of -1-methyl-1H-pyrrole-2-carboxylic acid 2-methoxyethylamide [Compound No. (d)] was obtained.
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 3.37 (s, 3H), 3.49 to 3.65 (m, 4H), 4.00 (s, 3H), 6.38 ( broadcast, 1H), 7.01 (d, 1H, J = 1.6 Hz), 7.33 (d, 1H, J = 1.6 Hz), 9.75 (s, 1H)

実施例１−５本発明アルデヒド誘導体［化合物番号（ｅ）］の合成
5-ホルミルチオフェン-2-カルボン酸１．５６ｇ及びN-ヒドロキシこはく酸イミド１．１５ｇのジメチルホルムアミド１５ｍｌ溶液に、N，N’-ジシクロヘキシルカルボジイミド２．０６ｇのジメチルホルムアミド５ｍｌ溶液を添加し、室温で３０分攪拌した。不溶物を濾別してジメチルホルムアミド１０ｍｌで洗浄し、濾液に2-ヒドロキシエチルアミン１．２ｍｌを添加し、室温で１時間３０分攪拌した。不溶物を濾別して濾液を減圧濃縮し、残渣をメタノール５０ｍｌに溶解して１０％塩酸３０ｍｌを添加し、室温で一夜攪拌した。反応液を減圧濃縮し、得られた残渣を酢酸エチル４００ｍｌに溶解して水洗し、無水硫酸ナトリウムで乾燥した後、減圧濃縮して、5-ホルミルチオフェン-2-カルボン酸 2-ヒドロキシエチルアミド［化合物番号（ｅ）］の黄色固体０．５８ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．２９〜３．３７（ｍ，２Ｈ），３．４８〜３．５５（ｍ，２Ｈ），４．７８（ｔ，１Ｈ，Ｊ＝５．７Ｈｚ），７．８９（ｄ，１Ｈ，Ｊ＝３．９Ｈｚ），８．０１（ｄ，１Ｈ，Ｊ＝３．９Ｈｚ），８．８３（ｔ，１Ｈ，Ｊ＝５．４Ｈｚ），９．９５（ｓ，１Ｈ） Example 1-5 Synthesis of the present aldehyde derivative [Compound No. (e)]
To a solution of 1.56 g of 5-formylthiophene-2-carboxylic acid and 1.15 g of N-hydroxysuccinimide in 15 ml of dimethylformamide was added 2.06 g of N, N'-dicyclohexylcarbodiimide in 5 ml of dimethylformamide at room temperature. Stir for 30 minutes. The insoluble material was filtered off and washed with 10 ml of dimethylformamide. 1.2 ml of 2-hydroxyethylamine was added to the filtrate, and the mixture was stirred at room temperature for 1 hour and 30 minutes. Insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in 50 ml of methanol, 30 ml of 10% hydrochloric acid was added, and the mixture was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, and the resulting residue was dissolved in 400 ml of ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 5-formylthiophene-2-carboxylic acid 2-hydroxyethylamide [ 0.58 g of a yellow solid of Compound No. (e)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.29 to 3.37 (m, 2H), 3.48 to 3.55 (m, 2H), 4.78 (t, 1H , J = 5.7 Hz), 7.89 (d, 1H, J = 3.9 Hz), 8.01 (d, 1H, J = 3.9 Hz), 8.83 (t, 1H, J = 5. 4Hz), 9.95 (s, 1H)

実施例１−６本発明アルデヒド誘導体［化合物番号（ｋ）］の合成
5-ホルミルチオフェン-2-カルボン酸０．８０ｇのテトラヒドロフラン１０ｍｌ溶液に、カルボニルジイミダゾール１．２５ｇを添加し、室温で３０分攪拌した。この反応液を、グリシンアミド０．８５ｇ、トリエチルアミン１ｍｌ及びテトラヒドロフラン１０ｍｌの混合物に添加し、室温で一夜攪拌した。１０％塩酸を加えて酢酸エチルで抽出し、有機層を重曹水で洗浄した後、無水硫酸ナトリウムで乾燥して減圧濃縮し、得られた固体をヘキサンで洗浄して、5-ホルミルチオフェン-2-カルボン酸カルバモイルメチルアミド［化合物番号（ｋ）］の黄色固体０．２１ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．８２（ｄ，２Ｈ，Ｊ＝６．２Ｈｚ），７．０９（ｂｒｏａｄｓ，１Ｈ），７．４６（ｂｒｏａｄｓ，１Ｈ），７．９２（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），８．０３（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），９．０６（ｔ，１Ｈ，Ｊ＝５．９Ｈｚ），９．９７（ｓ，１Ｈ） Example 1-6 Synthesis of the present aldehyde derivative [Compound No. (k)]
To a solution of 0.80 g of 5-formylthiophene-2-carboxylic acid in 10 ml of tetrahydrofuran was added 1.25 g of carbonyldiimidazole, and the mixture was stirred at room temperature for 30 minutes. This reaction solution was added to a mixture of 0.85 g of glycinamide, 1 ml of triethylamine and 10 ml of tetrahydrofuran, and stirred overnight at room temperature. 10% Hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting solid was washed with hexane to give 5-formylthiophene-2. -Carboxylic acid 0.21 g of yellow solid of carbamoylmethylamide [Compound No. (k)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.82 (d, 2H, J = 6.2 Hz), 7.09 (broads, 1H), 7.46 (broads, 1H) ), 7.92 (d, 1H, J = 4.1 Hz), 8.03 (d, 1H, J = 4.1 Hz), 9.06 (t, 1H, J = 5.9 Hz), 9.97 (S, 1H)

実施例１−７本発明アルデヒド誘導体［化合物番号（ｏ）］の合成
5-ホルミルチオフェン-2-カルボン酸４００ｍｇのジメチルホルムアミド溶液に、塩酸1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド５４０ｍｇ及びトリエチルアミン４１０μｌを添加し、氷冷下３０分攪拌した。この反応液に、N-(2-メトキシエチル)メチルアミン３００μｌを添加し、室温で攪拌した。１０％塩酸を加えて酢酸エチルで抽出し、有機層を重曹水で洗浄した後、無水硫酸ナトリウムで乾燥して減圧濃縮し、得られた残渣を酢酸エチルで洗浄して、5-ホルミルチオフェン-2-カルボン酸 N-(2-メトキシエチル)メチルアミド［化合物番号（ｏ）］２２１ｍｇを得た。
¹Ｈ−ＮＭＲ（３００ＭＨｚ，ＣＤＣｌ₃）δ（ｐｐｍ）：３．２２（ｂｒｏａｄｓ，３Ｈ），３．４２（ｓ，３Ｈ），３．５５〜３．７５（４Ｈ），７．４５（ｄ，１Ｈ，Ｊ＝３．６Ｈｚ），７．６９（ｄ，１Ｈ，Ｊ＝３．９Ｈｚ），９．９５（ｓ，１Ｈ） Example 1-7 Synthesis of aldehyde derivative of the present invention [Compound No. (o)]
To a dimethylformamide solution of 400 mg of 5-formylthiophene-2-carboxylic acid, 540 mg of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride and 410 μl of triethylamine were added and stirred for 30 minutes under ice cooling. To this reaction solution, 300 μl of N- (2-methoxyethyl) methylamine was added and stirred at room temperature. 10% Hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was washed with ethyl acetate and washed with 5-formylthiophene- 221 mg of 2-carboxylic acid N- (2-methoxyethyl) methylamide [Compound No. (o)] was obtained.
¹ H-NMR (300 MHz, CDCl ₃ ) δ (ppm): 3.22 (roads, 3H), 3.42 (s, 3H), 3.55 to 3.75 (4H), 7.45 (d , 1H, J = 3.6 Hz), 7.69 (d, 1H, J = 3.9 Hz), 9.95 (s, 1H)

実施例１−８本発明アルデヒド誘導体［化合物番号（ｐ）］の合成
5-ホルミルフラン-2-カルボン酸１．２０ｇのテトラヒドロフラン１５ｍｌ及びジメチルホルムアミド５ｍｌ溶液に、カルボニルジイミダゾール１．６７ｇを添加して室温で攪拌した後、N-(2-メトキシエチル)メチルアミン１．１１ｍｌを添加して、室温で２時間３０分攪拌した。溶媒を留去した後、１０％塩酸を加えて酢酸エチルで抽出し、有機層を重曹水と飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥して減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに供することにより、5-ホルミルフラン-2-カルボン酸 N-(2-メトキシエチル)メチルアミド［化合物番号（ｐ）］の黄色油状物を得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＣＤＣｌ₃）δ（ｐｐｍ）：３．１０（ｂｒｏａｄｓ，３Ｈ），３．３６（ｓ，３Ｈ），３．６０〜３．８０（４Ｈ），７．１５〜７．２５（１Ｈ），７．２５〜７．３０（１Ｈ），９．７３（ｓ，１Ｈ） Examples 1-8 Synthesis of the present aldehyde derivative [Compound No. (p)]
To a solution of 1.20 g of 5-formylfuran-2-carboxylic acid in 15 ml of tetrahydrofuran and 5 ml of dimethylformamide, 1.67 g of carbonyldiimidazole was added and stirred at room temperature, and then N- (2-methoxyethyl) methylamine 1. 11 ml was added and stirred at room temperature for 2 hours 30 minutes. After the solvent was distilled off, 10% hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain a yellow oil of 5-formylfuran-2-carboxylic acid N- (2-methoxyethyl) methylamide [Compound No. (p)].
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 3.10 (broad s, 3H), 3.36 (s, 3H), 3.60 to 3.80 (4H), 7.15 to 7 .25 (1H), 7.25 to 7.30 (1H), 9.73 (s, 1H)

実施例１−９本発明アルデヒド誘導体［化合物番号（ｑ）］の合成
5-ブロモメチルチオフェン-2-カルバルデヒド０．９５ｇ及び水酸化ナトリウム０．３１ｇのエチレングリコール２．０１ｇ溶液を、５５℃で２時間攪拌した。反応液を氷水に添加し、酢酸エチルで抽出し、有機層を飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥して減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに供することにより、5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒド［化合物番号（ｑ）］０．１５ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＣＤＣｌ₃）δ（ｐｐｍ）：３．６６（ｔ，１Ｈ，Ｊ＝４．９Ｈｚ），３．７９（ｔ，１Ｈ，Ｊ＝４．３Ｈｚ），４．７８（ｓ，２Ｈ），７．１０（ｄ，１Ｈ，Ｊ＝３．５Ｈｚ），７．６７（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），９．８９（ｓ，１Ｈ） Examples 1-9 Synthesis of the present aldehyde derivative [Compound No. (q)]
A solution of 0.91 g of 5-bromomethylthiophene-2-carbaldehyde and 2.01 g of ethylene glycol in 0.31 g of sodium hydroxide was stirred at 55 ° C. for 2 hours. The reaction mixture was added to ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.15 g of 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde [Compound No. (q)].
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 3.66 (t, 1 H, J = 4.9 Hz), 3.79 (t, 1 H, J = 4.3 Hz), 4.78 (s) , 2H), 7.10 (d, 1H, J = 3.5 Hz), 7.67 (d, 1H, J = 4.1 Hz), 9.89 (s, 1H)

実施例１−１０本発明アルデヒド誘導体［化合物番号（ｒ）］の合成
5-ブロモメチルチオフェン-2-カルバルデヒド３．５２ｇ、チオグリコール酸メチル２．７４ｇ及び炭酸カリウム２．８４ｇのジメチルスルホキシド２２ｍｌ溶液を、室温で２時間攪拌した。反応液を氷水に添加し、酢酸エチルで抽出し、有機層を飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥して減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに供することにより、[(5-ホルミルチオフェン-2-イル)メチルチオ]酢酸メチル［化合物番号（ｒ）］３．１６ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．３６（ｓ，３Ｈ），３．６２（ｓ，２Ｈ），４．１５（ｓ，２Ｈ），７．２１（ｄ，１Ｈ，Ｊ＝３．８Ｈｚ），７．８９（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），９．８６（ｓ，１Ｈ） Example 1-10 Synthesis of aldehyde derivative of the present invention [Compound No. (r)]
A solution of 3.52 g of 5-bromomethylthiophene-2-carbaldehyde, 2.74 g of methyl thioglycolate and 2.84 g of potassium carbonate in 22 ml of dimethyl sulfoxide was stirred at room temperature for 2 hours. The reaction mixture was added to ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 3.16 g of methyl [(5-formylthiophen-2-yl) methylthio] acetate [Compound No. (r)].
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.36 (s, 3H), 3.62 (s, 2H), 4.15 (s, 2H), 7.21 (d, 1H, J = 3.8 Hz), 7.89 (d, 1H, J = 4.1 Hz), 9.86 (s, 1H)

実施例１−１１本発明アルデヒド誘導体［化合物番号（ｓ）］の合成
4-ブロモチオフェン-2-カルバルデヒド８．２１ｇ、メトキシアセトアミド４．６０ｇ、Ｎ，Ｎ’−ジメチルエチレンジアミン３８０ｍｇ、炭酸カリウム２５．５７ｇ、よう化銅（I）８２９ｍｇ及びジオキサン５５ｍｌの混合物を、還流下に５時間４５分加熱した。反応液をシリカゲルカラムクロマトグラフィーに供することにより、N-(2-ホルミルチオフェン-4-イル)-2-メトキシアセトアミド［化合物番号（ｓ）］の淡黄色粉体２．５２ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＣＤＣｌ₃）δ（ｐｐｍ）：３．５２（ｓ，３Ｈ），４．０５（ｓ，２Ｈ），７．８７（ｄ，１Ｈ，Ｊ＝１．６Ｈｚ），７．９３（ｄ，１Ｈ，Ｊ＝１．６Ｈｚ），８．５７（ｂｒｏａｄｓ，１Ｈ），９．７８（ｓ，１Ｈ） Example 1-11 Synthesis of aldehyde derivative of the present invention [Compound No. (s)]
A mixture of 8.21 g of 4-bromothiophene-2-carbaldehyde, 4.60 g of methoxyacetamide, 380 mg of N, N′-dimethylethylenediamine, 25.57 g of potassium carbonate, 829 mg of copper (I) iodide and 55 ml of dioxane was refluxed. For 5 hours 45 minutes. The reaction solution was subjected to silica gel column chromatography to obtain 2.52 g of a pale yellow powder of N- (2-formylthiophen-4-yl) -2-methoxyacetamide [Compound No. (s)].
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 3.52 (s, 3H), 4.05 (s, 2H), 7.87 (d, 1H, J = 1.6 Hz), 7. 93 (d, 1H, J = 1.6 Hz), 8.57 (broad s, 1H), 9.78 (s, 1H)

実施例１−１２本発明アルデヒド誘導体［化合物番号（ｔ）］の合成
4-ブロモチオフェン-2-カルバルデヒドの代わりに、2-ブロモチオフェン-5-カルバルデヒド２．９２ｇを用いた以外は実施例１−１１と同様にして、N-(5-ホルミルチオフェン-2-イル)-2-メトキシアセトアミド［化合物番号（ｔ）］０．１１ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．３７（ｓ，３Ｈ），４．１５（ｓ，２Ｈ），７．０１（ｄ，１Ｈ，Ｊ＝４．３Ｈｚ），７．８１（ｄ，１Ｈ，Ｊ＝４．３Ｈｚ），９．７８（ｓ，１Ｈ），１１．７２（ｂｒｏａｄ，１Ｈ） Examples 1-12 Synthesis of the present aldehyde derivative [Compound No. (t)]
N- (5-formylthiophene-2-2) was obtained in the same manner as in Example 1-11 except that 2.92 g of 2-bromothiophene-5-carbaldehyde was used instead of 4-bromothiophene-2-carbaldehyde. Yl) -2-methoxyacetamide [Compound No. (t)] 0.11 g was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.37 (s, 3H), 4.15 (s, 2H), 7.01 (d, 1H, J = 4.3 Hz), 7.81 (d, 1H, J = 4.3 Hz), 9.78 (s, 1H), 11.72 (broad, 1H)

実施例１−１３本発明アルデヒド誘導体［化合物番号（ｕ）］の合成
メトキシアセトアミドの代わりに、カルバミン酸2-メトキシエチル２．０２ｇを用いた以外は実施例１−１１と同様にして、N-(2-ホルミルチオフェン-4-イル)カルバミン酸2-メトキシエチル［化合物番号（ｕ）］０．１２ｇを得た。
¹Ｈ−ＮＭＲ（３００ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．２８（ｓ，３Ｈ），３．５７（ｔ，２Ｈ，Ｊ＝４．５Ｈｚ），４．２２（ｔ，２Ｈ，Ｊ＝４．５Ｈｚ），７．７２（ｓ，１Ｈ），７．８５（ｓ，１Ｈ），９．８８（ｓ，１Ｈ），１０．３１（ｂｒｏａｄ，１Ｈ） Example 1-13 Synthesis of aldehyde derivative of the present invention [Compound No. (u)] In the same manner as in Example 1-11 except that 2.02 g of 2-methoxyethyl carbamate was used instead of methoxyacetamide, N- 0.12 g of 2-methoxyethyl (2-formylthiophen-4-yl) carbamate [Compound No. (u)] was obtained.
¹ H-NMR (300 MHz, DMSO-d ₆ ) δ (ppm): 3.28 (s, 3H), 3.57 (t, 2H, J = 4.5 Hz), 4.22 (t, 2H, J = 4.5 Hz), 7.72 (s, 1H), 7.85 (s, 1H), 9.88 (s, 1H), 10.31 (broad, 1H)

実施例１−１４本発明アルデヒド誘導体［化合物番号（ｖ）］の合成
4-ブロモチオフェン-2-カルバルデヒドの代わりに、2-ブロモチオフェン-5-カルバルデヒド３．７６ｇを用い、メトキシアセトアミドの代わりに、カルバミン酸2-メトキシエチル２．８１ｇを用いた以外は実施例１−１１と同様にして、、N-(5-ホルミルチオフェン-2-イル)カルバミン酸2-メトキシエチル［化合物番号（ｖ）］０．１５ｇを得た。
¹Ｈ−ＮＭＲ（３００ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．２８（ｓ，３Ｈ），３．５７〜３．６０（２Ｈ），４．２７〜４．３０（２Ｈ），６．６９（ｄ，１Ｈ，Ｊ＝４．２Ｈｚ），７．７８（ｄ，１Ｈ，Ｊ＝３．９Ｈｚ），９．７２（ｓ，１Ｈ），１１．５５（ｂｒｏａｄ，１Ｈ） Example 1-14 Synthesis of the present aldehyde derivative [Compound No. (v)]
Example except that 3.76 g of 2-bromothiophene-5-carbaldehyde was used instead of 4-bromothiophene-2-carbaldehyde, and 2.81 g of 2-methoxyethyl carbamate was used instead of methoxyacetamide In the same manner as in 1-11, 0.15 g of 2-methoxyethyl N- (5-formylthiophen-2-yl) carbamate [Compound No. (v)] was obtained.
¹ H-NMR (300 MHz, DMSO-d ₆ ) δ (ppm): 3.28 (s, 3H), 3.57 to 3.60 (2H), 4.27 to 4.30 (2H), 6. 69 (d, 1H, J = 4.2 Hz), 7.78 (d, 1H, J = 3.9 Hz), 9.72 (s, 1H), 11.55 (broad, 1H)

実施例１−１５本発明アルデヒド誘導体［化合物番号（ｗ）］の合成
2-アミノ-5-ホルミルチアゾール２．５０ｇ及びトリエチルアミン２．４４ｇのテトラヒドロフラン３０ｍｌ溶液に、メトキシアセチルクロリド２．２２ｇのテトラヒドロフラン８ｍｌ溶液を氷冷下に滴下し、室温で２時間３０分攪拌した。不溶物を濾別し、濾液を氷水に添加して酢酸エチルで抽出し、有機層を１０％塩酸と飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥して減圧濃縮し、N-(5-ホルミルチアゾール-2-イル)-2-メトキシアセトアミド［化合物番号（ｗ）］の淡黄色粉体２．８３ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．３６（ｓ，３Ｈ），４．２２（ｓ，２Ｈ），８．４２（ｓ，１Ｈ），９．９７（ｓ，１Ｈ）
Example 1-15 Synthesis of aldehyde derivative of the present invention [Compound No. (w)]
To a solution of 2.50 g of 2-amino-5-formylthiazole and 2.44 g of triethylamine in 30 ml of tetrahydrofuran was added dropwise a solution of 2.22 g of methoxyacetyl chloride in 8 ml of tetrahydrofuran under ice cooling, and the mixture was stirred at room temperature for 2 hours and 30 minutes. The insoluble material was filtered off, the filtrate was added to ice water and extracted with ethyl acetate. The organic layer was washed with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and N- (5 There was obtained 2.83 g of a pale yellow powder of -formylthiazol-2-yl) -2-methoxyacetamide [Compound No. (w)].
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.36 (s, 3H), 4.22 (s, 2H), 8.42 (s, 1H), 9.97 (s, 1H)

実施例２実施例２−１〜２−２７に、本発明化合物の合成を記す。 Example 2 Synthesis of the compound of the present invention is described in Examples 2-1 to 2-27.

実施例２−１本発明化合物［化合物番号（２７ａ-1）］の合成
メタノール２ｍｌ及びピペリジン０．０２ｇの混合物に、3-アセチル-4-ヒドロキシ-1,6-ジメチル-2(1H)-ピリジノン０．１４ｇ及び5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒド０．１５ｇを溶解し、還流下に２時間３０分加熱した。室温に冷却後、反応液を濃縮してシリカゲルカラムクロマトグラフィーに付し、得られた結晶をヘキサンと酢酸エチルで再結晶し、4-ヒドロキシ-3-[3-[5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-イル]-1-オキソ-2-プロペニル]-1,6-ジメチル-2(1H)-ピリジノン［化合物番号（２７ａ-1）］の黄褐色結晶０．１３ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．４０（ｓ，３Ｈ），３．４９〜３．５５（ｍ, ４Ｈ），４．７０（ｓ，２Ｈ），６．０４（ｓ，１Ｈ），７．１０（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），７．４６（ｄ，１Ｈ，Ｊ＝３．８Ｈｚ），７．９６（ｄ，１Ｈ，Ｊ＝１５．１Ｈｚ），８．２８（ｄ，１Ｈ，Ｊ＝１５．４Ｈｚ），１３．７８（ｂｒｏａｄ，１Ｈ） Example 2-1 Synthesis of Compound of the Present Invention [Compound No. (27a-1)] To a mixture of 2 ml of methanol and 0.02 g of piperidine was added 3-acetyl-4-hydroxy-1,6-dimethyl-2 (1H) -pyridinone. 0.14 g and 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde 0.15 g were dissolved and heated under reflux for 2 hours 30 minutes. After cooling to room temperature, the reaction mixture was concentrated and subjected to silica gel column chromatography. The obtained crystals were recrystallized from hexane and ethyl acetate to give 4-hydroxy-3- [3- [5-[(2-hydroxy 0.13 g of yellowish brown crystals of [ethoxy) methyl] thiophen-2-yl] -1-oxo-2-propenyl] -1,6-dimethyl-2 (1H) -pyridinone [Compound No. (27a-1)] It was.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.40 (s, 3H), 3.49 to 3.55 (m, 4H), 4. 70 (s, 2H), 6.04 (s, 1H), 7.10 (d, 1H, J = 4.1 Hz), 7.46 (d, 1H, J = 3.8 Hz), 7.96 ( d, 1H, J = 15.1 Hz), 8.28 (d, 1H, J = 15.4 Hz), 13.78 (broad, 1H)

実施例２−２本発明化合物［化合物番号（３４ａ-1）］の合成
5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒドの代わりに、[(5-ホルミルチオフェン-2-イル)メチルチオ]酢酸メチル２．５６ｇを用いた以外は実施例２−１と同様にして、[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルチオ]酢酸メチル［化合物番号（３４ａ-1）］の黄褐色結晶１．２２ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．２９（ｓ，２Ｈ），３．４０（ｓ，３Ｈ），３．６３（ｓ，３Ｈ），４．１０（ｓ，２Ｈ），６．０４（ｓ，１Ｈ），７．０５（ｄ，１Ｈ，Ｊ＝３．８Ｈｚ），７．４３（ｄ，１Ｈ，Ｊ＝３．２Ｈｚ），７．９４（ｄ，１Ｈ，Ｊ＝１５．４Ｈｚ），８．２６（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），１６．２３（ｂｒｏａｄｓ，１Ｈ） Example 2-2 Synthesis of Compound of the Present Invention [Compound No. (34a-1)]
Example 2-1 except that 2.56 g of methyl [(5-formylthiophen-2-yl) methylthio] acetate was used instead of 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde Similarly, [[5- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophen-2-yl ] 1.22 g of yellow-brown crystals of [methylthio] acetic acid methyl [Compound No. (34a-1)] were obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.29 (s, 2H), 3.40 (s, 3H), 3.63 (s, 3H), 4.10 (s, 2H), 6.04 (s, 1H), 7.05 (d, 1H, J = 3.8 Hz), 7.43 (d, 1H, J = 3.2 Hz) 7.94 (d, 1H, J = 15.4 Hz), 8.26 (d, 1H, J = 15.7 Hz), 16.23 (broad s, 1H)

実施例２−３本発明化合物［化合物番号（３５ａ-1）］の合成
[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルチオ]酢酸メチル０．５１ｇの塩化メチレン１０ｍｌ溶液に、氷冷下にｍ−クロロ過安息香酸０．２４ｇを添加し、氷冷下に攪拌した。反応液を減圧濃縮し、酢酸エチルを加え、有機層を炭酸水素ナトリウム水と飽和食塩水で洗浄した後減圧濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルスルフィニル]酢酸メチル［化合物番号（３５ａ-1）］の黄色結晶０．２０ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．４０（ｓ，３Ｈ），３．７０（ｓ，３Ｈ），３．７３（ｄ，１Ｈ，Ｊ＝１２．４Ｈｚ），４．０２（ｄ，１Ｈ，Ｊ＝１４．３Ｈｚ），４．４３（ｄ，１Ｈ，Ｊ＝１３．８Ｈｚ），４．５９（ｄ，１Ｈ，Ｊ＝１３．８Ｈｚ），６．０４（ｓ，１Ｈ），７．１４（ｄ，１Ｈ，Ｊ＝３．５Ｈｚ），７．５３（ｄ，１Ｈ，Ｊ＝３．８Ｈｚ），７．９５（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），８．３１（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），１６．１８（ｓ，１Ｈ） Example 2-3 Synthesis of Compound of the Present Invention [Compound No. (35a-1)]
[[5- [3- (4-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophen-2-yl] methylthio] acetic acid To a solution of 0.51 g of methyl in 10 ml of methylene chloride was added 0.24 g of m-chloroperbenzoic acid under ice cooling, and the mixture was stirred under ice cooling. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added, the organic layer was washed with aqueous sodium hydrogen carbonate and saturated brine, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, [[5- [3- (4 -Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophen-2-yl] methylsulfinyl] acetate [Compound No. (35a-1) )] Yellow crystals 0.20 g was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.40 (s, 3H), 3.70 (s, 3H), 3.73 (d, 1H, J = 12.4 Hz), 4.02 (d, 1H, J = 14.3 Hz), 4.43 (d, 1H, J = 13.8 Hz), 4.59 (d, 1H, J = 13) .8 Hz), 6.04 (s, 1 H), 7.14 (d, 1 H, J = 3.5 Hz), 7.53 (d, 1 H, J = 3.8 Hz), 7.95 (d, 1 H) , J = 15.7 Hz), 8.31 (d, 1H, J = 15.7 Hz), 16.18 (s, 1H)

