JPH10139767A

JPH10139767A - Herbicidal aniline derivative

Info

Publication number: JPH10139767A
Application number: JP5579897A
Authority: JP
Inventors: Muneharu Mizukai; 宗治水貝; Hiroyuki Komai; 浩之駒井; Noriaki Kudo; 法明工藤; Kazuo Sato; 佐藤　　一雄; Toyokuni Honma; 豊邦本間; Junji Kadotani; 淳二門谷; Kiyoshi Koi; 清小井; Mitsuru Ito; 充伊藤
Original assignee: Sankyo Co Ltd
Current assignee: Sankyo Co Ltd
Priority date: 1996-03-11
Filing date: 1997-03-11
Publication date: 1998-05-26
Anticipated expiration: 2017-03-11
Also published as: JP3051356B2

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound useful as a herbicide hardly manifesting phytotoxicity to paddy rice but manifesting excellent herbicidal activities against Echinochloa oryzicola Vasing. which is a strongly damaging weed in a paddy field in a low dose. SOLUTION: This compound is represented by formula I [R<1> is a (halogen, etc.,-substituted) 1-6C alkyl (Z1 ), a (halogen-substituted) 1-6C alkoxy (Z2 ), etc.; R<2> is H, an (OH, etc.,-substituted) 1-6C alkyl, etc.; R<3> is Z1 , Z2 , etc.; R<4> and R<5> are each H or a 1-6C alkyl; R<6> is Z1 , Z2 , etc.; A, X and Q are each O or S; (m) and (n) are each 0-4] and its salt, e.g. N-[4-(benzothiazol-2-ylmethoxy) phenyl]acetamide. The compound represented by formula I is obtained by reacting a compound represented by formula II [K is a group represented by the formula N(R<2> )C(=X)R<1> ] with a compound represented by formula III (L is an eliminable group).

Description

DETAILED DESCRIPTION OF THE INVENTION

【０００１】[0001]

【発明の属する技術分野】本発明は、優れた除草活性を
有する新規なアニリン誘導体及びそれらを有効成分とし
て含有する農薬（除草剤）に関する。[0001] The present invention relates to novel aniline derivatives having excellent herbicidal activity and pesticides (herbicides) containing them as active ingredients.

【０００２】[0002]

【従来の技術】従来より、作物に対して薬害を与えず有
害雑草のみを選択的に枯殺する除草剤が要望されてい
る。又、種々研究された結果、多くの選択的除草剤が公
表されているが、さらに優れた除草剤の出現が望まれて
いる。2. Description of the Related Art There has been a demand for a herbicide that selectively kills only harmful weeds without causing phytotoxicity to crops. As a result of various studies, many selective herbicides have been published, but the emergence of even better herbicides is desired.

【０００３】米国特許４１９３７８７及び米国特許４４
２３２３７には、除草活性を有するカルバミド酸誘導体
が記載されているが、部分構造として１，４−ベンゾジ
オキサン環を有することを必須の特徴としており、本願
化合物とは化学構造を異にする。また、特開昭５８−５
２２８０号公報には、除草活性を有するベンゾチアゾー
ル誘導体が記載されているが、それらはウレア部分構造
を有することを必須の特徴としており、本願化合物とは
化学構造を異にする。[0003] US Patent No. 4,193,787 and US Patent No. 44
No. 23237 describes a carbamic acid derivative having herbicidal activity, which has an essential feature of having a 1,4-benzodioxane ring as a partial structure, and has a different chemical structure from the compound of the present invention. Also, Japanese Patent Application Laid-Open No. 58-5
No. 2280 describes benzothiazole derivatives having herbicidal activity, but they have an essential feature of having a urea partial structure, and have a different chemical structure from the compound of the present invention.

【０００４】[0004]

【発明が解決しようとする課題】本発明者は、アニリン
誘導体の合成とその生物活性について永年に亘り鋭意研
究を行った結果、既知の化合物とは構造を異にした新規
なアニリン誘導体が、水稲に対する薬害をほとんど示さ
ず、しかも水田の強害雑草であるタイヌビエに対し低薬
量で優れた除草活性を示すことを見い出し、本発明を完
成した。SUMMARY OF THE INVENTION The inventor of the present invention has conducted intensive studies on the synthesis of aniline derivatives and their biological activities over many years, and as a result, a novel aniline derivative having a structure different from that of a known compound has been obtained. The present inventors have found that the present invention shows little herbicidal activity against the rice plant, and shows excellent herbicidal activity at a low dose in herbaceous rice, which is a highly damaging weed in paddy fields, and completed the present invention.

【０００５】[0005]

【課題を解決するための手段】本発明は、下記一般式
（Ｉ）The present invention provides a compound represented by the following general formula (I):

【０００６】[0006]

【化２】 Embedded image

【０００７】［式中、Ｒ¹ は、Ｃ１〜Ｃ６アルキル基
（当該アルキル基は、Ｃ１〜Ｃ６アルコキシ基又は１乃
至４個のハロゲン原子により置換されても良い）、Ｃ３
〜Ｃ６シクロアルキル基、Ｃ１〜Ｃ６アルコキシ基（当
該アルコキシ基は、１乃至４個のハロゲン原子により置
換されても良い）又はＣ１〜Ｃ６アルキルチオ基（当該
アルキルチオ基は、１乃至４個のハロゲン原子により置
換されても良い）を示し、Ｒ² は、水素原子、Ｃ１〜Ｃ
６アルキル基（当該アルキル基は、水酸基又は１乃至４
個のハロゲン原子により置換されても良い）、Ｃ３〜Ｃ
６シクロアルキル基、Ｃ２〜Ｃ６アルケニル基（当該ア
ルケニル基は、１乃至４個のハロゲン原子により置換さ
れても良い）、Ｃ２〜Ｃ６アルキニル基（当該アルキニ
ル基は、１乃至４個のハロゲン原子により置換されても
良い）又は式−ＹＲ⁷ で表される基を示し、Ｒ³ は、Ｃ
１〜Ｃ６アルキル基（当該アルキル基は、Ｃ１〜Ｃ６ア
ルコキシ基又は１乃至４個のハロゲン原子により置換さ
れても良い）、Ｃ３〜Ｃ６シクロアルキル基、Ｃ１〜Ｃ
６アルコキシ基（当該アルコキシ基は、１乃至４個のハ
ロゲン原子により置換されても良い）、Ｃ２〜Ｃ６アル
ケニル基（当該アルケニル基は、１乃至４個のハロゲン
原子により置換されても良い）、Ｃ２〜Ｃ６アルキニル
基（当該アルキニル基は、１乃至４個のハロゲン原子に
より置換されても良い）、ハロゲン原子、ニトロ基又は
式−ＣＯＲ⁸ で表される基を示し、Ｒ⁴ 及びＲ⁵ は、同
一又は異なって、水素原子又はＣ１〜Ｃ６アルキル基を
示し、Ｒ⁶ は、Ｃ１〜Ｃ６アルキル基（当該アルキル基
は、Ｃ１〜Ｃ６アルコキシ基又は１乃至４個のハロゲン
原子により置換されても良い）、Ｃ３〜Ｃ６シクロアル
キル基、Ｃ１〜Ｃ６アルコキシ基（当該アルコキシ基
は、１乃至４個のハロゲン原子により置換されても良
い）、Ｃ２〜Ｃ６アルケニル基（当該アルケニル基は、
１乃至４個のハロゲン原子により置換されても良い）、
Ｃ２〜Ｃ６アルキニル基（当該アルキニル基は、１乃至
４個のハロゲン原子により置換されても良い）、ハロゲ
ン原子、ニトロ基又は式−ＣＯＲ⁸ で表される基を示
し、Ｒ⁷ は、Ｃ１〜Ｃ６アルキル基（当該アルキル基
は、Ｃ１〜Ｃ６アルコキシ基、Ｃ１〜Ｃ６アルキルチオ
基又は１乃至４個のハロゲン原子により置換されても良
い）、Ｃ３〜Ｃ６シクロアルキル基、Ｃ２〜Ｃ６アルケ
ニル基（当該アルケニル基は、１乃至４個のハロゲン原
子により置換されても良い）、Ｃ２〜Ｃ６アルキニル基
（当該アルキニル基は、１乃至４個のハロゲン原子によ
り置換されても良い）、Ｃ６〜Ｃ１４アリール基（当該
アリール基は、１乃至３個のＣ１〜Ｃ６アルキル基、１
乃至３個のＣ１〜Ｃ６アルコキシ基又は１乃至４個のハ
ロゲン原子により置換されても良い）、Ｃ７〜Ｃ１１ア
ラルキル基（当該アラルキル基は、１乃至４個のハロゲ
ン原子により置換されても良い）又は少なくとも１個の
酸素原子、硫黄原子若しくは窒素原子を含み環原子数が
４乃至１０である複素環基（当該複素環基は、１乃至３
個のＣ１〜Ｃ６アルキル基、１乃至３個のＣ１〜Ｃ６ア
ルコキシ基又は１乃至４個のハロゲン原子により置換さ
れても良く、又、ベンゼン環と縮合していても良い）を
示し、Ｒ⁸ は、水素原子、Ｃ１〜Ｃ６アルキル基、Ｃ３
〜Ｃ６シクロアルキル基又はＣ１〜Ｃ６アルコキシ基を
示し、Ａは、酸素原子又は硫黄原子を示し、Ｘは、酸素
原子又は硫黄原子を示し、Ｙは、式−ＣＯ−、式−ＣＯ
Ｏ−、式−ＣＨ₂ Ｏ−、式−ＣＨ₂ Ｓ−、式−ＣＨ₂ Ｃ
Ｈ₂ Ｏ−、式−ＣＨ₂ ＣＨ₂ Ｓ−、式−ＣＨ₂ ＣＯ−、
式−ＣＨ₂ ＣＯＯ−、式−ＣＨ（ＣＨ₃ ）ＣＯＯ−、式
−ＣＨ₂ ＣＨ₂ ＣＯ−、式−ＣＨ₂ ＯＣＯ−、式−ＣＨ
₂ ＯＣＯＯ−又は式−ＣＨ₂ ＣＨ₂ ＯＣＯ−で表される
基を示し、Ｑは、酸素原子又は硫黄原子を示し、ｍは、
０、１、２、３又は４を示し（但し、ｍが２、３又は４
の場合は、それぞれのＲ³ は、同一又は異なっても良
い）、ｎは、０、１、２、３又は４を示す（但し、ｎが
２、３又は４の場合は、それぞれのＲ⁶ は、同一又は異
なっても良い）。］で表わされるアニリン誘導体及び除
草剤として許容されるそれらの塩である。Wherein R ¹ is a C1 to C6 alkyl group (the alkyl group may be substituted by a C1 to C6 alkoxy group or 1 to 4 halogen atoms);
-C6 cycloalkyl group, C1-C6 alkoxy group (the alkoxy group may be substituted by 1 to 4 halogen atoms) or C1 to C6 alkylthio group (the alkylthio group is 1 to 4 halogen atoms R ² is a hydrogen atom, C 1 -C
6 alkyl groups (the alkyl groups may be hydroxyl groups or 1 to 4
May be substituted by two halogen atoms), C3-C3
6 cycloalkyl group, C2 to C6 alkenyl group (the alkenyl group may be substituted by 1 to 4 halogen atoms), C2 to C6 alkynyl group (the alkynyl group is 1 to 4 halogen atoms may be substituted) or a group represented by the formula -YR ^7, R ³ is, C
A C1-C6 alkyl group (the alkyl group may be substituted by a C1-C6 alkoxy group or 1-4 halogen atoms), a C3-C6 cycloalkyl group, a C1-C6
6 alkoxy groups (the alkoxy group may be substituted by 1 to 4 halogen atoms), C2 to C6 alkenyl groups (the alkenyl group may be substituted by 1 to 4 halogen atoms), C2~C6 alkynyl group (said alkynyl group may be substituted by 1 to 4 halogen atoms), a halogen atom, a group represented by the nitro group, or the formula -COR ^8, R ⁴ and R ⁵ are The same or different, and represents a hydrogen atom or a C1 to C6 alkyl group, and R ⁶ is a C1 to C6 alkyl group (the alkyl group may be substituted with a C1 to C6 alkoxy group or 1 to 4 halogen atoms. Good), C3-C6 cycloalkyl group, C1-C6 alkoxy group (the alkoxy group may be substituted by 1 to 4 halogen atoms), C2-C6 alkyl group Le group (said alkenyl group,
May be substituted by 1 to 4 halogen atoms),
C2~C6 alkynyl group (said alkynyl group may be substituted by 1 to 4 halogen atoms), a halogen atom, a nitro group or a group of the formula -COR ^8, R ⁷ is C1 to C6 alkyl group (the alkyl group may be substituted by a C1 to C6 alkoxy group, a C1 to C6 alkylthio group or 1 to 4 halogen atoms), a C3 to C6 cycloalkyl group, a C2 to C6 alkenyl group (the The alkenyl group may be substituted with 1 to 4 halogen atoms, a C2 to C6 alkynyl group (the alkynyl group may be substituted with 1 to 4 halogen atoms), a C6 to C14 aryl group. (The aryl group includes 1 to 3 C1 to C6 alkyl groups, 1
3 to 3 C1 to C6 alkoxy groups or 1 to 4 halogen atoms may be substituted), C7 to C11 aralkyl groups (the aralkyl groups may be substituted with 1 to 4 halogen atoms) Or a heterocyclic group containing at least one oxygen atom, sulfur atom, or nitrogen atom and having 4 to 10 ring atoms (the heterocyclic group is 1 to 3
Number of C1~C6 alkyl group may be substituted by 1 to 3 of C1~C6 alkoxy or 1 to 4 halogen atoms, also represents an optionally condensed with a benzene ring), R ⁸ Represents a hydrogen atom, a C1-C6 alkyl group, C3
To C6 cycloalkyl group or C1 to C6 alkoxy group, A represents an oxygen atom or a sulfur atom, X represents an oxygen atom or a sulfur atom, and Y represents a formula -CO-, a formula -CO
O-, wherein -CH ₂ O-, wherein -CH ₂ S-, wherein -CH ₂ C
H ₂ O-, wherein -CH _₂ CH ₂ S-, wherein -CH ₂ CO-,
Formula -CH ₂ COO-, wherein -CH (CH ₃₎ COO-, wherein -CH ₂ CH ₂ CO-, the formula -CH ₂ OCO-, the formula -CH
₂ -OCOO- or The equation -CH ₂ CH ₂ group represented by OCO-, Q represents an oxygen atom or a sulfur atom, m is
0, 1, 2, 3 or 4 (where m is 2, 3 or 4)
, Each R ³ may be the same or different), and n represents 0, 1, 2, 3 or 4 (however, when n is 2, 3 or 4, each R ⁶⁾ May be the same or different). And the salts thereof that are acceptable as herbicides.

【０００８】本明細書において、「Ｃ１〜Ｃ６アルキル
基」とは、例えば、メチル、エチル、n-プロピル、イソ
プロピル、n-ブチル、イソブチル、s-ブチル、t-ブチ
ル、n-ペンチル、イソペンチル、2-メチルブチル、ネオ
ペンチル、1-エチルプロピル、n-ヘキシル、4-メチルペ
ンチル、3-メチルペンチル、2-メチルペンチル、1-メチ
ルペンチル、3,3-ジメチルブチル、2,2-ジメチルブチ
ル、1,1-ジメチルブチル、1,2-ジメチルブチル、1,3-ジ
メチルブチル、2,3-ジメチルブチル、2-エチルブチルの
ような、炭素数１乃至６個の直鎖又は分枝鎖アルキル基
である。好適には、炭素数１乃至４個の直鎖又は分枝鎖
アルキル基であり、更に好適には、メチル、エチル、n-
プロピル、イソプロピルのような炭素数１乃至３個の直
鎖又は分枝鎖アルキル基（Ｃ１〜Ｃ３アルキル基）であ
り、より更に好適には、メチル基又はエチル基であり、
最も好適には、メチル基である。In the present specification, "C1-C6 alkyl group" means, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, n-hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1 Linear or branched alkyl groups having 1 to 6 carbon atoms, such as 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl and 2-ethylbutyl is there. Preferably, it is a linear or branched alkyl group having 1 to 4 carbon atoms, more preferably, methyl, ethyl, n-
A straight-chain or branched-chain alkyl group having 1 to 3 carbon atoms (C1 to C3 alkyl group) such as propyl and isopropyl, more preferably a methyl group or an ethyl group;
Most preferably, it is a methyl group.

【０００９】本明細書において、「Ｃ３〜Ｃ６シクロア
ルキル基」とは、例えば、シクロプロピル、シクロブチ
ル、シクロペンチル、シクロヘキシルのような、炭素数
３乃至６個の環状アルキル基である。In the present specification, the "C3-C6 cycloalkyl group" is a cyclic alkyl group having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

【００１０】本明細書において「Ｃ１〜Ｃ６アルコキシ
基により置換されたＣ１〜Ｃ６アルキル基」とは、例え
ば、メトキシメチル、エトキシメチル、n-プロポキシメ
チル、n-ブトキシメチル、s-ブトキシメチル、t-ブトキ
シメチル、ペンチルオキシメチル、ヘキシルオキシメチ
ル、メトキシエチル、エトキシエチル、n-プロポキシエ
チル、n-ブトキシエチル、メトキシプロピル、メトキシ
ブチル、メトキシペンチル、メトキシヘキシルのよう
な、後記「Ｃ１〜Ｃ６アルコキシ基」が１個前記「Ｃ１
〜Ｃ６アルキル基」に結合した基である。好適には、例
えば、メトキシメチル、エトキシメチル、n-プロポキシ
メチル、メトキシエチル、エトキシエチル、n-プロポキ
シエチル、メトキシプロピルのような、炭素数１乃至３
個のアルコキシ基により置換された炭素数１乃至３個の
アルキル基であり、更に好適には、メトキシエチル基又
はエトキシメチル基である。In the present specification, "C1-C6 alkyl group substituted by C1-C6 alkoxy group" means, for example, methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl, s-butoxymethyl, t- -C1-C6 alkoxy groups such as butoxymethyl, pentyloxymethyl, hexyloxymethyl, methoxyethyl, ethoxyethyl, n-propoxyethyl, n-butoxyethyl, methoxypropyl, methoxybutyl, methoxypentyl and methoxyhexyl. "C1
~ C6 alkyl group ". Preferably, it has 1 to 3 carbon atoms such as, for example, methoxymethyl, ethoxymethyl, n-propoxymethyl, methoxyethyl, ethoxyethyl, n-propoxyethyl, methoxypropyl.
And is an alkyl group having 1 to 3 carbon atoms substituted by one alkoxy group, more preferably a methoxyethyl group or an ethoxymethyl group.

【００１１】本明細書において、「Ｃ１〜Ｃ６アルキル
チオ基により置換されたＣ１〜Ｃ６アルキル基」とは、
例えば、メチルチオメチル、エチルチオメチル、n-プロ
ピルチオメチル、n-ブチルチオメチル、t-ブチルチオメ
チル、ヘキシルチオメチル、メチルチオエチル、メチル
チオプロピル、エチルチオエチルのような、後記「Ｃ１
〜Ｃ６アルキルチオ基」が１個前記「Ｃ１〜Ｃ６アルキ
ル基」に結合した基である。好適には、メチルチオメチ
ル、エチルチオメチル、n-プロピルチオメチル、メチル
チオプロピル、エチルチオエチルのような炭素数１乃至
３個のアルキルチオ基により置換された炭素数１乃至３
個のアルキル基である、更に好適には、メチルチオメチ
ル基又はエチルチオメチル基である。[0011] In the present specification, "C1-C6 alkyl group substituted by C1-C6 alkylthio group" means
For example, the following “C1” such as methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, n-butylthiomethyl, t-butylthiomethyl, hexylthiomethyl, methylthioethyl, methylthiopropyl, and ethylthioethyl
To C6 alkylthio group "is one group bonded to the above" C1 to C6 alkyl group ". Preferably, it has 1 to 3 carbon atoms substituted by an alkylthio group having 1 to 3 carbon atoms such as methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, methylthiopropyl and ethylthioethyl.
And more preferably a methylthiomethyl group or an ethylthiomethyl group.

【００１２】本明細書において、「水酸基により置換さ
れたＣ１〜Ｃ６アルキル基」とは、例えば、ヒドロキシ
メチル、1-ヒドロキシエチル、2-ヒドロキシエチル、1-
ヒドロキシプロピル、2-ヒドロキシプロピル、3-ヒドロ
キシプロピル、1-メチル-2-ヒドロキシエチル、4-ヒド
ロキシブチル、5-ヒドロキシペンチル、6-ヒドロキシヘ
キシル、1-メチル-3- ヒドロキシプロピルのような、水
酸基１個が前記「Ｃ１〜Ｃ６アルキル基」に結合した基
である。好適には、ヒドロキシメチル、1-ヒドロキシエ
チル、2-ヒドロキシエチル、3-ヒドロキシプロピルのよ
うな、水酸基により置換されたＣ１〜Ｃ３アルキル基で
あり、更に好適には、ヒドロキシメチル基又は2-ヒドロ
キシエチル基である。In the present specification, the “C1-C6 alkyl group substituted by a hydroxyl group” includes, for example, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxyethyl,
Hydroxyl groups such as hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-methyl-2-hydroxyethyl, 4-hydroxybutyl, 5-hydroxypentyl, 6-hydroxyhexyl, 1-methyl-3-hydroxypropyl One is a group bonded to the “C1-C6 alkyl group”. Preferably, it is a C1-C3 alkyl group substituted by a hydroxyl group such as hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 3-hydroxypropyl, and more preferably, a hydroxymethyl group or a 2-hydroxyl group. It is an ethyl group.

【００１３】本明細書において、「ハロゲン原子」と
は、弗素原子、塩素原子、臭素原子又は沃素原子であ
る。好適には、弗素原子又は塩素原子である。In the present specification, "halogen atom" is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. Preferably, it is a fluorine atom or a chlorine atom.

【００１４】本明細書において「１乃至４個のハロゲン
原子により置換されたＣ１〜Ｃ６アルキル基」とは、例
えば、クロルメチル、ジクロルメチル、トリクロルメチ
ル、1-クロルエチル、2-クロルエチル、1-クロルプロピ
ル、3-クロルプロピル、1-クロルブチル、4-クロルブチ
ル、フルオロメチル、ジフルオロメチル、トリフルオロ
メチル、1-フルオロエチル、2-フルオロエチル、フルオ
ロクロルメチル、ブロモメチル、1-ブロモエチル、2-ブ
ロモエチルのような、同一又は異なった前記「ハロゲン
原子」が１乃至４個前記「Ｃ１〜Ｃ６アルキル基」に結
合した基である。好適には、例えば、クロルメチル、ジ
クロルメチル、トリクロルメチル、1-クロルエチル、2-
クロルエチル、1-クロルプロピル、3-クロルプロピル、
フルオロメチル、ジフルオロメチル、トリフルオロメチ
ル、1-フルオロエチル、2-フルオロエチル、フルオロク
ロルメチル、ブロモメチル、1-ブロモエチル、2-ブロモ
エチルのような、１乃至４個のハロゲン原子により置換
された炭素数１乃至３個のアルキル基であり、更に好適
には、フルオロメチル基、クロロメチル基、トリフルオ
ロメチル基又は2,2,2-トリクロロエチル基である。As used herein, the term "C1-C6 alkyl group substituted by 1 to 4 halogen atoms" means, for example, chloromethyl, dichloromethyl, trichloromethyl, 1-chloroethyl, 2-chloroethyl, 1-chloropropyl, Like 3-chloropropyl, 1-chlorobutyl, 4-chlorobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluorochloromethyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, A group in which 1 to 4 identical or different “halogen atoms” are bonded to the “C1-C6 alkyl group”. Preferably, for example, chloromethyl, dichloromethyl, trichloromethyl, 1-chloroethyl, 2-
Chloroethyl, 1-chloropropyl, 3-chloropropyl,
Carbon number substituted by 1 to 4 halogen atoms such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluorochloromethyl, bromomethyl, 1-bromoethyl, 2-bromoethyl It is one to three alkyl groups, more preferably a fluoromethyl group, a chloromethyl group, a trifluoromethyl group or a 2,2,2-trichloroethyl group.

【００１５】本明細書において、「Ｃ１〜Ｃ６アルコキ
シ基」とは、例えば、メトキシ、エトキシ、n-プロポキ
シ、イソプロポキシ、n-ブトキシ、イソブトキシ、s-ブ
トキシ、t-ブトキシ、n-ペントキシ、イソペントキシ、
2-メチルブトキシ、ネオペントキシ、1-エチルプロポキ
シ、n-ヘキシルオキシ、4-メチルペントキシ、3-メチル
ペントキシ、2-メチルペントキシ、1-メチルペントキ
シ、3,3-ジメチルブトキシ、2,2-ジメチルブトキシ、1,
1-ジメチルブトキシ、1,2-ジメチルブトキシ、1,3-ジメ
チルブトキシ、2,3-ジメチルブトキシ、2-エチルブトキ
シのような、炭素数１乃至６個の直鎖又は分枝鎖アルコ
キシ基である。好適には、例えば、メトキシ、エトキ
シ、n-プロポキシ、イソプロポキシのような、炭素数１
乃至３個の直鎖又は分枝鎖アルコキシ基（Ｃ１〜Ｃ３ア
ルコキシ基）であり、更に好適には、メトキシ基又はエ
トキシ基であり、より更に好適には、メトキシ基であ
る。In the present specification, "C1-C6 alkoxy" means, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentoxy, isopentoxy ,
2-methylbutoxy, neopentoxy, 1-ethylpropoxy, n-hexyloxy, 4-methylpentoxy, 3-methylpentoxy, 2-methylpentoxy, 1-methylpentoxy, 3,3-dimethylbutoxy, 2, 2-dimethylbutoxy, 1,
Linear or branched alkoxy groups having 1 to 6 carbon atoms, such as 1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 2-ethylbutoxy; is there. Preferably, it has 1 carbon atom such as, for example, methoxy, ethoxy, n-propoxy, isopropoxy.
A straight-chain or branched-chain alkoxy group (C1-C3 alkoxy group), more preferably a methoxy group or an ethoxy group, even more preferably a methoxy group.

【００１６】本明細書において「１乃至４個のハロゲン
原子により置換されたＣ１〜Ｃ６アルコキシ基」とは、
例えば、クロルメトキシ、ジクロルメトキシ、トリクロ
ルメトキシ、1-クロルエトキシ、2-クロルエトキシ、1-
クロルプロポキシ、フルオロメトキシ、ジフルオロメト
キシ、トリフルオロメトキシ、1-フルオロエトキシ、2-
フルオロエトキシ、フルオロクロルメトキシ、ブロモメ
トキシのような、同一又は異なった前記「ハロゲン原
子」が１乃至４個前記「Ｃ１〜Ｃ６アルコキシ基」に結
合した基である。好適には、１乃至４個のハロゲン原子
により置換された炭素数１乃至３個のアルコキシ基であ
り、より好適には、フルオロメトキシ基、クロロメトキ
シ基又はトリフルオロメトキシ基であり、更に好適に
は、トリフルオロメトキシ基である。In the present specification, the “C1 to C6 alkoxy group substituted by 1 to 4 halogen atoms” is
For example, chloromethoxy, dichloromethoxy, trichloromethoxy, 1-chloroethoxy, 2-chloroethoxy, 1-chloroethoxy
Chlorpropoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1-fluoroethoxy, 2-
A group in which 1 to 4 identical or different “halogen atoms” are bonded to the “C1 to C6 alkoxy group”, such as fluoroethoxy, fluorochloromethoxy, and bromomethoxy. It is preferably an alkoxy group having 1 to 3 carbon atoms substituted by 1 to 4 halogen atoms, more preferably a fluoromethoxy group, a chloromethoxy group or a trifluoromethoxy group. Is a trifluoromethoxy group.

【００１７】本明細書において、「Ｃ１〜Ｃ６アルキル
チオ基」とは、例えば、メチルチオ、エチルチオ、n-プ
ロピルチオ、イソプロピルチオ、n-ブチルチオ、イソブ
チルチオ、s-ブチルチオ、t-ブチルチオ、n-ペンチルチ
オ、イソペンチルチオ、2-メチルブチルチオ、ネオペン
チルチオ、1-エチルプロピルチオ、n-ヘキシルチオ、4-
メチルペンチルチオ、3-メチルペンチルチオ、2-メチル
ペンチルチオ、1-メチルペンチルチオ、3,3-ジメチルブ
チルチオ、2,2-ジメチルブチルチオ、1,1,- ジメチルブ
チルチオ、1,2-ジメチルブチルチオ、1,3-ジメチルブチ
ルチオ、2,3-ジメチルブチルチオ、2-エチルブチルチオ
のような、炭素数１乃至６個の直鎖又は分岐鎖アルキル
チオ基である。好適には、炭素数１乃至３個の直鎖又は
分岐鎖アルキルチオ基（Ｃ１〜Ｃ３アルキルチオ基）で
あり、更に好適には、メチルチオ基又はエチルチオ基で
ある。In the present specification, the "C1-C6 alkylthio group" includes, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio, t-butylthio, n-pentylthio, Isopentylthio, 2-methylbutylthio, neopentylthio, 1-ethylpropylthio, n-hexylthio, 4-
Methylpentylthio, 3-methylpentylthio, 2-methylpentylthio, 1-methylpentylthio, 3,3-dimethylbutylthio, 2,2-dimethylbutylthio, 1,1, -dimethylbutylthio, 1,2 A straight-chain or branched-chain alkylthio group having 1 to 6 carbon atoms, such as -dimethylbutylthio, 1,3-dimethylbutylthio, 2,3-dimethylbutylthio, and 2-ethylbutylthio. Preferably, it is a straight-chain or branched-chain alkylthio group having 1 to 3 carbon atoms (C1 to C3 alkylthio group), more preferably a methylthio group or an ethylthio group.

【００１８】本明細書において「１乃至４個のハロゲン
原子により置換されたＣ１〜Ｃ６アルキルチオ基」と
は、例えば、クロルメチルチオ、ジクロルメチルチオ、
トリクロルメチルチオ、1-クロルエチルチオ、2-クロル
エチルチオ、1-クロルプロピルチオ、フルオロメチルチ
オ、ジフルオロメチルチオ、トリフルオロメチルチオ、
1-フルオロエチルチオ、2-フルオロエチルチオ、フルオ
ロクロルメチルチオ、ブロモメチルチオのような、同一
又は異なった前記「ハロゲン原子」が１乃至４個前記
「Ｃ１〜Ｃ６アルキルチオ基」に結合した基である。好
適には、フルオロメチルチオ基、クロロメチルチオ基又
はトリフルオロメチルチオ基であり、更に好適には、ト
リフルオロメチルチオ基である。In the present specification, "C1-C6 alkylthio group substituted by 1 to 4 halogen atoms" means, for example, chloromethylthio, dichloromethylthio,
Trichloromethylthio, 1-chloroethylthio, 2-chloroethylthio, 1-chloropropylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio,
A group in which 1 to 4 identical or different “halogen atoms” are bonded to the “C1 to C6 alkylthio group”, such as 1-fluoroethylthio, 2-fluoroethylthio, fluorochloromethylthio, and bromomethylthio. . It is preferably a fluoromethylthio group, a chloromethylthio group or a trifluoromethylthio group, and more preferably a trifluoromethylthio group.

【００１９】本明細書において、「Ｃ２〜Ｃ６アルケニ
ル基」とは、例えば、ビニル、2-プロペニル、1-メチル
-2- プロペニル、2-メチル-2- プロペニル、2-エチル-2
- プロペニル、2-ブテニル、1-メチル-2- ブテニル、2-
メチル-2- ブテニル、1-エチル-2- ブテニル、3-ブテニ
ル、1-メチル-3- ブテニル、2-メチル-3- ブテニル、1-
エチル-3- ブテニル、2-ペンテニル、1-メチル-2- ペン
テニル、2-メチル-2-ペンテニル、3-ペンテニル、1-メ
チル-3- ペンテニル、2-メチル-3- ペンテニル、4-ペン
テニル、1-メチル-4- ペンテニル、2-メチル-4- ペンテ
ニル、2-ヘキセニル、3-ヘキセニル、4-ヘキセニル、5-
ヘキセニルのような、炭素数２乃至６個の直鎖又は分枝
鎖アルケニル基である。好適には、炭素数２乃至５個の
直鎖又は分枝鎖アルケニル基であり、更に好適には、2-
プロペニル基である。In the present specification, "C2-C6 alkenyl group" means, for example, vinyl, 2-propenyl, 1-methyl
2-propenyl, 2-methyl-2-propenyl, 2-ethyl-2
-Propenyl, 2-butenyl, 1-methyl-2-butenyl, 2-
Methyl-2-butenyl, 1-ethyl-2-butenyl, 3-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 1-
Ethyl-3-butenyl, 2-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 4-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-
It is a straight or branched alkenyl group having 2 to 6 carbon atoms such as hexenyl. Preferably, it is a straight-chain or branched alkenyl group having 2 to 5 carbon atoms, more preferably 2-
It is a propenyl group.

【００２０】本明細書において、「１乃至４個のハロゲ
ン原子により置換されたＣ２〜Ｃ６アルケニル基」と
は、例えば、2-クロロビニル、3-クロロ-2- プロペニ
ル、2,2-ジブロモビニル、2,2-ジクロロビニルのよう
な、同一又は異なった前記「ハロゲン原子」が１乃至４
個前記「Ｃ２〜Ｃ６アルケニル基」に結合した基であ
る。好適には、１乃至３個のハロゲン原子により置換さ
れた炭素数２乃至４個のアルケニル基であり、更に好適
には、2-クロロビニル基、3-クロロ-2- プロペニル基で
ある。In the present specification, "C2-C6 alkenyl group substituted by 1 to 4 halogen atoms" means, for example, 2-chlorovinyl, 3-chloro-2-propenyl, 2,2-dibromovinyl The same or different "halogen atoms", such as 1,2,2-dichlorovinyl,
This is a group bonded to the above “C2-C6 alkenyl group”. Preferably, it is an alkenyl group having 2 to 4 carbon atoms substituted by 1 to 3 halogen atoms, and more preferably, a 2-chlorovinyl group or a 3-chloro-2-propenyl group.

【００２１】本明細書において、「Ｃ２〜Ｃ６アルキニ
ル基」とは、例えばエチニル、2-プロピニル、1-メチル
-2- プロピニル、2-メチル-2- プロピニル、2-エチル-2
- プロピニル、2-ブチニル、1-メチル-2- ブチニル、2-
メチル-2- ブチニル、1-エチル-2- ブチニル、3-ブチニ
ル、1-メチル-3- ブチニル、2-メチル-3- ブチニル、1-
エチル-3- ブチニル、2-ペンチニル、1-メチル-2- ペン
チニル、2-メチル-2-ペンチニル、3-ペンチニル、1-メ
チル-3- ペンチニル、2-メチル-3- ペンチニル、4-ペン
チニル、1-メチル-4- ペンチニル、2-メチル-4- ペンチ
ニル、2-ヘキシニル、3-ヘキシニル、4-ヘキシニル、5-
ヘキシニルのような、炭素数２乃至６個の直鎖又は分枝
鎖アルキニル基である。好適には、炭素数３乃至５個の
直鎖又は分枝鎖アルキニル基（Ｃ３〜Ｃ５アルキニル
基）であり、更に好適には、2-プロピニル基である。In the present specification, "C2-C6 alkynyl group" means, for example, ethynyl, 2-propynyl, 1-methyl
2-propynyl, 2-methyl-2-propynyl, 2-ethyl-2
-Propynyl, 2-butynyl, 1-methyl-2-butynyl, 2-
Methyl-2-butynyl, 1-ethyl-2-butynyl, 3-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-
Ethyl-3-butynyl, 2-pentynyl, 1-methyl-2-pentynyl, 2-methyl-2-pentynyl, 3-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl, 4-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-
It is a linear or branched alkynyl group having 2 to 6 carbon atoms such as hexynyl. Preferably, it is a straight-chain or branched-chain alkynyl group having 3 to 5 carbon atoms (C3-C5 alkynyl group), more preferably a 2-propynyl group.

【００２２】本明細書において、「１乃至４個のハロゲ
ン原子により置換されたＣ２〜Ｃ６アルキニル基」と
は、同一又は異なった前記「ハロゲン原子」が１乃至４
個前記「Ｃ２〜Ｃ６アルキニル基」に結合した基であ
る。好適には、１乃至２個のハロゲン原子により置換さ
れた炭素数３乃至５個のアルキニル基であり、更に好適
には、1-クロロ-2- プロピニル基である。In the present specification, the “C2 to C6 alkynyl group substituted by 1 to 4 halogen atoms” means that the same or different “halogen atom” is 1 to 4
It is a group bonded to the above “C2-C6 alkynyl group”. Preferably, it is an alkynyl group having 3 to 5 carbon atoms, which is substituted by one or two halogen atoms, and more preferably, a 1-chloro-2-propynyl group.

【００２３】本明細書において「Ｃ６〜Ｃ１４アリール
基」とは、例えば、フェニル、ナフチルのような、炭素
数６乃至１４個のアリール基である。好適には、フェニ
ル基である。In the present specification, the "C6-C14 aryl group" is an aryl group having 6 to 14 carbon atoms, such as phenyl and naphthyl. Preferably, it is a phenyl group.

【００２４】本明細書において「１乃至３個のＣ１〜Ｃ
６アルキル基により置換されたＣ６〜Ｃ１４アリール
基」とは、例えば、2-メチルフェニル、3-メチルフェニ
ル、4-メチルフェニル、2-エチルフェニル、3-エチルフ
ェニル、4-エチルフェニル、4-イソプロピルフェニル、
4-t-ブチルフェニル、2,4-ジメチルフェニル、3,5-ジメ
チルフェニルのような、同一又は異なった前記「Ｃ１〜
Ｃ６アルキル基」が１乃至３個前記「Ｃ６〜Ｃ１４アリ
ール基」に結合した基である。In this specification, "1 to 3 C1 to C
"C6-C14 aryl group substituted by 6 alkyl groups" means, for example, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 4-ethylphenyl, Isopropylphenyl,
The same or different “C1 to C4” such as 4-t-butylphenyl, 2,4-dimethylphenyl, 3,5-dimethylphenyl
A C6 alkyl group is a group in which 1 to 3 C6 to C14 aryl groups are bonded.

【００２５】本明細書において「１乃至３個のＣ１〜Ｃ
６アルコキシ基により置換されたＣ６〜Ｃ１４アリール
基」とは、例えば、2-メトキシフェニル、3-メトキシフ
ェニル、4-メトキシフェニル、2-エトキシフェニル、3-
エトキシフェニル、4-エトキシフェニル、4-イソプロポ
キシフェニル、2,4-ジメトキシフェニル、3,5-ジメトキ
シフェニルのような、同一又は異なった前記「Ｃ１〜Ｃ
６アルコキシ基」が１乃至３個前記「Ｃ６〜Ｃ１４アリ
ール基」に結合した基である。In this specification, "1 to 3 C1 to C
A C6-C14 aryl group substituted by a 6 alkoxy group "is, for example, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 3-ethoxyphenyl,
The same or different “C1-C4” such as ethoxyphenyl, 4-ethoxyphenyl, 4-isopropoxyphenyl, 2,4-dimethoxyphenyl, 3,5-dimethoxyphenyl
"6 alkoxy groups" are groups in which 1 to 3 carbon atoms are bonded to the "C6-C14 aryl group".

【００２６】本明細書において「１乃至４個のハロゲン
原子により置換されたＣ６〜Ｃ１４アリール基」とは、
例えば、2-クロロフェニル、3-クロロフェニル、4-クロ
ロフェニル、2-フルオロフェニル、3-フルオロフェニ
ル、4-フルオロフェニル、2-ブロモフェニル、2,4-ジク
ロロフェニル、2,4-ジフロオロフェニルのような、同一
又は異なった前記「ハロゲン原子」が１乃至４個前記
「Ｃ６〜Ｃ１４アリール基」に結合した基である。As used herein, the term “C6-C14 aryl group substituted by 1 to 4 halogen atoms”
For example, such as 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-bromophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl A group in which 1 to 4 identical or different “halogen atoms” are bonded to the “C6-C14 aryl group”.

【００２７】本明細書において「Ｃ７〜Ｃ１１アラルキ
ル基」とは、例えば、ベンジル、α−メチルベンジル、
α，α−ジメチルベンジル、フェネチル、フェニルプロ
ピル、ナフチルメチル、ナフチルエチルのような、前記
「アリール基」が１個前記「Ｃ１〜Ｃ６アルキル基」に
置換した基である。好適には、ベンジル基、フェネチル
基である。In the present specification, "C7-C11 aralkyl group" means, for example, benzyl, α-methylbenzyl,
α, α-dimethylbenzyl, phenethyl, phenylpropyl, naphthylmethyl, naphthylethyl, a group in which one of the above “aryl groups” is substituted by the above “C1-C6 alkyl group”. Preferably, they are a benzyl group and a phenethyl group.

【００２８】本明細書において、「１乃至４個のハロゲ
ン原子により置換されたＣ７〜Ｃ１１アラルキル基」と
は、前記「ハロゲン原子」が１乃至４個前記「Ｃ７〜Ｃ
１１アラルキル基」に結合した基である。In the present specification, the “C7-C11 aralkyl group substituted by 1 to 4 halogen atoms” means “1 to 4 halogen atoms” and “C7 to C11 aralkyl groups”.
11 aralkyl group ".

【００２９】本明細書において、「少なくとも１個の酸
素原子、硫黄原子若しくは窒素原子を含み環原子数が４
乃至１０である複素環基（当該複素環基は、１乃至３個
のＣ１〜Ｃ６アルキル基、１乃至３個のＣ１〜Ｃ６アル
コキシ基又は１乃至４個のハロゲン原子により置換され
ても良く、又、ベンゼン環と縮合していても良い）」と
は、例えば、オキシラニル、オキセタニル、アジリジニ
ル、アゼチジニル、チイラニル、チエタニル、(2,2- ジ
メチル)-1,3-ジオキサニル、フリル、チエニル、ピロリ
ル、チアゾリル、イソチアゾリル、オキサゾリル、イソ
オキサゾリル、イミダゾリル、ピラゾリル、ピラニル、
ピラジニル、ピリジル、ピリダジニル、ピリミジニル、
ベンゾフラニル、ベンゾチオフェニル、ベンゾチアゾリ
ル、ベンゾオキサゾリル、インドリル、キノリル、イソ
キノリル、キナゾリル、キノキサリニル、ナフチリジニ
ル、キサンテニル、テトラヒドロフラニル、テトラヒド
ロチエニル、ピロリジニル、チアゾリジニル、イミダゾ
リジニル、イミダゾリニル、オキサゾリニル、ピラゾリ
ジニル、ピペラジニル、テトラヒドロピリミジニル、モ
ルホリニル、インドリニル、テトラヒドロキノリル、ピ
ロリドニル、ピペリドニル、1,3-ジメチル-4- ピラジニ
ル、3,5-ジメチル-4- イソオキサゾリル、6-クロロピリ
ダジニルのような、不飽和又は部分的若しくは完全に飽
和された基である。好適には、チエニル基、ピリジル基
である。As used herein, the term "4 or more ring atoms containing at least one oxygen, sulfur or nitrogen atom"
To 10 heterocyclic groups (the heterocyclic groups may be substituted by 1 to 3 C1 to C6 alkyl groups, 1 to 3 C1 to C6 alkoxy groups, or 1 to 4 halogen atoms, Also, it may be condensed with a benzene ring) '', for example, oxiranyl, oxetanyl, aziridinyl, azetidinyl, thiyanyl, thietanyl, (2,2-dimethyl) -1,3-dioxanyl, furyl, thienyl, pyrrolyl, Thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, pyranyl,
Pyrazinyl, pyridyl, pyridazinyl, pyrimidinyl,
Benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, indolyl, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, naphthyridinyl, xanthenyl, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, thiazolidinyl, imidazolidinyl, imidazolinyl, pyrazolidinyl, pyrazolidinyl, pyrazolidinyl, pyrazolidinyl, pyrazolidinyl Unsaturated or partially or completely, such as morpholinyl, indolinyl, tetrahydroquinolyl, pyrrolidonyl, piperidonyl, 1,3-dimethyl-4-pyrazinyl, 3,5-dimethyl-4-isoxazolyl, 6-chloropyridazinyl Is a group saturated with Preferably, they are a thienyl group and a pyridyl group.

【００３０】本発明の化合物（Ｉ）は、例えば、硫酸
塩、塩酸塩、硝酸塩、りん酸塩のような塩にすることが
できる。それら塩は、農園芸用の除草剤として使用でき
るかぎり、本発明に包含される。The compound (I) of the present invention can be converted into salts such as, for example, sulfates, hydrochlorides, nitrates and phosphates. These salts are included in the present invention as long as they can be used as agricultural and horticultural herbicides.

【００３１】本発明化合物の水和物も、本発明に包含さ
れるものである。Hydrates of the compound of the present invention are also included in the present invention.

【００３２】本発明化合物中には、不斉炭素を有する化
合物もあり、その場合には、本願発明は、一種の光学活
性体及び数種の光学活性体の任意の割合の混合物をも包
含する。Some of the compounds of the present invention have an asymmetric carbon, and in such a case, the present invention includes a mixture of one kind of optically active substance and several kinds of optically active substances at an arbitrary ratio. .

【００３３】上記一般式（Ｉ）において、Ｒ¹ は、好適
には、Ｃ１〜Ｃ６アルキル基（当該アルキル基は、Ｃ１
〜Ｃ６アルコキシ基又は１乃至４個のハロゲン原子によ
り置換されても良い）、Ｃ３〜Ｃ６シクロアルキル基又
はＣ１〜Ｃ６アルコキシ基（当該アルコキシ基は、１乃
至４個のハロゲン原子により置換されても良い）であ
り、より好適には、Ｃ１〜Ｃ６アルキル基（当該アルキ
ル基は、Ｃ１〜Ｃ６アルコキシ基又は１乃至４個のハロ
ゲン原子により置換されても良い）又はＣ１〜Ｃ６アル
コキシ基であり、更に好適には、Ｃ１〜Ｃ３アルキル基
（当該アルキル基は、Ｃ１〜Ｃ３アルコキシ基により置
換されても良い）又はＣ１〜Ｃ３アルコキシ基であり、
より更に好適には、メチル基又はメトキシ基であり、最
も好適には、メトキシ基である。In the general formula (I), R ¹ is preferably a C1-C6 alkyl group (the alkyl group is
To C6 alkoxy group or 1 to 4 halogen atoms), C3 to C6 cycloalkyl group or C1 to C6 alkoxy group (the alkoxy group may be substituted by 1 to 4 halogen atoms). Good), more preferably a C1-C6 alkyl group (the alkyl group may be substituted by a C1-C6 alkoxy group or 1-4 halogen atoms) or a C1-C6 alkoxy group, More preferably, it is a C1-C3 alkyl group (the alkyl group may be substituted by a C1-C3 alkoxy group) or a C1-C3 alkoxy group,
Even more preferably, it is a methyl group or a methoxy group, most preferably a methoxy group.

【００３４】上記一般式（Ｉ）において、Ｒ² は、好適
には、水素原子、Ｃ１〜Ｃ６アルキル基（当該アルキル
基は、水酸基又は１乃至４個のハロゲン原子により置換
されても良い）、Ｃ３〜Ｃ６シクロアルキル基又は式−
ＹＲ⁷ で表される基であり、より好適には、水素原子、
Ｃ１〜Ｃ６アルキル基（当該アルキル基は、水酸基によ
り置換されても良い）又は式−ＹＲ⁷ で表される基であ
り、更に好適には、水素原子、水酸基により置換された
Ｃ１〜Ｃ３アルキル基又は式−ＹＲ⁷ で表される基であ
り、より更に好適には、水素原子、ヒドロキシメチル基
又は式−ＹＲ⁷ で表される基であり、最も好適には、水
素原子である。In the above general formula (I), R ² is preferably a hydrogen atom, a C1-C6 alkyl group (the alkyl group may be substituted by a hydroxyl group or 1 to 4 halogen atoms), A C3-C6 cycloalkyl group or a formula-
A group represented by YR ^7, more preferably a hydrogen atom,
C1~C6 alkyl group (said alkyl group is substituted by a hydroxyl group may also be) a group or the formula -YR ^7, more preferably a hydrogen atom, C1 to C3 alkyl group substituted by a hydroxyl group Or a group represented by the formula -YR ⁷ , more preferably a hydrogen atom, a hydroxymethyl group or a group represented by the formula -YR ⁷ , most preferably a hydrogen atom.

【００３５】Ｒ² が、式−ＹＲ⁷ で表される基である場
合に、（ｉ）Ｙは、好適には、式−ＣＯ−、式−ＣＯＯ
−、式−ＣＨ₂ Ｏ−、式−ＣＨ₂ ＣＨ₂ Ｏ−、式−ＣＨ
₂ ＣＯ−、式−ＣＨ₂ ＣＯＯ−、式−ＣＨ₂ ＣＨ₂ ＣＯ
−、式−ＣＨ₂ ＯＣＯ−、式−ＣＨ₂ ＯＣＯＯ−又は式
−ＣＨ₂ ＣＨ₂ ＯＣＯ−で表される基であり、更に好適
には、式−ＣＯ−、式−ＣＯＯ−、式−ＣＨ₂ Ｏ−、式
−ＣＨ₂ ＣＨ_２Ｏ−、式−ＣＨ_２ＯＣＯ−又は式−Ｃ
Ｈ₂ ＯＣＯＯ−で表される基であり、より更に好適に
は、式−ＣＯ−、式−ＣＯＯ−、式−ＣＨ₂ Ｏ−、式−
ＣＨ₂ ＯＣＯ−又は式−ＣＨ₂ ＯＣＯＯ−で表される基
であり、最も好適には、式−ＣＯ−、式−ＣＯＯ−又は
式−ＣＨ₂ ＯＣＯ−で表される基である。When R ² is a group represented by the formula —YR ⁷ , (i) Y is preferably a group represented by the formula —CO— or the formula —COO.
-, the formula -CH ₂ O-formula -CH ₂ CH ₂ O-formula -CH
₂ CO-, wherein -CH ₂ COO-, wherein -CH ₂ CH ₂ CO
—, A group represented by the formula —CH ₂ OCO—, —CH ₂ OCOO— or —CH ₂ CH ₂ OCO—, and more preferably a formula —CO—, a formula —COO—, or a formula —CH ₂ O—, formula —CH ₂ CH ₂ O—, formula —CH ₂ OCO— or formula —C
A group represented by H ₂ -OCOO-, more preferably more, Formula -CO-, wherein -COO-, wherein -CH ₂ O-formula -
A group represented by CH ₂ OCO— or —CH ₂ OCOO—, and most preferably a group represented by formula —CO—, —COO—, or —CH ₂ OCO—.

【００３６】（ｉｉ）Ｒ⁷ は、好適には、Ｃ１〜Ｃ６ア
ルキル基（当該アルキル基は、Ｃ１〜Ｃ６アルコキシ基
又は１乃至４個のハロゲン原子により置換されても良
い）、Ｃ３〜Ｃ６シクロアルキル基、Ｃ２〜Ｃ６アルケ
ニル基（当該アルケニル基は、１乃至４個のハロゲン原
子により置換されても良い）、Ｃ２〜Ｃ６アルキニル基
（当該アルキニル基は、１乃至４個のハロゲン原子によ
り置換されても良い）、Ｃ６〜Ｃ１４アリール基（当該
アリール基は、１乃至３個のＣ１〜Ｃ６アルキル基、１
乃至３個のＣ１〜Ｃ６アルコキシ基又は１乃至４個のハ
ロゲン原子により置換されても良い）、Ｃ７〜Ｃ１１ア
ラルキル基（当該アラルキル基は、１乃至４個のハロゲ
ン原子により置換されても良い）又は少なくとも１個の
酸素原子、硫黄原子若しくは窒素原子を含み環原子数が
４乃至１０である複素環基（当該複素環基は、Ｃ１〜Ｃ
６アルキル基、Ｃ１〜Ｃ６アルコキシ基又は１乃至４個
のハロゲン原子により置換されても良く、又、ベンゼン
環と縮合していても良い）であり、より好適には、Ｃ１
〜Ｃ６アルキル基（当該アルキル基は、Ｃ１〜Ｃ６アル
コキシ基又は１乃至４個のハロゲン原子により置換され
ても良い）であり、より更に好適には、Ｃ１〜Ｃ３アル
キル基（当該アルキル基は、１乃至４個のハロゲン原子
により置換されても良い）であり、最も好適には、エチ
ル基又は2,2,2-トリクロロエチル基である。(Ii) R ⁷ is preferably a C1 to C6 alkyl group (the alkyl group may be substituted by a C1 to C6 alkoxy group or 1 to 4 halogen atoms), a C3 to C6 cycloalkyl group. Alkyl group, C2-C6 alkenyl group (the alkenyl group may be substituted by 1 to 4 halogen atoms), C2 to C6 alkynyl group (the alkynyl group is substituted by 1 to 4 halogen atoms) A C6 to C14 aryl group (the aryl group may be one to three C1 to C6 alkyl groups,
3 to 3 C1 to C6 alkoxy groups or 1 to 4 halogen atoms may be substituted), C7 to C11 aralkyl groups (the aralkyl groups may be substituted with 1 to 4 halogen atoms) Or a heterocyclic group containing at least one oxygen atom, sulfur atom or nitrogen atom and having 4 to 10 ring atoms (the heterocyclic group is a C1 to C
6 alkyl groups, C1 to C6 alkoxy groups or 1 to 4 halogen atoms, or may be condensed with a benzene ring), and more preferably C1
To C6 alkyl group (the alkyl group may be substituted by a C1 to C6 alkoxy group or 1 to 4 halogen atoms), and more preferably, a C1 to C3 alkyl group (the alkyl group is (Which may be substituted by 1 to 4 halogen atoms), and most preferably an ethyl group or a 2,2,2-trichloroethyl group.

【００３７】上記一般式（Ｉ）において、Ｒ³ は、好適
には、Ｃ１〜Ｃ６アルキル基（当該アルキル基は、Ｃ１
〜Ｃ６アルコキシ基又は１乃至４個のハロゲン原子によ
り置換されても良い）、Ｃ３〜Ｃ６シクロアルキル基Ｃ
１〜Ｃ６アルコキシ基（当該アルコキシ基は、１乃至４
個のハロゲン原子により置換されても良い）、ハロゲン
原子、ニトロ基又は式−ＣＯＲ⁸ で表される基であり、
より好適には、Ｃ１〜Ｃ６アルキル基（当該アルキル基
は、Ｃ１〜Ｃ６アルコキシ基又は１乃至４個のハロゲン
原子により置換されても良い）、Ｃ１〜Ｃ６アルコキシ
基（当該アルコキシ基は、１乃至４個のハロゲン原子に
より置換されても良い）又はハロゲン原子であり、更に
好適には、Ｃ１〜Ｃ３アルキル基、Ｃ１〜Ｃ３アルコキ
シ基又はハロゲン原子であり、より更に好適には、メチ
ル基、エチル基、メトキシ基、エトキシ基、弗素原子又
は塩素原子であり、最も好適には、メチル基である。In the above general formula (I), R ³ is preferably a C1-C6 alkyl group (the alkyl group is
To C6 alkoxy group or 1 to 4 halogen atoms), C3-C6 cycloalkyl group C
1 to C6 alkoxy group (the alkoxy group is 1 to 4
A halogen atom, a nitro group or a group represented by the formula —COR ⁸ ,
More preferably, a C1 to C6 alkyl group (the alkyl group may be substituted by a C1 to C6 alkoxy group or 1 to 4 halogen atoms), a C1 to C6 alkoxy group (the alkoxy group is (Which may be substituted by four halogen atoms) or a halogen atom, more preferably a C1-C3 alkyl group, a C1-C3 alkoxy group or a halogen atom, even more preferably a methyl group, ethyl A methoxy group, an ethoxy group, a fluorine atom or a chlorine atom, and most preferably a methyl group.

【００３８】上記一般式（Ｉ）において、Ｒ³ の置換位
置は、好適には、２位である。In the above general formula (I), the substitution position of R ³ is preferably the 2-position.

【００３９】上記一般式（Ｉ）において、Ｒ⁴ 及びＲ⁵
は、好適には、同一又は異なって水素原子又はメチル基
であり、より好適には、Ｒ⁴ とＲ⁵ が共に水素原子であ
るか又はＲ⁴ がメチル基でＲ⁵ が水素原子であり、最も
好適には、Ｒ⁴ とＲ⁵ が共に水素原子である。In the above general formula (I), R ⁴ and R ⁵
Is preferably the same or different and is a hydrogen atom or a methyl group, more preferably R ⁴ and R ⁵ are both hydrogen atoms, or R ⁴ is a methyl group and R ⁵ is a hydrogen atom, Most preferably, R ⁴ and R ⁵ are both hydrogen atoms.

【００４０】上記一般式（Ｉ）において、Ｒ⁶ は、好適
には、Ｃ１〜Ｃ６アルキル基（当該アルキル基は、Ｃ１
〜Ｃ６アルコキシ基又は１乃至４個のハロゲン原子によ
り置換されても良い）、Ｃ３〜Ｃ６シクロアルキル基、
Ｃ１〜Ｃ６アルコキシ基（当該アルコキシ基は、１乃至
４個のハロゲン原子により置換されても良い）、ハロゲ
ン原子又は式−ＣＯＲ⁸ で表される基であり、より好適
には、Ｃ１〜Ｃ６アルキル基（当該アルキル基は、１乃
至４個のハロゲン原子により置換されても良い）、Ｃ１
〜Ｃ６アルコキシ基（当該アルコキシ基は、１乃至４個
のハロゲン原子により置換されても良い）又はハロゲン
原子であり、更に好適には、Ｃ１〜Ｃ３アルキル基、Ｃ
１〜Ｃ３アルコキシ基又はハロゲン原子であり、より更
に好適には、メトキシ基、弗素原子又は塩素原子であ
り、最も好適には、弗素原子又は塩素原子である。In the above general formula (I), R ⁶ is preferably a C1-C6 alkyl group (the alkyl group is
To C6 alkoxy group or 1 to 4 halogen atoms), C3 to C6 cycloalkyl group,
C1 -C6 alkoxy group (said alkoxy group may be substituted by 1 to 4 halogen atoms), a group represented by halogen atom or formula -COR ^8, more preferably, C1 -C6 alkyl Group (the alkyl group may be substituted by 1 to 4 halogen atoms), C1
To a C6 alkoxy group (the alkoxy group may be substituted by 1 to 4 halogen atoms) or a halogen atom, more preferably a C1 to C3 alkyl group,
It is a 1-C3 alkoxy group or a halogen atom, more preferably a methoxy group, a fluorine atom or a chlorine atom, and most preferably a fluorine atom or a chlorine atom.

【００４１】Ｒ³ 又はＲ⁶ が式−ＣＯＲ⁸ で表される基
である場合において、Ｒ⁸ は、好適には、Ｃ１〜Ｃ３ア
ルキル基又はＣ１〜Ｃ３アルコキシ基であり、さらに好
適には、Ｃ１〜Ｃ３アルコキシ基であり、最も好適に
は、メトキシ基である。When R ³ or R ⁶ is a group represented by the formula —COR ⁸ , R ⁸ is preferably a C 1 -C ³ alkyl group or a C 1 -C ³ alkoxy group, more preferably, It is a C1-C3 alkoxy group, most preferably a methoxy group.

【００４２】上記一般式（Ｉ）において、Ａは、好適に
は、酸素原子である。In the above general formula (I), A is preferably an oxygen atom.

【００４３】上記一般式（Ｉ）において、Ｘは、好適に
は、酸素原子である。In the above general formula (I), X is preferably an oxygen atom.

【００４４】上記一般式（Ｉ）において、Ｑは、好適に
は、硫黄原子である。In the above general formula (I), Q is preferably a sulfur atom.

【００４５】上記一般式（Ｉ）において、ｍは、好適に
は、０、１、２又は３であり、より好適には０又は１で
あり、最も好適には、０である。In the general formula (I), m is preferably 0, 1, 2, or 3, more preferably 0 or 1, and most preferably 0.

