JP4797351B2 - Cinnamoyl compounds and uses thereof - Google Patents

Description

  The present invention relates to cinnamoyl compounds and uses thereof.

  Diseases and abnormalities such as cirrhosis, interstitial lung disease, chronic renal failure (or disease that causes chronic renal failure), post-inflammation hyperplasia, postoperative scar or burn scar, scleroderma, arteriosclerosis, hypertension In, the tissue becomes fibrotic and hardened due to excessive accumulation of the extracellular matrix as typified by collagen, resulting in a decrease in organ / tissue function and scar formation. Such excessive accumulation of extracellular matrix is induced by increased production of collagen based on the breakdown of the balance between biosynthesis and degradation of collagen and the like. In fact, in fibrotic tissues, it has been observed that the expression level of collagen genes, particularly type I collagen genes, is increased (see, for example, Non-Patent Document 1 and Non-Patent Document 2). It has also been observed that in fibrotic tissue, the amount of TGF-β, which is a kind of cytokine, is increased (see, for example, Non-Patent Document 1 and Non-Patent Document 2). TGF-β has been shown to increase the expression level of type I collagen gene, and to be involved in increased collagen production and thus tissue fibrosis (for example, Non-Patent Document 3 and Non-Patent Document 4). reference). Furthermore, it is clear that administration of anti-TGF-β antibody and soluble anti-TGF-β receptor to tissue fibrosis model animals improves tissue fibrosis and accompanyingly improves tissue function. (See, for example, Non-Patent Document 5, Non-Patent Document 6 and Non-Patent Document 7), and administration of a compound that suppresses the intracellular signal transduction of TGF-β, thereby fibrosis of tissue. It is also known that the tissue function is improved accordingly (see, for example, Non-Patent Document 8, Non-Patent Document 9, and Non-Patent Document 10).

J. et al. Invest. Dermatol. , 94, 365, (1990) Proc. Natl. Acad. Sci. USA, 88, 6642, (1991) Lab. Invest. , 63, 171, (1990) J. et al. Invest. Dermatol. , 94, 365, (1990) Diabetes, 45, 522-530, (1996) Proc. Natl. Acad. Sci. USA, 96, 12719-12724, (1999) Proc. Natl. Acad. Sci. USA, 97, 8015-8020, (2000) Autoimmunity, 35, 277-282, (2002) J. et al. Hepatol. , 37, 331-339, (2002) Life Sci. , 71, 1559-1606, (2002)

  Therefore, the development and provision of an agent that improves tissue fibrosis (ie, a collagen accumulation inhibitor or a fibrosis therapeutic agent) by reducing the expression level of type I collagen gene in the tissue and decreasing the amount of collagen accumulation. Longed for.

［式中、
Ｉ．Ａは、ベンゼン環又はピリジン環を表し、（Ｙ_α）_ｑにおいて、Ｙ_αは、炭素原子上の置換基であって、下記のＸ_０群又はＹ_０群の基を表し、ｑは、０、１、２、３又は４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Ａ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群に属さない炭素原子上の置換基を表し、ｐは、１、２、３、４又は５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５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、Ａ環と縮環する基である。
ＩＩ．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。
ＩＩＩ．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C1‐C10アルキレン基又は置換基を有してもよいC1-C10アルケニレン基をなすことがある。
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；
２．式（II）

［式中、
Ｉ．Ａは、ベンゼン環又はピリジン環を表す。
ＩＩ．（Ｘ_Ａ０）_ｐにおいて、Ｘ_Ａ０は、炭素原子上の置換基であって、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、１、２、３、４又は５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）_ｎＲ１’）−基（Ｒ１’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_１Ｒ１’ＮＣ（＝Ｎ−（Ｏ）_ｎ−Ａ_１）−基（Ｒ_１、Ｒ１’、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）_ｍＲ１’）−基（Ｒ１’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_１Ｒ１’Ｎ−基（Ｒ_１及びＲ１’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−ＮＲ１’−基（Ｒ_１、Ａ_１及びＲ１’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（Ｒ１’（Ｏ）_ｎ）Ｎ−ＣＲ１’’＝Ｎ−Ｒ_６−基（Ｒ_１、Ｒ１’、ｎ及びＲ_６は、前記と同一の意味を表し、Ｒ１’’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＝ＣＲ１’−ＮＲ_２−Ｒ_６−基（Ｒ_１、ｎ、Ｒ１’、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−ＮＲ１’−Ｒ_６−基（Ｒ_２、Ｂ_３、Ｒ_１、Ｒ１’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。］、
Ａ７’−Ｂ_２’−Ｂ_３−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ７’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−Ｒ４’−基（Ｒ_２及びＢ_１は、前記と同一の意味を表し、Ｒ４’は、C2-C10アルキレン基を表す。）、Ｄ_４−Ｒ４’−基（Ｄ_４及びＲ４’は、前記と同一の意味を表す。）、Ｄ_１−Ｒ４’−基（Ｄ_１及びＲ４’は、前記と同一の意味を表す。）、（ｂ_０）−Ｒ４’−基（（ｂ_０）及びＲ４’は、前記と同一の意味を表す。）、（ｃ_０）−Ｒ４’−基（（ｃ_０）及びＲ４’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−Ｒ４’−基（Ｄ_３及びＲ４’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’Ｒ１’）−基（ｎ’は、ｎと同一又は相異なり、ｎと同一の意味を表し、Ｒ１’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。］、Ａ８’−Ｂ_２’−ＣＳ−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ８’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。］、Ａ８’−Ｓ−Ｂ_３’−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ８’、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Ａ７’’−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ７’’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−Ｒ４’−基（Ｒ_２、Ｂ_１及びＲ４’は、前記と同一の意味を表す。）、Ｄ_４−Ｒ４’−基（Ｄ_４及びＲ４’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−Ｒ４’−基（Ｄ_１及びＲ４’は、前記と同一の意味を表す。）、（ｂ_０）−Ｒ４’−基（（ｂ_０）及びＲ４’は、前記と同一の意味を表す。）、（ｃ_０）−Ｒ４’−基（（ｃ_０）及びＲ４’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、Ａ９’（Ｏ）_ｍＮ＝Ｃ（Ａ_９）−基（Ａ９’は、Ａ７’又はＡ８’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−Ｂ１’−Ｒ_６−基（Ａ_９及びＲ_６は、前記と同一の意味を表し、Ｂ１’は、オキシ基又はチオ基を表す。但し、Ｂ１’がオキシ基のとき、Ａ_９は、Ａ_８ではない。）、又は、Ａ_９−ＣＳ−Ｂ１’−Ｒ_６−基（Ａ_９、Ｂ１’及びＲ_６は、は、前記と同一の意味を表す。）、又は、Ａ７’’−ＳＯ_２−Ｂ１’−Ｒ_６−基（Ａ７’’、Ｂ１’及びＲ_６は、は、前記と同一の意味を表す。）、又は、Ａ_８−ＳＯ_２−Ｂ１’−Ｒ_６−基（Ａ_８、Ｂ１’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、Ａ９’−Ｂ_２’−Ｂ_３−Ｂ１’−Ｒ_６−基（Ａ９’、Ｂ_２’、Ｂ_３、Ｂ１’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。）、Ａ９’Ｏ−基（Ａ９’は、前記と同一の意味を表す。但し、ｎは１ではない。）、Ａ９’−基（Ａ９’は、前記と同一の意味を表す。但し、ｎが０のとき、Ａ８’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：Ａ１０’−Ｎ（（Ｏ）_ｎＲ_１）−ＳＯ_２−Ｒ_６−基［Ａ１０’は、水素原子（但し、ｎは０ではない。）、Ａ９’Ｏ−基（Ａ９’は、前記と同一の意味を表す。但し、ｎは１ではない。）、Ａ９’−基（Ａ９’は、前記と同一の意味を表す。但し、ｎが０のとき、Ａ８’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。］、Ａ９’’Ｒ_１Ｎ−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ１’）−Ｒ_６−基［Ａ９’’は、水素原子又はＡ９’−基（Ａ９’は、前記と同一の意味を表す。）を表し、Ｒ_１、ｎ、Ｒ１’及びＲ_６は、前記と同一の意味を表す。］又は（ｂ_０）−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ１’）−Ｒ_６−基［（ｂ_０）、ｎ、Ｒ１’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_１Ｒ１’Ｎ−（Ｒ_２Ｓ）Ｃ＝Ｎ−Ｒ_６−基（Ｒ_１、Ｒ１’、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（Ｒ１’Ｏ）Ｎ−Ｒ_６−基（Ｒ_１、Ｒ１’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）（ＯＲ１’）−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、Ｒ１’及びＲ_４は、前記と同一の意味を表す。］
ＩＩＩ．（Ｙ_Ａ０）_ｑにおいて、Ｙ_Ａ０は、炭素原子上の置換基であって、下記のＸ_０群又はＹ_０群の基を表し、ｑは、０、１、２、３又は４を表し、ｐ（ｐは、前記と同一の意味を表す。）とｑとの和は５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、Ａ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、Ａ環と縮環する基
IＶ．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。］、Ａ７’’−ＳＯ_２−Ｂ_ｃ−基（Ａ７’’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_１Ｒ１’Ｎ−ＳＯ_２−Ｂ_ｃ−基（Ｒ_１、Ｒ１’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。）、Ａ９’−Ｂ_ｃ−基（Ａ９’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。
Ｖ．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、C1-C10アルキレン基、又は、単数又は同一又は相異なる複数のＭ_ａ基で置換されてもよいC1-C10アルケニレン基をなすことがある。
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．Ａは、ベンゼン環又はピリジン環を表す。
ＩＩ．（Ｘ_Ａ）_ｐにおいて、Ｘ_Ａは、炭素原子上の置換基であって、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、１、２、３、４又は５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）_ｎＲ１’）−基（Ｒ１’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_１Ｒ１’ＮＣ（＝Ｎ−（Ｏ）_ｎ−Ａ_１）−基（Ｒ_１、Ｒ１’、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−ＮＲ１’−基（Ｒ１’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−ＮＲ１’−基（Ｒ１’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）_ｍＲ１’）−基（Ｒ１’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_１Ｒ１’Ｎ−基（Ｒ_１及びＲ１’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−ＮＲ１’−基（Ｒ_１、Ａ_１及びＲ１’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（Ｒ１’（Ｏ）_ｎ）Ｎ−ＣＲ１’’＝Ｎ−Ｒ_６−基（Ｒ_１、Ｒ１’、ｎ及びＲ_６は、前記と同一の意味を表し、Ｒ１’’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＝ＣＲ１’−ＮＲ_２−Ｒ_６−基（Ｒ_１、ｎ、Ｒ１’、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−ＮＲ１’−Ｒ_６−基（Ｒ_２、Ｂ_３、Ｒ_１、Ｒ１’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。］、Ａ７’−Ｂ_２’−Ｂ_３−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ７’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−Ｒ４’−基（Ｒ_２及びＢ_１は、前記と同一の意味を表し、Ｒ４’は、C2-C10アルキレン基を表す。）、Ｄ_４−Ｒ４’−基（Ｄ_４及びＲ４’は、前記と同一の意味を表す。）、Ｄ_１−Ｒ４’−基（Ｄ_１及びＲ４’は、前記と同一の意味を表す。）、（ｂ）−Ｒ４’−基（（ｂ）及びＲ４’は、前記と同一の意味を表す。）、（ｃ）−Ｒ４’−基（（ｃ）及びＲ４’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−Ｒ４’−基（Ｄ_３及びＲ４’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’Ｒ１’）−基（ｎ’は、ｎと同一又は相異なり、ｎと同一の意味を表し、Ｒ１’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。］、Ａ８’−Ｂ_２’−ＣＳ−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ８’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。］、Ａ８’−Ｓ−Ｂ_３’−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ８’、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Ａ７’’−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ_１）−Ｒ_６−基［Ａ７’’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−Ｒ４’−基（Ｒ_２、Ｂ_１及びＲ４’は、前記と同一の意味を表す。）、Ｄ_４−Ｒ４’−基（Ｄ_４及びＲ４’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−Ｒ４’−基（Ｄ_１及びＲ４’は、前記と同一の意味を表す。）、（ｂ）−Ｒ４’−基（（ｂ）及びＲ４’は、前記と同一の意味を表す。）、（ｃ）−Ｒ４’−基（（ｃ）及びＲ４’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、Ａ９’（Ｏ）_ｍＮ＝Ｃ（Ａ_９）−基（Ａ９’は、Ａ７’又はＡ８’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−Ｂ１’−Ｒ_６−基（Ａ_９及びＲ_６は、前記と同一の意味を表し、Ｂ１’は、オキシ基又はチオ基を表す。但し、Ｂ１’がオキシ基のとき、Ａ_９は、Ａ_８ではない。）、又は、Ａ_９−ＣＳ−Ｂ１’−Ｒ_６−基（Ａ_９、Ｂ１’及びＲ_６は、は、前記と同一の意味を表す。）、又は、Ａ７’’−ＳＯ_２−Ｂ１’−Ｒ_６−基（Ａ７’’、Ｂ１’及びＲ_６は、は、前記と同一の意味を表す。）、又は、Ａ_８−ＳＯ_２−Ｂ１’−Ｒ_６−基（Ａ_８、Ｂ１’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、Ａ９’−Ｂ_２’−Ｂ_３−Ｂ１’−Ｒ_６−基（Ａ９’、Ｂ_２’、Ｂ_３、Ｂ１’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。）、Ａ９’Ｏ−基（Ａ９’は、前記と同一の意味を表す。但し、ｎは１ではない。）、Ａ９’−基（Ａ９’は、前記と同一の意味を表す。但し、ｎが０のとき、Ａ８’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：Ａ１０’−Ｎ（（Ｏ）_ｎＲ_１）−ＳＯ_２−Ｒ_６−基［Ａ１０’は、水素原子（但し、ｎは０ではない。）、Ａ９’Ｏ−基（Ａ９’は、前記と同一の意味を表す。但し、ｎは１ではない。）、Ａ９’−基（Ａ９’は、前記と同一の意味を表す。但し、ｎが０のとき、Ａ８’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。］、Ａ９’’Ｒ_１Ｎ−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ１’）−Ｒ_６−基［Ａ９’’は、水素原子又はＡ９’−基（Ａ９’は、前記と同一の意味を表す。）を表し、Ｒ_１、ｎ、Ｒ１’及びＲ_６は、前記と同一の意味を表す。］又は（ｂ）−ＳＯ_２−Ｎ（（Ｏ）_ｎＲ１’）−Ｒ_６−基［（ｂ）、ｎ、Ｒ１’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_１Ｒ１’Ｎ−（Ｒ_２Ｓ）Ｃ＝Ｎ−Ｒ_６−基（Ｒ_１、Ｒ１’、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（Ｒ１’Ｏ）Ｎ−Ｒ_６−基（Ｒ_１、Ｒ１’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）（ＯＲ１’）−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、Ｒ１’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、炭素原子上の置換基であって、下記のＸ群及びＹ群の基を表し、ｑは、０、１、２、３又は４を表し、ｐ（ｐは、前記と同一の意味を表す。）とｑとの和は５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：−Ｎ＝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す。）、−Ｙ_ｂ−Ｙ_ｂ’−Ｙ_ｂ’’−基（Ｙ_ｂ及びＹ_ｂ’’は、同一又は相異なり、メチレン基、又は、オキシ基、又は、チオ基、又は、スルフィニル基、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_ｂ’は、ハロゲン原子で置換されてもよいC1-C4アルキレン基、又は、オキソ基を有してもよいC1-C4アルキレン基を表す。）又は−Ｙ_ｃ−Ｏ−Ｙ_ｃ’−Ｏ−基（Ｙ_ｃ及びＹ_ｃ’は、同一又は相異なり、C1-C10アルキレン基を表す。）である。
IＶ．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。］、Ａ７’’−ＳＯ_２−Ｂ_ｃ−基（Ａ７’’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_１Ｒ１’Ｎ−ＳＯ_２−Ｂ_ｃ−基（Ｒ_１、Ｒ１’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。）、Ａ９’−Ｂ_ｃ−基（Ａ９’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。
Ｖ．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、C1‐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。
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、Ａは、ベンゼン環又はピリジン環を表し、Ｘ_ａは、炭素原子上の置換基で、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、ｒ_０Ｏ−ＣＯＣＯ−ＮＨ−基（ｒ_０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−ＮＨＣＯ−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、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。）、又は、（ｒ_０Ｏ）_２Ｐ（＝Ｏ）ＣＨ_２−基（ｒ_０は、前記と同一の意味を表す。）を表し、ｐは、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、ニトロ基、ｒ_０ＣＯ−ＮＨ−基（ｒ_０は、前記と同一の意味を表す。）、C1-C10アルキル基又はC1-C10アルコキシ基を表し、ｑは、０、１又は２を表し、ｑが２以上のとき、Ｙ_ａは、同一又は相異なる。
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、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、C1-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。
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、ａは、ベンゼン環又はピリジン環を表し、ｘは、メチン基又は窒素原子を表し、Ｘ_ａは、炭素原子上の置換基で、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、ｒ_０Ｏ−ＣＯＣＯ−ＮＨ−基（ｒ_０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−ＮＨＣＯ−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、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。）、又は、（ｒ_０Ｏ）_２Ｐ（＝Ｏ）ＣＨ_２−基（ｒ_０は、前記と同一の意味を表す。）を表し、ｐは、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、ニトロ基、ｒ_０ＣＯ−ＮＨ−基（ｒ_０は、前記と同一の意味を表す。）、C1-C10アルキル基又はC1-C10アルコキシ基を表し、ｑは、０、１又は２を表し、ｑが２以上のとき、Ｙ_ａは、同一又は相異なる。
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、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、C1-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。
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、ａは、ベンゼン環又はピリジン環を表し、ｘは、メチン基又は窒素原子を表し、Ｘ_ａは、炭素原子上の置換基で、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、ｒ_０Ｏ−ＣＯＣＯ−ＮＨ−基（ｒ_０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−ＮＨＣＯ−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、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。）、又は、（ｒ_０Ｏ）_２Ｐ（＝Ｏ）ＣＨ_２−基（ｒ_０は、前記と同一の意味を表す。）を表し、ｐは、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、ニトロ基、ｒ_０ＣＯ−ＮＨ−基（ｒ_０は、前記と同一の意味を表す。）、C1-C10アルキル基又はC1-C10アルコキシ基を表し、ｑは、０、１又は２を表し、ｑが２以上のとき、Ｙ_ａは、同一又は相異なる。
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2H-ピラン-2-オン化合物；
７．式（VII）

[式中、Ｘ_ａ’は、シアノ基で置換された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、ａ_０’−ｒ_１−Ｏ−基｛ａ_０’は、C1-C10アルキルチオ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、ＨＯＣＨ_２−基又はシアノ基を表し、ｒ_１は、C1-C10アルキレン基を表す。｝、又は、ａ_６−ＣＯＮＨ−基（ａ_６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。）、又は、ａ_７−ＮＨＣＯ−基（ａ_７は、C1-C10アルコキシ基で置換されたC2-C10アルキル基又はC1-C10アルコキシカルボニル基で置換されたC1-C10アルキル基を表す。）を表す。を表す。
ｑ_ａ’は、C3-C10アルキニル基で置換されたアミノ基、ピペリジノ基、モルホリノ基又はｒ_ａ’−Ｏ−基（ｒ_ａ’は、水素原子、C1-C10アルキル基又はC3-C10アルケニル基を表す。）を表す。]
で示される2H-ピラン-2-オン化合物；
８．式（VIII）

[式中、ａは、ベンゼン環又はピリジン環を表し、ｘは、メチン基又は窒素原子を表し、Ｘ_ａは、炭素原子上の置換基で、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、ｒ_０Ｏ−ＣＯＣＯ−ＮＨ−基（ｒ_０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−ＮＨＣＯ−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、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。）、又は、（ｒ_０Ｏ）_２Ｐ（＝Ｏ）ＣＨ_２−基（ｒ_０は、前記と同一の意味を表す。）を表し、ｐは、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、ニトロ基、ｒ_０ＣＯ−ＮＨ−基（ｒ_０は、前記と同一の意味を表す。）、C1-C10アルキル基又はC1-C10アルコキシ基を表し、ｑは、０、１又は２を表し、ｑが２以上のとき、Ｙ_ａは、同一又は相異なる。
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2H-1-ベンゾピラン-2-オン化合物；
９．式（IX）

[式中、Ｘ_a’’は、シアノ基若しくはヒドロキシメチル基で置換されたC1-C10アルコキシ基、又は、ａ_６−ＣＯＮＨ−基（ａ_６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。）、又は、ａ_７−ＮＨＣＯ−基（ａ_７は、水酸基で置換されたC2-C10アルキル基、又は、C1-C10アルコキシ基で置換されたC2-C10アルキル基、又は、C1-C10アルコキシカルボニル基で置換されたC1-C10アルキル基を表す。）を表し、ｑ_ａ’’は、水酸基、C1-C10アルコキシ基又はピペリジノ基を表す。]
で示される2H-1-ベンゾピラン-2-オン化合物；
１０．式（X）

[式中、Ｘ_Ｉは、シアノ基で置換されたC2-C4アルケニル基、Ａ_Ｉ−Ｒ_Ｉ−Ｏ−基（Ａ_Ｉは、C1-C4アルキルチオ基、C2-C4アルケニル基、C2-C4アルキニル基、C1-C4アルコキシカルボニル基、カルボキシ基又はシアノ基を表し、Ｒ_Ｉは、C1-C4アルキレン基を表す。）、Ａ_ＩＩ−（ｙ）_ｍ−ｚ−ＮＨ−基（Ａ_ＩＩは、C2-C4アルケニル基、又は、C1-C4アルコキシ基、C1-C4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-C4アルキル基を表し、ｙは、オキシ基又はイミノ基を表し、ｚは、カルボニル基又はスルホニル基を表し、ｍは、０又は１を表す。）又はＡ_ＩＩＩ−ＮＨＣＯ−基（Ａ_ＩＩＩは、メタンスルホニル基、又は、水酸基、C1-C4アルコキシ基、C1-C4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-C4アルキル基を表す。）を表し、ａ_Ｉは、水酸基、C1-C4アルコキシ基、C2-C4アルケニルオキシ基、C2-C4アルキニルオキシ基、C1-C4アルキルアミノ基、C2-C4アルケニルアミノ基、C2-C4アルキニルアミノ基、モルホリノ基又はピペリジノ基を表し、Ｙ_Ｉは、ハロゲン原子、ニトロ基、C1-C4アルキル基又はC1-C4アルコキシ基を表し、ｎは、０、１又は２を表し、ｎが２の場合にはＹ_Ｉは相異なってよい。]
で示される2H-ピラン-2-オン化合物；
１１．式（XI）

[式中、Ｘ_Ｉは、シアノ基で置換されたC2-C4アルケニル基、Ａ_Ｉ−Ｒ_Ｉ−Ｏ−基（Ａ_Ｉは、C1-C4アルキルチオ基、C2-C4アルケニル基、C2-C4アルキニル基、C1-C4アルコキシカルボニル基、カルボキシ基又はシアノ基を表し、Ｒ_Ｉは、C1-C4アルキレン基を表す。）、Ａ_ＩＩ−（ｙ）_ｍ−ｚ−ＮＨ−基（Ａ_ＩＩは、C2-C4アルケニル基、又は、C1-C4アルコキシ基、C1-C4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-C4アルキル基を表し、ｙは、オキシ基又はイミノ基を表し、ｚは、カルボニル基又はスルホニル基を表し、ｍは、０又は１を表す。）又はＡ_ＩＩＩ−ＮＨＣＯ−基（Ａ_ＩＩＩは、メタンスルホニル基、又は、水酸基、C1-C4アルコキシ基、C1-C4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-C4アルキル基を表す。）を表し、ａ_Ｉは、水酸基、C1-C4アルコキシ基、C2-C4アルケニルオキシ基、C2-C4アルキニルオキシ基、C1-C4アルキルアミノ基、C2-C4アルケニルアミノ基、C2-C4アルキニルアミノ基、モルホリノ基又はピペリジノ基を表し、Ｙ_Ｉは、ハロゲン原子、ニトロ基、C1-C4アルキル基又はC1-C4アルコキシ基を表し、ｎは、０、１又は２を表し、ｎが２の場合にはＹ_Ｉは相異なってよい。]
で示される2H-1-ベンゾピラン-2-オン化合物；
１２．式（XII）

[式中、Ｘ_ＩＩは、アリルオキシ基、プロパルギルオキシ基、シアノメトキシ基、メトキシアセチルアミノ基、メトキシカルボニルメチルアミノカルボニル基又は２−シアノエテニル基を表し、ａ_ＩＩは、水酸基、メトキシ基又はモルホリノ基を表す。]
で示される2H-ピラン-2-オン化合物；
１３．式（XIII）

[式中、Ｘ_ＩＩ’は、シアノメトキシ基、メトキシアセチルアミノ基又は２−ヒドロキシエチルアミノカルボニル基を表す。]
で示される2H-1-ベンゾピラン-2-オン化合物；
１４．式（XIV）