実施例２−４本発明化合物［化合物番号（３６ａ-1）］の合成
[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルチオ]酢酸メチル０．４９ｇの塩化メチレン１０ｍｌ溶液に、氷冷下にｍ−クロロ過安息香酸０．６０ｇを添加し、氷冷下に３時間攪拌した。反応液を実施例２−３と同様にして処理し、 [[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルスルホニル]酢酸メチル［化合物番号（３６ａ-1）］の黄色結晶０．２８ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４１（ｓ，３Ｈ），３．４０（ｓ，３Ｈ），３．７４（ｓ，３Ｈ），４．４４（ｓ，２Ｈ），５．００（ｓ，２Ｈ），６．０５（ｓ，１Ｈ），７．２２（ｄ，１Ｈ，Ｊ＝３．８Ｈｚ），７．５３（ｄ，１Ｈ，Ｊ＝３．５Ｈｚ），７．９６（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），８．３３（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），１６．１１（ｓ，１Ｈ） Example 2-4 Synthesis of the present compound [Compound No. (36a-1)]
[[5- [3- (4-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophen-2-yl] methylthio] acetic acid To a solution of 0.49 g of methyl in 10 ml of methylene chloride, 0.60 g of m-chloroperbenzoic acid was added under ice cooling, and the mixture was stirred for 3 hours under ice cooling. The reaction solution was treated in the same manner as in Example 2-3 to obtain [[5- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3- 0.28 g of yellow crystals of oxo-1-propenyl] thiophen-2-yl] methylsulfonyl] acetate [Compound No. (36a-1)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.41 (s, 3H), 3.40 (s, 3H), 3.74 (s, 3H), 4.44 (s, 2H), 5.00 (s, 2H), 6.05 (s, 1H), 7.22 (d, 1H, J = 3.8 Hz), 7.53 (d, 1H, J = 3.5 Hz) 7.96 (d, 1H, J = 15.7 Hz), 8.33 (d, 1H, J = 15.7 Hz), 16.11 (s, 1H)

実施例２−５本発明化合物［化合物番号（３７ａ-1）］の合成
[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルスルフィニル]酢酸メチル０．１７ｇのメタノール５ｍｌ溶液に、１規定水酸化ナトリウム水溶液５ｍｌを添加した。室温で攪拌し、溶媒を減圧留去して１０％塩酸で酸性とし、析出した結晶を濾取して乾燥することにより、[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルスルフィニル]酢酸［化合物番号（３７ａ-1）］の褐色結晶０．０９ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．４０（ｓ，３Ｈ），３．８８〜４．０４（２Ｈ），４．３６〜４．５８（２Ｈ），６．０４（ｓ，１Ｈ），７．１３（ｄ，１Ｈ，Ｊ＝３．５Ｈｚ），７．５３（ｄ，１Ｈ，Ｊ＝３．８Ｈｚ），７．９６（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），８．３２（ｄ，１Ｈ，Ｊ＝１５．４Ｈｚ），１６．１９（１Ｈ） Example 2-5 Synthesis of Compound of the Present Invention [Compound No. (37a-1)]
[[5- [3- (4-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophen-2-yl] methylsulfinyl] To a solution of 0.17 g of methyl acetate in 5 ml of methanol was added 5 ml of a 1N aqueous sodium hydroxide solution. The mixture was stirred at room temperature, the solvent was distilled off under reduced pressure, acidified with 10% hydrochloric acid, and the precipitated crystals were collected by filtration and dried to give [[5- [3- (4-hydroxy-1,6-dimethyl- 0.09 g of brown crystals of 2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophen-2-yl] methylsulfinyl] acetic acid [Compound No. (37a-1)] It was.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.40 (s, 3H), 3.88 to 4.04 (2H), 4.36 to 4.58 (2H), 6.04 (s, 1H), 7.13 (d, 1H, J = 3.5 Hz), 7.53 (d, 1H, J = 3.8 Hz), 7.96 ( d, 1H, J = 15.7 Hz), 8.32 (d, 1H, J = 15.4 Hz), 16.19 (1H)

実施例２−６本発明化合物［化合物番号（３８ａ-1）］の合成
[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルスルフィニル]酢酸メチルの代わりに、[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルスルホニル]酢酸メチル０．２２ｇを用いた以外は実施例２−５と同様にして、[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルスルホニル]酢酸［化合物番号（３８ａ-1）］の黄褐色結晶０．１８ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．４０（ｓ，３Ｈ），４．２８（ｓ，２Ｈ），４．９７（ｓ，２Ｈ），６．０５（ｓ，１Ｈ），７．２２（ｄ，１Ｈ，Ｊ＝３．５Ｈｚ），７．５３（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），７．９６（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），８．３３（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ） Example 2-6 Synthesis of the present compound [Compound No. (38a-1)]
[[5- [3- (4-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophen-2-yl] methylsulfinyl] Instead of methyl acetate, [[5- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophene-2 [[5- [3- (4-Hydroxy-1,6-dimethyl-2-oxo-1,2], except that 0.22 g of methyl -yl] methylsulfonyl] acetate was used 0.18 g of yellowish brown crystals of 2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophen-2-yl] methylsulfonyl] acetic acid [Compound No. (38a-1)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.40 (s, 3H), 4.28 (s, 2H), 4.97 (s, 2H), 6.05 (s, 1H), 7.22 (d, 1H, J = 3.5 Hz), 7.53 (d, 1H, J = 4.1 Hz), 7.96 (d, 1H, J = 15.7 Hz), 8.33 (d, 1H, J = 15.7 Hz)

実施例２−７本発明化合物［化合物番号（４０ａ-1）］の合成
5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒドの代わりに、N-(5-ホルミルチオフェン-2-イル)カルバミン酸2-メトキシエチル０．１５ｇを用い、メタノールの代わりに、エタノール３ｍｌを用いた以外は実施例２−１と同様にして、[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル] カルバミン酸2-メトキシエチル［化合物番号（４０ａ-1）］の赤色結晶０．１６ｇを得た。
¹Ｈ−ＮＭＲ（３００ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．３９（ｓ，３Ｈ），３．２９（ｓ，３Ｈ），３．４０（ｓ，３Ｈ），３．５８〜３．６０（２Ｈ），４．２７〜４．３０（２Ｈ），６．０５（ｓ，１Ｈ），６．５９（ｄ，１Ｈ，Ｊ＝３．９Ｈｚ），７．３７（ｄ，１Ｈ，Ｊ＝４．２Ｈｚ），７．９５（ｄ，１Ｈ，Ｊ＝１５．３Ｈｚ），８．１８（ｄ，１Ｈ，Ｊ＝１５．６Ｈｚ），１１．５１（ｂｒｏａｄ，１Ｈ），１６．５９（ｓ，１Ｈ） Example 2-7 Synthesis of Compound of the Present Invention [Compound No. (40a-1)]
Instead of methanol, instead of 0.15 g of 2-methoxyethyl N- (5-formylthiophen-2-yl) carbamate instead of 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde [5- [3- (4-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3] was prepared in the same manner as in Example 2-1, except that 3 ml of ethanol was used. -Oxo-1-propenyl] thiophen-2-yl] 0.16 g of red crystals of 2-methoxyethyl carbamate [Compound No. (40a-1)] was obtained.
¹ H-NMR (300 MHz, DMSO-d ₆ ) δ (ppm): 2.39 (s, 3H), 3.29 (s, 3H), 3.40 (s, 3H), 3.58-3. 60 (2H), 4.27 to 4.30 (2H), 6.05 (s, 1H), 6.59 (d, 1H, J = 3.9 Hz), 7.37 (d, 1H, J = 4.2 Hz), 7.95 (d, 1 H, J = 15.3 Hz), 8.18 (d, 1 H, J = 15.6 Hz), 11.51 (broad, 1 H), 16.59 (s, 1H)

実施例２−８本発明化合物［化合物番号（４６ａ-1）］の合成
5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒドの代わりに、N-(5-ホルミルチオフェン-2-イル)-2-メトキシアセトアミド０．１１ｇを用い、メタノールの代わりに、エタノール２ｍｌを用いた以外は実施例２−１と同様にして、4-ヒドロキシ-3-[3-[5-(メトキシアセチルアミノ)チオフェン-2-イル]-1-オキソ-2-プロペニル]-1,6-ジメチル-2(1H)-ピリジノン［化合物番号（４６ａ-1）］の赤褐色結晶０．１１ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．４０（ｓ，６Ｈ），４．１４（ｓ，２Ｈ），６．０１（ｓ，１Ｈ），６．９０（ｄ，１Ｈ，Ｊ＝３．８Ｈｚ），７．４０（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），７．９７（ｄ，１Ｈ，Ｊ＝１５．１Ｈｚ），８．２１（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ） Example 2-8 Synthesis of Compound of the Present Invention [Compound No. (46a-1)]
Instead of 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde, 0.11 g of N- (5-formylthiophen-2-yl) -2-methoxyacetamide was used, and ethanol was used instead of methanol. 4-Hydroxy-3- [3- [5- (5- (methoxyacetylamino) thiophen-2-yl] -1-oxo-2-propenyl] -1 in the same manner as in Example 2-1, except that 2 ml was used. , 6-Dimethyl-2 (1H) -pyridinone [Compound No. (46a-1)] 0.11 g of reddish brown crystals was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.40 (s, 6H), 4.14 (s, 2H), 6.01 (s, 1H), 6.90 (d, 1H, J = 3.8 Hz), 7.40 (d, 1H, J = 4.1 Hz), 7.97 (d, 1H, J = 15.1 Hz), 8. 21 (d, 1H, J = 15.7 Hz)

実施例２−９本発明化合物［化合物番号（５４ａ-1）］の合成
エタノール６ｍｌ及びピペリジン８４μｌの混合物に、3-アセチル-4-ヒドロキシ-1,6-ジメチル-2(1H)-ピリジノン４４０ｍｇ及び5-ホルミルチオフェン-2-カルボン酸 2-ヒドロキシエチルアミド５６９ｍｇを溶解し、還流下に５時間加熱した。室温に冷却後、析出した結晶を濾取してエタノール及びヘキサンで洗浄し、5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-カルボン酸 2-ヒドロキシエチルアミド［化合物番号（５４ａ-1）］の黄色結晶６７８ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．２４（ｓ，３Ｈ），３．２０〜３．４０（ｍ, ２Ｈ），３．４５〜３．５５（ｍ, ２Ｈ），４．７７（ｔ，１Ｈ，Ｊ＝５．４Ｈｚ），６．０５（ｓ，１Ｈ），７．５５（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），７．７６（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），７．９１（ｄ，１Ｈ，Ｊ＝１５．４Ｈｚ），８．３７（ｄ，１Ｈ，Ｊ＝１５．４Ｈｚ），８．６５（ｔ，１Ｈ，Ｊ＝５．４Ｈｚ），１５．９５（ｂｒｏａｄ，１Ｈ） Example 2-9 Synthesis of Compound of the Present Invention [Compound No. (54a-1)] To a mixture of 6 ml of ethanol and 84 μl of piperidine, 440 mg of 3-acetyl-4-hydroxy-1,6-dimethyl-2 (1H) -pyridinone and 569 mg of 5-formylthiophene-2-carboxylic acid 2-hydroxyethylamide was dissolved and heated under reflux for 5 hours. After cooling to room temperature, the precipitated crystals were collected by filtration and washed with ethanol and hexane to give 5- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) 678 mg of yellow crystals of 3-oxo-1-propenyl] thiophene-2-carboxylic acid 2-hydroxyethylamide [Compound No. (54a-1)] were obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.24 (s, 3H), 3.20 to 3.40 (m, 2H), 3. 45-3.55 (m, 2H), 4.77 (t, 1H, J = 5.4 Hz), 6.05 (s, 1H), 7.55 (d, 1H, J = 4.1 Hz), 7.76 (d, 1H, J = 14.1 Hz), 7.91 (d, 1H, J = 15.4 Hz), 8.37 (d, 1H, J = 15.4 Hz), 8.65 (t , 1H, J = 5.4 Hz), 15.95 (broad, 1H)

実施例２−１０本発明化合物［化合物番号（５６ａ-1）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-ヒドロキシエチルアミドの代わりに、5-ホルミルチオフェン-2-カルボン酸 2-メトキシエチルアミド０．３０ｇを用いた以外は実施例２−９と同様にして、5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-カルボン酸 2-メトキシエチルアミド［化合物番号（５６ａ-1）］の黄色結晶０．２７ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４１（ｓ，３Ｈ），３．２７（ｓ，３Ｈ），３．３０（ｓ，３Ｈ），３．４０〜３．５３（ｍ, ４Ｈ），６．０６（ｓ，１Ｈ），７．５６（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），７．７８（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），７．９３（ｄ，１Ｈ，Ｊ＝１６．９Ｈｚ），８．３８（ｄ，１Ｈ，Ｊ＝１６．９Ｈｚ），８．７４（ｔ，１Ｈ，Ｊ＝５．０Ｈｚ），１４．００（ｂｒｏａｄｓ，１Ｈ） Example 2-10 Synthesis of the present compound [Compound No. (56a-1)]
In the same manner as in Example 2-9, except that 0.30 g of 5-formylthiophene-2-carboxylic acid 2-methoxyethylamide was used instead of 5-formylthiophene-2-carboxylic acid 2-hydroxyethylamide, 5- [3- (4-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophene-2-carboxylic acid 2-methoxyethylamide 0.27 g of yellow crystals of [Compound No. (56a-1)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.41 (s, 3H), 3.27 (s, 3H), 3.30 (s, 3H), 3.40-3. 53 (m, 4H), 6.06 (s, 1H), 7.56 (d, 1H, J = 4.1 Hz), 7.78 (d, 1H, J = 4.1 Hz), 7.93 ( d, 1H, J = 16.9 Hz), 8.38 (d, 1H, J = 16.9 Hz), 8.74 (t, 1H, J = 5.0 Hz), 14.00 (broad s, 1H)

実施例２−１１本発明化合物［化合物番号（５８ａ-1）］の合成
5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒドの代わりに、5-ホルミルチオフェン-2-カルボン酸 N-(2-メトキシエチル)メチルアミド１５０ｍｇを用い、メタノールの代わりに、エタノールを用いた以外は実施例２−１と同様にして、[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル] カルボン酸 N-(2-メトキシエチル)メチルアミド［化合物番号（５８ａ-1）］の黄色結晶１１３ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．１４（３Ｈ），３．２７（ｓ，３Ｈ），３．４０（ｓ，３Ｈ），３．５５（ｔ，２Ｈ，Ｊ＝４．９Ｈｚ），３．６５（ｔ，２Ｈ，Ｊ＝４．９Ｈｚ），６．０５（ｓ，１Ｈ），７．５１（ｄ，１Ｈ，Ｊ＝４．１Ｈｚ），７．５４（ｄ，１Ｈ，Ｊ＝３．８Ｈｚ），７．９４（ｄ，１Ｈ，Ｊ＝１５．４Ｈｚ），８．３５（ｄ，１Ｈ，Ｊ＝１５．４Ｈｚ），１４．００（ｂｒｏａｄｓ，１Ｈ） Example 2-11 Synthesis of the compound of the present invention [Compound No. (58a-1)]
Instead of 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde, 150 mg of 5-formylthiophene-2-carboxylic acid N- (2-methoxyethyl) methylamide was used, and ethanol was used instead of methanol. [5- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-] was carried out in the same manner as in Example 2-1, except that it was used. 1-propenyl] thiophen-2-yl] carboxylic acid N- (2-methoxyethyl) methylamide [Compound No. (58a-1)] 113 mg of yellow crystals was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.14 (3H), 3.27 (s, 3H), 3.40 (s, 3H) 3.55 (t, 2H, J = 4.9 Hz), 3.65 (t, 2H, J = 4.9 Hz), 6.05 (s, 1H), 7.51 (d, 1H, J = 4.1 Hz), 7.54 (d, 1 H, J = 3.8 Hz), 7.94 (d, 1 H, J = 15.4 Hz), 8.35 (d, 1 H, J = 15.4 Hz), 14.00 (broad s, 1H)

実施例２−１２本発明化合物［化合物番号（６３ａ-1）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-ヒドロキシエチルアミドの代わりに、5-ホルミルチオフェン-2-カルボン酸カルバモイルメチルアミド１００ｍｇを用いた以外は実施例２−９と同様にして、5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-カルボン酸カルバモイルメチルアミド［化合物番号（６３ａ-1）］の黄色結晶７７．６ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４１（ｓ，３Ｈ），３．４０（ｓ，３Ｈ），３．４１（ｄ，１Ｈ，Ｊ＝５．９Ｈｚ），６．０５（ｓ，１Ｈ），７．０７（ｂｒｏａｄ，１Ｈ），７．４３（ｂｒｏａｄ，１Ｈ），７．５７（ｄ，１Ｈ，Ｊ＝４．０Ｈｚ），７．７９（ｄ，１Ｈ，Ｊ＝３．９Ｈｚ），７．９３（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），８．３９（ｄ，１Ｈ，Ｊ＝１５．４Ｈｚ），８．８８（ｔ，１Ｈ，Ｊ＝５．９Ｈｚ），１５．９７（ｂｒｏａｄ，１Ｈ） Example 2-12 Synthesis of the present compound [Compound No. (63a-1)]
5-formylthiophene-2-carboxylic acid In the same manner as in Example 2-9 except that 100 mg of 5-formylthiophene-2-carboxylic acid carbamoylmethylamide was used instead of 2-hydroxyethylamide, 5- [3 -(4-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophene-2-carboxylic acid carbamoylmethylamide [Compound No. (63a- 17.6] of yellow crystals was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.41 (s, 3H), 3.40 (s, 3H), 3.41 (d, 1H, J = 5.9 Hz), 6.05 (s, 1H), 7.07 (road, 1H), 7.43 (road, 1H), 7.57 (d, 1H, J = 4.0 Hz), 7.79 (d, 1H, J = 3.9 Hz), 7.93 (d, 1H, J = 15.7 Hz), 8.39 (d, 1H, J = 15.4 Hz), 8.88 (t, 1H, J = 5.9 Hz) ), 15.97 (broad, 1H)

実施例２−１３本発明化合物［化合物番号（７１ａ-1）］の合成
[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルスルフィニル]酢酸メチルの代わりに、[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルチオ]酢酸メチル０．１０ｇを用いた以外は実施例２−５と同様にして、[[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル]メチルチオ]酢酸［化合物番号（７１ａ-1）］の黄褐色結晶０．０９ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．２５（ｓ，２Ｈ），３．４０（ｓ，３Ｈ），４．１０（ｓ，２Ｈ），６．０４（ｓ，１Ｈ），７．０５（ｄ，１Ｈ，Ｊ＝３．８Ｈｚ），７．４３（ｄ，１Ｈ，Ｊ＝３．５Ｈｚ），７．９５（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），８．２６（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），１６．２４（ｓ，１Ｈ） Example 2-13 Synthesis of the compound of the present invention [Compound No. (71a-1)]
[[5- [3- (4-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophen-2-yl] methylsulfinyl] Instead of methyl acetate, [[5- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophene-2 [[5- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2] in the same manner as in Example 2-5, except that 0.10 g of methyl -yl] methylthio] acetate was used. 0.09 g of tan crystals of -dihydropyridin-3-yl) -3-oxo-1-propenyl] thiophen-2-yl] methylthio] acetic acid [Compound No. (71a-1)] were obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.25 (s, 2H), 3.40 (s, 3H), 4.10 (s, 2H), 6.04 (s, 1H), 7.05 (d, 1H, J = 3.8 Hz), 7.43 (d, 1H, J = 3.5 Hz), 7.95 (d, 1H, J = 15.7 Hz), 8.26 (d, 1H, J = 15.7 Hz), 16.24 (s, 1H)

実施例２−１４本発明化合物［化合物番号（７２ａ-1）］の合成
5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒドの代わりに、5-[N-(2-ジメチルアミノエチル)メチルアミノ]チオフェン-2-カルバルデヒド０．３２ｇを用い、メタノールの代わりに、エタノールを用いた以外は実施例２−１と同様にして、4-ヒドロキシ-3-[3-[5-[N-(2-ジメチルアミノエチル)メチルアミノ]チオフェン-2-イル]-1-オキソ-2-プロペニル]-1,6-ジメチル-2(1H)-ピリジノン［化合物番号（７２ａ-1）］の赤褐色結晶８０ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．１９（ｓ，６Ｈ），２．３６（ｓ，３Ｈ），２．４５〜２．５５（２Ｈ），３．０９（ｓ，３Ｈ），３．３６（ｓ，３Ｈ），３．５１（ｔ，２Ｈ，Ｊ＝８．１Ｈｚ），５．９２（ｓ，１Ｈ），６．０９（ｄ，１Ｈ，Ｊ＝５．４Ｈｚ），７．４０（ｄ，１Ｈ，Ｊ＝５．４Ｈｚ），７．８４（ｄ，１Ｈ，Ｊ＝１６．２Ｈｚ），７．９６（ｄ，１Ｈ，Ｊ＝１６．２Ｈｚ） Example 2-14 Synthesis of Compound of the Present Invention [Compound No. (72a-1)]
Instead of 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde, 0.32 g of 5- [N- (2-dimethylaminoethyl) methylamino] thiophene-2-carbaldehyde was used. Instead, 4-hydroxy-3- [3- [5- [N- (2-dimethylaminoethyl) methylamino] thiophen-2-yl] was prepared in the same manner as in Example 2-1, except that ethanol was used. 80 mg of reddish brown crystals of 1-oxo-2-propenyl] -1,6-dimethyl-2 (1H) -pyridinone [Compound No. (72a-1)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.19 (s, 6H), 2.36 (s, 3H), 2.45 to 2.55 (2H), 3.09 ( s, 3H), 3.36 (s, 3H), 3.51 (t, 2H, J = 8.1 Hz), 5.92 (s, 1H), 6.09 (d, 1H, J = 5. 4 Hz), 7.40 (d, 1 H, J = 5.4 Hz), 7.84 (d, 1 H, J = 16.2 Hz), 7.96 (d, 1 H, J = 16.2 Hz)

実施例２−１５本発明化合物［化合物番号（１０ａ-2）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-ヒドロキシエチルアミドの代わりに、5-ホルミルフラン-2-カルボン酸 2-メトキシエチルアミド０．５９ｇを用いた以外は実施例２−９と同様にして、5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]フラン-2-カルボン酸 2-メトキシエチルアミド［化合物番号（１０ａ-2）］の黄色結晶０．８２ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４１（ｓ，３Ｈ），３．２８（ｓ，３Ｈ），３．４１〜３．４７（ｍ, ７Ｈ），６．０５（ｓ，１Ｈ），７．１０（ｄ，１Ｈ，Ｊ＝３．６Ｈｚ），７．２６（ｄ，１Ｈ，Ｊ＝３．６Ｈｚ），７．６１（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），８．３５（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），８．６０（ｂｒｏａｄ，１Ｈ），１５．９５（ｂｒｏａｄｓ，１Ｈ） Example 2-15 Synthesis of the present compound [Compound No. (10a-2)]
In the same manner as in Example 2-9, except that 0.59 g of 5-formylfuran-2-carboxylic acid 2-methoxyethylamide was used instead of 5-formylthiophene-2-carboxylic acid 2-hydroxyethylamide, 5- [3- (4-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] furan-2-carboxylic acid 2-methoxyethylamide 0.82 g of yellow crystals of [Compound No. (10a-2)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.41 (s, 3H), 3.28 (s, 3H), 3.41 to 3.47 (m, 7H), 6. 05 (s, 1H), 7.10 (d, 1H, J = 3.6 Hz), 7.26 (d, 1H, J = 3.6 Hz), 7.61 (d, 1H, J = 15.7 Hz) ), 8.35 (d, 1H, J = 15.7 Hz), 8.60 (broad, 1H), 15.95 (broads, 1H)

実施例２−１６本発明化合物［化合物番号（１２ａ-2）］の合成
5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒドの代わりに、5-ホルミルフラン-2-カルボン酸 N-(2-メトキシエチル)メチルアミド１５０ｍｇを用い、メタノールの代わりに、エタノールを用いた以外は実施例２−１と同様にして、[5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]フラン-2-イル] カルボン酸 N-(2-メトキシエチル)メチルアミド［化合物番号（１２ａ-2）］の黄色結晶５７ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．０２（ｂｒｏａｄｓ，３Ｈ），３．２８（ｓ，３Ｈ），３．４０（ｓ，３Ｈ），３．５０〜３．７５（４Ｈ），６．０５（ｓ，１Ｈ），７．０９〜７．１５（２Ｈ），７．６３（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），８．３９（ｄ，１Ｈ，Ｊ＝１５．９Ｈｚ），１６．０４（ｓ，１Ｈ） Example 2-16 Synthesis of the present compound [compound number (12a-2)]
Instead of 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde, 150 mg of 5-formylfuran-2-carboxylic acid N- (2-methoxyethyl) methylamide was used, and ethanol was used instead of methanol. [5- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-] was carried out in the same manner as in Example 2-1, except that it was used. 1-propenyl] furan-2-yl] carboxylic acid N- (2-methoxyethyl) methylamide [Compound No. (12a-2)] (57 mg) was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.02 (broad s, 3H), 3.28 (s, 3H), 3.40 (s , 3H), 3.50 to 3.75 (4H), 6.05 (s, 1H), 7.09 to 7.15 (2H), 7.63 (d, 1H, J = 15.7 Hz), 8.39 (d, 1H, J = 15.9 Hz), 16.04 (s, 1H)

実施例２−１７本発明化合物［化合物番号（１ａ-3）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-ヒドロキシエチルアミドの代わりに、5-ホルミル-1-メチル-1H-ピロール-2-カルボン酸 2-メトキシエチルアミド１．１７ｇを用いた以外は実施例２−９と同様にして、5-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]-1-メチル-1H-ピロール-2-カルボン酸 2-メトキシエチルアミド［化合物番号（１ａ-3）］の黄色結晶０．７２ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．３９（ｓ，３Ｈ），３．２７（ｓ，３Ｈ），３．４１（ｓ，３Ｈ），３．４３〜３．４６（ｍ, ４Ｈ），３．９９（ｓ，３Ｈ），６．０２（ｓ，１Ｈ），６．７６（ｄ，１Ｈ，Ｊ＝４．３Ｈｚ），６．８６（ｄ，１Ｈ，Ｊ＝４．３Ｈｚ），７．８２（ｄ，１Ｈ，Ｊ＝１５．５Ｈｚ），８．２０（ｔ，１Ｈ，Ｊ＝４．８Ｈｚ），８．３７（ｄ，１Ｈ，Ｊ＝１５．５Ｈｚ） Example 2-17 Synthesis of Compound of the Present Invention [Compound No. (1a-3)]
Example 2 except that 1.17 g of 5-formyl-1-methyl-1H-pyrrole-2-carboxylic acid 2-methoxyethylamide was used instead of 5-formylthiophene-2-carboxylic acid 2-hydroxyethylamide In the same manner as -9, 5- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] -1-methyl 0.72 g of yellow crystals of -1H-pyrrole-2-carboxylic acid 2-methoxyethylamide [Compound No. (1a-3)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.39 (s, 3H), 3.27 (s, 3H), 3.41 (s, 3H), 3.43-3. 46 (m, 4H), 3.99 (s, 3H), 6.02 (s, 1H), 6.76 (d, 1H, J = 4.3 Hz), 6.86 (d, 1H, J = 4.3 Hz), 7.82 (d, 1 H, J = 15.5 Hz), 8.20 (t, 1 H, J = 4.8 Hz), 8.37 (d, 1 H, J = 15.5 Hz)