【００４６】上記一般式（Ｉ）において、ｎは、好適に
は、０、１、２又は３であり、より好適には０、１又は
２であり、更に好適には、０又は１であり、最も好適に
は、１である。In the above general formula (I), n is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. , Most preferably 1.

【００４７】本発明の代表化合物を下記表１乃至８に例
示するが、本発明はこれらの化合物に限定されるもので
はない。Representative compounds of the present invention are shown in the following Tables 1 to 8, but the present invention is not limited to these compounds.

【００４８】下記表において、「Me」は、メチル基を、
「Et」は、エチル基を、「Pr」は、プロピル基を、「B
u」は、ブチル基を、「Pen 」は、ペンチル基を、「Hex
」は、ヘキシル基を、「Ph」は、フェニル基を、「The
n」は、テノイル基を、「Furo」は、フロイル基を、「P
yra」は、ピラジニル基を、「Tria」は、トリアゾリル
基を、「Isothi」は、イソチアゾリル基を、「Pyrd」
は、ピリダジニル基を、「Pyrim 」は、ピリミジニル基
を、「Pyrr」は、ピロリル基を、「Qui 」は、キノリル
基を、「Isox」は、イソキサゾリル基を、「Pyraz 」
は、ピラゾリル基を、「Nico」は、ニコチノイル基を、
「Isonico 」は、イソニコチノイル基を、「THP 」は、
テトラヒドロピラニル基を、「Benthi」は、ベンゾ
［ｂ］チエニル基を、「i-」は、イソを、「c-」は、シ
クロを、「s-」は、セカンダリーを、「t-」は、ターシ
ャリーを、それぞれ示す。In the following table, “Me” represents a methyl group,
"Et" represents an ethyl group, "Pr" represents a propyl group, "B
“u” represents a butyl group, “Pen” represents a pentyl group, and “Hex
"Represents a hexyl group," Ph "represents a phenyl group, and" The
"n" represents a tenoyl group, "Furo" represents a furoyl group, and "P
"yra" represents a pyrazinyl group, "Tria" represents a triazolyl group, "Isothi" represents an isothiazolyl group, and "Pyrd"
Is a pyridazinyl group, "Pyrim" is a pyrimidinyl group, "Pyrr" is a pyrrolyl group, "Qui" is a quinolyl group, "Isox" is an isoxazolyl group, and "Pyraz"
Is a pyrazolyl group, "Nico" is a nicotinoyl group,
"Isonico" is an isonicotinoyl group, "THP" is
Tetrahydropyranyl group, "Benthi" is benzo [b] thienyl group, "i-" is iso, "c-" is cyclo, "s-" is secondary, "t-" Indicates tertiary, respectively.

【００４９】表中、(R³)n 及び(R⁶)m の欄にH とあるの
は、それぞれｎ及びｍが０である場合を示している。In the table, "H" in the columns of (R ³ ) n and (R ⁶ ) m indicates that n and m are 0, respectively.

【００５０】[0050]

【化３】 Embedded image

【００５１】[0051]

【表１】 ──────────────────────────────────── 番号 R¹ R² (R³)n ACR⁴(R⁵) (R⁶)m X Q 融点（℃） ──────────────────────────────────── A1.1 Me H H OCH₂ H O S 168-170 A1.2 Me H H OCH₂ H O O 146-148 A1.3 Me H H SCH₂ H O S 147-149 A1.4 Me H H SCH₂ H O O A1.5 MeO H H OCH₂ H O S 142-144 A1.6 MeO H H OCH₂ H O O 115-118 A1.7 MeO H H SCH₂ H O S 139-141 A1.8 MeO H H SCH₂ H O O 94-95 A1.9 MeO H H OCH₂ H S S 160-162 A1.10 MeO H H OCH₂ H S O A1.11 MeO H H SCH₂ H S S A1.12 MeO H H SCH₂ H S O A1.13 MeS H H OCH₂ H O S 162-164 A1.14 MeS H H OCH₂ H O O A1.15 MeS H H SCH₂ H O S A1.16 MeS H H OCH₂ H S S 136-138 A1.17 MeS H H OCH₂ H S O A1.18 Et H H OCH₂ H O S 182 A1.19 Et H H SCH₂ H O S A1.20 Et H H OCH₂ H O O A1.21 EtO H H OCH₂ H O S 149-150 A1.22 EtO H H OCH₂ H O O A1.23 nPr H H OCH₂ H O S A1.24 nPr H H SCH₂ H O S A1.25 nPrO H H OCH₂ H O S 159-163 A1.26 iPr H H OCH₂ H O S A1.27 iPr H H SCH₂ H O S A1.28 iPrO H H OCH₂ H O S 176-178 A1.29 nBu H H OCH₂ H O S A1.30 nBu H H SCH₂ H O S A1.31 nBuO H H OCH₂ H O S 149-152 A1.32 tBu H H OCH₂ H O S 156-158 A1.33 tBuO H H OCH₂ H O S A1.34 tBu H H OCH₂ H O O A1.35 tBuO H H OCH₂ H O O A1.36 FCH₂ H H OCH₂ H O S A1.37 FCH₂ H H OCH₂ H O O A1.38 FCH₂ H H SCH₂ H O S A1.39 F₂CH H H OCH₂ H O S A1.40 F₂CH H H OCH₂ H O O A1.41 F₂CH H H SCH₂ H O S A1.42 F₃C H H OCH₂ H O S A1.43 F₃C H H OCH₂ H O O A1.44 F₃C H H SCH₂ H O S A1.45 ClCH₂ H H OCH₂ H O S 196-197 A1.46 ClCH₂ H H OCH₂ H O O A1.47 ClCH₂ H H SCH₂ H O S A1.48 ClCH₂O H H OCH₂ H O S A1.49 Cl₂CH H H OCH₂ H O S A1.50 Cl₂CH H H SCH₂ H O S A1.51 BrCH₂ H H OCH₂ H O S A1.52 BrCH₂ H H SCH₂ H O S A1.53 FClCH H H OCH₂ H O S A1.54 FClCH H H SCH₂ H O S A1.55 ClCH₂O H H OCH₂ H O O A1.56 Cl₃CCH₂O H H OCH₂ H O S 153-154 A1.57 Cl₃CCH₂O H H OCH₂ H O O A1.58 Br(CH₂)₃ H H OCH₂ H O S 163-165 A1.59 Br(CH₂)₃ H H SCH₂ H O S A1.60 Br(CH₂)₄ H H OCH₂ H O S 151-153 A1.61 Br(CH₂)₄ H H SCH₂ H O S A1.62 MeOCH₂ H H OCH₂ H O S 140-143 A1.63 MeOCH₂ H H OCH₂ H O O A1.64 MeOCH₂ H H SCH₂ H O S A1.65 EtOCH₂ H H OCH₂ H O S 118-120 A1.66 EtOCH₂ H H OCH₂ H O O A1.67 EtOCH₂ H H SCH₂ H O S A1.68 nPrOCH₂ H H OCH₂ H O S A1.69 nPrOCH₂ H H SCH₂ H O S A1.70 MeOCH₂CH₂ H H OCH₂ H O S 156-158 A1.71 MeOCH₂CH₂ H H OCH₂ H O O A1.72 MeOCH₂CH₂ H H SCH₂ H O S A1.73 EtOCH₂CH₂ H H OCH₂ H O S A1.74 EtOCH₂CH₂ H H OCH₂ H O O A1.75 EtOCH₂CH₂ H H SCH₂ H O S A1.76 nPrOCH₂CH₂ H H OCH₂ H O S A1.77 nPrOCH₂CH₂ H H OCH₂ H O O ────────────────────────────────────[Table 1] ──────────────────────────────────── Number R ¹ R ² (R ³ ) n ACR ⁴ (R ⁵ ) (R ⁶ ) m XQ Melting point (℃) ────────────────────────────────── ── A1.1 Me HH OCH ₂ HOS 168-170 A1.2 Me HH OCH ₂ HOO 146-148 A1.3 Me HH SCH ₂ HOS 147-149 A1.4 Me HH SCH ₂ HOO A1.5 MeO HH OCH ₂ HOS 142-144 A1.6 MeO HH OCH ₂ HOO 115-118 A1.7 MeO HH SCH ₂ HOS 139-141 A1.8 MeO HH SCH ₂ HOO 94-95 A1.9 MeO HH OCH ₂ HSS 160-162 A1. 10 MeO HH OCH ₂ HSO A1.11 MeO HH SCH ₂ HSS A1.12 MeO HH SCH ₂ HSO A1.13 MeS HH OCH ₂ HOS 162-164 A1.14 MeS HH OCH ₂ HOO A1.15 MeS HH SCH ₂ HOS A1 .16 MeS HH OCH ₂ HSS 136-138 A1.17 MeS HH OCH ₂ HSO A1.18 Et HH OCH ₂ HOS 182 A1.19 Et HH SCH ₂ HOS A1.20 Et HH OCH ₂ HOO A1.21 EtO HH OCH ₂ HOS 149-150 A1.22 EtO HH OCH ₂ HOO A1.23 nPr HH OCH ₂ HOS A1.24 nPr HH SCH ₂ HOS A1.25 nPrO HH OCH ₂ HOS 159-163 A1.26 iPr HH OCH ₂ HOS A1.27 iPr HH SCH ₂ HOS A1 .28 iPrO HH OCH ₂ HOS 176-178 A1.29 nBu HH OCH ₂ HOS A1.30 nBu HH SCH ₂ HOS A1.31 nBuO HH OCH ₂ HOS 149-152 A1.32 tBu HH OCH ₂ HOS 156-158 A1. 33 tBuO HH OCH ₂ HOS A1.34 tBu HH OCH ₂ HOO A1.35 tBuO HH OCH ₂ HOO A1.36 FCH ₂ HH OCH ₂ HOS A1.37 FCH ₂ HH OCH ₂ HOO A1.38 FCH ₂ HH SCH ₂ HOS A1 .39 F ₂ CH HH OCH ₂ HOS A1.40 F ₂ CH HH OCH ₂ HOO A1.41 F ₂ CH HH SCH ₂ HOS A1.42 F ₃ CHH OCH ₂ HOS A1.43 F ₃ CHH OCH ₂ HOO A1.44 F ₃ CHH SCH ₂ HOS A1.45 ClCH ₂ HH OCH ₂ HOS 196-197 A1.46 ClCH ₂ HH OCH ₂ HOO A1.47 ClCH ₂ HH SCH ₂ HOS A1.48 ClCH ₂ OHH OCH ₂ HOS A1.49 Cl ₂ CH HH OCH ₂ HOS A1.50 Cl ₂ CH HH SCH ₂ HOS A1.51 BrCH ₂ HH OCH ₂ HOS A1.52 BrCH ₂ HH SCH ₂ HOS A1.53 FClCH HH OCH ₂ HOS A1.54 FClCH HH SCH ₂ HOS A1 .55 ClCH ₂ OHH OCH ₂ HOO A1.56 Cl ₃ CCH ₂ OHH OCH ₂ HOS 153-154 A1.57 Cl ₃ CCH ₂ OHH OCH ₂ HOO A1.58 Br (CH ₂ ) ₃ HH OCH ₂ HOS 163-165 A1 .59 Br (CH ₂ ) ₃ HH SCH ₂ HOS A1.60 Br (CH ₂ ) ₄ HH OCH ₂ HOS 151-153 A1.61 Br (CH ₂ ) ₄ HH SCH ₂ HOS A1.62 MeOCH ₂ HH OCH ₂ HOS 140-143 A1.63 MeOCH ₂ HH OCH ₂ H OO A1.64 MeOCH ₂ HH SCH ₂ HOS A1.65 EtOCH ₂ HH OCH ₂ HOS 118-120 A1.66 EtOCH ₂ HH OCH ₂ HOO A1.67 EtOCH ₂ HH SCH ₂ HOS A1.68 nPrOCH ₂ HH OCH ₂ HOS A1 .69 nPrOCH ₂ HH SCH ₂ HOS A1.70 MeOCH ₂ CH ₂ HH OCH ₂ HOS 156-158 A1.71 MeOCH ₂ CH ₂ HH OCH ₂ HOO A1.72 MeOCH ₂ CH ₂ HH SCH ₂ HOS A1.73 EtOCH ₂ CH ₂ HH OCH ₂ HOS A1.74 EtOCH ₂ CH ₂ HH OCH ₂ HOO A1.75 EtOCH ₂ CH ₂ HH SCH ₂ HOS A1.76 nPrOCH ₂ CH ₂ HH OCH ₂ HOS A1.77 nPrOCH ₂ CH ₂ HH OCH ₂ HOO ─ ───────────────────────────────────

【００５２】[0052]

【表２】 ──────────────────────────────────── 番号 R¹ R² (R³)n ACR⁴(R⁵) (R⁶)m X Q 融点（℃） ──────────────────────────────────── B1.1 Me Me H OCH₂ H O S 119-120 B1.2 Me Me H SCH₂ H O S B1.3 MeO Me H OCH₂ H O S 85-87 B1.4 Me Me H OCH₂ H O O B1.5 MeO Me H OCH₂ H O O 76-78 B1.6 Me Et H OCH₂ H O S B1.7 MeO Et H OCH₂ H O S B1.8 Me Et H SCH₂ H O S B1.9 Me Et H OCH₂ H O O B1.10 MeO Et H OCH₂ H O O 油状物 B1.11 Me iPr H OCH₂ H O S B1.12 MeO iPr H OCH₂ H O S B1.13 Me iPr H OCH₂ H O O B1.14 MeO iPr H OCH₂ H O O B1.15 Et Me H OCH₂ H O S B1.16 Et Et H OCH₂ H O S B1.17 nPr Et H OCH₂ H O S B1.18 nBu Et H OCH₂ H O S B1.19 iPr Et H OCH₂ H O S B1.20 FCH₂ Et H OCH₂ H O S B1.21 F₂CH Et H OCH₂ H O S B1.22 F₃C Et H OCH₂ H O S B1.23 ClCH₂ Et H OCH₂ H O S B1.24 Cl₂CH Et H OCH₂ H O S B1.25 BrCH₂ Et H OCH₂ H O S B1.26 FClCH Et H OCH₂ H O S B1.27 MeOCH₂ Et H OCH₂ H O S B1.28 EtOCH₂ Et H OCH₂ H O S B1.29 nPrOCH₂ Et H OCH₂ H O S B1.30 MeOCH₂CH₂ Et H OCH₂ H O S B1.31 EtOCH₂CH₂ Et H OCH₂ H O S B1.32 Me nPr H OCH₂ H O S B1.33 Me nPr H SCH₂ H O S B1.34 Et nPr H OCH₂ H O S B1.35 nPr nPr H OCH₂ H O S B1.36 nBu nPr H OCH₂ H O S B1.37 iPr nPr H OCH₂ H O S B1.38 FCH₂ nPr H OCH₂ H O S B1.39 F₂CH nPr H OCH₂ H O S B1.40 F₃C nPr H OCH₂ H O S B1.41 ClCH₂ nPr H OCH₂ H O S B1.42 Cl₂CH nPr H OCH₂ H O S B1.43 BrCH₂ nPr H OCH₂ H O S B1.44 FClCH nPr H OCH₂ H O S B1.45 MeOCH₂ nPr H OCH₂ H O S B1.46 EtOCH₂ nPr H OCH₂ H O S B1.47 nPrOCH₂ nPr H OCH₂ H O S B1.48 MeOCH₂CH₂ nPr H OCH₂ H O S B1.49 EtOCH₂CH₂ nPr H OCH₂ H O S B1.50 Me nBu H OCH₂ H O S B1.51 Et nBu H OCH₂ H O S B1.52 nPr nBu H OCH₂ H O S B1.53 nBu nBu H OCH₂ H O S B1.54 iPr nBu H OCH₂ H O S B1.55 FCH₂ nBu H OCH₂ H O S B1.56 F₂CH nBu H OCH₂ H O S B1.57 F₃C nBu H OCH₂ H O S B1.58 ClCH₂ nBu H OCH₂ H O S B1.59 Cl₂CH nBu H OCH₂ H O S B1.60 BrCH₂ nBu H OCH₂ H O S B1.61 FClCH nBu H OCH₂ H O S B1.62 MeOCH₂ nBu H OCH₂ H O S B1.63 EtOCH₂ nBu H OCH₂ H O S B1.64 nPrOCH₂ nBu H OCH₂ H O S B1.65 MeOCH₂CH₂ nBu H OCH₂ H O S B1.66 EtOCH₂CH₂ nBu H OCH₂ H O S B1.67 Et iPr H OCH₂ H O S B1.68 nPr iPr H OCH₂ H O S B1.69 nBu iPr H OCH₂ H O S B1.70 iPr iPr H OCH₂ H O S B1.71 FCH₂ iPr H OCH₂ H O S B1.72 F₂CH iPr H OCH₂ H O S B1.73 F₃C iPr H OCH₂ H O S B1.74 ClCH₂ iPr H OCH₂ H O S B1.75 Cl₂CH iPr H OCH₂ H O S B1.76 BrCH₂ iPr H OCH₂ H O S B1.77 FClCH iPr H OCH₂ H O S B1.78 MeOCH₂ iPr H OCH₂ H O S B1.79 EtOCH₂ iPr H OCH₂ H O S B1.80 nPrOCH₂ iPr H OCH₂ H O S B1.81 MeOCH₂CH₂ iPr H OCH₂ H O S B1.82 EtOCH₂CH₂ iPr H OCH₂ H O S B2.1 F₂CH COOMe H OCH₂ H O S B2.2 F₃C COOMe H OCH₂ H O S B2.3 ClCH₂ COOMe H OCH₂ H O S B2.4 BrCH₂ COOMe H OCH₂ H O S B2.5 FClCH COOMe H OCH₂ H O S B2.6 EtOCH₂ COOMe H OCH₂ H O S B2.7 iPr COOEt H OCH₂ H O S B2.8 FCH₂ COOEt H OCH₂ H O S B2.9 F₂CH COOEt H OCH₂ H O S B2.10 F₃C COOEt H OCH₂ H O S B2.11 ClCH₂ COOEt H OCH₂ H O S B2.12 Cl₂CH COOEt H OCH₂ H O S B2.13 BrCH₂ COOEt H OCH₂ H O S B2.14 FClCH COOEt H OCH₂ H O S B2.15 MeOCH₂ COOEt H OCH₂ H O S B2.16 EtOCH₂ COOEt H OCH₂ H O S B2.17 nPrOCH₂ COOEt H OCH₂ H O S B2.18 MeOCH₂CH₂ COOEt H OCH₂ H O S B2.19 EtOCH₂CH₂ COOEt H OCH₂ H O S B2.20 nPr Me H OCH₂ H O S B2.21 iPr Me H OCH₂ H O S B2.22 nBu Me H OCH₂ H O S B2.23 tBu Me H OCH₂ H O S B2.24 FCH₂ Me H OCH₂ H O S B2.25 F₂CH Me H OCH₂ H O S B2.26 CF₃ Me H OCH₂ H O S B2.27 ClCH₂ Me H OCH₂ H O S B2.28 Cl₂CH Me H OCH₂ H O S B2.29 BrCH₂ Me H OCH₂ H O S B2.30 FClCH Me H OCH₂ H O S B2.31 MeOCH₂ Me H OCH₂ H O S B2.32 EtOCH₂ Me H OCH₂ H O S B2.33 nPrOCH₂ Me H OCH₂ H O S B2.34 MeOCH₂CH₂ Me H OCH₂ H O S B2.35 EtOCH₂CH₂ Me H OCH₂ H O S B2.36 Me CH₂CH=CH₂ H OCH₂ H O O B2.37 MeO CH₂CH=CH₂ H OCH₂ H O O 油状物 B2.38 MeO COMe H OCH₂ H O S B2.39 MeO COMe H SCH₂ H O S B2.40 MeO COMe H OCH₂ H O O B2.41 MeO COEt H OCH₂ H O S B2.42 MeO COEt H OCH₂ H O O B2.43 MeO COnPr H OCH₂ H O S B2.44 MeO COnPr H OCH₂ H O O B2.45 MeO COiPr H OCH₂ H O S B2.46 MeO COiPr H OCH₂ H O O B2.47 MeO COnBu H OCH₂ H O S B2.48 MeO COnBu H OCH₂ H O O B2.49 MeO COiBu H OCH₂ H O S B2.50 MeO COiBu H OCH₂ H O O B2.51 MeO COtBu H OCH₂ H O S B2.52 MeO COtBu H OCH₂ H O O B2.53 FCH₂ COOMe H OCH₂ H O S B2.54 Cl₂CH COOMe H OCH₂ H O S B2.55 Cl₃CCH₂O COOMe H OCH₂ H O S B2.56 Cl₃CCH₂O COOMe H OCH₂ H O O B2.57 MeOCH₂ COOMe H OCH₂ H O S B2.58 MeOCH₂ COOMe H OCH₂ H O O B2.59 EtOCH₂ COCH₂OEt H OCH₂ H O S B2.60 MeO COCH₂OnPr H OCH₂ H O S B2.61 MeO CO(CH₂)₂OMe H OCH₂ H O S B2.62 MeO CO(CH₂)₂OEt H OCH₂ H O S B2.63 Me COOEt H OCH₂ H O S 155-160 B2.64 Me COOEt H SCH₂ H O S B2.65 Et COOEt H OCH₂ H O S B2.66 nPr COOEt H OCH₂ H O S B2.67 nBu COOEt H OCH₂ H O S ────────────────────────────────────[Table 2] No. R ¹ R ² (R ³ ) n ACR ⁴ (R ⁵ ) (R ⁶ ) m XQ Melting point (℃) ────────────────────────────────── ── B1.1 Me Me H OCH ₂ HOS 119-120 B1.2 Me Me H SCH ₂ HOS B1.3 MeO Me H OCH ₂ HOS 85-87 B1.4 Me Me H OCH ₂ HOO B1.5 MeO Me H OCH ₂ HOO 76-78 B1.6 Me Et H OCH ₂ HOS B1.7 MeO Et H OCH ₂ HOS B1.8 Me Et H SCH ₂ HOS B1.9 Me Et H OCH ₂ HOO B1.10 MeO Et H OCH ₂ HOO Oil B1.11 Me iPr H OCH ₂ HOS B1.12 MeO iPr H OCH ₂ HOS B1.13 Me iPr H OCH ₂ HOO B1.14 MeO iPr H OCH ₂ HOO B1.15 Et Me H OCH ₂ HOS B1. 16 Et Et H OCH ₂ HOS B1.17 nPr Et H OCH ₂ HOS B1.18 nBu Et H OCH ₂ HOS B1.19 iPr Et H OCH ₂ HOS B1.20 FCH ₂ Et H OCH ₂ HOS B1.21 F ₂ CH Et H OCH ₂ HOS B1.22 F ₃ C Et H OCH ₂ HOS B1.23 ClCH ₂ Et H OCH ₂ HOS B1.24 Cl ₂ CH Et H OCH ₂ HOS B1.25 BrCH ₂ Et H OCH ₂ HOS B1.26 FClCH Et H OCH ₂ HOS B1.27 MeOCH ₂ Et H OCH ₂ HOS B1.28 EtOCH ₂ Et H OCH ₂ HOS B1.29 nPrOCH ₂ Et H OCH ₂ HOS B1.30 MeOCH ₂ CH ₂ Et H OCH ₂ HOS B1.31 EtOCH ₂ CH ₂ Et H OCH ₂ HOS B1.32 Me nPr H OCH ₂ HOS B1.33 Me nPr H SCH ₂ HOS B1.34 Et nPr H OCH ₂ HOS B1.35 nPr nPr H OCH ₂ HOS B1.36 nBu nPr H OCH ₂ HOS B1.37 iPr nPr H OCH ₂ HOS B1.38 FCH ₂ nPr H OCH ₂ HOS B1.39 F ₂ CH nPr H OCH ₂ HOS B1.40 F ₃ C nPr H OCH ₂ HOS B1.41 ClCH ₂ nPr H OCH ₂ HOS B1.42 Cl ₂ CH nPr H OCH ₂ HOS B1.43 BrCH ₂ nPr H OCH ₂ HOS B1.44 FClCH nPr H OCH ₂ HOS B1.45 MeOCH ₂ nPr H OCH ₂ HOS B1.46 EtOCH ₂ nPr H OCH ₂ HOS B1.47 nPrOCH ₂ nPr H OCH ₂ HOS B1.48 MeOCH ₂ CH ₂ nPr H OCH ₂ HOS B1.49 EtOCH ₂ CH ₂ nPr H OCH ₂ HOS B1.50 Me nBu H OCH ₂ HOS B1.51 Et nBu H OCH ₂ HOS B1.52 nPr nBu H OCH ₂ HOS B1.53 nBu nBu H OCH ₂ HOS B1.54 iPr nBu H OCH ₂ HOS B1.55 FCH ₂ nBu H OCH ₂ HOS B1.56 F ₂ CH nBu H OCH ₂ HOS B1.57 F ₃ C nBu H OCH ₂ HOS B1.58 ClCH ₂ nBu H OCH ₂ HOS B1.59 Cl ₂ CH nBu H OCH ₂ HOS B1.60 BrCH ₂ nBu H OCH ₂ HOS B1.61 FClCH nBu H OCH ₂ HOS B1.62 MeOCH ₂ nBu H OC H ₂ HOS B1.63 EtOCH ₂ nBu H OCH ₂ HOS B1.64 nPrOCH ₂ nBu H OCH ₂ HOS B1.65 MeOCH ₂ CH ₂ nBu H OCH ₂ HOS B1.66 EtOCH ₂ CH ₂ nBu H OCH ₂ HOS B1.67 Et iPr H OCH ₂ HOS B1.68 nPr iPr H OCH ₂ HOS B1.69 nBu iPr H OCH ₂ HOS B1.70 iPr iPr H OCH ₂ HOS B1.71 FCH ₂ iPr H OCH ₂ HOS B1.72 F ₂ CH iPr H OCH ₂ HOS B1.73 F ₃ C iPr H OCH ₂ HOS B1.74 ClCH ₂ iPr H OCH ₂ HOS B1.75 Cl ₂ CH iPr H OCH ₂ HOS B1.76 BrCH ₂ iPr H OCH ₂ HOS B1.77 FClCH iPr H OCH ₂ HOS B1.78 MeOCH ₂ iPr H OCH ₂ HOS B1.79 EtOCH ₂ iPr H OCH ₂ HOS B1.80 nPrOCH ₂ iPr H OCH ₂ HOS B1.81 MeOCH ₂ CH ₂ iPr H OCH ₂ HOS B1.82 EtOCH ₂ CH ₂ iPr H OCH ₂ HOS B2.1 F ₂ CH COOMe H OCH ₂ HOS B2.2 F ₃ C COOMe H OCH ₂ HOS B2.3 ClCH ₂ COOMe H OCH ₂ HOS B2.4 BrCH ₂ COOMe H OCH ₂ HOS B2.5 FClCH COOMe H OCH ₂ HOS B2.6 EtOCH ₂ COOMe H OCH ₂ HOS B2.7 iPr COOEt H OCH ₂ HOS B2.8 FCH ₂ COOEt H OCH ₂ HOS B2.9 F ₂ CH COOEt H OCH ₂ HOS B2.10 F ₃ C COOEt H OCH ₂ HOS B2.11 ClCH ₂ COOEt H OCH ₂ HOS B2.12 Cl ₂ CH COOEt H OCH ₂ HOS B2.13 BrCH ₂ COOEt H OCH ₂ HOS B2.14 F ClCH COOEt H OCH ₂ HOS B2.15 MeOCH ₂ COOEt H OCH ₂ HOS B2.16 EtOCH ₂ COOEt H OCH ₂ HOS B2.17 nPrOCH ₂ COOEt H OCH ₂ HOS B2.18 MeOCH ₂ CH ₂ COOEt H OCH ₂ HOS B2. 19 EtOCH ₂ CH ₂ COOEt H OCH ₂ HOS B2.20 nPr Me H OCH ₂ HOS B2.21 iPr Me H OCH ₂ HOS B2.22 nBu Me H OCH ₂ HOS B2.23 tBu Me H OCH ₂ HOS B2.24 FCH ₂ Me H OCH ₂ HOS B2.25 F ₂ CH Me H OCH ₂ HOS B2.26 CF ₃ Me H OCH ₂ HOS B2.27 ClCH ₂ Me H OCH ₂ HOS B2.28 Cl ₂ CH Me H OCH ₂ HOS B2. 29 BrCH ₂ Me H OCH ₂ HOS B2.30 FClCH Me H OCH ₂ HOS B2.31 MeOCH ₂ Me H OCH ₂ HOS B2.32 EtOCH ₂ Me H OCH ₂ HOS B2.33 nPrOCH ₂ Me H OCH ₂ HOS B2.34 MeOCH ₂ CH ₂ Me H OCH ₂ HOS B2.35 EtOCH ₂ CH ₂ Me H OCH ₂ HOS B2.36 Me CH ₂ CH = CH ₂ H OCH ₂ HOO B2.37 MeO CH ₂ CH = CH ₂ H OCH ₂ HOO Oil Object B2.38 MeO COMe H OCH ₂ HOS B2.39 MeO COMe H SCH ₂ HOS B2.40 MeO COMe H OCH ₂ HOO B2.41 MeO COEt H OCH ₂ HOS B2.42 MeO COEt H OCH ₂ HOO B2.43 MeO COnPr H OCH ₂ HOS B2.44 MeO COnPr H OCH ₂ HOO B2.45 MeO COiPr H OCH ₂ HOS B2.46 MeO COiPr H OCH ₂ HOO B2.47 MeO COnBu H OCH ₂ HOS B2. 48 MeO COnBu H OCH ₂ HOO B2.49 MeO COiBu H OCH ₂ HOS B2.50 MeO COiBu H OCH ₂ HOO B2.51 MeO COtBu H OCH ₂ HOS B2.52 MeO COtBu H OCH ₂ HOO B2.53 FCH ₂ COOMe H OCH ₂ HOS B2.54 Cl ₂ CH COOMe H OCH ₂ HOS B2.55 Cl ₃ CCH ₂ O COOMe H OCH ₂ HOS B2.56 Cl ₃ CCH ₂ O COOMe H OCH ₂ HOO B2.57 MeOCH ₂ COOMe H OCH ₂ HOS B2.58 MeOCH ₂ COOMe H OCH ₂ HOO B2.59 EtOCH ₂ COCH ₂ OEt H OCH ₂ HOS B2.60 MeO COCH ₂ OnPr H OCH ₂ HOS B2.61 MeO CO (CH ₂ ) ₂ OMe H OCH ₂ HOS B2. 62 MeO CO (CH ₂ ) ₂ OEt H OCH ₂ HOS B2.63 Me COOEt H OCH ₂ HOS 155-160 B2.64 Me COOEt H SCH ₂ HOS B2.65 Et COOEt H OCH ₂ HOS B2.66 nPr COOEt H OCH ₂ HOS B2.67 nBu COOEt H OCH ₂ HOS ────────────────────────────────────

【００５３】[0053]