で示される2H-ピラン-2-オン化合物；
１５．式（XV）

で示される2H-ピラン-2-オン化合物；
１６．式（XVI）

で示される2H-ピラン-2-オン化合物；
１７．式（XVII）

で示される2H-ピラン-2-オン化合物；
１８．式（XVIII）

で示される2H-ピラン-2-オン化合物；
１９．式（XIX）

で示される2H-ピラン-2-オン化合物；
２０．式（XX）

で示される2H-ピラン-2-オン化合物；
２１．式（XXI）

で示される2H-ピラン-2-オン化合物；
２２．式（XXII）

で示される2H-ピラン-2-オン化合物；
２３．式（XXIII）

で示される2H-1-ベンゾピラン-2-オン化合物；
２４．式（XXIV）

で示される2H-1-ベンゾピラン-2-オン化合物；
２５．式（XXV）

で示される2H-1-ベンゾピラン-2-オン化合物；
２６．式（XXVI-1）

［式中、Ｘ_ｂは、ＭｅＯ−ＣＯＣＨ_２ＮＨＣＯ−基、ＭｅＯＣＨ_２ＣＨ_２Ｏ−ＣＯ−ＮＨ−基、ＭｅＯＣＨ_２ＣＨ_２ＮＨ−ＣＯ−ＮＨ−基、ＭｅＳＯ_２ＮＨ−ＣＯ−基、ＮＣＣＨ_２ＮＨ−ＣＯ−基、Ｆ_２Ｃ＝ＣＨ−基、ＭｅＯ−ＣＯ−（ＭｅＯ−ＣＯＣＨ_２−）ＣＨ−基、ＭｅＯＣＨ_２ＣＨ_２ＮＨ−ＳＯ_２−基、ＭｅＯ−ＮＨＣＯ−基又はＣＨ_２＝ＣＨＣＨ_２Ｏ−ＮＨＣＯ−基を表す。］、
式（XXVI -2）

[式中、Ｘ_ｂ’は、ＭｅＯＣＨ_２ＣＯ−ＮＨ−基又はＭｅＯＣＨ_２ＣＨ_２ＮＨ−ＣＯ−基を表す。]、
式（XXVI-3）

[式中、Ｘ_ｂ’’は、ＭｅＳＣＨ_２ＣＨ_２Ｏ−基、ＨＯＣＨ_２ＣＨ_２ＯＣＨ_２−基又はＮＣ−ＣＨ_２ＣＨ_２−基を表す。]若しくは
式（XXVI-4）

[式中、Ｘ_ｂ’’’は、ＮＣＣＨ＝ＣＨ−基、Ｈ_２ＮＣＯＣＨ_２Ｏ−基、ＭｅＣＯＣＨ_２Ｏ−基、ＣＨ_３Ｏ−ＣＯＣＨ_２ＳＣＨ_２−基、テトラヒドロピラン−４−イリデンメチル基、ＣＨ_３Ｏ−ＣＯＣＯ−ＮＨ−基又は（ＣＨ_３Ｏ）_２Ｐ（＝Ｏ）ＣＨ_２−基を表す。]
で示されるベンズアルデヒド誘導体又は6-ホルミル-2-[(2-メトキシエチル)アミノカルボニル]ピリジン；
２７．式（XXVII）

で示されるベンズアルデヒド誘導体；
２８．式（XXVIII）

で示されるベンズアルデヒド誘導体；
２９．式（XXIX）

で示されるベンズアルデヒド誘導体；
３０．式（XXX）

で示されるベンズアルデヒド誘導体；
３１．式（XXXI）

で示されるベンズアルデヒド誘導体；
３２．式（XXXII）

で示されるベンズアルデヒド誘導体；
３３．式（XXXIII）

で示されるベンズアルデヒド誘導体；
３４．式（XXXIV）

で示されるベンズアルデヒド誘導体；
３５．式（XXXV）

で示されるベンズアルデヒド誘導体；
３６．式（XXXVI）

で示されるベンズアルデヒド誘導体；
３７．式（XXXVII）

で示されるベンズアルデヒド誘導体；
３８．式（XXXVIII）

で示されるベンズアルデヒド誘導体；
３９．式（XXXIX）

で示されるベンズアルデヒド誘導体；
４０．式（XL）

で示されるベンズアルデヒド誘導体；
４１．式（XLI）

で示されるベンズアルデヒド誘導体；
４２．式（XLII）

で示されるピリジンカルバルデヒド誘導体；
４３．式（XLIII）

で示されるベンズアルデヒド誘導体；
４４．式（XLIV）

で示されるベンズアルデヒド誘導体；
４５．式（XLV）

で示されるベンズアルデヒド誘導体；
４６．前項２６記載の、式（XXVI-1）、式（XXVI-2）、式（XXVI-3）若しくは式（XXVI-4）で示されるベンズアルデヒド誘導体、又は、6-ホルミル-2-[(2-メトキシエチル)アミノカルボニル]ピリジンと、式(XLVI)

［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、同一又は相異なり、C1-C10アルキル基を表す。）、ｒＯＣＨ_２−基（ｒは、水素原子又はC1-C10アルキル基を表す。）、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、C1-C10アルキレン基を表す。）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、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、C1-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。
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。］
で示される化合物とを反応させることを特徴とする、式（XLVI-1）

［式中、Ｘ_ｂは、ＭｅＯ−ＣＯＣＨ_２ＮＨＣＯ−基、ＭｅＯＣＨ_２ＣＨ_２Ｏ−ＣＯ−ＮＨ−基、ＭｅＯＣＨ_２ＣＨ_２ＮＨ−ＣＯ−ＮＨ−基、ＭｅＳＯ_２ＮＨ−ＣＯ−基、ＮＣＣＨ_２ＮＨ−ＣＯ−基、Ｆ_２Ｃ＝ＣＨ−基、ＭｅＯ−ＣＯ−（ＭｅＯ−ＣＯＣＨ_２−）ＣＨ−基、ＭｅＯＣＨ_２ＣＨ_２ＮＨ−ＳＯ_２−基、ＭｅＯ−ＮＨＣＯ−基又はＣＨ_２＝ＣＨＣＨ_２Ｏ−ＮＨＣＯ−基を表し、ｑ_ａ、Ｋ_ａ及びＬ_ａは、前記と同一の意味を表す。］、式（XLVI-2）

［式中、Ｘ_ｂ’は、ＭｅＯＣＨ_２ＣＯ−ＮＨ−基又はＭｅＯＣＨ_２ＣＨ_２ＮＨ−ＣＯ−基を表し、ｑ_ａ、Ｋ_ａ及びＬ_ａは、前記と同一の意味を表す。］、式（XLVI-3）

［式中、Ｘ_ｂ’’は、ＭｅＳＣＨ_２ＣＨ_２Ｏ−基、ＨＯＣＨ_２ＣＨ_２ＯＣＨ_２−基又はＮＣ−ＣＨ_２ＣＨ_２−基を表し、ｑ_ａ、Ｋ_ａ及びＬ_ａは、前記と同一の意味を表す。］、式（XLVI-4）

[式中、Ｘ_ｂ’’’は、ＮＣＣＨ＝ＣＨ−基、Ｈ_２ＮＣＯＣＨ_２Ｏ−基、ＭｅＣＯＣＨ_２Ｏ−基、ＣＨ_３Ｏ−ＣＯＣＨ_２ＳＣＨ_２−基、テトラヒドロピラン−４−イリデンメチル基、ＣＨ_３Ｏ−ＣＯＣＯ−ＮＨ−基又は（ＣＨ_３Ｏ）_２Ｐ（＝Ｏ）ＣＨ_２−基を表し、ｑ_ａ、Ｋ_ａ及びＬ_ａは、前記と同一の意味を表す。]又は式（XLVI-5）

[式中、ｑ_ａ、Ｋ_ａ及びＬ_ａ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；
４７．式（XLVII）

[式中、Ａは、ベンゼン環又はピリジン環を表し、Ｘ_ｃは、炭素原子上の置換基で、
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、ヒドロキシメチル基で置換されたC2-C10アルキニル基、又は、ａ_０ｃ−ｒ_１−ｂ−ｒ_１’−基｛ａ_０ｃ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。）、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。）又はシアノ基を表し、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、ｒ_０Ｏ−ＣＯＣＯ−ＮＨ−基（ｒ_０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−ＮＨＣＯ−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_０Ｏ−ＣＯ−基（ｒ_０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、ｒ_０Ｏ−ＣＯ−（ｒ_０Ｏ−ＣＯＣＨ_２）ＣＨ−基（ｒ_０は、前記と同一の意味を表す。）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。）、又は、（ｒ_０Ｏ）_２Ｐ（＝Ｏ）ＣＨ_２−基（ｒ_０は、前記と同一の意味を表す。）を表し、ｐは、１、２又は３を表し、ｐが２以上のとき、Ｘ_ｃは、同一又は相異なり、
Ｙ_ａは、ハロゲン原子、ニトロ基、ｒ_０ＣＯ−ＮＨ−基（ｒ_０は、前記と同一の意味を表す。）、C1-C10アルキル基又はC1-C10アルコキシ基を表し、ｑは、０、１又は２を表し、ｑが２以上のとき、Ｙ_ａは、同一又は相異なってもよい。
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、C1-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。
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、式（XLVII’）
ｒ_ｃ−Ｖ （XLVII’）
[ｒ_ｃは、ｔ_ｃ’−基｛ｔ_ｃ’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、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。｝を表し、Ｖは、脱離基を表す。
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。]
で示される化合物とを反応させることを特徴とする、式（XLVII’’）

[式中、Ａ、Ｘ_ｃ、Ｙ_ａ、ｐ、ｑ、ｒ_ｃ、Ｋ_ａ及びＬ_ａは、前記と同一の意味を表す。
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の製造法；
４８．式（XLVIII）

[式中、Ａは、ベンゼン環又はピリジン環を表し、Ｘ_ｄは、炭素原子上の置換基で、ａ_０ｄ−ｒ_１−ｂ−ｒ_１’−基｛ａ_０ｄは、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。）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、ｒ_０Ｏ−ＣＯＣＯ−ＮＨ−基（ｒ_０は、C1-C10アルキル基を表す。）、又は、ａ_３ｄ−z−ＮＨ−基（ａ_３ｄは、C1-C10アルコキシカルボニル基で置換された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_４ｄ−ＮＨＣＯ−基｛ａ_４ｄは、ｒ_０Ｏ−ＣＯ−基（ｒ_０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、又は、ｒ_０Ｏ−ＣＯ−（ｒ_０Ｏ−ＣＯＣＨ_２）ＣＨ−基（ｒ_０は、前記と同一の意味を表す。）を表す。｝を表し、ｐは、１、２又は３を表し、ｐが２以上のとき、Ｘ_ｄは、同一又は相異なり、
Ｙ_ａは、ハロゲン原子、ニトロ基、ｒ_０ＣＯ−ＮＨ−基（ｒ_０は、前記と同一の意味を表す。）、C1-C10アルキル基又はC1-C10アルコキシ基を表し、ｑは、０、１又は２を表し、ｑが２以上のとき、Ｙ_ａは、同一又は相異なってもよい。
ｑ_ｄは、ｒ_ｄ−Ｏ−基｛ｒ_ｄ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。）、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、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、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、C1-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。
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を加水分解することを特徴とする、式（XLVIII’）

［式中、Ａは、前記と同一の意味を表し、Ｘ_ｄ’は、炭素原子上の置換基で、炭素原子上の置換基で、ａ_０ｄ’−ｒ_１−ｂ−ｒ_１’−基（ａ_０ｄ’は、カルボキシ基を表し、ｒ_１、ｒ_１’及びｂは、前記と同一の意味を表す。）、又は、ＨＯ−ＣＯＣＯ−ＮＨ−基、又は、ａ_３ｄ’−z−ＮＨ−基（ａ_３ｄ’は、カルボキシ基で置換されたC1-C10アルキル基を表し、ｚは、前記と同一の意味を表す。）、又は、ａ_４ｄ’−ＮＨＣＯ−基（ａ_４ｄ’は、カルボキシ基で置換されたC1-C10アルキル基、又は、ＨＯ−ＣＯ−（ＨＯ−ＣＯＣＨ_２）ＣＨ−基を表す。）を表し、
ｐは、前記と同一の意味を表し、ｐが２以上のとき、Ｘ_ｄ’は、同一又は相異なる。
Ｙ_ａ及びｑは、前記と同一の意味を表す。
ｑ_ｄ’は、ｒ_ｄ’’−Ｏ−基｛ｒ_ｄ’’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。）、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、前記と同一の意味を表す。但し、同時に水素原子となることはない。）を表し、Ｋ_ａ及びＬ_ａは、前記と同一の意味を表す。
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の製造法；
４９．式（XLIX）

[式中、Ａは、ベンゼン環又はピリジン環を表し、Ｘ_ｅは、炭素原子上の置換基で、Ｈ−ｂ’’−基（ｂ’’は、オキシ基又はチオ基を表す。）を表し、ｐは、１、２又は３を表し、ｐが２以上のとき、Ｘ_ｅは、同一又は相異なる。
Ｙ_ａは、ハロゲン原子、ニトロ基、ｒ_０ＣＯ−ＮＨ−基（ｒ_０は、C1-C10アルキル基を表す。）、C1-C10アルキル基又はC1-C10アルコキシ基を表し、ｑは、０、１又は２を表し、ｑが２以上のとき、Ｙ_ａは、同一又は相異なってもよい。
ｑ_ｅは、ｒ_ｅ−Ｏ−基｛ｒ_ｅ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。）、ｒＯＣＨ_２−基（ｒは、水素原子又はC1-C10アルキル基を表す。）、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、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、C1-C10アルキレン基を表す。）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、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、C1-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。
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、式（XLIX’）
ａ_０ｅ−ｒ_１’’−Ｖ’ （XLIX’）
[式中、ａ_０ｅ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。）、ｒｒ’Ｎ−ＣＯ−基（ｒは、前記と同一の意味を表し、ｒ’は、ｒと同一又は相異なり、ｒと同一の意味を表す。）、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、前記と同一の意味を表し、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。）又はシアノ基を表し、ｒ_１’’は、ｒ_１と同一又は相異なり、ｒ_１と同一の意味を表し、Ｖ’は脱離基又は水酸基を表す。
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。]
で示される化合物、1,3-プロパンスルトン又は1,4-ブタンスルトンとを反応させることを特徴とする、式（XLIX’’）

[式中、Ｘ_ｅ’は、ａ_０ｅ’−ｒ_１’’−ｂ’’−基｛ａ_０ｅ’は、ａ_０ｅ−基（ａ_０ｅは、前記と同一の意味を表す。）、３−スルホプロピル基又は４−スルホブチル基を表し、ｒ_１’’及びｂ’’は、前記と同一の意味を表す。｝を表し、Ａ、Ｙ_ａ、ｐ、ｑ、ｑ_ｅ、Ｋ_ａ及びＬ_ａは、前記と同一の意味を表す。
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の製造法；
５０．Ｉ型コラーゲン遺伝子の転写を抑制するための有効成分としての、前項１〜２５記載の化合物の使用；
５１．前項１〜２５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Ｉ型コラーゲン遺伝子転写抑制組成物；
５２．Ｉ型コラーゲン遺伝子の発現量を減少させてコラーゲン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１〜２５記載の化合物の使用；
５３．前項１〜２５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組織線維化改善組成物；
５４．有効量の前項１〜２５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；
５５．ＴＧＦ−βの作用を抑制するための有効成分としての、前項１〜２５記載の化合物の使用；
５６．前項１〜２５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；
５７．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１〜２５記載の化合物の使用；
５８．前項１〜２５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；
５９．有効量の前項１〜２５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；
６０．慢性腎不全を治療するための有効成分としての、前項１〜２５記載の化合物の使用；
６１．前項１〜２５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；
６２．Ｉ型コラーゲン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記載の化合物の使用；
６３．前項２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Ｉ型コラーゲン遺伝子転写抑制組成物；
６４．Ｉ型コラーゲン遺伝子の転写を抑制するための有効成分としての、前項３記載の化合物の使用；
６５．前項３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Ｉ型コラーゲン遺伝子転写抑制組成物；
６６．Ｉ型コラーゲン遺伝子の転写を抑制するための有効成分としての、前項４記載の化合物の使用；
６７．前項４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Ｉ型コラーゲン遺伝子転写抑制組成物；
６８．Ｉ型コラーゲン遺伝子の転写を抑制するための有効成分としての、前項１０記載の化合物の使用；
６９．前項１０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Ｉ型コラーゲン遺伝子転写抑制組成物；
７０．Ｉ型コラーゲン遺伝子の転写を抑制するための有効成分としての、前項１１記載の化合物の使用；
７１．前項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Ｉ型コラーゲン遺伝子転写抑制組成物；
７２．Ｉ型コラーゲン遺伝子の転写を抑制するための有効成分としての、前項１４〜２５記載の化合物の使用；
７３．前項１４〜２５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Ｉ型コラーゲン遺伝子転写抑制組成物；
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 the compounds represented by the following formulas (I) to (XXXVIII) have the ability to suppress transcription of type I collagen gene. It came.
That is, the present invention
1. Formula (I)

[Where:
I. A represents a benzene ring or a pyridine ring, and (Y _α ) _q Y _α Is a substituent on a carbon atom and has the following X ₀ Group or Y ₀ Represents a group of the group, q represents 0, 1, 2, 3 or 4, 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 A group of groups may be condensed with ring A, and (X _α ) _p X _α Is the following X ₀ Group, Y ₀ Group and Z ₀ Represents a substituent on a carbon atom that does not belong to the group, p represents 1, 2, 3, 4 or 5, and when p is 2 or more, X _α Are the same or different, and the sum of p and q is 5 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 C1-C10 alkyl group which may be substituted with a hydrogen atom or 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 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 ) 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 A ring.
II. Q _α Represents a hydroxyl group which may be substituted or an amino group which may be substituted.
III. 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 May form a C1-C10 alkylene group which may have a substituent or a C1-C10 alkenylene group which may have a substituent.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A cinnamoyl compound represented by:
2. Formula (II)

[Where:
I. A represents a benzene ring or a pyridine ring.
II. (X _A0 ) _p X _A0 Is a substituent on a carbon atom and has the following A ₀ N from the group ₀ Represents a group included in any group up to the group, p represents 1, 2, 3, 4 or 5, 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 R1 ′) — group (R1 ′ is 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 R1'NC (= N- (O) _n -A ₁ ) -Group (R ₁ , R1 ′, 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 R1 ′) — represents a group (R1 ′ and m have 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 R1′N-group (R ₁ And R1 ′ 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 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-NR1'-group (R ₁ , A ₁ And R1 ′ represent 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 (R1 '(O) _n ) N-CR1 '' = N-R ₆ -Group (R ₁ , R1 ′, n and R ₆ Represents the same meaning as described above, and R1 ″ represents R ₁ Same or different from R ₁ Represents the same meaning as ), R ₁ -(O) _n -N = CR1'-NR ₂ -R ₆ -Group (R ₁ , N, R1 ′, R ₂ And R ₆ Represents the same meaning as described above. ), R ₂ -B ₃ -NR ₁ -CO-NR1'-R ₆ -Group (R ₂ , B ₃ , R ₁ , R1 ′ 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, a C2-C10 alkynyl group, a 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. ],
A7'-B ₂ '-B ₃ -N ((O) _n R ₁ -R ₆ The group [A7 ′ 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 -R4'-group (R ₂ And B ₁ Represents the same meaning as described above, and R4 ′ represents a C2-C10 alkylene group. ), D ₄ -R4'- group (D ₄ And R4 ′ represent the same meaning as described above. ), D ₁ -R4'- group (D ₁ And R4 ′ represent the same meaning as described above. ), (B ₀ ) -R4'-group ((b ₀ ) And R4 ′ represent the same meaning as described above. ), (C ₀ ) -R4'-group ((c ₀ ) And R4 ′ represent 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 -R4'- group (D ₃ And R4 ′ represent 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 '} R1 ′) — represents a group (n ′ is the same as or different from n and represents the same meaning as n, and R1 ′ represents the same meaning as described above); ₃ , N, R ₁ And R ₆ Represents the same meaning as described above. ], A8'-B ₂ '-CS-N ((O) _n R ₁ -R ₆ The group [A8 ′ represents a C1-C10 alkyl group or a C2-C10 haloalkyl group; ₂ 'Represents the same meaning as described above, and n, R ₁ And R ₆ Represents the same meaning as described above. ], A8'-SB ₃ '-N ((O) _n R ₁ -R ₆ The group [A8 ′, n, R ₁ And R ₆ Represents the same meaning as above, B ₃ 'Represents a carbonyl group or a sulfonyl group. ] Or A7 ''-SO ₂ -N ((O) _n R ₁ -R ₆ The group [A7 ″ 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 -R4'-group (R ₂ , B ₁ And R4 ′ represent the same meaning as described above. ), D ₄ -R4'- group (D ₄ And R4 ′ represent 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 -R4'- group (D ₁ And R4 ′ represent the same meaning as described above. ), (B ₀ ) -R4'-group ((b ₀ ) And R4 ′ represent the same meaning as described above. ), (C ₀ ) -R4'-group ((c ₀ ) And R4 ′ 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 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 A9 ′ (O) _m N = C (A ₉ ) -Group (A9 ′ represents A7 ′ or A8 ′, 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-B1'-R ₆ -Group (A ₉ And R ₆ Represents the same meaning as described above, and B1 ′ represents an oxy group or a thio group. However, when B1 ′ is an oxy group, A ₉ A ₈ is not. ) Or A ₉ -CS-B1'-R ₆ -Group (A ₉ , B1 ′ and R ₆ Represents the same meaning as described above. ) Or A7 ″ -SO ₂ -B1'-R ₆ -Groups (A7 '', B1 'and R ₆ Represents the same meaning as described above. ) Or A ₈ -SO ₂ -B1'-R ₆ -Group (A ₈ , B1 ′ and R ₆ Represents the same meaning as described above. However, A ₈ Does not become a hydrogen atom. ) Or A9'-B ₂ '-B ₃ -B1'-R ₆ -Groups (A9 ', B ₂ ', B ₃ , B1 ′ 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. ), A9'O- group (A9 'represents the same meaning as described above, provided that n is not 1), A9'-group (A9' represents the same meaning as described above, provided that n. When A is 0, A8 ′ 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 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: A10′-N ((O) _n R ₁ -SO ₂ -R ₆ -Group [A10 'represents a hydrogen atom (where n is not 0), A9'O- group (A9' represents the same meaning as described above, provided that n is not 1), A9 '. -Group (A9 'represents the same meaning as described above, except that when n is 0, A8' 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 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. ] A9''R ₁ N-SO ₂ -N ((O) _n R1 ′)-R ₆ The group [A9 ″ represents a hydrogen atom or an A9′-group (A9 ′ represents the same meaning as described above); ₁ , N, R1 ′ and R ₆ Represents the same meaning as described above. ] Or (b ₀ -SO ₂ -N ((O) _n R1 ′)-R ₆ -Group [(b ₀ ), N, R1 ′ 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 R1′N- (R ₂ S) C = N-R ₆ -Group (R ₁ , R1 ', 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 (R1′O) N—R ₆ -Group (R ₁ , R1 ′ and R ₆ Represents the same meaning as described above. )
It is.
(14) N ₀ Group: A ₁₁ -P (= O) (OR1 ')-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. R1 ′ and R ₄ Represents the same meaning as described above. ]
III. (Y _A0 ) _q Y _A0 Is a substituent on a carbon atom and has the following X ₀ Group or Y ₀ Represents a group of the group, q represents 0, 1, 2, 3 or 4, the sum of p (p represents the same meaning as described above) and q is 5 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 of groups may be condensed with the A 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 C1-C10 alkyl group which may be substituted with a hydrogen atom or 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 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, 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is aromatic or non-aromatic, monocyclic or condensed, and is condensed with ring A
IV. 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. ], A7 ''-SO ₂ -B _c -Groups (A7 '' 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 R1'N-SO ₂ -B _c -Group (R ₁ , R1 '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. ), A9'-B _c -Groups (A9 '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. ).
V. 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 C1-C10 alkylene group, or a single or the same or different M _a May form a C1-C10 alkenylene group which may be substituted with a group.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A cinnamoyl compound represented by:
3. Formula (III)