実施例２−１８本発明化合物［化合物番号（２ａ-3）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-ヒドロキシエチルアミドの代わりに、4-ホルミル-1-メチル-1H-ピロール-2-カルボン酸 2-メトキシエチルアミド３６１ｍｇを用いた以外は実施例２−９と同様にして、4-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]-1-メチル-1H-ピロール-2-カルボン酸 2-メトキシエチルアミド［化合物番号（２ａ-3）］の黄色結晶５０６ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．３９（ｓ，３Ｈ），３．２３（ｓ，３Ｈ），３．３３（ｓ，３Ｈ），３．８９（ｓ，３Ｈ），３．３０〜３．５０（ｍ, ４Ｈ），５．９９（ｓ，１Ｈ），７．２５（ｄ，１Ｈ，Ｊ＝１．９Ｈｚ），７．４６（ｄ，１Ｈ，Ｊ＝１．９Ｈｚ），７．７６（ｄ，１Ｈ，Ｊ＝１５．４Ｈｚ），８．２４（ｄ，１Ｈ，Ｊ＝１５．７Ｈｚ），８．３７（ｔ，１Ｈ，Ｊ＝５．４Ｈｚ），１６．７１（ｂｒｏａｄｓ，１Ｈ） Example 2-18 Synthesis of Compound of the Present Invention [Compound No. (2a-3)]
Example 2-9, except that 361 mg of 4-formyl-1-methyl-1H-pyrrole-2-carboxylic acid 2-methoxyethylamide was used instead of 5-formylthiophene-2-carboxylic acid 2-hydroxyethylamide 4- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3-oxo-1-propenyl] -1-methyl-1H 506 mg of yellow crystals of 2-pyrrole-2-carboxylic acid 2-methoxyethylamide [Compound No. (2a-3)] were obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.39 (s, 3H), 3.23 (s, 3H), 3.33 (s, 3H), 3.89 (s, 3H), 3.30 to 3.50 (m, 4H), 5.99 (s, 1H), 7.25 (d, 1H, J = 1.9 Hz), 7.46 (d, 1H, J = 1.9 Hz), 7.76 (d, 1 H, J = 15.4 Hz), 8.24 (d, 1 H, J = 15.7 Hz), 8.37 (t, 1 H, J = 5.4 Hz), 16.71 (broad s, 1H)

実施例２−１９本発明化合物［化合物番号（９ａ-3）］の合成
5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒドの代わりに、N-(5-ホルミルチアゾール-2-イル)-2-メトキシアセトアミド０．１５ｇを用い、メタノールの代わりに、エタノールを用いた以外は実施例２−１と同様にして、4-ヒドロキシ-3-[3-[2-(メトキシアセチルアミノ)チアゾール-5-イル]-1-オキソ-2-プロペニル]-1,6-ジメチル-2(1H)-ピリジノン［化合物番号（９ａ-3）］の黄色結晶０．１３ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．３７（ｓ，３Ｈ），３．４１（ｓ，３Ｈ），４．２１（ｓ，２Ｈ），６．０４（ｓ，１Ｈ），７．９８（ｓ，１Ｈ），８．０２（ｄ，１Ｈ，Ｊ＝１８．９Ｈｚ），８．２２（ｄ，１Ｈ，Ｊ＝１６．２Ｈｚ），１２．４９（ｂｒｏａｄｓ，１Ｈ），１６．２５（ｓ，１Ｈ） Example 2-19 Synthesis of Compound of the Present Invention [Compound No. (9a-3)]
Instead of 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde, 0.15 g of N- (5-formylthiazol-2-yl) -2-methoxyacetamide was used, and ethanol was used instead of methanol. 4-hydroxy-3- [3- [2- (methoxyacetylamino) thiazol-5-yl] -1-oxo-2-propenyl] -1, similar to Example 2-1, except that 0.13 g of yellow crystals of 6-dimethyl-2 (1H) -pyridinone [Compound No. (9a-3)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.37 (s, 3H), 3.41 (s, 3H), 4.21 (s, 2H), 6.04 (s, 1H), 7.98 (s, 1H), 8.02 (d, 1H, J = 18.9 Hz), 8.22 (d, 1H, J = 16.2 Hz) , 12.49 (broad s, 1H), 16.25 (s, 1H)

実施例２−２０本発明化合物［化合物番号（１０ａ-3）］の合成
5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒドの代わりに、N-(2-ホルミルチオフェン-4-イル)-2-メトキシアセトアミド０．１５ｇを用い、メタノールの代わりに、エタノール２ｍｌを用いた以外は実施例２−１と同様にして、4-ヒドロキシ-3-[3-[4-(メトキシアセチルアミノ)チオフェン-2-イル]-1-オキソ-2-プロペニル]-1,6-ジメチル-2(1H)-ピリジノン［化合物番号（１０ａ-3）］の黄褐色結晶０．２０ｇを得た。
¹Ｈ−ＮＭＲ（３００ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．３８（ｓ，３Ｈ），３．４０（ｓ，３Ｈ），４．０１（ｓ，２Ｈ），６．０４（ｓ，１Ｈ），７．６９（ｓ，１Ｈ），７．７９（ｓ，１Ｈ），７．９２（ｄ，１Ｈ，Ｊ＝１５．６Ｈｚ），８．３４（ｄ，１Ｈ，Ｊ＝１５．６Ｈｚ），１０．３４（ｓ，１Ｈ） Example 2-20 Synthesis of the present compound [Compound No. (10a-3)]
Instead of 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde, 0.15 g of N- (2-formylthiophen-4-yl) -2-methoxyacetamide was used, and ethanol was used instead of methanol. 4-hydroxy-3- [3- [4- (methoxyacetylamino) thiophen-2-yl] -1-oxo-2-propenyl] -1 in the same manner as in Example 2-1, except that 2 ml was used. , 6-Dimethyl-2 (1H) -pyridinone [Compound No. (10a-3)] 0.20 g of tan crystals were obtained.
¹ H-NMR (300 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.38 (s, 3H), 3.40 (s, 3H), 4.01 (s, 2H), 6.04 (s, 1H), 7.69 (s, 1H), 7.79 (s, 1H), 7.92 (d, 1H, J = 15.6 Hz), 8.34 (d , 1H, J = 15.6 Hz), 10.34 (s, 1H)

実施例２−２１本発明化合物［化合物番号（１１ａ-3）］の合成
5-[(2-ヒドロキシエトキシ)メチル]チオフェン-2-カルバルデヒドの代わりに、N-(2-ホルミルチオフェン-4-イル)カルバミン酸2-メトキシエチル０．１２ｇを用い、メタノールの代わりに、エタノール２ｍｌを用いた以外は実施例２−１と同様にして、[4-[3-(4-ヒドロキシ-1,6-ジメチル-2-オキソ-1,2-ジヒドロピリジン-3-イル)-3-オキソ-1-プロペニル]チオフェン-2-イル] カルバミン酸2-メトキシエチル［化合物番号（１１ａ-3）］の黄褐色結晶０．０９ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．４０（ｓ，３Ｈ），３．２８（ｓ，３Ｈ），３．３９（ｓ，３Ｈ），３．５６（ｔ，２Ｈ，Ｊ＝５．４Ｈｚ），４．２１（ｔ，２Ｈ，Ｊ＝５．４Ｈｚ），６．０４（ｓ，１Ｈ），７．３９（ｓ，１Ｈ），７．４４（ｓ，１Ｈ），７．９０（ｄ，１Ｈ，Ｊ＝１３．５Ｈｚ），８．３１（ｄ，１Ｈ，Ｊ＝１６．２Ｈｚ），１０．１６（ｂｒｏａｄ，１Ｈ），１６．１８（ｓ，１Ｈ） Example 2-21 Synthesis of the compound of the present invention [Compound No. (11a-3)]
Instead of 5-[(2-hydroxyethoxy) methyl] thiophene-2-carbaldehyde, 0.12 g of 2-methoxyethyl N- (2-formylthiophen-4-yl) carbamate was used, and instead of methanol, [4- [3- (4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl) -3] was prepared in the same manner as in Example 2-1, except that 2 ml of ethanol was used. -Oxo-1-propenyl] thiophen-2-yl] 0.09 g of tan crystals of 2-methoxyethyl carbamate [Compound No. (11a-3)] were obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.40 (s, 3H), 3.28 (s, 3H), 3.39 (s, 3H), 3.56 (t, 2H, J = 5.4 Hz), 4.21 (t, 2H, J = 5.4 Hz), 6.04 (s, 1H), 7.39 (s, 1H), 7.44 (s, 1H) 7.90 (d, 1H, J = 13.5 Hz), 8.31 (d, 1H, J = 16.2 Hz), 10.16 (road, 1H), 16.18 (s, 1H)

実施例２−２２本発明化合物［化合物番号（１０ｈ）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-メトキシエチルアミド０．１０ｇのエタノール３ｍｌ溶液に、3-アセチル-4-ヒドロキシ-1-メチル-1H-[1,8]ナフチリジン-2-オン０．１０ｇ及びピペリジン０．０１５ｍｌを加え、還流下に４時間加熱した。室温に冷却後、析出した結晶を濾取して酢酸エチル及びヘキサンで洗浄し、4-ヒドロキシ-1-メチル-3-[3-[5-[(2-メトキシエチル)アミノカルボニル]チオフェン-2-イル]アクリロイル]-1H-[1,8]ナフチリジン-2-オン［化合物番号（１０ｈ）］の黄褐色結晶０．１３ｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．２８（ｓ，３Ｈ），３．４１〜３．４８（ｍ，４Ｈ），３．６５（ｓ，３Ｈ），７．３５〜７．４２（１Ｈ），７．６３〜７．６５（１Ｈ），７．７９〜７．８１（１Ｈ），８．０８（ｄ，１Ｈ，Ｊ＝１５．９Ｈｚ），８．４１〜８．５１（１Ｈ），８．４７（ｄｄ，１Ｈ，Ｊ＝１．９，５．９Ｈｚ），８．７７〜８．７８（２Ｈ），１７．７５（ｂｒｏａｄ，１Ｈ） Example 2-22 Synthesis of the compound of the present invention [Compound No. (10h)]
3-Acetyl-4-hydroxy-1-methyl-1H- [1,8] naphthyridin-2-one 0.10 g in a solution of 5-formylthiophene-2-carboxylic acid 2-methoxyethylamide 0.10 g in ethanol 3 ml And piperidine (0.015 ml) were added, and the mixture was heated under reflux for 4 hours. After cooling to room temperature, the precipitated crystals were collected by filtration and washed with ethyl acetate and hexane to give 4-hydroxy-1-methyl-3- [3- [5-[(2-methoxyethyl) aminocarbonyl] thiophene-2. 0.13 g of tan crystals of -yl] acryloyl] -1H- [1,8] naphthyridin-2-one [Compound No. (10h)] were obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.28 (s, 3H), 3.41 to 3.48 (m, 4H), 3.65 (s, 3H), 7. 35-7.42 (1H), 7.63-7.65 (1H), 7.79-7.81 (1H), 8.08 (d, 1H, J = 15.9 Hz), 8.41- 8.51 (1H), 8.47 (dd, 1H, J = 1.9, 5.9 Hz), 8.77-8.78 (2H), 17.75 (broad, 1H)

実施例２−２３本発明化合物［化合物番号（１４ｈ）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-メトキシエチルアミド５００ｍｇのエタノール８ｍｌ溶液に、3-アセチル-4-ヒドロキシ-2-メチル-2H-1,2-ベンゾチアジン-1,1-ジオキシド５９３ｍｇ及びピペリジン６０ｍｇを加え、還流下に８時間加熱した。室温に冷却後、析出した結晶を濾取してメタノールで洗浄し、4-ヒドロキシ-3-[3-[5-[(2-メトキシエチル)アミノカルボニル]チオフェン-2-イル]アクリロイル]-2-メチル-2H-1,2-ベンゾチアジン-1,1-ジオキシド［化合物番号（１４ｈ）］の橙色結晶７７７ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．９５（ｓ，３Ｈ），３．２８（ｓ，３Ｈ），３．４１〜３．４６（ｍ，４Ｈ），７．１８（ｄ，１Ｈ，Ｊ＝１３．５Ｈｚ），７．７４〜７．７９（ｂｒｏａｄ，１Ｈ），７．８３（ｄ，１Ｈ，Ｊ＝２．７Ｈｚ），７．９３〜８．０６（ｍ，４Ｈ），８．１４〜８．１７（ｍ，１Ｈ），８．７４〜８．７９（ｍ，１Ｈ） Example 2-23 Synthesis of the compound of the present invention [Compound No. (14h)]
5-formylthiophene-2-carboxylic acid 2-methoxyethylamide 500 mg in ethanol 8 ml solution, 3-acetyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-1,1-dioxide 593 mg and piperidine 60 mg And heated under reflux for 8 hours. After cooling to room temperature, the precipitated crystals were collected by filtration and washed with methanol to give 4-hydroxy-3- [3- [5-[(2-methoxyethyl) aminocarbonyl] thiophen-2-yl] acryloyl] -2 There was obtained 777 mg of orange crystals of -methyl-2H-1,2-benzothiazine-1,1-dioxide [Compound No. (14h)].
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.95 (s, 3H), 3.28 (s, 3H), 3.41 to 3.46 (m, 4H), 7. 18 (d, 1H, J = 13.5 Hz), 7.74-7.79 (road, 1H), 7.83 (d, 1H, J = 2.7 Hz), 7.93-8.06 (m , 4H), 8.14 to 8.17 (m, 1H), 8.74 to 8.79 (m, 1H)

実施例２−２４本発明化合物［化合物番号（１ｉ）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-メトキシエチルアミドの代わりに、5-ホルミルチオフェン-2-カルボン酸 2-ヒドロキシエチルアミド１１１ｍｇを用いた以外は実施例２−２２と同様にして、4-ヒドロキシ-1-メチル-3-[3-[5-[(2-ヒドロキシエチル)アミノカルボニル]チオフェン-2-イル]アクリロイル]-1H-[1,8]ナフチリジン-2-オン［化合物番号（１ｉ）］の黄色結晶１５１ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．３２（ｑ，２Ｈ，Ｊ＝５．４Ｈｚ），３．４５〜３．５５（２Ｈ），３．６２（ｓ，３Ｈ），４．８５（ｂｒｏａｄ，１Ｈ），７．３５（ｄｄ，１Ｈ，Ｊ＝５．４，８．１Ｈｚ），７．６０（ｄ，１Ｈ，Ｊ＝２．７Ｈｚ），７．７７（ｄ，１Ｈ，Ｊ＝２．７Ｈｚ），８．０４（ｄ，１Ｈ，Ｊ＝１６．２Ｈｚ），８．３９（ｄ，１Ｈ，Ｊ＝１６．２Ｈｚ），８．４５〜８．５０（ｍ，１Ｈ），８．６８（ｔ，１Ｈ，Ｊ＝５．４Ｈｚ），８．７７〜８．８２（ｍ，１Ｈ） Example 2-24 Synthesis of Compound of the Present Invention [Compound No. (1i)]
4-Formylthiophene-2-carboxylic acid In the same manner as in Example 2-22 except that 111 mg of 5-formylthiophene-2-carboxylic acid 2-hydroxyethylamide was used instead of 2-methoxyethylamide, 4- Hydroxy-1-methyl-3- [3- [5-[(2-hydroxyethyl) aminocarbonyl] thiophen-2-yl] acryloyl] -1H- [1,8] naphthyridin-2-one [Compound No. (1i )] Yellow crystals of 151 mg were obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.32 (q, 2H, J = 5.4 Hz), 3.45 to 3.55 (2H), 3.62 (s, 3H) ), 4.85 (road, 1H), 7.35 (dd, 1H, J = 5.4, 8.1 Hz), 7.60 (d, 1H, J = 2.7 Hz), 7.77 (d , 1H, J = 2.7 Hz), 8.04 (d, 1H, J = 16.2 Hz), 8.39 (d, 1H, J = 16.2 Hz), 8.45-8.50 (m, 1H), 8.68 (t, 1H, J = 5.4 Hz), 8.77 to 8.82 (m, 1H)

実施例２−２５本発明化合物［化合物番号（２ｉ）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-メトキシエチルアミドの代わりに、N-(2-ホルミルチオフェン-4-イル)-2-メトキシアセトアミド１００ｍｇを用いた以外は実施例２−２２と同様にして、4-ヒドロキシ-1-メチル-3-[3-[4-(メトキシアセチルアミノ)チオフェン-2-イル]アクリロイル]-1H-[1,8]ナフチリジン-2-オン［化合物番号（２ｉ）］の黄褐色結晶１３１ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：３．３９（ｓ，３Ｈ），３．６４（ｓ，３Ｈ），４．０２（ｓ，２Ｈ），７．３６（ｄｄ，１Ｈ，Ｊ＝５．４，８．１Ｈｚ），７．７７（ｓ，１Ｈ），７．８６（ｓ，１Ｈ），８．０７（ｄ，１Ｈ，Ｊ＝１３．５Ｈｚ），８．３８（ｄ，１Ｈ，Ｊ＝１３．５Ｈｚ），８．４５〜８．５５（ｍ，１Ｈ），８．７５〜８．８５（ｍ，１Ｈ），１０．３７（ｂｒｏａｄ，１Ｈ） Example 2-25 Synthesis of the compound of the present invention [Compound No. (2i)]
5-formylthiophene-2-carboxylic acid In the same manner as in Example 2-22 except that 100 mg of N- (2-formylthiophen-4-yl) -2-methoxyacetamide was used instead of 2-methoxyethylamide. 4-hydroxy-1-methyl-3- [3- [4- (methoxyacetylamino) thiophen-2-yl] acryloyl] -1H- [1,8] naphthyridin-2-one [Compound No. (2i)] 131 mg of tan crystals were obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.39 (s, 3H), 3.64 (s, 3H), 4.02 (s, 2H), 7.36 (dd, 1H, J = 5.4, 8.1 Hz), 7.77 (s, 1H), 7.86 (s, 1H), 8.07 (d, 1H, J = 13.5 Hz), 8.38 ( d, 1H, J = 13.5 Hz), 8.45 to 8.55 (m, 1H), 8.75 to 8.85 (m, 1H), 10.37 (broad, 1H)

実施例２−２６本発明化合物［化合物番号（３ｉ）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-メトキシエチルアミドの代わりに、5-ホルミルチオフェン-2-カルボン酸 2-ヒドロキシエチルアミド３２９ｍｇを用いた以外は実施例２−２３と同様にして、4-ヒドロキシ-3-[3-[5-[(2-ヒドロキシエチル)アミノカルボニル]チオフェン-2-イル]アクリロイル]-2-メチル-2H-1,2-ベンゾチアジン-1,1-ジオキシド［化合物番号（３ｉ）］の橙色結晶３３０ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．９９（ｓ，３Ｈ），３．６０〜３．７０（ｍ，２Ｈ），３．８０〜３．９０（２Ｈ），６．５３（ｂｒｏａｄ，１Ｈ），７．１９（ｄ，１Ｈ，Ｊ＝１６．２Ｈｚ），７．３５（ｄ，１Ｈ，Ｊ＝２．７Ｈｚ），７．５０（ｄ，１Ｈ，Ｊ＝２．７Ｈｚ），７．８９（ｄ，１Ｈ，Ｊ＝１６．２Ｈｚ），７．７５〜７．８５（ｍ，２Ｈ），７．９０〜７．９５（ｍ，１Ｈ），８．１５〜８．２０（ｍ，１Ｈ） Example 2-26 Synthesis of the present compound [Compound No. (3i)]
In the same manner as in Example 2-23 except that 329 mg of 5-formylthiophene-2-carboxylic acid 2-hydroxyethylamide was used instead of 5-formylthiophene-2-carboxylic acid 2-methoxyethylamide, 4- Hydroxy-3- [3- [5-[(2-hydroxyethyl) aminocarbonyl] thiophen-2-yl] acryloyl] -2-methyl-2H-1,2-benzothiazine-1,1-dioxide [Compound No. ( 3i)] orange crystals (330 mg) were obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.99 (s, 3H), 3.60 to 3.70 (m, 2H), 3.80 to 3.90 (2H), 6.53 (broad, 1H), 7.19 (d, 1H, J = 16.2 Hz), 7.35 (d, 1H, J = 2.7 Hz), 7.50 (d, 1H, J = 2) .7 Hz), 7.89 (d, 1H, J = 16.2 Hz), 7.75-7.85 (m, 2H), 7.90-7.95 (m, 1H), 8.15-8 .20 (m, 1H)

実施例２−２７本発明化合物［化合物番号（４ｉ）］の合成
5-ホルミルチオフェン-2-カルボン酸 2-メトキシエチルアミドの代わりに、N-(2-ホルミルチオフェン-4-イル)-2-メトキシアセトアミド３００ｍｇを用いた以外は実施例２−２３と同様にして、4-ヒドロキシ-3-[3-[4-(メトキシアセチルアミノ)チオフェン-2-イル]アクリロイル]-2-メチル-2H-1,2-ベンゾチアジン-1,1-ジオキシド［化合物番号（４ｉ）］の橙色結晶５６０ｍｇを得た。
¹Ｈ−ＮＭＲ（２７０ＭＨｚ，ＤＭＳＯ-ｄ₆）δ（ｐｐｍ）：２．９３（ｓ，３Ｈ），３．３８（ｓ，３Ｈ），４．０２（ｓ，２Ｈ），７．０１（ｄ，１Ｈ，Ｊ＝１６．２Ｈｚ），７．８３（ｓ，１Ｈ），７．９０（ｓ，１Ｈ），７．９２〜８．００（ｍ，３Ｈ），８．０２（ｄ，１Ｈ，Ｊ＝１６．２Ｈｚ），８．１０〜８．１８（ｍ，１Ｈ） Example 2-27 Synthesis of Compound of the Present Invention [Compound No. (4i)]
5-formylthiophene-2-carboxylic acid In the same manner as in Example 2-23, except that 300 mg of N- (2-formylthiophen-4-yl) -2-methoxyacetamide was used instead of 2-methoxyethylamide. 4-hydroxy-3- [3- [4- (methoxyacetylamino) thiophen-2-yl] acryloyl] -2-methyl-2H-1,2-benzothiazine-1,1-dioxide [Compound No. (4i) Of 560 mg of orange crystals.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.93 (s, 3H), 3.38 (s, 3H), 4.02 (s, 2H), 7.01 (d, 1H, J = 16.2 Hz), 7.83 (s, 1H), 7.90 (s, 1H), 7.92 to 8.00 (m, 3H), 8.02 (d, 1H, J = 16.2 Hz), 8.10 to 8.18 (m, 1H)