【表３】 ──────────────────────────────────── 番号 R¹ R² (R³)n ACR⁴(R⁵)(R⁶)m X Q融点（℃） ──────────────────────────────────── C1.1 Me H 2-Me OCH₂ H O S 179-182 C1.2 Me H 2-Me OCH₂ H O O 160 C1.3 Me H 2-Me SCH₂ H O S 116-117 C1.4 Me H 2-Me SCH₂ H O O C1.5 MeO H 2-Me OCH₂ H O S 147-149 C1.6 MeO H 2-Me OCH₂ H O O 159-162 C1.7 MeO H 2-Me SCH₂ H O S C1.8 MeO H 2-Me SCH₂ H O O C1.9 MeO H 2-Me OCH₂ H S S C1.10 MeO H 2-Me OCH₂ H S O C1.11 MeS H 2-Me OCH₂ H O S 145-147 C1.12 MeS H 2-Me OCH₂ H O O C1.13 MeS H 2-Me OCH₂ H S S 133-135 C1.14 MeS H 2-Me OCH₂ H S O C1.15 Et H 2-Me OCH₂ H O S C1.16 Et H 2-Me OCH₂ H O O C1.17 EtO H 2-Me OCH₂ H O S 124-127 C1.18 EtO H 2-Me OCH₂ H O O C1.19 Cl₃CCH₂O H 2-Me OCH₂ H O S 166-168 C1.20 Cl₃CCH₂O H 2-Me OCH₂ H O O C1.21 nPr H 2-Me OCH₂ H O S C1.22 iPr H 2-Me OCH₂ H O S C1.23 iPrO H 2-Me OCH₂ H O S 118-120 C1.24 nPrO H 2-Me OCH₂ H O S 121-124 C1.25 nPrO H 2-Me OCH₂ H O O C1.26 nBu H 2-Me OCH₂ H O S C1.27 tBu H 2-Me OCH₂ H O S 140-142 C1.28 nBuO H 2-Me OCH₂ H O S 127-128 C1.29 nBuO H 2-Me OCH₂ H O O C1.30 tBu H 2-Me OCH₂ H O O C1.31 tBuO H 2-Me OCH₂ H O S C1.32 tBuO H 2-Me OCH₂ H O O C1.33 iBu H 2-Me OCH₂ H O S C1.34 iBuO H 2-Me OCH₂ H O S C1.35 iBuO H 2-Me OCH₂ H O O C1.36 EtOCH₂ H 2-Me OCH₂ H O S 94-95 C1.37 EtOCH₂ H 2-Me OCH₂ H O O C1.38 nPrOCH₂ H 2-Me OCH₂ H O S C1.39 nPrOCH₂ H 2-Me OCH₂ H O O C1.40 iPrOCH₂ H 2-Me OCH₂ H O S C1.41 iPrOCH₂ H 2-Me OCH₂ H O O C1.42 MeOCH₂CH₂ H 2-Me OCH₂ H O S 135-137 C1.43 MeOCH₂CH₂ H 2-Me OCH₂ H O O C1.44 EtOCH₂CH₂ H 2-Me OCH₂ H O S 135-137 C1.45 FCH₂ H 2-Me OCH₂ H O S C1.46 F₂CH H 2-Me OCH₂ H O S C1.47 F₃C H 2-Me OCH₂ H O S C1.48 ClCH₂ H 2-Me OCH₂ H O S C1.49 Cl₂CH H 2-Me OCH₂ H O S C1.50 BrCH₂ H 2-Me OCH₂ H O S C1.51 FClCH H 2-Me OCH₂ H O S C1.52 Me H 3-Me OCH₂ H O S 157-159 C1.53 Me H 3-Me SCH₂ H O S C1.54 Me H 3-Me OCH₂ H O O C1.55 MeO H 3-Me OCH₂ H O S 125-126 C1.56 MeO H 3-Me OCH₂ H O O C1.57 Et H 3-Me OCH₂ H O S C1.58 nPr H 3-Me OCH₂ H O S C1.59 iPr H 3-Me OCH₂ H O S C1.60 nBu H 3-Me OCH₂ H O S C1.61 FCH₂ H 3-Me OCH₂ H O S C1.63 F₃C H 3-Me OCH₂ H O S C1.64 ClCH₂ H 3-Me OCH₂ H O S C1.65 Cl₂CH H 3-Me OCH₂ H O S C1.66 BrCH₂ H 3-Me OCH₂ H O S C1.67 FClCH H 3-Me OCH₂ H O S C2.1 Me H 2-Et OCH₂ H O S 165-168 C2.2 Me H 2-Et SCH₂ H O S C2.3 Me H 2-Et OCH₂ H O O C2.4 MeO H 2-Et OCH₂ H O S 140-141 C2.5 MeO H 2-Et SCH₂ H O S C2.6 MeO H 2-Et OCH₂ H O O C2.7 MeO H 2-Et SCH₂ H O O C2.8 Et H 2-Et OCH₂ H O S C2.9 nPr H 2-Et OCH₂ H O S C2.10 iPr H 2-Et OCH₂ H O S C2.11 nBu H 2-Et OCH₂ H O S C2.12 FCH₂ H 2-Et OCH₂ H O S C2.13 F₂CH H 2-Et OCH₂ H O S C2.14 F₃C H 2-Et OCH₂ H O S C2.15 ClCH₂ H 2-Et OCH₂ H O S C2.16 Cl₂CH H 2-Et OCH₂ H O S C2.17 BrCH₂ H 2-Et OCH₂ H O S C2.18 FClCH H 2-Et OCH₂ H O S C2.19 Me H 3-Et OCH₂ H O S 135-137 C2.20 Me H 3-Et SCH₂ H O S C2.21 MeO H 3-Et OCH₂ H O S C2.22 MeO H 3-Et OCH₂ H O O C2.23 Et H 3-Et OCH₂ H O S C2.24 nPr H 3-Et OCH₂ H O S C2.25 iPr H 3-Et OCH₂ H O S C2.26 nBu H 3-Et OCH₂ H O S C2.27 FCH₂ H 3-Et OCH₂ H O S C2.28 F₂CH H 3-Et OCH₂ H O S C2.29 F₃C H 3-Et OCH₂ H O S C2.30 ClCH₂ H 3-Et OCH₂ H O S C2.31 Cl₂CH H 3-Et OCH₂ H O S C2.32 BrCH₂ H 3-Et OCH₂ H O S C2.33 FClCH H 3-Et OCH₂ H O S C3.1 Me H 2-nPr OCH₂ H O S C3.2 Me H 2-nPr OCH₂ H O O C3.3 MeO H 2-nPr OCH₂ H O S C3.4 MeO H 2-nPr OCH₂ H O O C3.5 Et H 2-nPr OCH₂ H O S C3.6 nPr H 2-nPr OCH₂ H O S C3.7 iPr H 2-nPr OCH₂ H O S C3.8 nBu H 2-nPr OCH₂ H O S C3.9 FCH₂ H 2-nPr OCH₂ H O S C3.10 F₂CH H 2-nPr OCH₂ H O S C3.11 F₃C H 2-nPr OCH₂ H O S C3.12 ClCH₂ H 2-nPr OCH₂ H O S C3.13 Cl₂CH H 2-nPr OCH₂ H O S C3.14 BrCH₂ H 2-nPr OCH₂ H O S C3.15 FClCH H 2-nPr OCH₂ H O S C3.16 Me H 3-nPr OCH₂ H O S C3.17 MeO H 3-nPr OCH₂ H O S C3.18 MeO H 3-nPr OCH₂ H O O C3.19 Et H 3-nPr OCH₂ H O S C3.21 iPr H 3-nPr OCH₂ H O S C3.22 nBu H 3-nPr OCH₂ H O S C3.23 FCH₂ H 3-nPr OCH₂ H O S C3.24 F₂CH H 3-nPr OCH₂ H O S C3.25 F₃C H 3-nPr OCH₂ H O S C3.26 ClCH₂ H 3-nPr OCH₂ H O S C3.27 Cl₂CH H 3-nPr OCH₂ H O S C3.28 BrCH₂ H 3-nPr OCH₂ H O S C3.29 FClCH H 3-nPr OCH₂ H O S C3.30 Me H 2-iPr OCH₂ H O S 165-170 C3.31 Me H 2-iPr OCH₂ H O O C3.32 MeO H 2-iPr OCH₂ H O S 113-114 C3.33 MeO H 2-iPr OCH₂ H O O C3.34 Et H 2-iPr OCH₂ H O S C3.35 nPr H 2-iPr OCH₂ H O S C3.36 iPr H 2-iPr OCH₂ H O S C3.37 nBu H 2-iPr OCH₂ H O S C3.38 FCH₂ H 2-iPr OCH₂ H O S C3.39 F₂CH H 2-iPr OCH₂ H O S C3.40 F₃C H 2-iPr OCH₂ H O S C3.41 ClCH₂ H 2-iPr OCH₂ H O S C3.42 Cl₂CH H 2-iPr OCH₂ H O S C3.43 BrCH₂ H 2-iPr OCH₂ H O S C3.44 FClCH H 2-iPr OCH₂ H O S C3.45 Me H 3-iPr OCH₂ H O S C3.46 MeO H 3-iPr OCH₂ H O S C3.47 Et H 3-iPr OCH₂ H O S C3.48 nPr H 3-iPr OCH₂ H O S C3.49 iPr H 3-iPr OCH₂ H O S C3.50 nBu H 3-iPr OCH₂ H O S C3.51 FCH₂ H 3-iPr OCH₂ H O S C3.52 F₂CH H 3-iPr OCH₂ H O S C3.53 F₃C H 3-iPr OCH₂ H O S C3.54 ClCH₂ H 3-iPr OCH₂ H O S C3.55 Cl₂CH H 3-iPr OCH₂ H O S C3.56 BrCH₂ H 3-iPr OCH₂ H O S C3.57 FClCH H 3-iPr OCH₂ H O S C4.1 Me H 2-nBu OCH₂ H O S C4.2 MeO H 2-nBu OCH₂ H O S C4.3 MeO H 2-nBu OCH₂ H O O C4.4 Et H 2-nBu OCH₂ H O S C4.5 nPr H 2-nBu OCH₂ H O S C4.6 iPr H 2-nBu OCH₂ H O S C4.7 nBu H 2-nBu OCH₂ H O S C4.8 FCH₂ H 2-nBu OCH₂ H O S C4.9 F₂CH H 2-nBu OCH₂ H O S C4.10 F₃C H 2-nBu OCH₂ H O S C4.11 ClCH₂ H 2-nBu OCH₂ H O S C4.12 Cl₂CH H 2-nBu OCH₂ H O S C4.13 BrCH₂ H 2-nBu OCH₂ H O S C4.14 FClCH H 2-nBu OCH₂ H O S C4.15 Me H 2-iBu OCH₂ H O S C4.16 Et H 2-iBu OCH₂ H O S C4.17 nPr H 2-iBu OCH₂ H O S C4.18 iPr H 2-iBu OCH₂ H O S C4.19 nBu H 2-iBu OCH₂ H O S C4.20 FCH₂ H 2-iBu OCH₂ H O S C4.21 F₂CH H 2-iBu OCH₂ H O S Ｃ４．２２ F₃C H 2-iBu OCH₂ H O S C4.23 ClCH₂ H 2-iBu OCH₂ H O S C4.24 Cl₂CH H 2-iBu OCH₂ H O S C4.25 BrCH₂ H 2-iBu OCH₂ H O S C4.26 FClCH H 2-iBu OCH₂ H O S C4.27 Me H 2-tBu OCH₂ H O S 158-165 C4.28 Me H 2-tBu OCH₂ H O O C4.29 MeO H 2-tBu OCH₂ H O S 162-164 C4.30 MeO H 2-tBu OCH₂ H O O C4.31 Et H 2-tBu OCH₂ H O S C4.32 nPr H 2-tBu OCH₂ H O S C4.33 iPr H 2-tBu OCH₂ H O S C4.34 nBu H 2-tBu OCH₂ H O S C4.35 FCH₂ H 2-tBu OCH₂ H O S C4.36 F₂CH H 2-tBu OCH₂ H O S C4.37 F₃C H 2-tBu OCH₂ H O S C4.38 ClCH₂ H 2-tBu OCH₂ H O S C4.39 Cl₂CH H 2-tBu OCH₂ H O S C4.40 BrCH₂ H 2-tBu OCH₂ H O S C4.41 FClCH H 2-tBu OCH₂ H O S C4.42 MeO H 3-nBu OCH₂ H O S C4.43 MeO H 3-nBu OCH₂ H O O C4.44 Me H 3-nBu OCH₂ H O S C4.45 Et H 3-nBu OCH₂ H O S C4.46 nPr H 3-nBu OCH₂ H O S C4.47 iPr H 3-nBu OCH₂ H O S C4.48 nBu H 3-nBu OCH₂ H O S C4.49 FCH₂ H 3-nBu OCH₂ H O S C4.50 F₂CH H 3-nBu OCH₂ H O S C4.51 F₃C H 3-nBu OCH₂ H O S C4.52 ClCH₂ H 3-nBu OCH₂ H O S C4.53 Cl₂CH H 3-nBu OCH₂ H O S C4.54 BrCH₂ H 3-nBu OCH₂ H O S C4.55 FClCH H 3-nBu OCH₂ H O S C4.56 Me H 3-iBu OCH₂ H O S C4.57 Et H 3-iBu OCH₂ H O S C4.58 nPr H 3-iBu OCH₂ H O S C4.59 iPr H 3-iBu OCH₂ H O S C4.60 nBu H 3-iBu OCH₂ H O S C4.61 FCH₂ H 3-iBu OCH₂ H O S C4.62 F₂CH H 3-iBu OCH₂ H O S C4.63 F₃C H 3-iBu OCH₂ H O S C4.64 ClCH₂ H 3-iBu OCH₂ H O S C4.65 Cl₂CH H 3-iBu OCH₂ H O S C4.66 BrCH₂ H 3-iBu OCH₂ H O S C4.67 FClCH H 3-iBu OCH₂ H O S C4.68 Me H 3-tBu OCH₂ H O S C4.69 MeO H 3-tBu OCH₂ H O S C4.70 Et H 3-tBu OCH₂ H O S C4.71 nPr H 3-tBu OCH₂ H O S C4.72 iPr H 3-tBu OCH₂ H O S C4.73 nBu H 3-tBu OCH₂ H O S C4.74 FCH₂ H 3-tBu OCH₂ H O S C4.75 F₂CH H 3-tBu OCH₂ H O S C4.76 F₃C H 3-tBu OCH₂ H O S C4.77 ClCH₂ H 3-tBu OCH₂ H O S C4.78 Cl₂CH H 3-tBu OCH₂ H O S C4.79 BrCH₂ H 3-tBu OCH₂ H O S C4.80 FClCH H 3-tBu OCH₂ H O S C5.1 Me H 2-CH₂CH=CH₂ OCH₂ H O S C5.2 MeO H 2-CH₂CH=CH₂ OCH₂ H O S C5.3 MeO H 2-CH₂CH=CH₂ OCH₂ H O O C5.4 Et H 2-CH₂CH=CH₂ OCH₂ H O S C5.5 nPr H 2-CH₂CH=CH₂ OCH₂ H O S C5.6 iPr H 2-CH₂CH=CH₂ OCH₂ H O S C5.7 nBu H 2-CH₂CH=CH₂ OCH₂ H O S C5.8 FCH₂ H 2-CH₂CH=CH₂ OCH₂ H O S C5.9 F₂CH H 2-CH₂CH=CH₂ OCH₂ H O S C5.10 F₃C H 2-CH₂CH=CH₂ OCH₂ H O S C5.11 ClCH₂ H 2-CH₂CH=CH₂ OCH₂ H O S C5.12 Cl₂CH H 2-CH₂CH=CH₂ OCH₂ H O S C5.13 BrCH₂ H 2-CH₂CH=CH₂ OCH₂ H O S C5.14 FClCH H 2-CH₂CH=CH₂ OCH₂ H O S C5.15 Me H 3-CH₂CH=CH₂ OCH₂ H O S C5.16 MeO H 3-CH₂CH=CH₂ OCH₂ H O S C5.17 MeO H 3-CH₂CH=CH₂ OCH₂ H O O C5.18 Et H 3-CH₂CH=CH₂ OCH₂ H O S C5.19 nPr H 3-CH₂CH=CH₂ OCH₂ H O S C5.20 iPr H 3-CH₂CH=CH₂ OCH₂ H O S C5.21 nBu H 3-CH₂CH=CH₂ OCH₂ H O S C5.22 FCH₂ H 3-CH₂CH=CH₂ OCH₂ H O S C5.23 F₂CH H 3-CH₂CH=CH₂ OCH₂ H O S C5.24 F₃C H 3-CH₂CH=CH₂ OCH₂ H O S C5.25 ClCH₂ H 3-CH₂CH=CH₂ OCH₂ H O S C5.26 Cl₂CH H 3-CH₂CH=CH₂ OCH₂ H O S C5.27 BrCH₂ H 3-CH₂CH=CH₂ OCH₂ H O S C5.28 FClCH H 3-CH₂CH=CH₂ OCH₂ H O S C5.29 Me H 2-CH₂C≡CH OCH₂ H O S C5.30 MeO H 2-CH₂C≡CH OCH₂ H O S C5.31 MeO H 2-CH₂C≡CH OCH₂ H O O C5.32 Et H 2-CH₂C≡CH OCH₂ H O S C5.33 nPr H 2-CH₂C≡CH OCH₂ H O S C5.34 iPr H 2-CH₂C≡CH OCH₂ H O S C5.35 nBu H 2-CH₂C≡CH OCH₂ H O S C5.36 FCH₂ H 2-CH₂C≡CH OCH₂ H O S C5.37 F₂CH H 2-CH₂C≡CH OCH₂ H O S C5.38 F₃C H 2-CH₂C≡CH OCH₂ H O S C5.39 ClCH₂ H 2-CH₂C≡CH OCH₂ H O S C5.40 Cl₂CH H 2-CH₂C≡CH OCH₂ H O S C5.41 BrCH₂ H 2-CH₂C≡CH OCH₂ H O S C5.42 FClCH H 2-CH₂C≡CH OCH₂ H O S C5.43 Me H 3-CH₂C≡CH OCH₂ H O S C5.44 MeO H 3-CH₂C≡CH OCH₂ H O S C5.45 Et H 3-CH₂C≡CH OCH₂ H O S C5.46 nPr H 3-CH₂C≡CH OCH₂ H O S C5.47 iPr H 3-CH₂C≡CH OCH₂ H O S C5.48 nBu H 3-CH₂C≡CH OCH₂ H O S C5.49 FCH₂ H 3-CH₂C≡CH OCH₂ H O S C5.50 F₂CH H 3-CH₂C≡CH OCH₂ H O S C5.51 F₃C H 3-CH₂C≡CH OCH₂ H O S C5.52 ClCH₂ H 3-CH₂C≡CH OCH₂ H O S C5.53 Cl₂CH H 3-CH₂C≡CH OCH₂ H O S C5.54 BrCH₂ H 3-CH₂C≡CH OCH₂ H O S C5.55 FClCH H 3-CH₂C≡CH OCH₂ H O S C6.1 Me H 2-CH₂OMe OCH₂ H O S 157-160 C6.2 MeO H 2-CH₂OMe OCH₂ H O S Ｃ６．３ Me H 2-CH₂OMe OCH₂ H O O C6.4 MeO H 2-CH₂OMe OCH₂ H O O C6.5 Et H 2-CH₂OMe OCH₂ H O S C6.6 nPr H 2-CH₂OMe OCH₂ H O S C6.7 iPr H 2-CH₂OMe OCH₂ H O S C6.8 nBu H 2-CH₂OMe OCH₂ H O S C6.9 FCH₂ H 2-CH₂OMe OCH₂ H O S C6.10 F₂CH H 2-CH₂OMe OCH₂ H O S C6.11 F₃C H 2-CH₂OMe OCH₂ H O S C6.12 ClCH₂ H 2-CH₂OMe OCH₂ H O S C6.13 Cl₂CH H 2-CH₂OMe OCH₂ H O S C6.14 BrCH₂ H 2-CH₂OMe OCH₂ H O S C6.15 FClCH H 2-CH₂OMe OCH₂ H O S C6.16 Me H 3-CH₂OMe OCH₂ H O S C6.17 MeO H 3-CH₂OMe OCH₂ H O S C6.18 Et H 3-CH₂OMe OCH₂ H O S C6.19 nPr H 3-CH₂OMe OCH₂ H O S C6.20 iPr H 3-CH₂OMe OCH₂ H O S C6.21 nBu H 3-CH₂OMe OCH₂ H O S C6.22 FCH₂ H 3-CH₂OMe OCH₂ H O S C6.23 F₂CH H 3-CH₂OMe OCH₂ H O S C6.24 F₃C H 3-CH₂OMe OCH₂ H O S C6.25 ClCH₂ H 3-CH₂OMe OCH₂ H O S C6.26 Cl₂CH H 3-CH₂OMe OCH₂ H O S C6.27 BrCH₂ H 3-CH₂OMe OCH₂ H O S C6.28 FClCH H 3-CH₂OMe OCH₂ H O S C6.29 Me H 2-CH₂OEt OCH₂ H O S 154-156 C6.30 Me H 2-CH₂OEt OCH₂ H O O C6.31 MeO H 2-CH₂OEt OCH₂ H O S C6.32 Et H 2-CH₂OEt OCH₂ H O S C6.33 nPr H 2-CH₂OEt OCH₂ H O S C6.34 iPr H 2-CH₂OEt OCH₂ H O S C6.35 nBu H 2-CH₂OEt OCH₂ H O S C6.36 FCH₂ H 2-CH₂OEt OCH₂ H O S C6.37 F₂CH H 2-CH₂OEt OCH₂ H O S C6.38 F₃C H 2-CH₂OEt OCH₂ H O S C6.39 ClCH₂ H 2-CH₂OEt OCH₂ H O S C6.40 Cl₂CH H 2-CH₂OEt OCH₂ H O S C6.41 BrCH₂ H 2-CH₂OEt OCH₂ H O S C6.42 FClCH H 2-CH₂OEt OCH₂ H O S C6.43 Me H 3-CH₂OEt OCH₂ H O S C6.44 Et H 3-CH₂OEt OCH₂ H O S C6.45 nPr H 3-CH₂OEt OCH₂ H O S C6.46 iPr H 3-CH₂OEt OCH₂ H O S C6.47 nBu H 3-CH₂OEt OCH₂ H O S C6.48 FCH₂ H 3-CH₂OEt OCH₂ H O S C6.49 F₂CH H 3-CH₂OEt OCH₂ H O S C6.50 F₃C H 3-CH₂OEt OCH₂ H O S C6.51 ClCH₂ H 3-CH₂OEt OCH₂ H O S C6.52 Cl₂CH H 3-CH₂OEt OCH₂ H O S C6.53 BrCH₂ H 3-CH₂OEt OCH₂ H O S C6.54 FClCH H 3-CH₂OEt OCH₂ H O S C6.55 Me H 2-CH₂CH₂OMe OCH₂ H O S C6.56 Et H 2-CH₂CH₂OMe OCH₂ H O S C6.57 nPr H 2-CH₂CH₂OMe OCH₂ H O S C6.58 iPr H 2-CH₂CH₂OMe OCH₂ H O S C6.59 nBu H 2-CH₂CH₂OMe OCH₂ H O S C6.60 FCH₂ H 2-CH₂CH₂OMe OCH₂ H O S C6.61 F₂CH H 2-CH₂CH₂OMe OCH₂ H O S C6.62 F₃C H 2-CH₂CH₂OMe OCH₂ H O S C6.63 ClCH₂ H 2-CH₂CH₂OMe OCH₂ H O S C6.64 Cl₂CH H 2-CH₂CH₂OMe OCH₂ H O S C6.65 BrCH₂ H 2-CH₂CH₂OMe OCH₂ H O S C6.66 FClCH H 2-CH₂CH₂OMe OCH₂ H O S C6.67 Me H 3-CH₂CH₂OMe OCH₂ H O S C6.68 Me H 3-CH₂CH₂OMe OCH₂ H O O C6.69 Et H 3-CH₂CH₂OMe OCH₂ H O S C6.70 nPr H 3-CH₂CH₂OMe OCH₂ H O S C6.71 iPr H 3-CH₂CH₂OMe OCH₂ H O S C6.72 nBu H 3-CH₂CH₂OMe OCH₂ H O S C6.73 FCH₂ H 3-CH₂CH₂OMe OCH₂ H O S C6.74 F₂CH H 3-CH₂CH₂OMe OCH₂ H O S C6.75 F₃C H 3-CH₂CH₂OMe OCH₂ H O S C6.76 ClCH₂ H 3-CH₂CH₂OMe OCH₂ H O S C6.77 Cl₂CH H 3-CH₂CH₂OMe OCH₂ H O S C6.78 BrCH₂ H 3-CH₂CH₂OMe OCH₂ H O S C6.79 FClCH H 3-CH₂CH₂OMe OCH₂ H O S C6.80 Me H 2-CH₂CH₂OEt OCH₂ H O S C6.81 Et H 2-CH₂CH₂OEt OCH₂ H O S C6.82 nPr H 2-CH₂CH₂OEt OCH₂ H O S C6.83 iPr H 2-CH₂CH₂OEt OCH₂ H O S C6.84 nBu H 2-CH₂CH₂OEt OCH₂ H O S C6.85 FCH₂ H 2-CH₂CH₂OEt OCH₂ H O S C6.86 F₂CH H 2-CH₂CH₂OEt OCH₂ H O S C6.87 F₃C H 2-CH₂CH₂OEt OCH₂ H O S C6.88 ClCH₂ H 2-CH₂CH₂OEt OCH₂ H O S C6.89 Cl₂CH H 2-CH₂CH₂OEt OCH₂ H O S C6.90 BrCH₂ H 2-CH₂CH₂OEt OCH₂ H O S C6.91 FClCH H 2-CH₂CH₂OEt OCH₂ H O S C6.92 Me H 3-CH₂CH₂OEt OCH₂ H O S C6.93 Et H 3-CH₂CH₂OEt OCH₂ H O S C6.94 nPr H 3-CH₂CH₂OEt OCH₂ H O S C6.95 iPr H 3-CH₂CH₂OEt OCH₂ H O S C6.96 nBu H 3-CH₂CH₂OEt OCH₂ H O S C6.97 FCH₂ H 3-CH₂CH₂OEt OCH₂ H O S C6.98 F₂CH H 3-CH₂CH₂OEt OCH₂ H O S C6.99 F₃C H 3-CH₂CH₂OEt OCH₂ H O S C6.100 ClCH₂ H 3-CH₂CH₂OEt OCH₂ H O S C6.101 Cl₂CH H 3-CH₂CH₂OEt OCH₂ H O S C6.102 BrCH₂ H 3-CH₂CH₂OEt OCH₂ H O S C6.103 FClCH H 3-CH₂CH₂OEt OCH₂ H O S C7.1 Me H 2-CH₂Cl OCH₂ H O S C7.2 MeO H 2-CH₂Cl OCH₂ H O S C7.3 Me H 2-CH₂Cl SCH₂ H O S C7.4 Et H 2-CH₂Cl OCH₂ H O S C7.5 nPr H 2-CH₂Cl OCH₂ H O S C7.6 iPr H 2-CH₂Cl OCH₂ H O S C7.7 nBu H 2-CH₂Cl OCH₂ H O S C7.8 FCH₂ H 2-CH₂Cl OCH₂ H O S C7.9 F₂CH H 2-CH₂Cl OCH₂ H O S C7.10 F₃C H 2-CH₂Cl OCH₂ H O S C7.11 ClCH₂ H 2-CH₂Cl OCH₂ H O S C7.12 Cl₂CH H 2-CH₂Cl OCH₂ H O S C7.13 BrCH₂ H 2-CH₂Cl OCH₂ H O S C7.14 FClCH H 2-CH₂Cl OCH₂ H O S C7.15 Me H 2-CH₂Br OCH₂ H O S C7.16 Et H 2-CH₂Br OCH₂ H O S C7.17 nPr H 2-CH₂Br OCH₂ H O S C7.18 iPr H 2-CH₂Br OCH₂ H O S C7.19 nBu H 2-CH₂Br OCH₂ H O S C7.20 FCH₂ H 2-CH₂Br OCH₂ H O S C7.21 F₂CH H 2-CH₂Br OCH₂ H O S C7.22 F₃C H 2-CH₂Br OCH₂ H O S C7.23 ClCH₂ H 2-CH₂Br OCH₂ H O S C7.24 Cl₂CH H 2-CH₂Br OCH₂ H O S C7.25 BrCH₂ H 2-CH₂Br OCH₂ H O S C7.26 FClCH H 2-CH₂Br OCH₂ H O S C7.27 Me H 3-CH₂Cl OCH₂ H O S C7.28 MeO H 3-CH₂Cl OCH₂ H O S C7.29 Me H 3-CH₂Cl SCH₂ H O S C7.30 Et H 3-CH₂Cl OCH₂ H O S C7.31 nPr H 3-CH₂Cl OCH₂ H O S C7.32 iPr H 3-CH₂Cl OCH₂ H O S C7.33 nBu H 3-CH₂Cl OCH₂ H O S C7.34 FCH₂ H 3-CH₂Cl OCH₂ H O S C7.35 F₂CH H 3-CH₂Cl OCH₂ H O S C7.36 F₃C H 3-CH₂Cl OCH₂ H O S C7.37 ClCH₂ H 3-CH₂Cl OCH₂ H O S C7.38 Cl₂CH H 3-CH₂Cl OCH₂ H O S C7.39 BrCH₂ H 3-CH₂Cl OCH₂ H O S C7.40 FClCH H 3-CH₂Cl OCH₂ H O S C7.41 Me H 3-CH₂Br OCH₂ H O S C7.42 Et H 3-CH₂Br OCH₂ H O S C7.43 nPr H 3-CH₂Br OCH₂ H O S C7.44 iPr H 3-CH₂Br OCH₂ H O S C7.45 nBu H 3-CH₂Br OCH₂ H O S C7.46 FCH₂ H 3-CH₂Br OCH₂ H O S C7.47 F₂CH H 3-CH₂Br OCH₂ H O S C7.48 F₃C H 3-CH₂Br OCH₂ H O S C7.49 ClCH₂ H 3-CH₂Br OCH₂ H O S C7.50 Cl₂CH H 3-CH₂Br OCH₂ H O S C7.51 BrCH₂ H 3-CH₂Br OCH₂ H O S C7.52 FClCH H 3-CH₂Br OCH₂ H O S C7.53 MeO H 3-CH₂F OCH₂ H O S C7.54 MeO H 3-CH₂F OCH₂ H O S C7.55 Me H 2-CHF₂ OCH₂ H O S 195-198 C7.56 MeO H 2-CHF₂ OCH₂ H O S C7.57 Me H 2-CHF₂ OCH₂ H O O C7.58 MeO H 2-CHF₂ OCH₂ H O O C8.1 Me H 2-OMe OCH₂ H O S 163-165 C8.2 Me H 2-OMe OCH₂ H O O 118-119 C8.3 MeO H 2-OMe OCH₂ H O S 112-114 C8.4 Me H 2-OMe SCH₂ H O S C8.5 MeO H 2-OMe SCH₂ H O S C8.6 MeO H 2-OMe OCH₂ H O O 91-93 C8.7 MeO H 2-OMe SCH₂ H O O C8.8 Et H 2-OMe OCH₂ H O S C8.9 nPr H 2-OMe OCH₂ H O S C8.10 iPr H 2-OMe OCH₂ H O S C8.11 nBu H 2-OMe OCH₂ H O S C8.12 FCH₂ H 2-OMe OCH₂ H O S C8.13 F₂CH H 2-OMe OCH₂ H O S C8.14 F₃C H 2-OMe OCH₂ H O S C8.15 ClCH₂ H 2-OMe OCH₂ H O S C8.16 Cl₂CH H 2-OMe OCH₂ H O S C8.17 BrCH₂ H 2-OMe OCH₂ H O S C8.18 FClCH H 2-OMe OCH₂ H O S C8.19 Me H 3-OMe OCH₂ H O S 108-113 C8.20 MeO H 3-OMe OCH₂ H O S 93-96 C8.21 Me H 3-OMe SCH₂ H O S C8.22 Me H 3-OMe OCH₂ H O O 98-100 C8.23 MeO H 3-OMe OCH₂ H O O 97-99 C8.24 Et H 3-OMe OCH₂ H O S C8.25 nPr H 3-OMe OCH₂ H O S C8.26 iPr H 3-OMe OCH₂ H O S C8.27 nBu H 3-OMe OCH₂ H O S C8.28 FCH₂ H 3-OMe OCH₂ H O S C8.29 F₂CH H 3-OMe OCH₂ H O S C8.30 F₃C H 3-OMe OCH₂ H O S C8.31 ClCH₂ H 3-OMe OCH₂ H O S C8.32 Cl₂CH H 3-OMe OCH₂ H O S C8.33 BrCH₂ H 3-OMe OCH₂ H O S C8.34 FClCH H 3-OMe OCH₂ H O S C8.35 Me H 2-OEt OCH₂ H O O C8.36 Me H 2-OEt SCH₂ H O O C8.37 MeO H 2-OEt OCH₂ H O S C8.38 MeO H 2-OEt OCH₂ H O O C8.39 Me H 2-OEt OCH₂ H O S 131-133 C8.40 MeO H 2-OEt SCH₂ H O S C8.41 Me H 2-OEt SCH₂ H O S C8.42 Et H 2-OEt OCH₂ H O S C8.43 nPr H 2-OEt OCH₂ H O S C8.44 iPr H 2-OEt OCH₂ H O S C8.45 nBu H 2-OEt OCH₂ H O S C8.46 FCH₂ H 2-OEt OCH₂ H O S C8.47 F₂CH H 2-OEt OCH₂ H O S C8.48 F₃C H 2-OEt OCH₂ H O S C8.49 ClCH₂ H 2-OEt OCH₂ H O S C8.50 Cl₂CH H 2-OEt OCH₂ H O S C8.51 BrCH₂ H 2-OEt OCH₂ H O S C8.52 FClCH H 2-OEt OCH₂ H O S C8.53 Me H 3-OEt OCH₂ H O S C8.54 MeO H 3-OEt OCH₂ H O O C8.55 MeO H 3-OEt OCH₂ H O S C8.56 Me H 3-OEt SCH₂ H O S C8.57 Et H 3-OEt OCH₂ H O S C8.58 nPr H 3-OEt OCH₂ H O S C8.59 iPr H 3-OEt OCH₂ H O S C8.60 nBu H 3-OEt OCH₂ H O S C8.61 FCH₂ H 3-OEt OCH₂ H O S C8.62 F₂CH H 3-OEt OCH₂ H O S C8.63 F₃C H 3-OEt OCH₂ H O S C8.64 ClCH₂ H 3-OEt OCH₂ H O S C8.65 Cl₂CH H 3-OEt OCH₂ H O S C8.66 BrCH₂ H 3-OEt OCH₂ H O S C8.67 FClCH H 3-OEt OCH₂ H O S C8.68 Me H 2-OiPr OCH₂ H O S C8.69 MeO H 2-OiPr OCH₂ H O S C8.70 Me H 2-OiPr OCH₂ H O O C8.71 MeO H 2-OiPr OCH₂ H O O C8.72 Me H 2-OCHF₂ OCH₂ H O S 120-121 C8.73 MeO H 2-OCHF₂ OCH₂ H O S C8.74 Me H 2-OCHF₂ OCH₂ H O O C8.75 MeO H 2-OCHF₂ OCH₂ H O O C8.76 Me H 2-OCH₂CF₃ OCH₂ H O S 136-138 C8.77 Me H 2-OCH₂CF₃ OCH₂ H O O C8.78 MeO H 2-OCH₂CF₃ OCH₂ H O S C9.1 Me H 2-F OCH₂ H O S 167-169 C9.2 Me H 2-F SCH₂ H O S C9.3 Me H 2-F OCH₂ H O O 135-136 C9.4 MeO H 2-F OCH₂ H O S 124-127 C9.5 MeO H 2-F SCH₂ H O S C9.6 MeO H 2-F OCH₂ H O O 110-115 C9.7 MeO H 2-F SCH₂ H O O C9.8 Et H 2-F OCH₂ H O S C9.9 nPr H 2-F OCH₂ H O S C9.10 iPr H 2-F OCH₂ H O S C9.11 nBu H 2-F OCH₂ H O S C9.12 FCH₂ H 2-F OCH₂ H O S C9.13 F₂CH H 2-F OCH₂ H O S C9.14 F₃C H 2-F OCH₂ H O S C9.15 ClCH₂ H 2-F OCH₂ H O S C9.16 Cl₂CH H 2-F OCH₂ H O S C9.17 BrCH₂ H 2-F OCH₂ H O S C9.18 FClCH H 2-F OCH₂ H O S C9.20 Me H 3-F OCH₂ H O S 150-151 C9.21 Me H 3-F SCH₂ H O S C9.22 Me H 3-F OCH₂ H O O 140-142 C9.23 MeO H 3-F OCH₂ H O S 112-115 C9.24 MeO H 3-F OCH₂ H O O 135-138 C9.25 Et H 3-F OCH₂ H O S C9.26 nPr H 3-F OCH₂ H O S C9.27 iPr H 3-F OCH₂ H O S C9.28 nBu H 3-F OCH₂ H O S C9.29 FCH₂ H 3-F OCH₂ H O S C9.30 F₂CH H 3-F OCH₂ H O S C9.31 F₃C H 3-F OCH₂ H O S C9.32 ClCH₂ H 3-F OCH₂ H O S C9.33 Cl₂CH H 3-F OCH₂ H O S C9.34 BrCH₂ H 3-F OCH₂ H O S C9.35 FClCH H 3-F OCH₂ H O S C9.36 Me H 2-Cl OCH₂ H O S 159-161 C9.37 Me H 2-Cl SCH₂ H O S C9.38 Me H 2-Cl OCH₂ H O O 130-131 C9.39 MeO H 2-Cl OCH₂ H O S 173.5-174.5 C9.40 MeO H 2-Cl OCH₂ H O O 120-122 C9.41 Et H 2-Cl OCH₂ H O S C9.42 nPr H 2-Cl OCH₂ H O S C9.43 iPr H 2-Cl OCH₂ H O S C9.44 nBu H 2-Cl OCH₂ H O S C9.45 FCH₂ H 2-Cl OCH₂ H O S C9.46 F₂CH H 2-Cl OCH₂ H O S C9.47 F₃C H 2-Cl OCH₂ H O S C9.48 ClCH₂ H 2-Cl OCH₂ H O S C9.49 Cl₂CH H 2-Cl OCH₂ H O S C9.50 BrCH₂ H 2-Cl OCH₂ H O S C9.51 FClCH H 2-Cl OCH₂ H O S C9.52 Me H 3-Cl OCH₂ H O S 168-169 C9.53 Me H 3-Cl SCH₂ H O S C9.54 Me H 3-Cl OCH₂ H O O 161-165 C9.55 MeO H 3-Cl OCH₂ H O S 133-135 C9.56 MeO H 3-Cl OCH₂ H O O 164-166 C9.57 Et H 3-Cl OCH₂ H O S C9.58 nPr H 3-Cl OCH₂ H O S C9.59 iPr H 3-Cl OCH₂ H O S C9.60 nBu H 3-Cl OCH₂ H O S C9.61 FCH₂ H 3-Cl OCH₂ H O S C9.62 F₂CH H 3-Cl OCH₂ H O S C9.63 F₃C H 3-Cl OCH₂ H O S C9.64 ClCH₂ H 3-Cl OCH₂ H O S C9.65 Cl₂CH H 3-Cl OCH₂ H O S C9.66 BrCH₂ H 3-Cl OCH₂ H O S C9.67 FClCH H 3-Cl OCH₂ H O S C9.68 Me H 2-Br OCH₂ H O S C9.69 Et H 2-Br OCH₂ H O S C9.70 nPr H 2-Br OCH₂ H O S C9.71 iPr H 2-Br OCH₂ H O S C9.72 nBu H 2-Br OCH₂ H O S C9.73 FCH₂ H 2-Br OCH₂ H O S C9.74 F₂CH H 2-Br OCH₂ H O S C9.75 F₃C H 2-Br OCH₂ H O S C9.76 ClCH₂ H 2-Br OCH₂ H O S C9.77 Cl₂CH H 2-Br OCH₂ H O S C9.78 BrCH₂ H 2-Br OCH₂ H O S C9.79 FClCH H 2-Br OCH₂ H O S C9.80 Me H 3-Br OCH₂ H O S C9.81 Et H 3-Br OCH₂ H O S C9.82 nPr H 3-Br OCH₂ H O S C9.84 nBu H 3-Br OCH₂ H O S C9.85 FCH₂ H 3-Br OCH₂ H O S C9.86 F₂CH H 3-Br OCH₂ H O S C9.87 F₃C H 3-Br OCH₂ H O S C9.88 ClCH₂ H 3-Br OCH₂ H O S C9.89 Cl₂CH H 3-Br OCH₂ H O S C9.90 BrCH₂ H 3-Br OCH₂ H O S C9.91 FClCH H 3-Br OCH₂ H O S C9.92 Me H 2-I OCH₂ H O S C9.93 Et H 2-I OCH₂ H O S C9.94 nPr H 2-I OCH₂ H O S C9.95 iPr H 2-I OCH₂ H O S C9.96 nBu H 2-I OCH₂ H O S C9.97 FCH₂ H 2-I OCH₂ H O S C9.98 F₂CH H 2-I OCH₂ H O S C9.99 F₃C H 2-I OCH₂ H O S C9.100 ClCH₂ H 2-I OCH₂ H O S C9.101 Cl₂CH H 2-I OCH₂ H O S C9.102 BrCH₂ H 2-I OCH₂ H O S C9.103 FClCH H 2-I OCH₂ H O S C9.104 Me H 3-I OCH₂ H O S C9.105 Et H 3-I OCH₂ H O S C9.106 nPr H 3-I OCH₂ H O S C9.107 iPr H 3-I OCH₂ H O S C9.108 nBu H 3-I OCH₂ H O S C9.109 FCH₂ H 3-I OCH₂ H O S C9.110 F₂CH H 3-I OCH₂ H O S C9.111 F₃C H 3-I OCH₂ H O S C9.112 ClCH₂ H 3-I OCH₂ H O S C9.113 Cl₂CH H 3-I OCH₂ H O S C9.114 BrCH₂ H 3-I OCH₂ H O S C9.115 FClCH H 3-I OCH₂ H O S C10.1 Me H 2-CF₃ OCH₂ H O S 178 C10.2 Me H 2-CF₃ SCH₂ H O S C10.3 Me H 2-CF₃ OCH₂ H O O 145-147 C10.4 MeO H 2-CF₃ OCH₂ H O S 133-135 C10.5 MeO H 2-CF₃ OCH₂ H O O 69-71 C10.6 Et H 2-CF₃ OCH₂ H O S C10.7 nPr H 2-CF₃ OCH₂ H O S C10.8 iPr H 2-CF₃ OCH₂ H O S C10.9 nBu H 2-CF₃ OCH₂ H O S C10.10 FCH₂ H 2-CF₃ OCH₂ H O S C10.11 F₂CH H 2-CF₃ OCH₂ H O S C10.12 F₃C H 2-CF₃ OCH₂ H O S C10.13 ClCH₂ H 2-CF₃ OCH₂ H O S C10.14 Cl₂CH H 2-CF₃ OCH₂ H O S C10.15 BrCH₂ H 2-CF₃ OCH₂ H O S C10.16 FClCH H 2-CF₃ OCH₂ H O S C10.17 Me H 3-CF₃ OCH₂ H O S 174-175 C10.18 Me H 3-CF₃ SCH₂ H O S C10.19 Me H 3-CF₃ OCH₂ H O O C10.20 MeO H 3-CF₃ OCH₂ H O S 142-146 C10.21 MeO H 3-CF₃ OCH₂ H O O C10.22 Et H 3-CF₃ OCH₂ H O S C10.23 nPr H 3-CF₃ OCH₂ H O S C10.24 iPr H 3-CF₃ OCH₂ H O S C10.25 nBu H 3-CF₃ OCH₂ H O S C10.26 FCH₂ H 3-CF₃ OCH₂ H O S C10.27 F₂CH H 3-CF₃ OCH₂ H O S C10.28 F₃C H 3-CF₃ OCH₂ H O S C10.29 ClCH₂ H 3-CF₃ OCH₂ H O S C10.30 Cl₂CH H 3-CF₃ OCH₂ H O S C10.31 BrCH₂ H 3-CF₃ OCH₂ H O S C10.32 FClCH H 3-CF₃ OCH₂ H O S C10.33 iPr H 3-CHO OCH₂ H O S C10.34 nBu H 3-CHO OCH₂ H O S C10.35 FCH₂ H 3-CHO OCH₂ H O S C10.36 F₂CH H 3-CHO OCH₂ H O S C10.37 F₃C H 3-CHO OCH₂ H O S C10.38 ClCH₂ H 3-CHO OCH₂ H O S C10.39 Cl₂CH H 3-CHO OCH₂ H O S C10.40 BrCH₂ H 3-CHO OCH₂ H O S C10.41 FClCH H 3-CHO OCH₂ H O S C10.42 Me H 2-COMe OCH₂ H O S 134-137 C10.43 MeO H 2-COMe OCH₂ H O S C10.44 Me H 3-COMe OCH₂ H O S 233-238 C10.45 MeO H 3-COMe OCH₂ H O S C10.46 Me H 2-NO₂ OCH₂ H O S 191-193 C10.47 Me H 2-NO₂ SCH₂ H O S C10.48 MeO H 2-NO₂ OCH₂ H O S 184-186 C10.49 Me H 2-NO₂ OCH₂ H O O 162-165 C10.50 MeO H 2-NO₂ OCH₂ H O O 130-132 C10.51 Et H 2-NO₂ OCH₂ H O S C10.52 nPr H 2-NO₂ OCH₂ H O S C10.53 iPr H 2-NO₂ OCH₂ H O S C10.54 nBu H 2-NO₂ OCH₂ H O S C10.55 FCH₂ H 2-NO₂ OCH₂ H O S C10.56 F₂CH H 2-NO₂ OCH₂ H O S C10.57 F₃C H 2-NO₂ OCH₂ H O S C10.58 ClCH₂ H 2-NO₂ OCH₂ H O S C10.59 Cl₂CH H 2-NO₂ OCH₂ H O S C10.60 BrCH₂ H 2-NO₂ OCH₂ H O S C10.61 FClCH H 2-NO₂ OCH₂ H O S C10.62 Me H 3-NO₂ OCH₂ H O S 188-190 C10.63 Me H 3-NO₂ SCH₂ H O S C10.64 MeO H 3-NO₂ OCH₂ H O S 198-200 C10.65 Me H 3-NO₂ OCH₂ H O O 148-150 C10.66 MeO H 3-NO₂ OCH₂ H O O 113-115 C10.67 Et H 3-NO₂ OCH₂ H O S C10.68 nPr H 3-NO₂ OCH₂ H O S C10.69 iPr H 3-NO₂ OCH₂ H O S C10.70 nBu H 3-NO₂ OCH₂ H O S C10.71 FCH₂ H 3-NO₂ OCH₂ H O S C10.72 F₂CH H 3-NO₂ OCH₂ H O S C10.73 F₃C H 3-NO₂ OCH₂ H O S C10.74 ClCH₂ H 3-NO₂ OCH₂ H O S C10.75 Cl₂CH H 3-NO₂ OCH₂ H O S C10.76 BrCH₂ H 3-NO₂ OCH₂ H O S C10.77 FClCH H 3-NO₂ OCH₂ H O S C10.78 Me H 2-CO₂Me OCH₂ H O S 192-193 C10.79 MeO H 2-CO₂Me OCH₂ H O S C10.80 Me H 2-CO₂Me OCH₂ H O O C10.81 MeO H 2-CO₂Me OCH₂ H O O C10.82 Me H 2-CO₂Et OCH₂ H O S 140 C10.83 MeO H 2-CO₂Et OCH₂ H O S C10.84 Me H 2-CO₂nPr OCH₂ H O S 127-128 C10.85 MeO H 2-CO₂nPr OCH₂ H O S C10.86 Me H 2-CO₂iPr OCH₂ H O S 127-128 C10.87 MeO H 2-CO₂iPr OCH₂ H O S C10.88 Me H 3-CO₂Me OCH₂ H O S 167-168 C10.89 MeO H 3-CO₂Me OCH₂ H O S C10.90 Me H 3-CO₂Me OCH₂ H O O C10.91 MeO H 3-CO₂Me OCH₂ H O O C10.92 Me H 3-CO₂Et OCH₂ H O S 164-165 C10.93 MeO H 3-CO₂Et OCH₂ H O S C10.94 Me H 3-CO₂nPr OCH₂ H O S 129 C10.95 MeO H 3-CO₂nPr OCH₂ H O S C10.96 Me H 3-CO₂iPr OCH₂ H O S 153.5-155 C10.97 MeO H 3-CO₂iPr OCH₂ H O S C10.98 Me H 2-CHO OCH₂ H O S 174-176 C10.99 Me H 2-CHO SCH₂ H O S C10.100 MeO H 2-CHO OCH₂ H O S C10.101 MeO H 2-CHO OCH₂ H O O C10.102 Et H 2-CHO OCH₂ H O S C10.103 nPr H 2-CHO OCH₂ H O S C10.104 iPr H 2-CHO OCH₂ H O S C10.105 nBu H 2-CHO OCH₂ H O S C10.106 FCH₂ H 2-CHO OCH₂ H O S C10.107 F₂CH H 2-CHO OCH₂ H O S C10.108 F₃C H 2-CHO OCH₂ H O S C10.109 ClCH₂ H 2-CHO OCH₂ H O S C10.110 Cl₂CH H 2-CHO OCH₂ H O S C10.111 BrCH₂ H 2-CHO OCH₂ H O S C10.112 FClCH H 2-CHO OCH₂ H O S C10.113 Me H 3-CHO OCH₂ H O S C10.114 Me H 3-CHO SCH₂ H O S C10.115 MeO H 3-CHO OCH₂ H O S C10.116 Et H 3-CHO OCH₂ H O S C10.117 nPr H 3-CHO OCH₂ H O S C11.1 Me H 2,3-Me₂ OCH₂ H O S 207-209 C11.2 Me H 2,3-Me₂ SCH₂ H O S C11.3 Me H 2,3-Me₂ OCH₂ H O O C11.4 MeO H 2,3-Me₂ OCH₂ H O S 178-180 C11.5 MeO H 2,3-Me₂ OCH₂ H O O C11.6 Et H 2,3-Me₂ OCH₂ H O S C11.7 nPr H 2,3-Me₂ OCH₂ H O S C11.8 iPr H 2,3-Me₂ OCH₂ H O S C11.9 nBu H 2,3-Me₂ OCH₂ H O S C11.10 FCH₂ H 2,3-Me₂ OCH₂ H O S C11.11 F₂CH H 2,3-Me₂ OCH₂ H O S C11.12 F₃C H 2,3-Me₂ OCH₂ H O S C11.13 ClCH₂ H 2,3-Me₂ OCH₂ H O S C11.14 Cl₂CH H 2,3-Me₂ OCH₂ H O S C11.15 BrCH₂ H 2,3-Me₂ OCH₂ H O S C11.16 FClCH H 2,3-Me₂ OCH₂ H O S C11.17 Me H 2,5-Me₂ OCH₂ H O S 90-94 C11.18 Me H 2,5-Me₂ SCH₂ H O S C11.19 Me H 2,5-Me₂ OCH₂ H O O C11.20 MeO H 2,5-Me₂ OCH₂ H O S 127-128 C11.21 MeO H 2,5-Me₂ OCH₂ H O O C11.22 Et H 2,5-Me₂ OCH₂ H O S C11.23 nPr H 2,5-Me₂ OCH₂ H O S C11.24 iPr H 2,5-Me₂ OCH₂ H O S C11.26 FCH₂ H 2,5-Me₂ OCH₂ H O S C11.27 F₂CH H 2,5-Me₂ OCH₂ H O S C11.28 F₃C H 2,5-Me₂ OCH₂ H O S C11.29 ClCH₂ H 2,5-Me₂ OCH₂ H O S C11.30 Cl₂CH H 2,5-Me₂ OCH₂ H O S C11.31 BrCH₂ H 2,5-Me₂ OCH₂ H O S C11.32 FClCH H 2,5-Me₂ OCH₂ H O S C11.33 Me H 2,6-Me₂ OCH₂ H O S 198-204 C11.34 Me H 2,6-Me₂ SCH₂ H O S C11.35 MeO H 2,6-Me₂ OCH₂ H O S C11.36 MeO H 2,6-Me₂ OCH₂ H O O C11.37 Et H 2,6-Me₂ OCH₂ H O S C11.38 nPr H 2,6-Me₂ OCH₂ H O S C11.39 iPr H 2,6-Me₂ OCH₂ H O S C11.40 nBu H 2,6-Me₂ OCH₂ H O S C11.41 FCH₂ H 2,6-Me₂ OCH₂ H O S C11.42 F₂CH H 2,6-Me₂ OCH₂ H O S C11.43 F₃C H 2,6-Me₂ OCH₂ H O S C11.44 ClCH₂ H 2,6-Me₂ OCH₂ H O S C11.45 Cl₂CH H 2,6-Me₂ OCH₂ H O S C11.46 BrCH₂ H 2,6-Me₂ OCH₂ H O S C11.47 FClCH H 2,6-Me₂ OCH₂ H O S C11.48 Me H 3,5-Me₂ OCH₂ H O S 151 C11.49 Me H 3,5-Me₂ SCH₂ H O S C11.50 MeO H 3,5-Me₂ OCH₂ H O S C11.51 MeO H 3,5-Me₂ OCH₂ H O O C11.52 Et H 3,5-Me₂ OCH₂ H O S C11.53 nPr H 3,5-Me₂ OCH₂ H O S C11.54 iPr H 3,5-Me₂ OCH₂ H O S C11.55 nBu H 3,5-Me₂ OCH₂ H O S C11.56 FCH₂ H 3,5-Me₂ OCH₂ H O S C11.57 F₂CH H 3,5-Me₂ OCH₂ H O S C11.58 F₃C H 3,5-Me₂ OCH₂ H O S C11.59 ClCH₂ H 3,5-Me₂ OCH₂ H O S C11.60 Cl₂CH H 3,5-Me₂ OCH₂ H O S C11.61 BrCH₂ H 3,5-Me₂ OCH₂ H O S C11.62 FClCH H 3,5-Me₂ OCH₂ H O S C11.63 Me H 2,3,5-Me₃ OCH₂ H O S 215-220 C11.64 MeO H 2,3,5-Me₃ OCH₂ H O S 158-160 C11.65 Me H 2,3,5-Me₃ OCH₂ H O O C11.66 MeO H 2,3,5-Me₃ OCH₂ H O O C11.67 Et H 2,3,5-Me₃ OCH₂ H O S C11.68 nPr H 2,3,5-Me₃ OCH₂ H O S C11.69 iPr H 2,3,5-Me₃ OCH₂ H O S C11.70 nBu H 2,3,5-Me₃ OCH₂ H O S C11.71 FCH₂ H 2,3,5-Me₃ OCH₂ H O S C11.72 F₂CH H 2,3,5-Me₃ OCH₂ H O S C11.73 F₃C H 2,3,5-Me₃ OCH₂ H O S C11.74 ClCH₂ H 2,3,5-Me₃ OCH₂ H O S C11.75 Cl₂CH H 2,3,5-Me₃ OCH₂ H O S C11.76 BrCH₂ H 2,3,5-Me₃ OCH₂ H O S C11.77 FClCH H 2,3,5-Me₃ OCH₂ H O S C11.78 Me H 2,3,6-Me₃ OCH₂ H O S 217-225 C11.79 MeO H 2,3,6-Me₃ OCH₂ H O S 177-179 C11.80 Me H 2,3,6-Me₃ OCH₂ H O O C11.81 MeO H 2,3,6-Me₃ OCH₂ H O O C11.82 Et H 2,3,6-Me₃ OCH₂ H O S C11.83 nPr H 2,3,6-Me₃ OCH₂ H O S C11.84 iPr H 2,3,6-Me₃ OCH₂ H O S C11.85 nBu H 2,3,6-Me₃ OCH₂ H O S C11.86 FCH₂ H 2,3,6-Me₃ OCH₂ H O S C11.87 F₂CH H 2,3,6-Me₃ OCH₂ H O S C11.88 F₃C H 2,3,6-Me₃ OCH₂ H O S C11.89 ClCH₂ H 2,3,6-Me₃ OCH₂ H O S C11.90 Cl₂CH H 2,3,6-Me₃ OCH₂ H O S C11.91 BrCH₂ H 2,3,6-Me₃ OCH₂ H O S C11.92 FClCH H 2,3,6-Me₃ OCH₂ H O S C11.93 Me H 2,3,5,6-Me₄ OCH₂ H O S C11.94 Et H 2,3,5,6-Me₄ OCH₂ H O S C11.95 nPr H 2,3,5,6-Me₄ OCH₂ H O S C11.96 iPr H 2,3,5,6-Me₄ OCH₂ H O S C11.97 nBu H 2,3,5,6-Me₄ OCH₂ H O S C11.98 FCH₂ H 2,3,5,6-Me₄ OCH₂ H O S C11.99 F₂CH H 2,3,5,6-Me₄ OCH₂ H O S C11.100 F₃C H 2,3,5,6-Me₄ OCH₂ H O S C11.101 ClCH₂ H 2,3,5,6-Me₄ OCH₂ H O S C11.102 Cl₂CH H 2,3,5,6-Me₄ OCH₂ H O S C11.103 BrCH₂ H 2,3,5,6-Me₄ OCH₂ H O S C11.104 FClCH H 2,3,5,6-Me₄ OCH₂ H O S C12.1 Me H 2,3-(OMe)₂ OCH₂ H O S C12.2 Me H 2,3-(OMe)₂ SCH₂ H O S C12.3 MeO H 2,3-(OMe)₂ OCH₂ H O S C12.4 Me H 2,3-(OMe)₂ OCH₂ H O O C12.5 MeO H 2,3-(OMe)₂ OCH₂ H O O C12.6 Et H 2,3-(OMe)₂ OCH₂ H O S C12.7 nPr H 2,3-(OMe)₂ OCH₂ H O S C12.8 iPr H 2,3-(OMe)₂ OCH₂ H O S C12.9 nBu H 2,3-(OMe)₂ OCH₂ H O S C12.10 FCH₂ H 2,3-(OMe)₂ OCH₂ H O S C12.11 F₂CH H 2,3-(OMe)₂ OCH₂ H O S C12.12 F₃C H 2,3-(OMe)₂ OCH₂ H O S C12.13 ClCH₂ H 2,3-(OMe)₂ OCH₂ H O S C12.14 Cl₂CH H 2,3-(OMe)₂ OCH₂ H O S C12.15 BrCH₂ H 2,3-(OMe)₂ OCH₂ H O S C12.16 FClCH H 2,3-(OMe)₂ OCH₂ H O S C12.17 Me H 2,5-(OMe)₂ OCH₂ H O S C12.18 Me H 2,5-(OMe)₂ SCH₂ H O S C12.19 MeO H 2,5-(OMe)₂ OCH₂ H O S C12.20 Et H 2,5-(OMe)₂ OCH₂ H O S C12.21 nPr H 2,5-(OMe)₂ OCH₂ H O S C12.22 iPr H 2,5-(OMe)₂ OCH₂ H O S C12.23 nBu H 2,5-(OMe)₂ OCH₂ H O S C12.24 FCH₂ H 2,5-(OMe)₂ OCH₂ H O S C12.25 F₂CH H 2,5-(OMe)₂ OCH₂ H O S C12.26 F₃C H 2,5-(OMe)₂ OCH₂ H O S C12.27 ClCH₂ H 2,5-(OMe)₂ OCH₂ H O S C12.28 Cl₂CH H 2,5-(OMe)₂ OCH₂ H O S C12.29 BrCH₂ H 2,5-(OMe)₂ OCH₂ H O S C12.30 FClCH H 2,5-(OMe)₂ OCH₂ H O S C12.31 Me H 2,6-(OMe)₂ OCH₂ H O S C12.32 Me H 2,6-(OMe)₂ SCH₂ H O S C12.33 MeO H 2,6-(OMe)₂ OCH₂ H O S C12.34 Et H 2,6-(OMe)₂ OCH₂ H O S C12.35 nPr H 2,6-(OMe)₂ OCH₂ H O S C12.36 iPr H 2,6-(OMe)₂ OCH₂ H O S C12.37 nBu H 2,6-(OMe)₂ OCH₂ H O S C12.38 FCH₂ H 2,6-(OMe)₂ OCH₂ H O S C12.39 F₂CH H 2,6-(OMe)₂ OCH₂ H O S C12.40 F₃C H 2,6-(OMe)₂ OCH₂ H O S C12.41 ClCH₂ H 2,6-(OMe)₂ OCH₂ H O S C12.42 Cl₂CH H 2,6-(OMe)₂ OCH₂ H O S C12.43 BrCH₂ H 2,6-(OMe)₂ OCH₂ H O S C12.44 FClCH H 2,6-(OMe)₂ OCH₂ H O S C12.45 Me H 3,5-(OMe)₂ OCH₂ H O S アモルファス C12.46 Me H 3,5-(OMe)₂ SCH₂ H O S C12.47 MeO H 3,5-(OMe)₂ OCH₂ H O S 110-113 C12.48 Et H 3,5-(OMe)₂ OCH₂ H O S C12.49 nPr H 3,5-(OMe)₂ OCH₂ H O S C12.50 iPr H 3,5-(OMe)₂ OCH₂ H O S C12.51 nBu H 3,5-(OMe)₂ OCH₂ H O S C12.52 FCH₂ H 3,5-(OMe)₂ OCH₂ H O S C12.53 F₂CH H 3,5-(OMe)₂ OCH₂ H O S C12.54 F₃C H 3,5-(OMe)₂ OCH₂ H O S C12.55 ClCH₂ H 3,5-(OMe)₂ OCH₂ H O S C12.56 Cl₂CH H 3,5-(OMe)₂ OCH₂ H O S C12.57 BrCH₂ H 3,5-(OMe)₂ OCH₂ H O S C12.58 FClCH H 3,5-(OMe)₂ OCH₂ H O S C12.59 Me H 2,3,5-(OMe)₃ OCH₂ H O S C12.60 Et H 2,3,5-(OMe)₃ OCH₂ H O S C12.61 nPr H 2,3,5-(OMe)₃ OCH₂ H O S C12.62 iPr H 2,3,5-(OMe)₃ OCH₂ H O S C12.63 nBu H 2,3,5-(OMe)₃ OCH₂ H O S C12.64 FCH₂ H 2,3,5-(OMe)₃ OCH₂ H O S C12.65 F₂CH H 2,3,5-(OMe)₃ OCH₂ H O S C12.66 F₃C H 2,3,5-(OMe)₃ OCH₂ H O S C12.67 ClCH₂ H 2,3,5-(OMe)₃ OCH₂ H O S C12.68 Cl₂CH H 2,3,5-(OMe)₃ OCH₂ H O S C12.69 BrCH₂ H 2,3,5-(OMe)₃ OCH₂ H O S C12.70 FClCH H 2,3,5-(OMe)₃ OCH₂ H O S C12.71 Me H 2,3,6-(OMe)₃ OCH₂ H O S C12.72 Et H 2,3,6-(OMe)₃ OCH₂ H O S C12.73 nPr H 2,3,6-(OMe)₃ OCH₂ H O S C12.74 iPr H 2,3,6-(OMe)₃ OCH₂ H O S C12.75 nBu H 2,3,6-(OMe)₃ OCH₂ H O S C12.76 FCH₂ H 2,3,6-(OMe)₃ OCH₂ H O S C12.77 F₂CH H 2,3,6-(OMe)₃ OCH₂ H O S C12.78 F₃C H 2,3,6-(OMe)₃ OCH₂ H O S C12.79 ClCH₂ H 2,3,6-(OMe)₃ OCH₂ H O S C12.80 Cl₂CH H 2,3,6-(OMe)₃ OCH₂ H O S C12.81 BrCH₂ H 2,3,6-(OMe)₃ OCH₂ H O S C12.82 FClCH H 2,3,6-(OMe)₃ OCH₂ H O S C12.83 Me H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.84 Et H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.85 nPr H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.86 iPr H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.87 nBu H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.88 FCH₂ H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.89 F₂CH H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.90 F₃C H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.91 ClCH₂ H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.92 Cl₂CH H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.93 BrCH₂ H 2,3,5,6-(OMe)₄ OCH₂ H O S C12.94 FClCH H 2,3,5,6-(OMe)₄ OCH₂ H O S C13.1 Me H 2,3-F₂ OCH₂ H O S C13.2 Me H 2,3-F₂ SCH₂ H O S C13.3 Me H 2,3-F₂ OCH₂ H O O C13.4 MeO H 2,3-F₂ OCH₂ H O S C13.5 MeO H 2,3-F₂ OCH₂ H O O C13.6 Et H 2,3-F₂ OCH₂ H O S C13.7 nPr H 2,3-F₂ OCH₂ H O S C13.8 iPr H 2,3-F₂ OCH₂ H O S C13.9 nBu H 2,3-F₂ OCH₂ H O S C13.10 FCH₂ H 2,3-F₂ OCH₂ H O S C13.11 F₂CH H 2,3-F₂ OCH₂ H O S C13.12 F₃C H 2,3-F₂ OCH₂ H O S C13.13 ClCH₂ H 2,3-F₂ OCH₂ H O S C13.14 Cl₂CH H 2,3-F₂ OCH₂ H O S C13.15 BrCH₂ H 2,3-F₂ OCH₂ H O S C13.16 FClCH H 2,3-F₂ OCH₂ H O S C13.17 Me H 2,5-F₂ OCH₂ H O S C13.18 Me H 2,5-F₂ SCH₂ H O S C13.19 MeO H 2,5-F₂ OCH₂ H O S C13.20 Et H 2,5-F₂ OCH₂ H O S C13.21 nPr H 2,5-F₂ OCH₂ H O S C13.22 iPr H 2,5-F₂ OCH₂ H O S C13.23 nBu H 2,5-F₂ OCH₂ H O S C13.24 FCH₂ H 2,5-F₂ OCH₂ H O S C13.25 F₂CH H 2,5-F₂ OCH₂ H O S C13.26 F₃C H 2,5-F₂ OCH₂ H O S C13.27 ClCH₂ H 2,5-F₂ OCH₂ H O S C13.28 Cl₂CH H 2,5-F₂ OCH₂ H O S C13.29 BrCH₂ H 2,5-F₂ OCH₂ H O S C13.30 FClCH H 2,5-F₂ OCH₂ H O S C13.31 Me H 2,6-F₂ OCH₂ H O S C13.32 Me H 2,6-F₂ SCH₂ H O S C13.33 MeO H 2,6-F₂ OCH₂ H O S C13.34 Et H 2,6-F₂ OCH₂ H O S C13.35 nPr H 2,6-F₂ OCH₂ H O S C13.36 iPr H 2,6-F₂ OCH₂ H O S C13.37 nBu H 2,6-F₂ OCH₂ H O S C13.38 FCH₂ H 2,6-F₂ OCH₂ H O S C13.39 F₂CH H 2,6-F₂ OCH₂ H O S C13.40 F₃C H 2,6-F₂ OCH₂ H O S C13.41 ClCH₂ H 2,6-F₂ OCH₂ H O S C13.42 Cl₂CH H 2,6-F₂ OCH₂ H O S C13.43 BrCH₂ H 2,6-F₂ OCH₂ H O S C13.44 FClCH H 2,6-F₂ OCH₂ H O S C13.45 Me H 3,5-F₂ OCH₂ H O S C13.46 Me H 3,5-F₂ SCH₂ H O S C13.47 MeO H 3,5-F₂ OCH₂ H O S C13.48 Et H 3,5-F₂ OCH₂ H O S C13.49 nPr H 3,5-F₂ OCH₂ H O S C13.50 iPr H 3,5-F₂ OCH₂ H O S C13.51 nBu H 3,5-F₂ OCH₂ H O S C13.52 FCH₂ H 3,5-F₂ OCH₂ H O S C13.53 F₂CH H 3,5-F₂ OCH₂ H O S C13.54 F₃C H 3,5-F₂ OCH₂ H O S C13.55 ClCH₂ H 3,5-F₂ OCH₂ H O S C13.56 Cl₂CH H 3,5-F₂ OCH₂ H O S C13.57 BrCH₂ H 3,5-F₂ OCH₂ H O S C13.58 FClCH H 3,5-F₂ OCH₂ H O S C13.59 Me H 2,3,5-F₃ OCH₂ H O S C13.60 Et H 2,3,5-F₃ OCH₂ H O S C13.61 nPr H 2,3,5-F₃ OCH₂ H O S C13.62 iPr H 2,3,5-F₃ OCH₂ H O S C13.63 nBu H 2,3,5-F₃ OCH₂ H O S C13.64 FCH₂ H 2,3,5-F₃ OCH₂ H O S C13.65 F₂CH H 2,3,5-F₃ OCH₂ H O S C13.66 F₃C H 2,3,5-F₃ OCH₂ H O S C13.67 ClCH₂ H 2,3,5-F₃ OCH₂ H O S C13.68 Cl₂CH H 2,3,5-F₃ OCH₂ H O S C13.69 BrCH₂ H 2,3,5-F₃ OCH₂ H O S C13.70 FClCH H 2,3,5-F₃ OCH₂ H O S C13.71 Me H 2,3,6-F₃ OCH₂ H O S C13.72 Et H 2,3,6-F₃ OCH₂ H O S C13.73 nPr H 2,3,6-F₃ OCH₂ H O S C13.74 iPr H 2,3,6-F₃ OCH₂ H O S C13.75 nBu H 2,3,6-F₃ OCH₂ H O S C13.76 FCH₂ H 2,3,6-F₃ OCH₂ H O S C13.77 F₂CH H 2,3,6-F₃ OCH₂ H O S C13.78 F₃C H 2,3,6-F₃ OCH₂ H O S C13.79 ClCH₂ H 2,3,6-F₃ OCH₂ H O S C13.80 Cl₂CH H 2,3,6-F₃ OCH₂ H O S C13.81 BrCH₂ H 2,3,6-F₃ OCH₂ H O S C13.82 FClCH H 2,3,6-F₃ OCH₂ H O S C13.83 Me H 2,3,5,6-F₄ OCH₂ H O S C13.84 Et H 2,3,5,6-F₄ OCH₂ H O S C13.85 nPr H 2,3,5,6-F₄ OCH₂ H O S C13.86 iPr H 2,3,5,6-F₄ OCH₂ H O S C13.87 nBu H 2,3,5,6-F₄ OCH₂ H O S C13.88 FCH₂ H 2,3,5,6-F₄ OCH₂ H O S C13.89 F₂CH H 2,3,5,6-F₄ OCH₂ H O S C13.90 F₃C H 2,3,5,6-F₄ OCH₂ H O S C13.91 ClCH₂ H 2,3,5,6-F₄ OCH₂ H O S C13.92 Cl₂CH H 2,3,5,6-F₂ OCH₂ H O S C13.93 BrCH₂ H 2,3,5,6-F₄ OCH₂ H O S C13.94 FClCH H 2,3,5,6-F₄ OCH₂ H O S C14.1 Me H 2,3-Cl₂ OCH₂ H O S C14.2 Me H 2,3-Cl₂ SCH₂ H O S C14.3 MeO H 2,3-Cl₂ OCH₂ H O S C14.4 Et H 2,3-Cl₂ OCH₂ H O S C14.5 nPr H 2,3-Cl₂ OCH₂ H O S C14.6 iPr H 2,3-Cl₂ OCH₂ H O S C14.7 nBu H 2,3-Cl₂ OCH₂ H O S C14.8 FCH₂ H 2,3-Cl₂ OCH₂ H O S C14.9 F₂CH H 2,3-Cl₂ OCH₂ H O S C14.10 F₃C H 2,3-Cl₂ OCH₂ H O S C14.11 ClCH₂ H 2,3-Cl₂ OCH₂ H O S C14.12 Cl₂CH H 2,3-Cl₂ OCH₂ H O S C14.13 BrCH₂ H 2,3-Cl₂ OCH₂ H O S C14.14 FClCH H 2,3-Cl₂ OCH₂ H O S C14.15 Me H 2,5-Cl₂ OCH₂ H O S 188 C14.16 Me H 2,5-Cl₂ SCH₂ H O S C14.17 Me H 2,5-Cl₂ OCH₂ H O O C14.18 MeO H 2,5-Cl₂ OCH₂ H O S 131-133 C14.19 MeO H 2,5-Cl₂ OCH₂ H O O C14.20 Et H 2,5-Cl₂ OCH₂ H O S C14.21 nPr H 2,5-Cl₂ OCH₂ H O S C14.22 iPr H 2,5-Cl₂ OCH₂ H O S C14.23 nBu H 2,5-Cl₂ OCH₂ H O S C14.24 FCH₂ H 2,5-Cl₂ OCH₂ H O S C14.25 F₂CH H 2,5-Cl₂ OCH₂ H O S C14.26 F₃C H 2,5-Cl₂ OCH₂ H O S C14.27 ClCH₂ H 2,5-Cl₂ OCH₂ H O S C14.28 Cl₂CH H 2,5-Cl₂ OCH₂ H O S C14.29 BrCH₂ H 2,5-Cl₂ OCH₂ H O S C14.30 FClCH H 2,5-Cl₂ OCH₂ H O S C14.31 Me H 2,6-Cl₂ OCH₂ H O S 169-172 C14.32 Me H 2,6-Cl₂ SCH₂ H O S C14.33 MeO H 2,6-Cl₂ OCH₂ H O S C14.34 Et H 2,6-Cl₂ OCH₂ H O S C14.35 nPr H 2,6-Cl₂ OCH₂ H O S C14.36 iPr H 2,6-Cl₂ OCH₂ H O S C14.37 nBu H 2,6-Cl₂ OCH₂ H O S C14.38 FCH₂ H 2,6-Cl₂ OCH₂ H O S C14.39 F₂CH H 2,6-Cl₂ OCH₂ H O S C14.40 F₃C H 2,6-Cl₂ OCH₂ H O S C14.41 ClCH₂ H 2,6-Cl₂ OCH₂ H O S C14.42 Cl₂CH H 2,6-Cl₂ OCH₂ H O S C14.43 BrCH₂ H 2,6-Cl₂ OCH₂ H O S C14.44 FClCH H 2,6-Cl₂ OCH₂ H O S C14.45 Me H 3,5-Cl₂ OCH₂ H O S 173.5-175 C14.46 Me H 3,5-Cl₂ SCH₂ H O S C14.47 Me H 3,5-Cl₂ OCH₂ H O O C14.48 MeO H 3,5-Cl₂ OCH₂ H O S C14.49 MeO H 3,5-Cl₂ SCH₂ H O S C14.50 MeO H 3,5-Cl₂ OCH₂ H O O C14.51 Et H 3,5-Cl₂ OCH₂ H O S C14.52 nPr H 3,5-Cl₂ OCH₂ H O S C14.53 iPr H 3,5-Cl₂ OCH₂ H O S C14.54 nBu H 3,5-Cl₂ OCH₂ H O S C14.55 FCH₂ H 3,5-Cl₂ OCH₂ H O S C14.56 F₂CH H 3,5-Cl₂ OCH₂ H O S C14.57 F₃C H 3,5-Cl₂ OCH₂ H O S C14.58 ClCH₂ H 3,5-Cl₂ OCH₂ H O S C14.59 Cl₂CH H 3,5-Cl₂ OCH₂ H O S C14.60 BrCH₂ H 3,5-Cl₂ OCH₂ H O S C14.61 FClCH H 3,5-Cl₂ OCH₂ H O S C14.62 Me H 2,3,5-Cl₃ OCH₂ H O S C14.63 Et H 2,3,5-Cl₃ OCH₂ H O S C14.64 nPr H 2,3,5-Cl₃ OCH₂ H O S C14.65 iPr H 2,3,5-Cl₃ OCH₂ H O S C14.66 nBu H 2,3,5-Cl₃ OCH₂ H O S C14.67 FCH₂ H 2,3,5-Cl₃ OCH₂ H O S C14.68 F₂CH H 2,3,5-Cl₃ OCH₂ H O S C14.69 F₃C H 2,3,5-Cl₃ OCH₂ H O S C14.70 ClCH₂ H 2,3,5-Cl₃ OCH₂ H O S C14.71 Cl₂CH H 2,3,5-Cl₃ OCH₂ H O S C14.72 BrCH₂ H 2,3,5-Cl₃ OCH₂ H O S C14.73 FClCH H 2,3,5-Cl₃ OCH₂ H O S C14.74 Me H 2,3,6-Cl₃ OCH₂ H O S 194-197 C14.75 MeO H 2,3,6-Cl₃ OCH₂ H O S C14.76 Et H 2,3,6-Cl₃ OCH₂ H O S C14.77 nPr H 2,3,6-Cl₃ OCH₂ H O S C14.78 iPr H 2,3,6-Cl₃ OCH₂ H O S C14.79 nBu H 2,3,6-Cl₃ OCH₂ H O S C14.80 FCH₂ H 2,3,6-Cl₃ OCH₂ H O S C14.81 F₂CH H 2,3,6-Cl₃ OCH₂ H O S C14.82 F₃C H 2,3,6-Cl₃ OCH₂ H O S C14.83 ClCH₂ H 2,3,6-Cl₃ OCH₂ H O S C14.84 Cl₂CH H 2,3,6-Cl₃ OCH₂ H O S C14.85 BrCH₂ H 2,3,6-Cl₃ OCH₂ H O S C14.86 FClCH H 2,3,6-Cl₃ OCH₂ H O S C14.87 Me H 2,3,5,6-Cl₄ OCH₂ H O S C14.88 Et H 2,3,5,6-Cl₄ OCH₂ H O S C14.89 nPr H 2,3,5,6-Cl₄ OCH₂ H O S C14.90 iPr H 2,3,5,6-Cl₄ OCH₂ H O S C14.91 nBu H 2,3,5,6-Cl₄ OCH₂ H O S C14.92 FCH₂ H 2,3,5,6-Cl₄ OCH₂ H O S C14.93 F₂CH H 2,3,5,6-Cl₄ OCH₂ H O S C14.94 F₃C H 2,3,5,6-Cl₄ OCH₂ H O S C14.95 ClCH₂ H 2,3,5,6-Cl₄ OCH₂ H O S C14.96 Cl₂CH H 2,3,5,6-Cl₄ OCH₂ H O S C14.97 BrCH₂ H 2,3,5,6-Cl₄ OCH₂ H O S C14.98 FClCH H 2,3,5,6-Cl₄ OCH₂ H O S C15.1 Me H 2,3-Br₂ OCH₂ H O S C15.2 Et H 2,3-Br₂ OCH₂ H O S C15.3 nPr H 2,3-Br₂ OCH₂ H O S C15.4 iPr H 2,3-Br₂ OCH₂ H O S C15.5 nBu H 2,3-Br₂ OCH₂ H O S C15.6 FCH₂ H 2,3-Br₂ OCH₂ H O S C15.7 F₂CH H 2,3-Br₂ OCH₂ H O S C15.8 F₃C H 2,3-Br₂ OCH₂ H O S C15.9 ClCH₂ H 2,3-Br₂ OCH₂ H O S C15.10 Cl₂CH H 2,3-Br₂ OCH₂ H O S C15.11 BrCH₂ H 2,3-Br₂ OCH₂ H O S C15.12 FClCH H 2,3-Br₂ OCH₂ H O S C15.13 Me H 2,5-Br₂ OCH₂ H O S C15.14 Et H 2,5-Br₂ OCH₂ H O S C15.15 nPr H 2,5-Br₂ OCH₂ H O S C15.16 iPr H 2,5-Br₂ OCH₂ H O S C15.17 nBu H 2,5-Br₂ OCH₂ H O S C15.18 FCH₂ H 2,5-Br₂ OCH₂ H O S C15.19 F₂CH H 2,5-Br₂ OCH₂ H O S C15.20 F₃C H 2,5-Br₂ OCH₂ H O S C15.21 ClCH₂ H 2,5-Br₂ OCH₂ H O S C15.22 Cl₂CH H 2,5-Br₂ OCH₂ H O S C15.23 BrCH₂ H 2,5-Br₂ OCH₂ H O S C15.24 FClCH H 2,5-Br₂ OCH₂ H O S C15.25 Me H 2,6-Br₂ OCH₂ H O S C15.26 Et H 2,6-Br₂ OCH₂ H O S C15.27 nPr H 2,6-Br₂ OCH₂ H O S C15.28 iPr H 2,6-Br₂ OCH₂ H O S C15.29 nBu H 2,6-Br₂ OCH₂ H O S C15.30 FCH₂ H 2,6-Br₂ OCH₂ H O S C15.31 F₂CH H 2,6-Br₂ OCH₂ H O S C15.32 F₃C H 2,6-Br₂ OCH₂ H O S C15.33 ClCH₂ H 2,6-Br₂ OCH₂ H O S C15.34 Cl₂CH H 2,6-Br₂ OCH₂ H O S C15.35 BrCH₂ H 2,6-Br₂ OCH₂ H O S C15.36 FClCH H 2,6-Br₂ OCH₂ H O S C15.37 Me H 3,5-Br₂ OCH₂ H O S 198(分解) C15.38 MeO H 3,5-Br₂ OCH₂ H O S C15.39 Et H 3,5-Br₂ OCH₂ H O S C15.40 nPr H 3,5-Br₂ OCH₂ H O S C15.41 iPr H 3,5-Br₂ OCH₂ H O S C15.42 nBu H 3,5-Br₂ OCH₂ H O S C15.43 FCH₂ H 3,5-Br₂ OCH₂ H O S C15.44 F₂CH H 3,5-Br₂ OCH₂ H O S C15.45 F₃C H 3,5-Br₂ OCH₂ H O S C15.46 ClCH₂ H 3,5-Br₂ OCH₂ H O S C15.47 Cl₂CH H 3,5-Br₂ OCH₂ H O S C15.48 BrCH₂ H 3,5-Br₂ OCH₂ H O S C15.49 FClCH H 3,5-Br₂ OCH₂ H O S C15.50 Me H 2,3,5-Br₃ OCH₂ H O S C15.51 Et H 2,3,5-Br₃ OCH₂ H O S C15.52 nPr H 2,3,5-Br₃ OCH₂ H O S C15.53 iPr H 2,3,5-Br₃ OCH₂ H O S C15.54 nBu H 2,3,5-Br₃ OCH₂ H O S C15.55 FCH₂ H 2,3,5-Br₃ OCH₂ H O S C15.56 F₂CH H 2,3,5-Br₃ OCH₂ H O S C15.57 F₃C H 2,3,5-Br₃ OCH₂ H O S C15.58 ClCH₂ H 2,3,5-Br₃ OCH₂ H O S C15.59 Cl₂CH H 2,3,5-Br₃ OCH₂ H O S C15.60 BrCH₂ H 2,3,5-Br₃ OCH₂ H O S C15.61 FClCH H 2,3,5-Br₃ OCH₂ H O S C15.62 Me H 2,3,6-Br₃ OCH₂ H O S C15.63 Et H 2,3,6-Br₃ OCH₂ H O S C15.64 nPr H 2,3,6-Br₃ OCH₂ H O S C15.65 iPr H 2,3,6-Br₃ OCH₂ H O S C15.66 nBu H 2,3,6-Br₃ OCH₂ H O S C15.67 FCH₂ H 2,3,6-Br₃ OCH₂ H O S C15.68 F₂CH H 2,3,6-Br₃ OCH₂ H O S C15.69 F₃C H 2,3,6-Br₃ OCH₂ H O S C15.70 ClCH₂ H 2,3,6-Br₃ OCH₂ H O S C15.71 Cl₂CH H 2,3,6-Br₃ OCH₂ H O S C15.72 BrCH₂ H 2,3,6-Br₃ OCH₂ H O S C15.73 FClCH H 2,3,6-Br₃ OCH₂ H O S