[Where:
I. A represents a benzene ring or a pyridine ring.
II. (X _A ) _p X _A Represents a substituent on a carbon atom and represents a group included in any of the following groups A to N, p represents 1, 2, 3, 4 or 5, and p is 2 X _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 R1 ′) — group (R1 ′ is 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 R1'NC (= N- (O) _n -A ₁ ) -Group (R ₁ , R1 ′, 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 'Cannot be a carbonyl group at the same time. E ₂ Is a C2-C10 alkylene group which may be substituted with an oxy group, thio group, sulfinyl group, sulfonyl group or -NR1'- group (R1 'represents the same meaning as described above), or an oxy group, A C3-C10 alkenylene group which may be substituted with a thio group, a sulfinyl group, a sulfonyl group or a —NR1′-group (where R1 ′ has the same meaning as described above); 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 R1 ′) — represents a group (R1 ′ and m have 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. ) -Substituted C2-C10 alkenyl group.
(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 bonded to an adjacent atom by a single bond, or a methine group which may be substituted with a methyl group bonded to an adjacent atom by a double bond; 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 optionally substituted by 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. ) -Substituted C2-C10 alkynyl group.
(5) Group E: A ₂ -CO-R ₅ -Group. 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 R1′N-group (R ₁ And R1 ′ 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 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-NR1'-group (R ₁ , A ₁ And R1 ′ represent 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. ].
(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. ].
(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 (R1 '(O) _n ) N-CR1 '' = N-R ₆ -Group (R ₁ , R1 ′, n and R ₆ Represents the same meaning as described above, and R1 ″ represents R ₁ Same or different from R ₁ Represents the same meaning as ), R ₁ -(O) _n -N = CR1'-NR ₂ -R ₆ -Group (R ₁ , N, R1 ′, R ₂ And R ₆ Represents the same meaning as described above. ), R ₂ -B ₃ -NR ₁ -CO-NR1'-R ₆ -Group (R ₂ , B ₃ , R ₁ , R1 ′ 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. ).
(9) Group I: A ₇ -B ₆ -N ((O) _n R ₁ -R ₆ -Group [A ₇ Is a C2-C10 alkenyl group, a C2-C10 alkynyl group, a 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. ] A7'-B ₂ '-B ₃ -N ((O) _n R ₁ -R ₆ The group [A7 ′ 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 -R4'-group (R ₂ And B ₁ Represents the same meaning as described above, and R4 ′ represents a C2-C10 alkylene group. ), D ₄ -R4'- group (D ₄ And R4 ′ represent the same meaning as described above. ), D ₁ -R4'- group (D ₁ And R4 ′ represent the same meaning as described above. ), (B) -R4′-group ((b) and R4 ′ are as defined above), (c) -R4′-group ((c) and R4 ′ are as defined above) Represents meaning), D ₂ -R ₄ -Group (D ₂ And R ₄ Represents the same meaning as described above. ), D ₃ -R4'- group (D ₃ And R4 ′ represent 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 '} R1 ′) — represents a group (n ′ is the same as or different from n and represents the same meaning as n, and R1 ′ represents the same meaning as described above); ₃ , N, R ₁ And R ₆ Represents the same meaning as described above. ], A8'-B ₂ '-CS-N ((O) _n R ₁ -R ₆ The group [A8 ′ represents a C1-C10 alkyl group or a C2-C10 haloalkyl group; ₂ 'Represents the same meaning as described above, and n, R ₁ And R ₆ Represents the same meaning as described above. ], A8'-SB ₃ '-N ((O) _n R ₁ -R ₆ The group [A8 ′, n, R ₁ And R ₆ Represents the same meaning as above, B ₃ 'Represents a carbonyl group or a sulfonyl group. ] Or A7 ''-SO ₂ -N ((O) _n R ₁ -R ₆ The group [A7 ″ 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 -R4'-group (R ₂ , B ₁ And R4 ′ represent the same meaning as described above. ), D ₄ -R4'- group (D ₄ And R4 ′ represent 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 -R4'- group (D ₁ And R4 ′ represent the same meaning as described above. ), (B) -R4′-group ((b) and R4 ′ are as defined above), (c) -R4′-group ((c) and R4 ′ are as defined above) Represents meaning), 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. ].
(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 A9 ′ (O) _m N = C (A ₉ ) -Group (A9 ′ represents A7 ′ or A8 ′, 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-B1'-R ₆ -Group (A ₉ And R ₆ Represents the same meaning as described above, and B1 ′ represents an oxy group or a thio group. However, when B1 ′ is an oxy group, A ₉ A ₈ is not. ) Or A ₉ -CS-B1'-R ₆ -Group (A ₉ , B1 ′ and R ₆ Represents the same meaning as described above. ) Or A7 ″ -SO ₂ -B1'-R ₆ -Groups (A7 '', B1 'and R ₆ Represents the same meaning as described above. ) Or A ₈ -SO ₂ -B1'-R ₆ -Group (A ₈ , B1 ′ and R ₆ Represents the same meaning as described above. However, A ₈ Does not become a hydrogen atom. ) Or A9'-B ₂ '-B ₃ -B1'-R ₆ -Groups (A9 ', B ₂ ', B ₃ , B1 ′ 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.
(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. ), A9'O- group (A9 'represents the same meaning as described above, provided that n is not 1), A9'-group (A9' represents the same meaning as described above, provided that n. When A is 0, A8 ′ 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 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. ].
(12) Group L: A10′-N ((O) _n R ₁ -SO ₂ -R ₆ -Group [A10 'represents a hydrogen atom (where n is not 0), A9'O- group (A9' represents the same meaning as described above, provided that n is not 1), A9 '. -Group (A9 'represents the same meaning as described above, except that when n is 0, A8' 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 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. ] A9''R ₁ N-SO ₂ -N ((O) _n R1 ′)-R ₆ The group [A9 ″ represents a hydrogen atom or an A9′-group (A9 ′ represents the same meaning as described above); ₁ , N, R1 ′ and R ₆ Represents the same meaning as described above. Or (b) -SO ₂ -N ((O) _n R1 ′)-R ₆ -Groups [(b), n, R1 'and R ₆ Represents the same meaning as described above. ].
(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 R1′N- (R ₂ S) C = N-R ₆ -Group (R ₁ , R1 ', 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 (R1′O) N—R ₆ -Group (R ₁ , R1 ′ and R ₆ Represents the same meaning as described above. ).
(14) Group N: A ₁₁ -P (= O) (OR1 ')-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. R1 ′ and R ₄ Represents the same meaning as described above. ].
III. (Y _A ) _q Y _A Is a substituent on a carbon atom and represents a group of the following X group and Y group, q represents 0, 1, 2, 3 or 4, and p (p represents the same meaning as described above). The sum of q and q is 5 or less, and 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 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 C1-C10 alkyl group which may be substituted with a hydrogen atom or 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 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. ) 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 }
Represents. }, 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) Group Z: -N = 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 which may be substituted with an oxy group, a thio group, or a C1-C10 alkyl group. ), -Y _b -Y _b '-Y _b '' -Group (Y _b And Y _b '' Is the same or different and represents a methylene group, an oxy group, a thio group, a sulfinyl group, or an imino group that may be substituted with a C1-C10 alkyl group; _b 'Represents a C1-C4 alkylene group which may be substituted with a halogen atom, or a C1-C4 alkylene group which may have an oxo group. ) Or -Y _c -O-Y _c '-O-group (Y _c And Y _c 'Is the same or different and represents a C1-C10 alkylene group. ).
IV. 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. ], A7 ''-SO ₂ -B _c -Groups (A7 '' 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 R1'N-SO ₂ -B _c -Group (R ₁ , R1 '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. ), A9'-B _c -Groups (A9 '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. ).
V. 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 C1-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. ).
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A cinnamoyl compound represented by:
4). Formula (IV)

[In the formula, A represents a benzene ring or a pyridine ring; _a Is a substituent on a carbon atom, a C1-C10 alkyl group substituted with a cyano group, a C1-C10 alkyl group substituted with a tetrahydropyran-4-ylidene group, or a halogen atom or a cyano group C2-C10 alkenyl group, C2-C10 alkenyl group substituted with C1-C10 alkoxycarbonyl group, C3-C10 alkynyl group substituted with 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 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 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 r ₀ O-COCO-NH- group (r ₀ 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 —NHCO— 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 an rO—CO— group (where r represents the same meaning as described above), a cyano group, or an aminocarbonyl group. C1-C10 alkyl group or rO-CO- (rO-COCH ₂ ) CH-group (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 Represents the same meaning as described above, and r ₀ 'R ₀ Same as or different from r ₀ Represents the same meaning as ) Or (r ₀ O) ₂ P (= O) CH ₂ -Group (r ₀ Represents the same meaning as described above. ), P represents 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 nitro group, r ₀ CO—NH— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkyl group or a C1-C10 alkoxy group, q represents 0, 1 or 2, and when q is 2 or more, Y _a Are the same or different.
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 alkyl group substituted with a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or 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 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 C1-C10 alkylene group or a 1,3-butadienylene group.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A cinnamoyl compound represented by:
5. Formula (V)

[Wherein, a represents a benzene ring or a pyridine ring, x represents a methine group or a nitrogen atom, and X represents _a Is a substituent on a carbon atom, a C1-C10 alkyl group substituted with a cyano group, a C1-C10 alkyl group substituted with a tetrahydropyran-4-ylidene group, or a halogen atom or a cyano group C2-C10 alkenyl group, C2-C10 alkenyl group substituted with C1-C10 alkoxycarbonyl group, C3-C10 alkynyl group substituted with 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 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 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 r ₀ O-COCO-NH- group (r ₀ 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 —NHCO— 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 an rO—CO— group (where r represents the same meaning as described above), a cyano group, or an aminocarbonyl group. C1-C10 alkyl group or rO-CO- (rO-COCH ₂ ) CH-group (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 Represents the same meaning as described above, and r ₀ 'R ₀ Same as or different from r ₀ Represents the same meaning as ) Or (r ₀ O) ₂ P (= O) CH ₂ -Group (r ₀ Represents the same meaning as described above. ), P represents 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 nitro group, r ₀ CO—NH— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkyl group or a C1-C10 alkoxy group, q represents 0, 1 or 2, and when q is 2 or more, Y _a Are the same or different.
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 alkyl group substituted with a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or 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 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 C1-C10 alkylene group or a 1,3-butadienylene group.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A cinnamoyl compound represented by:
6). Formula (VI)

[Wherein, a represents a benzene ring or a pyridine ring, x represents a methine group or a nitrogen atom, and X represents _a Is a substituent on a carbon atom, a C1-C10 alkyl group substituted with a cyano group, a C1-C10 alkyl group substituted with a tetrahydropyran-4-ylidene group, or a halogen atom or a cyano group C2-C10 alkenyl group, C2-C10 alkenyl group substituted with C1-C10 alkoxycarbonyl group, C3-C10 alkynyl group substituted with 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 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 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 r ₀ O-COCO-NH- group (r ₀ 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 —NHCO— 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 an rO—CO— group (where r represents the same meaning as described above), a cyano group, or an aminocarbonyl group. C1-C10 alkyl group or rO-CO- (rO-COCH ₂ ) CH-group (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 Represents the same meaning as described above, and r ₀ 'R ₀ Same as or different from r ₀ Represents the same meaning as ) Or (r ₀ O) ₂ P (= O) CH ₂ -Group (r ₀ Represents the same meaning as described above. ), P represents 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 nitro group, r ₀ CO—NH— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkyl group or a C1-C10 alkoxy group, q represents 0, 1 or 2, and when q is 2 or more, Y _a Are the same or different.
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 alkyl group substituted with a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or 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. ).
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A 2H-pyran-2-one compound represented by:
7). Formula (VII)

[Where X _a Is a C1-C10 alkyl group substituted with a cyano group, a C2-C10 alkenyl group substituted with a halogen atom or a cyano group, or a ₀ '-R ₁ —O— group {a ₀ 'Is a methyl group substituted with a C1-C10 alkylthio group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, HOCH ₂ -Represents a group or a cyano group, r ₁ Represents a C1-C10 alkylene group. } Or a ₆ -CONH- group (a ₆ 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. ) Or a ₇ —NHCO— group (a ₇ Represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group or a C1-C10 alkyl group substituted with a C1-C10 alkoxycarbonyl group. ). Represents.
q _a 'Represents an amino group, piperidino group, morpholino group or r substituted with a C3-C10 alkynyl group. _a '-O-group (r _a 'Represents a hydrogen atom, a C1-C10 alkyl group or a C3-C10 alkenyl group. ). ]
A 2H-pyran-2-one compound represented by:
8). Formula (VIII)

[Wherein, a represents a benzene ring or a pyridine ring, x represents a methine group or a nitrogen atom, and X represents _a Is a substituent on a carbon atom, a C1-C10 alkyl group substituted with a cyano group, a C1-C10 alkyl group substituted with a tetrahydropyran-4-ylidene group, or a halogen atom or a cyano group C2-C10 alkenyl group, C2-C10 alkenyl group substituted with C1-C10 alkoxycarbonyl group, C3-C10 alkynyl group substituted with 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 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 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 r ₀ O-COCO-NH- group (r ₀ 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 —NHCO— 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 an rO—CO— group (where r represents the same meaning as described above), a cyano group, or an aminocarbonyl group. C1-C10 alkyl group or rO-CO- (rO-COCH ₂ ) CH-group (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 Represents the same meaning as described above, and r ₀ 'R ₀ Same as or different from r ₀ Represents the same meaning as ) Or (r ₀ O) ₂ P (= O) CH ₂ -Group (r ₀ Represents the same meaning as described above. ), P represents 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 nitro group, r ₀ CO—NH— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkyl group or a C1-C10 alkoxy group, q represents 0, 1 or 2, and when q is 2 or more, Y _a Are the same or different.
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 alkyl group substituted with a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or 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. ).
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A 2H-1-benzopyran-2-one compound represented by:
9. Formula (IX)

[Where X _a '' Is a C1-C10 alkoxy group substituted with a cyano group or a hydroxymethyl group, or a ₆ -CONH- group (a ₆ 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. ) Or a ₇ —NHCO— group (a ₇ Represents a C2-C10 alkyl group substituted with a hydroxyl group, a C2-C10 alkyl group substituted with a C1-C10 alkoxy group, or a C1-C10 alkyl group substituted with a C1-C10 alkoxycarbonyl group. ) And q _a '' Represents a hydroxyl group, a C1-C10 alkoxy group or a piperidino group. ]
A 2H-1-benzopyran-2-one compound represented by:
10. Formula (X)

[Where X _I Is a C2-C4 alkenyl group substituted with a cyano group, A _I -R _I —O— group (A _I Represents a C1-C4 alkylthio group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a C1-C4 alkoxycarbonyl group, a carboxy group or a cyano group, and R _I Represents a C1-C4 alkylene group. ), A _II -(Y) _m -Z-NH- group (A _II Represents a C2-C4 alkenyl group, or a C1-C4 alkoxy group substituted with a C1-C4 alkoxy group, a C1-C4 alkoxycarbonyl group, a carboxy group or a cyano group, and y represents an oxy group or an imino group. , Z represents a carbonyl group or a sulfonyl group, and m represents 0 or 1. ) Or A _III —NHCO— group (A _III Represents a methanesulfonyl group or a C1-C4 alkyl group substituted with a hydroxyl group, a C1-C4 alkoxy group, a C1-C4 alkoxycarbonyl group, a carboxy group or a cyano group. ) And a _I Is a hydroxyl group, C1-C4 alkoxy group, C2-C4 alkenyloxy group, C2-C4 alkynyloxy group, C1-C4 alkylamino group, C2-C4 alkenylamino group, C2-C4 alkynylamino group, morpholino group or piperidino group Y _I Represents a halogen atom, a nitro group, a C1-C4 alkyl group or a C1-C4 alkoxy group, n represents 0, 1 or 2, and when n is 2, Y represents _I May be different. ]
A 2H-pyran-2-one compound represented by:
11. Formula (XI)

[Where X _I Is a C2-C4 alkenyl group substituted with a cyano group, A _I -R _I —O— group (A _I Represents a C1-C4 alkylthio group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a C1-C4 alkoxycarbonyl group, a carboxy group or a cyano group, and R _I Represents a C1-C4 alkylene group. ), A _II -(Y) _m -Z-NH- group (A _II Represents a C2-C4 alkenyl group, or a C1-C4 alkoxy group substituted with a C1-C4 alkoxy group, a C1-C4 alkoxycarbonyl group, a carboxy group or a cyano group, and y represents an oxy group or an imino group. , Z represents a carbonyl group or a sulfonyl group, and m represents 0 or 1. ) Or A _III —NHCO— group (A _III Represents a methanesulfonyl group or a C1-C4 alkyl group substituted with a hydroxyl group, a C1-C4 alkoxy group, a C1-C4 alkoxycarbonyl group, a carboxy group or a cyano group. ) And a _I Is a hydroxyl group, C1-C4 alkoxy group, C2-C4 alkenyloxy group, C2-C4 alkynyloxy group, C1-C4 alkylamino group, C2-C4 alkenylamino group, C2-C4 alkynylamino group, morpholino group or piperidino group Y _I Represents a halogen atom, a nitro group, a C1-C4 alkyl group or a C1-C4 alkoxy group, n represents 0, 1 or 2, and when n is 2, Y represents _I May be different. ]
A 2H-1-benzopyran-2-one compound represented by:
12 Formula (XII)

[Where X _II Represents an allyloxy group, a propargyloxy group, a cyanomethoxy group, a methoxyacetylamino group, a methoxycarbonylmethylaminocarbonyl group or a 2-cyanoethenyl group; _II Represents a hydroxyl group, a methoxy group or a morpholino group. ]
A 2H-pyran-2-one compound represented by:
13. Formula (XIII)

[Where X _II 'Represents a cyanomethoxy group, a methoxyacetylamino group or a 2-hydroxyethylaminocarbonyl group. ]
A 2H-1-benzopyran-2-one compound represented by:
14 Formula (XIV)

A 2H-pyran-2-one compound represented by:
15. Formula (XV)

A 2H-pyran-2-one compound represented by:
16. Formula (XVI)

A 2H-pyran-2-one compound represented by:
17. Formula (XVII)

A 2H-pyran-2-one compound represented by:
18. Formula (XVIII)

A 2H-pyran-2-one compound represented by:
19. Formula (XIX)

A 2H-pyran-2-one compound represented by:
20. Formula (XX)

A 2H-pyran-2-one compound represented by:
21. Formula (XXI)

A 2H-pyran-2-one compound represented by:
22. Formula (XXII)

A 2H-pyran-2-one compound represented by:
23. Formula (XXIII)

A 2H-1-benzopyran-2-one compound represented by:
24. Formula (XXIV)

A 2H-1-benzopyran-2-one compound represented by:
25. Formula (XXV)

A 2H-1-benzopyran-2-one compound represented by:
26. Formula (XXVI-1)

[Where X _b Is MeO-COCH ₂ NHCO-group, MeOCH ₂ CH ₂ O—CO—NH— group, MeOCH ₂ CH ₂ NH—CO—NH— group, MeSO ₂ NH-CO- group, NCCH ₂ NH—CO— group, F ₂ C═CH— group, MeO—CO— (MeO—COCH ₂ -) CH- group, MeOCH ₂ CH ₂ NH-SO ₂ -Group, MeO-NHCO- group or CH ₂ = CHCH ₂ Represents an O-NHCO- group. ],
Formula (XXVI-2)

[Where X _b 'MeOCH ₂ CO-NH- group or MeOCH ₂ CH ₂ An NH—CO— group is represented. ],
Formula (XXVI-3)

[Where X _b '' Is MeSCH ₂ CH ₂ O-group, HOCH ₂ CH ₂ OCH ₂ -Group or NC-CH ₂ CH ₂ -Represents a group. ] Or
Formula (XXVI-4)

[Where X _b “” Represents NCCH═CH— group, H ₂ NCOCH ₂ O-group, MeCOCH ₂ O-group, CH ₃ O-COCH ₂ SCH ₂ -Group, tetrahydropyran-4-ylidenemethyl group, CH ₃ O-COCO-NH- group or (CH ₃ O) ₂ P (= O) CH ₂ -Represents a group. ]
A benzaldehyde derivative represented by the formula: 6-formyl-2-[(2-methoxyethyl) aminocarbonyl] pyridine;
27. Formula (XXVII)

A benzaldehyde derivative represented by:
28. Formula (XXVIII)

A benzaldehyde derivative represented by:
29. Formula (XXIX)

A benzaldehyde derivative represented by:
30. Formula (XXX)

A benzaldehyde derivative represented by:
31. Formula (XXXI)

A benzaldehyde derivative represented by:
32. Formula (XXXII)

A benzaldehyde derivative represented by:
33. Formula (XXXIII)

A benzaldehyde derivative represented by:
34. Formula (XXXIV)

A benzaldehyde derivative represented by:
35. Formula (XXXV)

A benzaldehyde derivative represented by:
36. Formula (XXXVI)

A benzaldehyde derivative represented by:
37. Formula (XXXVII)

A benzaldehyde derivative represented by:
38. Formula (XXXVIII)

A benzaldehyde derivative represented by:
39. Formula (XXXIX)

A benzaldehyde derivative represented by:
40. Formula (XL)

A benzaldehyde derivative represented by:
41. Formula (XLI)

A benzaldehyde derivative represented by:
42. Formula (XLII)

A pyridinecarbaldehyde derivative represented by:
43. Formula (XLIII)

A benzaldehyde derivative represented by:
44. Formula (XLIV)

A benzaldehyde derivative represented by:
45. Formula (XLV)

A benzaldehyde derivative represented by:
46. The benzaldehyde derivative represented by formula (XXVI-1), formula (XXVI-2), formula (XXVI-3) or formula (XXVI-4), or 6-formyl-2-[(2- Methoxyethyl) aminocarbonyl] pyridine and the formula (XLVI)

[Wherein 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 'Is the same or different and represents a C1-C10 alkyl group. ), ROCH ₂ -Group (r represents a hydrogen atom or a C1-C10 alkyl group), r ₀ —CO— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkyl group substituted with a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or a cyano group, or r ₃ -R ₁ -Group (r ₃ Represents a phenyl group or a pyridyl group, and r ₁ Represents a C1-C10 alkylene group. ). }, 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 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 C1-C10 alkylene group or a 1,3-butadienylene group.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
(XLVI-1) characterized by reacting with a compound represented by formula (XLVI-1)

[Where X _b Is MeO-COCH ₂ NHCO-group, MeOCH ₂ CH ₂ O—CO—NH— group, MeOCH ₂ CH ₂ NH—CO—NH— group, MeSO ₂ NH-CO- group, NCCH ₂ NH—CO— group, F ₂ C═CH— group, MeO—CO— (MeO—COCH ₂ -) CH- group, MeOCH ₂ CH ₂ NH-SO ₂ -Group, MeO-NHCO- group or CH ₂ = CHCH ₂ Represents an O-NHCO- group, q _a , K _a And L _a Represents the same meaning as described above. ], Formula (XLVI-2)

[Where X _b 'MeOCH ₂ CO-NH- group or MeOCH ₂ CH ₂ Represents NH—CO— group, q _a , K _a And L _a Represents the same meaning as described above. ], Formula (XLVI-3)

[Where X _b '' Is MeSCH ₂ CH ₂ O-group, HOCH ₂ CH ₂ OCH ₂ -Group or NC-CH ₂ CH ₂ -Represents the group q _a , K _a And L _a Represents the same meaning as described above. ], Formula (XLVI-4)

[Where X _b “” Represents NCCH═CH— group, H ₂ NCOCH ₂ O-group, MeCOCH ₂ O-group, CH ₃ O-COCH ₂ SCH ₂ -Group, tetrahydropyran-4-ylidenemethyl group, CH ₃ O-COCO-NH- group or (CH ₃ O) ₂ P (= O) CH ₂ -Represents the group q _a , K _a And L _a Represents the same meaning as described above. ] Or formula (XLVI-5)

[Where q _a , K _a And L _a Represents the same meaning as described above. A process for producing a cinnamoyl compound represented by:
47. Formula (XLVII)

[Wherein A represents a benzene ring or a pyridine ring; _c Is a substituent on a carbon atom,
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, or a C2-C10 alkynyl group substituted with a hydroxymethyl group, or a _0c -R ₁ -B-r ₁ '-Group {a _0c 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. ), 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. ) Or a cyano 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 r ₀ O-COCO-NH- group (r ₀ Represents the same meaning as described above. ) Or a ₃ -Z-NH- group (a ₃ Represents a C2-C10 alkenyl group, a C1-C10 alkoxy group, a C1-C10 alkoxycarbonyl group or a C1-C10 alkyl group substituted with a cyano group, and z represents a carbonyl group or a sulfonyl group. ) Or a ₄ —NHCO— 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 O—CO— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkyl group substituted with a cyano group or an aminocarbonyl group, or r ₀ O-CO- (r ₀ O-COCH ₂ ) CH-group (r ₀ 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 Represents the same meaning as described above, and r ₀ 'R ₀ Same as or different from r ₀ Represents the same meaning as ) Or (r ₀ O) ₂ P (= O) CH ₂ -Group (r ₀ Represents the same meaning as described above. ), P represents 1, 2 or 3, and when p is 2 or more, X _c Are the same or different,
Y _a Is a halogen atom, a nitro group, r ₀ CO—NH— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkyl group or a C1-C10 alkoxy group, q represents 0, 1 or 2, and when q is 2 or more, Y _a May be the same or different.
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 C1-C10 alkylene group or a 1,3-butadienylene group.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A cinnamoyl compound represented by formula (XLVII ′)
r _c -V (XLVII ')
[r _c T _c '-Group {t _c Is 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, 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. ). }, And V represents a leaving group.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
(XLVII ″) characterized by reacting with a compound represented by the formula

[Where A, X _c , Y _a , P, q, r _c , K _a And L _a Represents the same meaning as described above.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A process for producing a cinnamoyl compound represented by:
48. Formula (XLVIII)

[Wherein A represents a benzene ring or a pyridine ring; _d Is a substituent on a carbon atom and a _0d -R ₁ -B-r ₁ '-Group {a _0d R ₂ O—CO— group (r ₂ Represents a C1-C10 alkyl group or a C2-C10 alkyl group substituted with a hydroxyl group. ) And 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 r ₀ O-COCO-NH- group (r ₀ Represents a C1-C10 alkyl group. ) Or a _3d -Z-NH- group (a _3d Represents a C1-C10 alkyl group substituted with a C1-C10 alkoxycarbonyl group, and z represents a carbonyl group or a sulfonyl group. ) Or a _4d —NHCO— group {a _4d R ₀ O—CO— group (r ₀ Represents the same meaning as described above. C1-C10 alkyl group substituted with), or r ₀ O-CO- (r ₀ O-COCH ₂ ) CH-group (r ₀ Represents the same meaning as described above. ). }, P represents 1, 2 or 3, and when p is 2 or more, X _d Are the same or different,
Y _a Is a halogen atom, a nitro group, r ₀ CO—NH— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkyl group or a C1-C10 alkoxy group, q represents 0, 1 or 2, and when q is 2 or more, Y _a May be the same or different.
q _d R _d —O— group {r _d 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 Represents the same meaning as described above, and r ₀ 'R ₀ Same as or different from r ₀ Represents the same meaning as ), 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 alkyl group substituted with a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or 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 represents a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with a C1-C10 alkoxy group. To express. However, it does not become a hydrogen atom at the same time. ) 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 C1-C10 alkylene group or a 1,3-butadienylene group.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
Hydrolysis of a cinnamoyl compound represented by the formula (XLVIII ′)

[Wherein A represents the same meaning as described above; _d 'Is a substituent on a carbon atom, a substituent on a carbon atom, a _0d '-R ₁ -B-r ₁ '-Group (a _0d 'Represents a carboxy group and r ₁ , R ₁ 'And b represent the same meaning as described above. ), Or HO-COCO-NH- group, or a _3d '-Z-NH- group (a _3d 'Represents a C1-C10 alkyl group substituted with a carboxy group, and z represents the same meaning as described above. ) Or a _4d '-NHCO- group (a _4d 'Is a C1-C10 alkyl group substituted with a carboxy group, or HO-CO- (HO-COCH ₂ ) Represents a CH- group. )
p represents the same meaning as above, and when p is 2 or more, X _d 'Is the same or different.
Y _a And q represent the same meaning as described above.
q _d 'R _d '' -O-group {r _d '' Represents 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 alkyl group substituted with a carboxy group, an aminocarbonyl group or 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 'Represents the same meaning as described above. However, it does not become a hydrogen atom at the same time. ) And K _a And L _a Represents the same meaning as described above.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A process for producing a cinnamoyl compound represented by:
49. Formula (XLIX)