実施例３（Ｉ型コラーゲン遺伝子の転写調節領域と結合されたレポーター遺伝子を有するプラスミドの調製）
正常ヒト胎児皮膚線維芽細胞（Ｃｌｏｎｔｅｃｈ社、カタログ番号ＣＣ−２５０９）１ｘ１０^８細胞を３７℃、５％ＣＯ₂雰囲気下で一晩培養した。培養された細胞をリン酸ナトリウム緩衝液（以下、ＰＢＳと記す。）で２回洗浄した後、ＰＢＳ３ｍｌを加えセルスクレイパー（Ｎａｌｇｅｎ、カタログ番号１７９６９３）を用いて細胞を器壁から剥がした。剥がされた細胞を遠心分離（１，５００ｒｐｍ、４℃、１５分間）により集め、これをＰＢＳ２０ｍｌに懸濁して再度遠心分離した。得られた沈殿に、ＤＮＡＥｘｔｒａｃｔｉｏｎＫｉｔ（Ｓｔｒａｔａｇｅｎｅ社、カタログ番号２００６００）のＳｏｌｕｔｉｏｎ２を１１ｍｌ、ｐｒｏｎａｓｅを４．８μｌそれぞれ加えて６０℃にて１時間振とうした後、得られた混合液を氷中に１０分間放置した。次に、当該混合液に上記キットのＳｏｌｕｔｉｏｎ３を４ｍｌ加えて混合した後、これを氷中に５分間放置した。遠心分離（３，０００ｒｐｍ、４℃、１５分間）し、上清を回収した。回収された上清に、当該上清１ｍｌ当たり２μｌのＲＮａｓｅを加え、３７℃で１５分間放置した。この混合液に、２倍容量のエタノールを加えて混合し、出現した白い糸状の物質（ゲノムＤＮＡ）を回収した。回収されたゲノムＤＮＡを７０％エタノールで洗浄した後、風乾した。風乾されたゲノムＤＮＡを１０ｍＭＴｒｉｓ−ＨＣｌ，１ｍＭＥＤＴＡ（ｐＨ８．０）（以下、ＴＥと記す。）５００μｌに溶解した。
得られたゲノムＤＮＡ溶解液（ゲノムＤＮＡ１μｇ相当量）と、配列番号１（配列番号１：コラーゲンプロモーターＤＮＡを増幅するために設計されたオリゴヌクレオチドプライマー：ccaagctagc gaaattatct tttctttcat ag 32）で示される塩基配列からなるオリゴヌクレオチド及び配列番号２（配列番号２：コラーゲンプロモーターＤＮＡを増幅するために設計されたオリゴヌクレオチドプライマー：ccaaaagctt gcagtcgtgg ccagtacc 28）で示される塩基配列からなるオリゴヌクレオチド（１０ｐｍｏｌ／μｌ）各１μｌ、蒸留水２９μｌ、ＴａＫａＲａＬＡＴａｑ（宝酒造社、カタログ番号ＲＲ００２Ａ）に添付されたｂｕｆｆｅｒ５μｌ、Ｍｇ²⁺溶液５μｌ、ｄＮＴＰｍｉｘｔｕｒｅ５μｌ及びＴａＫａＲａＬＡＴａｑ（宝酒造社、カタログ番号ＲＲ００２Ａ）０．５μｌを混合した。得られた混合液を９４℃、５分間保温した後、９４℃、１分間次いで６０℃、１分間さらに７２℃、１分間の保温を１サイクルとしてこれを３０サイクル行った。当該混合液を２％アガロースゲル電気泳動に供することにより、約０．５ｋｂのＤＮＡを回収した。回収されたＤＮＡをフェノール・クロロホルム処理した後、エタノール沈殿することによりＤＮＡを回収した。回収されたＤＮＡを超純水に溶解し、この溶解液にＮｈｅＩ２．５μｌ及びＨｉｎｄIII ２．５μｌを加え、３７℃で３時間保温した。次いで、当該溶解液を２％アガロースゲル電気泳動に供することにより、約３．５ｋｂのＤＮＡを回収した。回収されたＤＮＡをエタノール沈殿することにより再びＤＮＡ（以下、コラーゲンプロモーターＤＮＡと記す。）を回収した。
一方、ホタルルシフェラーゼをコードする塩基配列を有するベクターｐＧＬ３（Ｐｒｏｍｅｇａ社、カタログ番号Ｅ１７５１）をＮｈｅＩ及びＨｉｎｄIIIで消化した後、上記と同様にアガロースゲル電気泳動に供することにより、約５ｋｂのＤＮＡを回収した。回収されたＤＮＡをエタノール沈殿することにより再びＤＮＡを回収した。回収されたＤＮＡに蒸留水４４μｌ、ＡｌｋａｌｉｎｅＰｈｏｓｐｈａｔａｓｅ（宝酒造、カタログ番号２１２０Ａ）に添付されたＢｕｆｆｅｒ５μｌ及びＡｌｋａｌｉｎｅＰｈｏｓｐｈａｔａｓｅ（宝酒造社、カタログ番号２１２０Ａ）１μｌを加えて、この混合液を６５℃で３０分間保温した。次に、当該混合液を２回フェノール・クロロホルム処理した後、エタノール沈澱することによりＤＮＡ（以下、ＬｕｃベクターＤＮＡと記す。）を回収した。次いで、上記コラーゲンプロモーターＤＮＡ約２０ｎｇとＬｕｃベクターＤＮＡ約２０ｎｇとを混合した後、ＤＮＡＬｉｇａｔｉｏｎｋｉｔＶｅｒ２酵素溶液を同量添加して１６℃で一昼夜保温した。当該混合液に大腸菌５Ｈｄα（ＴＯＹＯＢＯ社、カタログ番号ＤＮＡ−９０３）を加えて氷中に３０分間放置し、次いで４２℃、４５秒間保温した後、得られた大腸菌を５０μｇ／ｍｌアンピシリンナトリウム（ナカライ社、カタログ番号０２７−３９）を含むＬＢプレートに播種し、３７℃、一昼夜放置した。出現したシングルコロニーを５０μｇ／ｍｌアンピシリンを含むＬＢ培地２ｍｌで３７℃、１２時間培養した。得られた培養液からＡＵＴＯＭＡＴＩＣＤＮＡＩＳＯＬＡＴＩＯＮＳＹＳＴＥＭＰＩ−５０（ＫＵＲＡＢＯ社）を用いてプラスミドＤＮＡを調製した。調製されたプラスミドＤＮＡの塩基配列をＤＮＡシークエンサーで分析した。その結果、当該プラスミド（以下、ＣＯＬ−Ｌｕｃと記す。）は、ヒト由来のＩ型コラーゲンα２鎖遺伝子の転写調節領域の−３５００〜＋５７（転写開始点を＋１とする。）の塩基配列の下流に、レポーター遺伝子としてホタルルシフェラーゼのアミノ酸配列をコードする塩基配列が接続されてなる塩基配列を保有していることが確認された。 Example 3 (Preparation of plasmid having reporter gene linked to transcriptional regulatory region of type I collagen gene)
Normal human fetal skin fibroblasts (Clontech, catalog number CC-2509) 1 × 10 ⁸ cells were cultured overnight at 37 ° C. in a 5% CO ₂ atmosphere. The cultured cells were washed twice with a sodium phosphate buffer (hereinafter referred to as PBS), 3 ml of PBS was added, and the cells were detached from the vessel wall using a cell scraper (Nalgen, catalog number 179963). The detached cells were collected by centrifugation (1,500 rpm, 4 ° C., 15 minutes), suspended in 20 ml of PBS, and centrifuged again. To the obtained precipitate, 11 ml of Solution 2 of DNA Extraction Kit (Stratagene, Catalog No. 200600) and 4.8 μl of pronase were added and shaken at 60 ° C. for 1 hour, and the resulting mixture was put in ice. Left for 10 minutes. Next, 4 ml of Solution 3 from the above kit was added to the mixture and mixed, and the mixture was left on ice for 5 minutes. Centrifugation (3,000 rpm, 4 ° C., 15 minutes) was performed, and the supernatant was collected. To the collected supernatant, 2 μl of RNase per 1 ml of the supernatant was added and left at 37 ° C. for 15 minutes. To this mixture, 2 volumes of ethanol was added and mixed, and the white filamentous material (genomic DNA) that appeared was recovered. The collected genomic DNA was washed with 70% ethanol and then air-dried. The air-dried genomic DNA was dissolved in 500 μl of 10 mM Tris-HCl, 1 mM EDTA (pH 8.0) (hereinafter referred to as TE).
The nucleotide sequence shown by the resulting genomic DNA lysate (equivalent to 1 μg of genomic DNA) and SEQ ID NO: 1 (SEQ ID NO: 1: oligonucleotide primer designed for amplifying collagen promoter DNA: ccaagctagc gaaattatct tttctttcat ag 32) 1 μl each of oligonucleotides consisting of the nucleotide sequence shown in SEQ ID NO: 2 and SEQ ID NO: 2 (SEQ ID NO: 2 oligonucleotide primer designed to amplify collagen promoter DNA: ccaaaagctt gcagtcgtgg ccagtacc 28), 10 pmol / μl, distilled water 29 [mu] l, TaKaRa LA Taq (Takara Shuzo, catalog No. RR002A) in the appended buffer 5 [mu] l, Mg ²⁺ solution 5 [mu] l, dNTPs Mixture 5 [mu] l and TaKaRa LA Taq (Takara Shuzo, catalog No. RR002 ) Was mixed with 0.5μl. The obtained mixed solution was kept at 94 ° C. for 5 minutes, and then kept at 94 ° C., 1 minute, then 60 ° C., 1 minute, further 72 ° C., and 1 minute, and this was repeated for 30 cycles. The mixture was subjected to 2% agarose gel electrophoresis to recover about 0.5 kb of DNA. The recovered DNA was treated with phenol / chloroform and then precipitated with ethanol to recover the DNA. The recovered DNA was dissolved in ultrapure water, and 2.5 μl of NheI and 2.5 μl of HindIII were added to this lysate and incubated at 37 ° C. for 3 hours. Next, the lysate was subjected to 2% agarose gel electrophoresis to recover about 3.5 kb of DNA. The recovered DNA was ethanol precipitated to recover DNA (hereinafter referred to as collagen promoter DNA) again.
On the other hand, a vector pGL3 (Promega, catalog number E1751) having a base sequence encoding firefly luciferase was digested with NheI and HindIII, and then subjected to agarose gel electrophoresis in the same manner as above to recover about 5 kb of DNA. . DNA was recovered again by ethanol precipitation of the recovered DNA. 44 μl of distilled water, 5 μl of Buffer attached to Alkaline Phosphatase (Takara Shuzo, catalog number 2120A) and 1 μl of Alkaline Phosphatase (Takara Shuzo, catalog number 2120A) were added to the recovered DNA, and this mixture was incubated at 65 ° C. for 30 minutes. . Next, the mixed solution was treated twice with phenol / chloroform and then precipitated with ethanol to recover DNA (hereinafter referred to as Luc vector DNA). Next, about 20 ng of the collagen promoter DNA and about 20 ng of the Luc vector DNA were mixed, the same amount of the DNA Ligation Kit Ver2 enzyme solution was added, and the mixture was kept at 16 ° C. overnight. Escherichia coli 5Hdα (TOYOBO, catalog number DNA-903) was added to the mixed solution, left on ice for 30 minutes, and then incubated at 42 ° C. for 45 seconds. Then, the obtained Escherichia coli was 50 μg / ml ampicillin sodium (Nacalai). LB plate containing catalog number 027-39) and left at 37 ° C. overnight. The appearing single colony was cultured at 37 ° C. for 12 hours in 2 ml of LB medium containing 50 μg / ml ampicillin. Plasmid DNA was prepared from the obtained culture solution using AUTOMATIC DNA ISOLATION SYSTEM PI-50 (KURABO). The nucleotide sequence of the prepared plasmid DNA was analyzed with a DNA sequencer. As a result, the plasmid (hereinafter referred to as COL-Luc) is downstream of the base sequence of −3500 to +57 (transcription start point is +1) of the transcriptional regulatory region of human type I collagen α2 chain gene. In addition, it was confirmed that a reporter gene possesses a base sequence connected to a base sequence encoding the amino acid sequence of firefly luciferase.

実施例４（レポーター遺伝子の発現量を指標とした被験化合物が有するＩ型コラーゲン遺伝子の転写調節能力の測定）
正常ヒト胎児皮膚線維芽細胞１ｘ１０⁶細胞を１００ｍｍディッシュに播種し、非働化牛胎児血清（以下、ＦＢＳと記す。Ｇｉｂｃｏ社、カタログ番号２１１４０−０７９）を１０（ｖ／ｖ）％含むＤｕｌｂｅｃｃｏ’ｓ−ＭＥＭ（日水製薬社、カタログ番号０５９１９）培地（以下、当該培地をＤ−ＭＥＭ（＋）と記す。）中で３７℃、５％ＣＯ₂雰囲気下において一晩培養した。次いで培地を、ＦＢＳを含まないＤｕｌｂｅｃｃｏ’ｓ−ＭＥＭ培地（以下、当該培地をＤ−ＭＥＭ（−）と記す。）に置換した。
Ｄ−ＭＥＭ（−）３００μｌに、ＣＯＬ−Ｌｕｃ５μｇ及びｐＣＭＶ−β−ｇａｌ（Ｉｎｖｉｔｒｏｇｅｎ社、カタログ番号１０５８６−０１４）５μｇを加え、得られた混合液を室温で５分間放置した（溶液１）。また、Ｄ−ＭＥＭ（−）３００μｌにＬｉｐｏｆｅｃｔｉｎｅ（Ｇｉｂｃｏ社、カタログ番号１８２９２−０１１）２０μｌを加え、得られた混合液を室温で４５分間放置した（溶液２）。次に、溶液１と溶液２とを混合し、これを室温で１０分間放置した後、当該混合液にＤ−ＭＥＭ（−）５．４ｍｌを加えて混合した。当該混合液を前記正常ヒト胎児皮膚線維芽細胞に添加した後、当該細胞を３７℃、５％ＣＯ₂雰囲気下で培養した。６時間後、ディッシュから培養上清を除き、細胞をＰＢＳで２回洗浄した後、ディッシュに０．２５％トリプシンを含むＰＢＳ１ｍｌを添加してディッシュから細胞を剥がした。剥がされた細胞にＤ−ＭＥＭ（＋）を加えてよく混合した後、当該混合物を１２ウエルプレートに１ｍｌずつ分注し、これを３７℃、５％ＣＯ₂雰囲気下で終夜培養した。翌日、各ウエルをＤ−ＭＥＭ（−）で２回洗浄した後、０．１％ＦＢＳを含むＤｕｌｂｅｃｃｏ’ｓ−ＭＥＭ培地（以下、当該培地をＤ−ＭＥＭ（０．１％）と記す。）１ｍｌに置換した。
このようにして培養された細胞に、化合物番号（３４ａ-1）、（５４ａ-1）、（５６ａ-1）、（７１ａ-1）、（１０ａ-3）、（１ｉ）及び（３ｉ）で示される本発明化合物が１ｍＭになるよう１０％ジメチルスルホキシド（以下、ＤＭＳＯと記す。）で溶解し、その溶液を１０μｌ添加した（本発明化合物最終濃度１０μＭ、ＤＭＳＯ最終濃度０．１％）。また、化合物番号（１４ｈ）で示される本発明化合物が０．３ｍＭになるよう１０％ジメチルスルホキシド（以下、ＤＭＳＯと記す。）で溶解し、その溶液を１０μｌ添加した（本発明化合物最終濃度３μＭ、ＤＭＳＯ最終濃度０．１％）。尚、対照では１０％ＤＭＳＯを１０μｌ添加した。
１時間後、ＴＧＦ−β（ＰｅｐｒｏＴｅｃｈ社）の０．５μｇ／ｍｌ水溶液又は蒸留水を１０μｌ添加し、３７℃、５％ＣＯ₂雰囲気下でさらに４０時間培養した。培養された細胞をＰＢＳで２回洗浄した後、これに細胞溶解剤（東洋インキ社、カタログ番号ＰＤ１０）２００μｌを加え細胞を剥がした。剥がされた細胞を細胞懸濁液として回収した後、これを遠心分離（１５，０００ｒｐｍ、４℃、５分間）することにより、上清を回収した。回収された上清各５０μｌを９６ウエルプレートに移した後、ＭＩＣＲＯＬＵＭＡＴＬＢ９６Ｐ（ＥＧ＆ＧＢＥＲＴＨＯＬＤ社製）を用いて、Ｌｕｃアッセイ溶液（２０ｍＭＴｒｉｃｉｎｅ（ｐＨ７．８）、２．６７ｍＭＭｇＳＯ_４、０．１ｍＭＥＤＴＡ、３３．３ｍＭＤＴＴ、２７０μＭＣｏｅｎｚｙｍｅＡ、５３０μＭＡＴＰ、４７０μＭＬｕｃｉｆｅｒｉｎ）５０μｌを当該プレートに自動分注した後、各ウエル内の発光量を測定した（Ｄｅｌａｙ：１．６秒、Ｍｅａｓ．Ｉｎｔｅｒｖａｌ：２０秒）。
一方、回収された上清又は細胞溶解剤５０μｌを、予め９６ウエルプレートに分注されたβ−ｇａｌ基質溶液（５．８ｍＭｏ−ｎｉｔｒｏｐｈｅｎｙｌ−ｂｅｔａ−Ｄ−ｇａｌａｃｔｏｐｙｒａｎｏｓｉｄｅ、１ｍＭＭｇＣｌ_２、４５ｍＭ２−メルカプトエタノール）５０μｌに加えて３７℃、２時間インキュベートした後、マイクロプレートリーダーを用いて各ウエル内の４２０ｎｍの吸光度を測定した。得られた値を基にし、次式に従って転写活性を算出した。
転写活性＝［発光量（上清添加区）−発光量（細胞溶解剤添加区）］／［４２０ｎｍ吸光度（上清添加区）−４２０ｎｍ吸光度（細胞溶解剤添加区）］
次に、算出された転写活性を基にし、次式に従って、ＴＧＦ−βが有するＩ型コラーゲン遺伝子の転写促進能力に対する被験化合物の阻害効果を阻害度として算出した。
阻害度＝［転写活性（ＤＭＳＯ及びＴＧＦ−β添加試験区）−転写活性（化合物及びＴＧＦ−β添加試験区）］／［転写活性（ＤＭＳＯ及びＴＧＦ−β添加試験区）−転写活性（ＤＭＳＯ及びＴＧＦ−β無添加試験区）］×１００
化合物番号（３４ａ-1）、（５４ａ-1）、（５６ａ-1）、（７１ａ-1）、（１０ａ-3）、（１ｉ）及び（３ｉ）で示される本発明化合物が本発明化合物最終濃度１０μＭにおいて、化合物番号（１４ｈ）で示される本発明化合物が本発明化合物最終濃度３μＭにおいて、阻害度は、７０以上であった。本発明化合物が、ＴＧＦ−βが有するＩ型コラーゲン遺伝子の転写促進能力を阻害し、Ｉ型コラーゲン遺伝子の転写を抑制する能力を有することが確認された。 Example 4 (Measurement of transcriptional regulatory ability of type I collagen gene of test compound using reporter gene expression level as index)
Normal human fetal skin fibroblasts 1 × 10 ⁶ cells were seeded in a 100 mm dish, and Dulbecco's containing 10 (v / v)% inactivated fetal bovine serum (hereinafter referred to as FBS, Gibco, catalog number 21140-079). -Cultured overnight in a MEM (Nissui Pharmaceutical Co., Ltd., Catalog No. 05919) medium (hereinafter, the medium is referred to as D-MEM (+)) at 37 ° C in a 5% CO ₂ atmosphere. Next, the medium was replaced with Dulbecco's-MEM medium not containing FBS (hereinafter, the medium is referred to as D-MEM (−)).
To 300 μl of D-MEM (−), 5 μg of COL-Luc and 5 μg of pCMV-β-gal (Invitrogen, catalog number 10586-014) were added, and the resulting mixture was allowed to stand at room temperature for 5 minutes (Solution 1). Moreover, 20 microliters of Lipofectine (Gibco, catalog number 18292-011) was added to 300 microliters of D-MEM (-), and the obtained liquid mixture was left for 45 minutes at room temperature (solution 2). Next, Solution 1 and Solution 2 were mixed and allowed to stand at room temperature for 10 minutes, and then 5.4 ml of D-MEM (−) was added to the mixture and mixed. After the mixture was added to the normal human fetal skin fibroblasts, the cells were cultured at 37 ° C. in a 5% CO ₂ atmosphere. After 6 hours, the culture supernatant was removed from the dish, and the cells were washed twice with PBS. Then, 1 ml of PBS containing 0.25% trypsin was added to the dish, and the cells were detached from the dish. After D-MEM (+) was added to the detached cells and mixed well, 1 ml of the mixture was dispensed into a 12-well plate and cultured overnight at 37 ° C. in a 5% CO ₂ atmosphere. The next day, each well was washed twice with D-MEM (−), and then Dulbecco's-MEM medium containing 0.1% FBS (hereinafter, the medium is referred to as D-MEM (0.1%)). Replaced with 1 ml.
The cells cultured in this manner were subjected to compound numbers (34a-1), (54a-1), (56a-1), (71a-1), (10a-3), (1i) and (3i). The indicated compound of the present invention was dissolved in 10% dimethyl sulfoxide (hereinafter referred to as DMSO) so as to be 1 mM, and 10 μl of the solution was added (final compound concentration of the present compound of 10 μM, DMSO final concentration of 0.1%). Further, the compound of the present invention represented by the compound number (14h) was dissolved in 10% dimethyl sulfoxide (hereinafter referred to as DMSO) so as to be 0.3 mM, and 10 μl of the solution was added (final concentration of the compound of the present invention of 3 μM, DMSO final concentration 0.1%). As a control, 10 μl of 10% DMSO was added.
One hour later, 10 μl of a 0.5 μg / ml aqueous solution of TGF-β (Pepro Tech) or distilled water was added, and the cells were further cultured at 37 ° C. in a 5% CO ₂ atmosphere for 40 hours. The cultured cells were washed twice with PBS, and then 200 μl of a cell lysing agent (Toyo Ink, Catalog No. PD10) was added to peel the cells. After the peeled cells were collected as a cell suspension, the supernatant was collected by centrifuging (15,000 rpm, 4 ° C., 5 minutes). 50 μl of each collected supernatant was transferred to a 96-well plate, and then a Luc assay solution (20 mM Tricine (pH 7.8), 2.67 mM MgSO ₄ , 0.1 mM EDTA using MICROLUMAT LB96P (EG & G BERTHOLD). , 33.3 mM DTT, 270 μM Coenzyme A, 530 μMATP, 470 μM Luciferin) was automatically dispensed on the plate, and the amount of luminescence in each well was measured (Delay: 1.6 seconds, Meas. Interval: 20 seconds) .
On the other hand, 50 μl of the collected supernatant or cell lysing agent was added to a β-gal substrate solution (5.8 mM o-nitrophenyl-beta-D-galactopyranoside, 1 mM MgCl ₂ , 45 mM 2-mercapto previously dispensed in a 96-well plate. Ethanol) was added to 50 μl and incubated at 37 ° C. for 2 hours, and then the absorbance at 420 nm in each well was measured using a microplate reader. Based on the obtained value, the transcription activity was calculated according to the following formula.
Transcriptional activity = [Luminescence (supernatant addition) -Luminescence (cell lysate addition)] / [420 nm absorbance (supernatant addition) -420 nm absorbance (cell lysate addition)]
Next, based on the calculated transcription activity, the inhibitory effect of the test compound on the ability of TGF-β to promote transcription of type I collagen gene was calculated as the degree of inhibition according to the following formula.
Degree of inhibition = [transcriptional activity (DMSO and TGF-β addition test group) −transcription activity (compound and TGF-β addition test group)] / [transcription activity (DMSO and TGF-β addition test group) −transcription activity (DMSO and TGF-β-free test section)] × 100
The compound of the present invention represented by compound numbers (34a-1), (54a-1), (56a-1), (71a-1), (10a-3), (1i) and (3i) is the final compound of the present invention. At a concentration of 10 μM, the compound of the present invention represented by compound number (14h) had a degree of inhibition of 70 or more at a final concentration of 3 μM of the compound of the present invention. It was confirmed that the compound of the present invention has the ability to inhibit the type I collagen gene transcription promoting ability of TGF-β and to suppress the type I collagen gene transcription.

実施例５（フィブロネクチンの発現量を指標とした被験化合物が有するＴＧＦ−β抑制能力の測定）
正常ヒト皮膚線維芽細胞（Ｃｌｏｎｅｔｉｃｓ社、カタログ番号ＣＣ−２５０９）５ｘ１０^３個／ウエルを、９６ウエルプレート（ＢＥＣＴＯＮＤＩＣＫＩＮＳＯＮ社、カタログ番号３５−３０７５）に播き、３７℃、５％ CO2下のインキュベーターで一晩培養した。翌日、０．１％牛胎児血清を含むＤ−ＭＥＭ培地（日水製薬（株）社、コード番号０５９１９）０．１ｍｌに交換した。その１時間後、化合物番号（２ａ-3）で示される本発明化合物を最終濃度１０μＭになるように添加し、また、化合物番号（６３ａ-1）で示される本発明化合物を最終濃度３μＭになるように添加し、１時間培養した後に、最終濃度５ｎｇ／ｍｌのＴＧＦ−β（Ｐｅｐｒｏｔｅｃｈ社、カタログ番号１００−２１Ｒ）を添加し、さらに２６時間培養した。リン酸緩衝液で２回洗浄した後に、ＳＶ９６ＴｏｔａｌＲＮＡＩｓｏｌａｔｉｏｎＳｙｓｔｅｍ（Ｐｒｏｍｅｇａ社、カタログ番号Ｚ３５０５）を用いて全ＲＮＡを分離した。分離された全ＲＮＡ５μｌに、２０μＭオリゴｄＴ１μｌ及びＲＮａｓｅフリー蒸留水４μｌを加えて６５℃、５分間インキュベートし、直ぐに氷冷した。当該溶液１０μｌに、５×バッファー４μｌ、ＭｇＣｌ_２２．４μｌ、１０ｍＭｄＮＴＰ１μｌ、ＲＮａｓｉｎ１μｌ、ＩｍｐｒｏｍII １μｌ、ＲＮａｓｅフリー蒸留水０．６μｌ（以上、全てＰｒｏｍｅｇａ社）を加えて２５℃ ５分間、４２℃ １時間、７０℃ １５分間の条件で逆転写反応した。
逆転写反応溶液５μｌに、配列番号３（配列番号３：フィブロネクチン遺伝子のＤＮＡを検出するために、ＰＣＲ用プライマーとして設計されたオリゴヌクレオチド：tcgccatcag tagaaggtag ca 22）、配列番号４（配列番号４：フィブロネクチン遺伝子のＤＮＡを検出するために、ＰＣＲ用プライマーとして設計されたオリゴヌクレオチド：tatactgaac accaggttgc aagtc 25）で示される各２０ｐｍｏｌ／μｌのプライマー１μｌ及び配列番号５（配列番号５：フィブロネクチン遺伝子のＤＮＡを検出するために、プローブとして設計されたオリゴヌクレオチド：ctcaaccttc ctgaaactgc aaactccgtc 30）で示されるフィブロネクチン遺伝子のＤＮＡ検出用プローブ１．２５μｌ、又はＨｕｍａｎＧＡＰＤＨプラーマー・プローブ（ＡｐｐｌｉｅｄＢｉｏｓｙｓｔｅｍｓ社、カタログ番号４３１０８８４Ｅ）１．２５μｌを加え、ＴａｑＭａｎＵｎｉｖｅｒｓａｌＰＣＲＭａｓｔｅｒＭｉｘ（ＡｐｐｌｉｅｄＢｉｏｓｙｓｔｅｍｓ社、カタログ番号４３０４４３７）１２．５μｌ及び滅菌水を加えて５０μｌに調整し、Ｏｐｔｉｃａｌ９６−ＷｅｌｌＲｅａｃｔｉｏｎＰｌａｔｅ（ＡｐｐｌｉｅｄＢｉｏｓｙｓｔｅｍｓ社、カタログ番号Ｎ８０１−０５６０）のウエル中で混合した。スタンダードは、ＴＧＦ−βのみを添加した細胞から全ＲＮＡを調製し、その２５０、１２５、６２．５、３１．２５、１５．６２５、７．８１２５ｎｇをそれぞれ逆転写反応したｃＤＮＡ溶液を用いた。その後、ＧｅｎｅＡｍｐ７９００（ＡｐｐｌｉｅｄＢｉｏｓｙｓｔｅｍｓ社）を用いて５０℃ ５分間１サイクル、９５℃ １５秒間及び６０℃ １分間の４０サイクルの条件でＰＣＲした。定量は各スタンダード直線を作成した後、フィブロネクチン量及びＧＡＰＤＨ量をそれぞれ算出し、次式に従って転写量を算出した。
フィブロネクチン転写量＝フィブロネクチン量／ＧＡＰＤＨ量
阻害度＝［転写量（DMSO及びＴＧＦ−β添加試験区）−転写量（化合物及びＴＧＦ−β添加試験区）］／［転写量（DMSO及びＴＧＦ−β添加試験区）−転写量（DMSO及びＴＧＦ−β無添加試験区）］ｘ１００
化合物番号（２ａ-3）及び（６３ａ-1）で示される本発明化合物の阻害度は、７０％以上であった。
本発明化合物が、ＴＧＦ−βによって促進される皮膚線維芽細胞のフィブロネクチン遺伝子の転写量を抑制することが確認された。 Example 5 (Measurement of TGF-β inhibitory ability of test compound having fibronectin expression level as index)
Normal human dermal fibroblasts (Clonetics, catalog number CC-2509) 5 × 10 ³ cells / well are seeded in a 96-well plate (BECTON DICKINSON, catalog number 35-3075) in an incubator at 37 ° C. under 5% CO 2. Incubated overnight. The next day, the medium was replaced with 0.1 ml of D-MEM medium (Nissui Pharmaceutical Co., Ltd., code number 05919) containing 0.1% fetal bovine serum. One hour later, the compound of the present invention represented by compound number (2a-3) was added to a final concentration of 10 μM, and the compound of the present invention represented by compound number (63a-1) was added to a final concentration of 3 μM. After culturing for 1 hour, TGF-β (Peprotech, Catalog No. 100-21R) at a final concentration of 5 ng / ml was added, and further cultured for 26 hours. After washing twice with phosphate buffer, total RNA was isolated using SV96 Total RNA Isolation System (Promega, catalog number Z3505). To 5 μl of the separated total RNA, 1 μl of 20 μM oligo dT and 4 μl of RNase-free distilled water were added, incubated at 65 ° C. for 5 minutes, and immediately ice-cooled. 5 μl buffer 4 μl, MgCl ₂ 2.4 μl, 10 mM dNTP 1 μl, RNasin 1 μl, ImpromII 1 μl, RNase-free distilled water 0.6 μl (all above from Promega) are added to 10 μl of the solution at 25 ° C. for 5 minutes, 42 ° C. Reverse transcription reaction was performed for 1 hour at 70 ° C. for 15 minutes.
In 5 μl of the reverse transcription reaction solution, SEQ ID NO: 3 (SEQ ID NO: 3: oligonucleotide designed as a primer for PCR for detecting DNA of fibronectin gene: tcgccatcag tagaaggtag ca 22), SEQ ID NO: 4 (SEQ ID NO: 4: fibronectin) In order to detect the DNA of the gene, 1 μl of each 20 pmol / μl primer represented by the oligonucleotide designed as a primer for PCR: tatactgaac accaggttgc aagtc 25 and SEQ ID NO: 5 (SEQ ID NO: 5: detect the DNA of fibronectin gene) For this purpose, 1.25 μl of a probe for detecting DNA of fibronectin gene represented by oligonucleotide designed as a probe: ctcaaccttc ctgaaactgc aaactccgtc 30), or Human GAPDH primer probe (Applied Biosystems, Inc. Log number 4310884E) 1.25 μl was added, TaqMan Universal PCR Master Mix (Applied Biosystems, catalog number 4304437) was added to 12.5 μl and sterilized water to adjust to 50 μl, and Optical 96-Well Reaction Plate (Ap catalog, Bio 96 No. N801-0560). As the standard, total RNA was prepared from cells to which only TGF-β was added, and cDNA solutions obtained by reverse transcription reaction of 250, 125, 62.5, 31.25, 15.625, and 7.8125 ng were used. Thereafter, PCR was performed using Gene Amp 7900 (Applied Biosystems) under conditions of 40 cycles of 50 ° C. for 5 minutes, 1 cycle, 95 ° C. for 15 seconds and 60 ° C. for 1 minute. For quantification, after preparing each standard line, the amount of fibronectin and the amount of GAPDH were calculated, and the amount of transcription was calculated according to the following formula.
Fibronectin transcription amount = fibronectin amount / GAPDH amount inhibition = [transcription amount (DMSO and TGF-β addition test group)]-transcription amount (compound and TGF-β addition test group)] / [transcription amount (DMSO and TGF-β addition) Test group)-Transcription amount (Test group without DMSO and TGF-β)] x 100
The degree of inhibition of the compounds of the present invention represented by compound numbers (2a-3) and (63a-1) was 70% or more.
It was confirmed that the compound of the present invention suppresses the transcription amount of fibronectin gene in skin fibroblasts promoted by TGF-β.