C15.74 Me H 2,3,5,6-Br₄ OCH₂ H O S C15.75 Et H 2,3,5,6-Br₄ OCH₂ H O S C15.76 nPr H 2,3,5,6-Br₄ OCH₂ H O S C15.77 iPr H 2,3,5,6-Br₄ OCH₂ H O S C15.78 nBu H 2,3,5,6-Br₄ OCH₂ H O S C15.79 FCH₂ H 2,3,5,6-Br₄ OCH₂ H O S C15.80 F₂CH H 2,3,5,6-Br₄ OCH₂ H O S C15.81 F₃C H 2,3,5,6-Br₄ OCH₂ H O S C15.82 ClCH₂ H 2,3,5,6-Br₄ OCH₂ H O S C15.83 Cl₂CH H 2,3,5,6-Br₄ OCH₂ H O S C15.84 BrCH₂ H 2,3,5,6-Br₄ OCH₂ H O S C15.85 FClCH H 2,3,5,6-Br₄ OCH₂ H O S C16.1 Me H 2-F,3-Me OCH₂ H O S C16.2 Me H 2-F,3-Me SCH₂ H O S C16.3 Et H 2-F,3-Me OCH₂ H O S C16.4 nPr H 2-F,3-Me OCH₂ H O S C16.5 iPr H 2-F,3-Me OCH₂ H O S C16.6 nBu H 2-F,3-Me OCH₂ H O S C16.7 FCH₂ H 2-F,3-Me OCH₂ H O S C16.8 F₂CH H 2-F,3-Me OCH₂ H O S C16.9 F₃C H 2-F,3-Me OCH₂ H O S C16.10 ClCH₂ H 2-F,3-Me OCH₂ H O S C16.11 Cl₂CH H 2-F,3-Me OCH₂ H O S C16.12 Me H 2-F,5-Me OCH₂ H O S C16.13 Me H 2-F,5-Me SCH₂ H O S C16.14 Et H 2-F,5-Me OCH₂ H O S C16.15 nPr H 2-F,5-Me OCH₂ H O S C16.16 iPr H 2-F,5-Me OCH₂ H O S C16.17 nBu H 2-F,5-Me OCH₂ H O S C16.18 FCH₂ H 2-F,5-Me OCH₂ H O S C16.19 F₂CH H 2-F,5-Me OCH₂ H O S C16.20 F₃C H 2-F,5-Me OCH₂ H O S C16.21 ClCH₂ H 2-F,5-Me OCH₂ H O S C16.22 Cl₂CH H 2-F,5-Me OCH₂ H O S C16.23 Me H 3-F,5-Me OCH₂ H O S C16.24 Me H 3-F,5-Me SCH₂ H O S C16.25 Et H 3-F,5-Me OCH₂ H O S C16.26 nPr H 3-F,5-Me OCH₂ H O S C16.27 iPr H 3-F,5-Me OCH₂ H O S C16.28 nBu H 3-F,5-Me OCH₂ H O S C16.29 FCH₂ H 3-F,5-Me OCH₂ H O S C16.30 F₂CH H 3-F,5-Me OCH₂ H O S C16.31 F₃C H 3-F,5-Me OCH₂ H O S C16.32 ClCH₂ H 3-F,5-Me OCH₂ H O S C16.33 Cl₂CH H 3-F,5-Me OCH₂ H O S C16.34 Me H 2-Me,3-F OCH₂ H O S C16.35 Me H 2-Me,3-F SCH₂ H O S C16.36 Et H 2-Me,3-F OCH₂ H O S C16.37 nPr H 2-Me,3-F OCH₂ H O S C16.38 iPr H 2-Me,3-F OCH₂ H O S C16.39 nBu H 2-Me,3-F OCH₂ H O S C16.40 FCH₂ H 2-Me,3-F OCH₂ H O S C16.41 F₂CH H 2-Me,3-F OCH₂ H O S C16.42 F₃C H 2-Me,3-F OCH₂ H O S C16.44 Cl₂CH H 3-F,2-Me OCH₂ H O S C16.45 Me H 2-F,6-Me OCH₂ H O S C16.46 Me H 2-F,6-Me SCH₂ H O S C16.47 Et H 2-F,6-Me OCH₂ H O S C16.48 nPr H 2-F,6-Me OCH₂ H O S C16.49 iPr H 2-F,6-Me OCH₂ H O S C16.50 nBu H 2-F,6-Me OCH₂ H O S C16.51 FCH₂ H 2-F,6-Me OCH₂ H O S C16.52 F₂CH H 2-F,6-Me OCH₂ H O S C16.53 F₃C H 2-F,6-Me OCH₂ H O S C16.54 ClCH₂ H 2-F,6-Me OCH₂ H O S C16.55 Cl₂CH H 2-F,6-Me OCH₂ H O S C16.56 Me H 2-Me,5-F OCH₂ H O S C16.57 Me H 2-Me,5-F SCH₂ H O S C16.58 Et H 2-Me,5-F OCH₂ H O S C16.59 nPr H 2-Me,5-F OCH₂ H O S C16.60 iPr H 2-Me,5-F OCH₂ H O S C16.61 nBu H 2-Me,5-F OCH₂ H O S C16.62 FCH₂ H 2-Me,5-F OCH₂ H O S C16.63 F₂CH H 2-Me,5-F OCH₂ H O S C16.64 F₃C H 2-Me,5-F OCH₂ H O S C16.65 ClCH₂ H 2-Me,5-F OCH₂ H O S C16.66 Cl₂CH H 2-Me,5-F OCH₂ H O S C16.67 Me H 2-Cl,3-Me OCH₂ H O S C16.68 Me H 2-Cl,3-Me SCH₂ H O S C16.69 Et H 2-Cl,3-Me OCH₂ H O S C16.70 nPr H 2-Cl,3-Me OCH₂ H O S C16.71 iPr H 2-Cl,3-Me OCH₂ H O S C16.72 nBu H 2-Cl,3-Me OCH₂ H O S C16.73 FCH₂ H 2-Cl,3-Me OCH₂ H O S C16.74 F₂CH H 2-Cl,3-Me OCH₂ H O S C16.75 F₃C H 2-Cl,3-Me OCH₂ H O S C16.76 ClCH₂ H 2-Cl,3-Me OCH₂ H O S C16.77 Cl₂CH H 2-Cl,3-Me OCH₂ H O S C16.78 Me H 2-Cl,5-Me OCH₂ H O S C16.79 Me H 2-Cl,5-Me SCH₂ H O S C16.80 Et H 2-Cl,5-Me OCH₂ H O S C16.81 nPr H 2-Cl,5-Me OCH₂ H O S C16.82 iPr H 2-Cl,5-Me OCH₂ H O S C16.83 nBu H 2-Cl,5-Me OCH₂ H O S C16.84 FCH₂ H 2-Cl,5-Me OCH₂ H O S C16.85 F₂CH H 2-Cl,5-Me OCH₂ H O S C16.86 F₃C H 2-Cl,5-Me OCH₂ H O S C16.87 ClCH₂ H 2-Cl,5-Me OCH₂ H O S C16.88 Cl₂CH H 2-Cl,5-Me OCH₂ H O S C16.89 Me H 3-Cl,5-Me OCH₂ H O S C16.90 Me H 3-Cl,5-Me SCH₂ H O S C16.91 Et H 3-Cl,5-Me OCH₂ H O S C16.92 nPr H 3-Cl,5-Me OCH₂ H O S C16.93 iPr H 3-Cl,5-Me OCH₂ H O S C16.94 nBu H 3-Cl,5-Me OCH₂ H O S C16.95 FCH₂ H 3-Cl,5-Me OCH₂ H O S C16.96 F₂CH H 3-Cl,5-Me OCH₂ H O S C16.97 F₃C H 3-Cl,5-Me OCH₂ H O S C16.98 ClCH₂ H 3-Cl,5-Me OCH₂ H O S C16.99 Cl₂CH H 3-Cl,5-Me OCH₂ H O S C16.100 Me H 2-Me,3-Cl OCH₂ H O S C16.101 Me H 2-Me,3-Cl SCH₂ H O S C16.102 Et H 2-Me,3-Cl OCH₂ H O S C16.103 nPr H 2-Me,3-Cl OCH₂ H O S C16.104 iPr H 2-Me,3-Cl OCH₂ H O S C16.105 nBu H 2-Me,3-Cl OCH₂ H O S C16.106 FCH₂ H 2-Me,3-Cl OCH₂ H O S C16.107 F₂CH H 2-Me,3-Cl OCH₂ H O S C16.108 F₃C H 2-Me,3-Cl OCH₂ H O S C16.109 ClCH₂ H 2-Me,3-Cl OCH₂ H O S C16.110 Cl₂CH H 2-Me,3-Cl OCH₂ H O S C16.111 Me H 2-Cl,6-Me OCH₂ H O S C16.112 Me H 2-Cl,6-Me SCH₂ H O S C16.113 MeO H 2-Cl,6-Me OCH₂ H O S 184-187 C16.114 MeO H 2-Cl,6-Me OCH₂ H O O C16.115 Et H 2-Cl,6-Me OCH₂ H O S C16.116 nPr H 2-Cl,6-Me OCH₂ H O S C16.117 iPr H 2-Cl,6-Me OCH₂ H O S C16.118 nBu H 2-Cl,6-Me OCH₂ H O S C16.119 FCH₂ H 2-Cl,6-Me OCH₂ H O S C16.120 F₂CH H 2-Cl,6-Me OCH₂ H O S C16.121 F₃C H 2-Cl,6-Me OCH₂ H O S C16.122 ClCH₂ H 2-Cl,6-Me OCH₂ H O S C16.123 Cl₂CH H 2-Cl,6-Me OCH₂ H O S C16.124 Me H 2-Me,5-Cl OCH₂ H O S C16.125 Me H 2-Me,5-Cl SCH₂ H O S C16.126 MeO H 2-Me,5-Cl OCH₂ H O S 138-141 C16.127 MeO H 2-Me,5-Cl OCH₂ H O O C16.128 Et H 2-Me,5-Cl OCH₂ H O S C16.129 nPr H 2-Me,5-Cl OCH₂ H O S C16.130 iPr H 2-Me,5-Cl OCH₂ H O S C16.131 nBu H 2-Me,5-Cl OCH₂ H O S C16.132 FCH₂ H 2-Me,5-Cl OCH₂ H O S C16.133 F₂CH H 2-Me,5-Cl OCH₂ H O S C16.134 F₃C H 2-Me,5-Cl OCH₂ H O S C16.135 ClCH₂ H 2-Me,5-Cl OCH₂ H O S C16.136 Cl₂CH H 2-Me,5-Cl OCH₂ H O S C17.1 Me H 2-F,3-Cl OCH₂ H O S C17.2 Me H 2-F,3-Cl SCH₂ H O S C17.3 Et H 2-F,3-Cl OCH₂ H O S C17.4 nPr H 2-F,3-Cl OCH₂ H O S C17.5 iPr H 2-F,3-Cl OCH₂ H O S C17.6 nBu H 2-F,3-Cl OCH₂ H O S C17.7 FCH₂ H 2-F,3-Cl OCH₂ H O S C17.8 F₂CH H 2-F,3-Cl OCH₂ H O S C17.9 F₃C H 2-F,3-Cl OCH₂ H O S C17.10 ClCH₂ H 2-F,3-Cl OCH₂ H O S C17.11 Cl₂CH H 2-F,3-Cl OCH₂ H O S C17.12 Me H 2-F,5-Cl OCH₂ H O S C17.13 Me H 2-F,5-Cl SCH₂ H O S C17.14 Et H 2-F,5-Cl OCH₂ H O S C17.15 nPr H 2-F,5-Cl OCH₂ H O S C17.16 iPr H 2-F,5-Cl OCH₂ H O S C17.18 nBu H 2-F,5-Cl OCH₂ H O S C17.19 FCH₂ H 2-F,5-Cl OCH₂ H O S C17.20 F₂CH H 2-F,5-Cl OCH₂ H O S C17.21 F₃C H 2-F,5-Cl OCH₂ H O S C17.22 ClCH₂ H 2-F,5-Cl OCH₂ H O S C17.23 Cl₂CH H 2-F,5-Cl OCH₂ H O S C17.24 Me H 3-Cl,5-F OCH₂ H O S C17.25 Me H 3-Cl,5-F SCH₂ H O S C17.26 Et H 3-Cl,5-F OCH₂ H O S C17.27 nPr H 3-Cl,5-F OCH₂ H O S C17.28 iPr H 3-Cl,5-F OCH₂ H O S C17.29 nBu H 3-Cl,5-F OCH₂ H O S C17.30 FCH₂ H 3-Cl,5-F OCH₂ H O S C17.31 F₂CH H 3-Cl,5-F OCH₂ H O S C17.32 F₃C H 3-Cl,5-F OCH₂ H O S C17.33 ClCH₂ H 3-Cl,5-F OCH₂ H O S C17.34 Cl₂CH H 3-Cl,5-F OCH₂ H O S C17.35 Me H 2-Cl,3-F OCH₂ H O S C17.36 Me H 2-Cl,3-F SCH₂ H O S C17.37 Et H 2-Cl,3-F OCH₂ H O S C17.38 nPr H 2-Cl,3-F OCH₂ H O S C17.39 iPr H 2-Cl,3-F OCH₂ H O S C17.40 nBu H 2-Cl,3-F OCH₂ H O S C17.41 FCH₂ H 2-Cl,3-F OCH₂ H O S C17.42 F₂CH H 2-Cl,3-F OCH₂ H O S C17.43 F₃C H 2-Cl,3-F OCH₂ H O S C17.44 ClCH₂ H 2-Cl,3-F OCH₂ H O S C17.45 Cl₂CH H 2-Cl,3-F OCH₂ H O S C17.46 Me H 2-Cl,6-F OCH₂ H O S C17.47 Me H 2-Cl,6-F SCH₂ H O S C17.48 Et H 2-Cl,6-F OCH₂ H O S C17.49 nPr H 2-Cl,6-F OCH₂ H O S C17.50 iPr H 2-Cl,6-F OCH₂ H O S C17.51 nBu H 2-Cl,6-F OCH₂ H O S C17.52 FCH₂ H 2-Cl,6-F OCH₂ H O S C17.53 F₂CH H 2-Cl,6-F OCH₂ H O S C17.54 F₃C H 2-Cl,6-F OCH₂ H O S C17.55 ClCH₂ H 2-Cl,6-F OCH₂ H O S C17.56 Cl₂CH H 2-Cl,6-F OCH₂ H O S C17.57 Me H 2-Cl,5-F OCH₂ H O S C17.58 Me H 2-Cl,5-F SCH₂ H O S C17.59 Et H 2-Cl,5-F OCH₂ H O S C17.60 nPr H 2-Cl,5-F OCH₂ H O S C17.61 iPr H 2-Cl,5-F OCH₂ H O S C17.62 nBu H 2-Cl,5-F OCH₂ H O S C17.63 FCH₂ H 2-Cl,5-F OCH₂ H O S C17.64 F₂CH H 2-Cl,5-F OCH₂ H O S C17.65 F₃C H 2-Cl,5-F OCH₂ H O S C17.66 ClCH₂ H 2-Cl,5-F OCH₂ H O S C17.67 Cl₂CH H 2-Cl,5-F OCH₂ H O S C17.68 Me H 2-CF₃,3-Me OCH₂ H O S C17.69 Me H 2-CF₃,3-Me SCH₂ H O S C17.70 Et H 2-CF₃,3-Me OCH₂ H O S C17.71 nPr H 2-CF₃,3-Me OCH₂ H O S C17.72 iPr H 2-CF₃,3-Me OCH₂ H O S C17.73 nBu H 2-CF₃,3-Me OCH₂ H O S C17.74 FCH₂ H 2-CF₃,3-Me OCH₂ H O S C17.75 F₂CH H 2-CF₃,3-Me OCH₂ H O S C17.76 F₃C H 2-CF₃,3-Me OCH₂ H O S C17.77 ClCH₂ H 2-CF₃,3-Me OCH₂ H O S C17.78 Cl₂CH H 2-CF₃,3-Me OCH₂ H O S C17.79 Me H 2-CF₃,5-Me OCH₂ H O S C17.80 Me H 2-CF₃,5-Me SCH₂ H O S C17.81 Et H 2-CF₃,5-Me OCH₂ H O S C17.82 nPr H 2-CF₃,5-Me OCH₂ H O S C17.83 iPr H 2-CF₃,5-Me OCH₂ H O S C17.84 nBu H 2-CF₃,5-Me OCH₂ H O S C17.85 FCH₂ H 2-CF₃,5-Me OCH₂ H O S C17.86 F₂CH H 2-CF₃,5-Me OCH₂ H O S C17.87 F₃C H 2-CF₃,5-Me OCH₂ H O S C17.88 ClCH₂ H 2-CF₃,5-Me OCH₂ H O S C17.89 Cl₂CH H 2-CF₃,5-Me OCH₂ H O S C17.90 Me H 3-CF₃,5-Me OCH₂ H O S C17.91 Me H 3-CF₃,5-Me SCH₂ H O S C17.92 Et H 3-CF₃,5-Me OCH₂ H O S C17.93 nPr H 3-CF₃,5-Me OCH₂ H O S C17.94 iPr H 3-CF₃,5-Me OCH₂ H O S C17.95 nBu H 3-CF₃,5-Me OCH₂ H O S C17.96 FCH₂ H 3-CF₃,5-Me OCH₂ H O S C17.97 F₂CH H 3-CF₃,5-Me OCH₂ H O S C17.98 F₃C H 3-CF₃,5-Me OCH₂ H O S C17.99 ClCH₂ H 3-CF₃,5-Me OCH₂ H O S C17.100 Cl₂CH H 3-CF₃,5-Me OCH₂ H O S C17.101 Me H 2-Me,3-CF₃ OCH₂ H O S C17.102 Me H 2-Me,3-CF₃ SCH₂ H O S C17.103 Et H 2-Me,3-CF₃ OCH₂ H O S C17.104 nPr H 2-Me,3-CF₃ OCH₂ H O S C17.105 iPr H 2-Me,3-CF₃ OCH₂ H O S C17.106 nBu H 2-Me,3-CF₃ OCH₂ H O S C17.107 FCH₂ H 2-Me,3-CF₃ OCH₂ H O S C17.108 F₂CH H 2-Me,3-CF₃ OCH₂ H O S C17.109 F₃C H 2-Me,3-CF₃ OCH₂ H O S C17.110 ClCH₂ H 2-Me,3-CF₃ OCH₂ H O S C17.111 Cl₂CH H 2-Me,3-CF₃ OCH₂ H O S C17.112 Me H 2-CF₃,6-Me OCH₂ H O S C17.113 Me H 2-CF₃,6-Me SCH₂ H O S C17.114 Et H 2-CF₃,6-Me OCH₂ H O S C17.115 nPr H 2-CF₃,6-Me OCH₂ H O S C17.116 iPr H 2-CF₃,6-Me OCH₂ H O S C17.117 nBu H 2-CF₃,6-Me OCH₂ H O S C17.118 FCH₂ H 2-CF₃,6-Me OCH₂ H O S C17.119 F₂CH H 2-CF₃,6-Me OCH₂ H O S C17.120 F₃C H 2-CF₃,6-Me OCH₂ H O S C17.121 ClCH₂ H 2-CF₃,6-Me OCH₂ H O S C17.122 Cl₂CH H 2-CF₃,6-Me OCH₂ H O S C17.123 Me H 2-Me,5-CF₃ OCH₂ H O S C17.124 Me H 2-Me,5-CF₃ SCH₂ H O S C17.125 Et H 2-Me,5-CF₃ OCH₂ H O S C17.126 nPr H 2-Me,5-CF₃ OCH₂ H O S C17.127 iPr H 2-Me,5-CF₃ OCH₂ H O S C17.128 nBu H 2-Me,5-CF₃ OCH₂ H O S C17.129 FCH₂ H 2-Me,5-CF₃ OCH₂ H O S C17.130 F₂CH H 2-Me,5-CF₃ OCH₂ H O S C17.131 F₃C H 2-Me,5-CF₃ OCH₂ H O S C17.132 ClCH₂ H 2-Me,5-CF₃ OCH₂ H O S C17.133 Cl₂CH H 2-Me,5-CF₃ OCH₂ H O S C18.1 Me H 2-OMe,3-Me OCH₂ H O S C18.2 Me H 2-OMe,3-Me SCH₂ H O S C18.3 Et H 2-OMe,3-Me OCH₂ H O S C18.4 nPr H 2-OMe,3-Me OCH₂ H O S C18.5 iPr H 2-OMe,3-Me OCH₂ H O S C18.6 nBu H 2-OMe,3-Me OCH₂ H O S C18.7 FCH₂ H 2-OMe,3-Me OCH₂ H O S C18.8 F₂CH H 2-OMe,3-Me OCH₂ H O S C18.9 F₃C H 2-OMe,3-Me OCH₂ H O S C18.10 ClCH₂ H 2-OMe,3-Me OCH₂ H O S C18.11 Cl₂CH H 2-OMe,3-Me OCH₂ H O S C18.12 Me H 2-OMe,5-Me OCH₂ H O S C18.13 Me H 2-OMe,5-Me SCH₂ H O S C18.14 Et H 2-OMe,5-Me OCH₂ H O S C18.15 nPr H 2-OMe,5-Me OCH₂ H O S C18.16 iPr H 2-OMe,5-Me OCH₂ H O S C18.17 nBu H 2-OMe,5-Me OCH₂ H O S C18.18 FCH₂ H 2-OMe,5-Me OCH₂ H O S C18.19 F₂CH H 2-OMe,5-Me OCH₂ H O S C18.20 F₃C H 2-OMe,5-Me OCH₂ H O S C18.21 ClCH₂ H 2-OMe,5-Me OCH₂ H O S C18.22 Cl₂CH H 2-OMe,5-Me OCH₂ H O S C18.23 Me H 3-OMe,5-Me OCH₂ H O S C18.24 Me H 3-OMe,5-Me SCH₂ H O S C18.25 Et H 3-OMe,5-Me OCH₂ H O S C18.26 nPr H 3-OMe,5-Me OCH₂ H O S C18.27 iPr H 3-OMe,5-Me OCH₂ H O S C18.28 nBu H 3-OMe,5-Me OCH₂ H O S C18.29 FCH₂ H 3-OMe,5-Me OCH₂ H O S C18.30 F₂CH H 3-OMe,5-Me OCH₂ H O S C18.31 F₃C H 3-OMe,5-Me OCH₂ H O S C18.32 ClCH₂ H 3-OMe,5-Me OCH₂ H O S C18.33 Cl₂CH H 3-OMe,5-Me OCH₂ H O S C18.35 Me H 2-Me,3-OMe OCH₂ H O S C18.36 Me H 2-Me,3-OMe SCH₂ H O S C18.37 Et H 2-Me,3-OMe OCH₂ H O S C18.38 nPr H 2-Me,3-OMe OCH₂ H O S C18.39 iPr H 2-Me,3-OMe OCH₂ H O S C18.40 nBu H 2-Me,3-OMe OCH₂ H O S C18.41 FCH₂ H 2-Me,3-OMe OCH₂ H O S C18.42 F₂CH H 2-Me,3-OMe OCH₂ H O S C18.43 F₃C H 2-Me,3-OMe OCH₂ H O S C18.44 ClCH₂ H 2-Me,3-OMe OCH₂ H O S C18.45 Cl₂CH H 2-Me,3-OMe OCH₂ H O S C18.46 Me H 2-OMe,6-Me OCH₂ H O S C18.47 Me H 2-OMe,6-Me SCH₂ H O S C18.48 Et H 2-OMe,6-Me OCH₂ H O S C18.49 nPr H 2-OMe,6-Me OCH₂ H O S C18.50 iPr H 2-OMe,6-Me OCH₂ H O S C18.51 nBu H 2-OMe,6-Me OCH₂ H O S C18.52 FCH₂ H 2-OMe,6-Me OCH₂ H O S C18.53 F₂CH H 2-OMe,6-Me OCH₂ H O S C18.54 F₃C H 2-OMe,6-Me OCH₂ H O S C18.55 ClCH₂ H 2-OMe,6-Me OCH₂ H O S C18.56 Cl₂CH H 2-OMe,6-Me OCH₂ H O S C18.57 Me H 2-Me,5-OMe OCH₂ H O S C18.58 Me H 2-Me,5-OMe SCH₂ H O S C18.59 Et H 2-Me,5-OMe OCH₂ H O S C18.60 nPr H 2-Me,5-OMe OCH₂ H O S C18.61 iPr H 2-Me,5-OMe OCH₂ H O S C18.62 nBu H 2-Me,5-OMe OCH₂ H O S C18.63 FCH₂ H 2-Me,5-OMe OCH₂ H O S C18.64 F₂CH H 2-Me,5-OMe OCH₂ H O S C18.65 F₃C H 2-Me,5-OMe OCH₂ H O S C18.67 Cl₂CH H 2-Me,5-OMe OCH₂ H O S C18.68 Me H 2-iPr,3-Me OCH₂ H O S C18.69 Et H 2-iPr,3-Me OCH₂ H O S C18.70 nPr H 2-iPr,3-Me OCH₂ H O S C18.71 iPr H 2-iPr,3-Me OCH₂ H O S C18.72 nBu H 2-iPr,3-Me OCH₂ H O S C18.73 FCH₂ H 2-iPr,3-Me OCH₂ H O S C18.74 F₂CH H 2-iPr,3-Me OCH₂ H O S C18.75 F₃C H 2-iPr,3-Me OCH₂ H O S C18.76 ClCH₂ H 2-iPr,3-Me OCH₂ H O S C18.77 Cl₂CH H 2-iPr,3-Me OCH₂ H O S C18.78 Me H 2-iPr,5-Me OCH₂ H O S C18.79 Et H 2-iPr,5-Me OCH₂ H O S C18.80 nPr H 2-iPr,5-Me OCH₂ H O S C18.81 iPr H 2-iPr,5-Me OCH₂ H O S C18.82 nBu H 2-iPr,5-Me OCH₂ H O S C18.83 FCH₂ H 2-iPr,5-Me OCH₂ H O S C18.84 F₂CH H 2-iPr,5-Me OCH₂ H O S C18.85 F₃C H 2-iPr,5-Me OCH₂ H O S C18.86 ClCH₂ H 2-iPr,5-Me OCH₂ H O S C18.87 Cl₂CH H 2-iPr,5-Me OCH₂ H O S C18.88 Me H 3-Me,5-iPr OCH₂ H O S C18.89 Et H 3-Me,5-iPr OCH₂ H O S C18.90 nPr H 3-Me,5-iPr OCH₂ H O S C18.91 iPr H 3-Me,5-iPr OCH₂ H O S C18.92 nBu H 3-Me,5-iPr OCH₂ H O S C18.93 FCH₂ H 3-Me,5-iPr OCH₂ H O S C18.94 F₂CH H 3-Me,5-iPr OCH₂ H O S C18.96 ClCH₂ H 3-Me,5-iPr OCH₂ H O S C18.97 Cl₂CH H 3-Me,5-iPr OCH₂ H O S C18.98 Me H 2-Me,3-iPr OCH₂ H O S C18.99 Et H 2-Me,3-iPr OCH₂ H O S C18.100 nPr H 2-Me,3-iPr OCH₂ H O S C18.101 iPr H 2-Me,3-iPr OCH₂ H O S C18.102 nBu H 2-Me,3-iPr OCH₂ H O S C18.103 FCH₂ H 2-Me,3-iPr OCH₂ H O S C18.104 F₂CH H 2-Me,3-iPr OCH₂ H O S C18.105 F₃C H 2-Me,3-iPr OCH₂ H O S C18.106 ClCH₂ H 2-Me,3-iPr OCH₂ H O S C18.107 Cl₂CH H 2-Me,3-iPr OCH₂ H O S C18.108 Me H 2-Me,6-iPr OCH₂ H O S C18.109 Et H 2-Me,6-iPr OCH₂ H O S C18.110 nPr H 2-Me,6-iPr OCH₂ H O S C18.111 iPr H 2-Me,6-iPr OCH₂ H O S C18.112 nBu H 2-Me,6-iPr OCH₂ H O S C18.113 FCH₂ H 2-Me,6-iPr OCH₂ H O S C18.114 F₂CH H 2-Me,6-iPr OCH₂ H O S C18.115 F₃C H 2-Me,6-iPr OCH₂ H O S C18.116 ClCH₂ H 2-Me,6-iPr OCH₂ H O S C18.117 Cl₂CH H 2-Me,6-iPr OCH₂ H O S C18.118 Me H 2-Me,5-iPr OCH₂ H O S 153-156 C18.119 MeO H 2-Me,5-iPr OCH₂ H O S 115-117 C18.120 MeO H 2-Me,5-iPr OCH₂ H O O C18.121 Et H 2-Me,5-iPr OCH₂ H O S C18.122 nPr H 2-Me,5-iPr OCH₂ H O S C18.123 iPr H 2-Me,5-iPr OCH₂ H O S C18.124 nBu H 2-Me,5-iPr OCH₂ H O S C18.125 FCH₂ H 2-Me,5-iPr OCH₂ H O S C18.126 F₂CH H 2-Me,5-iPr OCH₂ H O S C18.127 F₃C H 2-Me,5-iPr OCH₂ H O S C18.128 ClCH₂ H 2-Me,5-iPr OCH₂ H O S C18.129 Cl₂CH H 2-Me,5-iPr OCH₂ H O S C18.130 Me H 2-Cl,6-CO₂Me OCH₂ H O S 141-143 C18.131 MeO H 2-Cl,6-CO₂Me OCH₂ H O S ────────────────────────────────────[Table 3] ──────────────────────────────────── Number R ¹ R ^Two (R ^Three ) n ACR ^Four (R ^Five ) (R ⁶ ) m XQ melting point (℃) ──────────────────────────────────── C1.1 Me H 2- Me OCH _Two HOS 179-182 C1.2 Me H 2-Me OCH _Two HOO 160 C1.3 Me H 2-Me SCH _Two HOS 116-117 C1.4 Me H 2-Me SCH _Two HOO C1.5 MeO H 2-Me OCH _Two HOS 147-149 C1.6 MeO H 2-Me OCH _Two HOO 159-162 C1.7 MeO H 2-Me SCH _Two HOS C1.8 MeO H 2-Me SCH _Two HOO C1.9 MeO H 2-Me OCH _Two HSS C1.10 MeO H 2-Me OCH _Two HSO C1.11 MeS H 2-Me OCH _Two HOS 145-147 C1.12 MeS H 2-Me OCH _Two HOO C1.13 MeS H 2-Me OCH _Two HSS 133-135 C1.14 MeS H 2-Me OCH _Two HSO C1.15 Et H 2-Me OCH _Two HOS C1.16 Et H 2-Me OCH _Two HOO C1.17 EtO H 2-Me OCH _Two HOS 124-127 C1.18 EtO H 2-Me OCH _Two HOO C1.19 Cl _Three CCH _Two OH 2-Me OCH _Two HOS 166-168 C1.20 Cl _Three CCH _Two OH 2-Me OCH _Two HOO C1.21 nPr H 2-Me OCH _Two HOS C1.22 iPr H 2-Me OCH _Two HOS C1.23 iPrO H 2-Me OCH _Two HOS 118-120 C1.24 nPrO H 2-Me OCH _Two HOS 121-124 C1.25 nPrO H 2-Me OCH _Two HOO C1.26 nBu H 2-Me OCH _Two HOS C1.27 tBu H 2-Me OCH _Two HOS 140-142 C1.28 nBuO H 2-Me OCH _Two HOS 127-128 C1.29 nBuO H 2-Me OCH _Two HOO C1.30 tBu H 2-Me OCH _Two HOO C1.31 tBuO H 2-Me OCH _Two HOS C1.32 tBuO H 2-Me OCH _Two HOO C1.33 iBu H 2-Me OCH _Two HOS C1.34 iBuO H 2-Me OCH _Two HOS C1.35 iBuO H 2-Me OCH _Two HOO C1.36 EtOCH _Two H 2-Me OCH _Two HOS 94-95 C1.37 EtOCH _Two H 2-Me OCH _Two HOO C1.38 nPrOCH _Two H 2-Me OCH _Two HOS C1.39 nPrOCH _Two H 2-Me OCH _Two HOO C1.40 iPrOCH _Two H 2-Me OCH _Two HOS C1.41 iPrOCH _Two H 2-Me OCH _Two HOO C1.42 MeOCH _Two CH _Two H 2-Me OCH _Two HOS 135-137 C1.43 MeOCH _Two CH _Two H 2-Me OCH _Two HOO C1.44 EtOCH _Two CH _Two H 2-Me OCH _Two HOS 135-137 C1.45 FCH _Two H 2-Me OCH _Two HOS C1.46 F _Two CH H 2-Me OCH _Two HOS C1.47 F _Three CH 2-Me OCH _Two HOS C1.48 ClCH _Two H 2-Me OCH _Two HOS C1.49 Cl _Two CH H 2-Me OCH _Two HOS C1.50 BrCH _Two H 2-Me OCH _Two HOS C1.51 FClCH H 2-Me OCH _Two HOS C1.52 Me H 3-Me OCH _Two HOS 157-159 C1.53 Me H 3-Me SCH _Two HOS C1.54 Me H 3-Me OCH _Two HOO C1.55 MeO H 3-Me OCH _Two HOS 125-126 C1.56 MeO H 3-Me OCH _Two HOO C1.57 Et H 3-Me OCH _Two HOS C1.58 nPr H 3-Me OCH _Two HOS C1.59 iPr H 3-Me OCH _Two HOS C1.60 nBu H 3-Me OCH _Two HOS C1.61 FCH _Two H 3-Me OCH _Two HOS C1.63 F _Three CH 3-Me OCH _Two HOS C1.64 ClCH _Two H 3-Me OCH _Two HOS C1.65 Cl _Two CH H 3-Me OCH _Two HOS C1.66 BrCH _Two H 3-Me OCH _Two HOS C1.67 FClCH H 3-Me OCH _Two HOS C2.1 Me H 2-Et OCH _Two HOS 165-168 C2.2 Me H 2-Et SCH _Two HOS C2.3 Me H 2-Et OCH _Two HOO C2.4 MeO H 2-Et OCH _Two HOS 140-141 C2.5 MeO H 2-Et SCH _Two HOS C2.6 MeO H 2-Et OCH _Two HOO C2.7 MeO H 2-Et SCH _Two HOO C2.8 Et H 2-Et OCH _Two HOS C2.9 nPr H 2-Et OCH _Two HOS C2.10 iPr H 2-Et OCH _Two HOS C2.11 nBu H 2-Et OCH _Two HOS C2.12 FCH _Two H 2-Et OCH _Two HOS C2.13 F _Two CH H 2-Et OCH _Two HOS C2.14 F _Three CH 2-Et OCH _Two HOS C2.15 ClCH _Two H 2-Et OCH _Two HOS C2.16 Cl _Two CH H 2-Et OCH _Two HOS C2.17 BrCH _Two H 2-Et OCH _Two HOS C2.18 FClCH H 2-Et OCH _Two HOS C2.19 Me H 3-Et OCH _Two HOS 135-137 C2.20 Me H 3-Et SCH _Two HOS C2.21 MeO H 3-Et OCH _Two HOS C2.22 MeO H 3-Et OCH _Two HOO C2.23 Et H 3-Et OCH _Two HOS C2.24 nPr H 3-Et OCH _Two HOS C2.25 iPr H 3-Et OCH _Two HOS C2.26 nBu H 3-Et OCH _Two HOS C2.27 FCH _Two H 3-Et OCH _Two HOS C2.28 F _Two CH H 3-Et OCH _Two HOS C2.29 F _Three CH 3-Et OCH _Two HOS C2.30 ClCH _Two H 3-Et OCH _Two HOS C2.31 Cl _Two CH H 3-Et OCH _Two HOS C2.32 BrCH _Two H 3-Et OCH _Two HOS C2.33 FClCH H 3-Et OCH _Two HOS C3.1 Me H 2-nPr OCH _Two HOS C3.2 Me H 2-nPr OCH _Two HOO C3.3 MeO H 2-nPr OCH _Two HOS C3.4 MeO H 2-nPr OCH _Two HOO C3.5 Et H 2-nPr OCH _Two HOS C3.6 nPr H 2-nPr OCH _Two HOS C3.7 iPr H 2-nPr OCH _Two HOS C3.8 nBu H 2-nPr OCH _Two HOS C3.9 FCH _Two H 2-nPr OCH _Two HOS C3.10 F _Two CH H 2-nPr OCH _Two HOS C3.11 F _Three CH 2-nPr OCH _Two HOS C3.12 ClCH _Two H 2-nPr OCH _Two HOS C3.13 Cl _Two CH H 2-nPr OCH _Two HOS C3.14 BrCH _Two H 2-nPr OCH _Two HOS C3.15 FClCH H 2-nPr OCH _Two HOS C3.16 Me H 3-nPr OCH _Two HOS C3.17 MeO H 3-nPr OCH _Two HOS C3.18 MeO H 3-nPr OCH _Two HOO C3.19 Et H 3-nPr OCH _Two HOS C3.21 iPr H 3-nPr OCH _Two HOS C3.22 nBu H 3-nPr OCH _Two HOS C3.23 FCH _Two H 3-nPr OCH _Two HOS C3.24 F _Two CH H 3-nPr OCH _Two HOS C3.25 F _Three CH 3-nPr OCH _Two HOS C3.26 ClCH _Two H 3-nPr OCH _Two HOS C3.27 Cl _Two CH H 3-nPr OCH _Two HOS C3.28 BrCH _Two H 3-nPr OCH _Two HOS C3.29 FClCH H 3-nPr OCH _Two HOS C3.30 Me H 2-iPr OCH _Two HOS 165-170 C3.31 Me H 2-iPr OCH _Two HOO C3.32 MeO H 2-iPr OCH _Two HOS 113-114 C3.33 MeO H 2-iPr OCH _Two HOO C3.34 Et H 2-iPr OCH _Two HOS C3.35 nPr H 2-iPr OCH _Two HOS C3.36 iPr H 2-iPr OCH _Two HOS C3.37 nBu H 2-iPr OCH _Two HOS C3.38 FCH _Two H 2-iPr OCH _Two HOS C3.39 F _Two CH H 2-iPr OCH _Two HOS C3.40 F _Three CH 2-iPr OCH _Two HOS C3.41 ClCH _Two H 2-iPr OCH _Two HOS C3.42 Cl _Two CH H 2-iPr OCH _Two HOS C3.43 BrCH _Two H 2-iPr OCH _Two HOS C3.44 FClCH H 2-iPr OCH _Two HOS C3.45 Me H 3-iPr OCH _Two HOS C3.46 MeO H 3-iPr OCH _Two HOS C3.47 Et H 3-iPr OCH _Two HOS C3.48 nPr H 3-iPr OCH _Two HOS C3.49 iPr H 3-iPr OCH _Two HOS C3.50 nBu H 3-iPr OCH _Two HOS C3.51 FCH _Two H 3-iPr OCH _Two HOS C3.52 F _Two CH H 3-iPr OCH _Two HOS C3.53 F _Three CH 3-iPr OCH _Two HOS C3.54 ClCH _Two H 3-iPr OCH _Two HOS C3.55 Cl _Two CH H 3-iPr OCH _Two HOS C3.56 BrCH _Two H 3-iPr OCH _Two HOS C3.57 FClCH H 3-iPr OCH _Two HOS C4.1 Me H 2-nBu OCH _Two HOS C4.2 MeO H 2-nBu OCH _Two HOS C4.3 MeO H 2-nBu OCH _Two HOO C4.4 Et H 2-nBu OCH _Two HOS C4.5 nPr H 2-nBu OCH _Two HOS C4.6 iPr H 2-nBu OCH _Two HOS C4.7 nBu H 2-nBu OCH _Two HOS C4.8 FCH _Two H 2-nBu OCH _Two HOS C4.9 F _Two CH H 2-nBu OCH _Two HOS C4.10 F _Three CH 2-nBu OCH _Two HOS C4.11 ClCH _Two H 2-nBu OCH _Two HOS C4.12 Cl _Two CH H 2-nBu OCH _Two HOS C4.13 BrCH _Two H 2-nBu OCH _Two HOS C4.14 FClCH H 2-nBu OCH _Two HOS C4.15 Me H 2-iBu OCH _Two HOS C4.16 Et H 2-iBu OCH _Two HOS C4.17 nPr H 2-iBu OCH _Two HOS C4.18 iPr H 2-iBu OCH _Two HOS C4.19 nBu H 2-iBu OCH _Two HOS C4.20 FCH _Two H 2-iBu OCH _Two HOS C4.21 F _Two CH H 2-iBu OCH _Two HOS C4.22F _Three CH 2-iBu OCH _Two HOS C4.23 ClCH _Two H 2-iBu OCH _Two HOS C4.24 Cl _Two CH H 2-iBu OCH _Two HOS C4.25 BrCH _Two H 2-iBu OCH _Two HOS C4.26 FClCH H 2-iBu OCH _Two HOS C4.27 Me H 2-tBu OCH _Two HOS 158-165 C4.28 Me H 2-tBu OCH _Two HOO C4.29 MeO H 2-tBu OCH _Two HOS 162-164 C4.30 MeO H 2-tBu OCH _Two HOO C4.31 Et H 2-tBu OCH _Two HOS C4.32 nPr H 2-tBu OCH _Two HOS C4.33 iPr H 2-tBu OCH _Two HOS C4.34 nBu H 2-tBu OCH _Two HOS C4.35 FCH _Two H 2-tBu OCH _Two HOS C4.36 F _Two CH H 2-tBu OCH _Two HOS C4.37 F _Three CH 2-tBu OCH _Two HOS C4.38 ClCH _Two H 2-tBu OCH _Two HOS C4.39 Cl _Two CH H 2-tBu OCH _Two HOS C4.40 BrCH _Two H 2-tBu OCH _Two HOS C4.41 FClCH H 2-tBu OCH _Two HOS C4.42 MeO H 3-nBu OCH _Two HOS C4.43 MeO H 3-nBu OCH _Two HOO C4.44 Me H 3-nBu OCH _Two HOS C4.45 Et H 3-nBu OCH _Two HOS C4.46 nPr H 3-nBu OCH _Two HOS C4.47 iPr H 3-nBu OCH _Two HOS C4.48 nBu H 3-nBu OCH _Two HOS C4.49 FCH _Two H 3-nBu OCH _Two HOS C4.50 F _Two CH H 3-nBu OCH _Two HOS C4.51 F _Three CH 3-nBu OCH _Two HOS C4.52 ClCH _Two H 3-nBu OCH _Two HOS C4.53 Cl _Two CH H 3-nBu OCH _Two HOS C4.54 BrCH _Two H 3-nBu OCH _Two HOS C4.55 FClCH H 3-nBu OCH _Two HOS C4.56 Me H 3-iBu OCH _Two HOS C4.57 Et H 3-iBu OCH _Two HOS C4.58 nPr H 3-iBu OCH _Two HOS C4.59 iPr H 3-iBu OCH _Two HOS C4.60 nBu H 3-iBu OCH _Two HOS C4.61 FCH _Two H 3-iBu OCH _Two HOS C4.62 F _Two CH H 3-iBu OCH _Two HOS C4.63 F _Three CH 3-iBu OCH _Two HOS C4.64 ClCH _Two H 3-iBu OCH _Two HOS C4.65 Cl _Two CH H 3-iBu OCH _Two HOS C4.66 BrCH _Two H 3-iBu OCH _Two HOS C4.67 FClCH H 3-iBu OCH _Two HOS C4.68 Me H 3-tBu OCH _Two HOS C4.69 MeO H 3-tBu OCH _Two HOS C4.70 Et H 3-tBu OCH _Two HOS C4.71 nPr H 3-tBu OCH _Two HOS C4.72 iPr H 3-tBu OCH _Two HOS C4.73 nBu H 3-tBu OCH _Two HOS C4.74 FCH _Two H 3-tBu OCH _Two HOS C4.75 F _Two CH H 3-tBu OCH _Two HOS C4.76 F _Three CH 3-tBu OCH _Two HOS C4.77 ClCH _Two H 3-tBu OCH _Two HOS C4.78 Cl _Two CH H 3-tBu OCH _Two HOS C4.79 BrCH _Two H 3-tBu OCH _Two HOS C4.80 FClCH H 3-tBu OCH _Two HOS C5.1 Me H 2-CH _Two CH = CH _Two OCH _Two HOS C5.2 MeO H 2-CH _Two CH = CH _Two OCH _Two HOS C5.3 MeO H 2-CH _Two CH = CH _Two OCH _Two HOO C5.4 Et H 2-CH _Two CH = CH _Two OCH _Two HOS C5.5 nPr H 2-CH _Two CH = CH _Two OCH _Two HOS C5.6 iPr H 2-CH _Two CH = CH _Two OCH _Two HOS C5.7 nBu H 2-CH _Two CH = CH _Two OCH _Two HOS C5.8 FCH _Two H 2-CH _Two CH = CH _Two OCH _Two HOS C5.9 F _Two CH H 2-CH _Two CH = CH _Two OCH _Two HOS C5.10 F _Three CH 2-CH _Two CH = CH _Two OCH _Two HOS C5.11 ClCH _Two H 2-CH _Two CH = CH _Two OCH _Two HOS C5.12 Cl _Two CH H 2-CH _Two CH = CH _Two OCH _Two HOS C5.13 BrCH _Two H 2-CH _Two CH = CH _Two OCH _Two HOS C5.14 FClCH H 2-CH _Two CH = CH _Two OCH _Two HOS C5.15 Me H 3-CH _Two CH = CH _Two OCH _Two HOS C5.16 MeO H 3-CH _Two CH = CH _Two OCH _Two HOS C5.17 MeO H 3-CH _Two CH = CH _Two OCH _Two HOO C5.18 Et H 3-CH _Two CH = CH _Two OCH _Two HOS C5.19 nPr H 3-CH _Two CH = CH _Two OCH _Two HOS C5.20 iPr H 3-CH _Two CH = CH _Two OCH _Two HOS C5.21 nBu H 3-CH _Two CH = CH _Two OCH _Two HOS C5.22 FCH _Two H 3-CH _Two CH = CH _Two OCH _Two HOS C5.23 F _Two CH H 3-CH _Two CH = CH _Two OCH _Two HOS C5.24 F _Three CH 3-CH _Two CH = CH _Two OCH _Two HOS C5.25 ClCH _Two H 3-CH _Two CH = CH _Two OCH _Two HOS C5.26 Cl _Two CH H 3-CH _Two CH = CH _Two OCH _Two HOS C5.27 BrCH _Two H 3-CH _Two CH = CH _Two OCH _Two HOS C5.28 FClCH H 3-CH _Two CH = CH _Two OCH _Two HOS C5.29 Me H 2-CH _Two C≡CH OCH _Two HOS C5.30 MeO H 2-CH _Two C≡CH OCH _Two HOS C5.31 MeO H 2-CH _Two C≡CH OCH _Two HOO C5.32 Et H 2-CH _Two C≡CH OCH _Two HOS C5.33 nPr H 2-CH _Two C≡CH OCH _Two HOS C5.34 iPr H 2-CH _Two C≡CH OCH _Two HOS C5.35 nBu H 2-CH _Two C≡CH OCH _Two HOS C5.36 FCH _Two H 2-CH _Two C≡CH OCH _Two HOS C5.37 F _Two CH H 2-CH _Two C≡CH OCH _Two HOS C5.38 F _Three CH 2-CH _Two C≡CH OCH _Two HOS C5.39 ClCH _Two H 2-CH _Two C≡CH OCH _Two HOS C5.40 Cl _Two CH H 2-CH _Two C≡CH OCH _Two HOS C5.41 BrCH _Two H 2-CH _Two C≡CH OCH _Two HOS C5.42 FClCH H 2-CH _Two C≡CH OCH _Two HOS C5.43 Me H 3-CH _Two C≡CH OCH _Two HOS C5.44 MeO H 3-CH _Two C≡CH OCH _Two HOS C5.45 Et H 3-CH _Two C≡CH OCH _Two HOS C5.46 nPr H 3-CH _Two C≡CH OCH _Two HOS C5.47 iPr H 3-CH _Two C≡CH OCH _Two HOS C5.48 nBu H 3-CH _Two C≡CH OCH _Two HOS C5.49 FCH _Two H 3-CH _Two C≡CH OCH _Two HOS C5.50 F _Two CH H 3-CH _Two C≡CH OCH _Two HOS C5.51 F _Three CH 3-CH _Two C≡CH OCH _Two HOS C5.52 ClCH _Two H 3-CH _Two C≡CH OCH _Two HOS C5.53 Cl _Two CH H 3-CH _Two C≡CH OCH _Two HOS C5.54 BrCH _Two H 3-CH _Two C≡CH OCH _Two HOS C5.55 FClCH H 3-CH _Two C≡CH OCH _Two HOS C6.1 Me H 2-CH _Two OMe OCH _Two HOS 157-160 C6.2 MeO H 2-CH _Two OMe OCH _Two HOS C6.3 Me H 2-CH _Two OMe OCH _Two HOO C6.4 MeO H 2-CH _Two OMe OCH _Two HOO C6.5 Et H 2-CH _Two OMe OCH _Two HOS C6.6 nPr H 2-CH _Two OMe OCH _Two HOS C6.7 iPr H 2-CH _Two OMe OCH _Two HOS C6.8 nBu H 2-CH _Two OMe OCH _Two HOS C6.9 FCH _Two H 2-CH _Two OMe OCH _Two HOS C6.10 F _Two CH H 2-CH _Two OMe OCH _Two HOS C6.11 F _Three CH 2-CH _Two OMe OCH _Two HOS C6.12 ClCH _Two H 2-CH _Two OMe OCH _Two HOS C6.13 Cl _Two CH H 2-CH _Two OMe OCH _Two HOS C6.14 BrCH _Two H 2-CH _Two OMe OCH _Two HOS C6.15 FClCH H 2-CH _Two OMe OCH _Two HOS C6.16 Me H 3-CH _Two OMe OCH _Two HOS C6.17 MeO H 3-CH _Two OMe OCH _Two HOS C6.18 Et H 3-CH _Two OMe OCH _Two HOS C6.19 nPr H 3-CH _Two OMe OCH _Two HOS C6.20 iPr H 3-CH _Two OMe OCH _Two HOS C6.21 nBu H 3-CH _Two OMe OCH _Two HOS C6.22 FCH _Two H 3-CH _Two OMe OCH _Two HOS C6.23 F _Two CH H 3-CH _Two OMe OCH _Two HOS C6.24 F _Three CH 3-CH _Two OMe OCH _Two HOS C6.25 ClCH _Two H 3-CH _Two OMe OCH _Two HOS C6.26 Cl _Two CH H 3-CH _Two OMe OCH _Two HOS C6.27 BrCH _Two H 3-CH _Two OMe OCH _Two HOS C6.28 FClCH H 3-CH _Two OMe OCH _Two HOS C6.29 Me H 2-CH _Two OEt OCH _Two HOS 154-156 C6.30 Me H 2-CH _Two OEt OCH _Two HOO C6.31 MeO H 2-CH _Two OEt OCH _Two HOS C6.32 Et H 2-CH _Two OEt OCH _Two HOS C6.33 nPr H 2-CH _Two OEt OCH _Two HOS C6.34 iPr H 2-CH _Two OEt OCH _Two HOS C6.35 nBu H 2-CH _Two OEt OCH _Two HOS C6.36 FCH _Two H 2-CH _Two OEt OCH _Two HOS C6.37 F _Two CH H 2-CH _Two OEt OCH _Two HOS C6.38 F _Three CH 2-CH _Two OEt OCH _Two HOS C6.39 ClCH _Two H 2-CH _Two OEt OCH _Two HOS C6.40 Cl _Two CH H 2-CH _Two OEt OCH _Two HOS C6.41 BrCH _Two H 2-CH _Two OEt OCH _Two HOS C6.42 FClCH H 2-CH _Two OEt OCH _Two HOS C6.43 Me H 3-CH _Two OEt OCH _Two HOS C6.44 Et H 3-CH _Two OEt OCH _Two HOS C6.45 nPr H 3-CH _Two OEt OCH _Two HOS C6.46 iPr H 3-CH _Two OEt OCH _Two HOS C6.47 nBu H 3-CH _Two OEt OCH _Two HOS C6.48 FCH _Two H 3-CH _Two OEt OCH _Two HOS C6.49 F _Two CH H 3-CH _Two OEt OCH _Two HOS C6.50 F _Three CH 3-CH _Two OEt OCH _Two HOS C6.51 ClCH _Two H 3-CH _Two OEt OCH _Two HOS C6.52 Cl _Two CH H 3-CH _Two OEt OCH _Two HOS C6.53 BrCH _Two H 3-CH _Two OEt OCH _Two HOS C6.54 FClCH H 3-CH _Two OEt OCH _Two HOS C6.55 Me H 2-CH _Two CH _Two OMe OCH _Two HOS C6.56 Et H 2-CH _Two CH _Two OMe OCH _Two HOS C6.57 nPr H 2-CH _Two CH _Two OMe OCH _Two HOS C6.58 iPr H 2-CH _Two CH _Two OMe OCH _Two HOS C6.59 nBu H 2-CH _Two CH _Two OMe OCH _Two HOS C6.60 FCH _Two H 2-CH _Two CH _Two OMe OCH _Two HOS C6.61 F _Two CH H 2-CH _Two CH _Two OMe OCH _Two HOS C6.62 F _Three CH 2-CH _Two CH _Two OMe OCH _Two HOS C6.63 ClCH _Two H 2-CH _Two CH _Two OMe OCH _Two HOS C6.64 Cl _Two CH H 2-CH _Two CH _Two OMe OCH _Two HOS C6.65 BrCH _Two H 2-CH _Two CH _Two OMe OCH _Two HOS C6.66 FClCH H 2-CH _Two CH _Two OMe OCH _Two HOS C6.67 Me H 3-CH _Two CH _Two OMe OCH _Two HOS C6.68 Me H 3-CH _Two CH _Two OMe OCH _Two HOO C6.69 Et H 3-CH _Two CH _Two OMe OCH _Two HOS C6.70 nPr H 3-CH _Two CH _Two OMe OCH _Two HOS C6.71 iPr H 3-CH _Two CH _Two OMe OCH _Two HOS C6.72 nBu H 3-CH _Two CH _Two OMe OCH _Two HOS C6.73 FCH _Two H 3-CH _Two CH _Two OMe OCH _Two HOS C6.74 F _Two CH H 3-CH _Two CH _Two OMe OCH _Two HOS C6.75 F _Three CH 3-CH _Two CH _Two OMe OCH _Two HOS C6.76 ClCH _Two H 3-CH _Two CH _Two OMe OCH _Two HOS C6.77 Cl _Two CH H 3-CH _Two CH _Two OMe OCH _Two HOS C6.78 BrCH _Two H 3-CH _Two CH _Two OMe OCH _Two HOS C6.79 FClCH H 3-CH _Two CH _Two OMe OCH _Two HOS C6.80 Me H 2-CH _Two CH _Two OEt OCH _Two HOS C6.81 Et H 2-CH _Two CH _Two OEt OCH _Two HOS C6.82 nPr H 2-CH _Two CH _Two OEt OCH _Two HOS C6.83 iPr H 2-CH _Two CH _Two OEt OCH _Two HOS C6.84 nBu H 2-CH _Two CH _Two OEt OCH _Two HOS C6.85 FCH _Two H 2-CH _Two CH _Two OEt OCH _Two HOS C6.86 F _Two CH H 2-CH _Two CH _Two OEt OCH _Two HOS C6.87 F _Three CH 2-CH _Two CH _Two OEt OCH _Two HOS C6.88 ClCH _Two H 2-CH _Two CH _Two OEt OCH _Two HOS C6.89 Cl _Two CH H 2-CH _Two CH _Two OEt OCH _Two HOS C6.90 BrCH _Two H 2-CH _Two CH _Two OEt OCH _Two HOS C6.91 FClCH H 2-CH _Two CH _Two OEt OCH _Two HOS C6.92 Me H 3-CH _Two CH _Two OEt OCH _Two HOS C6.93 Et H 3-CH _Two CH _Two OEt OCH _Two HOS C6.94 nPr H 3-CH _Two CH _Two OEt OCH _Two HOS C6.95 iPr H 3-CH _Two CH _Two OEt OCH _Two HOS C6.96 nBu H 3-CH _Two CH _Two OEt OCH _Two HOS C6.97 FCH _Two H 3-CH _Two CH _Two OEt OCH _Two HOS C6.98 F _Two CH H 3-CH _Two CH _Two OEt OCH _Two HOS C6.99 F _Three CH 3-CH _Two CH _Two OEt OCH _Two HOS C6.100 ClCH _Two H 3-CH _Two CH _Two OEt OCH _Two HOS C6.101 Cl _Two CH H 3-CH _Two CH _Two OEt OCH _Two HOS C6.102 BrCH _Two H 3-CH _Two CH _Two OEt OCH _Two HOS C6.103 FClCH H 3-CH _Two CH _Two OEt OCH _Two HOS C7.1 Me H 2-CH _Two Cl OCH _Two HOS C7.2 MeO H 2-CH _Two Cl OCH _Two HOS C7.3 Me H 2-CH _Two Cl SCH _Two HOS C7.4 Et H 2-CH _Two Cl OCH _Two HOS C7.5 nPr H 2-CH _Two Cl OCH _Two HOS C7.6 iPr H 2-CH _Two Cl OCH _Two HOS C7.7 nBu H 2-CH _Two Cl OCH _Two HOS C7.8 FCH _Two H 2-CH _Two Cl OCH _Two HOS C7.9 F _Two CH H 2-CH _Two Cl OCH _Two HOS C7.10 F _Three CH 2-CH _Two Cl OCH _Two HOS C7.11 ClCH _Two H 2-CH _Two Cl OCH _Two HOS C7.12 Cl _Two CH H 2-CH _Two Cl OCH _Two HOS C7.13 BrCH _Two H 2-CH _Two Cl OCH _Two HOS C7.14 FClCH H 2-CH _Two Cl OCH _Two HOS C7.15 Me H 2-CH _Two Br OCH _Two HOS C7.16 Et H 2-CH _Two Br OCH _Two HOS C7.17 nPr H 2-CH _Two Br OCH _Two HOS C7.18 iPr H 2-CH _Two Br OCH _Two HOS C7.19 nBu H 2-CH _Two Br OCH _Two HOS C7.20 FCH _Two H 2-CH _Two Br OCH _Two HOS C7.21 F _Two CH H 2-CH _Two Br OCH _Two HOS C7.22 F _Three CH 2-CH _Two Br OCH _Two HOS C7.23 ClCH _Two H 2-CH _Two Br OCH _Two HOS C7.24 Cl _Two CH H 2-CH _Two Br OCH _Two HOS C7.25 BrCH _Two H 2-CH _Two Br OCH _Two HOS C7.26 FClCH H 2-CH _Two Br OCH _Two HOS C7.27 Me H 3-CH _Two Cl OCH _Two HOS C7.28 MeO H 3-CH _Two Cl OCH _Two HOS C7.29 Me H 3-CH _Two Cl SCH _Two HOS C7.30 Et H 3-CH _Two Cl OCH _Two HOS C7.31 nPr H 3-CH _Two Cl OCH _Two HOS C7.32 iPr H 3-CH _Two Cl OCH _Two HOS C7.33 nBu H 3-CH _Two Cl OCH _Two HOS C7.34 FCH _Two H 3-CH _Two Cl OCH _Two HOS C7.35 F _Two CH H 3-CH _Two Cl OCH _Two HOS C7.36 F _Three CH 3-CH _Two Cl OCH _Two HOS C7.37 ClCH _Two H 3-CH _Two Cl OCH _Two HOS C7.38 Cl _Two CH H 3-CH _Two Cl OCH _Two HOS C7.39 BrCH _Two H 3-CH _Two Cl OCH _Two HOS C7.40 FClCH H 3-CH _Two Cl OCH _Two HOS C7.41 Me H 3-CH _Two Br OCH _Two HOS C7.42 Et H 3-CH _Two Br OCH _Two HOS C7.43 nPr H 3-CH _Two Br OCH _Two HOS C7.44 iPr H 3-CH _Two Br OCH _Two HOS C7.45 nBu H 3-CH _Two Br OCH _Two HOS C7.46 FCH _Two H 3-CH _Two Br OCH _Two HOS C7.47 F _Two CH H 3-CH _Two Br OCH _Two HOS C7.48 F _Three CH 3-CH _Two Br OCH _Two HOS C7.49 ClCH _Two H 3-CH _Two Br OCH _Two HOS C7.50 Cl _Two CH H 3-CH _Two Br OCH _Two HOS C7.51 BrCH _Two H 3-CH _Two Br OCH _Two HOS C7.52 FClCH H 3-CH _Two Br OCH _Two HOS C7.53 MeO H 3-CH _Two F OCH _Two HOS C7.54 MeO H 3-CH _Two F OCH _Two HOS C7.55 Me H 2-CHF _Two OCH _Two HOS 195-198 C7.56 MeO H 2-CHF _Two OCH _Two HOS C7.57 Me H 2-CHF _Two OCH _Two HOO C7.58 MeO H 2-CHF _Two OCH _Two HOO C8.1 Me H 2-OMe OCH _Two HOS 163-165 C8.2 Me H 2-OMe OCH _Two HOO 118-119 C8.3 MeO H 2-OMe OCH _Two HOS 112-114 C8.4 Me H 2-OMe SCH _Two HOS C8.5 MeO H 2-OMe SCH _Two HOS C8.6 MeO H 2-OMe OCH _Two HOO 91-93 C8.7 MeO H 2-OMe SCH _Two HOO C8.8 Et H 2-OMe OCH _Two HOS C8.9 nPr H 2-OMe OCH _Two HOS C8.10 iPr H 2-OMe OCH _Two HOS C8.11 nBu H 2-OMe OCH _Two HOS C8.12 FCH _Two H 2-OMe OCH _Two HOS C8.13 F _Two CH H 2-OMe OCH _Two HOS C8.14 F _Three CH 2-OMe OCH _Two HOS C8.15 ClCH _Two H 2-OMe OCH _Two HOS C8.16 Cl _Two CH H 2-OMe OCH _Two HOS C8.17 BrCH _Two H 2-OMe OCH _Two HOS C8.18 FClCH H 2-OMe OCH _Two HOS C8.19 Me H 3-OMe OCH _Two HOS 108-113 C8.20 MeO H 3-OMe OCH _Two HOS 93-96 C8.21 Me H 3-OMe SCH _Two HOS C8.22 Me H 3-OMe OCH _Two HOO 98-100 C8.23 MeO H 3-OMe OCH _Two HOO 97-99 C8.24 Et H 3-OMe OCH _Two HOS C8.25 nPr H 3-OMe OCH _Two HOS C8.26 iPr H 3-OMe OCH _Two HOS C8.27 nBu H 3-OMe OCH _Two HOS C8.28 FCH _Two H 3-OMe OCH _Two HOS C8.29 F _Two CH H 3-OMe OCH _Two HOS C8.30 F _Three CH 3-OMe OCH _Two HOS C8.31 ClCH _Two H 3-OMe OCH _Two HOS C8.32 Cl _Two CH H 3-OMe OCH _Two HOS C8.33 BrCH _Two H 3-OMe OCH _Two HOS C8.34 FClCH H 3-OMe OCH _Two HOS C8.35 Me H 2-OEt OCH _Two HOO C8.36 Me H 2-OEt SCH _Two HOO C8.37 MeO H 2-OEt OCH _Two HOS C8.38 MeO H 2-OEt OCH _Two HOO C8.39 Me H 2-OEt OCH _Two HOS 131-133 C8.40 MeO H 2-OEt SCH _Two HOS C8.41 Me H 2-OEt SCH _Two HOS C8.42 Et H 2-OEt OCH _Two HOS C8.43 nPr H 2-OEt OCH _Two HOS C8.44 iPr H 2-OEt OCH _Two HOS C8.45 nBu H 2-OEt OCH _Two HOS C8.46 FCH _Two H 2-OEt OCH _Two HOS C8.47 F _Two CH H 2-OEt OCH _Two HOS C8.48 F _Three CH 2-OEt OCH _Two HOS C8.49 ClCH _Two H 2-OEt OCH _Two HOS C8.50 Cl _Two CH H 2-OEt OCH _Two HOS C8.51 BrCH _Two H 2-OEt OCH _Two HOS C8.52 FClCH H 2-OEt OCH _Two HOS C8.53 Me H 3-OEt OCH _Two HOS C8.54 MeO H 3-OEt OCH _Two HOO C8.55 MeO H 3-OEt OCH _Two HOS C8.56 Me H 3-OEt SCH _Two HOS C8.57 Et H 3-OEt OCH _Two HOS C8.58 nPr H 3-OEt OCH _Two HOS C8.59 iPr H 3-OEt OCH _Two HOS C8.60 nBu H 3-OEt OCH _Two HOS C8.61 FCH _Two H 3-OEt OCH _Two HOS C8.62 F _Two CH H 3-OEt OCH _Two HOS C8.63 F _Three CH 3-OEt OCH _Two HOS C8.64 ClCH _Two H 3-OEt OCH _Two HOS C8.65 Cl _Two CH H 3-OEt OCH _Two HOS C8.66 BrCH _Two H 3-OEt OCH _Two HOS C8.67 FClCH H 3-OEt OCH _Two HOS C8.68 Me H 2-OiPr OCH _Two HOS C8.69 MeO H 2-OiPr OCH _Two HOS C8.70 Me H 2-OiPr OCH _Two HOO C8.71 MeO H 2-OiPr OCH _Two HOO C8.72 Me H 2-OCHF _Two OCH _Two HOS 120-121 C8.73 MeO H 2-OCHF _Two OCH _Two HOS C8.74 Me H 2-OCHF _Two OCH _Two HOO C8.75 MeO H 2-OCHF _Two OCH _Two HOO C8.76 Me H 2-OCH _Two CF _Three OCH _Two HOS 136-138 C8.77 Me H 2-OCH _Two CF _Three OCH _Two HOO C8.78 MeO H 2-OCH _Two CF _Three OCH _Two HOS C9.1 Me H 2-F OCH _Two HOS 167-169 C9.2 Me H 2-F SCH _Two HOS C9.3 Me H 2-F OCH _Two HOO 135-136 C9.4 MeO H 2-F OCH _Two HOS 124-127 C9.5 MeO H 2-F SCH _Two HOS C9.6 MeO H 2-F OCH _Two HOO 110-115 C9.7 MeO H 2-F SCH _Two HOO C9.8 Et H 2-F OCH _Two HOS C9.9 nPr H 2-F OCH _Two HOS C9.10 iPr H 2-F OCH _Two HOS C9.11 nBu H 2-F OCH _Two HOS C9.12 FCH _Two H 2-F OCH _Two HOS C9.13 F _Two CH H 2-F OCH _Two HOS C9.14 F _Three CH 2-F OCH _Two HOS C9.15 ClCH _Two H 2-F OCH _Two HOS C9.16 Cl _Two CH H 2-F OCH _Two HOS C9.17 BrCH _Two H 2-F OCH _Two HOS C9.18 FClCH H 2-F OCH _Two HOS C9.20 Me H 3-F OCH _Two HOS 150-151 C9.21 Me H 3-F SCH _Two HOS C9.22 Me H 3-F OCH _Two HOO 140-142 C9.23 MeO H 3-F OCH _Two HOS 112-115 C9.24 MeO H 3-F OCH _Two HOO 135-138 C9.25 Et H 3-F OCH _Two HOS C9.26 nPr H 3-F OCH _Two HOS C9.27 iPr H 3-F OCH _Two HOS C9.28 nBu H 3-F OCH _Two HOS C9.29 FCH _Two H 3-F OCH _Two HOS C9.30 F _Two CH H 3-F OCH _Two HOS C9.31 F _Three CH 3-F OCH _Two HOS C9.32 ClCH _Two H 3-F OCH _Two HOS C9.33 Cl _Two CH H 3-F OCH _Two HOS C9.34 BrCH _Two H 3-F OCH _Two HOS C9.35 FClCH H 3-F OCH _Two HOS C9.36 Me H 2-Cl OCH _Two HOS 159-161 C9.37 Me H 2-Cl SCH _Two HOS C9.38 Me H 2-Cl OCH _Two HOO 130-131 C9.39 MeO H 2-Cl OCH _Two HOS 173.5-174.5 C9.40 MeO H 2-Cl OCH _Two HOO 120-122 C9.41 Et H 2-Cl OCH _Two HOS C9.42 nPr H 2-Cl OCH _Two HOS C9.43 iPr H 2-Cl OCH _Two HOS C9.44 nBu H 2-Cl OCH _Two HOS C9.45 FCH _Two H 2-Cl OCH _Two HOS C9.46 F _Two CH H 2-Cl OCH _Two HOS C9.47 F _Three CH 2-Cl OCH _Two HOS C9.48 ClCH _Two H 2-Cl OCH _Two HOS C9.49 Cl _Two CH H 2-Cl OCH _Two HOS C9.50 BrCH _Two H 2-Cl OCH _Two HOS C9.51 FClCH H 2-Cl OCH _Two HOS C9.52 Me H 3-Cl OCH _Two HOS 168-169 C9.53 Me H 3-Cl SCH _Two HOS C9.54 Me H 3-Cl OCH _Two HOO 161-165 C9.55 MeO H 3-Cl OCH _Two HOS 133-135 C9.56 MeO H 3-Cl OCH _Two HOO 164-166 C9.57 Et H 3-Cl OCH _Two HOS C9.58 nPr H 3-Cl OCH _Two HOS C9.59 iPr H 3-Cl OCH _Two HOS C9.60 nBu H 3-Cl OCH _Two HOS C9.61 FCH _Two H 3-Cl OCH _Two HOS C9.62 F _Two CH H 3-Cl OCH _Two HOS C9.63 F _Three CH 3-Cl OCH _Two HOS C9.64 ClCH _Two H 3-Cl OCH _Two HOS C9.65 Cl _Two CH H 3-Cl OCH _Two HOS C9.66 BrCH _Two H 3-Cl OCH _Two HOS C9.67 FClCH H 3-Cl OCH _Two HOS C9.68 Me H 2-Br OCH _Two HOS C9.69 Et H 2-Br OCH _Two HOS C9.70 nPr H 2-Br OCH _Two HOS C9.71 iPr H 2-Br OCH _Two HOS C9.72 nBu H 2-Br OCH _Two HOS C9.73 FCH _Two H 2-Br OCH _Two HOS C9.74 F _Two CH H 2-Br OCH _Two HOS C9.75 F _Three CH 2-Br OCH _Two HOS C9.76 ClCH _Two H 2-Br OCH _Two HOS C9.77 Cl _Two CH H 2-Br OCH _Two HOS C9.78 BrCH _Two H 2-Br OCH _Two HOS C9.79 FClCH H 2-Br OCH _Two HOS C9.80 Me H 3-Br OCH _Two HOS C9.81 Et H 3-Br OCH _Two HOS C9.82 nPr H 3-Br OCH _Two HOS C9.84 nBu H 3-Br OCH _Two HOS C9.85 FCH _Two H 3-Br OCH _Two HOS C9.86 F _Two CH H 3-Br OCH _Two HOS C9.87 F _Three CH 3-Br OCH _Two HOS C9.88 ClCH _Two H 3-Br OCH _Two HOS C9.89 Cl _Two CH H 3-Br OCH _Two HOS C9.90 BrCH _Two H 3-Br OCH _Two HOS C9.91 FClCH H 3-Br OCH _Two HOS C9.92 Me H 2-I OCH _Two HOS C9.93 Et H 2-I OCH _Two HOS C9.94 nPr H 2-I OCH _Two HOS C9.95 iPr H 2-I OCH _Two HOS C9.96 nBu H 2-I OCH _Two HOS C9.97 FCH _Two H 2-I OCH _Two HOS C9.98 F _Two CH H 2-I OCH _Two HOS C9.99 F _Three CH 2-I OCH _Two HOS C9.100 ClCH _Two H 2-I OCH _Two HOS C9.101 Cl _Two CH H 2-I OCH _Two HOS C9.102 BrCH _Two H 2-I OCH _Two HOS C9.103 FClCH H 2-I OCH _Two HOS C9.104 Me H 3-I OCH _Two HOS C9.105 Et H 3-I OCH _Two HOS C9.106 nPr H 3-I OCH _Two HOS C9.107 iPr H 3-I OCH _Two HOS C9.108 nBu H 3-I OCH _Two HOS C9.109 FCH _Two H 3-I OCH _Two HOS C9.110 F _Two CH H 3-I OCH _Two HOS C9.111 F _Three CH 3-I OCH _Two HOS C9.112 ClCH _Two H 3-I OCH _Two HOS C9.113 Cl _Two CH H 3-I OCH _Two HOS C9.114 BrCH _Two H 3-I OCH _Two HOS C9.115 FClCH H 3-I OCH _Two HOS C10.1 Me H 2-CF _Three OCH _Two HOS 178 C10.2 Me H 2-CF _Three SCH _Two HOS C10.3 Me H 2-CF _Three OCH _Two HOO 145-147 C10.4 MeO H 2-CF _Three OCH _Two HOS 133-135 C10.5 MeO H 2-CF _Three OCH _Two HOO 69-71 C10.6 Et H 2-CF _Three OCH _Two HOS C10.7 nPr H 2-CF _Three OCH _Two HOS C10.8 iPr H 2-CF _Three OCH _Two HOS C10.9 nBu H 2-CF _Three OCH _Two HOS C10.10 FCH _Two H 2-CF _Three OCH _Two HOS C10.11 F _Two CH H 2-CF _Three OCH _Two HOS C10.12 F _Three CH 2-CF _Three OCH _Two HOS C10.13 ClCH _Two H 2-CF _Three OCH _Two HOS C10.14 Cl _Two CH H 2-CF _Three OCH _Two HOS C10.15 BrCH _Two H 2-CF _Three OCH _Two HOS C10.16 FClCH H 2-CF _Three OCH _Two HOS C10.17 Me H 3-CF _Three OCH _Two HOS 174-175 C10.18 Me H 3-CF _Three SCH _Two HOS C10.19 Me H 3-CF _Three OCH _Two HOO C10.20 MeO H 3-CF _Three OCH _Two HOS 142-146 C10.21 MeO H 3-CF _Three OCH _Two HOO C10.22 Et H 3-CF _Three OCH _Two HOS C10.23 nPr H 3-CF _Three OCH _Two HOS C10.24 iPr H 3-CF _Three OCH _Two HOS C10.25 nBu H 3-CF _Three OCH _Two HOS C10.26 FCH _Two H 3-CF _Three OCH _Two HOS C10.27 F _Two CH H 3-CF _Three OCH _Two HOS C10.28 F _Three CH 3-CF _Three OCH _Two HOS C10.29 ClCH _Two H 3-CF _Three OCH _Two HOS C10.30 Cl _Two CH H 3-CF _Three OCH _Two HOS C10.31 BrCH _Two H 3-CF _Three OCH _Two HOS C10.32 FClCH H 3-CF _Three OCH _Two HOS C10.33 iPr H 3-CHO OCH _Two HOS C10.34 nBu H 3-CHO OCH _Two HOS C10.35 FCH _Two H 3-CHO OCH _Two HOS C10.36 F _Two CH H 3-CHO OCH _Two HOS C10.37 F _Three CH 3-CHO OCH _Two HOS C10.38 ClCH _Two H 3-CHO OCH _Two HOS C10.39 Cl _Two CH H 3-CHO OCH _Two HOS C10.40 BrCH _Two H 3-CHO OCH _Two HOS C10.41 FClCH H 3-CHO OCH _Two HOS C10.42 Me H 2-COMe OCH _Two HOS 134-137 C10.43 MeO H 2-COMe OCH _Two HOS C10.44 Me H 3-COMe OCH _Two HOS 233-238 C10.45 MeO H 3-COMe OCH _Two HOS C10.46 Me H 2-NO _Two OCH _Two HOS 191-193 C10.47 Me H 2-NO _Two SCH _Two HOS C10.48 MeO H 2-NO _Two OCH _Two HOS 184-186 C10.49 Me H 2-NO _Two OCH _Two HOO 162-165 C10.50 MeO H 2-NO _Two OCH _Two HOO 130-132 C10.51 Et H 2-NO _Two OCH _Two HOS C10.52 nPr H 2-NO _Two OCH _Two HOS C10.53 iPr H 2-NO _Two OCH _Two HOS C10.54 nBu H 2-NO _Two OCH _Two HOS C10.55 FCH _Two H 2-NO _Two OCH _Two HOS C10.56 F _Two CH H 2-NO _Two OCH _Two HOS C10.57 F _Three CH 2-NO _Two OCH _Two HOS C10.58 ClCH _Two H 2-NO _Two OCH _Two HOS C10.59 Cl _Two CH H 2-NO _Two OCH _Two HOS C10.60 BrCH _Two H 2-NO _Two OCH _Two HOS C10.61 FClCH H 2-NO _Two OCH _Two HOS C10.62 Me H 3-NO _Two OCH _Two HOS 188-190 C10.63 Me H 3-NO _Two SCH _Two HOS C10.64 MeO H 3-NO _Two OCH _Two HOS 198-200 C10.65 Me H 3-NO _Two OCH _Two HOO 148-150 C10.66 MeO H 3-NO _Two OCH _Two HOO 113-115 C10.67 Et H 3-NO _Two OCH _Two HOS C10.68 nPr H 3-NO _Two OCH _Two HOS C10.69 iPr H 3-NO _Two OCH _Two HOS C10.70 nBu H 3-NO _Two OCH _Two HOS C10.71 FCH _Two H 3-NO _Two OCH _Two HOS C10.72 F _Two CH H 3-NO _Two OCH _Two HOS C10.73 F _Three CH 3-NO _Two OCH _Two HOS C10.74 ClCH _Two H 3-NO _Two OCH _Two HOS C10.75 Cl _Two CH H 3-NO _Two OCH _Two HOS C10.76 BrCH _Two H 3-NO _Two OCH _Two HOS C10.77 FClCH H 3-NO _Two OCH _Two HOS C10.78 Me H 2-CO _Two Me OCH _Two HOS 192-193 C10.79 MeO H 2-CO _Two Me OCH _Two HOS C10.80 Me H 2-CO _Two Me OCH _Two HOO C10.81 MeO H 2-CO _Two Me OCH _Two HOO C10.82 Me H 2-CO _Two Et OCH _Two HOS 140 C10.83 MeO H 2-CO _Two Et OCH _Two HOS C10.84 Me H 2-CO _Two nPr OCH _Two HOS 127-128 C10.85 MeO H 2-CO _Two nPr OCH _Two HOS C10.86 Me H 2-CO _Two iPr OCH _Two HOS 127-128 C10.87 MeO H 2-CO _Two iPr OCH _Two HOS C10.88 Me H 3-CO _Two Me OCH _Two HOS 167-168 C10.89 MeO H 3-CO _Two Me OCH _Two HOS C10.90 Me H 3-CO _Two Me OCH _Two HOO C10.91 MeO H 3-CO _Two Me OCH _Two HOO C10.92 Me H 3-CO _Two Et OCH _Two HOS 164-165 C10.93 MeO H 3-CO _Two Et OCH _Two HOS C10.94 Me H 3-CO _Two nPr OCH _Two HOS 129 C10.95 MeO H 3-CO _Two nPr OCH _Two HOS C10.96 Me H 3-CO _Two iPr OCH _Two HOS 153.5-155 C10.97 MeO H 3-CO _Two iPr OCH _Two HOS C10.98 Me H 2-CHO OCH _Two HOS 174-176 C10.99 Me H 2-CHO SCH _Two HOS C10.100 MeO H 2-CHO OCH _Two HOS C10.101 MeO H 2-CHO OCH _Two HOO C10.102 Et H 2-CHO OCH _Two HOS C10.103 nPr H 2-CHO OCH _Two HOS C10.104 iPr H 2-CHO OCH _Two HOS C10.105 nBu H 2-CHO OCH _Two HOS C10.106 FCH _Two H 2-CHO OCH _Two HOS C10.107 F _Two CH H 2-CHO OCH _Two HOS C10.108 F _Three CH 2-CHO OCH _Two HOS C10.109 ClCH _Two H 2-CHO OCH _Two HOS C10.110 Cl _Two CH H 2-CHO OCH _Two HOS C10.111 BrCH _Two H 2-CHO OCH _Two HOS C10.112 FClCH H 2-CHO OCH _Two HOS C10.113 Me H 3-CHO OCH _Two HOS C10.114 Me H 3-CHO SCH _Two HOS C10.115 MeO H 3-CHO OCH _Two HOS C10.116 Et H 3-CHO OCH _Two HOS C10.117 nPr H 3-CHO OCH _Two HOS C11.1 Me H 2,3-Me _Two OCH _Two HOS 207-209 C11.2 Me H 2,3-Me _Two SCH _Two HOS C11.3 Me H 2,3-Me _Two OCH _Two HOO C11.4 MeO H 2,3-Me _Two OCH _Two HOS 178-180 C11.5 MeO H 2,3-Me _Two OCH _Two HOO C11.6 Et H 2,3-Me _Two OCH _Two HOS C11.7 nPr H 2,3-Me _Two OCH _Two HOS C11.8 iPr H 2,3-Me _Two OCH _Two HOS C11.9 nBu H 2,3-Me _Two OCH _Two HOS C11.10 FCH _Two H 2,3-Me _Two OCH _Two HOS C11.11 F _Two CH H 2,3-Me _Two OCH _Two HOS C11.12 F _Three CH 2,3-Me _Two OCH _Two HOS C11.13 ClCH _Two H 2,3-Me _Two OCH _Two HOS C11.14 Cl _Two CH H 2,3-Me _Two OCH _Two HOS C11.15 BrCH _Two H 2,3-Me _Two OCH _Two HOS C11.16 FClCH H 2,3-Me _Two OCH _Two HOS C11.17 Me H 2,5-Me _Two OCH _Two HOS 90-94 C11.18 Me H 2,5-Me _Two SCH _Two HOS C11.19 Me H 2,5-Me _Two OCH _Two HOO C11.20 MeO H 2,5-Me _Two OCH _Two HOS 127-128 C11.21 MeO H 2,5-Me _Two OCH _Two HOO C11.22 Et H 2,5-Me _Two OCH _Two HOS C11.23 nPr H 2,5-Me _Two OCH _Two HOS C11.24 iPr H 2,5-Me _Two OCH _Two HOS C11.26 FCH _Two H 2,5-Me _Two OCH _Two HOS C11.27 F _Two CH H 2,5-Me _Two OCH _Two HOS C11.28 F _Three CH 2,5-Me _Two OCH _Two HOS C11.29 ClCH _Two H 2,5-Me _Two OCH _Two HOS C11.30 Cl _Two CH H 2,5-Me _Two OCH _Two HOS C11.31 BrCH _Two H 2,5-Me _Two OCH _Two HOS C11.32 FClCH H 2,5-Me _Two OCH _Two HOS C11.33 Me H 2,6-Me _Two OCH _Two HOS 198-204 C11.34 Me H 2,6-Me _Two SCH _Two HOS C11.35 MeO H 2,6-Me _Two OCH _Two HOS C11.36 MeO H 2,6-Me _Two OCH _Two HOO C11.37 Et H 2,6-Me _Two OCH _Two HOS C11.38 nPr H 2,6-Me _Two OCH _Two HOS C11.39 iPr H 2,6-Me _Two OCH _Two HOS C11.40 nBu H 2,6-Me _Two OCH _Two HOS C11.41 FCH _Two H 2,6-Me _Two OCH _Two HOS C11.42 F _Two CH H 2,6-Me _Two OCH _Two HOS C11.43 F _Three CH 2,6-Me _Two OCH _Two HOS C11.44 ClCH _Two H 2,6-Me _Two OCH _Two HOS C11.45 Cl _Two CH H 2,6-Me _Two OCH _Two HOS C11.46 BrCH _Two H 2,6-Me _Two OCH _Two HOS C11.47 FClCH H 2,6-Me _Two OCH _Two HOS C11.48 Me H 3,5-Me _Two OCH _Two HOS 151 C11.49 Me H 3,5-Me _Two SCH _Two HOS C11.50 MeO H 3,5-Me _Two OCH _Two HOS C11.51 MeO H 3,5-Me _Two OCH _Two HOO C11.52 Et H 3,5-Me _Two OCH _Two HOS C11.53 nPr H 3,5-Me _Two OCH _Two HOS C11.54 iPr H 3,5-Me _Two OCH _Two HOS C11.55 nBu H 3,5-Me _Two OCH _Two HOS C11.56 FCH _Two H 3,5-Me _Two OCH _Two HOS C11.57 F _Two CH H 3,5-Me _Two OCH _Two HOS C11.58 F _Three CH 3,5-Me _Two OCH _Two HOS C11.59 ClCH _Two H 3,5-Me _Two OCH _Two HOS C11.60 Cl _Two CH H 3,5-Me _Two OCH _Two HOS C11.61 BrCH _Two H 3,5-Me _Two OCH _Two HOS C11.62 FClCH H 3,5-Me _Two OCH _Two HOS C11.63 Me H 2,3,5-Me _Three OCH _Two HOS 215-220 C11.64 MeO H 2,3,5-Me _Three OCH _Two HOS 158-160 C11.65 Me H 2,3,5-Me _Three OCH _Two HOO C11.66 MeO H 2,3,5-Me _Three OCH _Two HOO C11.67 Et H 2,3,5-Me _Three OCH _Two HOS C11.68 nPr H 2,3,5-Me _Three OCH _Two HOS C11.69 iPr H 2,3,5-Me _Three OCH _Two HOS C11.70 nBu H 2,3,5-Me _Three OCH _Two HOS C11.71 FCH _Two H 2,3,5-Me _Three OCH _Two HOS C11.72 F _Two CH H 2,3,5-Me _Three OCH _Two HOS C11.73 F _Three CH 2,3,5-Me _Three OCH _Two HOS C11.74 ClCH _Two H 2,3,5-Me _Three OCH _Two HOS C11.75 Cl _Two CH H 2,3,5-Me _Three OCH _Two HOS C11.76 BrCH _Two H 2,3,5-Me _Three OCH _Two HOS C11.77 FClCH H 2,3,5-Me _Three OCH _Two HOS C11.78 Me H 2,3,6-Me _Three OCH _Two HOS 217-225 C11.79 MeO H 2,3,6-Me _Three OCH _Two HOS 177-179 C11.80 Me H 2,3,6-Me _Three OCH _Two HOO C11.81 MeO H 2,3,6-Me _Three OCH _Two HOO C11.82 Et H 2,3,6-Me _Three OCH _Two HOS C11.83 nPr H 2,3,6-Me _Three OCH _Two HOS C11.84 iPr H 2,3,6-Me _Three OCH _Two HOS C11.85 nBu H 2,3,6-Me _Three OCH _Two HOS C11.86 FCH _Two H 2,3,6-Me _Three OCH _Two HOS C11.87 F _Two CH H 2,3,6-Me _Three OCH _Two HOS C11.88 F _Three CH 2,3,6-Me _Three OCH _Two HOS C11.89 ClCH _Two H 2,3,6-Me _Three OCH _Two HOS C11.90 Cl _Two CH H 2,3,6-Me _Three OCH _Two HOS C11.91 BrCH _Two H 2,3,6-Me _Three OCH _Two HOS C11.92 FClCH H 2,3,6-Me _Three OCH _Two HOS C11.93 Me H 2,3,5,6-Me _Four OCH _Two HOS C11.94 Et H 2,3,5,6-Me _Four OCH _Two HOS C11.95 nPr H 2,3,5,6-Me _Four OCH _Two HOS C11.96 iPr H 2,3,5,6-Me _Four OCH _Two HOS C11.97 nBu H 2,3,5,6-Me _Four OCH _Two HOS C11.98 FCH _Two H 2,3,5,6-Me _Four OCH _Two HOS C11.99 F _Two CH H 2,3,5,6-Me _Four OCH _Two HOS C11.100 F _Three CH 2,3,5,6-Me _Four OCH _Two HOS C11.101 ClCH _Two H 2,3,5,6-Me _Four OCH _Two HOS C11.102 Cl _Two CH H 2,3,5,6-Me _Four OCH _Two HOS C11.103 BrCH _Two H 2,3,5,6-Me _Four OCH _Two HOS C11.104 FClCH H 2,3,5,6-Me _Four OCH _Two HOS C12.1 Me H 2,3- (OMe) _Two OCH _Two HOS C12.2 Me H 2,3- (OMe) _Two SCH _Two HOS C12.3 MeO H 2,3- (OMe) _Two OCH _Two HOS C12.4 Me H 2,3- (OMe) _Two OCH _Two HOO C12.5 MeO H 2,3- (OMe) _Two OCH _Two HOO C12.6 Et H 2,3- (OMe) _Two OCH _Two HOS C12.7 nPr H 2,3- (OMe) _Two OCH _Two HOS C12.8 iPr H 2,3- (OMe) _Two OCH _Two HOS C12.9 nBu H 2,3- (OMe) _Two OCH _Two HOS C12.10 FCH _Two H 2,3- (OMe) _Two OCH _Two HOS C12.11 F _Two CH H 2,3- (OMe) _Two OCH _Two HOS C12.12 F _Three CH 2,3- (OMe) _Two OCH _Two HOS C12.13 ClCH _Two H 2,3- (OMe) _Two OCH _Two HOS C12.14 Cl _Two CH H 2,3- (OMe) _Two OCH _Two HOS C12.15 BrCH _Two H 2,3- (OMe) _Two OCH _Two HOS C12.16 FClCH H 2,3- (OMe) _Two OCH _Two HOS C12.17 Me H 2,5- (OMe) _Two OCH _Two HOS C12.18 Me H 2,5- (OMe) _Two SCH _Two HOS C12.19 MeO H 2,5- (OMe) _Two OCH _Two HOS C12.20 Et H 2,5- (OMe) _Two OCH _Two HOS C12.21 nPr H 2,5- (OMe) _Two OCH _Two HOS C12.22 iPr H 2,5- (OMe) _Two OCH _Two HOS C12.23 nBu H 2,5- (OMe) _Two OCH _Two HOS C12.24 FCH _Two H 2,5- (OMe) _Two OCH _Two HOS C12.25 F _Two CH H 2,5- (OMe) _Two OCH _Two HOS C12.26 F _Three CH 2,5- (OMe) _Two OCH _Two HOS C12.27 ClCH _Two H 2,5- (OMe) _Two OCH _Two HOS C12.28 Cl _Two CH H 2,5- (OMe) _Two OCH _Two HOS C12.29 BrCH _Two H 2,5- (OMe) _Two OCH _Two HOS C12.30 FClCH H 2,5- (OMe) _Two OCH _Two HOS C12.31 Me H 2,6- (OMe) _Two OCH _Two HOS C12.32 Me H 2,6- (OMe) _Two SCH _Two HOS C12.33 MeO H 2,6- (OMe) _Two OCH _Two HOS C12.34 Et H 2,6- (OMe) _Two OCH _Two HOS C12.35 nPr H 2,6- (OMe) _Two OCH _Two HOS C12.36 iPr H 2,6- (OMe) _Two OCH _Two HOS C12.37 nBu H 2,6- (OMe) _Two OCH _Two HOS C12.38 FCH _Two H 2,6- (OMe) _Two OCH _Two HOS C12.39 F _Two CH H 2,6- (OMe) _Two OCH _Two HOS C12.40 F _Three CH 2,6- (OMe) _Two OCH _Two HOS C12.41 ClCH _Two H 2,6- (OMe) _Two OCH _Two HOS C12.42 Cl _Two CH H 2,6- (OMe) _Two OCH _Two HOS C12.43 BrCH _Two H 2,6- (OMe) _Two OCH _Two HOS C12.44 FClCH H 2,6- (OMe) _Two OCH _Two HOS C12.45 Me H 3,5- (OMe) _Two OCH _Two HOS amorphous C12.46 Me H 3,5- (OMe) _Two SCH _Two HOS C12.47 MeO H 3,5- (OMe) _Two OCH _Two HOS 110-113 C12.48 Et H 3,5- (OMe) _Two OCH _Two HOS C12.49 nPr H 3,5- (OMe) _Two OCH _Two HOS C12.50 iPr H 3,5- (OMe) _Two OCH _Two HOS C12.51 nBu H 3,5- (OMe) _Two OCH _Two HOS C12.52 FCH _Two H 3,5- (OMe) _Two OCH _Two HOS C12.53 F _Two CH H 3,5- (OMe) _Two OCH _Two HOS C12.54 F _Three CH 3,5- (OMe) _Two OCH _Two HOS C12.55 ClCH _Two H 3,5- (OMe) _Two OCH _Two HOS C12.56 Cl _Two CH H 3,5- (OMe) _Two OCH _Two HOS C12.57 BrCH _Two H 3,5- (OMe) _Two OCH _Two HOS C12.58 FClCH H 3,5- (OMe) _Two OCH _Two HOS C12.59 Me H 2,3,5- (OMe) _Three OCH _Two HOS C12.60 Et H 2,3,5- (OMe) _Three OCH _Two HOS C12.61 nPr H 2,3,5- (OMe) _Three OCH _Two HOS C12.62 iPr H 2,3,5- (OMe) _Three OCH _Two HOS C12.63 nBu H 2,3,5- (OMe) _Three OCH _Two HOS C12.64 FCH _Two H 2,3,5- (OMe) _Three OCH _Two HOS C12.65 F _Two CH H 2,3,5- (OMe) _Three OCH _Two HOS C12.66 F _Three CH 2,3,5- (OMe) _Three OCH _Two HOS C12.67 ClCH _Two H 2,3,5- (OMe) _Three OCH _Two HOS C12.68 Cl _Two CH H 2,3,5- (OMe) _Three OCH _Two HOS C12.69 BrCH _Two H 2,3,5- (OMe) _Three OCH _Two HOS C12.70 FClCH H 2,3,5- (OMe) _Three OCH _Two HOS C12.71 Me H 2,3,6- (OMe) _Three OCH _Two HOS C12.72 Et H 2,3,6- (OMe) _Three OCH _Two HOS C12.73 nPr H 2,3,6- (OMe) _Three OCH _Two HOS C12.74 iPr H 2,3,6- (OMe) _Three OCH _Two HOS C12.75 nBu H 2,3,6- (OMe) _Three OCH _Two HOS C12.76 FCH _Two H 2,3,6- (OMe) _Three OCH _Two HOS C12.77 F _Two CH H 2,3,6- (OMe) _Three OCH _Two HOS C12.78 F _Three CH 2,3,6- (OMe) _Three OCH _Two HOS C12.79 ClCH _Two H 2,3,6- (OMe) _Three OCH _Two HOS C12.80 Cl _Two CH H 2,3,6- (OMe) _Three OCH _Two HOS C12.81 BrCH _Two H 2,3,6- (OMe) _Three OCH _Two HOS C12.82 FClCH H 2,3,6- (OMe) _Three OCH _Two HOS C12.83 Me H 2,3,5,6- (OMe) _Four OCH _Two HOS C12.84 Et H 2,3,5,6- (OMe) _Four OCH _Two HOS C12.85 nPr H 2,3,5,6- (OMe) _Four OCH _Two HOS C12.86 iPr H 2,3,5,6- (OMe) _Four OCH _Two HOS C12.87 nBu H 2,3,5,6- (OMe) _Four OCH _Two HOS C12.88 FCH _Two H 2,3,5,6- (OMe) _Four OCH _Two HOS C12.89 F _Two CH H 2,3,5,6- (OMe) _Four OCH _Two HOS C12.90 F _Three CH 2,3,5,6- (OMe) _Four OCH _Two HOS C12.91 ClCH _Two H 2,3,5,6- (OMe) _Four OCH _Two HOS C12.92 Cl _Two CH H 2,3,5,6- (OMe) _Four OCH _Two HOS C12.93 BrCH _Two H 2,3,5,6- (OMe) _Four OCH _Two HOS C12.94 FClCH H 2,3,5,6- (OMe) _Four OCH _Two HOS C13.1 Me H 2,3-F _Two OCH _Two HOS C13.2 Me H 2,3-F _Two SCH _Two HOS C13.3 Me H 2,3-F _Two OCH _Two HOO C13.4 MeO H 2,3-F _Two OCH _Two HOS C13.5 MeO H 2,3-F _Two OCH _Two HOO C13.6 Et H 2,3-F _Two OCH _Two HOS C13.7 nPr H 2,3-F _Two OCH _Two HOS C13.8 iPr H 2,3-F _Two OCH _Two HOS C13.9 nBu H 2,3-F _Two OCH _Two HOS C13.10 FCH _Two H 2,3-F _Two OCH _Two HOS C13.11 F _Two CH H 2,3-F _Two OCH _Two HOS C13.12 F _Three CH 2,3-F _Two OCH _Two HOS C13.13 ClCH _Two H 2,3-F _Two OCH _Two HOS C13.14 Cl _Two CH H 2,3-F _Two OCH _Two HOS C13.15 BrCH _Two H 2,3-F _Two OCH _Two HOS C13.16 FClCH H 2,3-F _Two OCH _Two HOS C13.17 Me H 2,5-F _Two OCH _Two HOS C13.18 Me H 2,5-F _Two SCH _Two HOS C13.19 MeO H 2,5-F _Two OCH _Two HOS C13.20 Et H 2,5-F _Two OCH _Two HOS C13.21 nPr H 2,5-F _Two OCH _Two HOS C13.22 iPr H 2,5-F _Two OCH _Two HOS C13.23 nBu H 2,5-F _Two OCH _Two HOS C13.24 FCH _Two H 2,5-F _Two OCH _Two HOS C13.25 F _Two CH H 2,5-F _Two OCH _Two HOS C13.26 F _Three CH 2,5-F _Two OCH _Two HOS C13.27 ClCH _Two H 2,5-F _Two OCH _Two HOS C13.28 Cl _Two CH H 2,5-F _Two OCH _Two HOS C13.29 BrCH _Two H 2,5-F _Two OCH _Two HOS C13.30 FClCH H 2,5-F _Two OCH _Two HOS C13.31 Me H 2,6-F _Two OCH _Two HOS C13.32 Me H 2,6-F _Two SCH _Two HOS C13.33 MeO H 2,6-F _Two OCH _Two HOS C13.34 Et H 2,6-F _Two OCH _Two HOS C13.35 nPr H 2,6-F _Two OCH _Two HOS C13.36 iPr H 2,6-F _Two OCH _Two HOS C13.37 nBu H 2,6-F _Two OCH _Two HOS C13.38 FCH _Two H 2,6-F _Two OCH _Two HOS C13.39 F _Two CH H 2,6-F _Two OCH _Two HOS C13.40 F _Three CH 2,6-F _Two OCH _Two HOS C13.41 ClCH _Two H 2,6-F _Two OCH _Two HOS C13.42 Cl _Two CH H 2,6-F _Two OCH _Two HOS C13.43 BrCH _Two H 2,6-F _Two OCH _Two HOS C13.44 FClCH H 2,6-F _Two OCH _Two HOS C13.45 Me H 3,5-F _Two OCH _Two HOS C13.46 Me H 3,5-F _Two SCH _Two HOS C13.47 MeO H 3,5-F _Two OCH _Two HOS C13.48 Et H 3,5-F _Two OCH _Two HOS C13.49 nPr H 3,5-F _Two OCH _Two HOS C13.50 iPr H 3,5-F _Two OCH _Two HOS C13.51 nBu H 3,5-F _Two OCH _Two HOS C13.52 FCH _Two H 3,5-F _Two OCH _Two HOS C13.53 F _Two CH H 3,5-F _Two OCH _Two HOS C13.54 F _Three CH 3,5-F _Two OCH _Two HOS C13.55 ClCH _Two H 3,5-F _Two OCH _Two HOS C13.56 Cl _Two CH H 3,5-F _Two OCH _Two HOS C13.57 BrCH _Two H 3,5-F _Two OCH _Two HOS C13.58 FClCH H 3,5-F _Two OCH _Two HOS C13.59 Me H 2,3,5-F _Three OCH _Two HOS C13.60 Et H 2,3,5-F _Three OCH _Two HOS C13.61 nPr H 2,3,5-F _Three OCH _Two HOS C13.62 iPr H 2,3,5-F _Three OCH _Two HOS C13.63 nBu H 2,3,5-F _Three OCH _Two HOS C13.64 FCH _Two H 2,3,5-F _Three OCH _Two HOS C13.65 F _Two CH H 2,3,5-F _Three OCH _Two HOS C13.66 F _Three CH 2,3,5-F _Three OCH _Two HOS C13.67 ClCH _Two H 2,3,5-F _Three OCH _Two HOS C13.68 Cl _Two CH H 2,3,5-F _Three OCH _Two HOS C13.69 BrCH _Two H 2,3,5-F _Three OCH _Two HOS C13.70 FClCH H 2,3,5-F _Three OCH _Two HOS C13.71 Me H 2,3,6-F _Three OCH _Two HOS C13.72 Et H 2,3,6-F _Three OCH _Two HOS C13.73 nPr H 2,3,6-F _Three OCH _Two HOS C13.74 iPr H 2,3,6-F _Three OCH _Two HOS C13.75 nBu H 2,3,6-F _Three OCH _Two HOS C13.76 FCH _Two H 2,3,6-F _Three OCH _Two HOS C13.77 F _Two CH H 2,3,6-F _Three OCH _Two HOS C13.78 F _Three CH 2,3,6-F _Three OCH _Two HOS C13.79 ClCH _Two H 2,3,6-F _Three OCH _Two HOS C13.80 Cl _Two CH H 2,3,6-F _Three OCH _Two HOS C13.81 BrCH _Two H 2,3,6-F _Three OCH _Two HOS C13.82 FClCH H 2,3,6-F _Three OCH _Two HOS C13.83 Me H 2,3,5,6-F _Four OCH _Two HOS C13.84 Et H 2,3,5,6-F _Four OCH _Two HOS C13.85 nPr H 2,3,5,6-F _Four OCH _Two HOS C13.86 iPr H 2,3,5,6-F _Four OCH _Two HOS C13.87 nBu H 2,3,5,6-F _Four OCH _Two HOS C13.88 FCH _Two H 2,3,5,6-F _Four OCH _Two HOS C13.89 F _Two CH H 2,3,5,6-F _Four OCH _Two HOS C13.90 F _Three CH 2,3,5,6-F _Four OCH _Two HOS C13.91 ClCH _Two H 2,3,5,6-F _Four OCH _Two HOS C13.92 Cl _Two CH H 2,3,5,6-F _Two OCH _Two HOS C13.93 BrCH _Two H 2,3,5,6-F _Four OCH _Two HOS C13.94 FClCH H 2,3,5,6-F _Four OCH _Two HOS C14.1 Me H 2,3-Cl _Two OCH _Two HOS C14.2 Me H 2,3-Cl _Two SCH _Two HOS C14.3 MeO H 2,3-Cl _Two OCH _Two HOS C14.4 Et H 2,3-Cl _Two OCH _Two HOS C14.5 nPr H 2,3-Cl _Two OCH _Two HOS C14.6 iPr H 2,3-Cl _Two OCH _Two HOS C14.7 nBu H 2,3-Cl _Two OCH _Two HOS C14.8 FCH _Two H 2,3-Cl _Two OCH _Two HOS C14.9 F _Two CH H 2,3-Cl _Two OCH _Two HOS C14.10 F _Three CH 2,3-Cl _Two OCH _Two HOS C14.11 ClCH _Two H 2,3-Cl _Two OCH _Two HOS C14.12 Cl _Two CH H 2,3-Cl _Two OCH _Two HOS C14.13 BrCH _Two H 2,3-Cl _Two OCH _Two HOS C14.14 FClCH H 2,3-Cl _Two OCH _Two HOS C14.15 Me H 2,5-Cl _Two OCH _Two HOS 188 C14.16 Me H 2,5-Cl _Two SCH _Two HOS C14.17 Me H 2,5-Cl _Two OCH _Two HOO C14.18 MeO H 2,5-Cl _Two OCH _Two HOS 131-133 C14.19 MeO H 2,5-Cl _Two OCH _Two HOO C14.20 Et H 2,5-Cl _Two OCH _Two HOS C14.21 nPr H 2,5-Cl _Two OCH _Two HOS C14.22 iPr H 2,5-Cl _Two OCH _Two HOS C14.23 nBu H 2,5-Cl _Two OCH _Two HOS C14.24 FCH _Two H 2,5-Cl _Two OCH _Two HOS C14.25 F _Two CH H 2,5-Cl _Two OCH _Two HOS C14.26 F _Three CH 2,5-Cl _Two OCH _Two HOS C14.27 ClCH _Two H 2,5-Cl _Two OCH _Two HOS C14.28 Cl _Two CH H 2,5-Cl _Two OCH _Two HOS C14.29 BrCH _Two H 2,5-Cl _Two OCH _Two HOS C14.30 FClCH H 2,5-Cl _Two OCH _Two HOS C14.31 Me H 2,6-Cl _Two OCH _Two HOS 169-172 C14.32 Me H 2,6-Cl _Two SCH _Two HOS C14.33 MeO H 2,6-Cl _Two OCH _Two HOS C14.34 Et H 2,6-Cl _Two OCH _Two HOS C14.35 nPr H 2,6-Cl _Two OCH _Two HOS C14.36 iPr H 2,6-Cl _Two OCH _Two HOS C14.37 nBu H 2,6-Cl _Two OCH _Two HOS C14.38 FCH _Two H 2,6-Cl _Two OCH _Two HOS C14.39 F _Two CH H 2,6-Cl _Two OCH _Two HOS C14.40 F _Three CH 2,6-Cl _Two OCH _Two HOS C14.41 ClCH _Two H 2,6-Cl _Two OCH _Two HOS C14.42 Cl _Two CH H 2,6-Cl _Two OCH _Two HOS C14.43 BrCH _Two H 2,6-Cl _Two OCH _Two HOS C14.44 FClCH H 2,6-Cl _Two OCH _Two HOS C14.45 Me H 3,5-Cl _Two OCH _Two HOS 173.5-175 C14.46 Me H 3,5-Cl _Two SCH _Two HOS C14.47 Me H 3,5-Cl _Two OCH _Two HOO C14.48 MeO H 3,5-Cl _Two OCH _Two HOS C14.49 MeO H 3,5-Cl _Two SCH _Two HOS C14.50 MeO H 3,5-Cl _Two OCH _Two HOO C14.51 Et H 3,5-Cl _Two OCH _Two HOS C14.52 nPr H 3,5-Cl _Two OCH _Two HOS C14.53 iPr H 3,5-Cl _Two OCH _Two HOS C14.54 nBu H 3,5-Cl _Two OCH _Two HOS C14.55 FCH _Two H 3,5-Cl _Two OCH _Two HOS C14.56 F _Two CH H 3,5-Cl _Two OCH _Two HOS C14.57 F _Three CH 3,5-Cl _Two OCH _Two HOS C14.58 ClCH _Two H 3,5-Cl _Two OCH _Two HOS C14.59 Cl _Two CH H 3,5-Cl _Two OCH _Two HOS C14.60 BrCH _Two H 3,5-Cl _Two OCH _Two HOS C14.61 FClCH H 3,5-Cl _Two OCH _Two HOS C14.62 Me H 2,3,5-Cl _Three OCH _Two HOS C14.63 Et H 2,3,5-Cl _Three OCH _Two HOS C14.64 nPr H 2,3,5-Cl _Three OCH _Two HOS C14.65 iPr H 2,3,5-Cl _Three OCH _Two HOS C14.66 nBu H 2,3,5-Cl _Three OCH _Two HOS C14.67 FCH _Two H 2,3,5-Cl _Three OCH _Two HOS C14.68 F _Two CH H 2,3,5-Cl _Three OCH _Two HOS C14.69 F _Three CH 2,3,5-Cl _Three OCH _Two HOS C14.70 ClCH _Two H 2,3,5-Cl _Three OCH _Two HOS C14.71 Cl _Two CH H 2,3,5-Cl _Three OCH _Two HOS C14.72 BrCH _Two H 2,3,5-Cl _Three OCH _Two HOS C14.73 FClCH H 2,3,5-Cl _Three OCH _Two HOS C14.74 Me H 2,3,6-Cl _Three OCH _Two HOS 194-197 C14.75 MeO H 2,3,6-Cl _Three OCH _Two HOS C14.76 Et H 2,3,6-Cl _Three OCH _Two HOS C14.77 nPr H 2,3,6-Cl _Three OCH _Two HOS C14.78 iPr H 2,3,6-Cl _Three OCH _Two HOS C14.79 nBu H 2,3,6-Cl _Three OCH _Two HOS C14.80 FCH _Two H 2,3,6-Cl _Three OCH _Two HOS C14.81 F _Two CH H 2,3,6-Cl _Three OCH _Two HOS C14.82 F _Three CH 2,3,6-Cl _Three OCH _Two HOS C14.83 ClCH _Two H 2,3,6-Cl _Three OCH _Two HOS C14.84 Cl _Two CH H 2,3,6-Cl _Three OCH _Two HOS C14.85 BrCH _Two H 2,3,6-Cl _Three OCH _Two HOS C14.86 FClCH H 2,3,6-Cl _Three OCH _Two HOS C14.87 Me H 2,3,5,6-Cl _Four OCH _Two HOS C14.88 Et H 2,3,5,6-Cl _Four OCH _Two HOS C14.89 nPr H 2,3,5,6-Cl _Four OCH _Two HOS C14.90 iPr H 2,3,5,6-Cl _Four OCH _Two HOS C14.91 nBu H 2,3,5,6-Cl _Four OCH _Two HOS C14.92 FCH _Two H 2,3,5,6-Cl _Four OCH _Two HOS C14.93 F _Two CH H 2,3,5,6-Cl _Four OCH _Two HOS C14.94 F _Three CH 2,3,5,6-Cl _Four OCH _Two HOS C14.95 ClCH _Two H 2,3,5,6-Cl _Four OCH _Two HOS C14.96 Cl _Two CH H 2,3,5,6-Cl _Four OCH _Two HOS C14.97 BrCH _Two H 2,3,5,6-Cl _Four OCH _Two HOS C14.98 FClCH H 2,3,5,6-Cl _Four OCH _Two HOS C15.1 Me H 2,3-Br _Two OCH _Two HOS C15.2 Et H 2,3-Br _Two OCH _Two HOS C15.3 nPr H 2,3-Br _Two OCH _Two HOS C15.4 iPr H 2,3-Br _Two OCH _Two HOS C15.5 nBu H 2,3-Br _Two OCH _Two HOS C15.6 FCH _Two H 2,3-Br _Two OCH _Two HOS C15.7 F _Two CH H 2,3-Br _Two OCH _Two HOS C15.8 F _Three CH 2,3-Br _Two OCH _Two HOS C15.9 ClCH _Two H 2,3-Br _Two OCH _Two HOS C15.10 Cl _Two CH H 2,3-Br _Two OCH _Two HOS C15.11 BrCH _Two H 2,3-Br _Two OCH _Two HOS C15.12 FClCH H 2,3-Br _Two OCH _Two HOS C15.13 Me H 2,5-Br _Two OCH _Two HOS C15.14 Et H 2,5-Br _Two OCH _Two HOS C15.15 nPr H 2,5-Br _Two OCH _Two HOS C15.16 iPr H 2,5-Br _Two OCH _Two HOS C15.17 nBu H 2,5-Br _Two OCH _Two HOS C15.18 FCH _Two H 2,5-Br _Two OCH _Two HOS C15.19 F _Two CH H 2,5-Br _Two OCH _Two HOS C15.20 F _Three CH 2,5-Br _Two OCH _Two HOS C15.21 ClCH _Two H 2,5-Br _Two OCH _Two HOS C15.22 Cl _Two CH H 2,5-Br _Two OCH _Two HOS C15.23 BrCH _Two H 2,5-Br _Two OCH _Two HOS C15.24 FClCH H 2,5-Br _Two OCH _Two HOS C15.25 Me H 2,6-Br _Two OCH _Two HOS C15.26 Et H 2,6-Br _Two OCH _Two HOS C15.27 nPr H 2,6-Br _Two OCH _Two HOS C15.28 iPr H 2,6-Br _Two OCH _Two HOS C15.29 nBu H 2,6-Br _Two OCH _Two HOS C15.30 FCH _Two H 2,6-Br _Two OCH _Two HOS C15.31 F _Two CH H 2,6-Br _Two OCH _Two HOS C15.32 F _Three CH 2,6-Br _Two OCH _Two HOS C15.33 ClCH _Two H 2,6-Br _Two OCH _Two HOS C15.34 Cl _Two CH H 2,6-Br _Two OCH _Two HOS C15.35 BrCH _Two H 2,6-Br _Two OCH _Two HOS C15.36 FClCH H 2,6-Br _Two OCH _Two HOS C15.37 Me H 3,5-Br _Two OCH _Two HOS 198 (decomposed) C15.38 MeO H 3,5-Br _Two OCH _Two HOS C15.39 Et H 3,5-Br _Two OCH _Two HOS C15.40 nPr H 3,5-Br _Two OCH _Two HOS C15.41 iPr H 3,5-Br _Two OCH _Two HOS C15.42 nBu H 3,5-Br _Two OCH _Two HOS C15.43 FCH _Two H 3,5-Br _Two OCH _Two HOS C15.44 F _Two CH H 3,5-Br _Two OCH _Two HOS C15.45 F _Three CH 3,5-Br _Two OCH _Two HOS C15.46 ClCH _Two H 3,5-Br _Two OCH _Two HOS C15.47 Cl _Two CH H 3,5-Br _Two OCH _Two HOS C15.48 BrCH _Two H 3,5-Br _Two OCH _Two HOS C15.49 FClCH H 3,5-Br _Two OCH _Two HOS C15.50 Me H 2,3,5-Br _Three OCH _Two HOS C15.51 Et H 2,3,5-Br _Three OCH _Two HOS C15.52 nPr H 2,3,5-Br _Three OCH _Two HOS C15.53 iPr H 2,3,5-Br _Three OCH _Two HOS C15.54 nBu H 2,3,5-Br _Three OCH _Two HOS C15.55 FCH _Two H 2,3,5-Br _Three OCH _Two HOS C15.56 F _Two CH H 2,3,5-Br _Three OCH _Two HOS C15.57 F _Three CH 2,3,5-Br _Three OCH _Two HOS C15.58 ClCH _Two H 2,3,5-Br _Three OCH _Two HOS C15.59 Cl _Two CH H 2,3,5-Br _Three OCH _Two HOS C15.60 BrCH _Two H 2,3,5-Br _Three OCH _Two HOS C15.61 FClCH H 2,3,5-Br _Three OCH _Two HOS C15.62 Me H 2,3,6-Br _Three OCH _Two HOS C15.63 Et H 2,3,6-Br _Three OCH _Two HOS C15.64 nPr H 2,3,6-Br _Three OCH _Two HOS C15.65 iPr H 2,3,6-Br _Three OCH _Two HOS C15.66 nBu H 2,3,6-Br _Three OCH _Two HOS C15.67 FCH _Two H 2,3,6-Br _Three OCH _Two HOS C15.68 F _Two CH H 2,3,6-Br _Three OCH _Two HOS C15.69 F _Three CH 2,3,6-Br _Three OCH _Two HOS C15.70 ClCH _Two H 2,3,6-Br _Three OCH _Two HOS C15.71 Cl _Two CH H 2,3,6-Br _Three OCH _Two HOS C15.72 BrCH _Two H 2,3,6-Br _Three OCH _Two HOS C15.73 FClCH H 2,3,6-Br _Three OCH _Two HOS C15.74 Me H 2,3,5,6-Br _Four OCH _Two HOS C15.75 Et H 2,3,5,6-Br _Four OCH _Two HOS C15.76 nPr H 2,3,5,6-Br _Four OCH _Two HOS C15.77 iPr H 2,3,5,6-Br _Four OCH _Two HOS C15.78 nBu H 2,3,5,6-Br _Four OCH _Two HOS C15.79 FCH _Two H 2,3,5,6-Br _Four OCH _Two HOS C15.80 F _Two CH H 2,3,5,6-Br _Four OCH _Two HOS C15.81 F _Three CH 2,3,5,6-Br _Four OCH _Two HOS C15.82 ClCH _Two H 2,3,5,6-Br _Four OCH _Two HOS C15.83 Cl _Two CH H 2,3,5,6-Br _Four OCH _Two HOS C15.84 BrCH _Two H 2,3,5,6-Br _Four OCH _Two HOS C15.85 FClCH H 2,3,5,6-Br _Four OCH _Two HOS C16.1 Me H 2-F, 3-Me OCH _Two HOS C16.2 Me H 2-F, 3-Me SCH _Two HOS C16.3 Et H 2-F, 3-Me OCH _Two HOS C16.4 nPr H 2-F, 3-Me OCH _Two HOS C16.5 iPr H 2-F, 3-Me OCH _Two HOS C16.6 nBu H 2-F, 3-Me OCH _Two HOS C16.7 FCH _Two H 2-F, 3-Me OCH _Two HOS C16.8 F _Two CH H 2-F, 3-Me OCH _Two HOS C16.9 F _Three CH 2-F, 3-Me OCH _Two HOS C16.10 ClCH _Two H 2-F, 3-Me OCH _Two HOS C16.11 Cl _Two CH H 2-F, 3-Me OCH _Two HOS C16.12 Me H 2-F, 5-Me OCH _Two HOS C16.13 Me H 2-F, 5-Me SCH _Two HOS C16.14 Et H 2-F, 5-Me OCH _Two HOS C16.15 nPr H 2-F, 5-Me OCH _Two HOS C16.16 iPr H 2-F, 5-Me OCH _Two HOS C16.17 nBu H 2-F, 5-Me OCH _Two HOS C16.18 FCH _Two H 2-F, 5-Me OCH _Two HOS C16.19 F _Two CH H 2-F, 5-Me OCH _Two HOS C16.20 F _Three CH 2-F, 5-Me OCH _Two HOS C16.21 ClCH _Two H 2-F, 5-Me OCH _Two HOS C16.22 Cl _Two CH H 2-F, 5-Me OCH _Two HOS C16.23 Me H 3-F, 5-Me OCH _Two HOS C16.24 Me H 3-F, 5-Me SCH _Two HOS C16.25 Et H 3-F, 5-Me OCH _Two HOS C16.26 nPr H 3-F, 5-Me OCH _Two HOS C16.27 iPr H 3-F, 5-Me OCH _Two HOS C16.28 nBu H 3-F, 5-Me OCH _Two HOS C16.29 FCH _Two H 3-F, 5-Me OCH _Two HOS C16.30 F _Two CH H 3-F, 5-Me OCH _Two HOS C16.31 F _Three CH 3-F, 5-Me OCH _Two HOS C16.32 ClCH _Two H 3-F, 5-Me OCH _Two HOS C16.33 Cl _Two CH H 3-F, 5-Me OCH _Two HOS C16.34 Me H 2-Me, 3-F OCH _Two HOS C16.35 Me H 2-Me, 3-F SCH _Two HOS C16.36 Et H 2-Me, 3-F OCH _Two HOS C16.37 nPr H 2-Me, 3-F OCH _Two HOS C16.38 iPr H 2-Me, 3-F OCH _Two HOS C16.39 nBu H 2-Me, 3-F OCH _Two HOS C16.40 FCH _Two H 2-Me, 3-F OCH _Two HOS C16.41 F _Two CH H 2-Me, 3-F OCH _Two HOS C16.42 F _Three CH 2-Me, 3-F OCH _Two HOS C16.44 Cl _Two CH H 3-F, 2-Me OCH _Two HOS C16.45 Me H 2-F, 6-Me OCH _Two HOS C16.46 Me H 2-F, 6-Me SCH _Two HOS C16.47 Et H 2-F, 6-Me OCH _Two HOS C16.48 nPr H 2-F, 6-Me OCH _Two HOS C16.49 iPr H 2-F, 6-Me OCH _Two HOS C16.50 nBu H 2-F, 6-Me OCH _Two HOS C16.51 FCH _Two H 2-F, 6-Me OCH _Two HOS C16.52 F _Two CH H 2-F, 6-Me OCH _Two HOS C16.53 F _Three CH 2-F, 6-Me OCH _Two HOS C16.54 ClCH _Two H 2-F, 6-Me OCH _Two HOS C16.55 Cl _Two CH H 2-F, 6-Me OCH _Two HOS C16.56 Me H 2-Me, 5-F OCH _Two HOS C16.57 Me H 2-Me, 5-F SCH _Two HOS C16.58 Et H 2-Me, 5-F OCH _Two HOS C16.59 nPr H 2-Me, 5-F OCH _Two HOS C16.60 iPr H 2-Me, 5-F OCH _Two HOS C16.61 nBu H 2-Me, 5-F OCH _Two HOS C16.62 FCH _Two H 2-Me, 5-F OCH _Two HOS C16.63 F _Two CH H 2-Me, 5-F OCH _Two HOS C16.64 F _Three CH 2-Me, 5-F OCH _Two HOS C16.65 ClCH _Two H 2-Me, 5-F OCH _Two HOS C16.66 Cl _Two CH H 2-Me, 5-F OCH _Two HOS C16.67 Me H 2-Cl, 3-Me OCH _Two HOS C16.68 Me H 2-Cl, 3-Me SCH _Two HOS C16.69 Et H 2-Cl, 3-Me OCH _Two HOS C16.70 nPr H 2-Cl, 3-Me OCH _Two HOS C16.71 iPr H 2-Cl, 3-Me OCH _Two HOS C16.72 nBu H 2-Cl, 3-Me OCH _Two HOS C16.73 FCH _Two H 2-Cl, 3-Me OCH _Two HOS C16.74 F _Two CH H 2-Cl, 3-Me OCH _Two HOS C16.75 F _Three CH 2-Cl, 3-Me OCH _Two HOS C16.76 ClCH _Two H 2-Cl, 3-Me OCH _Two HOS C16.77 Cl _Two CH H 2-Cl, 3-Me OCH _Two HOS C16.78 Me H 2-Cl, 5-Me OCH _Two HOS C16.79 Me H 2-Cl, 5-Me SCH _Two HOS C16.80 Et H 2-Cl, 5-Me OCH _Two HOS C16.81 nPr H 2-Cl, 5-Me OCH _Two HOS C16.82 iPr H 2-Cl, 5-Me OCH _Two HOS C16.83 nBu H 2-Cl, 5-Me OCH _Two HOS C16.84 FCH _Two H 2-Cl, 5-Me OCH _Two HOS C16.85 F _Two CH H 2-Cl, 5-Me OCH _Two HOS C16.86 F _Three CH 2-Cl, 5-Me OCH _Two HOS C16.87 ClCH _Two H 2-Cl, 5-Me OCH _Two HOS C16.88 Cl _Two CH H 2-Cl, 5-Me OCH _Two HOS C16.89 Me H 3-Cl, 5-Me OCH _Two HOS C16.90 Me H 3-Cl, 5-Me SCH _Two HOS C16.91 Et H 3-Cl, 5-Me OCH _Two HOS C16.92 nPr H 3-Cl, 5-Me OCH _Two HOS C16.93 iPr H 3-Cl, 5-Me OCH _Two HOS C16.94 nBu H 3-Cl, 5-Me OCH _Two HOS C16.95 FCH _Two H 3-Cl, 5-Me OCH _Two HOS C16.96 F _Two CH H 3-Cl, 5-Me OCH _Two HOS C16.97 F _Three CH 3-Cl, 5-Me OCH _Two HOS C16.98 ClCH _Two H 3-Cl, 5-Me OCH _Two HOS C16.99 Cl _Two CH H 3-Cl, 5-Me OCH _Two HOS C16.100 Me H 2-Me, 3-Cl OCH _Two HOS C16.101 Me H 2-Me, 3-Cl SCH _Two HOS C16.102 Et H 2-Me, 3-Cl OCH _Two HOS C16.103 nPr H 2-Me, 3-Cl OCH _Two HOS C16.104 iPr H 2-Me, 3-Cl OCH _Two HOS C16.105 nBu H 2-Me, 3-Cl OCH _Two HOS C16.106 FCH _Two H 2-Me, 3-Cl OCH _Two HOS C16.107 F _Two CH H 2-Me, 3-Cl OCH _Two HOS C16.108 F _Three CH 2-Me, 3-Cl OCH _Two HOS C16.109 ClCH _Two H 2-Me, 3-Cl OCH _Two HOS C16.110 Cl _Two CH H 2-Me, 3-Cl OCH _Two HOS C16.111 Me H 2-Cl, 6-Me OCH _Two HOS C16.112 Me H 2-Cl, 6-Me SCH _Two HOS C16.113 MeO H 2-Cl, 6-Me OCH _Two HOS 184-187 C16.114 MeO H 2-Cl, 6-Me OCH _Two HOO C16.115 Et H 2-Cl, 6-Me OCH _Two HOS C16.116 nPr H 2-Cl, 6-Me OCH _Two HOS C16.117 iPr H 2-Cl, 6-Me OCH _Two HOS C16.118 nBu H 2-Cl, 6-Me OCH _Two HOS C16.119 FCH _Two H 2-Cl, 6-Me OCH _Two HOS C16.120 F _Two CH H 2-Cl, 6-Me OCH _Two HOS C16.121 F _Three CH 2-Cl, 6-Me OCH _Two HOS C16.122 ClCH _Two H 2-Cl, 6-Me OCH _Two HOS C16.123 Cl _Two CH H 2-Cl, 6-Me OCH _Two HOS C16.124 Me H 2-Me, 5-Cl OCH _Two HOS C16.125 Me H 2-Me, 5-Cl SCH _Two HOS C16.126 MeO H 2-Me, 5-Cl OCH _Two HOS 138-141 C16.127 MeO H 2-Me, 5-Cl OCH _Two HOO C16.128 Et H 2-Me, 5-Cl OCH _Two HOS C16.129 nPr H 2-Me, 5-Cl OCH _Two HOS C16.130 iPr H 2-Me, 5-Cl OCH _Two HOS C16.131 nBu H 2-Me, 5-Cl OCH _Two HOS C16.132 FCH _Two H 2-Me, 5-Cl OCH _Two HOS C16.133 F _Two CH H 2-Me, 5-Cl OCH _Two HOS C16.134 F _Three CH 2-Me, 5-Cl OCH _Two HOS C16.135 ClCH _Two H 2-Me, 5-Cl OCH _Two HOS C16.136 Cl _Two CH H 2-Me, 5-Cl OCH _Two HOS C17.1 Me H 2-F, 3-Cl OCH _Two HOS C17.2 Me H 2-F, 3-Cl SCH _Two HOS C17.3 Et H 2-F, 3-Cl OCH _Two HOS C17.4 nPr H 2-F, 3-Cl OCH _Two HOS C17.5 iPr H 2-F, 3-Cl OCH _Two HOS C17.6 nBu H 2-F, 3-Cl OCH _Two HOS C17.7 FCH _Two H 2-F, 3-Cl OCH _Two HOS C17.8 F _Two CH H 2-F, 3-Cl OCH _Two HOS C17.9 F _Three CH 2-F, 3-Cl OCH _Two HOS C17.10 ClCH _Two H 2-F, 3-Cl OCH _Two HOS C17.11 Cl _Two CH H 2-F, 3-Cl OCH _Two HOS C17.12 Me H 2-F, 5-Cl OCH _Two HOS C17.13 Me H 2-F, 5-Cl SCH _Two HOS C17.14 Et H 2-F, 5-Cl OCH _Two HOS C17.15 nPr H 2-F, 5-Cl OCH _Two HOS C17.16 iPr H 2-F, 5-Cl OCH _Two HOS C17.18 nBu H 2-F, 5-Cl OCH _Two HOS C17.19 FCH _Two H 2-F, 5-Cl OCH _Two HOS C17.20 F _Two CH H 2-F, 5-Cl OCH _Two HOS C17.21 F _Three CH 2-F, 5-Cl OCH _Two HOS C17.22 ClCH _Two H 2-F, 5-Cl OCH _Two HOS C17.23 Cl _Two CH H 2-F, 5-Cl OCH _Two HOS C17.24 Me H 3-Cl, 5-F OCH _Two HOS C17.25 Me H 3-Cl, 5-F SCH _Two HOS C17.26 Et H 3-Cl, 5-F OCH _Two HOS C17.27 nPr H 3-Cl, 5-F OCH _Two HOS C17.28 iPr H 3-Cl, 5-F OCH _Two HOS C17.29 nBu H 3-Cl, 5-F OCH _Two HOS C17.30 FCH _Two H 3-Cl, 5-F OCH _Two HOS C17.31 F _Two CH H 3-Cl, 5-F OCH _Two HOS C17.32 F _Three CH 3-Cl, 5-F OCH _Two HOS C17.33 ClCH _Two H 3-Cl, 5-F OCH _Two HOS C17.34 Cl _Two CH H 3-Cl, 5-F OCH _Two HOS C17.35 Me H 2-Cl, 3-F OCH _Two HOS C17.36 Me H 2-Cl, 3-F SCH _Two HOS C17.37 Et H 2-Cl, 3-F OCH _Two HOS C17.38 nPr H 2-Cl, 3-F OCH _Two HOS C17.39 iPr H 2-Cl, 3-F OCH _Two HOS C17.40 nBu H 2-Cl, 3-F OCH _Two HOS C17.41 FCH _Two H 2-Cl, 3-F OCH _Two HOS C17.42 F _Two CH H 2-Cl, 3-F OCH _Two HOS C17.43 F _Three CH 2-Cl, 3-F OCH _Two HOS C17.44 ClCH _Two H 2-Cl, 3-F OCH _Two HOS C17.45 Cl _Two CH H 2-Cl, 3-F OCH _Two HOS C17.46 Me H 2-Cl, 6-F OCH _Two HOS C17.47 Me H 2-Cl, 6-F SCH _Two HOS C17.48 Et H 2-Cl, 6-F OCH _Two HOS C17.49 nPr H 2-Cl, 6-F OCH _Two HOS C17.50 iPr H 2-Cl, 6-F OCH _Two HOS C17.51 nBu H 2-Cl, 6-F OCH _Two HOS C17.52 FCH _Two H 2-Cl, 6-F OCH _Two HOS C17.53 F _Two CH H 2-Cl, 6-F OCH _Two HOS C17.54 F _Three CH 2-Cl, 6-F OCH _Two HOS C17.55 ClCH _Two H 2-Cl, 6-F OCH _Two HOS C17.56 Cl _Two CH H 2-Cl, 6-F OCH _Two HOS C17.57 Me H 2-Cl, 5-F OCH _Two HOS C17.58 Me H 2-Cl, 5-F SCH _Two HOS C17.59 Et H 2-Cl, 5-F OCH _Two HOS C17.60 nPr H 2-Cl, 5-F OCH _Two HOS C17.61 iPr H 2-Cl, 5-F OCH _Two HOS C17.62 nBu H 2-Cl, 5-F OCH _Two HOS C17.63 FCH _Two H 2-Cl, 5-F OCH _Two HOS C17.64 F _Two CH H 2-Cl, 5-F OCH _Two HOS C17.65 F _Three CH 2-Cl, 5-F OCH _Two HOS C17.66 ClCH _Two H 2-Cl, 5-F OCH _Two HOS C17.67 Cl _Two CH H 2-Cl, 5-F OCH _Two HOS C17.68 Me H 2-CF _Three , 3-Me OCH _Two HOS C17.69 Me H 2-CF _Three , 3-Me SCH _Two HOS C17.70 Et H 2-CF _Three , 3-Me OCH _Two HOS C17.71 nPr H 2-CF _Three , 3-Me OCH _Two HOS C17.72 iPr H 2-CF _Three , 3-Me OCH _Two HOS C17.73 nBu H 2-CF _Three , 3-Me OCH _Two HOS C17.74 FCH _Two H 2-CF _Three , 3-Me OCH _Two HOS C17.75 F _Two CH H 2-CF _Three , 3-Me OCH _Two HOS C17.76 F _Three CH 2-CF _Three , 3-Me OCH _Two HOS C17.77 ClCH _Two H 2-CF _Three , 3-Me OCH _Two HOS C17.78 Cl _Two CH H 2-CF _Three , 3-Me OCH _Two HOS C17.79 Me H 2-CF _Three , 5-Me OCH _Two HOS C17.80 Me H 2-CF _Three , 5-Me SCH _Two HOS C17.81 Et H 2-CF _Three , 5-Me OCH _Two HOS C17.82 nPr H 2-CF _Three , 5-Me OCH _Two HOS C17.83 iPr H 2-CF _Three , 5-Me OCH _Two HOS C17.84 nBu H 2-CF _Three , 5-Me OCH _Two HOS C17.85 FCH _Two H 2-CF _Three , 5-Me OCH _Two HOS C17.86 F _Two CH H 2-CF _Three , 5-Me OCH _Two HOS C17.87 F _Three CH 2-CF _Three , 5-Me OCH _Two HOS C17.88 ClCH _Two H 2-CF _Three , 5-Me OCH _Two HOS C17.89 Cl _Two CH H 2-CF _Three , 5-Me OCH _Two HOS C17.90 Me H 3-CF _Three , 5-Me OCH _Two HOS C17.91 Me H 3-CF _Three , 5-Me SCH _Two HOS C17.92 Et H 3-CF _Three , 5-Me OCH _Two HOS C17.93 nPr H 3-CF _Three , 5-Me OCH _Two HOS C17.94 iPr H 3-CF _Three , 5-Me OCH _Two HOS C17.95 nBu H 3-CF _Three , 5-Me OCH _Two HOS C17.96 FCH _Two H 3-CF _Three , 5-Me OCH _Two HOS C17.97 F _Two CH H 3-CF _Three , 5-Me OCH _Two HOS C17.98 F _Three CH 3-CF _Three , 5-Me OCH _Two HOS C17.99 ClCH _Two H 3-CF _Three , 5-Me OCH _Two HOS C17.100 Cl _Two CH H 3-CF _Three , 5-Me OCH _Two HOS C17.101 Me H 2-Me, 3-CF _Three OCH _Two HOS C17.102 Me H 2-Me, 3-CF _Three SCH _Two HOS C17.103 Et H 2-Me, 3-CF _Three OCH _Two HOS C17.104 nPr H 2-Me, 3-CF _Three OCH _Two HOS C17.105 iPr H 2-Me, 3-CF _Three OCH _Two HOS C17.106 nBu H 2-Me, 3-CF _Three OCH _Two HOS C17.107 FCH _Two H 2-Me, 3-CF _Three OCH _Two HOS C17.108 F _Two CH H 2-Me, 3-CF _Three OCH _Two HOS C17.109 F _Three CH 2-Me, 3-CF _Three OCH _Two HOS C17.110 ClCH _Two H 2-Me, 3-CF _Three OCH _Two HOS C17.111 Cl _Two CH H 2-Me, 3-CF _Three OCH _Two HOS C17.112 Me H 2-CF _Three , 6-Me OCH _Two HOS C17.113 Me H 2-CF _Three , 6-Me SCH _Two HOS C17.114 Et H 2-CF _Three , 6-Me OCH _Two HOS C17.115 nPr H 2-CF _Three , 6-Me OCH _Two HOS C17.116 iPr H 2-CF _Three , 6-Me OCH _Two HOS C17.117 nBu H 2-CF _Three , 6-Me OCH _Two HOS C17.118 FCH _Two H 2-CF _Three , 6-Me OCH _Two HOS C17.119 F _Two CH H 2-CF _Three , 6-Me OCH _Two HOS C17.120 F _Three CH 2-CF _Three , 6-Me OCH _Two HOS C17.121 ClCH _Two H 2-CF _Three , 6-Me OCH _Two HOS C17.122 Cl _Two CH H 2-CF _Three , 6-Me OCH _Two HOS C17.123 Me H 2-Me, 5-CF _Three OCH _Two HOS C17.124 Me H 2-Me, 5-CF _Three SCH _Two HOS C17.125 Et H 2-Me, 5-CF _Three OCH _Two HOS C17.126 nPr H 2-Me, 5-CF _Three OCH _Two HOS C17.127 iPr H 2-Me, 5-CF _Three OCH _Two HOS C17.128 nBu H 2-Me, 5-CF _Three OCH _Two HOS C17.129 FCH _Two H 2-Me, 5-CF _Three OCH _Two HOS C17.130 F _Two CH H 2-Me, 5-CF _Three OCH _Two HOS C17.131 F _Three CH 2-Me, 5-CF _Three OCH _Two HOS C17.132 ClCH _Two H 2-Me, 5-CF _Three OCH _Two HOS C17.133 Cl _Two CH H 2-Me, 5-CF _Three OCH _Two HOS C18.1 Me H 2-OMe, 3-Me OCH _Two HOS C18.2 Me H 2-OMe, 3-Me SCH _Two HOS C18.3 Et H 2-OMe, 3-Me OCH _Two HOS C18.4 nPr H 2-OMe, 3-Me OCH _Two HOS C18.5 iPr H 2-OMe, 3-Me OCH _Two HOS C18.6 nBu H 2-OMe, 3-Me OCH _Two HOS C18.7 FCH _Two H 2-OMe, 3-Me OCH _Two HOS C18.8 F _Two CH H 2-OMe, 3-Me OCH _Two HOS C18.9 F _Three CH 2-OMe, 3-Me OCH _Two HOS C18.10 ClCH _Two H 2-OMe, 3-Me OCH _Two HOS C18.11 Cl _Two CH H 2-OMe, 3-Me OCH _Two HOS C18.12 Me H 2-OMe, 5-Me OCH _Two HOS C18.13 Me H 2-OMe, 5-Me SCH _Two HOS C18.14 Et H 2-OMe, 5-Me OCH _Two HOS C18.15 nPr H 2-OMe, 5-Me OCH _Two HOS C18.16 iPr H 2-OMe, 5-Me OCH _Two HOS C18.17 nBu H 2-OMe, 5-Me OCH _Two HOS C18.18 FCH _Two H 2-OMe, 5-Me OCH _Two HOS C18.19 F _Two CH H 2-OMe, 5-Me OCH _Two HOS C18.20 F _Three CH 2-OMe, 5-Me OCH _Two HOS C18.21 ClCH _Two H 2-OMe, 5-Me OCH _Two HOS C18.22 Cl _Two CH H 2-OMe, 5-Me OCH _Two HOS C18.23 Me H 3-OMe, 5-Me OCH _Two HOS C18.24 Me H 3-OMe, 5-Me SCH _Two HOS C18.25 Et H 3-OMe, 5-Me OCH _Two HOS C18.26 nPr H 3-OMe, 5-Me OCH _Two HOS C18.27 iPr H 3-OMe, 5-Me OCH _Two HOS C18.28 nBu H 3-OMe, 5-Me OCH _Two HOS C18.29 FCH _Two H 3-OMe, 5-Me OCH _Two HOS C18.30 F _Two CH H 3-OMe, 5-Me OCH _Two HOS C18.31 F _Three CH 3-OMe, 5-Me OCH _Two HOS C18.32 ClCH _Two H 3-OMe, 5-Me OCH _Two HOS C18.33 Cl _Two CH H 3-OMe, 5-Me OCH _Two HOS C18.35 Me H 2-Me, 3-OMe OCH _Two HOS C18.36 Me H 2-Me, 3-OMe SCH _Two HOS C18.37 Et H 2-Me, 3-OMe OCH _Two HOS C18.38 nPr H 2-Me, 3-OMe OCH _Two HOS C18.39 iPr H 2-Me, 3-OMe OCH _Two HOS C18.40 nBu H 2-Me, 3-OMe OCH _Two HOS C18.41 FCH _Two H 2-Me, 3-OMe OCH _Two HOS C18.42 F _Two CH H 2-Me, 3-OMe OCH _Two HOS C18.43 F _Three CH 2-Me, 3-OMe OCH _Two HOS C18.44 ClCH _Two H 2-Me, 3-OMe OCH _Two HOS C18.45 Cl _Two CH H 2-Me, 3-OMe OCH _Two HOS C18.46 Me H 2-OMe, 6-Me OCH _Two HOS C18.47 Me H 2-OMe, 6-Me SCH _Two HOS C18.48 Et H 2-OMe, 6-Me OCH _Two HOS C18.49 nPr H 2-OMe, 6-Me OCH _Two HOS C18.50 iPr H 2-OMe, 6-Me OCH _Two HOS C18.51 nBu H 2-OMe, 6-Me OCH _Two HOS C18.52 FCH _Two H 2-OMe, 6-Me OCH _Two HOS C18.53 F _Two CH H 2-OMe, 6-Me OCH _Two HOS C18.54 F _Three CH 2-OMe, 6-Me OCH _Two HOS C18.55 ClCH _Two H 2-OMe, 6-Me OCH _Two HOS C18.56 Cl _Two CH H 2-OMe, 6-Me OCH _Two HOS C18.57 Me H 2-Me, 5-OMe OCH _Two HOS C18.58 Me H 2-Me, 5-OMe SCH _Two HOS C18.59 Et H 2-Me, 5-OMe OCH _Two HOS C18.60 nPr H 2-Me, 5-OMe OCH _Two HOS C18.61 iPr H 2-Me, 5-OMe OCH _Two HOS C18.62 nBu H 2-Me, 5-OMe OCH _Two HOS C18.63 FCH _Two H 2-Me, 5-OMe OCH _Two HOS C18.64 F _Two CH H 2-Me, 5-OMe OCH _Two HOS C18.65 F _Three CH 2-Me, 5-OMe OCH _Two HOS C18.67 Cl _Two CH H 2-Me, 5-OMe OCH _Two HOS C18.68 Me H 2-iPr, 3-Me OCH _Two HOS C18.69 Et H 2-iPr, 3-Me OCH _Two HOS C18.70 nPr H 2-iPr, 3-Me OCH _Two HOS C18.71 iPr H 2-iPr, 3-Me OCH _Two HOS C18.72 nBu H 2-iPr, 3-Me OCH _Two HOS C18.73 FCH _Two H 2-iPr, 3-Me OCH _Two HOS C18.74 F _Two CH H 2-iPr, 3-Me OCH _Two HOS C18.75 F _Three CH 2-iPr, 3-Me OCH _Two HOS C18.76 ClCH _Two H 2-iPr, 3-Me OCH _Two HOS C18.77 Cl _Two CH H 2-iPr, 3-Me OCH _Two HOS C18.78 Me H 2-iPr, 5-Me OCH _Two HOS C18.79 Et H 2-iPr, 5-Me OCH _Two HOS C18.80 nPr H 2-iPr, 5-Me OCH _Two HOS C18.81 iPr H 2-iPr, 5-Me OCH _Two HOS C18.82 nBu H 2-iPr, 5-Me OCH _Two HOS C18.83 FCH _Two H 2-iPr, 5-Me OCH _Two HOS C18.84 F _Two CH H 2-iPr, 5-Me OCH _Two HOS C18.85 F _Three CH 2-iPr, 5-Me OCH _Two HOS C18.86 ClCH _Two H 2-iPr, 5-Me OCH _Two HOS C18.87 Cl _Two CH H 2-iPr, 5-Me OCH _Two HOS C18.88 Me H 3-Me, 5-iPr OCH _Two HOS C18.89 Et H 3-Me, 5-iPr OCH _Two HOS C18.90 nPr H 3-Me, 5-iPr OCH _Two HOS C18.91 iPr H 3-Me, 5-iPr OCH _Two HOS C18.92 nBu H 3-Me, 5-iPr OCH _Two HOS C18.93 FCH _Two H 3-Me, 5-iPr OCH _Two HOS C18.94 F _Two CH H 3-Me, 5-iPr OCH _Two HOS C18.96 ClCH _Two H 3-Me, 5-iPr OCH _Two HOS C18.97 Cl _Two CH H 3-Me, 5-iPr OCH _Two HOS C18.98 Me H 2-Me, 3-iPr OCH _Two HOS C18.99 Et H 2-Me, 3-iPr OCH _Two HOS C18.100 nPr H 2-Me, 3-iPr OCH _Two HOS C18.101 iPr H 2-Me, 3-iPr OCH _Two HOS C18.102 nBu H 2-Me, 3-iPr OCH _Two HOS C18.103 FCH _Two H 2-Me, 3-iPr OCH _Two HOS C18.104 F _Two CH H 2-Me, 3-iPr OCH _Two HOS C18.105 F _Three CH 2-Me, 3-iPr OCH _Two HOS C18.106 ClCH _Two H 2-Me, 3-iPr OCH _Two HOS C18.107 Cl _Two CH H 2-Me, 3-iPr OCH _Two HOS C18.108 Me H 2-Me, 6-iPr OCH _Two HOS C18.109 Et H 2-Me, 6-iPr OCH _Two HOS C18.110 nPr H 2-Me, 6-iPr OCH _Two HOS C18.111 iPr H 2-Me, 6-iPr OCH _Two HOS C18.112 nBu H 2-Me, 6-iPr OCH _Two HOS C18.113 FCH _Two H 2-Me, 6-iPr OCH _Two HOS C18.114 F _Two CH H 2-Me, 6-iPr OCH _Two HOS C18.115 F _Three CH 2-Me, 6-iPr OCH _Two HOS C18.116 ClCH _Two H 2-Me, 6-iPr OCH _Two HOS C18.117 Cl _Two CH H 2-Me, 6-iPr OCH _Two HOS C18.118 Me H 2-Me, 5-iPr OCH _Two HOS 153-156 C18.119 MeO H 2-Me, 5-iPr OCH _Two HOS 115-117 C18.120 MeO H 2-Me, 5-iPr OCH _Two HOO C18.121 Et H 2-Me, 5-iPr OCH _Two HOS C18.122 nPr H 2-Me, 5-iPr OCH _Two HOS C18.123 iPr H 2-Me, 5-iPr OCH _Two HOS C18.124 nBu H 2-Me, 5-iPr OCH _Two HOS C18.125 FCH _Two H 2-Me, 5-iPr OCH _Two HOS C18.126 F _Two CH H 2-Me, 5-iPr OCH _Two HOS C18.127 F _Three CH 2-Me, 5-iPr OCH _Two HOS C18.128 ClCH _Two H 2-Me, 5-iPr OCH _Two HOS C18.129 Cl _Two CH H 2-Me, 5-iPr OCH _Two HOS C18.130 Me H 2-Cl, 6-CO _Two Me OCH _Two HOS 141-143 C18.131 MeO H 2-Cl, 6-CO _Two Me OCH _Two HOS ────────────────────────────────────