[Wherein A represents a benzene ring or a pyridine ring; _e Is a substituent on a carbon atom and represents a Hb ″-group (b ″ represents an oxy group or a thio group), p represents 1, 2 or 3, and p is 2 or more. X _e Are the same or different.
Y _a Is a halogen atom, a nitro group, r ₀ CO—NH— group (r ₀ Represents a C1-C10 alkyl group. ), A C1-C10 alkyl group or a C1-C10 alkoxy group, q represents 0, 1 or 2, and when q is 2 or more, Y _a May be the same or different.
q _e R _e —O— group {r _e Is 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 Represents the same meaning as described above, and r ₀ 'R ₀ Same as or different from r ₀ Represents the same meaning as ), ROCH ₂ -Group (r represents a hydrogen atom or a C1-C10 alkyl group), r ₀ —CO— group (r ₀ Represents the same meaning as described above. ), A C1-C10 alkoxycarbonyl 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 a C1-C10 alkylene group. ). }, 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 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 C1-C10 alkylene group or a 1,3-butadienylene group.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A cinnamoyl compound represented by formula (XLIX ')
a _0e -R ₁ '-V' (XLIX ')
[Where a _0e 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. ), Rr′N—CO— group (wherein r represents the same meaning as described above, r ′ is the same as or different from r, and represents the same meaning as r), 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 the same meaning as described above, 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. ) Or a cyano group, r ₁ '' Is r ₁ Same as or different from r ₁ And V ′ represents a leaving group or a hydroxyl group.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A compound represented by formula (XLIX ″), characterized by reacting with 1,3-propane sultone or 1,4-butane sultone

[Where X _e 'A _0e '-R ₁ '' -B ''-group {a _0e 'A _0e -Group (a _0e Represents the same meaning as described above. ), 3-sulfopropyl group or 4-sulfobutyl group, r ₁ '' And b '' represent the same meaning as described above. }, A, Y _a , P, q, q _e , K _a And L _a Represents the same meaning as described above.
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. Although the range of choices of substituents selected is the same among groups, it means that the selected substituents may be the same or different as long as they are selected within the range. . ]
A process for producing a cinnamoyl compound represented by:
50. Use of the compound according to the above 1 to 25 as an active ingredient for suppressing transcription of a type I collagen gene;
51. A type I collagen gene transcription repressing composition comprising the compound according to the above 1 to 25 and an inert carrier;
52. Use of the compound described in the above item 1-25 as an active ingredient for improving tissue fibrosis by reducing the expression level of type I collagen gene and leading to a decrease in collagen accumulation amount;
53. A composition for improving tissue fibrosis, comprising the compound according to any one of 1 to 25 above and an inert carrier;
54. 26. A method for improving tissue fibrosis, comprising administering an effective amount of the compound described in the above item 1 to 25 to a mammalian patient in need of a treatment for improving tissue fibrosis;
55. Use of the compound according to the above 1 to 25 as an active ingredient for suppressing the action of TGF-β;
56. A TGF-β action-inhibiting composition comprising the compound according to 1 to 25 above and an inert carrier;
57. Use of the compound according to the above item 1 to 25 as an active ingredient for obtaining a hair nourishing effect by inhibiting the promotion of the transition to the hair regression phase by TGF-β and leading to the extension of the hair growth phase;
58. A hair nourishing composition comprising the compound according to the above item 1 to 25 and an inert carrier;
59. A method of hair restoration comprising administering an effective amount of the compound described in the above item 1 to 25 to a mammalian patient in need of hair restoration treatment;
60. Use of the compound according to the above item 1 to 25 as an active ingredient for treating chronic renal failure;
61. A therapeutic agent for chronic renal failure, comprising the compound according to any one of 1 to 25 above and an inert carrier;
62. Use of the compound according to item 2 as an active ingredient for suppressing transcription of a type I collagen gene;
63. A type I collagen gene transcription repressing composition comprising the compound of the preceding item 2 and an inert carrier;
64. Use of the compound according to item 3 as an active ingredient for suppressing transcription of a type I collagen gene;
65. A composition for inhibiting transcription of type I collagen gene, comprising the compound according to item 3 above and an inert carrier;
66. Use of the compound according to item 4 as an active ingredient for suppressing transcription of a type I collagen gene;
67. A composition for repressing transcription of type I collagen gene, comprising the compound according to item 4 and an inert carrier;
68. Use of the compound according to the above item 10 as an active ingredient for suppressing transcription of a type I collagen gene;
69. A composition for repressing transcription of type I collagen gene, comprising the compound according to item 10 above and an inert carrier;
70. Use of the compound according to the above item 11 as an active ingredient for suppressing transcription of a type I collagen gene;
71. A composition for repressing transcription of type I collagen gene, comprising the compound according to item 11 above and an inert carrier;
72. Use of the compound according to the above 14 to 25 as an active ingredient for suppressing transcription of a type I collagen gene;
73. A composition for suppressing transcription of type I collagen gene, comprising the compound according to the above 14 to 25 and an inert carrier;
Etc. are provided.

  According to the present invention, a composition (that is, a collagen accumulation inhibitor or a fibrosis therapeutic agent) that improves the fibrosis of a tissue by reducing the expression level of a type I collagen gene in the tissue and decreasing the amount of collagen accumulation. Development and provision are possible.

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.
In the present invention, examples of the leaving group include an alkylsulfonyloxy group such as a mesyloxy group, an arylsulfonyloxy group such as a tosyloxy group, an alkoxysulfonyloxy group such as a methoxysulfonyloxy group, such as a bromine atom, and the like. Halogen atoms and the like.

Cinnamoyl compounds represented by the formulas (I), (II), (III) and (IV) (hereinafter sometimes referred to as the present compounds (I), (II), (III) and (IV), respectively). In the case where the A ring is a pyridine ring, the cinnamoyl compound represented by the formula (V), the 2H-pyran-2-one compound represented by the formula (VI) and the 2H-1 represented by the formula (VIII) -In the case where the a ring is a pyridine ring and x is a nitrogen atom in the -benzopyran-2-one compound (hereinafter also referred to as the present compounds (V), (VI) and (VIII), respectively) Also includes its N-oxide.
In the compounds (V), (VI) and (VIII) of the present invention, when x is a methine group, the methine group has no substituent.

  Compounds (I) to (VI) and (VIII) of the present invention, 2H-pyran-2-one compounds represented by the formula (VII) (hereinafter sometimes referred to as the present compound (VII)), formula (IX) 2H-1-benzopyran-2-one compound represented by formula (X), 2H-pyran-2-one compound represented by formula (X), 2H-1-benzopyran-2-one compound represented by formula (XI), formula 2H-pyran-2-one compound represented by (XII) and 2H-1-benzopyran-2-one compound represented by formula (XIII) (hereinafter, the compounds (VII), (IX), (X ), (XI), (XII) and (XIII).), 2H-pyran-2-one compounds represented by formulas (XIV) to (XXII) (hereinafter referred to as compounds of the present invention (XIV), respectively) ) To (XXII)) and 2H-1-benzopyran-2-one compounds represented by formulas (XXIII) to (XXV) (hereinafter referred to as the present compounds (XXIII) to (XXV), respectively) May be noted.) Their pharmacologically acceptable salts also represent simultaneously. The pharmacologically acceptable salt is a salt of the present compound (I) to (XXV) (hereinafter sometimes referred to as the present compound) with an inorganic acid, a salt with an organic acid, or 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.

In the compound (II) of the present invention, X _A0 , Y _A0 , Q _A0 , K _A0 and L _A0 are each independently D ₁ , D ₂ , D ₃ , D ₄ , D ₅ , R ₀ , R ₀ ′, R ₀ ″, R ₁ , R1 ′, R1 ″, R ₂ , R ₂ ′, R ₃ , R ₄ , R4 ′, R ₅ , R ₆ , A ₁ , A ₂ , A ₃ , A ₄ , A _{5 , A 6, A 7, A7} ', A7'', A 8, A8', A 9, A9 ', A9'', A 10, A10', A 11, B, B ', B 0, B 1, _{B1 ', 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, _{a ', Y b, Y b} ', Y b ' groups represented by', _{Y c} and _{Y c} ', and, k, k', l, m, m ', an integer represented by n and n' Represented by
_X A in the present invention the compound _{(III), Y A, Q} A, K A and _{L A} are independently of one _{another, D 1, D 2, D} 3, D 4, D 5, R 0, R 0 ', R ₀ ″, R ₁ , R1 ′, R1 ″, R ₂ , R ₂ ′, R ₃ , R ₄ , R4 ′, R ₅ , R ₆ , A ₁ , A ₂ , A ₃ , A ₄ , A _{5 , A 6, A 7, A7} ', A7'', A 8, A8', A 9, A9 ', A9'', A 10, A10', A 11, B, B ', B 0, B 1, _{B1 ', 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 And 'groups represented by, _{and, k, k' Y c,} l, m, m is represented by an integer represented by ', n and n'.
X _a , Y _a and q _a in the compounds (IV), (V), (VI) and (VIII) of the present invention are independently of each other a ₀ , a ₁ , a ₁ ′, a ₂ , a ₃ , a ₄ , a ₅ , b, r, r ′, r ₀ , r ₀ ′, r ₁ , r ₁ ′, r ₂ , r ₃ , r ₄ , r ₄ ′, r _a , y and z And an integer represented by l.
In the present invention, (XLVII), (XLVII ' ) and (XLVII' _X in ') c, _{Y a,} and _{r c,} independently of one _{another, a 0c, a 1, a} 1', a 2, a 3, a group represented by a ₄ , a ₅ , b, r, r ′, r ₀ , r ₀ ′, r ₁ , r ₁ ′, r ₂ , r ₃ , y and z, and an integer represented by l Represented by
In the present invention, X _d , X _d ′, Y _a , q _d, and q _d ′ in (XLVIII) and (XLVIII ′) are independently of each other a _0d , a _0d ′, a _3d , a _3d ′, a _By groups represented by _4d , a _4d ′, b, r ₀ , r ₀ ′, r ₁ , r ₁ ′, r ₂ , r ₃ , r ₄ , r ₄ ′, r _d , r _d ″ and z expressed.
In the present invention, X _e , X _e ′, Y _a and q _e in (XLIX) and (XLIX ″) are independently of each other a _0e , a ₁ , a ₁ ′, b ″, r, r ′. , R ₀ , r ₀ ′, r ₁ , r ₁ ″, r ₂ , r ₃ , r ₄ , r ₄ ′ and r _e , and an integer represented by l.

In the group Y ₀ that can be substituted for Y _α of the compound (I) of the present invention, the “6-10-membered aryl group” represents a group forming a monocyclic or condensed aromatic hydrocarbon ring, for example, , A phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 6-indanyl group, and the like, and a “5- to 10-membered heteroaryl group” is a group that forms a monocyclic 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 and the like can be mentioned. The group that forms a 3-10 membered hydrocarbon ring or heterocyclic ring that may contain a saturated bond includes a monocyclic ring or a condensed ring, and includes a 2-cyclohexenyl group, a 2-morpholinyl group, a 4-piperidyl group, and the like. These may be a single or a plurality of the same or different. _a - it may be substituted with group.
In the substituent group Z ₀ that Y _α of the compound (I) of the present invention can take, the “group condensed with ring A” is a halogen atom, a C1-C10 alkoxy group, a C3-C10 alkenyloxy group, a C3-C10 alkynyl group. You may have a single or the same or different atom or group chosen from an oxy group, a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a sulfinyl group, or a sulfonyl group.
In R _a0 of the substituent E ₀ group that X _A0 of the compound (II) of the present invention can take, the “ _optionally substituted 5-7-membered aryl group or heteroaryl group” means a monocyclic or condensed ring Represents a group forming an aromatic hydrocarbon ring or a group forming a monocyclic or condensed aromatic heterocyclic ring, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 6-indanyl group, a 2-furyl group, A 3-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. May be substituted with the M _a -group.

In the compounds of the present invention (I) and (II), (d ₀ ) of the substituent Y ₀ group that Ya and Y _A0 can take, “substituted by a carbonyl group or a thiocarbonyl group, and further, an oxy group, a thio group, The —NR ₁ — group (R ₁ represents the same meaning as described above), a sulfinyl group or a sulfonyl group which may be substituted with a 5- to 12-membered hydrocarbon ring is one of carbon atoms or A plurality of them are replaced with a carbonyl group or a thiocarbonyl group, and one or more of carbon atoms is an oxy group, a thio group, a —NR ₁ — group (R ₁ represents the same meaning as described above), It represents forming a 5- to 12-membered hydrocarbon ring which may be replaced by one or a plurality of the same or different groups selected from a sulfinyl group or a sulfonyl group.
In the compounds (I) and (II) of (e ₀ ) of the substituent Y ₀ group that Ya and Y _A0 can take, “carbonyl group, thiocarbonyl group, oxy group, thio group, —NR ₁ -group” (R ₁ represents the same meaning as described above), and forms a 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group. A single group selected from a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a —NR ₁ — group (where R ₁ represents the same meaning as described above), a sulfinyl group or a sulfonyl group, or the same or different Represents a 5- to 12-membered hydrocarbon ring which may be replaced by

In the compound (III) of the present invention (III), in the substituent B group ( _A ) that X _A can take, “an oxy group, a thio group, a sulfinyl group, a sulfonyl group, or a —NR1′-group (R1 ′ is the same as defined above) The C2-C10 alkylene group which may be substituted with the meaning of.) Is a group in which one or more of carbon atoms are an oxy group, a thio group, a sulfinyl group, a sulfonyl group, or an —NR1′-group (R1 ′ is Represents a C2-C10 alkylene group which may be replaced by a single group or a plurality of the same or different groups selected from the above, and represents “an oxy group, a thio group, a sulfinyl group, a sulfonyl group” A C3-C10 alkenylene group which may be substituted with a group or —NR1′-group (R1 ′ has the same meaning as described above) means that one or more carbon atoms are an oxy group or a thio group. Sulfinyl group, sulfonyl group or A C3-C10 alkenylene group which may be replaced with a single group or a plurality of the same or different groups selected from the group -NR1'- (R1 'represents the same meaning as described above).
The present invention compound of formula (III), 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 Represents a C1-C10 alkylene group which may be substituted with the same meaning as the above.) “One or more of carbon atoms may be substituted with a methyl group, or one or more of carbon atoms may be substituted. , 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), and is replaced by a single group or a plurality of the same or different groups. Represents a C2-C10 alkylene group, which 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). A good C2-C10 alkenylene group is carbon One or more of the atoms may be substituted with a methyl group, or one or more of the carbon atoms may be an oxy group, a thio group, a sulfinyl group, a sulfonyl group, or a —NR ₁ — group (wherein R ₁ is Represents a C2-C10 alkenylene group which may be replaced by a single group or a plurality of groups which are the same or different from each other.

The groups belonging to the X ₀ group, the Y ₀ group and the Z ₀ group that Y _α of the compound (I) of the present invention can take are exemplified in the following Table X, Table Y and Table Z, respectively.
Group A ₀ , B ₀ , C ₀ , D ₀ , E ₀ , F ₀ , F ₀ , G ₀ , H ₀ , I ₀ , J ₀ of X _A0 of the compound (II) of the present invention. The groups belonging to the group, the K ₀ group, the L ₀ group, the M ₀ group and the N ₀ group are shown in Table 1, Table 2, Table 3, Table 4, Tables 5 to 7, Tables 8 to 10, 11 to 13, Table 14, Table 15, Table 16, Table 17, Table 18, Table 19, and Table 20, each group belonging to X ₀ group, Y ₀ group, and Z ₀ group that Y _A0 can take, , Exemplified in Table 21, Table 22, and Table 23 below, and Q ₀ and T ₀ are exemplified in Table 24 and Table 25 below, respectively.
Possible Group A _{X A} of the present invention the compound (III), B group, C group, D group, E group, F group, G group, H group, I group, J group, K group, L group, M group And groups belonging to the N group are shown in Table 1, Table 2, Table 3, Table 4, Table 5 to 7, Table 8 to 10, Table 11 to 13, Table 14, Table 15, Table 16, and Table 17, respectively. Table 18, Table 19 and Table 20 are exemplified, and groups belonging to X group, Y group and Z group which Y _A can take are exemplified in Table 21, Table 22 and Table 23 below, respectively, and Q and T Are illustrated in Table 24 and Table 25 below, respectively.

The groups belonging to the groups A _{0 to} N _{0 and} groups A to N are exemplified in the following Tables 1 to 20, but 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１０に例示する。

Belonging group F ₀ group and F group, exemplified in Tables 8 to 10.

Ｇ_０群及びＧ群に属する基を、表１１〜表１３に例示する。

The group belonging to G ₀ group and G group, are illustrated in Table 11 to Table 13.

Ｈ_０群及びＨ群に属する基を、表１４に例示する。

Belonging group H ₀ group and H group, exemplified in Table 14.

Ｉ_０群及びＩ群に属する基を、表１５に例示する。

Table 15 shows 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１６に例示する。

Table 16 shows groups belonging to the _J0 group and the J group.

Ｋ_０群及びＫ群に属する基を、表１７に例示する。

Table 17 illustrates 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１８に例示する。

Table 18 shows the groups belonging to the _L0 group and the L group.

Ｍ_０群及びＭ群に属する基を、表１９に例示する。

Table 19 shows groups belonging to the _M0 group and the M group.

Ｎ_０群及びＮ群に属する基を、表２０に例示する。

Table 20 shows the groups belonging to the _N0 group and the N group.

Said, the group belonging to X ₀ group ~Z ₀ group and X groups ~Z group will be illustrated in the following table 21 to table 23, 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 21 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２２に例示する。

Belonging group Y ₀ group and Y group is exemplified in table 22.

Ｚ_０群又はＺ群と縮環したＡ環を、表２３に例示する。

The A ring condensed with Z ₀ group or Z group, is illustrated in Table 23.

Q _A0 and Q _A are illustrated in Table 24.

Ｔ_Ａ０及びＴ_Ａを、表２５に例示する。

T _A0 and T _A are illustrated in Table 25.

［式中、Ａ、Ｘ_α、Ｙ_α、ｐ、ｑ及びＱ_αは、前記と同一の意味を表し、ｘは、メチン基又は窒素原子を表す。］
で示される2H-ピラン-2-オン化合物があげられる。2H-ピラン−2-オン化合物（I’）において、ｘがメチン基の場合、メチン基は置換基を有さない。具体的には、2H-ピラン−2-オン化合物（I’）において、Ｑ_αが置換されてもよい水酸基の場合があげられる。
本発明化合物（II）として、例えば、式（II’）

［式中、Ａ、Ｘ_Ａ０、Ｙ_Ａ０、ｐ、ｑ及びＱ_Ａ０は、前記と同一の意味を表し、ｘは、メチン基又は窒素原子を表す。］
で示される2H-ピラン−2-オン化合物があげられる。2H-ピラン−2-オン化合物（II’）において、ｘがメチン基の場合、メチン基は置換基を有さない。具体的には、2H-ピラン−2-オン化合物（II’）において、Ｑ_Ａ０が、水酸基、Ａ９’−Ｏ−基（Ａ９’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。）の場合があげられる。
本発明化合物（III）として、例えば、式（III’）

［式中、Ａ、Ｘ_Ａ、Ｙ_Ａ、ｐ、ｑ及びＱ_Ａは、前記と同一の意味を表し、ｘは、メチン基又は窒素原子を表す。］
で示される2H-ピラン−2-オン化合物があげられる。2H-ピラン−2-オン化合物（III’）において、ｘがメチン基の場合、メチン基は置換基を有さない。具体的には、2H-ピラン−2-オン化合物（III’）において、Ｑ_Ａが、水酸基、Ａ９’−Ｏ−基（Ａ９’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。）の場合があげられる。更に具体的には、2H-ピラン−2-オン化合物（III’）において、Ｑ_Ａが、水酸基、Ａ９’−Ｏ−基（Ａ９’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。）の場合、Ｘ_Ａ−基は、Ｆ群、Ｉ群又はＫ群に属する置換基を表す。
本発明化合物（IV）として、例えば、ｑ_ａが、ｒ_ａ−Ｏ−基（ｒ_ａは、前記と同一の意味を表す。）の場合があげられる。
本発明化合物（V）として、例えば、ｑ_ａが、ｒ_ａ−Ｏ−基（ｒ_ａは、前記と同一の意味を表す。）の場合があげられる。
本発明化合物（VI）として、例えば、ｑ_ａが、ｒ_ａ−Ｏ−基（ｒ_ａは、前記と同一の意味を表す。）の場合があげられる。
本発明化合物（VII）として、例えば、ｑ_ａ’が、ｒ_ａ’−Ｏ−基（ｒ_ａ’は、前記と同一の意味を表す。）の場合があげられる。
本発明化合物（VIII）として、例えば、ｑ_ａが、ｒ_ａ−Ｏ−基（ｒ_ａは、前記と同一の意味を表す。）の場合があげられる。
本発明化合物（IX）として、例えば、ｑ_ａ’’が、水酸基又はC1-C10アルコキシ基の場合があげられる。
本発明化合物（X）として、例えば、式（X’）

［式中、Ｘ_Ｉ及びａ_Ｉは、前記と同一の意味を表す。］
で示される2Ｈ-ピラン-2-オン化合物があげられる。
本発明化合物（XI）として、例えば式（XI’）

［式中、Ｘ_Ｉ及びａ_Ｉは、前記と同一の意味を表す。］
で示される2Ｈ-1-ベンゾピラン-2-オン化合物があげられる。 Examples of the compound (I) of the present invention include those represented by the formula (I ′)

[Wherein, A, X _α , Y _α , p, q, and Q _α represent the same meaning as described above, and x represents a methine group or a nitrogen atom. ]
2H-pyran-2-one compounds represented by the formula: In the 2H-pyran-2-one compound (I ′), when x is a methine group, the methine group has no substituent. Specifically, in the 2H-pyran-2-one compound (I ′), Q _α may be an optionally substituted hydroxyl group.
As the compound (II) of the present invention, for example, the compound of formula (II ′)

[Wherein, A, X _A0 , Y _A0 , p, q and Q _A0 represent the same meaning as described above, and x represents a methine group or a nitrogen atom. ]
2H-pyran-2-one compounds represented by the formula: In the 2H-pyran-2-one compound (II ′), when x is a methine group, the methine group has no substituent. Specifically, in the 2H-pyran-2-one compound (II ′), Q _A0 is a hydroxyl group, an A9′-O— group (A9 ′ represents the same meaning as described above), or M _c —O. - group (. M _c is representative of the same meaning as above) when the like.
As the compound (III) of the present invention, for example, the compound of formula (III ′)

[Wherein, A, X _A , Y _A , p, q and Q _A represent the same meaning as described above, and x represents a methine group or a nitrogen atom. ]
2H-pyran-2-one compounds represented by the formula: In the 2H-pyran-2-one compound (III ′), when x is a methine group, the methine group has no substituent. Specifically, in 2H-pyran-2-one compound (III ′), Q _A represents a hydroxyl group, an A9′-O— group (A9 ′ represents the same meaning as described above), or M _c —O. - group (. M _c is representative of the same meaning as above) when the like. More specifically, in the 2H-pyran-2-one compound (III ′), Q _A is a hydroxyl group, an A9′-O— group (A9 ′ represents the same meaning as described above), or M _c —. (the _{M c} represents the same meaning.) O-group case, _{X a} - group represents a substituent belonging to the group F, I group or the K group.
As the present invention compound (IV), for example, _{q a is,} r a -O- group _{(r a} represents. The same meaning as above) When the like.
As the present invention compound (V), for example, _{q a} it _is, r a -O- group _{(r a} represents. The same meaning as above) When the like.
As the present invention compounds (VI), for example, _{q a is,} r a -O- group _{(r a} represents. The same meaning as above) When the like.
Examples of the compound (VII) of the present invention include a case where q _a ′ is a r _a ′ —O— group (where r _a ′ represents the same meaning as described above).
As the present invention compound (VIII), for example, _{q a is,} r a -O- group _{(r a} represents. The same meaning as above) When the like.
Examples of the compound (IX) of the present invention include a case where q _a ″ is a hydroxyl group or a C1-C10 alkoxy group.
Examples of the compound (X) of the present invention include those represented by the formula (X ′)

[Wherein, X _I and a _I represent the same meaning as described above. ]
2H-pyran-2-one compounds represented by the formula:
As the compound (XI) of the present invention, for example, the formula (XI ′)

[Wherein, X _I and a _I represent the same meaning as described above. ]
2H-1-benzopyran-2-one compounds represented by the formula:

で示される2H-ピラン-2-オン化合物、
式（XV）

で示される2H-ピラン-2-オン化合物、
式（XVI）

で示される2H-ピラン-2-オン化合物、
式（XVII）

で示される2H-ピラン-2-オン化合物、
式（XVIII）

で示される2H-ピラン-2-オン化合物、
式（XIX）

で示される2H-ピラン-2-オン化合物、
式（XX）

で示される2H-ピラン-2-オン化合物、
式（XXI）

で示される2H-ピラン-2-オン化合物、
式（XXII）

で示される2H-ピラン-2-オン化合物、
式（XXIII）

で示される2H-1-ベンゾピラン-2-オン化合物、
式（XXIV）

で示される2H-1-ベンゾピラン-2-オン化合物、
式（XXV）

で示される2H-1-ベンゾピラン-2-オン化合物等を挙げることができる。 Among the compounds (I) of the present invention, examples of typical compounds include
Formula (XIV)

A 2H-pyran-2-one compound represented by:
Formula (XV)

A 2H-pyran-2-one compound represented by:
Formula (XVI)

A 2H-pyran-2-one compound represented by:
Formula (XVII)

A 2H-pyran-2-one compound represented by:
Formula (XVIII)

A 2H-pyran-2-one compound represented by:
Formula (XIX)

A 2H-pyran-2-one compound represented by:
Formula (XX)

A 2H-pyran-2-one compound represented by:
Formula (XXI)

A 2H-pyran-2-one compound represented by:
Formula (XXII)

A 2H-pyran-2-one compound represented by:
Formula (XXIII)

A 2H-1-benzopyran-2-one compound represented by:
Formula (XXIV)

A 2H-1-benzopyran-2-one compound represented by:
Formula (XXV)

2H-1-benzopyran-2-one compounds represented by the formula:

  The compound of the present invention is a novel compound. JP09227547 and WO00 / 20371 disclose a compound having a certain conceptual skeleton, but there is no specific description of a compound having a structure similar to the compound of the present invention. Further, this document does not describe the effect of suppressing transcription of the type I collagen gene in the tissue, and thus the effect of suppressing the amount of accumulated collagen.