本発明により、組織における細胞外マトリックス遺伝子の発現量を減少させ、細胞外マトリックス蓄積量を低下させることにより、組織の線維化を改善させる組成物（即ち、細胞外マトリックス蓄積抑制剤や、線維症治療剤又は心不全治療剤）等の開発・提供が可能となる。
According to the present invention, a composition that improves the fibrosis of a tissue by reducing the amount of extracellular matrix gene expression in the tissue and decreasing the amount of extracellular matrix accumulation (ie, an extracellular matrix accumulation inhibitor, fibrosis) Development or provision of therapeutic agents or therapeutic agents for heart failure).

Claims

Formula (I)

[Where:
I. α represents an aromatic 5-membered ring or an aromatic 6-membered ring having two or more nitrogen atoms. In (Y _α ) _q , Y _α represents a group of the following X ₀ group or Y ₀ group, and q is , 0, 1, 2, or 3 and when q is 2 or more, Y _α is the same or different, and when q is 2 or more, two adjacent Y _α that are adjacent to each other are Z It may be condensed with an α ring by forming a group of ₀ group, and in (X _α ) _p , X _α represents a substituent not belonging to the following X ₀ group, Y ₀ group and Z ₀ group, p Represents 0, 1, 2 or 3, and when p is 2 or more, X _α is the same or different, and the sum of p and q is 3 or less.
(1) _{X 0} group: _{M a} - group _{[M a} is _{R b} - group (. _{R b} is representative of a is C1-C10 may be an alkyl group substituted with a halogen atom), a halogen atom, a nitro group, a cyano group, a hydroxyl _group, R c _-B a -R _d - group _{(R c} represents a halogen atom which may be substituted with C1-C10 alkyl group, _{B a} is oxy, thio, sulfinyl or sulfonyl group R _d represents a single bond or a C1-C10 alkylene group.), HOR _d -group (R _d represents the same meaning as described above), R _e -CO-R _d -group (R _e represents a hydrogen atom or a C1-C10 alkyl group which may be substituted with a halogen atom, and R _d represents the same meaning as described above), R _e —CO—O—R _d — group ( R _e and _{R d} represent the same meaning), R e O-CO- R d -. group _{(R e} and _{R d} are the same Means represents a), HO-CO-CH = CH- _{_{group, R e R e. 'N}} -R d - group _{(R e} and _{R e'} are the same or different, _{R e,} the same meaning R _e ′ represents the same meaning as R _e , R _d represents the same meaning as described above), R _e —CO—NR _e ′ —R _d — group (R _e , R _e 'And R _d represent the same meaning as described above.), R _b O—CO—N (R _e ) —R _d — group (R _b , R _e and R _d represent the same meaning as described above. ), R _e R _e 'N-CO-R _d -group (R _e , R _e ' and R _d represent the same meaning as described above), R _e R _e 'N-CO-NR _e '. '-R _d -groups (R _e , R _e ′ and R _e ″ are the same or different, R _e and R _e ′ have the same meaning as described above, and R _e ″ represents R _e and Represents the same meaning, and R _d is the same as above. ), R _e R _e ′ NC (═NR _e ″) —NR _e ″ ″ —R _d — groups (R _e , R _e ′, R _e ″ and R _e ″). 'Is the same or different, R _e , R _e ′ and R _e ″ represent the same meaning as described above, R _e ′ ″ represents the same meaning as R _e, and R _d represents the above And R _b —SO ₂ —NR _e —R _d — group (R _b , R _e and R _d represent the same meaning as described above), R _e R _e 'N— SO ₂ —R _d — group (R _e , R _e ′ and R _d represent the same meaning as described above. ), A C2-C10 alkenyl group or a C2-C10 alkynyl group. ].
(2) Y ₀ group: M _b0 -R _d _-group [M _b0 is M _{c0 -group} {M _c0 is M _d0 -R _d ' _-group {M _d0 is M _a _-group (M _a is It represents the same meaning as described above) and may be substituted with a 6-10-membered aryl group which may be substituted or a M _a -group (M _a represents the same meaning as described above). 5-10 membered heteroaryl group, or M _a -group (M _a represents the same meaning as described above) 3-10 membered ring carbonization which may contain an unsaturated bond which may be substituted A hydrogen or heterocyclic group, or

(b ₀ ) — group (in (b ₀ ), G ₀ represents a saturated or unsaturated, non-aromatic, 5- to 14-membered hydrocarbon ring or heterocyclic ring which may have a substituent. ),

A (c ₀ ) -group (in (c ₀ ), J ₀ may contain a nitrogen atom and forms an aromatic 5- to 7-membered ring);

(D ₀ ) -group {d ₀ is substituted with a carbonyl group or a thiocarbonyl group, and further, an oxy group, a thio group, a —NR ₁ -group {R ₁ is a hydrogen atom or a C1-C10 alkyl group, Or a halogen atom or an R ₂ —B ₁ — group (R ₂ represents a C 1 -C 10 alkyl group, a C 3 -C 10 alkenyl group or a C 3 -C 10 alkynyl group, and B ₁ represents an oxy group, a thio group, a sulfinyl group or A C2-C10 alkyl group, a C3-C10 alkenyl group, or a C3-C10 alkynyl group substituted with a sulfonyl group. }, A 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group. } Or

(E ₀ ) -group {e ₀ is a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a —NR ₁ — group (R ₁ is as defined above), a sulfinyl group or a sulfonyl group. It forms an optionally substituted 5-12 membered hydrocarbon ring. Represents}, _{R d} 'are the same or different and _{R d,} it represents the same meaning as _{R d.} }. _{}, M} c0 -B _a - group _{_(. M c0} and _{B a} are representing the same _meaning), M c0 -CO- group _{(. M c0} is representative of the same meaning _{as), M c0} -CO-O- group (M _c0 represents the same meaning as described above), M _c0 O-CO- group (M _c0 represents the same meaning as described above), M _c0 R _e N- group (M _c0 and R _e represent the same meaning as described above), M _c0 —CO—NR _e — group (M _c0 and R _e represent the same meaning as described above), M _c0 O—CO —NR _e — group (M _c0 and R _e represent the same meaning as described above), M _c0 R _e N—CO— group (M _c0 and R _e represent the same meaning as described above), _{_{M c0 R e N-CO-}} NR e '- group _(M c0, _{R e} and _{R _e'.} are representing the same meaning _{as), M c0 R e N-} C (= N _{_e ')} -NR _e' '- group _{_{_{(M c0, R e, R}}} e' and R _{e ''} represents the same _{_{meaning), M c0 -SO 2 -NR e}} -. group _{(M c0} And R _e represent the same meaning as described above) or a M _c0 R _e N—SO ₂ — group (M _c0 and R _e represent the same meaning as described above), and R _d represents the above Represents the same meaning as ].
(3) Z ₀ group: having halogen atom, C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group It may be a 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring and a group condensed with the α ring.
II. β is
Formula (I-1)

[Where:
(1) _Qα represents an optionally substituted hydroxyl group or an optionally substituted amino group.
(2) W _α represents an oxygen atom or a —NT _α — group (T _α represents a hydrogen atom or a substituent on a nitrogen atom).
(3) K _α and L _α are the same or different and represent a hydrogen atom or a substituent on a carbon atom, and K _α and L _α are a C3-C10 alkylene group which may have a substituent. Alternatively, it may form a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (I-2)

[Wherein, T _α represents the same meaning as described above, and L _β represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (I-3)

[Wherein, T _α represents the same meaning as described above, and L _γ represents a C1-C10 alkyl group. ]
A group represented by
Formula (I-4)

[Wherein, T _α represents the same meaning as described above. ]
A group represented by
Formula (I-5)

[Wherein, T _α represents the same meaning as described above, and K _β represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (I-6)

[Wherein W _α represents the same meaning as described above, and K _γ and L _δ represent a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene which may have a substituent. Make a basis. ]
A group represented by
Formula (I-7)

[Wherein Q _α and W _α represent the same meaning as described above, and K _δ and L _ε represent -V _α = V _α '-V _α ″ = V _α ''' -group (V _α , V _α ′, V _α ″ and V _α ″ ″ are the same or different and each represents an optionally substituted methine group or —N = group, and V _α , V _α ′, V _α ″ And at least one of V _α ′ ″ represents —N = group. ]
A group represented by
Formula (I-8)

[Wherein, T _α represents the same meaning as described above, and Q _β represents a hydroxyl group which may be substituted. ]
Or a group represented by
Formula (I-9)

[Wherein U and W _α represent the same meaning as described above. ]
Represents a group represented by
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A composition for inhibiting transcription of an extracellular matrix gene, comprising a cinnamoyl compound represented by the formula (1) and an inert carrier.

Formula (II)

(E ₀ ) -group {e ₀ is a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a —NR ₁ — group (R ₁ is as defined above), a sulfinyl group or a sulfonyl group. It forms an optionally substituted 5-12 membered hydrocarbon ring. Represents}, _{R d} 'are the same or different and _{R d,} it represents the same meaning as _{R d.} }. _{}, M} c0 -B _a - group _{_(. M c0} and _{B a} are representing the same _meaning), M c0 -CO- group _{(. M c0} is representative of the same meaning _{as), M c0} -CO-O- group (M _c0 represents the same meaning as described above), M _c0 O-CO- group (M _c0 represents the same meaning as described above), M _c0 R _e N- group (M _c0 and R _e represent the same meaning as described above), M _c0 —CO—NR _e — group (M _c0 and R _e represent the same meaning as described above), M _c0 O—CO —NR _e — group (M _c0 and R _e represent the same meaning as described above), M _c0 R _e N—CO— group (M _c0 and R _e represent the same meaning as described above), _{_{M c0 R e N-CO-}} NR e '- group _(M c0, _{R e} and _{R _e'.} are representing the same meaning _{as), M c0 R e N-} C (= N _{_e ')} -NR _e' '- group _{_{_{(M c0, R e, R}}} e' and R _{e ''} represents the same _{_{meaning), M c0 -SO 2 -NR e}} -. group _{(M c0} And R _e represent the same meaning as described above) or a M _c0 R _e N—SO ₂ — group (M _c0 and R _e represent the same meaning as described above), and R _d represents the above Represents the same meaning as ].
(3) Z ₀ group: having halogen atom, C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group It may be a 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring and a group condensed with the α ring.
II. β is
Formula (II-1)

[Where:
(1) _Qα represents an optionally substituted hydroxyl group or an optionally substituted amino group.
(2) W _α represents an oxygen atom or a —NT _α — group (T _α represents a hydrogen atom or a substituent on a nitrogen atom).
(3) K _α and L _α are the same or different and represent a hydrogen atom or a substituent on a carbon atom, and K _α and L _α are a C3-C10 alkylene group which may have a substituent. Alternatively, it may form a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (II-2)

[Wherein, T _α represents the same meaning as described above, and L _β represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (II-3)

[Wherein, T _α represents the same meaning as described above, and L _γ represents a C1-C10 alkyl group. ]
A group represented by
Formula (II-4)

[Wherein, T _α represents the same meaning as described above. ]
A group represented by
Formula (II-5)

[Wherein, T _α represents the same meaning as described above, and K _β represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (II-6)

[Wherein W _α represents the same meaning as described above, and K _γ and L _δ represent a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene which may have a substituent. Make a basis. ]
A group represented by
Formula (II-7)

[Wherein Q _α and W _α represent the same meaning as described above, and K _δ and L _ε represent -V _α = V _α '-V _α ″ = V _α ''' -group (V _α , V _α ′, V _α ″ and V _α ″ ″ are the same or different and each represents an optionally substituted methine group or —N = group, and V _α , V _α ′, V _α ″ And at least one of V _α ′ ″ represents —N = group. ]
A group represented by
Formula (II-8)

[Wherein, T _α represents the same meaning as described above, and Q _β represents a hydroxyl group which may be substituted. ]
Or a group represented by

Formula (II-9)
[Wherein U and W _α represent the same meaning as described above. ]
Represents a group represented by
However, when α is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:

Formula (III)

[Where:
I. A0 represents an aromatic 5-membered ring or an aromatic 6-membered ring having two or more nitrogen atoms.
II. (X _A0 ) In _p , X _A0 represents a group included in any of the following groups A ₀ to N ₀ , p represents 0, 1, 2, or 3, and p is 2 or more In this case, X _A0 is the same or different.
(1) Group A ₀ : D ₁ -R ₄ -group [D ₁ is (R _1- (O) _k- ) A ₁ N- (O) _{k '} -group {R ₁ is a hydrogen atom or a C1-C10 alkyl group, a or a halogen atom or R ₂ -B 1 _- group (R ₂ represents a C1-C10 alkyl group, a C3-C10 alkenyl group or C3-C10 alkynyl group, B ₁ is an oxy group, A C2-C10 alkyl group, a C3-C10 alkenyl group, or a C3-C10 alkynyl group substituted with a thio group, a sulfinyl group, or a sulfonyl group), k represents 0 or 1, ₁ represents R ₃ — (CHR ₀ ) _m — (B ₂ —B ₃ ) _{m ′} — group {R ₃ represents a hydrogen atom, a halogen atom or an R ₂ —B ₁ — group (R ₂ and B ₁ represent Represents a C1-C10 alkyl group, a C2-C10 alkenyl group, or a C2-C10 alkynyl group which may be substituted. R ₀ is a hydrogen atom, C1-C10 alkyl or C2-C10 haloalkyl group, m represents 0 or 1, _{B 2} represents a single bond, oxy group, thio group, or -N _{((O) n} R _1. ') - group _{(R 1'} is different from _{R 1} identical or different, represent the same meaning as _{R 1,} n denotes the representative) 0 or 1, _{B 3} is a carbonyl group, thio A carbonyl group or a sulfonyl group, m ′ represents 0 or 1, and when B ₃ is a sulfonyl group, m is 0 and R ₃ is not a hydrogen atom. }, And k ′ represents 0 or 1. }, And R ₄ represents a C1-C10 alkylene group. _{_{However, R 0 'R 0''}} N-R 4 - group _{(R 0'} and R _{0 ''} is different from _{R 0} and same or different, represent the same meaning as _{R 0,} _{R 4} is the same Represents the meaning of. _], D 2 -R ₄ - group _{[D 2} is a cyano _{_{group, R 1 R 1 'NC (}} = N- (O) n -A 1) - group _{_{(R 1, R 1',}} n, and _{A 1} Represents the same meaning as described above.), Represents an A ₁ N═C (—OR ₂ ) — group (A ₁ and R ₂ represent the same meaning as described above) or an NH ₂ —CS— group. , R ₄ represents the same meaning as described above. ], D ₃ -R ₄ -group {D ₃ represents a nitro group or R ₁ OSO ₂ -group (R ₁ represents the same meaning as described above), and R ₄ represents the same meaning as described above. To express. } Or R ₁ OSO ₂ — group (R ₁ represents the same meaning as described above).
(2) B ₀ group:

(A ₀ ) — group (in (a ₀ ), E ₀ is a saturated or unsaturated, aromatic or non-aromatic, 5- to 14-membered hydrocarbon ring or heterocyclic group which may have a substituent. It forms a ring and R ₁ represents the same meaning as described above.
(3) C ₀ group: halogen atom, R ₂ —B ₁ — group (R ₂ and B ₁ are as defined above), D ₄ —R ₄ — group [D ₄ is a hydroxyl group or A _1- O-group (A ₁ represents the same meaning as described above) and R ₄ represents the same meaning as described above. ], _{D 5} - group _[D 5 _{is, O = C (R 3)} - group _{(R 3} represents the same meaning as _{_{above.), A 1 - (O}} ) n -N = C (R 3) A group (A ₁ , n and R ₃ are as defined above), R ₁ —B ₀ —CO—R ₄ — (O) _n —N═C (R ₃ ) — group {R ₁ , R ₄ , n and R ₃ represent the same meaning as described above, and B ₀ represents an oxy group, a thio group, or a —N ((O) _m R ₁ ′)-group (R ₁ ′ and m Represents the same meaning as }, D ₂ —R ₄ — (O) _n —N═C (R ₃ ) — group (D ₂ , R ₄ , n and R ₃ represent the same meaning as described above) or R ₁ A ₁ N —N═C (R ₃ ) — group (wherein R ₁ , A ₁ and R ₃ represent the same meaning as described above). ], R ₁ A ₁ N—O—R ₄ — group (R ₁ , A ₁ and R ₄ represent the same meaning as described above), R ₁ (A _1- (O) _n —) N— group (R ₁ , A ₁ and n represent the same meaning as described above), D ₂ -group (D ₂ represents the same meaning as described above) or D ₃ -group (D ₃ represents the same as above. C2-C10 alkenyl group substituted with the same meaning.
(4) D group ₀ :

(b ₀ ) —R ₄ — group (in (b ₀ ), G ₀ is a saturated or unsaturated, non-aromatic, 5- to 14-membered hydrocarbon ring or heterocyclic group which may have a substituent. A ring)

(C ₀ ) —R ₄ — group (in (c ₀ ), J ₀ may contain a nitrogen atom, forms an aromatic 5- to 7-membered ring, and R ₄ has the same meaning as described above). , A halogen atom, an R ₂ -B ₁ -R ₄ -group (R ₂ , B ₁ and R ₄ are as defined above), a D ₄ -R ₄ -group (D ₄ and R ₄ are The same meaning as above), D ₅ -group (D ₅ represents the same meaning as above), D ₁ -R ₄ -group (D ₁ and R ₄ have the same meaning as above). represented), _{D 2} -. group _{(D 2,} the representative of the same meaning as) or _D 3 -R ₄ -. group _{(D 3,} and _{R 4} is substituted with representing) the same meaning as above. A C2-C10 alkynyl group.
(5) Group E ₀ : A ₂ —CO—R ₅ — group. However, when A ₂ is a hydroxyl group, R ₅ is not a vinylene group.
_{[A 2} is,
(i) A ₃ -B ₄ -group {A ₃ is a hydrogen atom, a C1-C10 alkyl group, a C2-C10 haloalkyl group, or a C2-C10 alkenyl group optionally substituted with a halogen atom, Or a C3-C10 alkynyl group that may be substituted with a halogen atom, or a R _a0- (R ₄ ) _m -group (R _a0 is an _optionally substituted aryl group or heteroaryl group of 5-7 membered ring) R ₄ and m represent the same meaning as described above), or (b ₀ ) —R ₄ — group ((b ₀ ) and R ₄ represent the same meaning as described above), ( c ₀ ) —R ₄ — group ((c ₀ ) and R ₄ are as defined above), R ₂ —B ₁ —R ₄ — group (R ₂ , B ₁ and R ₄ are represents the same meaning _as), D ₄ -R 4 -. group _{(D 4} and _{R 4} represent the same meaning as above), _{D 5} -. group _{(D 5,} the a Represents the same meaning.), D ₁ -R ₄ -group (D ₁ and R ₄ represent the same meaning as described above), D ₂ -group (D ₂ represents the same meaning as described above). ), D ₃ -R ₄ -group (D ₃ and R ₄ are as defined above) or A ₄ -SO ₂ -R ₄ -group {A ₄ is a (b ₀ ) -group (( b ₀₎ represent the same _{meaning), (c 0) -.} . group _{((c 0)} represents the same meaning as) or _{_R 1} _R 1 'N- group _{(R 1} and R ₁ ′ represents the same meaning as described above.), And R ₄ represents the same meaning as described above. } Represents a C1-C10 alkyl group substituted with
B ₄ represents an oxy group, a thio group, or a —N ((O) _m R ₁ ) — group (where R ₁ and m represent the same meaning as described above). However, when B ₄ is a thio group, A ₃ is not a hydrogen atom. },
(ii) R ₁ —B ₄ —CO—R ₄ —B ₄ ′ — group (R ₁ , B ₄ and R ₄ have the same meaning as described above, and B ₄ ′ is the same as or different from B _4. represents _{B 4} same meaning as the proviso that when _{B 4} is a thio group, _{R 2} is not hydrogen atom) or _{_{_{D 2 -R 4 -B 4 -.}}} . group _(D 2, _{R 4} and _{B 4} is Represents the same meaning as described above).
(iii) R ₂ —SO ₂ —NR ₁ — group (R ₂ represents the same meaning as described above, except for a hydrogen atom; R ₁ represents the same meaning as described above),
(iv) (b ₀ ) -group ((b ₀ ) represents the same meaning as described above),
(v) (c ₀ ) -group ((c ₀ ) represents the same meaning as described above) or
(vi) R ₁ A ₁ N—NR ₁ ′ -group (R ₁ , A ₁ and R ₁ ′ have the same meaning as described above), and R ₅ may be substituted with a halogen atom. A C2-C10 alkenylene group or a C2-C10 alkynylene group is represented. ]
(6) _{F 0} _Group: A 5 _-B 5 -R ₆ - group _{[A 5} is _{D 4} - group (. _{D 4} may represent the same meaning as described above), _{D 1} - group _{(D 1} is It represents the same meaning as described above), D ₃ -group (D ₃ represents the same meaning as described above) or A ₄ —SO ₂ — group (A ₄ represents the same meaning as described above). A C2-C10 alkyl group substituted with or R ₂ —B ₁ — group (R ₂ and B ₁ are as defined above), D ₂ — group (D ₂ is the same as defined above) C1 substituted with a D ₅ -group (D ₅ represents the same meaning as described above) or an A ₂ —CO— group (A ₂ represents the same meaning as described above). represents -C10 alkyl group, _{B 5} is _{B 1} - group _{(B 1,} the represent the same meaning as.) or -NA ₁ - group _{(a 1} represent the same meanings as the above.) the It represents, _{R 6} is, Bond or an C1-C10 alkylene group. ]
It is.
(7) _{G 0} _Group: A ₆ _-B 5 -R 6 - group _{[A 6} _{is, (a} 0) -R ₄ - group _{((a 0)} and _{R 4} represents the same meaning as above.) or C2-C10 alkenyl group, or C2-C10 alkynyl group, or a halogen _atom, R 2 -B ₁ - group (. _{R 2} and _{B 1} may represent the same meaning as described above), _{D 5} - group _{(D 5} represents the same meaning as.), _{D 2} - group (. _{D 2,} the representative of the same meaning as) or _a 2 -CO- group _{(a 2,} the same as the A C2-C10 alkenyl group substituted with a meaning) or a halogen atom, an R ₂ -B ₁ -group (R ₂ and B ₁ have the same meaning as described above), a D ₅ -group ( D ₅ represents the same meaning), _{D 2} -.. group _{(D 2,} the representative of the same meaning as) or _a 2 -CO- group _{(a 2,} the same meaning . Representing) C2-C10 alkynyl group substituted with, or, _{(b 0)} - group _{((b 0)} represent the same meaning as above),. _{(C 0)} - group _{((c 0)} is , D ₄ -group (D ₄ represents the same meaning as described above), D ₁ -group (D ₁ represents the same meaning as described above) or D ₃ - group (. _{D 3} may represent the same meanings as the above) C3-C10 alkenyl group substituted with, or, _{D 4} - group (. _{D 4} may represent the same meaning as described above), _{D 1} - group (D _1, the represent the same meaning as.) or D ₃ - group (. D ₃ may represent the same meanings as the above) represents a C3-C10 alkynyl group substituted with, B ₅ and R ₆ represents the same meaning as described above. ]
It is.
(8) H ₀ group:
D ₂ —N (— (O) _n —A ₁ ) —R ₆ — group (D ₂ , n, A ₁ and R ₆ are as defined above), D ₂ — group (D ₂ is Represents the same meaning as described above, except for a cyano group.), R ₁ (R ₁ ′ (O) _n ) N—CR ₁ ″ = N—R ₆ — group (R ₁ , R ₁ ′, n and _{R 6} represent the same meanings, R _{1 ''} are the same or different phase and _{R 1,} represents the same meaning as _{_{_{R 1), R 1 -.}}} (O) n -N = CR ₁ _'-NR 2 -R ₆ - group _{_{(R 1, n, R 1}} '., R 2 and _{R 6} represent the same meaning as described _{_{above), R 2 -B 3 -NR 1}} -CO-NR 1 '-R ₆ -group (R ₂ , B ₃ , R ₁ , R ₁ ' and R ₆ represent the same meaning as described above), D ₂ -CO-NR ₁ -R ₆ -group (D ₂ , R ₁ and _{R 6} represent the same meanings as the above. Or _{_{_{A 2 -COCO-NR 1 -R 6}}} - group _(A 2, _{R 1} and _{R 6} represent the same meanings as the above.)
It is.
(9) I ₀ group:
_{_{_{A 7 -B 6 -N ((O}}} ) n R 1) -R 6 - group _{[A 7} is optionally substituted C2-C10 alkenyl group with a halogen atom, C2-C10 alkynyl group, C3-C10 haloalkynyl A group, R ₂ -B ₁ -R ₄ -group (R ₂ , B ₁ and R ₄ are as defined above), D ₄ -R ₄ -group (D ₄ and R ₄ are represents the same _meaning), D 5 -R ₄ -. group _{(D 5} and _{R 4} represents the same _meaning), D 1 -R ₄ -. group _{(D 1} and _{R 4,} the a Represents the same meaning.), (B ₀ ) —R ₄ — group ((b ₀ ) and R ₄ represent the same meaning as described above), (c ₀ ) —R ₄ — group ((c ₀ ) And R ₄ represent the same meaning as described above.), D ₂ -R ₄ -group (D ₂ and R ₄ represent the same meaning as described above), D ₃ -R ₄ -group (D ₃ and _{R 4} are the Represents the same _{_{meaning), A 4 -SO 2 -R 4}} -. Group _{(A 4} and _{R 4} represent the same meanings as the above) or _A 2 _{-CO-R 4} -. Group _{(A 2} and R ₄ represents the same meaning as described above), B ₆ represents a carbonyl group or a thiocarbonyl group, and n, R ₁ and R ₆ represent the same meaning as described above. _{_{], A 8 -CS-N (}} (O) n R 1) -R 6 - group _{[A 8} is a hydrogen atom, or represents a optionally substituted C1-C10 alkyl group with a halogen atom, n, R ₁ and R ₆ represent the same meaning as described above. ],
_{_{_{A 7 '-B 2' -B 3}}} -N ((O) n R 1) -R 6 - group _{[A 7} 'is optionally substituted C3-C10 alkenyl group with a halogen atom, is substituted with a halogen atom and it may be C3-C10 alkynyl _{_{_{group, R 2 -B 1 -R 4 '}}} - group _{(R 2} and _{B 1} represent the same meaning as, _{R 4'} represents a C2-C10 alkylene group.) , _D ₄ -R 4 '- group _{(D 4} and _{R 4'} represents the same meaning _{_{as.), D 1 -R 4 '}} - group _{(D 1} and _{R 4',} wherein the same meaning ), (B ₀ ) -R ₄ ′ -group ((b ₀ ) and R ₄ ′ represent the same meaning as described above), (c ₀ ) -R ₄ ′ -group ((c ₀ ) and _{R 4} 'represents the same _meaning), D 2 -R ₄ -. group _{(D 2} and _{R 4} represent the same meaning as _{_{above), D 3 -R 4.'}} - group (D ₃ and R ₄ ′ have the same meaning as above. Represents a taste) or A ₂ —CO—R ₄ — group (where A ₂ and R ₄ represent the same meaning as described above), and B ₂ ′ represents an oxy group, a thio group or —N ((( O) _{n ′} R ₁ ′) -group (where n ′ is the same as or different from n and represents the same meaning as n, and R ₁ ′ represents the same meaning as described above), B ₃ , n, R ₁ and R ₆ represent the same meaning as described above. _{_{], A 8 '-B 2'}} -CS-N ((O) n R 1) -R 6 - group _{[A 8} 'represents a C1-C10 alkyl or C2-C10 haloalkyl group, _{B 2'} is , And the same meaning as described above, and n, R ₁ and R ₆ represent the same meaning as described above. _{_{], A 8 '-S-B}} 3' -N ((O) n R 1) -R 6 - group _{_{[A 8 ', n, R}} 1 and _{R 6} represent the same meanings as above, _{B 3} 'Represents a carbonyl group or a sulfonyl group. ] Or _{_{_{A 7 '' -SO 2 -N (}}} (O) n R 1) -R 6 - group [A _{7 ''} is, C2-C10 alkenyl group, C3-C10 alkenyl group substituted with a halogen atom, a halogen optionally substituted C3-C10 alkynyl group _{_{_{atom, R 2 -B 1 -R 4 '}}} - group _(R 2, _{B 1} and _{R 4'.} is representing the same meaning as _above), D 4 -R ₄ '- group _{(D 4} and _{R 4'} represents the same _meaning.), D 5 -R ₄ - group (. _{D 5} and _{R 4} represent the same meaning as described above), _{D 1} -R ₄ '-group (D ₁ and R ₄ ' represent the same meaning as described above), (b ₀ ) -R ₄ '-group ((b ₀ ) and R ₄ ' are the same as defined above. Represents a meaning), (c ₀ ) -R ₄ '-group ((c ₀ ) and R ₄ ' represent the same meaning as described above), D ₂ -R ₄ -group (D ₂ and R ₄ Represents the same meaning as described above). NO ₂ —R ₄ — group (R ₄ represents the same meaning as described above) or A ₂ —CO—R ₄ — group (A ₂ and R ₄ represent the same meaning as described above). , N, R ₁ and R ₆ represent the same meaning as described above. ]
It is.
(10) _{J 0} _Group: A 7 -CO- group _{(A 7} represents the same meaning as.), _Or, A 9 -CS- group _{(A 9} represents _{A 7} or _{A 8.)} Or A ₉ ′ (O) _m N═C (A ₉ ) — group (A ₉ ′ represents A ₇ ′ or A ₈ ′, and m and A ₉ represent the same meaning as described above). Or D ₂ —CO— group (D ₂ represents the same meaning as described above), A ₂ —COCO— group (A ₂ represents the same meaning as described above), or A _9- CO-B ₁ '-R ₆ -group (A ₉ and R ₆ represent the same meaning as described above, B ₁ ' represents an oxy group or a thio group, provided that B ₁ 'is an oxy group, When A ₉ is not A ₈ ), or A ₉ -CS-B ₁ '-R ₆ -group (A ₉ , B ₁ ' and R ₆ represent the same meaning as described above. ), or, _{A 7} '' _-SO 2 -B '-R ₆ - group _{_{(A 7'', B 1}} ' and _{R 6} represents the same meaning as.), _{_{_{Or, A 8 -SO 2 -B 1 '}}} -R 6 - group (A ₈ , B ₁ ′ and R ₆ represent the same meaning as described above, provided that A ₈ is not a hydrogen atom.) Or A ₉ ′ -B ₂ ′ -B ₃ -B ₁ '-R ₆ - group _{_{(a 9', B 2 '}} , B 3, B 1' and _{R 6} represent the same meanings as the above.), or, _{(b 0)} - group ((b ₀₎ represents the same meaning) or (c ₀₎ -. group ((c ₀₎ is a C2-C10 alkenyl group substituted with representing) the same meaning as above..
(11) K ₀ group: A ₁₀ -N ((O) _n R ₁ ) —CO—R ₆ — group [A ₁₀ is a hydrogen atom (where n is not 0), A ₇ ″ -SO ₂ -group (A ₇ ″ represents the same meaning as described above), A ₈ —SO ₂ — group (A ₈ represents the same meaning as described above, provided that A ₈ is a hydrogen atom. . which become not), _{a 9} 'O-group _{(a 9'} represents the same meaning where, n is not a _{1), a 9.. '} - group _{(a 9',} the same meaning Provided that when n is 0, A ₈ ′ is excluded), R ₂ OCH ₂ — group (R ₂ represents the same meaning as described above), A ₂ —CO—R ₄ — group ( A ₂ and R ₄ represent the same meaning as described above.) Or A ₂ —CO—CH (CH ₂ CO—A ₂ ) — group (A ₂ represents the same meaning as described above), n, R ₁ and R ₆ are This means the same meaning as above. ]
It is.
(12) _{L 0} _groups: - (. Here, n is not _{_{_{0) A 10 '-N ((}}} O) n R 1) -SO 2 -R 6 group _{[A 10'} is a hydrogen atom, _{A 9} ' O-group (A ₉ 'represents the same meaning as described above, provided that n is not 1), A ₉ ' -group (A ₉ 'represents the same meaning as described above, provided that n is When 0, A ₈ ′ is excluded.), R ₂ —CO— group (R ₂ represents the same meaning as described above), A ₂ —CO—R ₄ — group (A ₂ and R ₄ are Represents the same meaning as described above) or A ₂ —CO—CH (CH ₂ CO—A ₂ ) — group (A ₂ represents the same meaning as described above), and represents n, R ₁ and R _6. Represents the same meaning as described above. ] A ₉ ″ R ₁ N—SO ₂ —N ((O) _n R ₁ ′) —R ₆ — group [A ₉ ″ is a hydrogen atom or A ₉ ′ -group (A ₉ ′ R ₁ , n, R ₁ ′ and R ₆ represent the same meaning as described above. ] Or (b ₀ ) —SO ₂ —N ((O) _n R ₁ ′) —R ₆ — group [(b ₀ ), n, R ₁ ′ and R ₆ represent the same meaning as described above. ]
It is.
(13) M ₀ group: R ₁ (R ₂ S) C═N—R ₆ — group (R ₁ , R ₂ and R ₆ represent the same meaning as described above), R ₂ B (R ₂ ′ _{B ') C = N-R} 6 - group _{(R 2} and _{R 6} represent the same meaning, _{R 2'} are identical or different phase and _{R 2,} and _{R 2,} represent the same meaning, B and B ′ are the same or different and represent an oxy group or a thio group.), R ₁ R ₁ ′ N— (R ₂ S) C═N—R ₆ —group (R ₁ , R ₁ ′, R ₂ and R ₆ represent the same meaning as described above.), R ₁ N═C (SR ₂ ) —NR ₂ ′ —R ₆ — group (R ₁ , R ₂ , R ₂ ′ and R ₆ are Or R ₁ (R ₁ ′ O) N—R ₆ — group (R ₁ , R ₁ ′ and R ₆ represent the same meaning as described above.)
It is.
(14) _{N 0} _group: (. _{R 1} may represent the same meanings as the above) A 11 -P (= O) (OR 1 ') -R 4 - - group _{[A 11} is _{R 1} radical, R ₁ O—R ₆ — group (R ₁ and R ₆ are as defined above) or R ₁ OCO—CHR ₀ — group (where R ₁ and R ₀ are as defined above). R ₁ ′ and R ₄ represent the same meaning as described above. ]
It is.
III. (Y _A0 ) In _q , Y _A0 represents a group of the following X ₀ group and Y ₀ group, q represents ₀ , 1, 2, or 3, and p (p represents the same meaning as described above). .) And q is 3 or less, and when q is 2 or more, Y _A0 is the same or different, and when q is 2 or more, two adjacent same or different Y _A0 are It forms a Z ₀ group group, may be condensed with A0 ring.
(1) X ₀ group:
M _a -group [M _a is an R _b -group (R _b represents a C1-C10 alkyl group optionally substituted with a halogen atom), halogen atom, nitro group, cyano group, hydroxyl group, R _c- B _a -R _d - the group _{(R c,} represents a substituted C1-C10 may be an alkyl group with a halogen atom, _{B a} represents oxy, thio, sulphinyl group or a sulfonyl group, _{R d} is A single bond or a C1-C10 alkylene group), a HOR _d -group (R _d is as defined above), a R _e -CO-R _d -group (R _e is a hydrogen atom, or Represents a C1-C10 alkyl group which may be substituted with a halogen atom, R _d represents the same meaning as described above), R _e —CO—O—R _d — group (R _e and R _d are represents the same meaning), R e O-CO- R d -. group _{(R e} and _{R d} represent the same meaning as above ), HO-CO-CH = CH- _{_{group, R e R e 'N-}} R d - group _{(R e} and _{R e'} are the same or different, _{R e} represents the same meanings as defined, R _e ′ represents the same meaning as R _e, and R _d represents the same meaning as described above.), R _e —CO—NR _e ′ —R _d — group (R _e , R _e ′ and R _d Represents the same meaning as described above), R _b O—CO—N (R _e ) —R _d — group (R _b , R _e and R _d represent the same meaning as described above), R. _e R _e 'N—CO—R _d — group (R _e , R _e ′ and R _d are as defined above), R _e R _e ′ N—CO—NR _e ″ —R _d - group _(R e, _{R e} 'and R _e' 'are the same or different, _{R e} and _{R e'} represents the same meaning as, R _{e ''} are the same meaning as _{R e} R _d represents the same meaning as described above. ), R _e R _e ′ N—C (═NR _e ″) —NR _e ′ ″ —R _d — groups (R _e , R _e ′, R _e ″ and R _e ″ ″ are identical) Or, differently, R _e , R _e ′ and R _e ″ have the same meaning as described above, R _e ′ ″ has the same meaning as R _e, and R _d has the same meaning as described above. the _{_{represented), R b -SO 2 -NR e}} -R d -.. group _(R b, _{R e} and _{R d,} which represents the same meaning as _{_{above), R e R e 'N}} -SO 2 -R _d -group (R _e , R _e ′ and R _d represent the same meaning as described above. ), A C2-C10 alkenyl group or a C2-C10 alkynyl group. ].
(2) Y group ₀ :
M _b0 -R _d _-group [M _b0 is M _{c0 -group} {M _c0 is M _d0 -R _d ' _-group {M _d0 is M _a _-group (M _a represents the same meaning as described above) 5-10-membered ring hetero group optionally substituted with 6-10-membered ring aryl group or M _a -group (M _a represents the same meaning as described above). An aryl group, or a M _a -group (M _a represents the same meaning as described above), and _{a 3- to} 10-membered hydrocarbon ring or heterocyclic ring that may contain an unsaturated bond may be formed. Group or