【００５４】[0054]

【表４】 ──────────────────────────────────── 番号 R¹ R² (R³)n (R⁶)m Q 融点( ℃） ACR⁴(R⁵) X ──────────────────────────────────── D1.1 Me Me 2-Me OCH₂ H O S 108-109 D1.2 MeO Me 2-Me OCH₂ H O S 88-91 D1.3 Me Me 2-Me OCH₂ H O O D1.4 MeO Me 2-Me OCH₂ H O O 油状物 D1.5 Me Et 2-Me OCH₂ H O S アモルファス D1.6 MeO Et 2-Me OCH₂ H O S D1.7 Me Et 2-Me OCH₂ H O O D1.8 MeO Et 2-Me OCH₂ H O O 油状物 D1.9 Me iPr 2-Me OCH₂ H O S D1.10 MeO iPr 2-Me OCH₂ H O S 98-100 D1.11 MeO CH₂O(1,3-Me₂-4-Pyra) 2-Me OCH₂ H O O D1.12 MeO iPr 2-Me OCH₂ H O O D1.13 Me CH₂CH=CH₂ 2-Me OCH₂ H O S 油状物 D1.14 MeO CH₂CH=CH₂ 2-Me OCH₂ H O S 油状物 D1.15 MeO CH₂O(3,5-Me₂-4-Isox) 2-Me OCH₂ H O O D1.16 MeO CH₂CH=CH₂ 2-Me OCH₂ H O O 油状物 D1.17 MeO CH₂OCO(Pyrim-2-yl) 2-Me OCH₂ H O S D1.18 MeO CH₂C≡CH 2-Me OCH₂ H O S 油状物 D1.19 MeO CH₂C≡CH 2-Me OCH₂ H O O D1.20 MeO CH₂CH=CHCl 2-Me OCH₂ H O S D1.21 MeO CH₂OCO(6-Cl-Pyrd-3-yl) 2-Me OCH₂ H O S D1.22 MeO CH₂O(THP-2-yl) 2-Me OCH₂ H O S D1.23 MeO CH₂O(THP-2-yl) 2-Me OCH₂ H O O D1.24 MeO CH₂O(1-Me-Pyrr-2-yl) 2-Me OCH₂ H O S D1.25 MeO nPr 2-Me OCH₂ H O S D1.26 Me nPr 2-Me OCH₂ H O O D1.27 MeO nPr 2-Me OCH₂ H O O D1.28 Me CH₂COMe 2-Me OCH₂ H O S D1.29 MeO CH₂COMe 2-Me OCH₂ H O S D1.30 MeO CH₂OCO(Qui-3-yl) 2-Me OCH₂ H O O D1.31 MeO CH₂COMe 2-Me OCH₂ H O O D1.32 MeO CH₂COtBu 2-Me OCH₂ H O O D1.34 Me CH₂COtBu 2-Me OCH₂ H O O D1.35 MeO CH₂COtBu 2-Me OCH₂ H O S 油状物 D1.36 Me CH₂COPh 2-Me OCH₂ H O S D1.37 MeO CH₂COPh 2-Me OCH₂ H O S アモルファス D1.38 Me CH₂COPh 2-Me OCH₂ H O O D1.39 MeO CH₂COPh 2-Me OCH₂ H O O D1.40 MeO CH₂CO(4-Cl-Ph) 2-Me OCH₂ H O S 油状物 D1.41 MeO CH₂CO(4-Cl-Ph) 2-Me OCH₂ H O O D1.42 Me CH₂COOEt 2-Me OCH₂ H O S D1.43 MeO CH₂COOEt 2-Me OCH₂ H O S 油状物 D1.44 Me CH₂COOEt 2-Me OCH₂ H O O D1.45 MeO CH₂COOEt 2-Me OCH₂ H O O D1.46 MeO CH(Me)COOEt 2-Me OCH₂ H O S 油状物 D1.47 MeO CH₂OH 2-Me OCH₂ H O S 121-123 D1.48 MeO CH₂OH 2-Me SCH₂ H O S D1.49 MeO CH₂OH 2-Me OCH₂ H O O 132-133 D1.50 Me CH₂OMe 2-Me OCH₂ H O S 油状物 D1.51 MeO CH₂OMe 2-Me OCH₂ H O S 76-78 D1.52 Me CH₂OMe 2-Me OCH₂ H O O D1.53 MeO CH₂OMe 2-Me OCH₂ H O O D1.54 Me CH₂OEt 2-Me OCH₂ H O S D1.55 MeO CH₂OEt 2-Me OCH₂ H O S アモルファス D1.56 MeO CH₂OiBu 2-Me OCH₂ H O S 油状物 D1.57 MeO CH₂OnBu 2-Me OCH₂ H O S 油状物 D1.58 MeO CH₂OnBu 2-Me OCH₂ H O O D1.59 MeO CH₂OnBu 2-Me SCH₂ H O S D1.60 MeO CH₂OCH₂CH=CHCH₃ 2-Me OCH₂ H O S 油状物 D1.61 Me CH₂SMe 2-Me OCH₂ H O S D1.62 MeO CH₂SMe 2-Me OCH₂ H O S 87-88 D1.63 Me CH₂SMe 2-Me OCH₂ H O O D1.64 MeO CH₂SMe 2-Me OCH₂ H O O D1.65 MeO CH₂S(4-Cl-Ph) 2-Me OCH₂ H O S 油状物 D1.66 MeO CH₂S(4-Cl-Ph) 2-Me OCH₂ H O O D1.67 MeO CH₂OCH₂Ph 2-Me OCH₂ H O S 油状物 D1.68 MeO CH₂OCOMe 2-Me OCH₂ H O S 油状物 D1.69 MeO CH₂OCOMe 2-Me OCH₂ H O O 油状物 D1.70 MeO CH₂OCOEt 2-Me OCH₂ H O S 油状物 D1.71 MeO CH₂OCOEt 2-Me OCH₂ H O O 油状物 D1.72 MeO CH₂OCOnPr 2-Me OCH₂ H O S 油状物 D1.73 MeO CH₂OCOnPr 2-Me OCH₂ H O O D1.74 MeO CH₂OCOiPr 2-Me OCH₂ H O S 油状物 D1.75 MeO CH₂OCOiPr 2-Me OCH₂ H O O D1.76 MeO CH₂OCOnBu 2-Me OCH₂ H O S 油状物 D1.77 MeO CH₂OCOnBu 2-Me OCH₂ H O O D1.78 MeO CH₂OCOtBu 2-Me OCH₂ H O S 油状物 D1.79 MeO CH₂OCO(c-Pen) 2-Me OCH₂ H O S 油状物 D1.80 MeO CH₂OCO(c_-Hex) 2-Me OCH₂ H O S 油状物 D1.81 MeO CH₂OCOCH₂OMe 2-Me OCH₂ H O S 油状物 D1.82 MeO CH₂OCOCH₂OMe 2-Me OCH₂ H O O 油状物 D1.83 MeO CH₂OCO(CH₂)₂OMe 2-Me OCH₂ H O S 油状物 D1.84 MeO CH₂OCO(CH₂)₂OMe 2-Me OCH₂ H O O D1.85 MeO CH₂OCOCH₂CH₂OEt 2-Me OCH₂ H O S 油状物 D1.86 MeO CH₂OCOCH₂CH₂Et 2-Me OCH₂ H O O D1.87 MeO CH₂OCOCH₂C(Me)=CH₂ 2-Me OCH₂ H O S 油状物 D1.88 MeO CH₂OCOCH₂Cl 2-Me OCH₂ H O S 油状物 D1.89 MeO CH₂OCOCH₂Cl 2-Me OCH₂ H O O D1.90 MeO CH₂OCOPh 2-Me OCH₂ H O S アモルファス D1.91 MeO CH₂OCOPh 2-Me OCH₂ H O O アモルファス D1.92 MeO CH₂OCO(4-Cl-Ph) 2-Me OCH₂ H O S 油状物 D1.93 MeO CH₂OCO(4-Me-Ph) 2-Me OCH₂ H O S 油状物 D1.94 MeO CH₂OCO(4-MeO-Ph) 2-Me OCH₂ H O S アモルファス D1.95 MeO CH₂OCOCH₂Ph 2-Me OCH₂ H O S 油状物 D1.96 MeO CH₂OCOCH₂Ph 2-Me OCH₂ H O O D1.97 MeO CH₂O(2-Then) 2-Me OCH₂ H O S 粘土状 D1.98 MeO CH₂O(2-Then) 2-Me OCH₂ H O O アモルファス D1.99 MeO CH₂O(2-Furo) 2-Me OCH₂ H O S 粘土状 D1.100 MeO CH₂O(Nico) 2-Me OCH₂ H O S 油状物 D1.101 MeO CH₂O(2-Cl-Nico) 2-Me OCH₂ H O S 油状物 D1.102 MeO CH₂OCO(Pyra) 2-Me OCH₂ H O S 油状物 D1.103 MeO CH₂OCOOMe 2-Me OCH₂ H O S 油状物 D1.104 MeO CH₂OCOOMe 2-Me OCH₂ H O O 油状物 D1.105 Me CH₂CH₂OH 2-Me OCH₂ H O S 97-99 D1.106 MeO CH₂CH₂OH 2-Me OCH₂ H O S 109-110 D1.107 Me CH₂CH₂OH 2-Me OCH₂ H O O D1.108 MeO CH₂CH₂OH 2-Me OCH₂ H O O D1.109 Me CH₂CH₂OEt 2-Me OCH₂ H O S 油状物 D1.110 MeO CH₂CH₂OEt 2-Me OCH₂ H O S 油状物 D1.111 MeO CH₂CH₂OEt 2-Me OCH₂ H O O D1.112 MeO CH₂CH₂OCH=CH₂ 2-Me OCH₂ H O S 油状物 D1.113 MeO CH₂CH₂OnPr 2-Me OCH₂ H O S 油状物 D1.114 MeO CH₂CH₂SMe 2-Me OCH₂ H O S 119-120 D1.115 MeO CH₂CH₂SMe 2-Me OCH₂ H O O D1.116 MeO CH₂CH₂SEt 2-Me OCH₂ H O S 油状物 D1.117 MeO CH₂CH₂OPh 2-Me OCH₂ H O S 油状物 D1.118 Me CH₂CH₂O(THP-2-yl) 2-Me OCH₂ H O S 油状物 D1.119 MeO CH₂CH₂O(THP-2-yl) 2-Me OCH₂ H O S 油状物 D1.120 Me CH₂CH₂O(THP-2-yl) 2-Me OCH₂ H O O D1.121 MeO CH₂CH₂O(THP-2-yl) 2-Me OCH₂ H O O D1.122 Me CH₂CH₂OCOMe 2-Me OCH₂ H O S 油状物 D1.123 MeO CH₂CH₂OCOMe 2-Me OCH₂ H O S 油状物 D1.124 MeO CH₂CH₂OCOMe 2-Me OCH₂ H O O D1.125 Me CH₂CH₂OCOEt 2-Me OCH₂ H O S 油状物 D1.126 MeO CH₂CH₂OCOEt 2-Me OCH₂ H O S 油状物 D1.127 MeO CH₂CH₂OCOEt 2-Me OCH₂ H O O D1.128 Me CH₂CH₂OCO(c-Bu) 2-Me OCH₂ H O S 油状物 D1.129 Me CH₂CH₂OCOCH₂Cl 2-Me OCH₂ H O S 油状物 D1.130 Me CH₂CH₂OCOCH₂OMe 2-Me OCH₂ H O S 油状物 D1.131 Me CH₂CH₂OCOPh 2-Me OCH₂ H O S 油状物 D1.132 MeO CH₂CH₂OCOPh 2-Me OCH₂ H O S 油状物 D1.133 Me CH₂CH₂OCOPh 2-Me OCH₂ H O O D1.134 MeO CH₂CH₂OCOPh 2-Me OCH₂ H O O D1.135 Me CH₂CH₂O(2-Furo) 2-Me OCH₂ H O S 油状物 D1.136 Me CH₂CH₂O(Isonico) 2-Me OCH₂ H O S 油状物 D1.137 MeO CH₂CH₂O(Isonico) 2-Me OCH₂ H O S D1.138 MeO CH₂CH₂O(Nico) 2-Me OCH₂ H O S D1.139 MeO CH₂CH₂O(Nico) 2-Me OCH₂ H O O D2.1 Me COMe 2-Me OCH₂ H O S 119-121 D2.2 Me COMe 2-Me OCH₂ H O O D2.3 Me COEt 2-Me OCH₂ H O S D2.4 MeO COEt 2-Me OCH₂ H O S 油状物 D2.5 MeO COEt 2-Me OCH₂ H O O 油状物 D2.6 Me COnPr 2-Me OCH₂ H O S 油状物 D2.7 MeO COnPr 2-Me OCH₂ H O S 油状物 D2.8 Me COnPr 2-Me OCH₂ H O O D2.9 MeO COnPr 2-Me OCH₂ H O O 油状物 D2.10 MeO COiPr 2-Me OCH₂ H O S 90-92 D2.11 MeO COnBu 2-Me OCH₂ H O S 油状物 D2.12 MeO COnBu 2-Me OCH₂ H O O D2.13 MeO COiBu 2-Me OCH₂ H O S 78-80 D2.14 MeO CO(c-Bu) 2-Me OCH₂ H O S 76-78 D2.15 MeO CO(c-pen) 2-Me OCH₂ H O S 油状物 D2.16 Me CO(c-Hex) 2-Me OCH₂ H O S D2.17 MeO CO(c-Hex) 2-Me OCH₂ H O S 油状物 D2.18 MeO CO(c-Hex) 2-Me OCH₂ H O O D2.19 EtO COEt 2-Me OCH₂ H O S 油状物 D2.20 MeO COCH₂OEt 2-Me OCH₂ H O S アモルファス D2.21 MeO COCH=CHMe 2-Me OCH₂ H O S 油状物 D2.22 MeO COCH=C(Me)Me 2-Me OCH₂ H O S 油状物 D2.23 EtO COCH₂OMe 2-Me OCH₂ H O S 油状物 D2.24 EtO COCH₂OEt 2-Me OCH₂ H O S D2.25 Me COCH₂OMe 2-Me OCH₂ H O S 油状物 D2.26 MeO COCH₂OMe 2-Me OCH₂ H O S 70-73 D2.27 Me COCH₂OMe 2-Me OCH₂ H O O D2.28 MeO COCH₂OMe 2-Me OCH₂ H O O 油状物 D2.29 Me COCH₂CH₂OMe 2-Me OCH₂ H O S 油状物 D2.30 MeO COCH₂CH₂OMe 2-Me OCH₂ H O S 油状物 D2.31 MeO COCH₂CH₂OMe 2-Me OCH₂ H O O D2.32 MeO COCH₂CH₂OEt 2-Me OCH₂ H O S 油状物 D2.33 MeO COCH₂CH₂OEt 2-Me OCH₂ H O O D2.34 Me COCH₂CH₂OEt 2-Me OCH₂ H O S D2.35 Me COCH₂CH₂OEt 2-Me OCH₂ H O O D2.36 Me COCH₂CH₂OnPr 2-Me OCH₂ H O S D2.37 MeO COCH₂CH₂OnPr 2-Me OCH₂ H O S D2.38 Me COCH₂CH₂OnPr 2-Me OCH₂ H O O D2.39 MeO COCH₂CH₂OnPr 2-Me OCH₂ H O O D2.40 MeO COCH(Cl)Me 2-Me OCH₂ H O S 油状物 D2.41 Me COPh 2-Me OCH₂ H O S 111-113 D2.42 MeO COPh 2-Me OCH₂ H O S 112-114 D2.43 Me COPh 2-Me OCH₂ H O O D2.44 MeO COPh 2-Me OCH₂ H O O 油状物 D2.45 MeO CO(4-tBu-Ph) 2-Me OCH₂ H O S 130-131.5 D2.46 MeO CO(2-Cl-Ph) 2-Me OCH₂ H O S 136-137 D2.47 MeO CO(3-Cl-Ph) 2-Me OCH₂ H O S 108.5-110.5 D2.48 MeO CO(4-Cl-Ph) 2-Me OCH₂ H O S アモルファス D2.49 MeO CO(4-Cl-Ph) 2-Me OCH₂ H O O D2.50 MeO CO(2,6-Cl₂-Ph) 2-Me OCH₂ H O S 191-193 D2.51 MeO CO(3,4-Cl₂-Ph) 2-Me OCH₂ H O S アモルファス D2.52 MeO CO(2,4-F₂-Ph) 2-Me OCH₂ H O S 137-139 D2.53 MeO CO(2,6-F₂-Ph) 2-Me OCH₂ H O S 151-152.5 D2.54 MeO CO(2-MeO-Ph) 2-Me OCH₂ H O S 126-128 D2.55 MeO CO(2-MeO-Ph) 2-Me OCH₂ H O O アモルファス D2.56 MeO CO(3-MeO-Ph) 2-Me OCH₂ H O S アモルファス D2.57 MeO CO(4-MeO-Ph) 2-Me OCH₂ H O S 126-128 D2.58 MeO CO(4-MeO-Ph) 2-Me OCH₂ H O O D2.59 MeO CO(3,4,5-(MeO)₃-Ph) 2-Me OCH₂ H O S D2.60 MeO CO(2-Me-Ph) 2-Me OCH₂ H O S 油状物 D2.61 MeO CO(4-Me-Ph) 2-Me OCH₂ H O S 132-133 D2.62 MeO CO(4-Me-Ph) 2-Me OCH₂ H O O D2.63 Me 2-Furo 2-Me OCH₂ H O S 油状物 D2.64 MeO 2-Furo 2-Me OCH₂ H O S D2.65 MeO 2-Furo 2-Me OCH₂ H O O 油状物 D2.66 MeO 2-Then 2-Me OCH₂ H O S 粘土状 D2.67 Me 2-Then 2-Me OCH₂ H O S 油状物 D2.68 MeO Nico 2-Me OCH₂ H O S 104 D2.69 MeO Nico 2-Me OCH₂ H O O D2.70 MeO CO(2,4-Me₂-1,2,3-Tria-5-yl) 2-Me OCH₂ H O S D2.71 MeO CO(Isothi-4-yl) 2-Me OCH₂ H O S D2.72 MeO CO(3-Cl-Benthi-2-yl) 2-Me OCH₂ H O S 155-157 D2.73 MeO COOMe 2-Me OCH₂ H O S 163-166 D2.74 MeO COOMe 2-Me OCH₂ H O O 141-144 D2.75 MeO COOEt 2-Me OCH₂ H O S 84-86 D2.76 MeO COOEt 2-Me OCH₂ H O O 油状物 D2.77 MeO COOnPr 2-Me OCH₂ H O S 油状物 D2.78 MeO COOnPr 2-Me OCH₂ H O O 油状物 D2.79 MeO COOiPr 2-Me OCH₂ H O S 油状物 D2.80 MeO COOnBu 2-Me OCH₂ H O S 油状物 D2.81 MeO COOnBu 2-Me OCH₂ H O O 油状物 D2.82 MeO COOiBu 2-Me OCH₂ H O S 油状物 D2.83 MeO COOCH₂CCl₃ 2-Me OCH₂ H O S 油状物 D2.84 MeO COOCH₂CCl₃ 2-Me OCH₂ H O O 102-105 D2.85 MeO COOPh 2-Me OCH₂ H O S 油状物 ────────────────────────────────────[Table 4] No. R ¹ R ² (R ³ ) n (R ⁶ ) m Q Melting point (° C) ACR ⁴ (R ⁵ ) X ───────────────────────────────── ─── D1.1 Me Me 2-Me OCH ₂ HOS 108-109 D1.2 MeO Me 2-Me OCH ₂ HOS 88-91 D1.3 Me Me 2-Me OCH ₂ HOO D1.4 MeO Me 2-Me OCH ₂ HOO Oil D1.5 Me Et 2-Me OCH ₂ HOS Amorphous D1.6 MeO Et 2-Me OCH ₂ HOS D1.7 Me Et 2-Me OCH ₂ HOO D1.8 MeO Et 2-Me OCH ₂ HOO Oil D1.9 Me iPr 2-Me OCH ₂ HOS D1.10 MeO iPr 2-Me OCH ₂ HOS 98-100 D1.11 MeO CH ₂ O (1,3-Me ₂ -4-Pyra) 2-Me OCH ₂ HOO D1.12 MeO iPr 2-Me OCH ₂ HOO D1.13 Me CH ₂ CH = CH ₂ 2-Me OCH ₂ HOS oil D1.14 MeO CH ₂ CH = CH ₂ 2-Me OCH ₂ HOS oil D1 .15 MeO CH ₂ O (3,5-Me ₂ -4-Isox) 2-Me OCH ₂ HOO D1.16 MeO CH ₂ CH = CH ₂ 2-Me OCH ₂ HOO Oil D1.17 MeO CH ₂ OCO ( Pyrim-2-yl) 2- Me OCH 2 HOS D1.18 MeO CH 2 C≡CH 2-Me OCH 2 HOS oil D1.19 MeO CH ₂ C≡CH 2-Me OCH ₂ HOO D1.20 MeO CH ₂ CH = CHCl 2-Me OCH ₂ HOS D1.21 MeO CH ₂ OCO (6-Cl-Pyrd-3-yl) 2-Me OCH ₂ HOS D1 .22 MeO CH ₂ O (THP-2-yl) 2-Me OCH ₂ HOS D1.23 MeO CH ₂ O (THP-2-yl) 2-Me OCH ₂ HOO D1.24 MeO CH ₂ O (1-Me -Pyrr-2-yl) 2-Me OCH ₂ HOS D1.25 MeO nPr 2-Me OCH ₂ HOS D1.26 Me nPr 2-Me OCH ₂ HOO D1.27 MeO nPr 2-Me OCH ₂ HOO D1.28 Me CH ₂ COMe 2-Me OCH ₂ HOS D1.29 MeO CH ₂ COMe 2-Me OCH ₂ HOS D1.30 MeO CH ₂ OCO (Qui-3-yl) 2-Me OCH ₂ HOO D1.31 MeO CH ₂ COMe 2 -Me OCH ₂ HOO D1.32 MeO CH ₂ COtBu 2-Me OCH ₂ HOO D1.34 Me CH ₂ COtBu 2-Me OCH ₂ HOO D1.35 MeO CH ₂ COtBu 2-Me OCH ₂ HOS Oil D1.36 Me CH ₂ COPh 2-Me OCH ₂ HOS D1.37 MeO CH ₂ COPh 2-Me OCH ₂ HOS amorphous D1.38 Me CH ₂ COPh 2-Me OCH ₂ HOO D1.39 MeO CH ₂ COPh 2-Me OCH ₂ HOO D1 .40 MeO CH ₂ CO (4-Cl-Ph) 2-Me OCH ₂ HOS oil D1.41 MeO CH ₂ CO (4-Cl-Ph) 2-Me OCH ₂ HOO D1.42 Me CH ₂ COOEt 2- Me OCH ₂ HOS D1.43 MeO CH ₂ COOEt 2-Me OCH ₂ HOS oil D1.44 Me CH ₂ COOEt 2-Me OCH ₂ HOO D1.45 MeO CH ₂ COOEt 2-Me OCH ₂ HOO D1 .46 MeO CH (Me) COOEt 2-Me OCH ₂ HOS oil D1.47 MeO CH ₂ OH 2-Me OCH ₂ HOS 121-123 D1.48 MeO CH ₂ OH 2-Me SCH ₂ HOS D1.49 MeO CH ₂ OH 2-Me OCH ₂ HOO 132-133 D1.50 Me CH ₂ OMe 2-Me OCH ₂ HOS Oil D1.51 MeO CH ₂ OMe 2-Me OCH ₂ HOS 76-78 D1.52 Me CH ₂ OMe 2 -Me OCH ₂ HOO D1.53 MeO CH ₂ OMe 2-Me OCH ₂ HOO D1.54 Me CH ₂ OEt 2-Me OCH ₂ HOS D1.55 MeO CH ₂ OEt 2-Me OCH ₂ HOS Amorphous D1.56 MeO CH ₂ OiBu 2-Me OCH ₂ HOS oil D1.57 MeO CH ₂ OnBu 2-Me OCH ₂ HOS oil D1.58 MeO CH ₂ OnBu 2-Me OCH ₂ HOO D1.59 MeO CH ₂ OnBu 2-Me SCH ₂ HOS D1.60 MeO CH ₂ OCH ₂ CH = CHCH ₃ 2-Me OCH ₂ HOS Oil D1.61 Me CH ₂ SMe 2-Me OCH ₂ HOS D1.62 MeO CH ₂ SMe 2-Me OCH ₂ HOS 87-88 D1.63 Me CH ₂ SMe 2-Me OCH ₂ HOO D1.64 MeO CH ₂ SMe 2-Me OCH ₂ HOO D1.65 MeO CH ₂ S (4-Cl-Ph) 2-Me OCH ₂ HOS Oil D1. 66 MeO CH ₂ S (4-Cl-Ph) 2-Me OCH ₂ HOO D1.67 MeO CH ₂ OCH ₂ Ph 2-Me OCH ₂ HOS oil D1.68 MeO CH ₂ OCOMe 2-Me OCH ₂ HOS oil D1.69 MeO CH ₂ OCOMe 2-Me OCH ₂ HOO Oil D1.70 MeO CH ₂ OCOEt 2-Me OCH ₂ HOS oil D1.71 MeO CH ₂ OCOEt 2-Me OCH ₂ HOO oil D1.72 MeO CH ₂ OCOnPr 2-Me OCH ₂ HOS oil D1.73 MeO CH ₂ OCOnPr 2-Me OCH ₂ HOO D1.74 MeO CH ₂ OCOiPr 2-Me OCH ₂ HOS oil D1.75 MeO CH ₂ OCOiPr 2-Me OCH ₂ HOO D1.76 MeO CH ₂ OCOnBu 2-Me OCH ₂ HOS oil D1.77 MeO CH ₂ OCOnBu 2-Me OCH ₂ HOO D1.78 MeO CH ₂ OCOtBu 2-Me OCH ₂ HOS oil D1.79 MeO CH ₂ OCO (c-Pen) 2-Me OCH ₂ HOS oil D1.80 MeO CH ₂ OCO (c _- Hex) 2-Me OCH ₂ HOS oil D1.81 MeO CH ₂ OCOCH ₂ OMe 2-Me OCH ₂ HOS oil D1.82 MeO CH ₂ OCOCH ₂ OMe 2-Me OCH ₂ HOO oil D1.83 MeO CH ₂ OCO (CH ₂ ) ₂ OMe 2-Me OCH ₂ HOS Oil D1.84 MeO CH ₂ OCO (CH ₂ ) ₂ OMe 2-Me OCH ₂ HOO D1.85 MeO CH ₂ OCOCH ₂ CH ₂ OEt 2- Me OCH ₂ HOS oil D1.86 MeO CH ₂ OCOCH ₂ CH ₂ Et 2-Me OCH ₂ HOO D1.87 MeO CH ₂ OCOCH ₂ C (Me) = CH ₂ 2-Me OCH ₂ HOS oil D1.88 MeO CH ₂ OCOCH ₂ Cl 2-Me OCH ₂ HOS Oil D1.89 MeO CH ₂ OCOCH ₂ Cl 2-Me OCH ₂ HOO D1.90 MeO CH ₂ OCOPh 2-Me OCH ₂ HOS Amorphous D1. 91 MeO CH ₂ OCOPh 2-Me OCH ₂ HOO Amorphous D1.92 MeO CH ₂ OCO (4-Cl-Ph) 2-Me OCH ₂ HOS oil D1.93 MeO CH ₂ OCO (4-Me-Ph) 2- Me OCH ₂ HOS oil D1.94 MeO CH ₂ OCO (4-MeO-Ph) 2-Me OCH ₂ HOS amorphous D1.95 MeO CH ₂ OCOCH ₂ Ph 2-Me OCH ₂ HOS oil D1.96 MeO CH ₂ OCOCH ₂ Ph 2-Me OCH ₂ HOO D1.97 MeO CH ₂ O (2-Then) 2-Me OCH ₂ HOS Clay D1.98 MeO CH ₂ O (2-Then) 2-Me OCH ₂ HOO Amorphous D1. 99 MeO CH ₂ O (2-Furo) 2-Me OCH ₂ HOS Clay D1.100 MeO CH ₂ O (Nico) 2-Me OCH ₂ HOS oil D1.101 MeO CH ₂ O (2-Cl-Nico) 2-Me OCH ₂ HOS oil D1.102 MeO CH ₂ OCO (Pyra) 2-Me OCH ₂ HOS oil D1.103 MeO CH ₂ OCOOMe 2-Me OCH ₂ HOS oil D1.104 MeO CH ₂ OCOOMe 2- Me OCH ₂ HOO Oil D1.105 Me CH ₂ CH ₂ OH 2-Me OCH ₂ HOS 97-99 D1.106 MeO CH ₂ CH ₂ OH 2-Me OCH ₂ HOS 109-110 D1.107 Me CH ₂ CH ₂ OH 2-Me OCH ₂ HOO D1.108 MeO CH ₂ CH ₂ OH 2-Me OCH ₂ HOO D1.109 Me CH ₂ CH ₂ OEt 2-Me OCH ₂ HOS Oil D1.110 MeO CH ₂ CH ₂ OEt 2- Me OCH ₂ HOS Oil D1.111 MeO CH ₂ CH ₂ OEt 2-Me OCH ₂ HOO D1.112 MeO CH ₂ CH ₂ OCH = CH ₂ 2-Me OCH ₂ HOS oil D1.113 MeO CH ₂ CH ₂ OnPr 2-Me OCH ₂ HOS oil D1. 114 MeO CH ₂ CH ₂ SMe 2-Me OCH ₂ HOS 119-120 D1.115 MeO CH ₂ CH ₂ SMe 2-Me OCH ₂ HOO D1.116 MeO CH ₂ CH ₂ SEt 2-Me OCH ₂ HOS oil D1. 117 MeO CH ₂ CH ₂ OPh 2-Me OCH ₂ HOS oil D1.118 Me CH ₂ CH ₂ O (THP-2-yl) 2-Me OCH ₂ HOS oil D1.119 MeO CH ₂ CH ₂ O (THP -2-yl) 2-Me OCH ₂ HOS oil D1.120 Me CH ₂ CH ₂ O (THP-2-yl) 2-Me OCH ₂ HOO D1.121 MeO CH ₂ CH ₂ O (THP-2-yl ) 2-Me OCH ₂ HOO D1.122 Me CH ₂ CH ₂ OCOMe 2-Me OCH ₂ HOS oil D1.123 MeO CH ₂ CH ₂ OCOMe 2-Me OCH ₂ HOS oil D1.124 MeO CH ₂ CH ₂ OCOMe 2-Me OCH ₂ HOO D1.125 Me CH ₂ CH ₂ OCOEt 2-Me OCH ₂ HOS oil D1.126 MeO CH ₂ CH ₂ OCOEt 2-Me OCH ₂ HOS oil D1.127 MeO CH ₂ CH ₂ OCOEt 2 -Me OCH ₂ HOO D1.128 Me CH ₂ CH ₂ OCO (c-Bu) 2-Me OCH ₂ HOS oil D1.129 Me CH ₂ CH ₂ OCOCH ₂ Cl 2-Me OCH ₂ HOS oil D1.130 Me CH ₂ CH ₂ OCOCH ₂ OMe 2-Me OCH ₂ HOS oil D1.131 Me CH ₂ CH ₂ OCOPh 2-Me OCH ₂ HOS oil D1.132 MeO CH ₂ CH ₂ OCOPh 2-Me OCH ₂ HOS oil D1.133 Me CH ₂ CH ₂ OCOPh 2-Me OCH ₂ HOO D1.134 MeO CH ₂ CH ₂ OCOPh 2-Me OCH ₂ HOO D1.135 Me CH ₂ CH ₂ O (2-Furo) 2-Me OCH ₂ HOS Oil D1.136 Me CH ₂ CH ₂ O (Isonico) 2-Me OCH ₂ HOS Oil D1.137 MeO CH ₂ CH ₂ O (Isonico) 2-Me OCH ₂ HOS D1.138 MeO CH ₂ CH ₂ O (Nico) 2-Me OCH ₂ HOS D1.139 MeO CH ₂ CH ₂ O (Nico) 2-Me OCH ₂ HOO D2.1 Me COMe 2-Me OCH ₂ HOS 119-121 D2.2 Me COMe 2-Me OCH ₂ HOO D2.3 Me COEt 2-Me OCH ₂ HOS D2.4 MeO COEt 2-Me OCH ₂ HOS oil D2.5 MeO COEt 2-Me OCH ₂ HOO oil D2.6 Me COnPr 2-Me OCH ₂ HOS oil D2.7 MeO COnPr 2-Me OCH ₂ HOS oil D2.8 Me COnPr 2 -Me OCH ₂ HOO D2.9 MeO COnPr 2-Me OCH ₂ HOO oil D2.10 MeO COiPr 2-Me OCH ₂ HOS 90-92 D2.11 MeO COnBu 2-Me OCH ₂ HOS oil D2.12 MeO COnBu 2-Me OCH ₂ HOO D2.13 MeO COiBu 2-Me OCH ₂ HOS 78-80 D2.14 MeO CO (c-Bu) 2-Me OCH ₂ HOS 76-78 D2.15 MeO CO (c-pen) 2 -Me OCH ₂ HOS Oil D2.16 Me CO (c-Hex) 2-Me OCH ₂ HOS D2.17 MeO CO (c-Hex) 2-Me OCH ₂ HOS oil D2.18 MeO CO (c-Hex) 2-Me OCH ₂ HOO D2.19 EtO COEt 2-Me OCH ₂ HOS oil D2 .20 MeO COCH ₂ OEt 2-Me OCH ₂ HOS amorphous D2.21 MeO COCH = CHMe 2-Me OCH ₂ HOS oil D2.22 MeO COCH = C (Me) Me 2-Me OCH ₂ HOS oil D2.23 EtO COCH ₂ OMe 2-Me OCH ₂ HOS oil D2.24 EtO COCH ₂ OEt 2-Me OCH ₂ HOS D2.25 Me COCH ₂ OMe 2-Me OCH ₂ HOS oil D2.26 MeO COCH ₂ OMe 2-Me OCH ₂ HOS 70-73 D2.27 Me COCH ₂ OMe 2-Me OCH ₂ HOO D2.28 MeO COCH ₂ OMe 2-Me OCH ₂ HOO oil D2.29 Me COCH ₂ CH ₂ OMe 2-Me OCH ₂ HOS oil D2.30 MeO COCH ₂ CH ₂ OMe 2-Me OCH ₂ HOS oil D2.31 MeO COCH ₂ CH ₂ OMe 2-Me OCH ₂ HOO D2.32 MeO COCH ₂ CH ₂ OEt 2-Me OCH ₂ HOS oil D2.33 MeO COCH ₂ CH ₂ OEt 2-Me OCH ₂ HOO D2.34 Me COCH ₂ CH ₂ OEt 2-Me OCH ₂ HOS D2.35 Me COCH ₂ CH ₂ OEt 2-Me OCH ₂ HOO D2.36 Me COCH _{_{2 CH 2 OnPr 2-Me OCH}} 2 HOS D2.37 MeO COCH 2 CH 2 OnPr 2-Me OCH 2 HOS D2.38 Me COCH 2 CH 2 OnPr 2-Me OCH 2 HOO D2.39 MeO COCH 2 CH 2 OnPr 2 -Me OCH ₂ HOO D2.40 MeO COCH (Cl) Me 2-Me OCH ₂ HOS Oil D2.41 Me COPh 2-Me OCH ₂ HOS 111-113 D2.42 MeO COPh 2-Me OCH ₂ HOS 112-114 D2.43 Me COPh 2-Me OCH ₂ HOO D2.44 MeO COPh 2-Me OCH ₂ HOO Oil D2.45 MeO CO (4-tBu-Ph) 2-Me OCH ₂ HOS 130-131.5 D2.46 MeO CO (2-Cl -Ph) 2-Me OCH ₂ HOS 136-137 D2.47 MeO CO (3-Cl-Ph) 2-Me OCH ₂ HOS 108.5-110.5 D2.48 MeO CO (4-Cl-Ph) 2-Me OCH ₂ HOS amorphous D2.49 MeO CO (4-Cl-Ph) 2-Me OCH ₂ HOO D2.50 MeO CO (2,6-Cl ₂ -Ph) 2-Me OCH ₂ HOS 191-193 D2.51 MeO CO ( 3,4-Cl ₂ -Ph) 2-Me OCH ₂ HOS amorphous D2.52 MeO CO (2,4-F ₂ -Ph) 2-Me OCH ₂ HOS 137-139 D2.53 MeO CO (2,6- F ₂ -Ph) 2-Me OCH ₂ HOS 151-152.5 D2.54 MeO CO (2-MeO-Ph) 2-Me OCH ₂ HOS 126-128 D2.55 MeO CO (2-MeO-Ph) 2-Me OCH ₂ HOO Amorphous D2.56 MeO CO (3-MeO-Ph) 2-Me OCH ₂ HOS Amorphous D2.57 MeO CO (4-MeO-Ph) 2-Me OCH ₂ HOS 126-128 D2.58 MeO CO ( 4-MeO-Ph) 2-Me OCH ₂ HOO D2.59 MeO CO (3,4,5- (MeO) ₃ -Ph) 2-Me OCH ₂ HOS D2.60 MeO CO (2-Me-Ph) 2 -Me OCH ₂ HOS oil D2.61 MeO CO (4-Me-Ph) 2-Me OCH ₂ HOS 132-133 D2.62 MeO CO (4-Me-Ph) 2-Me OCH ₂ HOO D2.63 Me 2-Furo 2-Me OCH ₂ HOS oil D2.64 MeO 2-Furo 2 -Me OCH ₂ HOS D2.65 MeO 2-Furo 2-Me OCH ₂ HOO oil D2.66 MeO 2-Then 2-Me OCH ₂ HOS Clay D2.67 Me 2-Then 2-Me OCH ₂ HOS oil D2.68 MeO Nico 2-Me OCH ₂ HOS 104 D2.69 MeO Nico 2-Me OCH ₂ HOO D2.70 MeO CO (2,4-Me ₂ -1,2,3-Tria-5-yl) 2- Me OCH ₂ HOS D2.71 MeO CO (Isothi-4-yl) 2-Me OCH ₂ HOS D2.72 MeO CO (3-Cl-Benthi-2-yl) 2-Me OCH ₂ HOS 155-157 D2.73 MeO COOMe 2-Me OCH ₂ HOS 163-166 D2.74 MeO COOMe 2-Me OCH ₂ HOO 141-144 D2.75 MeO COOEt 2-Me OCH ₂ HOS 84-86 D2.76 MeO COOEt 2-Me OCH ₂ HOO Oil D2.77 MeO COOnPr 2-Me OCH ₂ HOS Oil D2.78 MeO COOnPr 2-Me OCH ₂ HOO Oil D2.79 MeO COOiPr 2-Me OCH ₂ HOS Oil D2.80 MeO COOnBu 2-Me OCH ₂ HOS oil D2.81 MeO COOnBu 2-Me OCH ₂ HOO oil D2.82 MeO COOiBu 2-Me OCH ₂ HOS oil D2.83 MeO COOCH ₂ CCl ₃ 2-Me OCH ₂ HOS oil D2.84 MeO COOCH ₂ CCl ₃ 2-Me OCH ₂ HOO 102-105 D2.85 MeO COOPh 2-Me OCH ₂ HOS Oil 物