本発明化合物（II）は、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（AO’）（式中、Ｑ_Ａ０、Ｋ_Ａ０及びＬ_Ａ０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。

本発明化合物（III）は、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（A’）（式中、Ｑ_Ａ、Ｋ_Ａ及びＬ_Ａ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。

本発明化合物（IV）は、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（a’）（式中、Ｑ_ａ、Ｋ_ａ及びＬ_ａ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。

式（a）で示される化合物の一部は、例えば文献（ＥＰ３３０６４５）に記載されており公知であるが、前記の、式（XXVI-1）、（XXVI-2）、（XXVI-3）及び（XXVI-4）で示されるベンズアルデヒド誘導体（以下、本発明ベンズアルデヒド誘導体と記すこともある）、及び、6-ホルミル-2-[(2-メトキシエチル)アミノカルボニル]ピリジン（以下、本発明ピリジンカルバ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。
本発明化合物ベンズアルデヒド誘導体は、例えば、式（XXVI-a）

で示される化合物を、グリシン メチルエステル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、ピリジン、トリエチルアミン、Ｎ，Ｎ−ジメチルアニリン、トリブチルアミン、Ｎ−メチルモルホリン等の有機塩基、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基等があげられる。当該反応に供せられる試剤の量は、化合物（XXVI-a）１モルに対して、グリシン メチルエステルは通常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、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、目的の本発明化合物を得ることができる。
また、本発明ベンズアルデヒド誘導体は、例えば、式（XXVI-b）

で示される化合物を、ジクロロメタン中でトリエチルアミン等の塩基の存在下、塩化オキザリルで活性化されたジメチルスルホキシドを用いて酸化する（ＳＹＮＴＨＥＳＩＳ（１９８１）,１６５）ことで製造することができる。
式（XXVI-b）で示される化合物は、例えば式（XXVI-c）

で示される化合物を、メトキシアセチルクロリドと反応させることで製造することができる。化合物（XXVI-c）とメトキシアセチルクロリドとの反応は、前記の化合物（XXVI-a）とグリシン メチルエステルとの反応と、同様にして行うことができる。
また、本発明ベンズアルデヒド誘導体は、例えば、式（XXVI-d）

で示される化合物を、2-メトキシエチルアミンと反応させることで製造することができる。化合物（XXVI-d）と2-メトキシエチルアミンとの反応は、前記の化合物（XXVI-a）とグリシン メチルエステルとの反応と、同様にして行うことができる。
化合物（XXVI-d）は、例えば、Ｊ.Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍ.（２００１）,４４,３６２等の文献に記載されており公知である。
本発明ピリジンカルバルデヒド誘導体は、式（XXVI-e）

で示される化合物を、2-メトキシエチルアミンと反応させることで製造することができる。化合物（XXVI-e）と2-メトキシエチルアミンとの反応は、前記の化合物（XXVI-a）とグリシン メチルエステルとの反応と、同様にして行うことができる。化合物（XXVI-e）は、2-カルボキシ-6-ホルミルピリジンと塩化ホスホリル、塩化チオニル又は３塩化リン等の塩素化剤とを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。当該反応に供せられる試剤の量は、2-カルボキシ-6-ホルミルピリジン１モルに対して、塩素化剤は通常１〜１０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又はそれらの混合物があげられる。反応終了後、揮発物を減圧留去することで、化合物（XXVI-e）を得ることができる。2-カルボキシ-6-ホルミルピリジン例えば、Ｂｉｏｏｒｇ．Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍ．Ｌｅｔｔｅｒｓ（２００３）１３，６０９等の文献に記載されており公知である。
本発明化合物（IV）のうち、前記の式（XLVI-1）、（XLVI-2）、（XLVI-3）、（XLVI-4）及び（XLVI-5）で示されるシンナモイル化合物は、本発明ベンズアルデヒド誘導体又は本発明ピリジンカルバルデヒド誘導体と、前記の化合物(XLVI)とを反応させることにより、製造することができる。
〔本発明化合物の製造法Ｂ〕
本発明化合物のうち、前記の式（XLVII’’）で示されるシンナモイル化合物は、前記の式（XLVII）で 示されるシンナモイル化合物と、前記の式（XLVII’）で示される化合物とを反応させることにより製造することができる。

該反応の方法としては、例えば、化合物（XLVII）と化合物（XLVII’）とを塩基の存在下で反応させる方法をあげることができる。
化合物（XLVII）と化合物（XLVII’）との塩基の存在下での反応は、通常、溶媒中で行われる。反応に用いられる溶媒としては、例えば、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、ヘキサメチルホスホラミド等のリン酸アミド化合物類、アセトン、メチルエチルケトン等のケトン類等があげられる。
反応に用いられる塩基としては、例えば、水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類、酸化銀等があげられる。
化合物（XLVII’）としては、例えば、メタンスルホン酸メチル等のアルキルスルホン酸エステル類、ｐ−トルエンスルホン酸のメチルエステル、ｐ−トルエンスルホン酸の2-メトキシエチルエステル等のアリールスルホン酸エステル類、ジメチル硫酸等の硫酸エステル類、ヨウ化メチル、2-クロロエチルジメチルアミン、臭化アリル、臭化プロパルギル、ブロモ酢酸メチル、ブロモアセトニトリル、2-ブロモエタノール、臭化ベンジル、ブロモアセトン等のハライド類等があげられる。
反応に用いられる試剤の量は、化合物（XLVII）１モルに対して、塩基は、通常、１モル〜２モルの割合、化合物（XLVII’）は、通常、１モル〜２モルの割合である。
反応温度は、通常、０℃〜１００℃の範囲内、反応時間は、通常、１時間〜２００時間の範囲内である。
反応終了後、反応混合物を有機溶媒抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、シンナモイル化合物（XLVII’’）を単離することができる。単離された化合物（XLVII’’）はクロマトグラフィー、再結晶等によりさらに精製することもできる。
〔本発明化合物の製造法Ｃ〕
本発明化合物のうち、前記の式（XLVIII’） で示されるシンナモイル化合物は、前記の式（XLVIII）で示されるシンナモイル化合物を加水分解することにより、製造することができる。

シンナモイル化合物（XLVIII）の加水分解は、酸又は塩基の存在下、通常、溶媒中で行われる。反応に用いられる溶媒としては、例えば、水、メタノール、エタノール等のアルコール類、アセトン、メチルエチルケトン等のケトン類もしくはそれらの混合物等があげられる。
反応に用いられる酸としては、例えば、塩酸、硫酸、臭化水素酸等の無機酸類、ｐ−トルエンスルホン酸等の有機酸類等があげられる。
反応に用いられる塩基としては、例えば、水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類等があげられる。
反応に用いられる試剤の量は、化合物（XLVIII）１モルに対して、塩基は、通常、１モル〜１０モルの割合である。
反応温度は、通常、０℃〜溶媒還流温度の範囲内、反応時間は、通常、１時間〜２００時間の範囲内である。
反応終了後、反応混合物を有機溶媒抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、シンナモイル化合物（XLVIII’）を単離することができる。単離された化合物（XLVIII’）はクロマトグラフィー、再結晶等によりさらに精製することもできる。
〔本発明化合物の製造法Ｄ〕
本発明化合物のうち、前記の式（XLIX’’）で示されるシンナモイル化合物は、前記の式（XLIX）で 示されるシンナモイル化合物と、前記の式（XLIX’）で示される化合物、1,3-プロパンスルトン又は1,4-ブタンスルトンとを反応させることにより製造することができる。

該反応の方法として例えば、化合物（XLIX）と、化合物（XLIX’）でＶ’が脱離基である化合物、1,3-プロパンスルトン又は1,4-ブタンスルトンとを、塩基の存在下で反応させる方法をあげることができる。
化合物（XLIX）と、化合物（XLIX’）でＶ’が脱離基である化合物、1,3-プロパンスルトン又は1,4-ブタンスルトンとの、塩基の存在下での反応は、前記の化合物（XLVII）と化合物（XLVII’）との反応と、同様にして行うことができる。
化合物（XLIX’）でＶ’が脱離基である化合物としては、例えば、メタンスルホン酸２-メトキシエチル等のアルキルスルホン酸エステル類、ｐ−トルエンスルホン酸の2-メトキシエチルエステル等のアリールスルホン酸エステル類、２-クロロエチルジメチルアミン、臭化アリル、臭化プロパルギル、ブロモ酢酸メチル、ブロモアセトニトリル、2-ブロモエタノール、ブロモアセトン等のハライド類等があげられる。
また、該反応の方法として例えば、化合物（XLIX）と、化合物（XLIX’）でＶ’が水酸基である化合物とを、トリフェニルホスフィンとアゾジカルボン酸エステルの存在下に脱水反応させる方法をあげることができる。
該反応は、通常、溶媒中で行われ、反応に用いられる溶媒として、例えば、テトラヒドロフラン等のエーテル類があげられ、アゾジカルボン酸エステルとしては、例えば、ジエチルアゾジカルボキシレートがあげられる。
反応に用いられる試剤の量は、化合物（XLIX）１モルに対して、トリフェニルホスフィン及びアゾジカルボン酸エステルは、通常、１モル〜２モルの割合、化合物（XLIX’）は、通常、１モル〜２モルの割合である。
反応温度は、通常、０℃〜室温の範囲内、反応時間は、通常、１時間〜２００時間の範囲内である。
反応終了後、反応混合物を有機溶媒抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、シンナモイル化合物（XLIX’’）を単離することができる。単離された化合物（XLIX’’）はクロマトグラフィー、再結晶等によりさらに精製することもできる。 [Production Method A of Compound of the Present Invention]
The compound (I) of the present invention comprises a compound represented by the formula (α) (wherein A, X _α , Y _α , p and q represent the same meaning as described above), a compound represented by the formula (α ′) (formula In which Q _α , K _α and L _α represent the same meaning as described above) (refer to Indian J. Chem. (1974), 12, 956 and JP 50046666). can do.

The compound (II) of the present invention comprises a compound represented by the formula (AO) (wherein A, X _A0 , Y _A0 , p and q represent the same meaning as described above), a compound represented by the formula (AO ′) (formula Wherein Q _A0 , K _A0 and L _A0 represent the same meaning as described above.), And can be produced by reacting in the same manner as described above.

The compound (III) of the present invention comprises a compound represented by the formula (A) (wherein A, X _A , Y _A , p and q represent the same meaning as described above), a compound represented by the formula (A ′) (formula In which Q _A , K _A and L _A represent the same meaning as described above.) Can be produced by reacting in the same manner as described above.

The compound (IV) of the present invention comprises a compound represented by the formula (a) (wherein A, X _a , Y _a , p and q represent the same meaning as described above), a compound represented by the formula (a ′) (formula In which Q _a , K _a and L _a have the same meaning as described above) can be produced by reacting in the same manner as described above.

Some of the compounds represented by the formula (a) are known, for example, described in the literature (EP330645), but the above-mentioned formulas (XXVI-1), (XXVI-2), (XXVI-3) and A benzaldehyde derivative represented by (XXVI-4) (hereinafter sometimes referred to as the benzaldehyde derivative of the present invention) and 6-formyl-2-[(2-methoxyethyl) aminocarbonyl] pyridine (hereinafter referred to as the pyridinecarbaldehyde of the present invention). Rudehydr derivatives (sometimes referred to as “rudehydride derivatives”) are novel substances with no examples reported so far.
The compound benzaldehyde derivative of the present invention is represented by, for example, the formula (XXVI-a)

Can be produced by reacting with a glycine methyl ester. 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 organic bases such as pyridine, triethylamine, N, N-dimethylaniline, tributylamine, and N-methylmorpholine, sodium hydroxide, potassium hydroxide. And inorganic bases such as potassium carbonate. The amount of the reagent used for the reaction is usually 1 to 2 mol for glycine methyl ester and 1 to 7 mol for base, relative to 1 mol of compound (XXVI-a). 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 extraction with an organic solvent, washing with water, and concentration of the organic layer under reduced pressure, and purification by an operation such as chromatography and recrystallization as necessary. The compound of the present invention can be obtained.
Further, the benzaldehyde derivative of the present invention has, for example, the formula (XXVI-b)

Can be produced by oxidizing with dimethyl sulfoxide activated with oxalyl chloride in the presence of a base such as triethylamine in dichloromethane (SYNTHESIS (1981), 165).
The compound represented by the formula (XXVI-b) is, for example, the formula (XXVI-c)

It can manufacture by making the compound shown by react with methoxyacetyl chloride. The reaction of compound (XXVI-c) and methoxyacetyl chloride can be carried out in the same manner as the reaction of compound (XXVI-a) and glycine methyl ester.
Further, the benzaldehyde derivative of the present invention has, for example, the formula (XXVI-d)

Can be produced by reacting with 2-methoxyethylamine. The reaction between compound (XXVI-d) and 2-methoxyethylamine can be carried out in the same manner as the reaction between compound (XXVI-a) and glycine methyl ester.
The compound (XXVI-d) is known in the literature such as J. Medicinal Chem. (2001), 44,362.
The pyridinecarbaldehyde derivative of the present invention has the formula (XXVI-e)

Can be produced by reacting with 2-methoxyethylamine. The reaction of compound (XXVI-e) and 2-methoxyethylamine can be carried out in the same manner as the reaction of compound (XXVI-a) and glycine methyl ester. Compound (XXVI-e) can be produced by reacting 2-carboxy-6-formylpyridine with a chlorinating agent such as phosphoryl chloride, thionyl chloride or phosphorus trichloride. 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 amount of the reagent used for the reaction is usually 1 to 10 mol of the chlorinating agent with respect to 1 mol of 2-carboxy-6-formylpyridine. 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. And ethers thereof or a mixture thereof. After completion of the reaction, the volatiles are distilled off under reduced pressure, whereby the compound (XXVI-e) can be obtained. 2-Carboxy-6-formylpyridine See, for example, Bioorg. Medicinal Chem. It is described in documents such as Letters (2003) 13,609, and is well known.
Among the compounds (IV) of the present invention, the cinnamoyl compounds represented by the above formulas (XLVI-1), (XLVI-2), (XLVI-3), (XLVI-4) and (XLVI-5) It can be produced by reacting the benzaldehyde derivative or the pyridinecarbaldehyde derivative of the present invention with the compound (XLVI).
[Production Method B of Compound of the Present Invention]
Among the compounds of the present invention, the cinnamoyl compound represented by the formula (XLVII ″) is obtained by reacting the cinnamoyl compound represented by the formula (XLVII) with the compound represented by the formula (XLVII ′). Can be manufactured.

Examples of the reaction method include a method of reacting compound (XLVII) and compound (XLVII ′) in the presence of a base.
The reaction of compound (XLVII) and compound (XLVII ′) in the presence of a base is usually performed in a solvent. Examples of the solvent used for the reaction include acid amides such as N, N-dimethylformamide and N, N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide, phosphate amide compounds such as hexamethylphosphoramide, acetone, And ketones such as methyl ethyl ketone.
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal carbonates such as sodium carbonate and potassium carbonate, silver oxide and the like.
Examples of the compound (XLVII ′) include alkylsulfonic acid esters such as methyl methanesulfonate, arylsulfonic acid esters such as methyl ester of p-toluenesulfonic acid, 2-methoxyethyl ester of p-toluenesulfonic acid, Sulfate esters such as dimethyl sulfate, halides such as methyl iodide, 2-chloroethyldimethylamine, allyl bromide, propargyl bromide, methyl bromoacetate, bromoacetonitrile, 2-bromoethanol, benzyl bromide, bromoacetone, etc. Can be given.
The amount of the reagent used in the reaction is usually 1 mol to 2 mol of the base and 1 mol to 2 mol of the compound (XLVII ′) with respect to 1 mol of the compound (XLVII). .
The reaction temperature is usually in the range of 0 ° C. to 100 ° C., and the reaction time is usually in the range of 1 hour to 200 hours.
After completion of the reaction, the cinnamoyl compound (XLVII ″) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound (XLVII ″) can be further purified by chromatography, recrystallization and the like.
[Production Method C of the Compound of the Present Invention]
Of the compounds of the present invention, the cinnamoyl compound represented by the formula (XLVIII ′) can be produced by hydrolyzing the cinnamoyl compound represented by the formula (XLVIII).

The hydrolysis of the cinnamoyl compound (XLVIII) is usually performed in a solvent in the presence of an acid or a base. Examples of the solvent used in the reaction include water, alcohols such as methanol and ethanol, ketones such as acetone and methyl ethyl ketone, or a mixture thereof.
Examples of the acid used for the reaction include inorganic acids such as hydrochloric acid, sulfuric acid and hydrobromic acid, and organic acids such as p-toluenesulfonic acid.
Examples of the base used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate.
The amount of the reagent used in the reaction is usually 1 mol to 10 mol with respect to 1 mol of compound (XLVIII).
The reaction temperature is usually in the range of 0 ° C. to the solvent reflux temperature, and the reaction time is usually in the range of 1 hour to 200 hours.
After completion of the reaction, the cinnamoyl compound (XLVIII ′) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound (XLVIII ′) can be further purified by chromatography, recrystallization and the like.
[Production Method D of Compound of the Present Invention]
Among the compounds of the present invention, the cinnamoyl compound represented by the formula (XLIX ″) includes the cinnamoyl compound represented by the formula (XLIX), the compound represented by the formula (XLIX ′), 1,3- It can be produced by reacting propane sultone or 1,4-butane sultone.

As the reaction method, for example, compound (XLIX) is reacted with compound (XLIX ′) in which V ′ is a leaving group, 1,3-propane sultone or 1,4-butane sultone in the presence of a base. Can be given.
The reaction between the compound (XLIX) and the compound (XLIX ′) in which V ′ is a leaving group, 1,3-propane sultone or 1,4-butane sultone in the presence of a base, The reaction between XLVII) and compound (XLVII ′) can be carried out in the same manner.
Examples of the compound (XLIX ′) in which V ′ is a leaving group include alkyl sulfonic acid esters such as 2-methoxyethyl methanesulfonic acid, and aryl sulfones such as 2-methoxyethyl ester of p-toluenesulfonic acid. Examples include acid esters, halides such as 2-chloroethyldimethylamine, allyl bromide, propargyl bromide, methyl bromoacetate, bromoacetonitrile, 2-bromoethanol, and bromoacetone.
In addition, examples of the reaction method include a method in which a compound (XLIX) and a compound (XLIX ′) in which V ′ is a hydroxyl group are subjected to a dehydration reaction in the presence of triphenylphosphine and an azodicarboxylic acid ester. Can do.
The reaction is usually carried out in a solvent, and examples of the solvent used in the reaction include ethers such as tetrahydrofuran, and examples of the azodicarboxylic acid ester include diethyl azodicarboxylate.
The amount of the reagent used in the reaction is usually 1 mol to 2 mol of triphenylphosphine and azodicarboxylic acid ester and 1 mol of compound (XLIX ′) to 1 mol of compound (XLIX). The ratio is ˜2 mol.
The reaction temperature is usually in the range of 0 ° C. to room temperature, and the reaction time is usually in the range of 1 hour to 200 hours.
After completion of the reaction, the cinnamoyl compound (XLIX ″) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound (XLIX ″) can be further purified by chromatography, recrystallization and the like.

Table 26 shows benzaldehyde derivatives (XXVI-1), (XXVI-2), (XXVI-3) and (XXVI-4) represented by compound numbers (a) to (p) and (r) to (x). And a pyridinecarbaldehyde derivative represented by the compound number (q) is shown.
Table 1

表２７〜表２９において、化合物番号（１ａ）〜（７５ａ）、（７７ａ）〜（７９ａ）及び（８１ａ）〜（８８ａ）においては、Ａはベンゼン環を表す。 Of the compounds of the present invention (IV), compounds of the present invention (IVa) represented by compound numbers (1a) to (88a) are exemplified in Tables 27 to 29.
Table 27 to Table 29
Compound (IVa) of the present invention

In Table 27 to Table 29, in compound numbers (1a) to (75a), (77a) to (79a) and (81a) to (88a), A represents a benzene ring.

Table 30 shows the present compound (IVb) represented by compound numbers (1b) to (21b) among the present compound (IV).
Table 30
Compound (IVb) of the present invention

Of the compounds of the present invention (IV), compounds of the present invention (IVc) represented by compound numbers (1c) to (3c) are exemplified in Table 31.
Table 31
Compound (IVc) of the present invention

表３２〜３４において、化合物番号（１ｄ）〜（７５ｄ）、（７７ｄ）〜（７９ｄ）及び（８１ｄ）〜（８８ｄ）においては、Ａはベンゼン環を表す。 Of the compounds of the present invention (IV), compounds of the present invention (IVd) represented by compound numbers (1d) to (88d) are exemplified in Tables 32-34.
Tables 32-34
Compound (IVd) of the present invention

In Tables 32 to 34, in compound numbers (1d) to (75d), (77d) to (79d) and (81d) to (88d), A represents a benzene ring.

Of the compounds of the present invention (IV), compounds of the present invention (IVe) represented by compound numbers (1e) to (21e) are exemplified in Table 35.
Table 35
Compound (IVe) of the present invention

The compound of the present invention has an ability to suppress transcription of type I collagen gene. This ability is important for improving tissue fibrosis by reducing the expression level of type I collagen gene and leading to a decrease in collagen accumulation. Therefore, the compound of the present invention is effective for compositions (pharmaceuticals, cosmetics, food additives, etc.) for improving tissue fibrosis by reducing the expression level of type I collagen gene and leading to a decrease in the amount of accumulated collagen. It can be used as an ingredient.
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 collagen, resulting in functional deterioration of tissues such as organs. And diseases that cause scar formation (ie, fibrosis, etc.). Specifically, for example, cirrhosis, interstitial lung disease, chronic renal failure (or disease that falls into chronic renal failure), hyperplastic scar after inflammation, postoperative scar or burn scar, scleroderma, arteriosclerosis, Diseases and abnormalities such as hypertension can be listed. 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.
Such a transcription repressing composition of the present invention or a composition for improving fibrosis of the present invention contains the compound of the present invention and an inert carrier. The compound of the present invention contained in these compositions is usually 0.01% to 99.99% by weight, and 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.

In addition, the compound of the present invention inhibits the ability of TGF-β to promote transcription of type I collagen gene, as shown in Example 4 described later. That is, the compound of the present invention is a TGF-β antagonist having the ability to suppress the action of TGF-β. Therefore, this invention compound can also be utilized as an active ingredient of a TGF- (beta) action suppression 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 the compound of the present invention and an inert carrier. The compound of the present invention contained in these compositions is usually 0.01% to 99.99% by weight, and 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.

The pharmaceutically acceptable carrier, excipient, pharmaceutical additive, food additive, cosmetic additive and the like used in the composition can be appropriately selected according to 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 compound of the present invention is used as an active ingredient of a pharmaceutical product, specific forms include, for example, powders, fine granules, granules, tablets, syrups, capsules, suspending agents, emulsions, extracts. Oral preparations such as pills and pills, injection preparations, transdermal absorption agents such as external preparations and ointments, and parenteral preparations such as suppositories and topical preparations.
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 when administered orally. 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, non-water-soluble solvents such as vegetable oil 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 compound of the present invention into a sustained release polymer pellet such as an ethylene vinyl acetate polymer. 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 compound of the present invention is added to a cosmetic and used, specific examples of the cosmetic to which the compound is added include, for example, liquid, milky, cream, lotion, ointment, gel, aerosol, mousse and the like. Can do. Lotions can be produced according to conventional methods using cosmetic additives such as suspending agents, emulsifying agents, preservatives and the like.
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. 50 mg may be administered. In addition, the above-mentioned daily dose can be administered once or divided into several times.
When the compound of the present invention is used as a food additive, specific forms of the food to which the additive is added include, for example, powders, tablets, beverages, ingestible gels or mixed liquids with syrup, for example, , Seasonings, Japanese confectionery, Western confectionery, ice confectionery, beverages, spreads, pastes, pickles, canned bottles, processed meat products, processed fish / fishery products, processed milk / eggs, processed vegetables, processed fruits, processed cereals, etc. General foods and beverages and favorite foods can be listed. 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, weight, disease level, type of composition of the present invention, dosage form, etc. of the mammal to be administered. 500 mg may be administered. In addition, the above-mentioned daily dose can be administered once or divided into several times.

  Hereinafter, the present invention will be described in more detail with reference to examples.