(b ₀ ) -group ((b ₀ ) represents the same meaning as described above),

(C ₀ ) -group ((c ₀ ) represents the same meaning as described above),

(D ₀ ) -group {d ₀ is substituted with a carbonyl group or a thiocarbonyl group, and further, an oxy group, a thio group, an —NR ₁ -group (R ₁ represents the same meaning as described above), sulfinyl. A 5- to 12-membered hydrocarbon ring which may be substituted with a group or a sulfonyl group. } Or

(E ₀ ) -group {e ₀ is a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a —NR ₁ — group (R ₁ is as defined above), a sulfinyl group or a sulfonyl group. It forms an optionally substituted 5-12 membered hydrocarbon ring. Represents}, _{R d} 'are the same or different and _{R d,} it represents the same meaning as _{R d.} }. _{}, M} c0 -B _a - group _{_(. M c0} and _{B a} are representing the same _meaning), M c0 -CO- group _{(. M c0} is representative of the same meaning _{as), M c0} -CO-O- group (M _c0 represents the same meaning as described above), M _c0 O-CO- group (M _c0 represents the same meaning as described above), M _c0 R _e N- group (M _c0 and R _e represent the same meaning as described above), M _c0 —CO—NR _e — group (M _c0 and R _e represent the same meaning as described above), M _c0 O—CO —NR _e — group (M _c0 and R _e represent the same meaning as described above), M _c0 R _e N—CO— group (M _c0 and R _e represent the same meaning as described above), _{_{M c0 R e N-CO-}} NR e '- group _(M c0, _{R e} and _{R _e'.} are representing the same meaning _{as), M c0 R e N-} C (= N _{_e ')} -NR _e' '- group _{_{_{(M c0, R e, R}}} e' and R _{e ''} represents the same _{_{meaning), M c0 -SO 2 -NR e}} -. group _{(M c0} And R _e represent the same meaning as described above) or a M _c0 R _e N—SO ₂ — group (M _c0 and R _e represent the same meaning as described above), and R _d represents the above Represents the same meaning as ].
(3) Z ₀ group: having halogen atom, C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group It may be a 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring and a group condensed with the A0 ring.
IV. B0 is
Formula (III-1)

[Where:
(1) Q _A0 is a hydroxyl group, (b ₀ ) -group ((b ₀ ) represents the same meaning as described above), A ₉ -B ₆ -B _c -group [A ₉ and B ₆ are B _c represents an oxy group or —N ((O) _m R ₁ ) — group (m and R ₁ represent the same meaning as described above). However, when A ₉ is a hydrogen atom, B _c is not a sulfonyl group. _{_{], A 7 '' -SO 2}} -B c - group (A _{7 ''} and _{B c} represents the same meaning _{_{as.), A 8 -SO 2 -B}} c - group _{(A 8} and _{B c} Represents the same meaning as described above, provided that A ₈ is not a hydrogen atom.), R ₁ R ₁ ′ N—SO ₂ —B _c — group (R ₁ , R ₁ ′ and B _c are represents the same meaning _{_{as),. (b 0) -SO}} 2 -B c - groups _{((b 0)} and _{B c} represent the same meaning as _{_{above), a 9 '-B c -}} . group ( A ₉ ′ and B _c represent the same meaning as described above.), D ₅ —R ₄ —B _c — group (D ₅ , R ₄ and B _c represent the same meaning as described above), M _c0 -B ₃ -B _c - groups _(M c0, _{B 3} and _{B c,} the represent the same meaning as.) or _M c0 -B _c - groups _{(M c0} and _{B c,} the same meaning Represents).
_{(2) W A0} represents an oxygen atom or _{-NT A0} - group _{[T A0} is a hydrogen atom, _{A 9} '- group _{(A 9'.} Are representing the same meaning as _above), D 5 -R ₄ - A group (D ₅ and R ₄ represent the same meaning as described above) or a M _c0 -group (M _c0 represents the same meaning as described above). ].
(3) K _A0 represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, L _A0 represents a hydrogen atom, a C1-C10 alkyl group or an M _{b0 -group} (M _b0 represents the same meaning as described above). ) And K _A0 and L _A0 may be substituted with a C3-C10 alkylene group, or a single or a plurality of Ma-groups (Ma represents the same meaning as described above). May form a good C4-C10 alkenylene group. ]
A group represented by
Formula (III-2)

[Wherein, T _A0 represents the same meaning as described above, and L _B0 represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (III-3)

[Wherein, T _A0 represents the same meaning as described above, and L _C0 represents a C1-C10 alkyl group. ]
A group represented by
Formula (III-4)

[Wherein, T _A0 represents the same meaning as described above. ]
A group represented by
Formula (III-5)

[Wherein, T _A0 represents the same meaning as described above, and K _B0 represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (III-6)

[Wherein W _A0 represents the same meaning as described above, and K _C0 and L _D0 represent a C3-C10 alkylene group or a single or a plurality of Ma-groups (Ma is the same as defined above). Represents a C4-C10 alkenylene group which may be substituted. ]
A group represented by
Formula (III-7)

[In the formula, Q _A0 and W _A0 represent the same meaning as described above, and _KD0 and _LE0 represent -V _A0 = V _A0 '-V _A0 ''= V _A0 ''' _-group {V _A0 _{_{, V A0 ', V A0'}} ' and _{V A0'} '' are the same or different, _{M a} - group (. _{M a} is that the represent the same meaning as) methine group optionally substituted by a, or , -N = group, and at least one of V _A0 , V _A0 ′, V _A0 ″ and V _A0 ″ ″ represents —N = group. }. ]
A group represented by
Formula (III-8)

[Wherein, T _A0 represents the same meaning as described above, Q _B0 represents a hydroxyl group, and an A ₉ -B ₆ -O- group [A ₉ and B ₆ represent the same meaning as described above. _{_{], A 7 '' -SO 2}} -O- group (A _{7 ''} represents the same meaning _as.), A 8 _-SO 2 -O- group _{(A 8} are the same meaning as above Provided that A ₈ is not a hydrogen atom.), R ₁ R ₁ ′ N—SO ₂ —O— group (R ₁ and R ₁ ′ represent the same meaning as described above), (b ₀ ) _-SO 2 -O- group _{((b 0)} is. representing the same meaning), _{a 9} '-O- group _{(a 9'} represents the same meaning as above.), _{D 5} —R ₄ —O— group (D ₅ and R ₄ represent the same meaning as described above), M _c0 —B ₃ —O— group (M _c0 and B ₃ represent the same meaning as described above). ) Or a M _c0 —O— group (M _c0 represents the same meaning as described above). ]
Or a group represented by
Formula (III-9)

[Wherein U and W _A0 represent the same meaning as described above. ]
Represents a group represented by
However, when A0 is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:

Formula (IV)

[Where:
I. A represents an aromatic 5-membered ring or an aromatic 6-membered ring having two or more nitrogen atoms.
II. (X _A ) In _p , X _A represents a group included in any of the following groups A to N, p represents 0, 1, 2, or 3, and when p is 2 or more , X _A are the same or different.
(1) Group A: D ₁ -R ₄ -group [D ₁ is (R _1- (O) _k- ) A ₁ N- (O) _{k '} -group {R ₁ is a hydrogen atom or C 1 -C10 alkyl group, or a halogen atom or R ₂ -B ₁ -group (R ₂ represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl group, B ₁ represents an oxy group, thio group, Represents a C2-C10 alkyl group, a C3-C10 alkenyl group, or a C3-C10 alkynyl group substituted with a group, sulfinyl group or sulfonyl group), k represents 0 or 1, and A ₁ R ₃ — (CHR ₀ ) _m — (B ₂ —B ₃ ) _{m ′} — group {R ₃ is a hydrogen atom, a halogen atom or an R ₂ —B ₁ — group (R ₂ and B ₁ are Represents a C1-C10 alkyl group, or a C2-C10 alkenyl group, or a C2-C10 alkynyl group, which may be substituted with the same meaning as above. ₀ represents a hydrogen atom, C1-C10 alkyl or C2-C10 haloalkyl group, m represents 0 or 1, _{B 2} represents a single bond, oxy group, thio group, or -N _((O) n R _1. ') - group _{(R 1'} are identical or different phase and _{R 1,} it represents the same meaning as _{R 1,} n denotes the representative) 0 or 1, _{B 3} represents a carbonyl group, a thiocarbonyl Represents a group or a sulfonyl group, m ′ represents 0 or 1, and when B ₃ is a sulfonyl group, m is 0 and R ₃ is not a hydrogen atom. }, And k ′ represents 0 or 1. }, And R ₄ represents a C1-C10 alkylene group. _{_{However, R 0 'R 0''}} N-R 4 - group _{(R 0'} and R _{0 ''} is different from _{R 0} and same or different, represent the same meaning as _{R 0,} _{R 4} is the same Represents the meaning of. _], D 2 -R ₄ - group _{[D 2} is a cyano _{_{group, R 1 R 1 'NC (}} = N- (O) n -A 1) - group _{_{(R 1, R 1',}} n, and _{A 1} Represents the same meaning as described above.), Represents an A ₁ N═C (—OR ₂ ) — group (A ₁ and R ₂ represent the same meaning as described above) or an NH ₂ —CS— group. , R ₄ represents the same meaning as described above. ], D ₃ -R ₄ -group {D ₃ represents a nitro group or R ₁ OSO ₂ -group (R ₁ represents the same meaning as described above), and R ₄ represents the same meaning as described above. To express. } Or R ₁ OSO ₂ — group (R ₁ represents the same meaning as described above).
(2) Group B:

(A) -Group [In (a), E ₁ and E ₁ ′ represent a methylene group which may be substituted with a C1-C10 alkyl group or a C1-C10 alkoxy group, or a carbonyl group. However, E ₁ and E ₁ ′ are not simultaneously carbonyl groups. E ₂ is oxy, thio, sulfinyl group, a sulfonyl group or a -NR 1 _'- group (R _1'. Is that the represent the same meaning as) that is substituted may be C2-C10 alkylene group, or , oxy, thio, sulfinyl group, a sulfonyl group or a -NR 1 _'- group (R _1'. is representative of the same meaning as) represents may be substituted with C3-C10 alkenylene group, R ₁ Represents the same meaning as described above. ]
It is.
(3) Group C: halogen atom, R ₂ —B ₁ — group (R ₂ and B ₁ are as defined above), D ₄ —R ₄ — group [D ₄ is a hydroxyl group or A ₁ —O— represents a group (A ₁ represents the same meaning as described above), and R ₄ represents the same meaning as described above. ], _{D 5} - group _[D 5 _{is, O = C (R 3)} - group _{(R 3} represents the same meaning as _{_{above.), A 1 - (O}} ) n -N = C (R 3) A group (A ₁ , n and R ₃ are as defined above), R ₁ —B ₀ —CO—R ₄ — (O) _n —N═C (R ₃ ) — group {R ₁ , R ₄ , n and R ₃ represent the same meaning as described above, and B ₀ represents an oxy group, a thio group, or a —N ((O) _m R ₁ ′)-group (R ₁ ′ and m Represents the same meaning as }, D ₂ —R ₄ — (O) _n —N═C (R ₃ ) — group (D ₂ , R ₄ , n and R ₃ represent the same meaning as described above) or R ₁ A ₁ N —N═C (R ₃ ) — group (wherein R ₁ , A ₁ and R ₃ represent the same meaning as described above). ], R ₁ A ₁ N—O—R ₄ — group (R ₁ , A ₁ and R ₄ represent the same meaning as described above), R ₁ (A _1- (O) _n —) N— group (R ₁ , A ₁ and n represent the same meaning as described above), D ₂ -group (D ₂ represents the same meaning as described above) or D ₃ -group (D ₃ represents the same as above. C2-C10 alkenyl group substituted with the same meaning.
(4) Group D:

(b) -R ₄ -group [In (b), G ₁ , G ₂ , G ₄ and G ₅ are methylene groups bonded to adjacent atoms by a single bond, which may be substituted with methyl groups, or Represents a methine group which may be substituted with a methyl group connected to a neighboring atom by a double bond, and G ₃ represents a single bond, a double bond, or a methyl group, an oxy group, a thio group, a sulfinyl group , A sulfonyl group or a —NR ₁ — group (R ₁ represents the same meaning as described above), or a C1-C10 alkylene group, or a methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group Represents a C2-C10 alkenylene group which may be substituted with a group or a —NR ₁ — group (R ₁ represents the same meaning as described above), and R ₄ represents the same meaning as described above. ],