【００５５】[0055]

【表５】 ──────────────────────────────────── 番号 R¹ R² (R³)n ACR⁴(R⁵) (R⁶)m X Q 融点（℃） ──────────────────────────────────── E1.1 Me H H OCHMe H O S 油状物 E1.2 Me H H SCHMe H O S E1.3 MeO H H OCHMe H O S アモルファス E1.4 Me H H OCHMe H O O E1.5 MeO H H OCHMe H O O E1.6 Et H H OCHMe H O S E1.7 nPr H H OCHMe H O S E1.8 iPr H H OCHMe H O S E1.9 nBu H H OCHMe H O S E1.10 FCH₂ H H OCHMe H O S E1.11 F₂CH H H OCHMe H O S E1.12 F₃C H H OCHMe H O S E1.13 ClCH₂ H H OCHMe H O S E1.14 Cl₂CH H H OCHMe H O S E1.15 Me H 2-Me OCHMe H O S 57-60 E1.16 Me H 2-Me SCHMe H O S E1.17 MeO H 2-Me OCHMe H O S アモルファス E1.18 Me H 2-Me OCHMe H O O E1.19 MeO H 2-Me OCHMe H O O E1.20 Et H 2-Me OCHMe H O S E1.210 nPr H 2-Me OCHMe H O S E1.22 iPr H 2-Me OCHMe H O S E1.23 nBu H 2-Me OCHMe H O S E1.24 FCH₂ H 2-Me OCHMe H O S E1.25 F₂CH H 2-Me OCHMe H O S E1.26 F₃C H 2-Me OCHMe H O S E1.27 ClCH₂ H 2-Me OCHMe H O S E1.28 Cl₂CH H 2-Me OCHMe H O S E1.29 Me H 3-Me OCHMe H O S E1.30 Me H 3-Me SCHMe H O S E1.31 MeO H 3-Me OCHMe H O S E1.32 MeO H 3-Me OCHMe H O O E1.33 Et H 3-Me OCHMe H O S E1.34 nPr H 3-Me OCHMe H O S E1.35 iPr H 3-Me OCHMe H O S E1.36 nBu H 3-Me OCHMe H O S E1.37 FCH₂ H 3-Me OCHMe H O S E1.38 F₂CH H 3-Me OCHMe H O S E1.39 F₃C H 3-Me OCHMe H O S E1.40 ClCH₂ H 3-Me OCHMe H O S E1.41 Cl₂CH H 3-Me OCHMe H O S E1.42 Me H 2-Et OCHMe H O S E1.43 Me H 2-Et SCHMe H O S E1.44 MeO H 2-Et OCHMe H O O E1.45 Me H 2-Et OCHMe H O O E1.46 MeO H 2-Et OCHMe H O S E1.47 Et H 2-Et OCHMe H O S E1.48 nPr H 2-Et OCHMe H O S E1.49 iPr H 2-Et OCHMe H O S E1.50 nBu H 2-Et OCHMe H O S E1.51 FCH₂ H 2-Et OCHMe H O S E1.52 F₂CH H 2-Et OCHMe H O S E1.53 F₃C H 2-Et OCHMe H O S E1.54 ClCH₂ H 2-Et OCHMe H O S E1.55 Cl₂CH H 2-Et OCHMe H O S E1.56 Me H 3-Et OCHMe H O S E1.57 Me H 3-Et SCHMe H O S E1.58 Et H 3-Et OCHMe H O S E1.59 nPr H 3-Et OCHMe H O S E1.60 iPr H 3-Et OCHMe H O S E1.61 nBu H 3-Et OCHMe H O S E1.62 FCH₂ H 3-Et OCHMe H O S E1.63 F₂CH H 3-Et OCHMe H O S E1.64 F₃C H 3-Et OCHMe H O S E1.65 ClCH₂ H 3-Et OCHMe H O S E1.66 Cl₂CH H 3-Et OCHMe H O S E2.1 Me H 2-OMe OCHMe H O S E2.2 Me H 2-OMe SCHMe H O S E2.3 MeO H 2-OMe OCHMe H O S E2.4 Et H 2-OMe OCHMe H O S E2.5 nPr H 2-OMe OCHMe H O S E2.6 iPr H 2-OMe OCHMe H O S E2.7 nBu H 2-OMe OCHMe H O S E2.8 FCH₂ H 2-OMe OCHMe H O S E2.9 F₂CH H 2-OMe OCHMe H O S E2.10 F₃C H 2-OMe OCHMe H O S E2.11 ClCH₂ H 2-OMe OCHMe H O S E2.12 Cl₂CH H 2-OMe OCHMe H O S E2.13 Me H 3-OMe OCHMe H O S E2.14 Me H 3-OMe SCHMe H O S E2.15 MeO H 3-OMe OCHMe H O S E2.16 Et H 3-OMe OCHMe H O S E2.17 nPr H 3-OMe OCHMe H O S E2.18 iPr H 3-OMe OCHMe H O S E2.19 nBu H 3-OMe OCHMe H O S E2.20 FCH₂ H 3-OMe OCHMe H O S E2.21 F₂CH H 3-OMe OCHMe H O S E2.22 F₃C H 3-OMe OCHMe H O S E2.23 ClCH₂ H 3-OMe OCHMe H O S E2.24 Cl₂CH H 3-OMe OCHMe H O S E2.25 Me H 2,3-Me₂ OCHMe H O S E2.26 Me H 2,3-Me₂ SCHMe H O S E2.27 MeO H 2,3-Me₂ OCHMe H O S E2.28 Et H 2,3-Me₂ OCHMe H O S E2.29 nPr H 2,3-Me₂ OCHMe H O S E2.30 iPr H 2,3-Me₂ OCHMe H O S E2.31 nBu H 2,3-Me₂ OCHMe H O S E2.32 FCH₂ H 2,3-Me₂ OCHMe H O S E2.34 F₂CH H 2,3-Me₂ OCHMe H O S E2.35 F₃C H 2,3-Me₂ OCHMe H O S E2.36 ClCH₂ H 2,3-Me₂ OCHMe H O S E2.37 Cl₂CH H 2,3-Me₂ OCHMe H O S E3.1 Me H 2-F OCHMe H O S E3.2 Me H 2-F SCHMe H O S E3.3 MeO H 2-F OCHMe H O S E3.4 Me H 2-F OCHMe H O O E3.5 MeO H 2-F OCHMe H O O E3.6 Et H 2-F OCHMe H O S E3.7 nPr H 2-F OCHMe H O S E3.8 iPr H 2-F OCHMe H O S E3.9 nBu H 2-F OCHMe H O S E3.10 FCH₂ H 2-F OCHMe H O S E3.11 F₂CH H 2-F OCHMe H O S E3.12 F₃C H 2-F OCHMe H O S E3.13 ClCH₂ H 2-F OCHMe H O S E3.14 Cl₂CH H 2-F OCHMe H O S E3.15 Me H 3-F OCHMe H O S E3.16 Me H 3-F SCHMe H O S E3.17 Et H 3-F OCHMe H O S E3.18 nPr H 3-F OCHMe H O S E3.19 iPr H 3-F OCHMe H O S E3.20 nBu H 3-F OCHMe H O S E3.21 FCH₂ H 3-F OCHMe H O S E3.22 F₂CH H 3-F OCHMe H O S E3.23 F₃C H 3-F OCHMe H O S E3.24 ClCH₂ H 3-F OCHMe H O S E3.25 Cl₂CH H 3-F OCHMe H O S E3.26 Me H 2-Cl OCHMe H O S E3.27 Me H 2-Cl SCHMe H O S E3.28 MeO H 2-Cl OCHMe H O S E3.29 Me H 2-Cl OCHMe H O O E3.30 MeO H 2-Cl OCHMe H O O E3.31 Et H 2-Cl OCHMe H O S E3.32 nPr H 2-Cl OCHMe H O S E3.33 iPr H 2-Cl OCHMe H O S E3.34 nBu H 2-Cl OCHMe H O S E3.35 FCH₂ H 2-Cl OCHMe H O S E3.36 F₂CH H 2-Cl OCHMe H O S E3.37 F₃C H 2-Cl OCHMe H O S E3.38 ClCH₂ H 2-Cl OCHMe H O S E3.39 Cl₂CH H 2-Cl OCHMe H O S E3.40 Me H 3-Cl OCHMe H O S E3.41 Me H 3-Cl SCHMe H O S E3.42 Et H 3-Cl OCHMe H O S E3.43 nPr H 3-Cl OCHMe H O S E3.45 iPr H 3-Cl OCHMe H O S E3.46 nBu H 3-Cl OCHMe H O S E3.47 FCH₂ H 3-Cl OCHMe H O S E3.48 F₂CH H 3-Cl OCHMe H O S E3.49 F₃C H 3-Cl OCHMe H O S E3.50 ClCH₂ H 3-Cl OCHMe H O S E3.51 Cl₂CH H 3-Cl OCHMe H O S E4.1 Me H H OCMe₂ H O S 149-150 E4.2 Me H H SCMe₂ H O S E4.3 MeO H H OCMe₂ H O S E4.4 MeO H H OCMe₂ H O O E4.5 Et H H OCMe₂ H O S E4.6 nPr H H OCMe₂ H O S E4.7 iPr H H OCMe₂ H O S E4.8 nBu H H OCMe₂ H O S E4.9 FCH₂ H H OCMe₂ H O S E4.10 F₂CH H H OCMe₂ H O S E4.11 F₃C H H OCMe₂ H O S E4.12 ClCH₂ H H OCMe₂ H O S E4.13 Cl₂CH H H OCMe₂ H O S E4.14 Me H 2-Me OCMe₂ H O S E4.15 Me H 2-Me SCMe₂ H O S E4.16 MeO H 2-Me OCMe₂ H O S E4.17 Me H 2-Me OCMe₂ H O O E4.18 MeO H 2-Me OCMe₂ H O O E4.19 Et H 2-Me OCMe₂ H O S E4.20 nPr H 2-Me OCMe₂ H O S E4.21 iPr H 2-Me OCMe₂ H O S E4.22 nBu H 2-Me OCMe₂ H O S E4.23 FCH₂ H 2-Me OCMe₂ H O S E4.24 F₂CH H 2-Me OCMe₂ H O S E4.25 F₃C H 2-Me OCMe₂ H O S E4.26 ClCH₂ H 2-Me OCMe₂ H O S E4.27 Cl₂CH H 2-Me OCMe₂ H O S E4.28 Me H 3-Me OCMe₂ H O S E4.29 Me H 3-Me SCMe₂ H O S E4.30 MeO H 3-Me OCMe₂ H O S E4.31 Et H 3-Me OCMe₂ H O S E4.32 nPr H 3-Me OCMe₂ H O S E4.33 iPr H 3-Me OCMe₂ H O S E4.34 nBu H 3-Me OCMe₂ H O S E4.35 FCH₂ H 3-Me OCMe₂ H O S E4.36 F₂CH H 3-Me OCMe₂ H O S E4.37 F₃C H 3-Me OCMe₂ H O S E4.38 ClCH₂ H 3-Me OCMe₂ H O S E4.39 Cl₂CH H 3-Me OCMe₂ H O S E4.41 Me H 2-Et SCMe₂ H O S E4.42 Et H 2-Et OCMe₂ H O S E4.43 nPr H 2-Et OCMe₂ H O S E4.44 iPr H 2-Et OCMe₂ H O S E4.45 nBu H 2-Et OCMe₂ H O S E4.46 FCH₂ H 2-Et OCMe₂ H O S E4.47 F₂CH H 2-Et OCMe₂ H O S E4.48 F₃C H 2-Et OCMe₂ H O S E4.49 ClCH₂ H 2-Et OCMe₂ H O S E4.50 Cl₂CH H 2-Et OCMe₂ H O S E4.51 Me H 3-Et OCMe₂ H O S E4.52 Me H 3-Et SCMe₂ H O S E4.53 Et H 3-Et OCMe₂ H O S E4.54 nPr H 3-Et OCMe₂ H O S E4.55 iPr H 3-Et OCMe₂ H O S E4.56 nBu H 3-Et OCMe₂ H O S E4.57 FCH₂ H 3-Et OCMe₂ H O S E4.58 F₂CH H 3-Et OCMe₂ H O S E4.59 F₃C H 3-Et OCMe₂ H O S E4.60 ClCH₂ H 3-Et OCMe₂ H O S E4.61 Cl₂CH H 3-Et OCMe₂ H O S E4.62 Me H 2,3-Me₂ OCMe₂ H O S E4.63 Me H 2,3-Me₂ SCMe₂ H O S E4.64 Et H 2,3-Me₂ OCMe₂ H O S E4.65 nPr H 2,3-Me₂ OCMe₂ H O S E4.66 iPr H 2,3-Me₂ OCMe₂ H O S E4.67 nBu H 2,3-Me₂ OCMe₂ H O S E4.68 FCH₂ H 2,3-Me₂ OCMe₂ H O S E4.69 F₂CH H 2,3-Me₂ OCMe₂ H O S E4.70 F₃C H 2,3-Me₂ OCMe₂ H O S E4.71 ClCH₂ H 2,3-Me₂ OCMe₂ H O S E4.72 Cl₂CH H 2,3-Me₂ OCMe₂ H O S E5.1 Me H 2-F OCMe₂ H O S E5.2 Me H 2-F SCMe₂ H O S E5.3 Et H 2-F OCMe₂ H O S E5.4 nPr H 2-F OCMe₂ H O S E5.5 iPr H 2-F OCMe₂ H O S E5.6 nBu H 2-F OCMe₂ H O S E5.7 FCH₂ H 2-F OCMe₂ H O S E5.8 F₂CH H 2-F OCMe₂ H O S E5.9 F₃C H 2-F OCMe₂ H O S E5.10 ClCH₂ H 2-F OCMe₂ H O S E5.11 Cl₂CH H 2-F OCMe₂ H O S E5.12 Me H 3-F OCMe₂ H O S E5.13 Me H 3-F SCMe₂ H O S E5.14 Et H 3-F OCMe₂ H O S E5.15 nPr H 3-F OCMe₂ H O S E5.16 iPr H 3-F OCMe₂ H O S E5.17 nBu H 3-F OCMe₂ H O S E5.18 FCH₂ H 3-F OCMe₂ H O S E5.19 F₂CH H 3-F OCMe₂ H O S E5.20 F₃C H 3-F OCMe₂ H O S E5.21 ClCH₂ H 3-F OCMe₂ H O S E5.22 Cl₂CH H 3-F OCMe₂ H O S E5.23 Me H 2-Cl OCMe₂ H O S E5.24 Me H 2-Cl SCMe₂ H O S E5.25 Et H 2-Cl OCMe₂ H O S E5.27 iPr H 2-Cl OCMe₂ H O S E5.28 nBu H 2-Cl OCMe₂ H O S E5.29 FCH₂ H 2-Cl OCMe₂ H O S E5.30 F₂CH H 2-Cl OCMe₂ H O S E5.31 F₃C H 2-Cl OCMe₂ H O S E5.32 ClCH₂ H 2-Cl OCMe₂ H O S E5.33 Cl₂CH H 2-Cl OCMe₂ H O S E5.34 Me H 3-Cl OCMe₂ H O S E5.35 Me H 3-Cl SCMe₂ H O S E5.36 Et H 3-Cl OCMe₂ H O S E5.37 nPr H 3-Cl OCMe₂ H O S E5.38 iPr H 3-Cl OCMe₂ H O S E5.40 nBu H 3-Cl OCMe₂ H O S E5.41 FCH₂ H 3-Cl OCMe₂ H O S E5.42 F₂CH H 3-Cl OCMe₂ H O S E5.43 F₃C H 3-Cl OCMe₂ H O S E5.44 ClCH₂ H 3-Cl OCMe₂ H O S E5.45 Cl₂CH H 3-Cl OCMe₂ H O S E5.46 Me H 2-OMe OCMe₂ H O S E5.47 Me H 2-OMe SCMe₂ H O S E5.48 Et H 2-OMe OCMe₂ H O S E5.49 nPr H 2-OMe OCMe₂ H O S E5.50 iPr H 2-OMe OCMe₂ H O S E5.51 nBu H 2-OMe OCMe₂ H O S E5.52 FCH₂ H 2-OMe OCMe₂ H O S E5.53 F₂CH H 2-OMe OCMe₂ H O S E5.54 F₃C H 2-OMe OCMe₂ H O S E5.55 ClCH₂ H 2-OMe OCMe₂ H O S E5.56 Cl₂CH H 2-OMe OCMe₂ H O S E5.57 Me H 3-OMe OCMe₂ H O S E5.58 Me H 3-OMe SCMe₂ H O S E5.59 Et H 3-OMe OCMe₂ H O S E5.60 nPr H 3-OMe OCMe₂ H O S E5.61 iPr H 3-OMe OCMe₂ H O S E5.62 nBu H 3-OMe OCMe₂ H O S E5.63 FCH₂ H 3-OMe OCMe₂ H O S E5.64 F₂CH H 3-OMe OCMe₂ H O S E5.65 F₃C H 3-OMe OCMe₂ H O S E5.66 ClCH₂ H 3-OMe OCMe₂ H O S E5.67 Cl₂CH H 3-OMe OCMe₂ H O S E6.1 Me H H OCHEt H O S 油状物 E6.2 Me H H SCHEt H O S E6.3 MeO H H OCHEt H O S E6.4 Me H H OCHEt H O O E6.5 MeO H H OCHEt H O O E6.6 Et H H OCHEt H O S E6.7 nPr H H OCHEt H O S E6.8 iPr H H OCHEt H O S E6.9 nBu H H OCHEt H O S E7.0 FCH₂ H H OCHEt H O S E7.1 F₂CH H H OCHEt H O S E7.2 F₃C H H OCHEt H O S E7.3 ClCH₂ H H OCHEt H O S E7.4 Cl₂CH H H OCHEt H O S E7.5 Me H 2-Me OCHEt H O S 粘土状 E7.6 Me H 2-Me SCHEt H O S E7.7 MeO H 2-Me OCHEt H O S E7.8 Me H 2-Me OCHEt H O O E7.9 MeO H 2-Me OCHEt H O O E7.10 Me Et 2-Me OCHEt H O S 油状物 E7.11 MeO Et 2-Me OCHEt H O S E7.12 Et H 2-Me OCHEt H O S E7.13 nPr H 2-Me OCHEt H O S E7.14 iPr H 2-Me OCHEt H O S E7.15 nBu H 2-Me OCHEt H O S E7.16 FCH₂ H 2-Me OCHEt H O S E7.17 F₂CH H 2-Me OCHEt H O S E7.18 F₃C H 2-Me OCHEt H O S E7.19 ClCH₂ H 2-Me OCHEt H O S E7.20 Cl₂CH H 2-Me OCHEt H O S E7.21 Me H 3-Me OCHEt H O S E7.22 Me H 3-Me SCHEt H O S E7.23 Et H 3-Me OCHEt H O S E7.24 nPr H 3-Me OCHEt H O S E7.25 iPr H 3-Me OCHEt H O S E7.26 nBu H 3-Me OCHEt H O S E7.27 FCH₂ H 3-Me OCHEt H O S E7.28 F₂CH H 3-Me OCHEt H O S E7.29 F₃C H 3-Me OCHEt H O S E7.30 ClCH₂ H 3-Me OCHEt H O S E7.31 Cl₂CH H 3-Me OCHEt H O S E7.32 Me H 2-Et OCHEt H O S E7.33 Me H 2-Et SCHEt H O S E7.34 Et H 2-Et OCHEt H O S E7.35 nPr H 2-Et OCHEt H O S E7.36 iPr H 2-Et OCHEt H O S E7.37 nBu H 2-Et OCHEt H O S E7.38 FCH₂ H 2-Et OCHEt H O S E7.39 F₂CH H 2-Et OCHEt H O S E7.40 F₃C H 2-Et OCHEt H O S E7.41 ClCH₂ H 2-Et OCHEt H O S E7.42 Cl₂CH H 2-Et OCHEt H O S E7.43 Me H 3-Et OCHEt H O S E7.44 Me H 3-Et SCHEt H O S E7.45 Et H 3-Et OCHEt H O S E7.46 nPr H 3-Et OCHEt H O S E7.47 iPr H 3-Et OCHEt H O S E7.48 nBu H 3-Et OCHEt H O S E7.49 FCH₂ H 3-Et OCHEt H O S E7.50 F₂CH H 3-Et OCHEt H O S E7.51 F₃C H 3-Et OCHEt H O S E7.52 ClCH₂ H 3-Et OCHEt H O S E7.53 Cl₂CH H 3-Et OCHEt H O S E7.54 Me H 2,3-Me₂ OCHEt H O S E7.55 Me H 2,3-Me₂ SCHEt H O S E7.56 Et H 2,3-Me₂ OCHEt H O S E7.57 nPr H 2,3-Me₂ OCHEt H O S E7.58 iPr H 2,3-Me₂ OCHEt H O S E7.59 nBu H 2,3-Me₂ OCHEt H O S E7.60 FCH₂ H 2,3-Me₂ OCHEt H O S E7.61 F₂CH H 2,3-Me₂ OCHEt H O S E7.62 F₃C H 2,3-Me₂ OCHEt H O S E7.63 ClCH₂ H 2,3-Me₂ OCHEt H O S E7.64 Cl₂CH H 2,3-Me₂ OCHEt H O S E7.65 Me H 2-F OCHEt H O S E7.66 Me H 2-F SCHEt H O S E7.67 Et H 2-F OCHEt H O S E7.68 nPr H 2-F OCHEt H O S E7.69 iPr H 2-F OCHEt H O S E7.70 nBu H 2-F OCHEt H O S E7.71 FCH₂ H 2-F OCHEt H O S E7.72 F₂CH H 2-F OCHEt H O S E7.73 F₃C H 2-F OCHEt H O S E7.74 ClCH₂ H 2-F OCHEt H O S E7.75 Cl₂CH H 2-F OCHEt H O S E7.76 Me H 3-F OCHEt H O S E7.77 Me H 3-F SCHEt H O S E7.78 Et H 3-F OCHEt H O S E7.79 nPr H 3-F OCHEt H O S E7.80 iPr H 3-F OCHEt H O S E7.81 nBu H 3-F OCHEt H O S E7.82 FCH₂ H 3-F OCHEt H O S E7.83 F₂CH H 3-F OCHEt H O S E7.84 F₃C H 3-F OCHEt H O S E7.85 ClCH₂ H 3-F OCHEt H O S E7.86 Cl₂CH H 3-F OCHEt H O S E7.87 Me H 2-Cl OCHEt H O S E7.88 Me H 2-Cl SCHEt H O S E7.89 Et H 2-Cl OCHEt H O S E7.90 nPr H 2-Cl OCHEt H O S E7.91 iPr H 2-Cl OCHEt H O S E7.92 nBu H 2-Cl OCHEt H O S E7.93 FCH₂ H 2-Cl OCHEt H O S E7.94 F₂CH H 2-Cl OCHEt H O S E7.95 F₃C H 2-Cl OCHEt H O S E7.96 ClCH₂ H 2-Cl OCHEt H O S E7.97 Cl₂CH H 2-Cl OCHEt H O S E7.98 Me H 3-Cl OCHEt H O S E7.99 Me H 3-Cl SCHEt H O S E7.100 Et H 3-Cl OCHEt H O S E7.101 nPr H 3-Cl OCHEt H O S E7.102 iPr H 3-Cl OCHEt H O S E7.103 nBu H 3-Cl OCHEt H O S E7.104 FCH₂ H 3-Cl OCHEt H O S E7.105 F₂CH H 3-Cl OCHEt H O S E7.106 F₃C H 3-Cl OCHEt H O S E7.107 ClCH₂ H 3-Cl OCHEt H O S E7.108 Cl₂CH H 3-Cl OCHEt H O S E7.109 Me H 2-OMe OCHEt H O S E7.110 Me H 2-OMe SCHEt H O S E7.111 Et H 2-OMe OCHEt H O S E7.112 nPr H 2-OMe OCHEt H O S E7.113 iPr H 2-OMe OCHEt H O S E7.114 nBu H 2-OMe OCHEt H O S E7.115 FCH₂ H 2-OMe OCHEt H O S E7.116 F₂CH H 2-OMe OCHEt H O S E7.117 F₃C H 2-OMe OCHEt H O S E7.118 ClCH₂ H 2-OMe OCHEt H O S E7.119 Cl₂CH H 2-OMe OCHEt H O S E7.120 Me H 3-OMe OCHEt H O S E7.121 Me H 3-OMe SCHEt H O S E7.122 Et H 3-OMe OCHEt H O S E7.123 nPr H 3-OMe OCHEt H O S E7.124 iPr H 3-OMe OCHEt H O S E7.125 nBu H 3-OMe OCHEt H O S E7.126 FCH₂ H 3-OMe OCHEt H O S E7.127 F₂CH H 3-OMe OCHEt H O S E7.128 F₃C H 3-OMe OCHEt H O S E7.129 ClCH₂ H 3-OMe OCHEt H O S E7.130 Cl₂CH H 3-OMe OCHEt H O S E7.131 Me H H OCHiPr H O S 油状物 E7.132 MeO H H OCHiPr H O S E7.133 Me H H OCHiPr H O O E7.134 MeO H H OCHiPr H O O E7.135 Me H 2-Me OCHiPr H O S 油状物 E7.136 MeO H 2-Me OCHiPr H O S E7.137 Me H 2-Me OCHiPr H O O E7.138 MeO H 2-Me OCHiPr H O O ────────────────────────────────────[Table 5] ──────────────────────────────────── Number R ¹ R ² (R ³ ) n ACR ⁴ (R ⁵ ) (R ⁶ ) m XQ Melting point (℃) ────────────────────────────────── ── E1.1 Me HH OCHMe HOS Oil E1.2 Me HH SCHMe HOS E1.3 MeO HH OCHMe HOS Amorphous E1.4 Me HH OCHMe HOO E1.5 MeO HH OCHMe HOO E1.6 Et HH OCHMe HOS E1.7 nPr HH OCHMe HOS E1.8 iPr HH OCHMe HOS E1.9 nBu HH OCHMe HOS E1.10 FCH ₂ HH OCHMe HOS E1.11 F ₂ CH HH OCHMe HOS E1.12 F ₃ CHH OCHMe HOS E1.13 ClCH ₂ HH OCHMe HOS E1.14 Cl ₂ CH HH OCHMe HOS E1.15 Me H 2-Me OCHMe HOS 57-60 E1.16 Me H 2-Me SCHMe HOS E1.17 MeO H 2-Me OCHMe HOS Amorphous E1.18 Me H 2 -Me OCHMe HOO E1.19 MeO H 2-Me OCHMe HOO E1.20 Et H 2-Me OCHMe HOS E1.210 nPr H 2-Me OCHMe HOS E1.22 iPr H 2-Me OCHMe HOS E1.23 nBu H 2 -Me OCHMe HOS E1.24 FCH ₂ H 2-Me OCHMe HOS E1.25 F ₂ CH H 2-Me OCHMe HOS E1.26 F ₃ CH 2-Me OCHMe HOS E1. 27 ClCH ₂ H 2-Me OCHMe HOS E1.28 Cl ₂ CH H 2-Me OCHMe HOS E1.29 Me H 3-Me OCHMe HOS E1.30 Me H 3-Me SCHMe HOS E1.31 MeO H 3-Me OCHMe HOS E1.32 MeO H 3-Me OCHMe HOO E1.33 Et H 3-Me OCHMe HOS E1.34 nPr H 3-Me OCHMe HOS E1.35 iPr H 3-Me OCHMe HOS E1.36 nBu H 3-Me OCHMe HOS E1.37 FCH ₂ H 3-Me OCHMe HOS E1.38 F ₂ CH H 3-Me OCHMe HOS E1.39 F ₃ CH 3-Me OCHMe HOS E1.40 ClCH ₂ H 3-Me OCHMe HOS E1.41 Cl ₂ CH H 3-Me OCHMe HOS E1.42 Me H 2-Et OCHMe HOS E1.43 Me H 2-Et SCHMe HOS E1.44 MeO H 2-Et OCHMe HOO E1.45 Me H 2-Et OCHMe HOO E1. 46 MeO H 2-Et OCHMe HOS E1.47 Et H 2-Et OCHMe HOS E1.48 nPr H 2-Et OCHMe HOS E1.49 iPr H 2-Et OCHMe HOS E1.50 nBu H 2-Et OCHMe HOS E1. 51 FCH ₂ H 2-Et OCHMe HOS E1.52 F ₂ CH H 2-Et OCHMe HOS E1.53 F ₃ CH 2-Et OCHMe HOS E1.54 ClCH ₂ H 2-Et OCHMe HOS E1.55 Cl ₂ CH H 2-Et OCHMe HOS E1.56 Me H 3-Et OCHMe HOS E1.57 Me H 3-Et SCHMe HOS E1.58 Et H 3-Et OCHMe HOS E1.59 nPr H 3-Et OCHMe HOS E1.60 iPr H 3-Et OCHMe HOS E1.61 nBu H 3-Et OCHMe HOS E1.62 FCH ₂ H 3-Et OCHMe HOS E1.63 F ₂ CH H 3-Et OCHMe HOS E1.64 F ₃ CH 3-Et OCHMe HOS E1.65 ClCH ₂ H 3-Et OCHMe HOS E1.66 Cl ₂ CH H 3-Et OCHMe HOS E2.1 Me H 2- OMe OCHMe HOS E2.2 Me H 2-OMe SCHMe HOS E2.3 MeO H 2-OMe OCHMe HOS E2.4 Et H 2-OMe OCHMe HOS E2.5 nPr H 2-OMe OCHMe HOS E2.6 iPr H 2- OMe OCHMe HOS E2.7 nBu H 2-OMe OCHMe HOS E2.8 FCH ₂ H 2-OMe OCHMe HOS E2.9 F ₂ CH H 2-OMe OCHMe HOS E2.10 F ₃ CH 2-OMe OCHMe HOS E2.11 ClCH ₂ H 2-OMe OCHMe HOS E2.12 Cl ₂ CH H 2-OMe OCHMe HOS E2.13 Me H 3-OMe OCHMe HOS E2.14 Me H 3-OMe SCHMe HOS E2.15 MeO H 3-OMe OCHMe HOS E2.16 Et H 3-OMe OCHMe HOS E2.17 nPr H 3-OMe OCHMe HOS E2.18 iPr H 3-OMe OCHMe HOS E2.19 nBu H 3-OMe OCHMe HOS E2.20 FCH ₂ H 3-OMe OCHMe HOS E2.21 F ₂ CH H 3-OMe OCHMe HOS E2.22 F ₃ CH 3-OMe OCHMe HOS E2.23 ClCH ₂ H 3-OMe OCHMe HOS E2.24 Cl ₂ CH H 3-OMe OCHMe HOS E2.25 Me H 2,3-Me ₂ OCHMe HOS E2.26 Me H 2,3-Me ₂ SCHMe HOS E2.27 MeO H 2,3-Me ₂ OCHMe HOS E2.28 Et H 2,3-Me ₂ OCHMe HOS E2 .29 nPr H 2,3-Me ₂ OCHMe HOS E2.30 iPr H 2,3-Me ₂ OCHMe HOS E2.31 nBu H 2,3-Me ₂ OCHMe HOS E2.32 FCH ₂ H 2,3-Me ₂ OCHMe HOS E2.34 F ₂ CH H 2,3-Me ₂ OCHMe HOS E2.35 F ₃ CH 2,3-Me ₂ OCHMe HOS E2.36 ClCH ₂ H 2,3-Me ₂ OCHMe HOS E2.37 Cl ₂ CH H 2,3-Me ₂ OCHMe HOS E3.1 Me H 2-F OCHMe HOS E3.2 Me H 2-F SCHMe HOS E3.3 MeO H 2 -F OCHMe HOS E3.4 Me H 2-F OCHMe HOO E3.5 MeO H 2-F OCHMe HOO E3.6 Et H 2-F OCHMe HOS E3.7 nPr H 2-F OCHMe HOS E3.8 iPr H 2 -F OCHMe HOS E3.9 nBu H 2-F OCHMe HOS E3.10 FCH ₂ H 2-F OCHMe HOS E3.11 F ₂ CH H 2-F OCHMe HOS E3.12 F ₃ CH 2-F OCHMe HOS E3. 13 ClCH ₂ H 2-F OCHMe HOS E3.14 Cl ₂ CH H 2-F OCHMe HOS E3.15 Me H 3-F OCHMe HOS E3.16 Me H 3-F SCHMe HOS E3.17 Et H 3-F OCHMe HOS E3.18 nPr H 3-F OCHMe HOS E3.19 iPr H 3-F OCHMe HOS E3.20 nBu H 3-F OCHMe HOS E3.21 FCH ₂ H 3-F OCHMe HOS E3.22 F ₂ CH H 3 -F OCHMe HOS E3.23 F ₃ CH 3-F OCHMe HOS E3.24 ClCH ₂ H 3-F OCHMe HOS E3.25 Cl ₂ CH H 3-F OCHMe HOS E3.26 Me H 2-Cl OCHMe HOS E3. 27 Me H 2-Cl SCHMe HOS E3.28 MeO H 2-Cl OCHMe HOS E3.29 Me H 2-Cl OCHMe HOO E3.30 MeO H 2-Cl OCHMe HOO E3.31 Et H 2-Cl OCHMe HOS E3. Three 2 nPr H 2-Cl OCHMe HOS E3.33 iPr H 2-Cl OCHMe HOS E3.34 nBu H 2-Cl OCHMe HOS E3.35 FCH ₂ H 2-Cl OCHMe HOS E3.36 F ₂ CH H 2-Cl OCHMe HOS E3.37 F ₃ CH 2-Cl OCHMe HOS E3.38 ClCH ₂ H 2-Cl OCHMe HOS E3.39 Cl ₂ CH H 2-Cl OCHMe HOS E3.40 Me H 3-Cl OCHMe HOS E3.41 Me H 3-Cl SCHMe HOS E3.42 Et H 3-Cl OCHMe HOS E3.43 nPr H 3-Cl OCHMe HOS E3.45 iPr H 3-Cl OCHMe HOS E3.46 nBu H 3-Cl OCHMe HOS E3.47 FCH ₂ H 3-Cl OCHMe HOS E3.48 F ₂ CH H 3-Cl OCHMe HOS E3.49 F ₃ CH 3-Cl OCHMe HOS E3.50 ClCH ₂ H 3-Cl OCHMe HOS E3.51 Cl ₂ CH H 3-Cl OCHMe HOS E4.1 Me HH OCMe ₂ HOS 149-150 E4.2 Me HH SCMe ₂ HOS E4.3 MeO HH OCMe ₂ HOS E4.4 MeO HH OCMe ₂ HOO E4.5 Et HH OCMe ₂ HOS E4.6 nPr HH OCMe ₂ HOS E4.7 iPr HH OCMe ₂ HOS E4.8 nBu HH OCMe ₂ HOS E4.9 FCH ₂ HH OCMe ₂ HOS E4.10 F ₂ CH HH OCMe ₂ HOS E4.11 F ₃ CHH OCMe ₂ HOS E4.12 ClCH ₂ HH OCMe ₂ HOS E4.13 Cl ₂ CH HH OCMe ₂ HOS E4.14 Me H 2-Me OCMe ₂ HOS E4.15 Me H 2-Me SCMe ₂ HOS E4.16 MeO H 2-Me OCMe ₂ HOS E4 .17 Me H 2-Me OCMe ₂ HOO E4.18 MeO H 2-Me OCMe ₂ HOO E4.19 Et H 2-Me OCMe ₂ HOS E4.20 nPr H 2-Me OCMe ₂ HOS E4.21 iPr H 2-Me OCMe ₂ HOS E4.22 nBu H 2-Me OCMe ₂ HOS E4.23 FCH ₂ H 2-Me OCMe ₂ HOS E4.24 F ₂ CH H 2-Me OCMe ₂ HOS E4.25 F ₃ CH 2-Me OCMe ₂ HOS E4.26 ClCH ₂ H 2-Me OCMe ₂ HOS E4.27 Cl ₂ CH H 2-Me OCMe ₂ HOS E4.28 Me H 3-Me OCMe ₂ HOS E4.29 Me H 3-Me SCMe ₂ HOS E4.30 MeO H 3-Me OCMe ₂ HOS E4.31 Et H 3-Me OCMe ₂ HOS E4.32 nPr H 3-Me OCMe ₂ HOS E4.33 iPr H 3-Me OCMe ₂ HOS E4.34 nBu H 3-Me OCMe ₂ HOS E4.35 FCH ₂ H 3-Me OCMe ₂ HOS E4.36 F ₂ CH H 3-Me OCMe ₂ HOS E4.37 F ₃ CH 3-Me OCMe ₂ HOS E4.38 ClCH ₂ H 3-Me OCMe ₂ HOS E4.39 Cl ₂ CH H 3-Me OCMe ₂ HOS E4.41 Me H 2-Et SCMe ₂ HOS E4.42 Et H 2-Et OCMe ₂ HOS E4.43 nPr H 2-Et OCMe ₂ HOS E4.44 iPr H 2-Et OCMe ₂ HOS E4.45 nBu H 2-Et OCMe ₂ HOS E4.46 FCH ₂ H 2-Et OCMe ₂ HOS E4.47 F ₂ CH H 2-Et OCMe ₂ HOS E4.48 F ₃ CH 2-Et OCMe ₂ HOS E4.49 ClCH ₂ H 2-Et OCMe ₂ HOS E4.50 Cl ₂ CH H 2-Et OCMe ₂ HOS E4.51 Me H 3-Et OCMe ₂ HOS E4.52 Me H 3-Et SCMe ₂ HOS E4.53 Et H 3-Et OCMe ₂ HOS E4.54 nPr H 3-Et OCMe ₂ HOS E4.55 iPr H 3-Et OCMe ₂ HOS E4.56 nBu H 3-Et OCMe ₂ HOS E4.57 FCH ₂ H 3-Et OCMe ₂ HOS E4.58 F ₂ CH H 3-Et OCMe ₂ HOS E4.59 F ₃ CH 3-Et OCMe ₂ HOS E4.60 ClCH ₂ H 3-Et OCMe ₂ HOS E4.61 Cl ₂ CH H 3-Et OCMe ₂ HOS E4.62 Me H 2,3-Me ₂ OCMe ₂ HOS E4. 63 Me H 2,3-Me ₂ SCMe ₂ HOS E4.64 Et H 2,3-Me ₂ OCMe ₂ HOS E4.65 nPr H 2,3-Me ₂ OCMe ₂ HOS E4.66 iPr H 2,3-Me ₂ OCMe ₂ HOS E4.67 nBu H 2,3-Me ₂ OCMe ₂ HOS E4.68 FCH ₂ H 2,3-Me ₂ OCMe ₂ HOS E4.69 F ₂ CH H 2,3-Me ₂ OCMe ₂ HOS E4 .70 F ₃ CH 2,3-Me ₂ OCMe ₂ HOS E4.71 ClCH ₂ H 2,3-Me ₂ OCMe ₂ HOS E4.72 Cl ₂ CH H 2,3-Me ₂ OCMe ₂ HOS E5.1 Me H 2-F OCMe ₂ HOS E5.2 Me H 2-F SCMe ₂ HOS E5.3 Et H 2-F OCMe ₂ HOS E5.4 nPr H 2-F OCMe ₂ HOS E5.5 iPr H 2-F OCMe ₂ HOS E5.6 nBu H 2-F OCMe ₂ HOS E5.7 FCH ₂ H 2-F OCMe ₂ HOS E5.8 F ₂ CH H 2-F OCMe ₂ HOS E5.9 F ₃ CH 2-F OCMe ₂ HOS E5. 10 ClCH ₂ H 2-F OCMe ₂ HOS E5.11 Cl ₂ CH H 2-F OCMe ₂ HOS E5.12 Me H 3-F OCMe ₂ HOS E5.13 Me H 3-F SCMe ₂ HOS E5.14 Et H 3-F OCMe ₂ HOS E5.15 nPr H 3-F OCMe ₂ HOS E5.16 iPr H 3-F OCMe ₂ HOS E5.17 nBu H 3-F OCMe ₂ HOS E5.18 FCH ₂ H 3-F OCMe ₂ HOS E5.19 F ₂ CH H 3-F OCMe ₂ HOS E5.20 F ₃ CH 3-F OCMe ₂ HOS E5. 21 ClCH ₂ H 3-F OCMe ₂ HOS E5.22 Cl ₂ CH H 3-F OCMe ₂ HOS E5.23 Me H 2-Cl OCMe ₂ HOS E5.24 Me H 2-Cl SCMe ₂ HOS E5.25 Et H 2-Cl OCMe ₂ HOS E5.27 iPr H 2-Cl OCMe ₂ HOS E5.28 nBu H 2-Cl OCMe ₂ HOS E5.29 FCH ₂ H 2-Cl OCMe ₂ HOS E5.30 F ₂ CH H 2-Cl OCMe ₂ HOS E5.31 F ₃ CH 2-Cl OCMe ₂ HOS E5.32 ClCH ₂ H 2-Cl OCMe ₂ HOS E5.33 Cl ₂ CH H 2-Cl OCMe ₂ HOS E5.34 Me H 3-Cl OCMe ₂ HOS E5.35 Me H 3-Cl SCMe ₂ HOS E5.36 Et H 3-Cl OCMe ₂ HOS E5.37 nPr H 3-Cl OCMe ₂ HOS E5.38 iPr H 3-Cl OCMe ₂ HOS E5.40 nBu H 3-Cl OCMe ₂ HOS E5.41 FCH ₂ H 3-Cl OCMe ₂ HOS E5.42 F ₂ CH H 3-Cl OCMe ₂ HOS E5.43 F ₃ CH 3-Cl OCMe ₂ HOS E5.44 ClCH ₂ H 3 -Cl OCMe ₂ HOS E5.45 Cl ₂ CH H 3-Cl OCMe ₂ HOS E5.46 Me H 2-OMe OCMe ₂ HOS E5.47 Me H 2-OMe SCMe ₂ HOS E5.48 Et H 2-OMe OCMe ₂ HOS E5.49 nPr H 2-OMe OCMe ₂ HOS E5.50 iPr H 2-OMe OCMe ₂ HOS E5.51 nBu H 2-OMe OCMe ₂ HOS E5.52 FCH ₂ H 2-OMe OCMe ₂ HOS E5.53 F ₂ CH H 2-OMe OCMe ₂ HOS E5.54 F ₃ CH 2-OMe OCMe ₂ HOS E5.55 ClCH ₂ H 2-OMe OCMe ₂ HOS E5.56 Cl ₂ CH H 2-OMe OCMe ₂ HOS E5.57 Me H 3- OMe OCMe ₂ HOS E5.58 Me H 3-OMe SCMe ₂ HOS E5.59 Et H 3-OMe OCMe ₂ HOS E5.60 nPr H 3-OMe OCMe ₂ HOS E5.61 iPr H 3-OMe OCMe ₂ HOS E5. 62 nBu H 3-OMe OCMe ₂ HOS E5.63 FCH ₂ H 3-OMe OCMe ₂ HOS E5.64 F ₂ CH H 3-OMe OCMe ₂ HOS E5.65 F ₃ CH 3-OMe OCMe ₂ HOS E5.66 ClCH ₂ H 3-OMe OCMe ₂ HOS E5.67 Cl ₂ CH H 3-OMe OCMe ₂ HOS E6.1 Me HH OCHEt HOS Oil E6.2 Me HH SCHEt HOS E6.3 MeO HH OCHEt HOS E6.4 Me HH OCHEt HOO E6.5 MeO HH OCHEt HOO E6.6 Et HH OCHEt HOS E6.7 nPr HH OCHEt HOS E6.8 iPr HH OCHEt HOS E6.9 nBu HH OCHEt HOS E7.0 FCH ₂ HH OCHEt HOS E7.1 F ₂ CH HH OCHEt HOS E7.2 F ₃ CHH OCHEt HOS E7.3 ClCH ₂ HH OCHEt HOS E7.4 Cl ₂ CH HH OCHEt HOS E7.5 Me H 2-Me OCHEt HOS Clayy E7.6 Me H 2-Me SCHEt HOS E7.7 MeO H 2-Me OCHEt HOS E7.8 Me H 2-Me OCHEt HOO E7.9 MeO H 2-Me OCHEt HOO E7.10 Me Et 2-Me OCHEt HOS Oil E7.11 MeO Et 2-Me OCHEt HOS E7.12 Et H 2-Me OCHEt HOS E7. 13 nPr H 2-Me OCHEt HOS E7.14 iPr H 2-Me OCHEt HOS E7.15 nBu H 2-Me OCHEt HOS E7.16 FCH ₂ H 2-Me OCHEt HOS E7.17 F ₂ CH H 2-Me OCHEt HOS E7.18 F ₃ CH 2-Me OCHEt HOS E7.19 ClCH ₂ H 2-Me OCHEt HOS E7.20 Cl ₂ CH H 2-Me OCHEt HOS E7.21 Me H 3-Me OCHEt HOS E7.22 Me H 3-Me SCHEt HOS E7.23 Et H 3-Me OCHEt HOS E7.24 nPr H 3-Me OCHEt HOS E7.25 iPr H 3-Me OCHEt HOS E7.26 nBu H 3-Me OCHEt HOS E7.27 FCH ₂ H 3-Me OCHEt HOS E7.28 F ₂ CH H 3-Me OCHEt HOS E7.29 F ₃ CH 3-Me OCHEt HOS E7.30 ClCH ₂ H 3-Me OCHEt HOS E7.31 Cl ₂ CH H 3-Me OCHEt HOS E7.32 Me H 2-Et OCHEt HOS E7.33 Me H 2-Et SCHEt HOS E7.34 Et H 2-Et OCHEt HOS E7.35 nPr H 2-Et OCHEt HOS E7.36 iPr H 2-Et OCHEt HOS E7.37 nBu H 2-Et OCHEt HOS E7.38 FCH ₂ H 2-Et OCHEt HOS E7.39 F ₂ CH H 2-Et OCHEt HOS E7.40 F ₃ CH 2-Et OCHEt HOS E7.41 ClCH ₂ H 2-Et OCHEt HOS E7.42 Cl ₂ CH H 2-Et OCHEt HOS E7.43 Me H 3-Et OCHEt HOS E7.44 Me H 3-Et SCHEt HOS E7.45 Et H 3-Et OCHEt HOS E7 .46 nPr H 3-Et OCHEt HOS E7.47 iPr H 3-Et OCHEt HOS E7.48 nBu H 3-Et OCHEt HOS E 7.49 FCH ₂ H 3-Et OCHEt HOS E7.50 F ₂ CH H 3-Et OCHEt HOS E7.51 F ₃ CH 3-Et OCHEt HOS E7.52 ClCH ₂ H 3-Et OCHEt HOS E7.53 Cl ₂ CH H 3-Et OCHEt HOS E7.54 Me H 2,3-Me ₂ OCHEt HOS E7.55 Me H 2,3-Me ₂ SCHEt HOS E7.56 Et H 2,3-Me ₂ OCHEt HOS E7.57 nPr H 2 , 3-Me ₂ OCHEt HOS E7.58 iPr H 2,3-Me ₂ OCHEt HOS E7.59 nBu H 2,3-Me ₂ OCHEt HOS E7.60 FCH ₂ H 2,3-Me ₂ OCHEt HOS E7.61 F ₂ CH H 2,3-Me ₂ OCHEt HOS E7.62 F ₃ CH 2,3-Me ₂ OCHEt HOS E7.63 ClCH ₂ H 2,3-Me ₂ OCHEt HOS E7.64 Cl ₂ CH H 2,3 -Me ₂ OCHEt HOS E7.65 Me H 2-F OCHEt HOS E7.66 Me H 2-F SCHEt HOS E7.67 Et H 2-F OCHEt HOS E7.68 nPr H 2-F OCHEt HOS E7.69 iPr H 2-F OCHEt HOS E7.70 nBu H 2-F OCHEt HOS E7.71 FCH ₂ H 2-F OCHEt HOS E7.72 F ₂ CH H 2-F OCHEt HOS E7.73 F ₃ CH 2-F OCHEt HOS E7 .74 ClCH ₂ H 2-F OCHEt HOS E7.75 Cl ₂ CH H 2-F OCHEt HOS E7.76 Me H 3-F OCHEt HOS E7.77 Me H 3-F SCHEt HOS E7.78 Et H 3-F OCHEt HOS E7.79 nPr H 3-F OCHEt HOS E7.80 iPr H 3-F OCHEt HOS E7.81 nBu H 3-F OCHEt HOS E7.82 FCH ₂ H 3-F OCHEt HOS E7.83 F ₂ CH H 3-F OCHEt HOS E7.84 F ₃ CH 3-F OCHEt HOS E7.85 ClCH ₂ H 3-F OCHEt HOS E7.86 Cl ₂ CH H 3-F OCHEt HOS E7.87 Me H 2-Cl OCHEt HOS E7.88 Me H 2-Cl SCHEt HOS E7.89 Et H 2-Cl OCHEt HOS E7.90 nPr H 2-Cl OCHEt HOS E7.91 iPr H 2-Cl OCHEt HOS E7.92 nBu H 2-Cl OCHEt HOS E7.93 FCH ₂ H 2-Cl OCHEt HOS E7.94 F ₂ CH H 2-Cl OCHEt HOS E7.95 F ₃ CH 2-Cl OCHEt HOS E7.96 ClCH ₂ H 2-Cl OCHEt HOS E7.97 Cl ₂ CH H 2-Cl OCHEt HOS E7.98 Me H 3-Cl OCHEt HOS E7.99 Me H 3-Cl SCHEt HOS E7.100 Et H 3-Cl OCHEt HOS E7.101 nPr H 3-Cl OCHEt HOS E7.102 iPr H 3-Cl OCHEt HOS E7.103 nBu H 3-Cl OCHEt HOS E7.104 FCH ₂ H 3-Cl OCHEt HOS E7.105 F ₂ CH H 3-Cl OCHEt HOS E7.106 F ₃ CH 3-Cl OCHEt HOS E7.107 ClCH ₂ H 3-Cl OCHEt HOS E7.108 Cl ₂ CH H 3-Cl OCHEt HOS E7.109 Me H 2-OMe OCHEt HOS E7.110 Me H 2-OMe SCHEt HOS E7.111 Et H 2-OMe OCHEt HOS E7 .112 nPr H 2-OMe OCHEt HOS E7.113 iPr H 2-OMe OCHEt HOS E7.114 nBu H 2-OMe OCHEt HOS E7.115 FCH ₂ H 2-OMe OCHEt HOS E7.116 F ₂ CH H 2-OMe OCHEt HOS E7.117 F ₃ CH 2-OMe OCHEt HOS E7.118 ClCH ₂ H 2-OMe O CHEt HOS E7.119 Cl ₂ CH H 2-OMe OCHEt HOS E7.120 Me H 3-OMe OCHEt HOS E7.121 Me H 3-OMe SCHEt HOS E7.122 Et H 3-OMe OCHEt HOS E7.123 nPr H 3 -OMe OCHEt HOS E7.124 iPr H 3-OMe OCHEt HOS E7.125 nBu H 3-OMe OCHEt HOS E7.126 FCH ₂ H 3-OMe OCHEt HOS E7.127 F ₂ CH H 3-OMe OCHEt HOS E7.128 F ₃ CH 3-OMe OCHEt HOS E7.129 ClCH ₂ H 3-OMe OCHEt HOS E7.130 Cl ₂ CH H 3-OMe OCHEt HOS E7.131 Me HH OCHiPr HOS Oil E7.132 MeO HH OCHiPr HOS E7.133 Me HH OCHiPr HOO E7.134 MeO HH OCHiPr HOO E7.135 Me H 2-Me OCHiPr HOS Oil E7.136 MeO H 2-Me OCHiPr HOS E7.137 Me H 2-Me OCHiPr HOO E7.138 MeO H 2- Me OCHiPr HOO ────────────────────────────────────

【００５６】[0056]