Example 1 Examples 1-1 to 1-24 describe the synthesis of the benzaldehyde derivative of the present invention and the pyridinecarbaldehyde derivative of the present invention.
Example 1-1 Synthesis of benzaldehyde derivative of the present invention [Compound No. (a)]
To a mixture of 12.31 g of 3-aminobenzyl alcohol, 160 ml of tetrahydrofuran and 12.41 g of triethylamine, a solution of 10.42 g of methoxyacetyl chloride in 40 ml of tetrahydrofuran was added at 10 ° C. After stirring at room temperature for 1.5 hours, insoluble matters were filtered off, the filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in 200 ml of ethyl acetate. The organic layer was washed with water, diluted hydrochloric acid and saturated brine in that order, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 15.88 g of oily 3- (methoxyacetylamino) benzyl alcohol.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 1.83 (t, 1H, J = 5.1 Hz), 3.50 (s, 3H), 4.01 (s, 2H), 4. 69 (d, 2H, J = 4.4 Hz), 7.13 (dd, 1H, J = 0.5, 7.1 Hz), 7.33 (t, 1H, J = 7.8 Hz), 7.50 (Dd, 1H, J = 1.0, 8.1 Hz), 7.59 (s, 1H), 8.26 (broad s, 1H)
To a mixture of 11.40 g of oxalyl chloride and 200 ml of dichloromethane, a solution of 14 ml of dimethyl sulfoxide in 30 ml of dichloromethane was added dropwise at −60 ° C. over 15 minutes. After stirring at −60 ° C. for 10 minutes, a solution of 15.88 g of 3- (methoxyacetylamino) benzyl alcohol in 70 ml of dichloromethane was added dropwise at −60 ° C. over 20 minutes. After stirring at −60 ° C. for 10 minutes, 24.82 g of triethylamine was added dropwise at −60 ° C. over 20 minutes. After stirring at room temperature for 45 minutes, 500 ml of water was added to the reaction solution, and the mixture was extracted with 300 ml of ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to obtain 14.93 g of 3- (methoxyacetylamino) benzaldehyde [Compound No. (a)] as white crystals.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 3.53 (s, 3H), 4.05 (s, 2H), 7.52 (t, 1H, J = 7.8 Hz), 7. 65 (d, 1H, J = 7.6 Hz), 7.93 (d, 1H, J = 8.0 Hz), 8.06 (s, 1H), 8.41 (broad s, 1H), 10.01 (S, 1H)

Example 1-2 Synthesis of benzaldehyde derivative of the present invention [Compound No. (b)] In a mixture of 200 ml of tetrahydrofuran, 26.00 g of pyridine and 20.70 g of glycine methyl ester hydrochloride, 20 ml of tetrahydrofuran of 16.00 g of 3-formylbenzoic acid chloride. The solution was added at 10 ° C. After stirring at room temperature for 6 hours, insoluble matter was filtered off, the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to give oily 3-[[[(methoxycarbonylmethyl) amino] carbonyl]. 4.23 g of benzaldehyde [Compound No. (b)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 3.83 (s, 3H), 4.29 (d, 2H, J = 4.9 Hz), 6.78 (broad s, 1H), 7 .65 (t, 1H, J = 7.6 Hz), 8.04 (d, 1H, J = 7.6 Hz), 8.11 (d, 1H, J = 7.6 Hz), 8.31 (s, 1H), 10.08 (s, 1H)

Example 1-3 Synthesis of benzaldehyde derivative of the present invention [Compound No. (c)]
4-[[((methoxycarbonylmethyl) amino] carbonyl] benzaldehyde [Compound] In the same manner as in Example 1-2 except that 15.40 g of 4-formylbenzoic acid chloride was used instead of 3-formylbenzoic acid chloride. 5.79 g of a pale yellow solid of number (c)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 3.83 (s, 3H), 4.29 (s, 2H), 6.73 (broad s, 1H), 7.97 (s, 4H) ), 10.09 (s, 1H)

Example 1-4 Synthesis of benzaldehyde derivative of the present invention [Compound No. (d)] In a mixture of 200 ml of tetrahydrofuran, 16.70 g of triethylamine and 12.40 g of 2-methoxyethylamine, a solution of 16.00 g of 3-formylbenzoic acid chloride in 20 ml of tetrahydrofuran Was added at room temperature. After stirring at room temperature for 6 hours, insoluble matter was filtered off, the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to give oily 3-[(2-methoxyethyl) aminocarbonyl] benzaldehyde. [Compound No. (d)] 10.79 g was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 3.41 (s, 3H), 3.59 (t, 2H, J = 4.6 Hz), 3.69 (dt, 2H, J = 5) .3, 5.4 Hz), 7.64 (t, 1H, J = 7.6 Hz), 8.03 (dt, 1H, J = 1.2, 7.6 Hz), 8.10 (dt, 1H, J = 1.2, 7.8 Hz), 8.27 (s, 1H), 10.08 (s, 1H)

Example 1-5 Synthesis of benzaldehyde derivative of the present invention [Compound No. (e)] A solution of 3.73 g of sodium hydride (60% oily) and 150 ml of dimethylformamide was mixed with 12 ml of a solution of 16.53 g of diethyl cyanomethylphosphonate in 12 ml of dimethylformamide. It was dripped under cooling. After stirring at room temperature for 1 hour, a solution of 14.85 g of 3-([1,3] dioxolan-2-yl) benzaldehyde in 40 ml of dimethylformamide was added. The mixture was stirred at 50 ° C. for 30 minutes, ice water 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. The obtained residue was subjected to silica gel column chromatography to obtain 11.91 g of oily 2- [3- (2-cyanoethenyl) phenyl]-[1,3] dioxolane cis-trans isomer mixture.
11.91 g of a cis-trans isomer mixture of 2- [3- (2-cyanoethenyl) phenyl]-[1,3] dioxolane was dissolved in 180 ml of tetrahydrofuran, and 40 ml of 6N hydrochloric acid was added dropwise under ice cooling. The mixture was stirred overnight at room temperature, concentrated under reduced pressure, and extracted with t-butyl methyl ether and ethyl acetate in this order. The organic layers were combined and washed sequentially with saturated aqueous sodium hydrogen carbonate and saturated brine. The crystals obtained after drying over anhydrous magnesium sulfate and concentration under reduced pressure were collected by filtration to obtain 4.90 g of trans-3- (2-cyanoethenyl) benzaldehyde [Compound No. (e)] as a white solid.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 5.96 (d, 1H, J = 16.8 Hz), 7.47 (d, 1H, J = 16.8 Hz), 7.59-7 .63 (m, 1H), 7.71 (d, 1H, J = 7.6 Hz), 7.93-7.97 (m, 2H), 10.05 (s, 1H)

Example 1-6 Synthesis of benzaldehyde derivative of the present invention [Compound No. (f)]
To a mixture of 1.00 g of 3-hydroxybenzaldehyde, 25 ml of tetrahydrofuran, 2.40 g of triphenylphosphine, and 0.78 ml of 2-methylthioethanol, 3.50 ml of diethyl azodicarboxylate (40% toluene solution) was dropped, and 15. Stir for 5 hours. The residue obtained by concentrating the reaction solution under reduced pressure was subjected to silica gel column chromatography to obtain 0.71 g of oily 3- (2-methylthioethoxy) benzaldehyde [Compound No. (f)].
¹ H-NMR (300 MHz, CDCl ₃ ) δ (ppm): 2.23 (s, 3H), 2.91 (t, 2H, J = 6.0 Hz), 4.22 (t, 2H, J = 6) .0Hz), 7.17-7.21 (m, 1H), 7.39-7.47 (m, 3H), 9.98 (s, 1H)

Example 1-7 Synthesis of benzaldehyde derivative of the present invention [Compound No. (g)]
A mixture of 1.99 g of 3- (bromomethyl) benzaldehyde, 0.80 g of sodium hydroxide and 8 ml of ethylene glycol was heated at 55 ° C. for 6 hours. Water was added and the mixture was extracted with chloroform and washed with saturated brine. The residue obtained after drying over anhydrous sodium sulfate and concentration under reduced pressure was subjected to silica gel column chromatography to obtain 0.79 g of oily 3-[(2-hydroxyethoxy) methyl] benzaldehyde [compound number (g)]. Obtained.
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 2.00 (broad s, 1H), 3.59 to 3.80 (m, 4H), 4.65 (s, 2H), 7.51 7.55 (m, 1H), 7.63 (d, 1H, J = 7.4 Hz), 7.82 (d, 1H, J = 7.4 Hz), 7.87 (s, 1H), 10 .03 (s, 1H)

Example 1-8 Synthesis of benzaldehyde derivative of the present invention [Compound No. (h)]
To a 120 ml tetrahydrofuran solution of 15.0 g 3-aminobenzyl alcohol, a 70 ml tetrahydrofuran solution containing 18 ml 2-methoxyethyl chloroformate was added dropwise under ice cooling. After stirring for 30 minutes under ice cooling and further for 30 minutes at room temperature, 2 ml of 2-methoxyethyl chloroformate was added, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate was added, washed in order with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to obtain 30.2 g of 3-[(2-methoxyethoxy) carbonylamino] benzyl alcohol. It was.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 1.82 (t, 1H, J = 5.2 Hz), 3.41 (s, 3H), 3.63 to 3.65 (m, 2H) ), 4.31-4.34 (m, 2H), 4.67 (d, 2H, J = 5.2 Hz), 6.77 (broad s, 1H), 7.05 to 7.08 (m, 1H), 7.27 to 7.31 (m, 2H), 7.40 (s, 1H)
To a mixture of 13 ml of oxalyl chloride and 400 ml of dichloromethane, a solution of 23 ml of dimethyl sulfoxide in 40 ml of dichloromethane was added dropwise at −60 ° C. over 15 minutes. After stirring at −60 ° C. for 10 minutes, a solution of 30.2 g of 3-[(2-methoxyethoxy) carbonylamino] benzyl alcohol in 100 ml of dichloromethane was added dropwise at −60 ° C. over 25 minutes. After stirring at −60 ° C. for 20 minutes, 56 ml of triethylamine was added dropwise at −60 ° C. over 15 minutes. After stirring at room temperature for 45 minutes, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in this order. The crude crystals obtained after drying over anhydrous magnesium sulfate and concentrating were washed with t-butyl methyl ether and dried to give 3-[(2-methoxyethoxy) carbonylamino] benzaldehyde [Compound No. (h)]. Of white solid was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 3.43 (s, 3H), 3.65 to 3.67 (m, 2H), 4.35 to 4.37 (m, 2H), 6.84 (broad s, 1H), 7.48 (t, 1H, J = 6.8 Hz), 7.59 (d, 1H, J = 6.8 Hz), 7.67 (d, 1H, J = 6.8 Hz), 7.90 (s, 1H), 9.99 (s, 1H)

Example 1-9 Synthesis of benzaldehyde derivative of the present invention [Compound No. (i)]
To a solution of 1.23 g of 3-aminobenzyl alcohol in 12 ml of tetrahydrofuran was added dropwise a solution of 1.32 ml of phenyl chloroformate in 5 ml of tetrahydrofuran under ice cooling. After stirring at room temperature for 30 minutes, the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in 10 ml of dimethyl sulfoxide. 2-Methoxyethylamine (2.2 ml) was added, and the mixture was stirred at 70 ° C. for 40 minutes. The mixture was cooled to room temperature, and ethyl acetate and water were added for liquid separation. Water was distilled off from the aqueous layer under reduced pressure, sodium chloride was added, and the mixture was extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, the residue obtained by concentration was subjected to silica gel column chromatography to obtain 0.67 g of oily 3-[(2-methoxyethyl) aminocarbonylamino] benzyl alcohol.
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 3.33 (s, 3H), 3.36 (t, 2H, J = 5.4 Hz), 3.45 (t, 2H, J = 5) .4 Hz), 4.53 (d, 2H, J = 5.4 Hz), 5.88 (t, 1H, J = 5.4 Hz), 6.93 (d, 1H, J = 5.4 Hz), 7 .16 (d, 1H, J = 7.6 Hz), 7.21 (s, 1H), 7.27 (d, 1H, J = 5.4 Hz), 7.64 (s, 1H), 8.00 (S, 1H)
To a mixture of 2.64 g of oxalyl chloride and 50 ml of dichloromethane, a solution of 3.24 g of dimethyl sulfoxide in 30 ml of dichloromethane was added dropwise at −60 ° C. for 10 minutes. After stirring at −60 ° C. for 20 minutes, a solution of 3.72 g of 3-[(2-methoxyethyl) aminocarbonylamino] benzyl alcohol in 30 ml of dichloromethane was added dropwise at −60 ° C. over 1 hour. After stirring at −60 ° C. for 15 minutes, 9.24 g of triethylamine was added dropwise at −60 ° C. over 25 minutes. After stirring at room temperature for 1 hour, water was added to the reaction solution to separate it. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give 2.79 g of white crystals of 3-[(2-methoxyethyl) aminocarbonylamino] benzaldehyde [Compound No. (i)]. Got.
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 3.38 (s, 3H), 3.43 to 3.48 (m, 2H), 3.53 (t, 2H, J = 4.3 Hz) ), 5.75 (broad s, 1H), 7.40 (t, 1H, J = 7.8 Hz), 7.50 (d, 1H, J = 7.6 Hz), 7.71 (d, 1H, J = 7.8 Hz), 7.80 (s, 1H), 7.81 (s, 1H), 9.92 (s, 1H)

Example 1-10 Synthesis of benzaldehyde derivative of the present invention [Compound No. (j)]
A mixture of 10.18 g of 3-formylbenzoic acid, 6.99 g of methanesulfonamide, 200 ml of dichloromethane, 8.95 g of dimethylaminopyridine, 15.22 g of dicyclohexylcarbodiimide, and 100 ml of tetrahydrofuran was stirred at room temperature. The reaction solution was concentrated under reduced pressure and dissolved in ethyl acetate, and 1N aqueous sodium hydroxide solution was added to separate the layers. The aqueous layer was adjusted to pH 1 by adding 2N hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated to give 3-[(methanesulfonyl) aminocarbonyl] benzaldehyde [Compound No. (j)]. 4.01 g of a white solid was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.38 (s, 3H), 7.75 (t, 1H, J = 7.6 Hz), 8.14-8.23 (m , 2H), 8.46 (s, 1H), 10.08 (s, 1H), 12.39 (broads, 1H)

Example 1-11 Synthesis of benzaldehyde derivative of the present invention [Compound No. (k)] To a mixture of 1.93 g of cyanoacetamide sulfate and 5 ml of water, a solution of 3.34 g of 3-formylbenzoic acid chloride in 7 ml of toluene was added dropwise under ice cooling. did. 2.93 g of sodium carbonate was added and stirred at room temperature for 2 hours. The obtained crystals were collected by filtration and washed with water, toluene and t-butyl methyl ether in this order to obtain 1.80 g of 3-[(cyanomethyl) aminocarbonyl] benzaldehyde [Compound No. (k)].
¹ H-NMR (400 MHz, CDCl ₃ + DMSO-d ₆ (1drop)) δ (ppm): 4.34 (d, 2H, J = 5.4 Hz), 7.64 to 7.67 (m, 1H), 8.03 to 8.05 (m, 1H), 8.23 to 8.26 (m, 1H), 8.46 to 8.47 (m, 1H), 9.11 (broads, 1H), 10 .09 (s, 1H)

Example 1-12 Synthesis of benzaldehyde derivative of the present invention [Compound No. (1)] A catalytic amount of iodine was added to a mixture of 0.67 g of magnesium and 10 ml of tetrahydrofuran, and 1-bromo-3- (2,2-difluoro at 55 ° C. A solution of 6.0 g of ethenyl) benzene in 20 ml of tetrahydrofuran was added dropwise. After stirring at room temperature for 15 minutes, a solution of 1.98 g of 1-formylpiperidine in 5 ml of tetrahydrofuran was added dropwise. The mixture was heated under reflux for 15 minutes, ice water and 10% hydrochloric acid were added, and the mixture was extracted with t-butyl methyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue obtained was subjected to silica gel column chromatography to give oily 3- (2,2-difluoroethenyl) benzaldehyde [ Compound No. (l)] 1.13 g was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 5.36 (dd, 1H, J = 3.4, 25.9 Hz), 7.52 (t, 1H, J = 7.6 Hz), 7 .59 (d, 1H, J = 7.8 Hz), 7.75 (d, 1H, J = 7.6 Hz), 7.83 (s, 1H), 10.01 (s, 1H)

Example 1-13 Synthesis of benzaldehyde derivative of the present invention [Compound No. (m)]
To a solution of 4.48 g of cis-trans isomer of 2- [3- (2-cyanoethenyl) phenyl]-[1,3] dioxolane was added 100% of ethyl acetate in 0.6 ml of 5% palladium on carbon and hydrogenated. The catalyst was removed by Celite filtration, and the filtrate was concentrated under reduced pressure to obtain 3.52 g of 2- [3- (2-cyanoethyl) phenyl]-[1,3] dioxolane.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.62 (t, 2H, J = 7.6 Hz), 2.98 (t, 2H, J = 7.6 Hz), 4.04-4 .13 (m, 4H), 5.80 (s, 1H), 7.24 (d, 1H, J = 7.1 Hz), 7.34 to 7.38 (m, 3H)
To 3.52 g of 2- [3- (2-cyanoethyl) phenyl]-[1,3] dioxolane was dissolved by adding 60 ml of tetrahydrofuran, and 20 ml of 6N hydrochloric acid was added. The mixture was stirred overnight at room temperature, concentrated under reduced pressure, ethyl acetate was added, and the mixture was washed in turn with an aqueous potassium carbonate solution and saturated brine. After drying over anhydrous magnesium sulfate and concentration under reduced pressure, 2.68 g of 3- (2-cyanoethyl) benzaldehyde [Compound No. (m)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.69 (t, 2H, J = 7.3 Hz), 3.06 (t, 2H, J = 7.3 Hz), 7.53-7 .56 (m, 2H), 7.76 to 7.82 (m, 2H), 10.02 (s, 1H)

Example 1-14 Synthesis of benzaldehyde derivative of the present invention [Compound No. (n)]
To a mixture of 12.21 g of 3-hydroxybenzaldehyde, 14.00 g of 2-chloroacetamide, and 60 ml of dimethylformamide, 20.70 g of potassium carbonate was added, and the mixture was heated and stirred at 90 ° C. for 2 hours. After cooling to room temperature, insolubles were filtered off, the filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran with heating. Insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The resulting crude crystals were washed with a mixed solution of tetrahydrofuran and t-butyl methyl ether and then dried to give 3- (aminocarbonylmethoxy) benzaldehyde [Compound No. 13.05 g of (n)] crystals were obtained.
¹ H-NMR (300 MHz, DMSO-d ₆ ) δ (ppm): 4.53 (s, 2H), 7.29 to 7.60 (m, 6H), 9.98 (s, 1H)

Example 1-15 Synthesis of benzaldehyde derivative of the present invention [Compound No. (o)]
To a mixture of 3.05 g of 3-hydroxybenzaldehyde, 2.3 ml of bromoacetone, and 30 ml of dimethylformamide, 4.15 g of potassium carbonate was added, and the mixture was heated and stirred at 70 ° C. for 30 minutes. After cooling to room temperature, insoluble materials were filtered off, the filtrate was concentrated under reduced pressure, water was added to the resulting residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue obtained was subjected to silica gel column chromatography to give oily 3- (2-oxo-propoxy) benzaldehyde. [Compound No. (o)] 0.76 g was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.18 (s, 3H), 4.94 (s, 2H), 7.23 to 7.30 (m, 1H), 7. 37-7.38 (m, 1H), 7.49-7.53 (m, 2H), 9.97 (s, 1H)

Example 1-16 Synthesis of benzaldehyde derivative of the present invention [Compound No. (p)] A mixture of 30 ml of tetrahydrofuran, 12 ml of triethylamine and 4.11 g of dimethyl ester aspartate was added to a solution of 3.50 g of 3-formylbenzoic acid chloride in 30 ml of tetrahydrofuran. It was dripped at 10 ° C. After stirring at room temperature for 6 hours, insoluble matters were filtered off, the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to give oily 2- [3-formyl- (benzoylamino)] succinate. 3.01 g of acid dimethyl ester [Compound No. (p)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.82 to 3.03 (m, 2H), 3.39 (s, 3H), 3.44 (s, 3H), 4. 84 to 4.92 (m, 1H), 7.68 to 7.95 (m, 1H), 8.12 to 8.18 (m, 2H), 8.39 (s, 1H), 9.18 ( d, 1H, J = 8.1 Hz), 10.09 (s, 1H)

Example 1-17 Synthesis of the present pyridinecarbaldehyde derivative [Compound No. (q)]
A mixture of 5.15 g of 2-carboxy-6-formylpyridine and 50 ml of thionyl chloride was stirred under reflux for 1 hour and then concentrated under reduced pressure. The obtained acid chloride was dissolved in 30 ml of tetrahydrofuran and added dropwise to a mixture of 30 ml of tetrahydrofuran, 3.12 g of triethylamine and 2.31 g of 2-methoxyethylamine under ice cooling. The mixture was allowed to stand overnight at room temperature and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 6-formyl-2-[(2-methoxyethyl) aminocarbonyl] pyridine [Compound No. (q)]. 3.28 g of a white solid was obtained.
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 3.43 (s, 3H), 3.56 to 3.65 (m, 2H), 3.70 to 3.76 (m, 2H), 8.02 to 8.12 (m, 2H), 8.34 (broad s, 1H), 8.43 to 8.46 (m, 1H), 10.11 (s, 1H)

Example 1-18 Synthesis of benzaldehyde derivative of the present invention [Compound No. (r)]
To a 200 ml tetrahydrofuran solution of 4.0 g of 3-[(2-methoxyethyl) aminosulfonyl] benzoic acid, 43.5 ml of a 1.07 M borane-tetrahydrofuran complex tetrahydrofuran solution was added dropwise under ice-cooling and stirred for 30 minutes. And stirred overnight. Under ice-cooling, 40 ml of methanol was added dropwise, and then 100 ml of 2N hydrochloric acid was added dropwise. After warming to room temperature, the solvent was distilled off under reduced pressure and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 3.0 g of oily 3-[(2-methoxyethyl) aminosulfonyl] benzyl alcohol.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.86 to 2.92 (m, 2H), 3.16 (s, 3H), 3.27 to 3.33 (m, 2H) ), 4.58 (d, 2H, J = 5.6 Hz), 5.42 (t, 1H, J = 5.6 Hz), 7.50-7.78 (m, 5H)
To a mixture of 1.71 g of oxalyl chloride and 30 ml of dichloromethane, a solution of 2.3 g of dimethyl sulfoxide in 4 ml of dichloromethane was added dropwise at −60 ° C. over 35 minutes. After stirring at −60 ° C. for 20 minutes, a solution of 3.0 g of 3-[(2-methoxyethyl) aminosulfonyl] benzyl alcohol in 22 ml of dichloromethane was added dropwise at −60 ° C. over 1.5 hours. After stirring at −60 ° C. for 1 hour, 5.1 ml of triethylamine was added dropwise at −60 ° C. over 25 minutes. After stirring at room temperature for 3 hours, water was added to the reaction solution for liquid separation. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue obtained was subjected to silica gel column chromatography to give oily 3-[(2-methoxyethyl) aminosulfonyl] benzaldehyde [Compound No. (R)] 2.07 g was obtained.
¹ H-NMR (300 MHz, CDCl ₃ ) δ (ppm): 3.15 to 3.20 (m, 2H), 3.28 (s, 3H), 3.41 to 3.44 (m, 2H), 5.00 (t, 1H, J = 6.0 Hz), 7.72 (t, 1H, J = 7.5 Hz), 8.09 to 8.15 (m, 2H), 8.37 (s, 1H ), 10.09 (s, 1H)

Example 1-19 Synthesis of benzaldehyde derivative of the present invention [Compound No. (s)]
To a solution of 5.63 g of 3-([1,3] dioxolan-2-yl) benzoic acid in 60 ml of tetrahydrofuran was added 3.3 ml of ethyl chloroformate and 4.8 ml of triethylamine under ice cooling. After stirring for 10 minutes under ice cooling, the insoluble material was filtered off. This solution was added dropwise to a mixture of 3.63 g of methoxyamine hydrochloride, 20 ml of tetrahydrofuran, 6 ml of triethylamine, and 20 ml of dimethylformamide. After stirring at room temperature for 8 hours, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in 30 ml of tetrahydrofuran, 15 ml of 2N hydrochloric acid was added dropwise, and the mixture was stirred at room temperature for 8 hours. 20 ml of 2N aqueous sodium hydroxide solution was added dropwise under ice cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.50 g of 3- (methoxyaminocarbonyl) benzaldehyde [Compound No. (s)] as a white solid.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.73 (s, 3H), 7.72 (t, 1H, J = 7.7 Hz), 8.05 to 8.10 (m , 2H), 8.28 (s, 1H), 10.07 (s, 1H), 11.98 (broads, 1H)

Example 1-20 Synthesis of benzaldehyde derivative of the present invention [Compound No. (t)] In the same manner as in Example 1-19 except that 4.93 g of allyloxyamine hydrochloride was used instead of methoxyamine hydrochloride, 3- A white solid of 1.55 g of (allyloxyaminocarbonyl) benzaldehyde [Compound No. (t)] was obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 4.44 (d, 2H, J = 5.9 Hz), 5.26 to 5.40 (m, 2H), 5.94 to 6 .09 (m, 1H), 7.72 (t, 1H, J = 7.7 Hz), 8.04 to 8.10 (m, 2H), 8.27 (s, 1H), 10.07 (s , 1H), 11.90 (broad s, 1H)

Example 1-21 Synthesis of benzaldehyde derivative of the present invention [Compound No. (u)]
To a mixture of 1.00 g of 3- (bromomethyl) benzaldehyde and 20 ml of ethanol, 0.65 ml of methyl thioglycolate and 0.47 g of potassium carbonate were added and stirred at room temperature for 2.5 hours. Diethyl ether was added to the reaction mixture, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography to give oily 3-[(methoxycarbonylmethylthio ) Methyl] benzaldehyde [Compound No. (u)] 0.36 g was obtained.
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 3.08 (s, 2H), 3.73 (s, 3H), 3.91 (s, 2H), 7.51 (dd, 1H, J = 7.6 Hz), 7.64 (d, 1H, J = 7.6 Hz), 7.78-7.81 (m, 1H), 7.86 (s, 1H), 10.02 (s, 1H)