(C) -R ₄ -group (in (c), J ₁ , J ₂ and J ₃ are the same or different and represent a methine group which may be substituted with a methyl group or a nitrogen atom, and R ₄ represents Represents the same meaning as described above), a halogen atom, an R ₂ —B ₁ —R ₄ — group (wherein R ₂ , B ₁ and R ₄ represent the same meaning as described above), D ₄ —R _4. A group (D ₄ and R ₄ have the same meaning as described above), a D ₅ group (D ₅ has the same meaning as described above), a D ₁ -R ₄ -group (D ₁ and R ₄ represents the same meaning as described above), D ₂ -group (D ₂ represents the same meaning as described above) or D ₃ -R ₄ -group (D ₃ and R ₄ represent C2-C10 alkynyl group substituted with the same meaning.
(5) Group E: A ₂ —CO—R ₅ — group. However, when A ₂ is a hydroxyl group, R ₅ is not a vinylene group.
_{[A 2} is,
(i) A ₃ -B ₄ -group {A ₃ is a hydrogen atom, a C1-C10 alkyl group, a C2-C10 haloalkyl group, or a C2-C10 alkenyl group optionally substituted with a halogen atom, Or a C3-C10 alkynyl group optionally substituted with a halogen atom, or R _a- (R ₄ ) _m -group (R _a is a halogen atom, a C1-C10 alkyl group, a C1-C10 alkoxy group or a nitro group; Represents a phenyl group, a pyridyl group, a furyl group or a thienyl group which may be substituted with R ₄ and m have the same meaning as described above.) Or (b) -R ₄ -group ((b) And R ₄ represent the same meaning as described above.), (C) -R ₄ — group ((c) and R ₄ represent the same meaning as described above), R ₂ —B ₁ —R _4. - group _(R 2, _{B 1} and _{R 4} represent the same _meanings.), D ₄ -R 4 - group _{(D 4} and _{R 4} Represents the same meaning), _{D 5} -. Group _{(D 5} represents the same _meaning), D 1 -R ₄ -. Group _{(D 1} and _{R 4} are the same meaning the represented), _{D 2} -. group _{(D 2} represents the same _{_{meaning), D 3 -R 4 -.}} . group _{(D 3} and _{R 4} represent the same meanings as the above) or a ₄ -SO ₂ -R ₄ - group _{{a 4} are (b) - group, (c) ((b) represents the same meanings.) - group ((c), the same Or R ₁ R ₁ ′ N-group (R ₁ and R ₁ ′ represent the same meaning as described above), and R ₄ represents the same meaning as described above. } Represents a C1-C10 alkyl group substituted with
B ₄ represents an oxy group, a thio group, or a —N ((O) _m R ₁ ) — group (where R ₁ and m represent the same meaning as described above). However, when B ₄ is a thio group, A ₃ is not a hydrogen atom. },
(ii) R ₁ —B ₄ —CO—R ₄ —B ₄ ′ — group (R ₁ , B ₄ and R ₄ have the same meaning as described above, and B ₄ ′ is the same as or different from B _4. represents _{B 4} same meaning as the proviso that when _{B 4} is a thio group, _{R 2} is not hydrogen atom) or _{_{_{D 2 -R 4 -B 4 -.}}} . group _(D 2, _{R 4} and _{B 4} is Represents the same meaning as described above).
(iii) R ₂ —SO ₂ —NR ₁ — group (R ₂ represents the same meaning as described above, except for a hydrogen atom; R ₁ represents the same meaning as described above),
(iv) (b) -group ((b) represents the same meaning as described above),
(v) (c) -group ((c) represents the same meaning as described above) or
(vi) R ₁ A ₁ N—NR ₁ ′ -group (R ₁ , A ₁ and R ₁ ′ have the same meaning as described above), and R ₅ may be substituted with a halogen atom. A C2-C10 alkenylene group or a C2-C10 alkynylene group is represented. ]
(6) F _Group: A 5 _-B 5 -R ₆ - group _{[A 5} is _{D 4} - group (. _{D 4} may represent the same meaning as described above), _{D 1} - group _{(D 1,} the represents the same meaning as), _{D 3} -. group _{(D 3,} the representative of the same meaning as) or _a 4 -SO ₂ -. group _{(a 4} is a representative) the same meaning as above. A substituted C2-C10 alkyl group, or an R ₂ —B ₁ — group (R ₂ and B ₁ are as defined above), a D ₂ — group (D ₂ is as defined above); ), D ₅ -group (D ₅ represents the same meaning as described above) or A ₂ —CO— group (A ₂ represents the same meaning as described above) substituted with C 1-. Represents a C10 alkyl group, and B ₅ represents a B ₁ -group (B ₁ represents the same meaning as described above) or a -NA ₁ -group (A ₁ represents the same meaning as described above). , _{R 6} is a single It represents a case or C1-C10 alkylene group. ]
It is.
(7) G _Group: A ₆ _-B 5 -R 6 - group _{[A 6} are (a) -R ₄ - group (. (A) and _{R 4} represents the same meaning as above), or, C2-C10 alkenyl group, C2-C10 alkynyl group, halogen atom, R ₂ -B ₁ -group (R ₂ and B ₁ are as defined above), D ₅ -group (D ₅ represents the same meaning as described above), D ₂ -group (D ₂ represents the same meaning as described above) or A ₂ -CO- group (A ₂ represents the same meaning as described above). ) -Substituted C2-C10 alkenyl group, or a halogen atom, an R ₂ -B ₁ -group (R ₂ and B ₁ have the same meaning as described above), a D ₅ -group (D ₅ is , D ₂ -group (D ₂ represents the same meaning as described above) or A ₂ —CO— group (A ₂ represents the same meaning as described above). A C2-C10 alkynyl group substituted with or (b) -group ((b) represents the same meaning as described above), (c) -group ((c) represents the same meaning as described above. represented), _{D 4} -. group _{(D 4,} the representative of the same meaning as), _{D 1} -. group _{(D 1,} the representative of the same meaning as) or _{D 3} -. group _{(D 3} is , C3-C10 alkenyl group substituted with representing) the same meaning as above, or, _{D 4} -. group _{(D 4} represents the same meaning as above), _{D 1} -. group _{(D 1} is . the represents the same meaning as) or D ₃ -. group (D ₃ represents a C3-C10 alkynyl group substituted with representing) the same meaning as above, B ₅ and R ₆ are the same Represents the meaning of ]
It is.
(8) Group H:
D ₂ —N (— (O) _n —A ₁ ) —R ₆ — group (D ₂ , n, A ₁ and R ₆ are as defined above), D ₂ — group (D ₂ is Represents the same meaning as described above, except for a cyano group.), R ₁ (R ₁ ′ (O) _n ) N—CR ₁ ″ = N—R ₆ — group (R ₁ , R ₁ ′, n and _{R 6} represent the same meanings, R _{1 ''} are the same or different phase and _{R 1,} represents the same meaning as _{_{_{R 1), R 1 -.}}} (O) n -N = CR ₁ _'-NR 2 -R ₆ - group _{_{(R 1, n, R 1}} '., R 2 and _{R 6} represent the same meaning as described _{_{above), R 2 -B 3 -NR 1}} -CO-NR 1 '-R ₆ -group (R ₂ , B ₃ , R ₁ , R ₁ ' and R ₆ represent the same meaning as described above), D ₂ -CO-NR ₁ -R ₆ -group (D ₂ , R ₁ and _{R 6} represent the same meanings as the above. Or _{_{_{A 2 -COCO-NR 1 -R 6}}} - group _(A 2, _{R 1} and _{R 6} represent the same meanings as the above.)
It is.
(9) Group I:
_{_{_{A 7 -B 6 -N ((O}}} ) n R 1) -R 6 - group _{[A 7} is optionally substituted C2-C10 alkenyl group with a halogen atom, C2-C10 alkynyl group, C3-C10 haloalkynyl A group, R ₂ -B ₁ -R ₄ -group (R ₂ , B ₁ and R ₄ are as defined above), D ₄ -R ₄ -group (D ₄ and R ₄ are represents the same _meaning), D 5 -R ₄ -. group _{(D 5} and _{R 4} represents the same _meaning), D 1 -R ₄ -. group _{(D 1} and _{R 4,} the a Represents the same meaning.), (B) -R ₄ -group ((b) and R ₄ represent the same meaning as described above), (c) -R ₄ -group ((c) and R ₄ Represents the same meaning as described above), D ₂ -R ₄ -group (D ₂ and R ₄ represent the same meaning as described above), D ₃ -R ₄ -group (D ₃ and R ₄ Means the same as above _{_{Be), A 4 -SO 2 -R 4}} -. Group _{(A 4} and _{R 4} represents the same meaning) or _A 2 _{-CO-R 4} -. Group _{(A 2} and _{R 4} are the And B ₆ represents a carbonyl group or a thiocarbonyl group, and n, R ₁ and R ₆ represent the same meaning as described above. _{_{], A 8 -CS-N (}} (O) n R 1) -R 6 - group _{[A 8} is a hydrogen atom, or represents a optionally substituted C1-C10 alkyl group with a halogen atom, n, R ₁ and R ₆ represent the same meaning as described above. ],
_{_{_{A 7 '-B 2' -B 3}}} -N ((O) n R 1) -R 6 - group _{[A 7} 'is optionally substituted C3-C10 alkenyl group with a halogen atom, is substituted with a halogen atom and it may be C3-C10 alkynyl _{_{_{group, R 2 -B 1 -R 4 '}}} - group _{(R 2} and _{B 1} represent the same meaning as, _{R 4'} represents a C2-C10 alkylene group.) , _D ₄ -R 4 '- group _{(D 4} and _{R 4'} represents the same meaning _{_{as.), D 1 -R 4 '}} - group _{(D 1} and _{R 4',} wherein the same meaning ), (B) -R ₄ '-group ((b) and R ₄ ' represent the same meaning as described above), (c) -R ₄ '-group ((c) and R ₄ 'Represents the same meaning as described above), D ₂ -R ₄ -group (D ₂ and R ₄ represent the same meaning as described above), D ₃ -R ₄ ' -group (D ₃ and R 4 _'represents the same meaning as above.) The _A 2 _{-CO-R 4} - group (. _{A 2} and _{R 4} represent the same meanings as the above) represents, _{B 2} 'is an oxy group, thio group, or -N ((O) _n' R ₁ ′)-group (where n ′ is the same as or different from n and represents the same meaning as n, and R ₁ ′ represents the same meaning as described above), B ₃ , n, R ₁ and R ₆ represents the same meaning as described above. _{_{], A 8 '-B 2'}} -CS-N ((O) n R 1) -R 6 - group _{[A 8} 'represents a C1-C10 alkyl or C2-C10 haloalkyl group, _{B 2'} is , And the same meaning as described above, and n, R ₁ and R ₆ represent the same meaning as described above. _{_{], A 8 '-S-B}} 3' -N ((O) n R 1) -R 6 - group _{_{[A 8 ', n, R}} 1 and _{R 6} represent the same meanings as above, _{B 3} 'Represents a carbonyl group or a sulfonyl group. ] Or _{_{_{A 7 '' -SO 2 -N (}}} (O) n R 1) -R 6 - group [A _{7 ''} is, C2-C10 alkenyl group, C3-C10 alkenyl group substituted with a halogen atom, a halogen optionally substituted C3-C10 alkynyl group _{_{_{atom, R 2 -B 1 -R 4 '}}} - group _(R 2, _{B 1} and _{R 4'.} is representing the same meaning as _above), D 4 -R ₄ '- group _{(D 4} and _{R 4'} represents the same _meaning.), D 5 -R ₄ - group (. _{D 5} and _{R 4} represent the same meaning as described above), _{D 1} -R ₄ '-group (D ₁ and R ₄ ' are as defined above), (b) -R ₄ '-group ((b) and R ₄ ' are as defined above) ), (C) -R ₄ '-group ((c) and R ₄ ' represent the same meaning as described above), D ₂ -R ₄ -group (D ₂ and R ₄ are as defined above. represents the same meaning.), _NO 2 -R - group _{(R 4,} the representative of the same meaning as.) Or _A 2 _{-CO-R 4} - group (. _{A 2} and _{R 4} represent the same meanings as the above) represents, n, _{R 1} And R ₆ represent the same meaning as described above. ]
It is.
(10) Group J: A ₇ -CO— group (A ₇ represents the same meaning as described above), or A ₉ -CS- group (A ₉ represents A ₇ or A ₈ ), Or A ₉ ′ (O) _m N═C (A ₉ ) — group (A ₉ ′ represents A ₇ ′ or A ₈ ′, and m and A ₉ represent the same meaning as described above), Or D ₂ —CO— group (D ₂ represents the same meaning as described above), A ₂ —COCO— group (A ₂ represents the same meaning as described above), or A _9. -CO-B ₁ '-R ₆ -group (A ₉ and R ₆ represent the same meaning as described above, B ₁ ' represents an oxy group or a thio group, provided that B ₁ 'is an oxy group. , A ₉ is not A ₈ ), or A ₉ -CS-B ₁ ′ -R ₆ -group (A ₉ , B ₁ ′ and R ₆ represent the same meaning as described above). _{_{or, A 7 '' -SO 2 -B}} 1 ' R ₆ - group _{_{(A 7 '', B 1}} ' and _{R 6} represent the same meanings as the above.), _{_{_{Or, A 8 -SO 2 -B 1'}}} -R 6 - group _(A 8, B ₁ ′ and R ₆ represent the same meaning as described above, provided that A ₈ cannot be a hydrogen atom.) Or A ₉ ′ -B ₂ ′ -B ₃ -B ₁ ′ —R ₆ — group (A ₉ ′, B ₂ ′, B ₃ , B ₁ ′ and R ₆ represent the same meaning as described above), or (b) -group ((b) is It is a C2-C10 alkenyl group substituted with the same meaning as described above) or a (c) -group (wherein (c) represents the same meaning as described above).
(11) Group K: A ₁₀ -N ((O) _n R ₁ ) —CO—R ₆ — group [A ₁₀ is a hydrogen atom (where n is not 0), A ₇ ″ -SO _2. -Group (A ₇ ″ represents the same meaning as described above), A ₈ —SO ₂ — group (A ₈ represents the same meaning as described above, provided that A ₈ is not a hydrogen atom. .), _{a 9} 'O- group _{(a 9'} represents the same meaning where, n is not a _{1), a 9.. '} - group _{(a 9'} has the same meaning It represents the proviso that when n is 0, except _{_{a 8 '), R 2 OCH}} 2 -.. group _{(R 2} represents the same meaning as _{above), a 2 -CO-R 4} -. group (a ₂ and R ₄ represent the same meaning as described above) or an A ₂ —CO—CH (CH ₂ CO—A ₂ ) — group (A ₂ represents the same meaning as described above), and n , _{R 1} and _{R 6} are the Represent the same meaning. ]
It is.
(12) L _group: - (. Here, n is not _{_{_{0) A 10 '-N ((}}} O) n R 1) -SO 2 -R 6 group _{[A 10'} is a hydrogen atom, _{A 9} 'O - group _{(a 9} 'represents the same meaning where, n is not a _{1..), a 9'} -. group _{(a 9} 'represents the same meaning as above where, n is 0 _. when, except for _{a 8} _'), R 2 -CO- group _{(R 2} represents the same _{meaning), a 2 -CO-R 4} -. group _{(a 2} and _{R 4} are the And A ₂ —CO—CH (CH ₂ CO—A ₂ ) — group (A ₂ represents the same meaning as described above), and n, R ₁ and R ₆ represent Represents the same meaning as described above. ] A ₉ ″ R ₁ N—SO ₂ —N ((O) _n R ₁ ′) —R ₆ — group [A ₉ ″ is a hydrogen atom or A ₉ ′ -group (A ₉ ′ R ₁ , n, R ₁ ′ and R ₆ represent the same meaning as described above. ] Or _{_{(b) -SO 2 -N ((}} O) n R 1 ') -R 6 - group _{[(b), n, R} 1' and _{R 6} represent the same meanings. ]
It is.
(13) M _{_{group: R 1 (R 2 S)}} C = N-R 6 - group _{_(.} _R 1, R ₂ and _{R 6} represent the same meaning as described _{_{above), R 2 B (R 2}} 'B _{') C = N-R 6} - group _{(R 2} and _{R 6} represent the same meaning, _{R 2'} are identical or different phase and _{R 2,} and _{R 2,} represent the same meaning, B And B ′ are the same or different and represent an oxy group or a thio group.), R ₁ R ₁ ′ N— (R ₂ S) C═N—R ₆ —group (R ₁ , R ₁ ′, R ₂ And R ₆ represent the same meaning as described above.), R ₁ N═C (SR ₂ ) —NR ₂ ′ —R ₆ — group (R ₁ , R ₂ , R ₂ ′ and R ₆ are Represents the same meaning.) Or R ₁ (R ₁ ′ O) N—R ₆ — group (R ₁ , R ₁ ′ and R ₆ represent the same meaning as described above.)
It is.
(14) N _group: (. _{R 1} may represent the same meanings as the above) A 11 -P (= O) (OR 1 ') -R 4 - - group _{[A 11} is _{R 1} group, _{R 1} An O—R ₆ — group (R ₁ and R ₆ are as defined above) or an R ₁ OCO—CHR ₀ — group (where R ₁ and R ₀ are as defined above); R ₁ ′ and R ₄ represent the same meaning as described above. ]
It is.
III. (Y _A ) In _q , Y _A represents a group of the following X group or Y group, q represents 0, 1, 2, or 3, and p (p represents the same meaning as described above). And q are 3 or less, and when q is 2 or more, Y _A is the same or different, and when q is 2 or more, two adjacent same or different Y _A are Z A group may be formed and condensed with the A ring.
(1) Group X: M _a -group [M _a represents an R _b -group (R _b represents a C1-C10 alkyl group optionally substituted with a halogen atom), a halogen atom, a nitro group, a cyano group. , _R c _-B a -R _d - group _{(R c} represents an optionally substituted C1-C10 alkyl group with a halogen atom, _{B a} represents oxy, thio, sulphinyl group or a sulfonyl group, R _d represents a single bond or a C1-C10 alkylene group.), A HO—R _d — group (R _d represents the same meaning as described above), a R _e —CO—R _d — group (R _e Represents a hydrogen atom or a C1-C10 alkyl group which may be substituted with a halogen atom, and R _d represents the same meaning as described above), R _e —CO—O—R _d — group (R _e and _{R d} represent the same meaning), R e O-CO- R d -. group _{(R e} and _{R d} are the same meaning as . Be), HO-CO-CH = CH- _{_{group, R e R e 'N-}} R d - group _{(R e} and _{R e'} are the same or different, _{R e} represents the same meaning as above , R _e ′ represents the same meaning as R _e, and R _d represents the same meaning as described above.), R _e —CO—NR _e ′ —R _d — group (R _e , R _e ′ and R _d represents the same meaning as described above.), R _b O—CO—N (R _e ) —R _d — group (R _b , R _e and R _d represent the same meaning as described above.) , R _e R _e ′ N—CO—R _d — group (R _e , R _e ′ and R _d represent the same meaning as described above), R _e R _e ′ N—CO—NR _e ″ — R _d - group _(R e, _{R e} 'and R _e' 'are the same or different, _{R e} and _{R e'} represents the same meanings, R _{e ''} are the same and _{R e} the meaning, the R _d are the same meaning as _{_{Be), R e R e 'N}} -C (= NR e'') -NR e''.' -R d - group _{_{(R e, R e ',}} R e'' and R _e' '' is, R _e , R _e ′ and R _e ″ have the same meaning as described above, R _e ′ ″ has the same meaning as R _e, and R _d has the same meaning as above. R _b —SO ₂ —NR _e —R _d — group (R _b , R _e and R _d represent the same meaning as described above), R _e R _e ′ N—SO ₂ —. R _d -group (R _e , R _e ′ and R _d represent the same meaning as described above. ), A C2-C10 alkenyl group or a C2-C10 alkynyl group. ].
(2) Y group: M _b -R _d -group [M _b is M _c -group {M _c is M _d -R _d '-group {M _d is M _a -group (M _a is A phenyl group which may be substituted with M _a -group (M _a represents the same meaning as described above), _a pyridyl group which may be substituted with M _a -group (M _a represents a naphthyl group which may be substituted with the same meaning as described above, and (b) -group ((b) represents the same meaning as described above), (c) -group ((c ) Represents the same meaning as described above.),

(D) -group (l is 2, 3 or 4 and B _b represents an oxy group or a thio group) or

(E) - group (. L and _{B b} are representing the same meaning as above) represents, _{R d} 'are different from _{R d} and same or different, represent the same meaning as _{R d.} }. _}, M c -B _a - group _(. _{M c} and _{B a} are representing the same _meaning), M c -CO- group (. _{M c} is representative of the same meaning as above), _{M c} -CO-O- group _{(M c} represents the same meaning _as.), M c O-CO- group _{(M c} represent the same meanings as the _above.), M _{c R} e N- group (M _c and R _e represent the same meaning as described above), M _c —CO—NR _e — group (M _c and R _e represent the same meaning as described above), M _c O—CO —NR _e — group (M _c and R _e represent the same meaning as described above), M _c R _e N—CO— group (M _c and R _e represent the same meaning as described above), _{_{M c R e N-CO-}} NR e '- group _(M c, _{R e} and _{R _e'.} are representative of the same _{meaning), M c R e N-} C (= NR e ') -NR _e ″ -group (M _c , R _e , R _e ′ and R _e ″ represent the same meaning as described above.), M _c —SO ₂ —NR _e — group (M _c and R _e represent the same meaning as described above) or M _c. R _e N—SO ₂ — represents a group (M _c and R _e represent the same meaning as described above), and R _d represents the same meaning as described above. ].
(3) Z group: —Y _a ″ = C (Y _a ) —Y _a ′ — group (Y _a is a C1-C10 alkyl group optionally substituted with a hydrogen atom or a halogen atom, or C1 represents -C10 alkoxy group, Y a _'is an oxy group, or a thio group, or represents a C1-C10 alkyl optionally imino group which may be substituted with a group, Y _a' 'is -N = group or methine . representing the group), C3-C10 alkylene group or a _{_{_{-Y b = Y b '-Y b}}} ''= Y b''' - radical _{_{[Y b, Y b ',}} Y b'' and Y _b' '' Are the same or different and each represents a methine group which may be substituted with _a Ma-group (Ma has the same meaning as described above) or a -N = group. ].
IV. B is
Formula (IV-1)

[Where:
(1) Q _A is a hydroxyl group, (b) -group ((b) represents the same meaning as described above), A ₉ -B ₆ -B _c -group [A ₉ and B ₆ are as defined above. B _c represents an oxy group or —N ((O) _m R ₁ ) — group (m and R ₁ represent the same meaning as described above). However, when A ₉ is a hydrogen atom, B _c is not a sulfonyl group. _{_{], A 7 '' -SO 2}} -B c - group (A _{7 ''} and _{B c} represents the same meaning _{_{as.), A 8 -SO 2 -B}} c - group _{(A 8} and _{B c} Represents the same meaning as described above, provided that A ₈ is not a hydrogen atom.), R ₁ R ₁ ′ N—SO ₂ —B _c — group (R ₁ , R ₁ ′ and B _c are represents the same meaning _{as),. (b) -SO 2} -B c - groups ((b) and _{B c} represent the same meaning as _{_{above), a 9 '-B c -}} . group _{(a 9} 'And B _c represent the same meaning as described above.), D ₅ —R ₄ —B _c — group (D ₅ , R ₄ and B _c represent the same meaning as described above), M _c —. B ₃ -B _c -group (M _c , B ₃ and B _c represent the same meaning as described above) or M _c -B _c -group (M _c and B _c represent the same meaning as described above). .)
(2) _{W A} is an oxygen atom or -NT _A - is a group _{[T A,} a hydrogen atom, _{A 9} '- group _{(A 9'.} Are representing the same meaning as _above), D 5 -R ₄ - A group (D ₅ and R ₄ represent the same meaning as described above) or a M _c -group (M _c represents the same meaning as described above). ]. T _A is a hydrogen atom, A ₉ '-group (A ₉ ' represents the same meaning as described above), D ₅ -R ₄ -group (D ₅ and R ₄ represent the same meaning as described above). Or M _c -group (M _c represents the same meaning as described above).
(3) K _A represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, L _A is a hydrogen atom, C1-C10 alkyl group or M _b - group (M _b represents the same meaning as above .) represents, and _{K a} and _{L a,} C3-C10 alkylene group or _{-C (M a ') = C} (M a'') -C (M a''') = C (M a '' ″) -Groups (M _a ′, M _a ″, M _a ″ ″ and M _a ″ ″ are the same or different and are the same or different from M _a and represent _a hydrogen atom or M _a . ). ]
A group represented by
Formula (IV-2)

Wherein, T _A represents the same meaning, L _B represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (IV-3)

[Wherein, T _A represents the same meaning as described above, and L _C represents a C1-C10 alkyl group. ]
A group represented by
Formula (IV-4)

[Wherein, T _A represents the same meaning as described above. ]
A group represented by
Formula (IV-5)

Wherein, T _A represents the same meanings, K _B is a cyano group or UOCO- group (U represents. A hydrogen atom or a C1-C10 alkyl group);. ]
A group represented by
Formula (IV-6)

Wherein, W _A represents the same meaning, and K _C and L _D, C3-C10 alkylene group, or one or the same or different plurality of Ma- groups (Ma, the same meaning Represents a C4-C10 alkenylene group optionally substituted. ]
A group represented by
Formula (IV-7)

Wherein the _{Q A} and _{W A,} represents the same meaning as, the _{K D} and _{_{_{L E, -V A = V A}}} '-V A''= V A''' - group _{{V A} _{_{, V a ', V a'}} ' and V _a' '' are the same or different, M a _- group (. M _a is that the represent the same meaning as) methine group optionally substituted by a, or , -N = group, and at least one of V _A , V _A ', V _A ″ and V _A ''' represents -N = group. }. ]
A group represented by
Formula (IV-8)

[Wherein, T _A represents the same meaning as described above, Q _B represents a hydroxyl group, and A ₉ -B ₆ -O- group [A ₉ and B ₆ represent the same meaning as described above]. _{_{], A 7 '' -SO 2}} -O- group (A _{7 ''} represents the same meaning _as.), A 8 _-SO 2 -O- group _{(A 8} are the same meaning as above Provided that A ₈ is not a hydrogen atom.), R ₁ R ₁ ′ N—SO ₂ —O— group (R ₁ and R ₁ ′ represent the same meaning as described above), (b) -SO ₂ -O- group ((b) is a. representing the same meaning), _{a 9} '-O- group _{(a 9'} represents the same meaning as _above.), D 5 -R ₄ -O- group _{(D 5} and _{R _4.} representing the same meaning), _{M c} -B 3 -O- group _{(M c} and _{B 3} represent the same meanings as the above.) or M _c —O— group (M _c represents the same meaning as described above). ]
Or a group represented by
Formula (IV-9)

Wherein, U and W _A represent the same meaning as above. ]
Represents a group represented by
However, when A is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:

Formula (V)

[Where:
I. a represents a thiophene ring, furan ring, pyrrole ring, pyrazole ring, 1,2,3-triazole ring, tetrazole ring, isoxazole ring, thiazole ring, pyridazine ring or pyrimidine ring, and X _a is substituted with a cyano group C1-C10 alkyl group substituted with a tetrahydropyran-4-ylidene group, C2-C10 alkenyl group substituted with a halogen atom or a cyano group, or C1-C10 alkoxy A C2-C10 alkenyl group substituted with a carbonyl group, a C3-C10 alkynyl group substituted with a hydroxy group, or an a ₀ -r ₁ -br ₁ ′ -group {a ₀ is a C ₁ -C 10 alkylthio A methyl group substituted with a C1-C10 alkylsulfinyl group, a methyl group substituted with a C1-C10 alkylsulfonyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group _Group, r 2 O-CO- group _{(r 2} represents a C2-C10 alkyl group substituted with C1-C10 alkyl group or a hydroxyl group.), A carboxy group, RR'N-CO- group (r and r ' are the same or different, represent a hydrogen atom or a C1-C10 alkyl group.), a 1 _-NH-CO- group (a ₁ represents a C2-C10 alkyl group substituted with C1-C10 alkoxy group. ), A ₁ '-CO- group (a ₁ ' represents a morpholino group), rr'N-CH ₂ -group (r and r 'represent the same meaning as described above), r _0- . _{_{(O) l -CONH-CH 2}} - group _{(r 0} denotes a C1-C10 alkyl group, l represents 0 or _{1.), r-OCH 2} - group (r is the same meaning as above _{represents.),} r 0 -CO- group _{(r 0} represents the same meaning as above.), a cyano group or a sulfomethyl group, _{r 1} represents a C1-C10 alkylene group r 1 _'represents a single bond or a C1-C10 alkylene group, b represents an oxy group, a thio group, a sulfinyl group, an imino group optionally substituted by a sulfonyl group or a methyl group. }, _Or, a 2 -y-CO-NH- group _{(a 2} represents a C2-C10 alkyl group substituted with C1-C10 alkoxy group, y represents an oxy group or an imino group.), Or , rO-COCO-NH- group (r represents the same meaning as above.), _{or, a} 3 -z-NH- group _{(a 3} is C2-C10 alkenyl group, or, C1-C10 alkoxy group Represents a C1-C10 alkyl group substituted with a C1-C10 alkoxycarbonyl group, a carboxy group or a cyano group, and z represents a carbonyl group or a sulfonyl group) or an a ₄ -Nr′CO— group {a _4, C1-C10 alkoxy group, or a C3-C10 alkenyloxy group, or, r 0 _-SO 2 _- group (. r ₀ represents the same meaning as), or a hydroxyl or C1-C10 alkoxy A C2-C10 alkyl group substituted with a group, or an r ₀ r ₀ 'N- group (where r ₀ is the same as defined above) Represents one meaning of, _{r 0} 'is different from _{r 0} the same or different, C2-C10 alkyl group substituted with represents the same meaning as _{r 0.),} Or, and rO-CO- group (r is Represents the same meaning as described above), a C1-C10 alkyl group substituted with a cyano group or an aminocarbonyl group, or an rO—CO— (rO—COCH ₂ ) CH— group (r is as defined above). And r ′ represents the same meaning as described above. }, _Or, a 5 -NHSO ₂ - group (. _{A 5} represents a C2-C10 alkyl group substituted with C1-C10 alkoxy group), _or, r 0 ON = CH- group _{(r 0,} the Or r ₀ NHCSNH- group (r ₀ represents the same meaning as described above), or r ₀ NHC (-Sr ₀ ') = N- group (r ₀ and r ₀ ′ represents the same meaning as described above.) or (rO) ₂ P (═O) CH ₂ — group (r represents the same meaning as described above), and p represents 0. , 1, 2 or 3 and when p is 2 or more, X _a is the same or different,
Y _a is a halogen atom, a C1-C10 alkyl group that may be substituted with a halogen atom, a C1-C10 alkyl group that may be substituted with a C1-C10 alkoxy group, or a C2-C10 alkenyl group, Or a C2-C10 alkynyl group, a 2-oxo-oxazolidin-3-yl group, a [1,3] dioxolan-2-yl group, or a C1-C10 alkoxy group substituted with a morpholino group, or , A ₀ '-b'- group (a ₀ ' represents a C1-C10 alkyl group which may be substituted with a halogen atom, and b 'represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group). Or a nitro group, a cyano group, or an rO—CO— group (where r represents the same meaning as described above), or an r ₀ r ₀ ′ N-group (r ₀ and r ₀ ′ are represents the same meaning as.), _or, r 0 CO-NH- group _{(r 0,} the same Meanings.), _Or, _{r 0} r 0 'NCONH- group _{(r 0} and _{r 0',} the. Represents the same meaning as), or, Rr'NCO- group (r and r 'are, Represents the same meaning as described above), or represents a hydroxyl group, q represents 0, 1, 2 or 3, and when q is 2 or more, Y _a is the same or different and q is 2 or more. In some cases, adjacent Y _a may be condensed with a ring to form a 4,5,6,7-tetrahydrobenzo [b] thiophene ring.
II. b is
Formula (V-1)