Example 1-22 Synthesis of benzaldehyde derivative of the present invention [Compound No. (v)]
To a suspension of 4.58 g of 3- (cyanobenzyl) triphenylphosphonium bromide in 15 ml of tetrahydrofuran was added 0.73 g of sodium hydride (60% oily) under ice cooling, and the mixture was stirred at room temperature for 1 hour. To this, 1.01 g of tetrahydro-4H-pyran-4-one was added and stirred at room temperature for 1 hour, and 2 ml of dimethylformamide was added and further stirred at room temperature for 5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to obtain 0.20 g of yellow oily 3-[(tetrahydropyran-4-ylidene) methyl] benzonitrile. Obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 2.35 (t, 2H, J = 5.4 Hz), 2.43 (t, 2H, J = 5.4 Hz), 3.58 (T, 2H, J = 5.4 Hz), 3.68 (t, 2H, J = 5.4 Hz), 6.36 (s, 1H), 7.51 to 7.56 (m, 2H), 7 .66-7.70 (m, 2H)
To a solution of 0.20 g of 3-[(tetrahydropyran-4-ylidene) methyl] benzonitrile in 7 ml of toluene, 1.24 ml of a 1.5 M toluene solution of diisobutylaluminum hydride was added dropwise at room temperature. After stirring at room temperature for 7 hours, an aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to give 3-[(tetrahydropyran-4-ylidene) methyl] benzaldehyde [compound number (v ] 0.06 g was obtained.
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 2.43 (t, 2H, J = 5.4 Hz), 2.52 (t, 2H, J = 5.4 Hz), 3.68 (t , 2H, J = 5.4 Hz), 3.80 (t, 2H, J = 5.4 Hz), 6.37 (s, 1H), 7.44 to 7.53 (m, 2H), 7.71 ˜7.75 (m, 2H), 10.01 (s, 1H)

Example 1-23 Synthesis of benzaldehyde derivative of the present invention [Compound No. (w)]
To a solution of 4.93 g of m-aminobenzyl alcohol in 50 ml of tetrahydrofuran was added dropwise a solution of 3.7 ml of chloroglyoxylic acid methyl ester in 20 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate and washed with saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the resulting residue was subjected to silica gel column chromatography to obtain 5.10 g of 3-[(methoxycarbonyl) carbonylamino] benzyl alcohol as a white solid.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.85 (s, 3H), 4.47 (d, 2H, J = 5.7 Hz), 5.23 (t, 1H, J = 5.7 Hz), 7.09 (d, 1 H, J = 7.6 Hz), 7.30 (t, 1 H, J = 7.8 Hz), 7.58 (d, 1 H, J = 8.1 Hz) , 7.73 (s, 1H), 10.76 (s, 1H)
3.47 g of manganese dioxide was added to a solution of 1.69 g of 3-[(methoxycarbonyl) carbonylamino] benzyl alcohol in 20 ml of acetone and stirred at room temperature for 2 hours. Then, 3.92 g of manganese dioxide was further added and stirred at room temperature for 18 hours. did. The reaction solution was filtered through Celite, and the residue obtained by concentrating the filtrate under reduced pressure was subjected to silica gel column chromatography, whereby 3-[(methoxycarbonyl) carbonylamino] benzaldehyde [Compound No. (w)] was obtained as a white solid. 53 g were obtained.
¹ H-NMR (270 MHz, DMSO-d ₆ ) δ (ppm): 3.87 (s, 3H), 7.61 (t, 1H, J = 7.6 Hz), 7.72 (d, 1H, J = 7.8 Hz), 8.00 (d, 1 H, J = 8.1 Hz), 8.34 (s, 1 H), 9.99 (s, 1 H), 11.08 (s, 1 H)

Example 1-24 Synthesis of benzaldehyde derivative of the present invention [Compound No. (x)]
A mixture of 0.60 g of 3- (bromomethyl) benzaldehyde and 0.45 ml of trimethyl phosphite was stirred at 100 ° C. for 3 hours. The reaction mixture was subjected to silica gel column chromatography to obtain 0.62 g of oily dimethyl (3-formylbenzyl) phosphonate [Compound No. (x)].
¹ H-NMR (270 MHz, CDCl ₃ ) δ (ppm): 3.24 (d, 2H, J = 21.9 Hz), 3.70 (d, 6H, J = 11.1 Hz), 7.48-7 .61 (m, 2H), 7.78 to 7.81 (m, 2H), 10.02 (s, 1H)

Example a-1 Synthesis of Compound of the Present Invention [Compound No. (1a)] by Production Method A 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 5.24 g, 3- ( 3.90 g of 3-formylphenyl) -2-propenenitrile and 1.92 g of piperidine were dissolved, and heated under reflux for 35 minutes while removing water with a Soxhlet extractor filled with molecular sieves. After cooling to room temperature, the reaction mixture was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The precipitated crystals were collected by filtration and subjected to silica gel column chromatography to give 4-hydroxy-3- [3- [3- (2-cyanoethenyl) phenyl] -1-oxo-2-propenyl] -6- 4.05 g of pale yellow crystals of methyl-2H-pyran-2-one [Compound No. (1a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.30 (s, 3H), 5.94 (d, 1H, J = 16.8 Hz), 5.98 (s, 1H), 7. 43 (d, 1H, J = 16.8 Hz), 7.45-7.50 (2H), 7.70 (s, 1H), 7.75 (d, 1H, J = 6.8 Hz), 7. 92 (d, 1H, J = 16.0 Hz), 8.33 (d, 1H, J = 15.6 Hz), 12.38 (s, 1H)

Example a-2 Synthesis of Compound of the Present Invention [Compound No. (2a)] by Production Method B 20 ml of hexamethylphosphoramide and 4-hydroxy-3- [3- [3- (2-cyanoethenyl) phenyl] -1-oxo -2-propenyl] -6-methyl-2H-pyran-2-one To a mixture of 3.50 g, 0.46 g of sodium hydride (60% oily) was added at about 0 ° C., and the temperature was raised to 50 ° C. Stir for 10 minutes. Next, 3.22 g of dimethyl sulfate was added, and the mixture was stirred at 50 ° C. for 4 hours. The reaction mixture was then poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give 4-methoxy-3- [3- [3- (2-cyanoethenyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2- 1.12 g of pale yellow crystals of ON [Compound No. (2a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.36 (s, 3H), 3.96 (s, 3H), 5.92 (d, 1H, J = 16.9 Hz), 6. 15 (s, 1H), 7.20 (d, 1H, J = 15.9 Hz), 7.39 (d, 1H, J = 16.6 Hz), 7.41 (d, 1H, J = 7.6 Hz) ), 7.45 (d, 1H, J = 8.8 Hz), 7.60 (d, 1H, J = 15.9 Hz), 7.55 to 7.70 (2H)

Example a-3 Synthesis of Compound of the Present Invention [Compound No. (4a)] by Production Method A
4-Hydroxy-3- [3- (3- (3- (3-formylphenyl) -2-propenenitrile was prepared in the same manner as in Example a-1, except that 23.8 g of 3-allyloxybenzaldehyde was used. 7.30 g of yellow crystals of 3-allyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (4a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₆ ) δ (ppm): 2.28 (s, 3H), 4.58 to 4.62 (2H), 5.30 (d, 1H), 5.48 (d, 1H), 5.96 (s, 1H), 6.00 to 6.13 (m, 1H), 6.96 to 7.02 (m, 1H), 7.25 to 7.40 (m, 3H) 7.91 (d, 1H, J = 15.6 Hz), 8.28 (d, 1H, J = 15.6 Hz), 12.12 (s, 1H)

Example a-4 Synthesis of the present compound [Compound No. (5a)] 4-Hydroxy-3- [3- (3-allyloxyphenyl) -1-oxo-2-propenyl] -6-methyl- in 20 ml of tetrahydrofuran 2.00 g of 2H-pyran-2-one, 1.85 g of triphenylphosphine and 0.23 g of methanol were added, and a solution of 1.23 g of diethyl azodicarboxylate in 12 ml of tetrahydrofuran was added dropwise to the mixture. The mixture was stirred at room temperature for 18 hours, and the reaction solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 4-methoxy-3- [3- (3-allyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [compound 0.12 g of a yellow oil of number (5a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₆ ) δ (ppm): 2.35 (s, 3H), 3.95 (s, 3H), 4.55 to 4.60 (2H), 5.30 (d, 1H), 5.45 (d, 1H), 6.00 to 6.15 (m, 1H), 6.12 (s, 1H), 6.90 to 7.00 (1H), 7.10 to 7 .20 (2H), 7.45 to 7.80 (3H)

Example a-5 Synthesis of Compound of the Present Invention [Compound No. (7a)] by Production Method A
4-hydroxy-3- [3- (3- (3- (3-formylphenyl) -2-propenenitrile was prepared in the same manner as in Example a-1, except that 20.00 g of 3-propargyloxybenzaldehyde was used. There were obtained 1.05 g of pale yellow crystals of 3-propargyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (7a)].
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.32 (s, 3H), 2.56 (s, 1H), 4.74 (s, 2H), 5.97 (s, 1H) , 7.00 to 7.10 (1H), 7.30 to 7.40 (3H), 7.92 (d, 1H, J = 15.6 Hz), 8.29 (d, 1H, J = 15. 6Hz), 12.16 (s, 1H)

Example a-6 Synthesis of compound of the present invention [Compound No. (8a)]
Instead of 4-hydroxy-3- [3- (3-allyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one, 4-hydroxy-3- [3- In the same manner as in Example a-4 except that 30.80 g of (3-propargyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one was used, 4-methoxy- 0.48 g of yellow solid of 3- [3- (3-propargyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (8a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.35 (s, 3H), 2.53 (s, 1H), 3.93 (s, 3H), 4.71 (s, 2H) , 6.12 (s, 1H), 6.95-7.40 (3H), 7.40-7.70 (3H)

Example a-7 Synthesis of Compound of the Present Invention [Compound No. (9a)] by Production Method A
4-hydroxy-3- [3- (3- (3- (3-formylphenyl) -2-propenenitrile was prepared in the same manner as in Example a-1, except that 10.00 g of 4-propargyloxybenzaldehyde was used. 0.89 g of red crystals of 4-propargyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (9a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.27 (s, 3H), 2.57 (s, 1H), 4.78 (s, 2H), 5.95 (s, 1H) 7.01 (d, 2H, J = 6.8 Hz), 7.68-7.70 (d, 2H), 7.94 (d, 1H, J = 15.6 Hz), 8.21 (d, 1H, J = 15.6 Hz), 11.90 (s, 1H)

Example a-8 Synthesis of Compound of the Present Invention [Compound No. (10a)]
Instead of 4-hydroxy-3- [3- (3-allyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one, 4-hydroxy-3- [3- In the same manner as in Example a-4 except that 0.84-g of (4-propargyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one was used, 4-methoxy- 0.28 g of 3- [3- (4-propargyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (10a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.34 (s, 3H), 2.54 (s, 1H), 3.92 (s, 3H), 4.73 (s, 2H) , 6.11 (s, 1H), 6.97 (d, 2H, J = 6.8 Hz), 7.01 (d, 1H, J = 15.9 Hz), 7.53 (d, 2H, J = 6.8 Hz), 7.56 (d, 1H, J = 15.9 Hz)

Example a-9 Synthesis of Compound of the Present Invention [Compound No. (14a)] by Production Method A
4-Hydroxy-3- [3 in the same manner as in Example a-1, except that 0.45 g of 3- (cyanomethoxy) benzaldehyde was used instead of 3- (3-formylphenyl) -2-propenenitrile. 0.10 g of yellow crystals of-[3- (cyanomethoxy) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (14a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.30 (s, 3H), 4.83 (s, 2H), 5.98 (s, 1H), 7.04 to 7.08 ( 1H), 7.25-7.26 (1H), 7.38-7.46 (1H), 7.90 (d, 1H, J = 15.6 Hz), 8.30 (d, 1H, J = 15.6Hz), 12.27 (s, 1H)

Example a-10 Synthesis of Compound of the Present Invention [Compound No. (15a)] by Production Method B
Instead of 4-hydroxy-3- [3- [3- (2-cyanoethenyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one, 4-hydroxy-3- [3- [3- (Cyanomethoxy) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one The same as Example a-2 except that 89.0 mg was used. , 4-methoxy-3- [3- [3- (cyanomethoxy) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (15a)] 13.6 mg Got.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.36 (s, 3H), 3.95 (s, 3H), 4.79 (s, 2H), 6.13 (s, 1H) , 7.00 (dd, 1H, J = 2.4, 8.1 Hz), 7.13 (d, 1H, J = 15.9 Hz), 7.15 (s, 1H), 7.30 (d, 1H, J = 7.6 Hz), 7.36 (t, 1H, J = 7.8 Hz), 7.57 (d, 1H, J = 15.9 Hz)

Example a-11 Synthesis of Compound of the Present Invention [Compound No. (21a)] by Production Method A
In the same manner as in Example a-1, except that 0.19 g of 3- (methoxyacetylamino) benzaldehyde was used instead of 3- (3-formylphenyl) -2-propenenitrile, 4-hydroxy-3- [ 0.15 g of yellow crystals of 3- [3- (methoxyacetylamino) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (21a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.29 (s, 3H), 3.53 (s, 3H), 4.03 (s, 2H), 5.96 (s, 1H) , 7.39 (t, 1H, J = 8.0 Hz), 7.45 (d, 1H, J = 8.1 Hz), 7.71 (s, 1H), 7.84 (d, 1H, J = 8.1 Hz), 7.92 (d, 1 H, J = 15.9 Hz), 8.28 (d, 1 H, J = 15.9 Hz), 8.33 (s, 1 H), 12.20 (s, 1H)

Example a-12 Synthesis of compound of the present invention [Compound No. (22a)]
Instead of 4-hydroxy-3- [3- (3-allyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one, 4-hydroxy-3- [3- Example 3-4, except that 0.80 g of [3- (methoxyacetylamino) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one was used 0.63 g of 2-methoxy-3- [3- [3- (methoxyacetylamino) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (22a)] Obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.35 (s, 3H), 3.52 (s, 3H), 3.94 (s, 3H), 4.02 (s, 2H) , 6.12 (s, 1H), 7.11 (d, 1H, J = 16.1 Hz), 7.33 to 7.37 (2H), 7.57 (d, 1H, J = 16.1 Hz) , 7.59-7.65 (1H), 7.77 (s, 1H), 8.29 (s, 1H)

Example a-13 Synthesis of Compound of the Present Invention [Compound No. (24a)] by Production Method A
In the same manner as in Example a-1, except that 2.23 g of 3-[(2-methoxyethoxy) carbonylamino] benzaldehyde was used instead of 3- (3-formylphenyl) -2-propenenitrile, 4- Hydroxy-3- [3- [3-[(2-methoxyethoxy) carbonylamino] phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (24a)] Of yellow crystals were obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.28 (s, 3H), 3.40 (s, 3H), 3.65 (d, 2H, J = 4.8 Hz), 4. 33 (d, 2H, J = 4.4 Hz), 5.97 (s, 1H), 7.31 to 7.35 (1H), 7.37 (t, 1H, J = 7.6 Hz), 7. 60 (d, 1H, J = 7.2 Hz), 7.72 (s, 1H), 7.92 (d, 1H, J = 16.0 Hz), 8.26 (d, 1H, J = 16.0 Hz) ), 8.27 (s, 1H), 12.15 (s, 1H)

Example a-14 Synthesis of Compound of the Present Invention [Compound No. (25a)] by Production Method B
Instead of 4-hydroxy-3- [3- [3- (2-cyanoethenyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one, 4-hydroxy-3- Example a except that 1.00 g of [3- [3-[(2-methoxyethoxy) carbonylamino] phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one was used 4-methoxy-3- [3- [3-[(2-methoxyethoxy) carbonylamino] phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2 0.44 g of on-compound [compound number (25a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.35 (s, 3H), 3.42 (s, 3H), 3.65 (t, 2H, J = 4.8 Hz), 3. 93 (s, 3H), 4.33 (t, 2H, J = 4.4 Hz), 6.11 (s, 1H), 6.74 (s, 1H), 7.08 (d, 1H, J = 16.0 Hz), 7.25 to 7.38 (4H), 7.54 (d, 1H, J = 16.4 Hz), 7.61 (s, 1H)

Example a-15 Synthesis of Compound of the Present Invention [Compound No. (33a)] by Production Method A
In the same manner as in Example a-1, except that 1.50 g of 3-[[(methoxycarbonylmethyl) amino] carbonyl] benzaldehyde was used instead of 3- (3-formylphenyl) -2-propenenitrile, 4 -Hydroxy-3- [3- [3-[[(methoxycarbonylmethyl) amino] carbonyl] phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (33a )] Yellow crystals of 0.68 g were obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.30 (s, 3H), 3.82 (s, 3H), 4.29 (s, 2H), 5.98 (s, 1H) 6.71 (broad s, 1H), 7.52 (t, 1H, J = 7.6 Hz), 7.86 (d, 2H, J = 7.6 Hz), 7.96 (d, 1H, J = 15.6 Hz), 8.04 (s, 1 H), 8.34 (d, 1 H, J = 16.0 Hz)

Example a-16 Synthesis of Compound of the present invention [Compound No. (36a)] by Production Method A
In the same manner as in Example a-1, except that 1.00 g of 4-[(2-methoxyethyl) aminocarbonyl] benzaldehyde was used instead of 3- (3-formylphenyl) -2-propenenitrile, 4- Hydroxy-3- [3- [4-[(2-methoxyethyl) aminocarbonyl] phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (36a)] Of yellow crystals were obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.30 (s, 3H), 3.40 (s, 3H), 3.58 (t, 1H, J = 4.8 Hz), 3. 65 to 3.75 (m, 2H), 5.98 (s, 1H), 6.55 (s, 1H), 7.74 (d, 2H, J = 8.4 Hz), 7.82 (d, 2H, J = 8.4 Hz), 7.94 (d, 1H, J = 15.6 Hz), 8.36 (d, 1H, J = 15.6 Hz)

Example a-17 Synthesis of Compound of the Present Invention [Compound No. (42a)] by Production Method A
In the same manner as in Example a-1, except that 1.13 g of 3- (2,2-difluoroethenyl) benzaldehyde was used instead of 3- (3-formylphenyl) -2-propenenitrile, 4-hydroxy -3- [3- [3- (2,2-Difluoroethenyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (42a)] 0.61 g of crystals was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.29 (s, 3H), 5.33 (dd, 1H, J = 3.7, 25.9 Hz), 5.97 (s, 1H) ), 7.39-7.41 (m, 2H), 7.57-7.58 (m, 2H), 7.92 (d, 1H, J = 15.9 Hz), 8.30 (d, 1H) , J = 15.9 Hz)

Example a-18 Synthesis of Compound of the Present Invention [Compound No. (43a)] by Production Method B
Instead of 4-hydroxy-3- [3- [3- (2-cyanoethenyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one, 4-hydroxy-3- Example a-2 except that 538 mg of [3- [3- (2,2-difluoroethenyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one was used Similarly, 4-methoxy-3- [3- [3- (2,2-difluoroethenyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [compound No. (43a)] 113 mg of yellow crystals was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.35 (s, 3H), 3.94 (s, 3H), 5.28 (dd, 1H, J = 3.6, 25.9 Hz) ), 6.13 (s, 1H), 7.13 (d, 1H, J = 15.9 Hz), 7.33-7.37 (2H), 7.43-7.47 (1H), 7. 50 (s, 1H), 7.58 (d, 1H, J = 15.9 Hz)

Example a-19 Synthesis of Compound of the Present Invention [Compound No. (44a)] by Production Method A
In the same manner as in Example a-1 except that 2.68 g of 3- (2-cyanoethyl) benzaldehyde was used instead of 3- (3-formylphenyl) -2-propenenitrile, 4-hydroxy-3- [ 0.74 g of yellow crystals of 3- [3- (2-cyanoethyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (44a)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.30 (s, 3H), 2.67 (t, 2H, J = 7.3 Hz), 3.01 (t, 2H, J = 7 .3 Hz), 5.98 (s, 1 H), 7.32 (d, 1 H, J = 7.7 Hz), 7.41 (t, 1 H, J = 7.7 Hz), 7.53 (s, 1 H) ), 7.61 (d, 1H, J = 17.7 Hz), 7.94 (d, 1H, J = 15.8 Hz), 8.31 (d, 1H, J = 15.8 Hz)

Example a-20 Synthesis of the compound of the present invention [Compound No. (45a)] by Production Method B
Instead of 4-hydroxy-3- [3- [3- (2-cyanoethenyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one, 4-hydroxy-3- [3- [3- (2-cyanoethyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one The same as Example a-2 except that 0.61 g was used. 4-methoxy-3- [3- [3- (2-cyanoethyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (45a)] 0.30 g of a light brown oil was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.35 (s, 3H), 2.64 (t, 2H, J = 7.5 Hz), 2.97 (t, 2H, J = 7) .5 Hz), 3.94 (s, 3 H), 6.14 (s, 1 H), 7.14 (d, 1 H, J = 16.2 Hz), 7.23 to 7.27 (m, 1 H), 7.33-7.40 (m, 1H), 7.42 (s, 1H), 7.47-7.49 (m, 1H), 7.59 (d, 1H, J = 16.2 Hz)

Example a-21 Synthesis of Compound of the Present Invention [Compound No. (49a)] by Production Method A
In the same manner as in Example a-1 except that 0.50 g of 3- (3-hydroxypropoxy) benzaldehyde was used instead of 3- (3-formylphenyl) -2-propenenitrile, 4-hydroxy-3- There were obtained 95 mg of yellow crystals of [3- [3- (3-hydroxypropoxy) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (49a)].
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 1.68 (t, 1H, J = 5.3 Hz), 2.06 to 2.11 (m, 2H), 2.29 (s, 3H ), 3.87-3.91 (m, 2H), 4.19 (t, 2H, J = 6.0 Hz), 5.97 (s, 1H), 6.98-6.99 (m, 1H) ), 7.23 to 7.35 (m, 3H), 7.92 (d, 1H, J = 15.9 Hz), 8.29 (d, 1H, J = 15.9 Hz)

Example b-1 Synthesis of Compound of the Present Invention [Compound No. (1b)] by Production Method B 4-allyloxy-3-methylate in the same manner as in Example a-4 except that 224 μl of allyl alcohol was used instead of methanol. 69.7 mg of [3- (3-allyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (1b)] was obtained.
¹ H-NMR (400 MHz, CDCl ₆ ) δ (ppm): 2.33 (s, 3H), 4.50 to 4.58 (2H), 4.65 to 4.70 (2H), 5.25 5.35 (2H), 5.35 to 5.45 (2H), 5.85 to 6.00 (1H), 6.00 to 6.10 (1H), 6.07 (s, 1H), 6 .90 to 6.95 (1H), 7.05 to 7.20 (1H), 7.20 to 7.30 (1H), 7.45 to 7.50 (1H), 7.50 to 7.60 (1H), 7.70-7.80 (1H)

Example b-2 Synthesis of Compound of the Present Invention [Compound No. (2b)] by Production Method B
Instead of 4-hydroxy-3- [3- (3-allyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one, 4-hydroxy-3- [3- In the same manner as in Example b-1, except that (3-propargyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one was used, 4-allyloxy- 0.25 g of 3- [3- (3-propargyloxyphenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (2b)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.33 (s, 3H), 2.54 (s, 1H), 4.69 (2H), 4.72 (2H), 5.38 (D, 1H), 5.44 (d, 1H), 5.85 to 5.95 (1H), 6.07 (s, 1H), 6.98 to 7.02 (1H), 7.05 7.25 (1H), 7.25 to 7.35 (1H), 7.56 (d, 1H, J = 16.1 Hz)

Example b-3 Synthesis of Compound of the Present Invention [Compound No. (14b)] 85.7 mg of 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one, 3- (2-methylthioethoxy) in 8 ml of chloroform ) 100 mg of benzaldehyde and 30.3 mg of piperidine were dissolved, and the mixture was heated under reflux for 13 hours while removing water with a Soxhlet extractor filled with molecular sieves. After cooling to room temperature, the reaction mixture was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The precipitated crystals were collected by filtration and subjected to silica gel column chromatography to give 4-piperidino-3- [3- [3- (2-methylthioethoxy) phenyl] -1-oxo-2-propenyl] -6 10.1 mg of pale yellow crystals of -methyl-2H-pyran-2-one [Compound No. (14b)] was obtained.
¹ H-NMR (400 MHz, CDCl ₆ ) δ (ppm): 1.75 to 2.00 (6H), 2.19 (s, 3H), 2.23 (s, 3H), 2.89 (t, 2H, J = 6.8 Hz), 3.75 to 4.00 (4H), 4.17 (t, 2H, J = 6.8 Hz), 5.69 (s, 1H), 6.90-7. 35 (5H), 7.36 (d, 1H, J = 15.4 Hz)

Example b-4 Synthesis of the present compound [Compound No. (15b)]
4-piperidino-3- [3- (2-propargyloxy) was prepared in the same manner as in Example b-3, except that 0.40 g of 2-propargyloxybenzaldehyde was used instead of 3- (2-methylthioethoxy) benzaldehyde. 0.23 g of yellow crystals of (phenyl) -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (15b)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 1.75 to 2.00 (6H), 2.13 (s, 3H), 2.53 (t, 1H, J = 2.2 Hz), 3.70 to 4.00 (4H), 4.73 (d, 2H, J = 2.4 Hz), 5.68 (s, 1H), 6.98 (d, 1H, J = 8.3 Hz), 7.00 (t, 1H, J = 7.6 Hz), 7.24 (d, 1H, J = 16.4 Hz), 7.35 (dt, 1H, J = 1.4, 7.8 Hz), 7 .52 (dd, 1H, J = 1.5, 7.6 Hz), 7.59 (d, 1H, J = 15.6 Hz)

Example b-5 Synthesis of the compound of the present invention [Compound No. (16b)]
4-piperidino-3 was prepared in the same manner as in Example b-3 except that 0.30 g of 3-[[(methoxycarbonylmethyl) amino] carbonyl] benzaldehyde was used instead of 3- (2-methylthioethoxy) benzaldehyde. -[3- [3-[[(Methoxycarbonylmethyl) amino] carbonyl] phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (16b)] yellow 0.21 g of crystals was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 1.75 to 1.95 (6H), 2.15 (s, 3H), 3.70 to 4.00 (4H), 3.81 ( s, 3H), 4.26 (s, 2H), 5.69 (s, 1H), 7.05 (t, 1H, J = 5.2 Hz), 7.18 (d, 1H, J = 15. 7 Hz), 7.36 (t, 1 H, J = 7.8 Hz), 7.45 (d, 1 H, J = 15.9 Hz), 7.59 (d, 1 H, J = 7.8 Hz), 7. 75 (d, 1H, J = 7.8 Hz), 8.02 (s, 1H)

Example b-6 Synthesis of the compound of the present invention [Compound No. (19b)]
Other than using 0.81 g of 3-[[(methoxycarbonylmethyl) amino] carbonyl] benzaldehyde in place of 3- (3-formylphenyl) -2-propenenitrile and 223 μl of morpholine in place of piperidine Is analogous to Example b-3 in 4-morpholino-3- [3- [3-[[(methoxycarbonylmethyl) amino] carbonyl] phenyl] -1-oxo-2-propenyl] -6-methyl- 0.26 g of yellow crystals of 2H-pyran-2-one [Compound No. (19b)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 2.17 (s, 3H), 3.79 (s, 3H), 3.90 to 4.10 (8H), 4.26 (d, 2H, J = 4.9 Hz), 5.71 (s, 1H), 7.08 (t, 1H, J = 5.4 Hz), 7.23 (d, 1H, J = 15.6 Hz), 7. 36 (t, 1H, J = 7.8 Hz), 7.53 (d, 1H, J = 15.4 Hz), 7.59 (d, 1H, J = 7.8 Hz), 7.76 (d, 1H) , J = 7.8 Hz), 8.05 (s, 1H)

Example b-7 Synthesis of the compound of the present invention [Compound No. (20b)]
Propargyl in a mixture of 0.20 g 4-methoxy-3- [3- [3- (2-cyanoethenyl) phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one and 10 ml benzene 34.3 mg of amine was added and heated under reflux for 3 hours and 45 minutes. After cooling to room temperature, the precipitated crystals were collected by filtration to give 4-propargylamino-3- [3- [3- (2-cyanoethenyl) phenyl] -1-oxo-2-propenyl] -6-methyl- 68.0 mg of light brown powder of 2H-pyran-2-one [Compound No. (20b)] was obtained.
¹ H-NMR (400 MHz, DMSO-d ₆ ) δ (ppm): 2.25 (s, 3H), 3.41 (s, 1H), 4.35 (d, 2H, J = 3.2 Hz), 6.40 (s, 1H), 6.56 (d, 1H, J = 16.4 Hz), 7.51 (t, 1H, J = 8.0 Hz), 7.52 (d, 1H, J = 15) .6 Hz), 7.71 (d, 1H, J = 16.8 Hz), 7.65 to 7.76 (2H), 7.91 (s, 1H), 8.06 (d, 1H, J = 15) .6 Hz), 11.41 (s, 1H)

Example d-1 Synthesis of Compound of the Present Invention [Compound No. (14d)] by Production Method A To 5 ml of chloroform, 0.57 g of 3-acetyl-4-hydroxy-2H-1-benzopyran-2-one and 3- (cyanomethoxy ) 0.45 g of benzaldehyde and 0.20 g of piperidine were dissolved, and the mixture was heated under reflux for 1 hour 30 minutes while removing water with a Soxhlet extractor filled with molecular sieves. After cooling to room temperature, the reaction mixture was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The precipitated crystals are washed with a mixture of 10 ml of dioxane and 10 ml of chloroform, followed by washing with 10 ml of t-butyl methyl ether, whereby 4-hydroxy-3- [3- [3- (cyanomethoxy) phenyl] -1-oxo- 0.56 g of yellow crystals of 2-propenyl] -2H-1-benzopyran-2-one [Compound No. (14d)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 4.83 (s, 2H), 7.08 (d, 1H, J = 8.0 Hz), 7.20-7.40 (5H), 7.70 (t, 1H, J = 7.1 Hz), 8.01 (d, 1H, J = 15.9 Hz), 8.11 (d, 1H, J = 8.1 Hz), 8.44 (d , 1H, J = 15.6 Hz)

Example d-2 Synthesis of Compound of the Present Invention [Compound No. (15d)] by Production Method B 5 ml of hexamethylphosphoramide and 4-hydroxy-3- [3- [3- (cyanomethoxy) phenyl] -1-oxo- 2-Propenyl] -2H-1-benzopyran-2-one To a mixture of 0.40 g, 52 mg of sodium hydride (60% oily) was added and stirred at room temperature for 1 hour. Next, 0.17 g of dimethyl sulfate was added and stirred overnight at room temperature. The reaction mixture was then poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give 4-methoxy-3- [3- [3- (cyanomethoxy) phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one [compound No. (15d)] was obtained as 81 mg of pale yellow crystals.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 4.04 (s, 3H), 4.80 (s, 2H), 7.04 (d, 1H, J = 5.6 Hz), 7. 16 (d, 1H, J = 16.1 Hz), 7.10 to 7.40 (5H), 7.58 (d, 1H, J = 16.2 Hz), 7.60 (t, 1H), 7. 93 (d, 1H, J = 8.1 Hz)

Example d-3 Synthesis of Compound of the Present Invention [Compound No. (21d)] by Production Method A 3-acetyl-4-hydroxy-2H-1-benzopyran-2-one 0.18 g, 3- (methoxyacetyl) in 3 ml of chloroform Amino) benzaldehyde (0.17 g) and piperidine (60 mg) were dissolved, and the mixture was heated under reflux for 1 hour and 10 minutes while removing water with a Soxhlet extractor filled with molecular sieves. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction corresponding to Rf = 0.3 was collected and concentrated by thin layer chromatography (silica gel, chloroform (containing 2% methanol)) to give 4-hydroxy-3- [ 0.30 g of 3- [3- (methoxyacetylamino) phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one [Compound No. (21d)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 3.54 (s, 3H), 4.05 (s, 2H), 7.20 to 7.31 (2H), 7.33 (t, 1H, J = 7.1 Hz), 7.49 (d, 1H, J = 7.8 Hz), 7.70 (dt, 1H, J = 1.7, 7.3 Hz), 7.76 (s, 1H) ), 7.86 (d, 1H, J = 7.1 Hz), 8.03 (d, 1H, J = 16.1 Hz), 8.10 (dd, 1H, J = 1.7, 8.1 Hz) , 8.35 (s, 1H), 8.43 (d, 1H, J = 15.9 Hz), 11.21 (s, 1H)

Example d-4 Synthesis of Compound of the Present Invention [Compound No. (22d)] 4-Hydroxy-3- [3- [3- (methoxyacetylamino) phenyl] -1-oxo-2 was added to a mixture of 5 ml of tetrahydrofuran and 6 ml of dichloromethane. -Propenyl] -2H-1-benzopyran-2-one 0.59 g, triphenylphosphine 0.45 g and methanol 55 mg were added, and 0.74 g of a 40% toluene solution of diethyl azodicarboxylate was added dropwise to the mixture. The mixture was stirred at room temperature for 40 minutes, and the reaction solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 4-methoxy-3- [3- [3- (methoxyacetylamino) phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one [ Compound No. (22d)] 0.18 g was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 3.51 (s, 3H), 4.02 (s, 3H), 4.04 (s, 2H), 7.16 (d, 1H, J = 16.2 Hz), 7.29-7.39 (4H), 7.59 (d, 1H, J = 16.4 Hz), 7.61 (dt, 1H, J = 1.5, 8.8 Hz) ), 7.87 (s, 1H), 7.92 (dd, 1H, J = 1.5, 8.1 Hz), 8.30 (s, 1H)

Example d-5 Synthesis of Compound of the Present Invention [Compound No. (24d)] by Production Method A 3-acetyl-4-hydroxy-2H-1-benzopyran-2-one 2.04 g, 3-[(2 -Methoxyethoxy) carbonylamino] benzaldehyde (2.23 g) and piperidine (60 mg) were dissolved and heated under reflux for 1 hour and 30 minutes while removing water with a Soxhlet extractor packed with molecular sieves. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction corresponding to Rf = 0.3 was collected by thin layer chromatography (silica gel, hexane / acetone (1: 1)) and concentrated to give 4-hydroxy-3- 3.42 g of [3- [3-[(2-methoxyethoxy) carbonylamino] phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one [compound number (24d)] was obtained. .
¹ H-NMR (400 MHz, DMSO-d ₆ ) δ (ppm): 3.30 (s, 3H), 3.59 (t, 2H, J = 3.2 Hz), 4.23 (t, 2H, J = 4.6 Hz), 7.35-7.50 (5H), 7.60 (d, 1H, J = 7.6 Hz), 7.82 (t, 1H, J = 7.1 Hz), 7.94. (S, 1H), 7.97 (d, 1H, J = 15.9 Hz), 8.06 (d, 1H, J = 8.1 Hz), 8.27 (d, 1H, J = 15.9 Hz) , 9.97 (s, 1H)

Example d-6 Synthesis of Compound of the Present Invention [Compound No. (25d)] by Production Method B
Instead of 4-hydroxy-3- [3- [3- (cyanomethoxy) phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one, 4-hydroxy-3- [3- [3-[(2-methoxyethoxy) carbonylamino] phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one The same as Example d-2 except that 2.0 g was used. 4-methoxy-3- [3- [3-[(2-methoxyethoxy) carbonylamino] phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one [compound number (25d )] 1.28 g was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 3.43 (s, 3H), 3.65 (t, 2H, J = 4.2 Hz), 4.03 (s, 3H), 4. 34 (t, 2H, J = 4.4 Hz), 6.73 (s, 1H), 7.14 (d, 1H, J = 16.4 Hz), 7.25 to 7.50 (5H), 7. 56 (d, 1H, J = 16.4 Hz), 7.59 (t, 1H), 7.70 (s, 1H), 7.91 (dd, 1H, J = 8.8 Hz)

Example d-7 Synthesis of Compound of the Present Invention [Compound No. (32d)] by Production Method A
4-hydroxy-3- [3 In the same manner as in Example d-1, except that 0.56 g of 4-[(2-hydroxyethyl) aminocarbonyl] benzaldehyde was used instead of 3- (cyanomethoxy) benzaldehyde. 58 mg of [4-[(2-hydroxyethyl) aminocarbonyl] phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (32d)] was obtained.
¹ H-NMR (400 MHz, DMSO-d ₆ ) δ (ppm): 3.35 (t, 2H, J = 5.6 Hz), 3.52 (t, 2H, J = 6.1 Hz), 7.40 -7.55 (2H), 7.80-7.90 (3H), 7.90-8.00 (2H), 8.80-8.10 (2H), 8.32 (d, 1H, J = 15.9 Hz), 8.56 (t, 1 H, J = 5.4 Hz)

Example d-8 Synthesis of Compound of the Present Invention [Compound No. (33d)] by Production Method A
Instead of 3- (cyanomethoxy) benzaldehyde, 4-hydroxy-3- [ Yellow crystals of 3- [3-[[(methoxycarbonylmethyl) amino] carbonyl] phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (33d)] Obtained .65 g.
¹ H-NMR (400 MHz, DMSO-d ₆ ) δ (ppm): 3.67 (s, 3H), 4.05 (d, 2H, J = 6.0 Hz), 7.40 to 7.48 (2H ), 7.58 to 7.68 (1H), 7.83 (t, 1H, J = 7.6 Hz), 7.90 to 8.00 (2H), 8.00 to 8.10 (2H), 8.25 (s, 1H), 8.33 (d, 1H, J = 15.6 Hz), 9.15 (t, 1H, J = 6.0 Hz)

Example d-9 Synthesis of Compound of the Present Invention [Compound No. (36d)] by Production Method A
4-Hydroxy-3- [3 in the same manner as in Example d-1, except that 1.60 g of 4-[(2-methoxyethyl) aminocarbonyl] benzaldehyde was used instead of 3- (cyanomethoxy) benzaldehyde. 0.68 g of yellow crystals of [4-[(2-methoxyethyl) aminocarbonyl] phenyl] -1-oxo-2-propenyl] -6-methyl-2H-pyran-2-one [Compound No. (36d)] Got.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 3.41 (s, 3H), 3.59 (t, 2H, J = 5.2 Hz), 3.69 (t, 2H, J = 5) .2 Hz), 6.55 (s, 1H), 7.30-7.40 (2H), 7.65-7.75 (1H), 7.78 (d, 2H, J = 8.4 Hz), 7.84 (d, 2H, J = 8.4 Hz), 8.04 (d, 1H, J = 16.0 Hz), 8.10 (d, 1H, J = 8.0 Hz), 8.50 (d , 1H, J = 15.6 Hz), 11.29 (s, 1H)

Example d-10 Synthesis of Compound of the Present Invention [Compound No. (49d)] by Production Method A
Instead of 3- (cyanomethoxy) benzaldehyde, 4-hydroxy-3- [3- [3- [3- [3- [3- (3-hydroxypropoxy) benzaldehyde was used in the same manner as in Example d-1, except that 0.50 g was used. 0.54 g of yellow crystals of (3-hydroxypropoxy) phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one [Compound No. (49d)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 1.71 (t, 1H, J = 5.3 Hz), 2.06 to 2.12 (m, 2H), 3.88 to 3.92 (M, 2H), 4.20 (t, 2H, J = 6.0 Hz), 6.99 to 7.01 (m, 1H), 7.25 to 7.36 (m, 5H), 7.67 ˜7.71 (m, 1H), 8.02 (d, 1H, J = 15.8 Hz), 8.09 to 8.11 (m, 1H), 8.42 (d, 1H, J = 15. 8Hz)

Example d-11 Synthesis of Compound of the Present Invention [Compound No. (50d)] by Production Method B
Instead of 4-hydroxy-3- [3- [3- (cyanomethoxy) phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one, 4-hydroxy-3- [3- In the same manner as in Example d-2 except that 267 mg of [3- (3-hydroxypropoxy) phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one was used, 4-methoxy- 22 mg of 3- [3- [3- (3-hydroxypropoxy) phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2-one [compound number (50d)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 1.62 (t, 1H, J = 5.4 Hz), 2.03 to 2.09 (m, 2H), 3.85 to 3.89 (M, 2H), 4.04 (s, 3H), 4.15 (t, 2H, J = 6.1 Hz), 6.95 to 6.98 (m, 1H), 7.11 to 7.18. (M, 2H), 7.27 to 7.36 (m, 4H), 7.55 to 7.62 (m, 2H), 7.90 to 7.93 (m, 1H)

Example e-1 Synthesis of Compound of the Present Invention [Compound No. (17e)] In silica gel column chromatography of Example d-3, thin layer chromatography (silica gel, chloroform (containing 2% methanol)) gave Rf = 0. By collecting and concentrating the compartment corresponding to 1, 4-piperidino-3- [3- [3- (methoxyacetylamino) phenyl] -1-oxo-2-propenyl] -2H-1-benzopyran-2- 36.1 mg of ON [compound number (17e)] was obtained.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm): 1.75 to 2.05 (6H), 3.50 (s, 3H), 3.85 to 3.95 (4H), 4.01 ( s, 2H), 7.08 (d, 1H, J = 15.7 Hz), 7.20-7.30 (3H), 7.33 (t, 1H, J = 8.1 Hz), 7.42 ( d, 1H, J = 15.9 Hz), 7.51 (t, 1H, J = 7.3 Hz), 7.57 (d, 1H), 7.82 (s, 1H), 8.07 (dd, 1H, J = 1.5, 7.8 Hz), 8.27 (s, 1H)

Example e-2 Synthesis of Compound of the Present Invention [Compound No. (18e)] In silica gel column chromatography of Example d-5, Rf = 0. The compartment corresponding to 1 is collected and concentrated to give 4-piperidino-3- [3- [3-[(2-methoxyethoxy) carbonylamino] phenyl] -1-oxo-2-propenyl] -2H-1 -0.15 g of benzopyran-2-one [Compound No. (18e)] was obtained.
¹ H-NMR (400 MHz, DMSO-d ₆ ) δ (ppm): 1.70 to 1.95 (6H), 3.31 (s, 3H), 3.55 (t, 2H, J = 4.6 Hz) ), 3.79 (s, 2H), 3.95 to 4.20 (4H), 4.19 (t, 2H, J = 4.4 Hz), 7.21 (d, 1H, J = 8.3 Hz) ), 7.28-7.58 (5H), 7.69 (s, 1H), 7.85 (dd, 1H, J = 1.7, 8.1 Hz), 9.79 (s, 1H)

Example 3 (Preparation of a plasmid having a reporter gene linked to a transcriptional regulatory region of a 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. The mixed solution was mixed with 2 volumes of ethanol, 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 obtained genomic DNA lysate (equivalent to 1 μg of genomic DNA), 1 μl each of the oligonucleotide consisting of the base sequence shown in SEQ ID NO: 1 and the oligonucleotide consisting of the base sequence shown in SEQ ID NO: 2 (10 pmol / μl), distilled 29 μl of water, 5 μl of buffer attached to TaKaRa LA Taq (Takara Shuzo, catalog number RR002A), 5 μl of Mg ²⁺ solution, 5 μl of dNTP mixture, and 0.5 μl of TaKaRa LA Taq (Takara Shuzo, catalog number RR002A) were mixed. 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 30 times. 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 the 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 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. 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.

Example 4 (Measurement of transcriptional regulatory ability of type I collagen gene of test compound using reporter gene expression level as an 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. Subsequently, 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 to stand 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 the compound numbers (1a), (2a), (4a), (5a), (7a) to (10a), (14a), (15a), (21a), 22a), (24a), (25a), (33a), (36a), (1b), (2b), (14b) to (16b), (19b), (20b), (14d), (15d) , (21d), (22d), (24d), (25d), (32d), (33d), (36d), (17e) or the compound of the present invention represented by (17e) or 18e (Hereinafter referred to as DMSO) was added in a volume of 10 μl (final concentration 1 μM). In the control, only 10 μl of 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 onto 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
Compound Nos. (1a), (2a), (4a), (5a), (7a) to (10a), (14a), (15a), (21a), (22a), (24a), (25a), (33a), (36a), (1b), (2b), (14b) to (16b), (19b), (20b), (14d), (15d), (21d), (22d), (24d) ), (25d), (32d), (33d), (36d), (17e) or (18e), the degree of inhibition of the compound of the present invention was 70 or more. It was confirmed that these compounds have the ability to inhibit the type I collagen gene transcription promoting ability of TGF-β and to suppress the type I collagen gene transcription.

Example 5 (Improvement of chronic renal failure by administration of the compound of the present invention)
(1) Preparation of anti-Thy-1 antibody (IgG) Using MAbTrap Kit (Amersham Biosciences, catalog number 17-1128-01), ascites lyophilized powder (CEDALANE) containing anti-rat CD90 (Thy1.1) monoclonal antibody IgG from lot number 05122).
6 ml of binding buffer was added to 3 ml of ascites and recovered sufficiently, and passed through a 0.22 μm filter. The obtained solution was applied to a pre-buffered column, and then washed with 10 ml binding buffer. Thereafter, elution was performed with a 5 ml elution buffer. Fraction was fractionated every 1 ml from the time of washing, and the protein concentration of each fraction was measured using bovine serum albumin as a standard. A single peak was confirmed from the elution pattern, and the IgG fraction was dialyzed against physiological saline at 4 ° C. overnight. The protein concentration of the obtained anti-Thy-1 antibody (IgG) was calculated.
(2) Administration of anti-Thy-1 antibody (IgG) and compound Compound numbers (1a), (4a), (9a), (14a), (21a), (33a), (19b) or (21d) The present invention compounds (hereinafter referred to as the present compound (1a), (4a), (9a), (14a), (21a), (33a), (19b) or the present compound (21d)) and Corn oil as a medium was weighed and mixed using a mortar and pestle to prepare a 3 mg / kg solution. Four 7-week-old male Wistar rats [Nippon Charles River Co., Ltd.] were used per group, and 60 μg / ml anti-Thy-1 antibody (IgG) or physiological saline was supplied from the tail vein at a rate of 5 ml / kg. It was intravenously injected. Immediately after administration, the compound of the present invention or corn oil was orally administered repeatedly at a rate of 5 ml / kg for 7 days. The dose of the compound of the present invention was 15 mg / kg / day.
(3) Quantification of type I collagen gene mRNA in renal glomerulus The rats raised as described in (2) above were sacrificed by whole blood collection the day after the final administration, and the kidneys were removed. Total RNA was isolated from the kidney cortex of the removed kidney using RNeasy Mini Kit (QIAGEN, catalog number 74106). To 5 μl (50 ng) of the separated total RNA, 1 μl of 20 μM oligo dT and 4 μl of RNase-free distilled water were added, and the mixture was ice-cooled immediately after incubation at 65 ° C. for 5 minutes. To this 10 μl solution, 5 × 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 Promega) were added at 25 ° C. for 5 minutes, 42 ° C. 1 The reverse transcription reaction was carried out at 70 ° C. for 15 minutes.
In 5 μl of the reverse transcription reaction solution, 2 μl of each 1.25 pmol / μl primer represented by SEQ ID NOs: 3 and 4 and a DNA detection probe of type I collagen gene represented by SEQ ID NO: 5 (FAM-ctcgccttca tgcgcctgct agc-TAMRA) 1 .25 μl, Rodent GAPDH primer 0.25 μl, Rodent GAPDH probe 0.25 μl, TaqMan Universal PCR Master Mix (all Applied Biosystems) 12.5 μl and sterile water 1.5 μl Optical 96-Well React Pli Mixed in wells of System, catalog number N801-0560). As standard, 5 μl each of rat kidney cortex cDNA 500, 250, 125, 62.5, 31.25, 15.625 ng / μl prepared in advance was used instead of 5 μl of the reverse transcription reaction solution. 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 a standard straight line, the amount of type I collagen and the amount of GAPDH of each sample were calculated, and the amount of transcription was calculated according to the following formula.
Type I collagen transcription amount = Type I collagen amount / GAPDH amount As a statistical treatment of the obtained results, F-test of the dispersion ratio between the two groups of the anti-Thy-1 antibody and corn oil administration group and each of the other groups When there was no significant difference in variance, Student's t test (one side) was performed, and when there was a significant difference in variance, Aspin-Welch test (one side) was performed. The results are shown in Table 36.
It was confirmed that the compound (1a), (4a), (9a), (14a), (21a), (33a), (19b) or (21d) of the present invention has the ability to improve chronic renal failure.

  According to the present invention, a composition (that is, a collagen accumulation inhibitor or a fibrosis therapeutic agent) that improves the fibrosis of a tissue by reducing the expression level of a type I collagen gene in the tissue and decreasing the amount of collagen accumulation. Development and provision are possible.

SEQ ID NO: 1
Oligonucleotide SEQ ID NO: 2 designed to amplify the transcriptional regulatory region of type I collagen gene as a primer for PCR
Oligonucleotide SEQ ID NO: 3 designed to amplify the transcriptional regulatory region of type I collagen gene as a primer for PCR
Oligonucleotide SEQ ID NO: 4 designed to detect DNA of type I collagen gene as a primer for PCR
Oligonucleotide SEQ ID NO: 5 designed to detect DNA of type I collagen gene as a primer for PCR
Oligonucleotide designed to detect DNA of type I collagen gene as a probe

Claims (24)

Formula (XIV)

A 2H-pyran-2-one compound represented by: Formula (XV)

A 2H-pyran-2-one compound represented by: Formula (XVI)

A 2H-pyran-2-one compound represented by: Formula (XVII)

A 2H-pyran-2-one compound represented by: Formula (XVIII)

A 2H-pyran-2-one compound represented by: Formula (XIX)

A 2H-pyran-2-one compound represented by: Formula (XX)

A 2H-pyran-2-one compound represented by: Formula (XXI)

A 2H-pyran-2-one compound represented by: Formula (XXII)

A 2H-pyran-2-one compound represented by: Formula (XXIII)

A 2H-1-benzopyran-2-one compound represented by: Formula (XXIV)

A 2H-1-benzopyran-2-one compound represented by: Formula (XXV)

A 2H-1-benzopyran-2-one compound represented by: Use of the compound according to claims 1 to 12 as an active ingredient for suppressing transcription of a type I collagen gene (except for use in humans) . Claim 1-12 compound type I collagen gene transcription repression composition characterized by containing an inert carrier according. Use of the compound according to claims 1 to 12 as an active ingredient for improving tissue fibrosis by reducing the expression level of type I collagen gene and leading to a decrease in collagen accumulation (however, use for humans) Except) . Claim 1-12 compound and tissue fibrosis improving composition characterized by containing an inert carrier according. An effective amount of a compound of claim 1 to 12, wherein the tissue fibrosis improved method characterized by administering to a non-human mammal in need of treatment to improve tissue fibrosis. Use of the compound according to claims 1 to 12 as an active ingredient for suppressing the action of TGF-β (excluding use for humans) . TGF-beta activity inhibiting composition characterized by containing a billing compound of claim 1 to 12, wherein the inert carrier. Use of the compound according to claims 1 to 12 as an active ingredient for obtaining a hair nourishing effect by inhibiting the promotion of the transition to the hair regression phase by TGF-β and leading to an extension of the hair growth phase (however, human Except for use against) . Hair tonic composition characterized by containing a billing compound of claim 1 to 12, wherein the inert carrier. An effective amount of a compound of claim 1 to 12, wherein, hair tonic method characterized by administering to a non-human mammal in need of hair growth treatment. As an active ingredient for the treatment of chronic renal failure, the use of claim 1 to 12 A compound according (excluding for human use). Chronic renal failure treating agent characterized by containing a billing compound of claim 1 to 12, wherein the inert carrier.