Wherein, _{Q a} _is r a -O- group _{{r a} is a hydrogen atom, or, C1-C10 alkyl group, or, C3-C10 alkenyl group, or, C3-C10 alkynyl group, or, _{r 0} r ₀ 'N-CH ₂ - group _{(r 0} and _{r 0'} represents the same meaning as.), Roch ₂ - group _(. r is representative of the same meaning as _above), r 0 -CO - group (. r ₀ is representative of the same meaning), C1-C10 alkoxycarbonyl group, a carboxy group, C1-C10 alkyl group substituted with aminocarbonyl group or a cyano group, or, r ₃ -r ₁ -Represents a group (wherein r ₃ represents a phenyl group or a pyridyl group, and r ₁ represents the same meaning as described above). }, Or piperidino group, morpholino group, or r ₄ r ₄ ′ N-group (where r ₄ and r ₄ ′ are the same or different, a hydrogen atom, a C1-C10 alkyl group, or C 3 -C10 alkenyl group, or C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with C1-C10 alkoxy group. However, not hydrogen atoms at the same time.) represents, W _a is , oxygen atom or -NT _a - group _{[T a} is _{r b} - group _{(r b} may be the same or different phases and _{r a,} represents the same meaning as _{r a.)} or _{r 3} '- group _{(r 3} 'differs r ₃ and same or different, represent a representative.) the same meaning as r _3. Represents], K _a represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, a L _a represents a hydrogen atom or a C1-C10 alkyl group, a and K _a and L _a, C3-C10 alkylene group Alternatively, it may form a 1,3-butadienylene group. ]
A group represented by
Formula (V-2)

Wherein, T _a represents the same meaning as above, L _b represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (V-3)

Wherein, T _a represents the same meaning as, L _c represents a C1-C10 alkyl group. ]
A group represented by
Formula (V-4)

Wherein, T _a represents the same meaning as above. ]
A group represented by
Formula (V-5)

Wherein, T _a represents the same meaning as above, K _b is cyano group or UOCO- group (U represents. A hydrogen atom or a C1-C10 alkyl group);. ]
A group represented by
Formula (V-6)

[Wherein W _a represents the same meaning as described above, and K _c and L _{d form} a C3-C10 alkylene group or a C4-C10 alkenylene group. ]
A group represented by
Formula (V-7)

Wherein, _{Q a} and _{W a} represents the same meaning as, the _{K d} and _{_{_{L e, -V a = V a}}} '-V a''= V a''' - group _{(V a} , V _a ′, V _a ″ and V _a ″ are the same or different and represent a methine group or —N = group, and V _a , V _a ′, V _a ″ and V _a ″ At least one of-represents -N = group. ]
A group represented by
Formula (V-8)

Wherein, _{T a} represents the same meaning as, _{Q b} _is r a -O- group _{(r a} represents. The same meanings as the above) represents a. ]
Or a group represented by
Formula (V-9)

[Wherein U and W _a represent the same meaning as described above. ]
Represents a group represented by
However, when a is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:

Formula (VI)

Wherein, a1 is a thiophene ring, a furan ring, represents a pyrrole ring or a thiazole ring, _{X a1} _{_{_{is, a 0 '-r 1 -b 0}}} -r 1' - groups _{{a 0} 'is and rO-CO- group (r represents a hydrogen atom or a C1-C10 alkyl _{_{group.), r 0 r 0 '}} N-CH 2 - group _{(r 0} and _{r 0'} are the same or different and represent a C1-C10 alkyl group ) Or a hydroxymethyl group, r ₁ represents a C1-C10 alkylene group, r ₁ ′ represents a single bond or a C1-C10 alkylene group, and b ₀ represents an oxy group, a thio group, or a sulfinyl group. Represents an imino group substituted with a group, a sulfonyl group or one methyl group. }, _Or, a 2 -O-CO-NH- group _{(a 2} is. Represents a C2-C10 alkyl group substituted with C1-C10 alkoxy group), or, _{a 3} '-CO-NH- group ( a 3 _'is. represents a C1-C10 alkyl group substituted with C1-C10 alkoxy group), or, a _4' -NRCO- group (a 4 _'is substituted with a hydroxyl or C1-C10 alkoxy group A C2-C10 alkyl group, or
Represents a C1-C10 alkyl group substituted with an aminocarbonyl group, and r represents the same meaning as described above. ) And b1 is
Formula (VI-1)

( _Wherein , r _b1 represents a hydrogen atom or a C1-C10 alkyl group, K _a1 represents a hydrogen atom, L _a1 represents a C1-C10 alkyl group, and K _a1 and L _a1 represent 1, (May form 3-butadienylene group.)
A group represented by
Formula (VI-7)

(Wherein, r _b1 represents the same meaning as described above.)
Or a group represented by
Formula (VI-8)

(Wherein, r _b1 represents the same meaning as described above.)
Represents a group represented by
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:

Formula (VII)

Wherein, a1 is a thiophene ring, a furan ring, represents a pyrrole ring or a thiazole _{ring, X a1} _{_{_{is, a 0 '-r 1 -b 0}}} -r 1' - groups _{{a 0} _'is r 0 O- CO-group (r ₀ represents a C1-C10 alkyl group), r ₀ r ₀ 'N-CH ₂ -group (r ₀ and r ₀ ' are the same or different, and r ₀ 'represents r ₀ It represents the same meaning as.), or represents a hydroxymethyl group, r ₁ represents a C1-C10 alkylene group, r 1 _'represents a single bond or a C1-C10 alkylene group, b ₀ is oxy Represents an imino group substituted by a group, a thio group, a sulfinyl group, a sulfonyl group or one methyl group. }, _Or, a 2 -O-CO-NH- group _{(a 2} is. Represents a C2-C10 alkyl group substituted with C1-C10 alkoxy group), or, _{a 3} '-CO-NH- group ( a 3 _'is. represents a C1-C10 alkyl group substituted with C1-C10 alkoxy group), or, a _4' -NRCO- group (a 4 _'is substituted with a hydroxyl or C1-C10 alkoxy group A C2-C10 alkyl group, or
Represents a C1-C10 alkyl group substituted with an aminocarbonyl group, and r represents a hydrogen atom or a C1-C10 alkyl group. ). Provided that when a1 is thiophene ring, at the same time, a 0 _'a dimethyl aminomethyl group or a hydroxymethyl group, at the same time, a r ₁ is methylene group, simultaneously, r _1' is a single bond, At the same time, b ₀ is not an oxy group, a thio group or an imino group substituted with one methyl group, and when a 1 is a thiophene ring, a ₀ ′ is a methoxycarbonyl group, , R ₁ is a methylene group, and at the same time, r ₁ ′ is a single bond, and b ₀ is not a thio group at the same time. ]
An aldehyde derivative represented by

Formula (VIII)

Wherein, a1 is a thiophene ring, a furan ring, represents a pyrrole ring or a thiazole _{ring, X a1} _{_{_{is, a 0 '-r 1 -b 0}}} -r 1' - groups _{{a 0} _'is r 0 O- CO-group (r ₀ represents a C1-C10 alkyl group), r ₀ r ₀ 'N-CH ₂ -group (r ₀ and r ₀ ' are the same or different, and r ₀ 'represents r ₀ It represents the same meaning as.), or represents a hydroxymethyl group, r ₁ represents a C1-C10 alkylene group, r 1 _'represents a single bond or a C1-C10 alkylene group, b ₀ is oxy Represents an imino group substituted by a group, a thio group, a sulfinyl group, a sulfonyl group or one methyl group. }, _Or, a 2 -O-CO-NH- group _{(a 2} is. Represents a C2-C10 alkyl group substituted with C1-C10 alkoxy group), or, _{a 3} '-CO-NH- group ( a 3 _'is. represents a C1-C10 alkyl group substituted with C1-C10 alkoxy group), or, a _4' -NRCO- group (a 4 _'is substituted with a hydroxyl or C1-C10 alkoxy group A C2-C10 alkyl group, or
Represents a C1-C10 alkyl group substituted with an aminocarbonyl group, and r represents a hydrogen atom or a C1-C10 alkyl group. ). Provided that when a1 is thiophene ring, at the same time, a 0 _'a dimethyl aminomethyl group or a hydroxymethyl group, at the same time, a r ₁ is methylene group, simultaneously, r _1' is a single bond, At the same time, b ₀ is not an oxy group, a thio group or an imino group substituted with one methyl group, and when a 1 is a thiophene ring, a ₀ ′ is a methoxycarbonyl group, , R ₁ is a methylene group, and at the same time, r ₁ ′ is a single bond, and b ₀ is not a thio group at the same time. ]
An aldehyde derivative represented by formula (VIII ′)

[Wherein b1 is
Formula (VIII-1)

( _Wherein , r _b1 represents a hydrogen atom or a C1-C10 alkyl group, K _a1 represents a hydrogen atom, L _a1 represents a C1-C10 alkyl group, and K _a1 and L _a1 represent 1, (May form 3-butadienylene group.)
A group represented by
Formula (VIII-7)

(Wherein, r _b1 represents the same meaning as described above.)
Or a group represented by
Formula (VIII-8)

(Wherein, r _b1 represents the same meaning as described above.)
Represents a group represented by ]
Characterized by reacting with a compound of formula (VIII ″)

[Wherein, a1, X _a1 and b1 represent the same meaning as described above. ]
The manufacturing method of the cinnamoyl compound shown by these.

Formula (I ')

(E ₀ ) -group {e ₀ is a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a —NR ₁ — group (R ₁ is as defined above), a sulfinyl group or a sulfonyl group. It forms an optionally substituted 5-12 membered hydrocarbon ring. Represents}, _{R d} 'are the same or different and _{R d,} it represents the same meaning as _{R d.} }. _{}, M} c0 -B _a - group _{_(. M c0} and _{B a} are representing the same _meaning), M c0 -CO- group _{(. M c0} is representative of the same meaning _{as), M c0} -CO-O- group (M _c0 represents the same meaning as described above), M _c0 O-CO- group (M _c0 represents the same meaning as described above), M _c0 R _e N- group (M _c0 and R _e represent the same meaning as described above), M _c0 —CO—NR _e — group (M _c0 and R _e represent the same meaning as described above), M _c0 O—CO —NR _e — group (M _c0 and R _e represent the same meaning as described above), M _c0 R _e N—CO— group (M _c0 and R _e represent the same meaning as described above), _{_{M c0 R e N-CO-}} NR e '- group _(M c0, _{R e} and _{R _e'.} are representing the same meaning _{as), M c0 R e N-} C (= N _{_e ')} -NR _e' '- group _{_{_{(M c0, R e, R}}} e' and R _{e ''} represents the same _{_{meaning), M c0 -SO 2 -NR e}} -. group _{(M c0} And R _e represent the same meaning as described above) or a M _c0 R _e N—SO ₂ — group (M _c0 and R _e represent the same meaning as described above), and R _d represents the above Represents the same meaning as ].
(3) Z ₀ group: having halogen atom, C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group It may be a 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring and a group condensed with the α ring.
II. β 'is
Formula (I'-1)

[Where:
(1) _Qα represents an optionally substituted hydroxyl group or an optionally substituted amino group.
(2) W _α represents an oxygen atom or a —NT _α — group (T _α represents a hydrogen atom or a substituent on a nitrogen atom).
(3) K _α and L _α are the same or different and represent a hydrogen atom or a substituent on a carbon atom, and K _α and L _α are a C3-C10 alkylene group which may have a substituent. Alternatively, it may form a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (I'-2)

[Wherein, T _α represents the same meaning as described above, and L _β represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (I'-3)

[Wherein, T _α represents the same meaning as described above, and L _γ represents a C1-C10 alkyl group. ]
A group represented by
Formula (I'-4)

[Wherein, T _α represents the same meaning as described above. ]
A group represented by
Formula (I'-5)

[Wherein, T _α represents the same meaning as described above, and K _β represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (I'-6)

[Wherein W _α represents the same meaning as described above, and K _γ and L _δ represent a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene which may have a substituent. Make a basis. ]
A group represented by
Formula (I'-7)

[Wherein Q _α and W _α represent the same meaning as described above, and K _δ and L _ε represent -V _α = V _α '-V _α ″ = V _α ''' -group (V _α , V _α ′, V _α ″ and V _α ″ ″ are the same or different and each represents an optionally substituted methine group or —N = group, and V _α , V _α ′, V _α ″ And at least one of V _α ′ ″ represents —N = group. ]
A group represented by
Formula (I'-8)

[Wherein, T _α represents the same meaning as described above, and Q _β represents a hydroxyl group which may be substituted. ]
Or a group represented by
Formula (I'-9)

[Wherein W _α represents the same meaning as described above. ]
Represents a group represented by
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A composition for inhibiting transcription of an extracellular matrix gene, comprising a cinnamoyl compound represented by the formula (1) and an inert carrier.

Formula (II ')

(E ₀ ) -group {e ₀ is a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a —NR ₁ — group (R ₁ is as defined above), a sulfinyl group or a sulfonyl group. It forms an optionally substituted 5-12 membered hydrocarbon ring. Represents}, _{R d} 'are the same or different and _{R d,} it represents the same meaning as _{R d.} }. _{}, M} c0 -B _a - group _{_(. M c0} and _{B a} are representing the same _meaning), M c0 -CO- group _{(. M c0} is representative of the same meaning _{as), M c0} -CO-O- group (M _c0 represents the same meaning as described above), M _c0 O-CO- group (M _c0 represents the same meaning as described above), M _c0 R _e N- group (M _c0 and R _e represent the same meaning as described above), M _c0 —CO—NR _e — group (M _c0 and R _e represent the same meaning as described above), M _c0 O—CO —NR _e — group (M _c0 and R _e represent the same meaning as described above), M _c0 R _e N—CO— group (M _c0 and R _e represent the same meaning as described above), _{_{M c0 R e N-CO-}} NR e '- group _(M c0, _{R e} and _{R _e'.} are representing the same meaning _{as), M c0 R e N-} C (= N _{_e ')} -NR _e' '- group _{_{_{(M c0, R e, R}}} e' and R _{e ''} represents the same _{_{meaning), M c0 -SO 2 -NR e}} -. group _{(M c0} And R _e represent the same meaning as described above) or a M _c0 R _e N—SO ₂ — group (M _c0 and R _e represent the same meaning as described above), and R _d represents the above Represents the same meaning as ].
(3) Z ₀ group: having halogen atom, C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group It may be a 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring and a group condensed with the α ring.
II. β 'is
Formula (II'-1)

[Where:
(1) _Qα represents an optionally substituted hydroxyl group or an optionally substituted amino group.
(2) W _α represents an oxygen atom or a —NT _α — group (T _α represents a hydrogen atom or a substituent on a nitrogen atom).
(3) K _α and L _α are the same or different and represent a hydrogen atom or a substituent on a carbon atom, and K _α and L _α are a C3-C10 alkylene group which may have a substituent. Alternatively, it may form a C4-C10 alkenylene group which may have a substituent. ]
A group represented by
Formula (II'-2)

[Wherein, T _α represents the same meaning as described above, and L _β represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (II'-3)

[Wherein, T _α represents the same meaning as described above. ]
A group represented by
Formula (II'-5)

[Wherein, T _α represents the same meaning as described above, and K _β represents a cyano group or a UOCO- group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
A group represented by
Formula (II'-6)

[Wherein W _α represents the same meaning as described above, and K _γ and L _δ represent a C3-C10 alkylene group which may have a substituent or a C4-C10 alkenylene which may have a substituent. Make a basis. ]
A group represented by
Formula (II'-7)

[Wherein Q _α and W _α represent the same meaning as described above, and K _δ and L _ε represent -V _α = V _α '-V _α ″ = V _α ''' -group (V _α , V _α ′, V _α ″ and V _α ″ ″ are the same or different and each represents an optionally substituted methine group or —N = group, and V _α , V _α ′, V _α ″ And at least one of V _α ′ ″ represents —N = group. ]
A group represented by
Formula (II'-8)

[Wherein, T _α represents the same meaning as described above, and Q _β represents a hydroxyl group which may be substituted. ]
Or a group represented by
Formula (II'-9)

[Wherein W _α represents the same meaning as described above. ]
Represents a group represented by
However, when α is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:

Formula (V ')

[Where:
I. a is a thiophene ring, a furan ring, represents a pyrrole ring or a tetrazole ring, X _a is C1-C10 alkyl group substituted with a cyano group, or, C1-C10 alkyl substituted with tetrahydropyran-4-ylidene group Group, a C2-C10 alkenyl group substituted with a halogen atom or a cyano group, a C2-C10 alkenyl group substituted with a C1-C10 alkoxycarbonyl group, or a C3-C10 alkynyl group substituted with a hydroxy group Or a ₀ -r ₁ -br ₁ ′ -group {a ₀ is a methyl group substituted with a C1-C10 alkylthio group, a methyl group substituted with a C1-C10 alkylsulfinyl group, or a C1-C10 alkyl A methyl group substituted with a sulfonyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, an r ₂ O—CO— group (r ₂ is a C2-C10 alkyl group or a C2-C10 alkyl group substituted with a hydroxyl group) Express) Group, RR'N-CO- group (r and r 'are the same or _different. Represents a hydrogen atom or a C1-C10 alkyl group), a 1 -NH-CO- group _{(a 1,} the C1-C10 . representing a C2-C10 alkyl group substituted with an alkoxy group), _{a 1} '-CO- group _{(a 1'} represents a morpholino group), rr'N-CH ₂ -. group (r and r 'are , R _0- (O) ₁ —CONH—CH ₂ — group (r ₀ represents a C 1 -C 10 alkyl group, and l represents 0 or 1), r— An OCH ₂ — group (where r represents the same meaning as described above), an r ₀ —CO— group (where r ₀ represents the same meaning as described above), a cyano group or a sulfomethyl group, and r ₁ represents represents a C1-C10 alkylene group, r 1 _'represents a single bond or a C1-C10 alkylene group, b is oxy, thio, sulfinyl group, sulfonyl group or embryos Roh represents a group. }, _Or, a 2 -y-CO-NH- group _{(a 2} represents a C2-C10 alkyl group substituted with C1-C10 alkoxy group, y represents an oxy group or an imino group.), Or , rO-COCO-NH- group (r represents the same meaning as above.), _{or, a} 3 -z-NH- group _{(a 3} is C2-C10 alkenyl group, or, C1-C10 alkoxy group Represents a C1-C10 alkyl group substituted with a C1-C10 alkoxycarbonyl group, a carboxy group or a cyano group, and z represents a carbonyl group or a sulfonyl group) or an a ₄ -Nr′CO— group {a _4, C1-C10 alkoxy group, or a C3-C10 alkenyloxy group, or, r 0 _-SO 2 _- group (. r ₀ represents the same meaning as), or a hydroxyl or C1-C10 alkoxy A C2-C10 alkyl group substituted with a group, or an r ₀ r ₀ 'N- group (where r ₀ is the same as defined above) Represents one meaning of, _{r 0} 'is different from _{r 0} the same or different, C2-C10 alkyl group substituted with represents the same meaning as _{r 0.),} Or, and rO-CO- group (r is Represents the same meaning as described above), a C1-C10 alkyl group substituted with a cyano group or an aminocarbonyl group, or an rO—CO— (rO—COCH ₂ ) CH— group (r is as defined above). And r ′ represents the same meaning as described above. }, _Or, a 5 -NHSO ₂ - group (. _{A 5} represents a C2-C10 alkyl group substituted with C1-C10 alkoxy group), _or, r 0 ON = CH- group _{(r 0,} the Or r ₀ NHCSNH- group (r ₀ represents the same meaning as described above), or r ₀ NHC (-Sr ₀ ') = N- group (r ₀ and r ₀ ′ represents the same meaning as described above.) or (rO) ₂ P (═O) CH ₂ — group (r represents the same meaning as described above), and p represents 0. , 1, 2 or 3 and when p is 2 or more, X _a is the same or different,
Y _a is a halogen atom, a C1-C10 alkyl group that may be substituted with a halogen atom, a C1-C10 alkyl group that may be substituted with a C1-C10 alkoxy group, or a C2-C10 alkenyl group, Or a C2-C10 alkynyl group, a 2-oxo-oxazolidin-3-yl group, a [1,3] dioxolan-2-yl group, or a C1-C10 alkoxy group substituted with a morpholino group, or , A ₀ '-b'- group (a ₀ ' represents a C1-C10 alkyl group which may be substituted with a halogen atom, and b 'represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group). Or a nitro group, a cyano group, or an rO—CO— group (where r represents the same meaning as described above), or an r ₀ r ₀ ′ N-group (r ₀ and r ₀ ′ are represents the same meaning as.), _or, r 0 CO-NH- group _{(r 0,} the same Meanings.), _Or, _{r 0} r 0 'NCONH- group _{(r 0} and _{r 0',} the. Represents the same meaning as), or, Rr'NCO- group (r and r 'are, Represents the same meaning as described above), or represents a hydroxyl group, q represents 0, 1, 2 or 3, and when q is 2 or more, Y _a is the same or different and q is 2 or more. In some cases, adjacent Y _a may be condensed with a ring to form a 2,3-dihydro-benzo [1,4] dioxin ring.
II. b '
Formula (V'-1)

Wherein, _{Q a} _is r a -O- group _{{r a} is a hydrogen atom, or, C1-C10 alkyl group, or, C3-C10 alkenyl group, or, C3-C10 alkynyl group, or, _{r 0} r ₀ 'N-CH ₂ - group _{(r 0} and _{r 0'} represents the same meaning as.), Roch ₂ - group _(. r is representative of the same meaning as _above), r 0 -CO - group (. r ₀ is representative of the same meaning), C1-C10 alkoxycarbonyl group, a carboxy group, C1-C10 alkyl group substituted with aminocarbonyl group or a cyano group, or, r ₃ -r ₁ -Represents a group (wherein r ₃ represents a phenyl group or a pyridyl group, and r ₁ represents the same meaning as described above). }, Or piperidino group, morpholino group, or r ₄ r ₄ ′ N-group (where r ₄ and r ₄ ′ are the same or different, a hydrogen atom, a C1-C10 alkyl group, or C 3 -C10 alkenyl group, or C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with C1-C10 alkoxy group. However, not hydrogen atoms at the same time.) represents, W _a is , oxygen atom or -NT _a - group _{[T a} is _{r b} - group _{(r b} may be the same or different phases and _{r a,} represents the same meaning as _{r a.)} or _{r 3} '- group _{(r 3} 'differs r ₃ and same or different, represent a representative.) the same meaning as r _3. Represents], K _a represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, a L _a represents a hydrogen atom or a C1-C10 alkyl group, a and K _a and L _a, C3-C10 alkylene group Alternatively, it may form a 1,3-butadienylene group. ]
A group represented by
Formula (V'-2)

Wherein, T _a represents the same meaning as above, L _b represents a hydroxyl group or a methyl group. ]
A group represented by
Formula (V'-3)

Wherein, T _a represents the same meaning as, L _c represents a C1-C10 alkyl group. ]
A group represented by
Formula (V'-4)

Wherein, T _a represents the same meaning as above. ]
A group represented by
Formula (V'-5)

Wherein, T _a represents the same meaning as above, K _b is cyano group or UOCO- group (U represents. A hydrogen atom or a C1-C10 alkyl group);. ]
A group represented by
Formula (V'-6)

[Wherein W _a represents the same meaning as described above, and K _c and L _{d form} a C3-C10 alkylene group or a C4-C10 alkenylene group. ]
A group represented by
Formula (V'-7)

Wherein, _{Q a} and _{W a} represents the same meaning as, the _{K d} and _{_{_{L e, -V a = V a}}} '-V a''= V a''' - group _{(V a} , V _a ′, V _a ″ and V _a ″ are the same or different and represent a methine group or —N = group, and V _a , V _a ′, V _a ″ and V _a ″ At least one of-represents -N = group. ]
A group represented by
Formula (V'-8)

Wherein, _{T a} represents the same meaning as, _{Q b} _is r a -O- group _{(r a} represents. The same meanings as the above) represents a. ]
Or a group represented by
Formula (V-9 ')

[Wherein W _a represents the same meaning as described above. ]
Represents a group represented by
However, when a is a furan ring or a thiophene ring, p and q are not 0 simultaneously.
In addition, “representing the same meaning as described above” in the same symbol among a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other. The range of choices of substituents selected among groups is the same, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
A cinnamoyl compound represented by:

An extracellular matrix gene transcription repressing composition comprising the compound according to any one of claims 2 to 6, 10 and 11, and an inert carrier.

An extracellular matrix gene transcription repressing composition comprising the compound according to claim 5 and 11 and an inert carrier.

Use of a cinnamoyl compound contained as an active ingredient in the composition according to claim 1 or 9, as an active ingredient for suppressing transcription of an extracellular matrix gene.

Use of the compound according to claims 2 to 6, 10 and 11 as an active ingredient for suppressing transcription of an extracellular matrix gene.

Use of a compound according to claims 5 and 11 as an active ingredient for inhibiting transcription of extracellular matrix genes.

10. The composition according to claim 1 or 9 as an active ingredient for improving tissue fibrosis by reducing the amount of extracellular matrix gene expression and reducing the amount of extracellular matrix accumulation. Use of cinnamoyl compounds.

Use of a compound according to claims 2-6, 10 and 11 as an active ingredient to improve tissue fibrosis by reducing the amount of extracellular matrix gene expression and reducing the amount of extracellular matrix accumulation. .

Tissue fibrosis, comprising administering an effective amount of a cinnamoyl compound contained as an active ingredient in the composition of claims 1 and 9 to a mammalian patient in need of treatment to improve tissue fibrosis How to improve.

A method for improving tissue fibrosis, comprising administering an effective amount of the compound according to claims 2 to 6, 10, and 11 to a mammalian patient in need of a treatment for improving tissue fibrosis.

A chronic renal failure comprising a cinnamoyl compound contained as an active ingredient in the composition according to claim 1 or 9, or a compound according to claims 2-6, 10 and 11 and an inert carrier. Therapeutic agent.

Use of a cinnamoyl compound contained as an active ingredient in a composition according to claims 1 and 9, or a compound according to claims 2-6, 10 and 11 as an active ingredient for treating chronic renal failure.

An effective amount of a cinnamoyl compound contained as an active ingredient in the composition according to claim 1 or 9, or a compound according to claims 2-6, 10 and 11 in a mammal in need of therapeutic treatment for chronic renal failure A method for treating chronic renal failure, comprising administering to a patient.

A therapeutic agent for heart failure comprising the cinnamoyl compound contained as an active ingredient in the composition according to claim 1 or 9, or the compound according to claims 2-6, 10 and 11 and an inert carrier. .

Use of a cinnamoyl compound contained as an active ingredient in a composition according to claims 1 and 9, or a compound according to claims 2-6, 10 and 11 as an active ingredient for treating heart failure.

An effective amount of the cinnamoyl compound contained as an active ingredient in the composition according to claim 1 or 9, or the compound according to claims 2-6, 10 and 11 to a mammalian patient in need of heart failure treatment. A method for treating heart failure, comprising administering the method.

A TGF-β action-suppressing composition comprising a cinnamoyl compound contained in the composition according to claim 1 and 9 as an active ingredient and an inert carrier.

A TGF-β action inhibitory composition comprising the compound according to claim 2, 10 and 11 and an inert carrier.

Use of a cinnamoyl compound contained as an active ingredient in the composition according to claim 1 or 9, as an active ingredient for suppressing the action of TGF-β.

Use of a compound according to claims 2-6, 10 and 11 as an active ingredient for inhibiting the action of TGF-β.

A hair nourishing composition comprising a cinnamoyl compound contained as an active ingredient in the composition according to claim 1 or 9, or a compound according to claims 2 to 6, 10 and 11, and an inert carrier. object.

Contained as an active ingredient in the composition according to claims 1 and 9, as an active ingredient for obtaining a hair nourishing effect by inhibiting the promotion of the transition to the hair regression stage by TGF-β and leading to an extension of the hair growth stage 12. Use of a cinnamoyl compound or a compound according to claims 2-6, 10 and 11.

An effective amount of the cinnamoyl compound contained as an active ingredient in the composition according to claim 1 or 9, or the compound according to claims 2-6, 10 and 11 to a mammalian patient in need of hair restoration treatment. A hair-growth method characterized by administering.