【表６】 ──────────────────────────────────── 番号 R¹ R² (R³)n ACR⁴(R⁵) (R⁶)m X Q 融点（℃） ──────────────────────────────────── F1.1 Me H H OCH₂ 4-Me O S 154-156 F1.2 Me H H SCH₂ 4-Me O S F1.3 MeO H H OCH₂ 4-Me O S 147-150 F1.4 Me H H OCH₂ 4-Me O O F1.5 MeO H H OCH₂ 4-Me O O 95-96 F1.6 Et H H OCH₂ 4-Me O S F1.7 nPr H H OCH₂ 4-Me O S F1.8 iPr H H OCH₂ 4-Me O S F1.9 nBu H H OCH₂ 4-Me O S F1.10 F₃C H H OCH₂ 4-Me O S F1.11 Me H H OCH₂ 5-Me O S 211-213 F1.12 Me H H SCH₂ 5-Me O S F1.13 MeO H H OCH₂ 5-Me O S F1.14 Me H H OCH₂ 5-Me O O F1.15 MeO H H OCH₂ 5-Me O O 105-108 F1.16 Et H H OCH₂ 5-Me O S F1.17 nPr H H OCH₂ 5-Me O S F1.18 iPr H H OCH₂ 5-Me O S F1.19 nBu H H OCH₂ 5-Me O S F1.20 F₃C H H OCH₂ 5-Me O S F1.21 Me H H OCH₂ 6-Me O S 201-202 F1.22 Me H H SCH₂ 6-Me O S F1.23 MeO H H OCH₂ 6-Me O S F1.24 Me H H OCH₂ 6-Me O O F1.25 MeO H H OCH₂ 6-Me O O 102-104 F1.26 Et H H OCH₂ 6-Me O S F1.27 nPr H H OCH₂ 6-Me O S F1.28 iPr H H OCH₂ 6-Me O S F1.29 nBu H H OCH₂ 6-Me O S F1.30 F₃C H H OCH₂ 6-Me O S F1.31 Me H H OCH₂ 7-Me O S 164-166 F1.32 Me H H SCH₂ 7-Me O S F1.33 MeO H H OCH₂ 7-Me O S 150-151 F1.34 Me H H OCH₂ 7-Me O S F1.35 MeO H H OCH₂ 7-Me O O F1.36 Et H H OCH₂ 7-Me O S F1.37 nPr H H OCH₂ 7-Me O S F1.38 iPr H H OCH₂ 7-Me O S F1.39 nBu H H OCH₂ 7-Me O S F1.40 F₃C H H OCH₂ 7-Me O S F1.41 Me H H OCH₂ 4-Et O S F1.42 Me H H SCH₂ 4-Et O S F1.43 Et H H OCH₂ 4-Et O S F1.44 nPr H H OCH₂ 4-Et O S F1.45 iPr H H OCH₂ 4-Et O S F1.46 nBu H H OCH₂ 4-Et O S F1.47 F₃C H H OCH₂ 4-Et O S F1.48 Me H H OCH₂ 5-Et O S F1.49 Me H H SCH₂ 5-Et O S F1.50 Et H H OCH₂ 5-Et O S F1.51 nPr H H OCH₂ 5-Et O S F1.52 iPr H H OCH₂ 5-Et O S F1.53 nBu H H OCH₂ 5-Et O S F1.54 F₃C H H OCH₂ 5-Et O S F1.55 Me H H OCH₂ 6-Et O S F1.56 Me H H SCH₂ 6-Et O S F1.57 Et H H OCH₂ 6-Et O S F1.58 nPr H H OCH₂ 6-Et O S F1.59 iPr H H OCH₂ 6-Et O S F1.60 nBu H H OCH₂ 6-Et O S F1.61 F₃C H H OCH₂ 6-Et O S F1.62 Me H H OCH₂ 7-Et O S F1.63 Me H H SCH₂ 7-Et O S F1.64 Et H H OCH₂ 7-Et O S F1.65 nPr H H OCH₂ 7-Et O S F1.66 iPr H H OCH₂ 7-Et O S F1.67 nBu H H OCH₂ 7-Et O S F1.68 F₃C H H OCH₂ 7-Et O S F1.69 MeO H H OCH₂ 5-NO₂ O O 184-187 F2.1 Me H H OCH₂ 4-CH₂CH=CH₂ O S F2.2 Et H H OCH₂ 4-CH₂CH=CH₂ O S F2.3 nPr H H OCH₂ 4-CH₂CH=CH₂ O S F2.4 iPr H H OCH₂ 4-CH₂CH=CH₂ O S F2.5 nBu H H OCH₂ 4-CH₂CH=CH₂ O S F2.6 F₃C H H OCH₂ 4-CH₂CH=CH₂ O S F2.7 Me H H OCH₂ 5-CH₂CH=CH₂ O S F2.8 MeO H H OCH₂ 5-CH₂CH=CH₂ O S F2.9 Me H H OCH₂ 5-CH₂CH=CH₂ O O F2.10 MeO H H OCH₂ 5-CH₂CH=CH₂ O O F2.11 Et H H OCH₂ 5-CH₂CH=CH₂ O S F2.12 nPr H H OCH₂ 5-CH₂CH=CH₂ O S F2.13 iPr H H OCH₂ 5-CH₂CH=CH₂ O S F2.14 nBu H H OCH₂ 5-CH₂CH=CH₂ O S F2.15 F₃C H H OCH₂ 5-CH₂CH=CH₂ O S F2.16 Me H H OCH₂ 6-CH₂CH=CH₂ O S F2.17 MeO H H OCH₂ 6-CH₂CH=CH₂ O S F2.18 Et H H OCH₂ 6-CH₂CH=CH₂ O S F2.19 nPr H H OCH₂ 6-CH₂CH=CH₂ O S F2.20 iPr H H OCH₂ 6-CH₂CH=CH₂ O S F2.21 nBu H H OCH₂ 6-CH₂CH=CH₂ O S F2.22 F₃C H H OCH₂ 6-CH₂CH=CH₂ O S F2.23 Me H H OCH₂ 7-CH₂CH=CH₂ O S F2.24 Et H H OCH₂ 7-CH₂CH=CH₂ O S F2.25 nPr H H OCH₂ 7-CH₂CH=CH₂ O S F2.26 iPr H H OCH₂ 7-CH₂CH=CH₂ O S F2.27 nBu H H OCH₂ 7-CH₂CH=CH₂ O S F2.28 F₃C H H OCH₂ 7-CH₂CH=CH₂ O S F2.29 Me H H OCH₂ 5-CH₂C≡CH O S F2.30 MeO H H OCH₂ 5-CH₂C≡CH O S F2.31 Me H H OCH₂ 5-CH₂C≡CH O O F2.32 MeO H H OCH₂ 5-CH₂C≡CH O O F2.33 Me H H OCH₂ 6-CH₂C≡CH O S F2.34 MeO H H OCH₂ 6-CH₂C≡CH O S F3.1 Me H H OCH₂ 4-OMe O S 147-148 F3.2 Me H H SCH₂ 4-OMe O S F3.3 MeO H H OCH₂ 4-OMe O S 117-120 F3.4 MeO H H OCH₂ 4-OMe O O F3.5 Et H H OCH₂ 4-OMe O S F3.6 nPr H H OCH₂ 4-OMe O S F3.7 iPr H H OCH₂ 4-OMe O S F3.8 nBu H H OCH₂ 4-OMe O S F3.9 F₃C H H OCH₂ 4-OMe O S F3.10 Me H H OCH₂ 5-OMe O S 217-219 F3.11 Me H H SCH₂ 5-OMe O S F3.12 MeO H H OCH₂ 5-OMe O S F3.13 Me H H OCH₂ 5-OMe O O F3.14 MeO H H OCH₂ 5-OMe O O 134-137 F3.15 Et H H OCH₂ 5-OMe O S F3.16 nPr H H OCH₂ 5-OMe O S F3.17 iPr H H OCH₂ 5-OMe O S F3.18 nBu H H OCH₂ 5-OMe O S F3.19 F₃C H H OCH₂ 5-OMe O S F3.20 Me H H OCH₂ 6-OMe O S 145-147 F3.21 Me H H SCH₂ 6-OMe O S 124-125 F3.22 MeO H H OCH₂ 6-OMe O S 118-120 F3.23 MeO H H OCH₂ 6-OMe O O F3.24 Et H H OCH₂ 6-OMe O S F3.25 nPr H H OCH₂ 6-OMe O S F3.26 iPr H H OCH₂ 6-OMe O S F3.27 nBu H H OCH₂ 6-OMe O S F3.28 F₃C H H OCH₂ 6-OMe O S F3.29 Me H H OCH₂ 7-OMe O S 163-164 F3.30 Me H H SCH₂ 7-OMe O S F3.31 MeO H H OCH₂ 7-OMe O S 174-176 F3.32 MeO H H OCH₂ 7-OMe O O F3.33 Et H H OCH₂ 7-OMe O S F3.34 nPr H H OCH₂ 7-OMe O S F3.35 iPr H H OCH₂ 7-OMe O S F3.36 nBu H H OCH₂ 7-OMe O S F3.37 F₃C H H OCH₂ 7-OMe O S F3.38 Me H H OCH₂ 4-OEt O S F3.39 Me H H SCH₂ 4-OEt O S F3.40 Et H H OCH₂ 4-OEt O S F3.41 nPr H H OCH₂ 4-OEt O S F3.42 iPr H H OCH₂ 4-OEt O S F3.43 nBu H H OCH₂ 4-OEt O S F3.45 F₃C H H OCH₂ 4-OEt O S F3.46 Me H H OCH₂ 5-OEt O S F3.47 Me H H SCH₂ 5-OEt O S F3.48 MeO H H OCH₂ 5-OEt O S F3.49 Me H H OCH₂ 5-OEt O O F3.50 MeO H H OCH₂ 5-OEt O O F3.51 Et H H OCH₂ 5-OEt O S F3.53 iPr H H OCH₂ 5-OEt O S F3.54 nBu H H OCH₂ 5-OEt O S F3.55 F₃C H H OCH₂ 5-OEt O S F3.56 Me H H OCH₂ 6-OEt O S 139-141 F3.57 Me H H SCH₂ 6-OEt O S F3.58 MeO H H OCH₂ 6-OEt O S F3.59 Me H H OCH₂ 6-OEt O O F3.60 MeO H H OCH₂ 6-OEt O O F3.61 Et H H OCH₂ 6-OEt O S F3.62 nPr H H OCH₂ 6-OEt O S F3.63 iPr H H OCH₂ 6-OEt O S F3.64 nBu H H OCH₂ 6-OEt O S F3.65 F₃C H H OCH₂ 6-OEt O S F3.66 Me H H OCH₂ 7-OEt O S F3.67 Me H H SCH₂ 7-OEt O S F3.68 Et H H OCH₂ 7-OEt O S F3.69 nPr H H OCH₂ 7-OEt O S F3.70 iPr H H OCH₂ 7-OEt O S F3.71 nBu H H OCH₂ 7-OEt O S F3.72 F₃C H H OCH₂ 7-OEt O S F4.1 Me H H OCH₂ 4-F O S 156-158 F4.2 Me H H SCH₂ 4-F O S F4.3 MeO H H OCH₂ 4-F O S F4.4 Me H H OCH₂ 4-F O O F4.5 MeO H H OCH₂ 4-F O O F4.6 Et H H OCH₂ 4-F O S F4.7 nPr H H OCH₂ 4-F O S F4.8 iPr H H OCH₂ 4-F O S F4.9 nBu H H OCH₂ 4-F O S F4.10 F₃C H H OCH₂ 4-F O S F4.11 Me H H OCH₂ 5-F O S 201 F4.12 MeO H H OCH₂ 5-F O S 174-176 F4.13 Me H H OCH₂ 5-F O O F4.14 MeO H H OCH₂ 5-F O O 133-134 F4.15 MeO H H SCH₂ 5-F O O F4.16 Me H H SCH₂ 5-F O S 108-109 F4.17 MeO H H SCH₂ 5-F O S F4.18 Et H H OCH₂ 5-F O S F4.19 nPr H H OCH₂ 5-F O S 201-202 F4.20 nBu H H OCH₂ 5-F O S 189-191 F4.21 iPr H H OCH₂ 5-F O S F4.22 c-Hex H H OCH₂ 5-F O S 211-212 F4.23 FCH₂ H H OCH₂ 5-F O S 192-193 F4.24 FCH₂ H H OCH₂ 5-F O O F4.25 ClCH₂ H H OCH₂ 5-F O S 198-200 F4.26 ClCH₂ H H OCH₂ 5-F O O F4.27 Cl₂CH H H OCH₂ 5-F O S 208-209 F4.28 F₃C H H OCH₂ 5-F O S 204-206 F4.29 F₃C H H OCH₂ 5-F O O F4.30 Me H H OCH₂ 6-F O S 204-205 F4.31 MeO H H OCH₂ 6-F O S F4.32 Me H H OCH₂ 6-F O O F4.33 MeO H H OCH₂ 6-F O O 120-122 F4.34 Me H H SCH₂ 6-F O S F4.35 Et H H OCH₂ 6-F O S F4.36 nPr H H OCH₂ 6-F O S F4.37 iPr H H OCH₂ 6-F O S F4.38 nBu H H OCH₂ 6-F O S F4.39 F₃C H H OCH₂ 6-F O S F4.40 Me H H OCH₂ 7-F O S 149-152 F4.41 MeO H H OCH₂ 7-F O S 136-139 F4.42 Me H H OCH₂ 7-F O O F4.43 MeO H H OCH₂ 7-F O O 120-123 F4.44 Me H H SCH₂ 7-F O S F4.45 Et H H OCH₂ 7-F O S F4.46 nPr H H OCH₂ 7-F O S F4.47 iPr H H OCH₂ 7-F O S F4.48 nBu H H OCH₂ 7-F O S F4.49 F₃C H H OCH₂ 7-F O S F4.50 Me H H OCH₂ 4-Cl O S F4.51 Me H H SCH₂ 4-Cl O S F4.52 MeO H H OCH₂ 4-Cl O S F4.53 MeO H H OCH₂ 4-Cl O O F4.54 Et H H OCH₂ 4-Cl O S F4.55 nPr H H OCH₂ 4-Cl O S F4.56 iPr H H OCH₂ 4-Cl O S F4.57 nBu H H OCH₂ 4-Cl O S F4.58 F₃C H H OCH₂ 4-Cl O S F4.59 Me H H OCH₂ 5-Cl O S 230-232 F4.60 Me H H SCH₂ 5-Cl O S F4.61 MeO H H OCH₂ 5-Cl O S 211-213 F4.62 Me H H OCH₂ 5-Cl O O F4.63 MeO H H OCH₂ 5-Cl O O 157-160 F4.64 Et H H OCH₂ 5-Cl O S F4.65 nPr H H OCH₂ 5-Cl O S F4.66 iPr H H OCH₂ 5-Cl O S F4.67 nBu H H OCH₂ 5-Cl O S F4.68 F₃C H H OCH₂ 5-Cl O S F4.69 Me H H OCH₂ 6-Cl O S 218 F4.70 Me H H SCH₂ 6-Cl O S F4.71 MeO H H OCH₂ 6-Cl O S 195-197 F4.72 Me H H OCH₂ 6-Cl O O F4.73 MeO H H OCH₂ 6-Cl O O F4.74 Et H H OCH₂ 6-Cl O S F4.75 nPr H H OCH₂ 6-Cl O S F4.76 iPr H H OCH₂ 6-Cl O S F4.77 nBu H H OCH₂ 6-Cl O S F4.78 F₃C H H OCH₂ 6-Cl O S F4.79 Me H H OCH₂ 7-Cl O S 172-175 F4.80 Me H H SCH₂ 7-Cl O S F4.81 MeO H H OCH₂ 7-Cl O S 159-162 F4.82 Et H H OCH₂ 7-Cl O S F4.83 nPr H H OCH₂ 7-Cl O S F4.84 iPr H H OCH₂ 7-Cl O S F4.85 nBu H H OCH₂ 7-Cl O S F4.86 F₃C H H OCH₂ 7-Cl O S F4.87 Me H H OCH₂ 4-Br O S F4.88 Me H H SCH₂ 4-Br O S F4.89 MeO H H OCH₂ 4-Br O S F4.90 Et H H OCH₂ 4-Br O S F4.91 nPr H H OCH₂ 4-Br O S F4.92 iPr H H OCH₂ 4-Br O S F4.93 nBu H H OCH₂ 4-Br O S F4.94 F₃C H H OCH₂ 4-Br O S F4.95 Me H H OCH₂ 5-Br O S F4.96 Me H H SCH₂ 5-Br O S F4.97 MeO H H OCH₂ 5-Br O S F4.98 Et H H OCH₂ 5-Br O S F4.99 nPr H H OCH₂ 5-Br O S F4.100 iPr H H OCH₂ 5-Br O S F4.101 nBu H H OCH₂ 5-Br O S F4.102 F₃C H H OCH₂ 5-Br O S F4.103 Me H H OCH₂ 6-Br O S 218-221 F4.104 Me H H SCH₂ 6-Br O S F4.105 MeO H H OCH₂ 6-Br O S F4.106 Me H H OCH₂ 6-Br O O F4.107 MeO H H OCH₂ 6-Br O O F4.108 Et H H OCH₂ 6-Br O S F4.109 nPr H H OCH₂ 6-Br O S F4.110 iPr H H OCH₂ 6-Br O S F4.111 nBu H H OCH₂ 6-Br O S F4.112 F₃C H H OCH₂ 6-Br O S F4.113 Me H H OCH₂ 7-Br O S F4.114 Me H H SCH₂ 7-Br O S F4.115 MeO H H OCH₂ 7-Br O S F4.116 Et H H OCH₂ 7-Br O S F4.117 nPr H H OCH₂ 7-Br O S F4.118 iPr H H OCH₂ 7-Br O S F4.119 nBu H H OCH₂ 7-Br O S F4.120 F₃C H H OCH₂ 7-Br O S F5.1 Me H H OCH₂ 4-CF₃ O S F5.2 Me H H SCH₂ 4-CF₃ O S F5.3 MeO H H OCH₂ 4-CF₃ O S 179-180 F5.4 Et H H OCH₂ 4-CF₃ O S F5.6 iPr H H OCH₂ 4-CF₃ O S F5.7 nBu H H OCH₂ 4-CF₃ O S F5.8 F₃C H H OCH₂ 4-CF₃ O S F5.9 Me H H OCH₂ 5-CF₃ O S 208-210 F5.10 Me H H SCH₂ 5-CF₃ O S F5.11 MeO H H OCH₂ 5-CF₃ O S F5.12 Me H H OCH₂ 5-CF₃ O O F5.13 MeO H H OCH₂ 5-CF₃ O O 145-148 F5.14 Et H H OCH₂ 5-CF₃ O S F5.15 nPr H H OCH₂ 5-CF₃ O S F5.16 iPr H H OCH₂ 5-CF₃ O S F5.17 nBu H H OCH₂ 5-CF₃ O S F5.18 F₃C H H OCH₂ 5-CF₃ O S F5.19 Me H H OCH₂ 6-CF₃ O S F5.20 Me H H SCH₂ 6-CF₃ O S F5.21 MeO H H OCH₂ 6-CF₃ O S F5.22 Me H H OCH₂ 6-CF₃ O O F5.23 MeO H H OCH₂ 6-CF₃ O O F5.24 Et H H OCH₂ 6-CF₃ O S F5.25 nPr H H OCH₂ 6-CF₃ O S F5.26 iPr H H OCH₂ 6-CF₃ O S F5.27 nBu H H OCH₂ 6-CF₃ O S F5.28 F₃C H H OCH₂ 6-CF₃ O S F5.29 Me H H OCH₂ 7-CF₃ O S F5.30 Me H H SCH₂ 7-CF₃ O S F5.31 MeO H H OCH₂ 7-CF₃ O S F5.32 Et H H OCH₂ 7-CF₃ O S F5.34 nPr H H OCH₂ 7-CF₃ O S F5.36 nBu H H OCH₂ 7-CF₃ O S F5.37 F₃C H H OCH₂ 7-CF₃ O S F5.38 Me H H OCH₂ 4-OCF₃ O S F5.39 Me H H SCH₂ 4-OCF₃ O S F5.40 Et H H OCH₂ 4-OCF₃ O S F5.41 nPr H H OCH₂ 4-OCF₃ O S F5.42 iPr H H OCH₂ 4-OCF₃ O S F5.43 nBu H H OCH₂ 4-OCF₃ O S F5.44 F₃C H H OCH₂ 4-OCF₃ O S F5.45 Me H H OCH₂ 5-OCF₃ O S F5.46 Me H H SCH₂ 5-OCF₃ O S F5.47 MeO H H OCH₂ 5-OCF₃ O S F5.48 Me H H OCH₂ 5-OCF₃ O O F5.49 MeO H H OCH₂ 5-OCF₃ O O F5.50 Et H H OCH₂ 5-OCF₃ O S F5.51 nPr H H OCH₂ 5-OCF₃ O S F5.52 iPr H H OCH₂ 5-OCF₃ O S F5.53 nBu H H OCH₂ 5-OCF₃ O S F5.54 F₃C H H OCH₂ 5-OCF₃ O S F5.56 Me H H OCH₂ 6-OCF₃ O S F5.57 Me H H SCH₂ 6-OCF₃ O S F5.58 MeO H H OCH₂ 6-OCF₃ O S F5.59 Et H H OCH₂ 6-OCF₃ O S F5.60 nPr H H OCH₂ 6-OCF₃ O S F5.61 iPr H H OCH₂ 6-OCF₃ O S F5.62 nBu H H OCH₂ 6-OCF₃ O S F5.63 F₃C H H OCH₂ 6-OCF₃ O S F5.64 Me H H OCH₂ 7-OCF₃ O S F5.65 Me H H SCH₂ 7-OCF₃ O S F5.66 Et H H OCH₂ 7-OCF₃ O S F5.67 nPr H H OCH₂ 7-OCF₃ O S F5.68 iPr H H OCH₂ 7-OCF₃ O S F5.69 nBu H H OCH₂ 7-OCF₃ O S F5.70 F₃C H H OCH₂ 7-OCF₃ O S F6.1 Me H H OCH₂ 5-CHO O S F6.2 MeO H H OCH₂ 5-CHO O S F6.3 Me H H OCH₂ 6-CHO O S F6.4 MeO H H OCH₂ 6-CHO O S F6.5 Me H H OCH₂ 5-COMe O S F6.6 MeO H H OCH₂ 5-COMe O S F6.7 Me H H OCH₂ 6-COMe O S F6.8 MeO H H OCH₂ 6-COMe O S F6.9 Me H H OCH₂ 4-COOMe O S F6.10 MeO H H OCH₂ 4-COOMe O S F6.11 Me H H OCH₂ 4-COOMe O O 158-160 F6.12 MeO H H OCH₂ 4-COOMe O O 粘土状 F6.13 Me H H OCH₂ 5-COOMe O S F6.14 MeO H H OCH₂ 5-COOMe O S F6.15 Me H H OCH₂ 5-COOMe O O 165-168 F6.16 MeO H H OCH₂ 5-COOMe O O 163-167 F6.17 Me H H OCH₂ 6-COOMe O S F6.18 MeO H H OCH₂ 6-COOMe O S F6.19 Me H H OCH₂ 6-COOMe O O 155-158 F6.20 MeO H H OCH₂ 6-COOMe O O 〜230 F6.21 Me H H OCH₂ 7-COOMe O S F6.22 MeO H H OCH₂ 7-COOMe O S F6.23 Me H H OCH₂ 7-COOMe O O 102-105 F6.24 MeO H H OCH₂ 7-COOMe O O 142-146 F7.1 Me H H OCH₂ 4,5-Me₂ O S F7.2 Me H H SCH₂ 4,5-Me₂ O S F7.3 MeO H H OCH₂ 4,5-Me₂ O S F7.4 Me H H OCH₂ 4,6-Me₂ O S F7.5 Me H H SCH₂ 4,6-Me₂ O S F7.6 MeO H H OCH₂ 4,6-Me₂ O S F7.7 Me H H OCH₂ 4,6-Me₂ O O F7.8 MeO H H OCH₂ 4,6-Me₂ O O F7.9 Me H H OCH₂ 4,7-Me₂ O S F7.10 Me H H SCH₂ 4,7-Me₂ O S F7.11 Me H H OCH₂ 5,6-Me₂ O S F7.12 Me H H SCH₂ 5,6-Me₂ O S F7.13 Me H H OCH₂ 5,7-Me₂ O S F7.14 Me H H SCH₂ 5,7-Me₂ O S F7.15 MeO H H OCH₂ 5,7-Me₂ O S F7.16 Me H H OCH₂ 5,7-Me₂ O O F7.17 MeO H H OCH₂ 5,7-Me₂ O O 157-159 F7.18 Me H H OCH₂ 6,7-Me₂ O S F7.19 Me H H SCH₂ 6,7-Me₂ O S F7.20 MeO H H OCH₂ 6,7-Me₂ O S F7.21 Me H H OCH₂ 4,5-(OMe)₂ O S F7.22 Me H H SCH₂ 4,5-(OMe)₂ O S F7.23 Me H H OCH₂ 4,6-(OMe)₂ O S F7.24 Me H H SCH₂ 4,6-(OMe)₂ O S F7.25 Me H H OCH₂ 4,7-(OMe)₂ O S F7.26 Me H H SCH₂ 4,7-(OMe)₂ O S F7.27 Me H H OCH₂ 5,6-(OMe)₂ O S F7.28 Me H H SCH₂ 5,6-(OMe)₂ O S F7.29 MeO H H OCH₂ 5,6-(OMe)₂ O S F7.30 Me H H OCH₂ 5,7-(OMe)₂ O S F7.31 Me H H SCH₂ 5,7-(OMe)₂ O S F7.32 Me H H OCH₂ 6,7-(OMe)₂ O S F7.33 Me H H SCH₂ 6,7-(OMe)₂ O S F7.34 Me H H OCH₂ 4,5-F₂ O S 178-180 F7.35 Me H H SCH₂ 4,5-F₂ O S F7.36 MeO H H OCH₂ 4,5-F₂ O S F7.37 Me H H OCH₂ 4,5-F₂ O O F7.38 MeO H H OCH₂ 4,5-F₂ O O F7.39 Me H H OCH₂ 4,6-F₂ O S 198-200 F7.40 Me H H SCH₂ 4,6-F₂ O S F7.41 MeO H H OCH₂ 4,6-F₂ O S F7.42 Me H H OCH₂ 4,7-F₂ O S F7.43 Me H H SCH₂ 4,7-F₂ O S F7.44 MeO H H OCH₂ 4,7-F₂ O S F7.45 Me H H OCH₂ 5,6-F₂ O S 212-214 F7.46 Me H H SCH₂ 5,6-F₂ O S F7.47 MeO H H OCH₂ 5,6-F₂ O S F7.48 Me H H OCH₂ 5,6-F₂ O O F7.49 MeO H H OCH₂ 5,6-F₂ O O F7.50 Me H H OCH₂ 5,7-F₂ O S F7.52 Me H H SCH₂ 5,7-F₂ O S F7.53 MeO H H OCH₂ 5,7-F₂ O S F7.54 Me H H OCH₂ 6,7-F₂ O S F7.55 Me H H SCH₂ 6,7-F₂ O S F7.56 MeO H H OCH₂ 6,7-F₂ O O 145-148 F7.57 Me H H OCH₂ 4,5-Cl₂ O S F7.58 Me H H SCH₂ 4,5-Cl₂ O S F7.59 Me H H OCH₂ 4,6-Cl₂ O S F7.60 Me H H SCH₂ 4,6-Cl₂ O S F7.61 Me H H OCH₂ 4,7-Cl₂ O S F7.62 Me H H SCH₂ 4,7-Cl₂ O S F7.63 Me H H OCH₂ 5,6-Cl₂ O S F7.64 Me H H SCH₂ 5,6-Cl₂ O S F7.65 Me H H OCH₂ 5,7-Cl₂ O S F7.66 Me H H SCH₂ 5,7-Cl₂ O S F7.67 MeO H H OCH₂ 5,7-Cl₂ O S F7.68 Me H H OCH₂ 5,7-Cl₂ O O F7.69 MeO H H OCH₂ 5,7-Cl₂ O O 135-136 F7.70 Me H H OCH₂ 6,7-Cl₂ O S F7.71 Me H H SCH₂ 6,7-Cl₂ O S F7.72 Me H H OCH₂ 4,5-(CF₃)₂ O S F7.73 Me H H SCH₂ 4,5-(CF₃)₂ O S F7.74 Me H H OCH₂ 4,6-(CF₃)₂ O S F7.75 Me H H SCH₂ 4,6-(CF₃)₂ O S F7.76 Me H H OCH₂ 4,7-(CF₃)₂ O S F7.77 Me H H SCH₂ 4,7-(CF₃)₂ O S F7.78 Me H H OCH₂ 5,6-(CF₃)₂ O S F7.79 Me H H SCH₂ 5,6-(CF₃)₂ O S F7.80 Me H H OCH₂ 5,7-(CF₃)₂ O S F7.81 Me H H SCH₂ 5,7-(CF₃)₂ O S F7.82 Me H H OCH₂ 6,7-(CF₃)₂ O S F7.83 Me H H SCH₂ 6,7-(CF₃)₂ O S F7.84 Me H H OCH₂ 4-F,5-Me O S F7.85 Me H H SCH₂ 4-F,5-Me O S F7.86 Me H H OCH₂ 4-F,6-Me O S F7.87 Me H H SCH₂ 4-F,6-Me O S F7.88 Me H H OCH₂ 4-F,7-Me O S F7.89 Me H H SCH₂ 4-F,7-Me O S F7.90 Me H H OCH₂ 4-Me,5-F O S F7.91 Me H H SCH₂ 4-Me,5-F O S F7.92 Me H H OCH₂ 5-F,6-Me O S 231-234 F7.93 Me H H SCH₂ 5-F,6-Me O S F7.94 Me H H OCH₂ 5-F,7-Me O S F7.95 Me H H SCH₂ 5-F,7-Me O S F7.96 MeO H H OCH₂ 5-F,7-Me O S F7.97 Me H H OCH₂ 4-Me,6-F O S F7.98 Me H H SCH₂ 4-Me,6-F O S F7.99 Me H H OCH₂ 5-Me,6-F O S 231-234 F7.100 Me H H SCH₂ 5-Me,6-F O S F7.101 MeO H H OCH₂ 6-F,5-Me O S F7.102 Me H H OCH₂ 6-F,7-Me O S F7.103 Me H H SCH₂ 6-F,7-Me O S F7.104 Me H H OCH₂ 4-Me,7-F O S F7.105 Me H H SCH₂ 4-Me,7-F O S F7.106 Me H H OCH₂ 5-Me,7-F O S F7.107 Me H H SCH₂ 5-Me,7-F O S F7.108 Me H H OCH₂ 6-Me,7-F O S F7.109 Me H H SCH₂ 6-Me,7-F O S F7.110 Me H H OCH₂ 4-Cl,5-Me O S F7.111 Me H H SCH₂ 4-Cl,5-Me O S F7.112 MeO H H OCH₂ 4-Cl,5-Me O S F7.113 Me H H OCH₂ 4-Cl,6-Me O S F7.114 Me H H SCH₂ 4-Cl,6-Me O S F7.115 MeO H H OCH₂ 4-Cl,6-Me O S F7.116 Me H H OCH₂ 4-Cl,7-Me O S F7.117 Me H H SCH₂ 4-Cl,7-Me O S F7.118 Me H H OCH₂ 4-Me,5-Cl O S F7.119 Me H H SCH₂ 4-Me,5-Cl O S F7.120 Me H H OCH₂ 5-Cl,6-Me O S 236-239 F7.121 Me H H SCH₂ 5-Cl,6-Me O S F7.122 Me H H OCH₂ 5-Cl,7-Me O S F7.123 Me H H SCH₂ 5-Cl,7-Me O S F7.124 Me H H OCH₂ 4-Me,6-Cl O S F7.125 Me H H SCH₂ 4-Me,6-Cl O S F7.126 Me H H OCH₂ 5-Me,6-Cl O S F7.127 Me H H SCH₂ 5-Me,6-Cl O S F7.128 Me H H OCH₂ 7-Me,6-Cl O S F7.129 Me H H SCH₂ 7-Me,6-Cl O S F7.130 Me H H OCH₂ 4-Me,7-Cl O S F7.131 Me H H SCH₂ 4-Me,7-Cl O S F7.132 Me H H OCH₂ 5-Me,7-Cl O S F7.133 Me H H SCH₂ 5-Me,7-Cl O S F7.134 Me H H OCH₂ 6-Me,7-Cl O S F7.135 Me H H SCH₂ 6-Me,7-Cl O S F7.136 Me H H OCH₂ 4-Cl,5-OMe O S 193-195 F7.137 Me H H SCH₂ 4-Cl,5-OMe O S F7.138 MeO H H OCH₂ 4-Cl,5-OMe O S F7.139 Me H H OCH₂ 4-Cl,5-OMe O O F7.140 MeO H H OCH₂ 4-Cl,5-OMe O O F7.141 Me H H OCH₂ 4-Cl,6-OMe O S F7.142 Me H H SCH₂ 4-Cl,6-OMe O S F7.144 Me H H OCH₂ 4-Cl,7-OMe O S F7.144 Me H H SCH₂ 4-Cl,7-OMe O S F7.145 Me H H OCH₂ 4-OMe,5-Cl O S F7.146 Me H H SCH₂ 4-OMe,5-Cl O S F7.147 Me H H OCH₂ 5-Cl,6-OMe O S 222-225 F7.148 Me H H SCH₂ 5-Cl,6-OMe O S F7.149 MeO H H OCH₂ 5-Cl,6-OMe O S F7.150 MeO H H OCH₂ 5-Cl,6-OMe O O F7.151 Me H H OCH₂ 5-Cl,7-OMe O S F7.152 Me H H SCH₂ 5-Cl,7-OMe O S F7.153 Me H H OCH₂ 4-OMe,6-Cl O S F7.154 Me H H SCH₂ 4-OMe,6-Cl O S F7.155 Me H H OCH₂ 5-OMe,6-Cl O S F7.156 Me H H SCH₂ 5-OMe,6-Cl O S F7.157 Me H H OCH₂ 6-Cl,7-OMe O S F7.158 Me H H SCH₂ 6-Cl,7-OMe O S F7.159 Me H H OCH₂ 4-OMe,7-Cl O S F7.160 Me H H SCH₂ 4-OMe,7-Cl O S F7.161 Me H H OCH₂ 5-OMe,7-Cl O S F7.162 Me H H SCH₂ 5-OMe,7-Cl O S F7.163 Me H H OCH₂ 6-OMe,7-Cl O S F7.164 Me H H SCH₂ 6-OMe,7-Cl O S F7.165 Me H H OCH₂ 4-Cl,5-F O S F7.166 Me H H OCH₂ 4-Cl,6-F O S F7.167 Me H H OCH₂ 4-Cl,7-F O S F7.168 Me H H OCH₂ 4-F,5-Cl O S F7.169 Me H H OCH₂ 5-Cl,6-F O S 227-229 F7.170 MeO H H OCH₂ 5-Cl,6-F O S F7.171 Me H H OCH₂ 5-Cl,6-F O O F7.172 MeO H H OCH₂ 5-Cl,6-F O O F7.173 Me H H OCH₂ 6-F,7-Cl O S 182-185 F7.174 MeO H H OCH₂ 6-F,7-Cl O S F7.175 Me H H OCH₂ 5-Cl,7-F O S F7.176 Me H H OCH₂ 4-F,6-Cl O S F7.177 Me H H OCH₂ 5-F,6-Cl O S F7.178 Me H H OCH₂ 6-Cl,7-F O S F7.179 Me H H OCH₂ 4-F,7-Cl O S F7.180 Me H H OCH₂ 5-F,7-Cl O S ────────────────────────────────────[Table 6] 番号 Number R ¹ R ² (R ³ ) n ACR ⁴ (R ⁵ ) (R ⁶ ) m XQ Melting point (℃) ────────────────────────────────── _{── F1.1 Me HH OCH 2 4-} Me OS 154-156 F1.2 Me HH SCH 2 4-Me OS F1.3 MeO HH OCH 2 4-Me OS 147-150 F1.4 Me HH OCH 2 4- _{Me OO F1.5 MeO HH OCH 2 4} -Me OO 95-96 F1.6 Et HH OCH 2 4-Me OS F1.7 nPr HH OCH 2 4-Me OS F1.8 iPr HH OCH 2 4-Me OS F1 _{.9 nBu HH OCH 2 4-Me} OS F1.10 F 3 CHH OCH 2 4-Me OS F1.11 Me HH OCH 2 5-Me OS 211-213 F1.12 Me HH SCH 2 5-Me OS F1.13 MeO HH OCH ₂ 5-Me OS F1.14 Me HH OCH ₂ 5-Me OO F1.15 MeO HH OCH ₂ 5-Me OO 105-108 F1.16 Et HH OCH ₂ 5-Me OS F1.17 nPr HH OCH _{2 5-Me OS F1.18 iPr HH} OCH 2 5-Me OS F1.19 nBu HH OCH 2 5-Me OS F1.20 F 3 CHH OCH 2 5-Me OS F1.21 Me HH OCH 2 6-Me OS _{201-202 F1.22 Me HH SCH 2 6-} Me OS F1.23 MeO HH OCH 2 6-Me OS F1.24 Me HH OCH 2 6-Me OO F1.25 MeO HH OCH 2 6-Me OO 102 _{-104 F1.26 Et HH OCH 2 6-} Me OS F1.27 nPr HH OCH 2 6-Me OS F1.28 iPr HH OCH 2 6-Me OS F1.29 nBu HH OCH 2 6-Me OS F1.30 F _{_{3 CHH OCH 2 6-Me OS}} F1.31 Me HH OCH 2 7-Me OS 164-166 F1.32 Me HH SCH 2 7-Me OS F1.33 MeO HH OCH 2 7-Me OS 150-151 F1.34 _{Me HH OCH 2 7-Me OS} F1.35 MeO HH OCH 2 7-Me OO F1.36 Et HH OCH 2 7-Me OS F1.37 nPr HH OCH 2 7-Me OS F1.38 iPr HH OCH 2 7- _{Me OS F1.39 nBu HH OCH 2 7} -Me OS F1.40 F 3 CHH OCH 2 7-Me OS F1.41 Me HH OCH 2 4-Et OS F1.42 Me HH SCH 2 4-Et OS F1.43 Et HH OCH ₂ 4-Et OS F1.44 nPr HH OCH ₂ 4-Et OS F1.45 iPr HH OCH ₂ 4-Et OS F1.46 nBu HH OCH ₂ 4-Et OS F1.47 F ₃ CHH OCH ₂ 4 -Et OS F1.48 Me HH OCH ₂ 5-Et OS F1.49 Me HH SCH ₂ 5-Et OS F1.50 Et HH OCH ₂ 5-Et OS F1.51 nPr HH OCH ₂ 5-Et OS F1.52 _{iPr HH OCH 2 5-Et OS} F1.53 nBu HH OCH 2 5-Et OS F1.54 F 3 CHH OCH 2 5-Et OS F1.55 Me HH OCH 2 6-Et OS F1.56 Me HH SCH 2 6 _{-Et OS F1.57 Et HH OCH 2 6} -Et OS F1.58 nPr HH OCH 2 6-Et OS F1.59 iPr HH OCH 2 6-Et OS F1.60 nBu HH OCH 2 6-Et OS F1.61 _{_{F 3 CHH OCH 2 6-Et}} OS F1.62 Me HH OCH _{2 7-Et OS F1.63 Me HH} SCH 2 7-Et OS F1.64 Et HH OCH 2 7-Et OS F1.65 nPr HH OCH 2 7-Et OS F1.66 iPr HH OCH 2 7-Et OS F1 _{.67 nBu HH OCH 2 7-Et} OS F1.68 F 3 CHH OCH 2 7-Et OS F1.69 MeO HH OCH 2 5-NO 2 OO 184-187 F2.1 Me HH OCH 2 4-CH 2 CH = CH ₂ OS F2.2 Et HH OCH ₂ 4-CH ₂ CH = CH ₂ OS F2.3 nPr HH OCH ₂ 4-CH ₂ CH = CH ₂ OS F2.4 iPr HH OCH ₂ 4-CH ₂ CH = CH ₂ OS F2.5 nBu HH OCH ₂ 4-CH ₂ CH = CH ₂ OS F2.6 F ₃ CHH OCH ₂ 4-CH ₂ CH = CH ₂ OS F2.7 Me HH OCH ₂ 5-CH ₂ CH = CH ₂ OS F2.8 MeO HH OCH ₂ 5-CH ₂ CH = CH ₂ OS F2.9 Me HH OCH ₂ 5-CH ₂ CH = CH ₂ OO F2.10 MeO HH OCH ₂ 5-CH ₂ CH = CH ₂ OO F2. 11 Et HH OCH ₂ 5-CH ₂ CH = CH ₂ OS F2.12 nBu Pr HH OCH ₂ 5-CH ₂ CH = CH ₂ OS F2.13 iPr HH OCH ₂ 5-CH ₂ CH = CH ₂ OS F2.14 nBu _{_{HH OCH 2 5-CH 2 CH}} = CH 2 OS F2.15 F 3 CHH OCH 2 5-CH 2 CH = CH 2 OS F2.16 Me HH OCH 2 6-CH 2 CH = CH 2 OS F2.17 MeO HH _{_{OCH 2 6-CH 2 CH =}} CH 2 OS F2.18 Et HH OCH 2 6-CH 2 CH = CH 2 OS F2.19 nPr HH OCH 2 6-CH 2 CH = CH 2 OS F2.20 iPr HH OCH 2 6-CH ₂ CH = CH ₂ OS F2.21 nBu HH OCH ₂ 6-CH ₂ CH = CH ₂ OS F2.22 F ₃ CHH OCH ₂ 6-CH ₂ CH _{= CH 2 OS F2.23 Me HH OCH} 2 7-CH 2 CH = CH 2 OS F2.24 Et HH OCH 2 7-CH 2 CH = CH 2 OS F2.25 nPr HH OCH 2 7-CH 2 CH = CH _{_{2 OS F2.26 iPr HH OCH 2 7}} -CH 2 CH = CH 2 OS F2.27 nBu HH OCH 2 7-CH 2 CH = CH 2 OS F2.28 F 3 CHH OCH 2 7-CH 2 CH = CH 2 OS F2.29 Me HH OCH ₂ 5-CH ₂ C≡CH OS F2.30 MeO HH OCH ₂ 5-CH ₂ C≡CH OS F2.31 Me HH OCH ₂ 5-CH ₂ C≡CH OO F2.32 MeO _{_{HH OCH 2 5-CH 2 C≡CH}} OO F2.33 Me HH OCH 2 6-CH 2 C≡CH OS F2.34 MeO HH OCH 2 6-CH 2 C≡CH OS F3.1 Me HH OCH 2 4- _{OMe OS 147-148 F3.2 Me HH SCH 2} 4-OMe OS F3.3 MeO HH OCH 2 4-OMe OS 117-120 F3.4 MeO HH OCH 2 4-OMe OO F3.5 Et HH OCH 2 4- OMe OS F3.6 nPr HH OCH ₂ 4-OMe OS F3.7 iPr HH OCH ₂ 4-OMe OS F3.8 nBu HH OCH ₂ 4-OMe OS F3.9 F ₃ CHH OCH ₂ 4-OMe OS F3.10 Me HH OCH ₂ 5-OMe OS 217-219 F3.11 Me HH SCH ₂ 5-OMe OS F3.12 MeO HH OCH ₂ 5-OMe OS F3.13 Me HH OCH ₂ 5-OMe OO F3.14 MeO HH OCH ₂ 5-OMe OO 134-137 F3.15 Et HH OCH ₂ 5-OMe OS F3.16 nPr HH OCH ₂ 5-OMe OS F3.17 iPr HH OCH ₂ 5-OMe OS F3.18 nBu HH OCH ₂ 5- OMe OS F3.19 F ₃ CHH OCH ₂ 5-OMe OS F3.20 M _{e HH OCH 2 6-OMe OS} 145-147 F3.21 Me HH SCH 2 6-OMe OS 124-125 F3.22 MeO HH OCH 2 6-OMe OS 118-120 F3.23 MeO HH OCH 2 6-OMe OO _{F3.24 Et HH OCH 2 6-OMe} OS F3.25 nPr HH OCH 2 6-OMe OS F3.26 iPr HH OCH 2 6-OMe OS F3.27 nBu HH OCH 2 6-OMe OS F3.28 F 3 CHH _{OCH 2 6-OMe OS F3.29 Me} HH OCH 2 7-OMe OS 163-164 F3.30 Me HH SCH 2 7-OMe OS F3.31 MeO HH OCH 2 7-OMe OS 174-176 F3.32 MeO HH _{OCH 2 7-OMe OO F3.33 Et} HH OCH 2 7-OMe OS F3.34 nPr HH OCH 2 7-OMe OS F3.35 iPr HH OCH 2 7-OMe OS F3.36 nBu HH OCH 2 7-OMe OS F3.37 F ₃ CHH OCH ₂ 7-OMe OS F3.38 Me HH OCH ₂ 4-OEt OS F3.39 Me HH SCH ₂ 4-OEt OS F3.40 Et HH OCH ₂ 4-OEt OS F3.41 nPr HH OCH ₂ 4-OEt OS F3.42 iPr HH OCH ₂ 4-OEt OS F3.43 nBu HH OCH ₂ 4-OEt OS F3.45 F ₃ CHH OCH ₂ 4-OEt OS F3.46 Me HH OCH ₂ 5-OEt OS F3.47 Me HH SCH ₂ 5-OEt OS F3.48 MeO HH OCH ₂ 5-OEt OS F3.49 Me HH OCH ₂ 5-OEt OO F3.50 MeO HH OCH ₂ 5-OEt OO F3.51 Et HH _{OCH 2 5-OEt OS F3.53 iPr} HH OCH 2 5-OEt OS F3.54 nBu HH OCH 2 5-OEt OS F3.55 F 3 CHH OCH 2 5-OEt OS F3.56 Me HH OCH 2 6-OEt _{OS 139-141 F3.57 Me HH SCH 2 6} -OEt OS F3.58 MeO HH OCH 2 6-OEt OS F3.59 Me HH OCH 2 6-OEt OO F3.60 MeO HH OCH 2 6-OEt OO F3. _{61 Et HH OCH 2 6-OEt} OS F3.62 nPr HH OCH 2 6-OEt OS F3.63 iPr HH OCH 2 6-OEt OS F3.64 nBu HH OCH 2 6-OEt OS F3.65 F 3 CHH OCH 2 6-OEt OS F3.66 Me HH OCH 2 7-OEt OS F3.67 Me HH SCH 2 7-OEt OS F3.68 Et HH OCH 2 7-OEt OS F3.69 nPr HH OCH 2 7-OEt OS F3. _{70 iPr HH OCH 2 7-OEt} OS F3.71 nBu HH OCH 2 7-OEt OS F3.72 F 3 CHH OCH 2 7-OEt OS F4.1 Me HH OCH 2 4-FOS 156-158 F4.2 Me HH SCH ₂ 4-FOS F4.3 MeO HH OCH ₂ 4-FOS F4.4 Me HH OCH ₂ 4-FOO F4.5 MeO HH OCH ₂ 4-FOO F4.6 Et HH OCH ₂ 4-FOS F4.7 nPr HH OCH ₂ 4-FOS F4.8 iPr HH OCH ₂ 4-FOS F4.9 nBu HH OCH ₂ 4-FOS F4.10 F ₃ CHH OCH ₂ 4-FOS F4.11 Me HH OCH ₂ 5-FOS 201 F4.12 MeO HH OCH ₂ 5-FOS 174-176 F4.13 Me HH OCH ₂ 5-FOO F4.14 MeO HH OCH ₂ 5-FOO 133-134 F4.15 MeO HH SCH ₂ 5-FOO F4.16 Me HH SCH ₂ 5-FOS 108-109 F4.17 MeO HH SCH ₂ 5-FOS F4.18 Et HH OCH ₂ 5-FOS F4.19 nPr HH OCH ₂ 5-FOS 201-202 F4.20 nBu HH OCH ₂ 5-FOS 189 -191 F4.21 iPr HH OCH ₂ 5-FOS F4.22 c-Hex HH OCH ₂ 5-FOS 211-212 F4.23 FCH ₂ HH OCH ₂ 5-FOS 192-193 F4.24 FCH ₂ HH OCH ₂ 5-FOO F4.25 ClCH ₂ HH OCH ₂ 5-FOS 198-200 F4.26 ClCH ₂ HH OCH ₂ 5-FOO F4.27 Cl ₂ CH HH OCH ₂ 5-FOS 208-209 F4.28 F ₃ CHH OCH ₂ 5-FOS 204-206 _{_{F4.29 F 3 CHH OCH 2 5-}} FOO F4.30 Me HH OCH 2 6-FOS 204-205 F4.31 MeO HH OCH 2 6-FOS F4.32 Me HH OCH 2 6-FOO F4.33 MeO HH OCH _{2 6-FOO 120-122 F4.34 Me HH} SCH 2 6-FOS F4.35 Et HH OCH 2 6-FOS F4.36 nPr HH OCH 2 6-FOS F4.37 iPr HH OCH 2 6-FOS F4.38 _{nBu HH OCH 2 6-FOS F4.39} F 3 CHH OCH 2 6-FOS F4.40 Me HH OCH 2 7-FOS 149-152 F4.41 MeO HH OCH 2 7-FOS 136-139 F4.42 Me HH OCH _{2 7-FOO F4.43 MeO HH OCH} 2 7-FOO 120-123 F4.44 Me HH SCH 2 7-FOS F4.45 Et HH OCH 2 7-FOS F4.46 nPr HH OCH 2 7-FOS F4.47 _{iPr HH OCH 2 7-FOS F4.48} nBu HH OCH 2 7-FOS F4.49 F 3 CHH OCH 2 7-FOS F4.50 Me HH OCH 2 4-Cl OS F4.51 Me HH SCH 2 4-Cl OS F4.52 MeO HH OCH ₂ 4-Cl OS F4.53 MeO HH OCH ₂ 4-Cl OO F4.54 Et HH OCH ₂ 4-Cl OS F4.55 nPr HH OCH ₂ 4-Cl OS F4.56 iPr HH OCH ₂ 4-Cl OS F4.57 nBu HH OCH ₂ 4-Cl OS F4.58 F ₃ CHH OCH ₂ 4-Cl OS F4.59 Me HH OCH ₂ 5-Cl OS 230-232 F4.60 Me HH SCH ₂ 5-Cl OS F4.61 MeO HH OCH ₂ 5-Cl OS 211-213 F4.62 Me HH OCH ₂ 5-Cl OO F4.63 MeO HH OCH ₂ 5-Cl OO 157-160 F4.64 Et HH OCH ₂ 5-Cl OS F4.65 nPr HH _{OCH 2 5-Cl OS F4.66 iPr} HH OCH 2 5-Cl OS F4.67 nBu HH OCH 2 5-Cl OS F4.68 F 3 CHH OCH 2 5-Cl OS F4.69 Me HH OCH 2 6-Cl _{OS 218 F4.70 Me HH SCH 2 6} -Cl OS F4.71 MeO HH OCH 2 6-Cl OS 195-197 F4.72 Me HH OCH 2 6-Cl OO F4.73 MeO HH OCH 2 6-Cl OO F4 _{.74 Et HH OCH 2 6-Cl} OS F4.75 nPr HH OCH 2 6-Cl OS F4.76 iPr HH OCH 2 6-Cl OS F4.77 nBu HH OCH 2 6-Cl OS F4.78 F 3 CHH OCH _{2 6-Cl OS F4.79 Me HH} OCH 2 7-Cl OS 172-175 F4.80 Me HH SCH 2 7-Cl OS F4.81 MeO HH OCH 2 7-Cl OS 159-162 F4.82 Et HH OCH _{2 7-Cl OS F4.83 nPr HH} OCH 2 7-Cl OS F4.84 iPr HH OCH 2 7-Cl OS F4.85 nBu HH OCH 2 7-Cl OS F4.86 F 3 CHH OCH 2 7-Cl OS F4.87 Me HH OCH ₂ 4-Br OS F4.88 Me HH SCH ₂ 4-Br OS F4.89 MeO HH OCH ₂ 4-Br OS F4.90 Et HH OCH ₂ 4-Br OS F4.91 nPr HH OCH ₂ 4-Br OS F4.92 iPr HH OCH ₂ 4-Br OS F4.93 nBu HH OCH ₂ 4-Br OS F4.94 F ₃ CHH OCH ₂ 4-Br OS F4.95 Me HH OCH ₂ 5-Br OS F4.96 Me HH SCH ₂ 5-Br OS F4 .97 MeO HH OCH ₂ 5-Br OS F4.98 Et HH OCH ₂ 5-Br OS F4.99 nPr HH OCH ₂ 5-Br OS F4.100 iPr HH OCH ₂ 5-Br OS F4.101 nBu HH OCH ₂ _{5-Br OS F4.102 F 3 CHH} OCH 2 5-Br OS F4.103 Me HH OCH 2 6-Br OS 218-221 F4.104 Me HH SCH 2 6-Br OS F4.105 MeO HH OCH 2 6- _{Br OS F4.106 Me HH OCH 2 6} -Br OO F4.107 MeO HH OCH 2 6-Br OO F4.108 Et HH OCH 2 6-Br OS F4.109 nPr HH OCH 2 6-Br OS F4.110 iPr _{HH OCH 2 6-Br OS F4.111} nBu HH OCH 2 6-Br OS F4.112 F 3 CHH OCH 2 6-Br OS F4.113 Me HH OCH 2 7-Br OS F4.114 Me HH SCH 2 7- _{Br OS F4.115 MeO HH OCH 2 7} -Br OS F4.116 Et HH OCH 2 7-Br OS F4.117 nPr HH OCH 2 7-Br OS F4.118 iPr HH OCH 2 7-Br OS F4.119 nBu _{HH OCH 2 7-Br OS F4.120} F 3 CHH OCH 2 7-Br OS F5.1 Me HH OCH 2 4-CF 3 OS F5.2 Me HH SCH 2 4-CF 3 OS F5.3 MeO HH OCH 2 4-CF ₃ OS 179-180 F5.4 Et HH OCH ₂ 4-CF ₃ OS F5.6 iPr HH OCH ₂ 4-CF ₃ OS F5.7 nBu HH OCH ₂ 4-CF ₃ OS F5.8 F ₃ CHH OCH ₂ 4-CF ₃ OS F5.9 Me HH OCH ₂ 5-CF ₃ OS 208-210 F5.10 Me HH SCH ₂ 5-CF ₃ OS F5.11 MeO HH OCH ₂ 5-CF ₃ OS F5.12 Me HH OCH ₂ 5-CF ₃ OO F5.13 MeO HH OCH ₂ 5-CF ₃ OO 145-148 F5.14 Et HH OCH ₂ 5-CF ₃ OS F5.15 nPr HH OCH ₂ 5-CF ₃ OS F5.16 iPr HH OCH ₂ 5-CF ₃ OS F5.17 _{_{nBu HH OCH 2 5-CF 3}} OS F5.18 F 3 CHH OCH 2 5-CF 3 OS F5.19 Me HH OCH 2 6-CF 3 OS F5.20 Me HH SCH 2 6-CF 3 OS F5.21 MeO _{_{HH OCH 2 6-CF 3 OS}} F5.22 Me HH OCH 2 6-CF 3 OO F5.23 MeO HH OCH 2 6-CF 3 OO F5.24 Et HH OCH 2 6-CF 3 OS F5.25 nPr HH OCH _{_{2 6-CF 3 OS F5.26 iPr}} HH OCH 2 6-CF 3 OS F5.27 nBu HH OCH 2 6-CF 3 OS F5.28 F 3 CHH OCH 2 6-CF 3 OS F5.29 Me HH OCH 2 7-CF ₃ OS F5.30 Me HH SCH ₂ 7-CF ₃ OS F5.31 MeO HH OCH ₂ 7-CF ₃ OS F5.32 Et HH OCH ₂ 7-CF ₃ OS F5.34 nPr HH OCH ₂ 7- _{_{CF 3 OS F5.36 nBu HH OCH 2}} 7-CF 3 OS F5.37 F 3 CHH OCH 2 7-CF 3 OS F5.38 Me HH OCH 2 4-OCF 3 OS F5.39 Me HH SCH 2 4-OCF ₃ OS F5.40 Et HH OCH ₂ 4-OCF ₃ OS F5.41 nPr HH OCH ₂ 4-OCF ₃ OS F5.42 iPr HH OCH ₂ 4-OCF ₃ OS F5.43 nBu HH OCH ₂ 4-OCF ₃ OS F5.44 F ₃ CHH OCH ₂ 4-OCF ₃ OS F5.45 Me HH O CH ₂ 5-OCF ₃ OS F5.46 Me HH SCH ₂ 5-OCF ₃ OS F5.47 MeO HH OCH ₂ 5-OCF ₃ OS F5.48 Me HH OCH ₂ 5-OCF ₃ OO F5.49 MeO HH OCH ₂ 5-OCF ₃ OO F5.50 Et HH OCH ₂ 5-OCF ₃ OS F5.51 nPr HH OCH ₂ 5-OCF ₃ OS F5.52 iPr HH OCH ₂ 5-OCF ₃ OS F5.53 nBu HH OCH ₂ 5- _{_{OCF 3 OS F5.54 F 3 CHH OCH}} 2 5-OCF 3 OS F5.56 Me HH OCH 2 6-OCF 3 OS F5.57 Me HH SCH 2 6-OCF 3 OS F5.58 MeO HH OCH 2 6-OCF _{_{3 OS F5.59 Et HH OCH 2 6}} -OCF 3 OS F5.60 nPr HH OCH 2 6-OCF 3 OS F5.61 iPr HH OCH 2 6-OCF 3 OS F5.62 nBu HH OCH 2 6-OCF 3 OS _{_{F5.63 F 3 CHH OCH 2 6-}} OCF 3 OS F5.64 Me HH OCH 2 7-OCF 3 OS F5.65 Me HH SCH 2 7-OCF 3 OS F5.66 Et HH OCH 2 7-OCF 3 OS F5 _{.67 nPr HH OCH 2 7-OCF} 3 OS F5.68 iPr HH OCH 2 7-OCF 3 OS F5.69 nBu HH OCH 2 7-OCF 3 OS F5.70 F 3 CHH OCH 2 7-OCF 3 OS F6. _{1 Me HH OCH 2 5-CHO} OS F6.2 MeO HH OCH 2 5-CHO OS F6.3 Me HH OCH 2 6-CHO OS F6.4 MeO HH OCH 2 6-CHO OS F6.5 Me HH OCH 2 5 _{-COMe OS F6.6 MeO HH OCH 2 5} -COMe OS F6.7 Me HH OCH 2 6-COMe OS F6.8 MeO HH OCH 2 6-COMe OS F6.9 Me HH OCH 2 4-COOMe OS F6.10 MeO HH OCH ₂ 4-COOMe OS F6.11 Me HH OCH ₂ 4-COOMe OO 158-160 F6.12 MeO HH OCH ₂ 4-COOMe OO Clay F6.13 Me HH OCH ₂ 5-COOMe OS F6.14 MeO HH OCH ₂ 5-COOMe OS _{F6.15 Me HH OCH 2 5-COOMe} OO 165-168 F6.16 MeO HH OCH 2 5-COOMe OO 163-167 F6.17 Me HH OCH 2 6-COOMe OS F6.18 MeO HH OCH 2 6-COOMe OS _{F6.19 Me HH OCH 2 6-COOMe} OO 155-158 F6.20 MeO HH OCH 2 6-COOMe OO ~230 F6.21 Me HH OCH 2 7-COOMe OS F6.22 MeO HH OCH 2 7-COOMe OS F6 _{.23 Me HH OCH 2 7-COOMe} OO 102-105 F6.24 MeO HH OCH 2 7-COOMe OO 142-146 F7.1 Me HH OCH 2 4,5-Me 2 OS F7.2 Me HH SCH 2 4, 5-Me ₂ OS F7.3 MeO HH OCH ₂ 4,5-Me ₂ OS F7.4 Me HH OCH ₂ 4,6-Me ₂ OS F7.5 Me HH SCH ₂ 4,6-Me ₂ OS F7.6 MeO HH OCH ₂ 4,6-Me ₂ OS F7.7 Me HH OCH ₂ 4,6-Me ₂ OO F7.8 MeO HH OCH ₂ 4,6-Me ₂ OO F7.9 Me HH OCH ₂ 4,7- Me ₂ OS F7.10 Me HH SCH ₂ 4,7-Me ₂ OS F7.11 Me HH OCH ₂ 5,6-Me ₂ OS F7.12 Me HH SCH ₂ 5,6-Me ₂ OS F7.13 Me HH OCH ₂ 5,7-Me ₂ OS F7.14 Me HH SCH ₂ 5,7-Me ₂ OS F7.15 MeO HH OCH ₂ 5,7-Me ₂ OS F7.16 Me HH OCH ₂ 5,7-Me ₂ OO F7.17 MeO HH OCH ₂ 5,7-Me ₂ OO 157-159 F7.1 8 Me HH OCH ₂ 6,7-Me ₂ OS F7.19 Me HH SCH ₂ 6,7-Me ₂ OS F7.20 MeO HH OCH ₂ 6,7-Me ₂ OS F7.21 Me HH OCH ₂ 4,5 -(OMe) ₂ OS F7.22 Me HH SCH ₂ 4,5- (OMe) ₂ OS F7.23 Me HH OCH ₂ 4,6- (OMe) ₂ OS F7.24 Me HH SCH ₂ 4,6- ( OMe) ₂ OS F7.25 Me HH OCH ₂ 4,7- (OMe) ₂ OS F7.26 Me HH SCH ₂ 4,7- (OMe) ₂ OS F7.27 Me HH OCH ₂ 5,6- (OMe) ₂ OS F7.28 Me HH SCH ₂ 5,6- (OMe) ₂ OS F7.29 MeO HH OCH ₂ 5,6- (OMe) ₂ OS F7.30 Me HH OCH ₂ 5,7- (OMe) ₂ OS _{F7.31 Me HH SCH 2 5,7- (OMe} ) 2 OS F7.32 Me HH OCH 2 6,7- (OMe) 2 OS F7.33 Me HH SCH 2 6,7- (OMe) 2 OS F7. 34 Me HH OCH ₂ 4,5-F ₂ OS 178-180 F7.35 Me HH SCH ₂ 4,5-F ₂ OS F7.36 MeO HH OCH ₂ 4,5-F ₂ OS F7.37 Me HH OCH ₂ 4,5-F ₂ OO F7.38 MeO HH OCH ₂ 4,5-F ₂ OO F7.39 Me HH OCH ₂ 4,6-F ₂ OS 198-200 F7.40 Me HH SCH ₂ 4,6-F ₂ OS F7.41 MeO HH OCH ₂ 4,6-F ₂ OS F7.42 Me HH OCH ₂ 4,7-F ₂ OS F7.43 Me HH SCH ₂ 4,7-F ₂ OS F7.44 MeO HH OCH ₂ 4,7-F ₂ OS F7.45 Me HH OCH ₂ 5,6-F ₂ OS 212-214 F7.46 Me HH SCH ₂ 5,6-F ₂ OS F7.47 MeO HH OCH ₂ 5,6- F ₂ OS F7.48 Me HH OCH ₂ 5,6-F ₂ OO F7.49 MeO HH OCH ₂ 5,6-F ₂ OO F7.50 Me HH OCH ₂ 5,7-F ₂ OS F7.52 Me HH SCH ₂ 5,7-F ₂ OS F7.53 MeO HH OCH ₂ 5,7-F ₂ OS F7 _{.54 Me HH OCH 2 6,7-F} 2 OS F7.55 Me HH SCH 2 6,7-F 2 OS F7.56 MeO HH OCH 2 6,7-F 2 OO 145-148 F7.57 Me HH OCH ₂ 4,5-Cl ₂ OS F7.58 Me HH SCH ₂ 4,5-Cl ₂ OS F7.59 Me HH OCH ₂ 4,6-Cl ₂ OS F7.60 Me HH SCH ₂ 4,6-Cl ₂ OS F7.61 Me HH OCH ₂ 4,7-Cl ₂ OS F7.62 Me HH SCH ₂ 4,7-Cl ₂ OS F7.63 Me HH OCH ₂ 5,6-Cl ₂ OS F7.64 Me HH SCH ₂ 5 , 6-Cl ₂ OS F7.65 Me HH OCH ₂ 5,7-Cl ₂ OS F7.66 Me HH SCH ₂ 5,7-Cl ₂ OS F7.67 MeO HH OCH ₂ 5,7-Cl ₂ OS F7. 68 Me HH OCH ₂ 5,7-Cl ₂ OO F7.69 MeO HH OCH ₂ 5,7-Cl ₂ OO 135-136 F7.70 Me HH OCH ₂ 6,7-Cl ₂ OS F7.71 Me HH SCH ₂ _{6,7-Cl 2 OS F7.72 Me HH} OCH 2 4,5- (CF 3) 2 OS F7.73 Me HH SCH 2 4,5- (CF 3) 2 OS F7.74 Me HH OCH 2 4, 6- (CF ₃ ) ₂ OS F7.75 Me HH SCH ₂ 4,6- (CF ₃ ) ₂ OS F7.76 Me HH OCH ₂ 4,7- (CF ₃ ) ₂ OS F7.77 Me HH SCH ₂ 4 , 7- (CF ₃ ) ₂ OS F7.78 Me HH OCH ₂ 5,6- (CF ₃ ) ₂ OS F7.79 Me HH SCH ₂ 5,6- (CF ₃ ) ₂ OS F7.80 Me HH OCH ₂ 5,7- (CF ₃ ) ₂ OS F7.81 Me HH SCH ₂ 5,7- (CF ₃ ) ₂ OS F7.82 Me HH OCH ₂ 6,7- (CF ₃ ) ₂ OS F7.83 Me HH SCH ₂ 6,7- (CF ₃ ) ₂ OS F7.84 Me HH OCH ₂ 4-F, 5-Me OS F7.85 Me HH SCH ₂ 4-F, 5-Me OS F7.86 Me HH OCH ₂ 4-F, 6-Me OS F7.87 Me HH SCH ₂ 4-F, 6-Me OS F7.88 Me _{HH OCH 2 4-F, 7} -Me OS F7.89 Me HH SCH 2 4-F, 7-Me OS F7.90 Me HH OCH 2 4-Me, 5-FOS F7.91 Me HH SCH 2 4-Me , 5-FOS F7.92 Me HH OCH ₂ 5-F, 6-Me OS 231-234 F7.93 Me HH SCH ₂ 5-F, 6-Me OS F7.94 Me HH OCH ₂ 5-F, 7- Me OS F7.95 Me HH SCH ₂ 5-F, 7-Me OS F7.96 MeO HH OCH ₂ 5-F, 7-Me OS F7.97 Me HH OCH ₂ 4-Me, 6-FOS F7.98 Me HH SCH ₂ 4-Me, 6-FOS F7.99 Me HH OCH ₂ 5-Me, 6-FOS 231-234 F7.100 Me HH SCH ₂ 5-Me, 6-FOS F7.101 MeO HH OCH ₂ 6- F, 5-Me OS F7.102 Me HH OCH 2 6-F, 7-Me OS F7.103 Me HH SCH 2 6-F, 7-Me OS F7.104 Me HH OCH 2 4-Me, 7-FOS F7.105 Me HH SCH ₂ 4-Me, 7-FOS F7.106 Me HH OCH ₂ 5-Me, 7-FOS F7.107 Me HH SCH ₂ 5-Me, 7-FOS F7.108 Me HH OCH ₂ 6 -Me, 7-FOS F7.109 Me HH SCH ₂ 6-Me, 7-FOS F7.110 Me HH OCH ₂ 4-Cl, 5-Me OS F7.111 Me HH SCH ₂ 4-Cl, 5-Me OS F7.112 MeO HH OCH ₂ 4-Cl, 5-Me OS F7.113 Me HH OCH ₂ 4-Cl, 6-Me OS F7.114 Me HH SCH ₂ 4-Cl, 6-Me OS F7.115 MeO HH OCH ₂ 4-Cl, 6-Me OS F7.116 Me HH OCH ₂ 4-Cl, 7-Me OS F7.117 Me HH SCH ₂ 4-Cl, 7-Me OS F7.118 Me HH OCH ₂ 4-Me, 5-Cl OS F7.119 Me HH SCH ₂ 4-Me, 5-Cl OS F7.120 Me HH OCH ₂ 5-Cl , 6-Me OS 236-239 F7.121 Me HH SCH 2 5-Cl, 6-Me OS F7.122 Me HH OCH 2 5-Cl, 7-Me OS F7.123 Me HH SCH 2 5-Cl, 7 _{-Me OS F7.124 Me HH OCH 2 4} -Me, 6-Cl OS F7.125 Me HH SCH 2 4-Me, 6-Cl OS F7.126 Me HH OCH 2 5-Me, 6-Cl OS F7. _{127 Me HH SCH 2 5-Me} , 6-Cl OS F7.128 Me HH OCH 2 7-Me, 6-Cl OS F7.129 Me HH SCH 2 7-Me, 6-Cl OS F7.130 Me HH OCH 2 4-Me, 7-Cl OS F7.131 Me HH SCH ₂ 4-Me, 7-Cl OS F7.132 Me HH OCH ₂ 5-Me, 7-Cl OS F7.133 Me HH SCH ₂ 5-Me, 7 _{-Cl OS F7.134 Me HH OCH 2 6} -Me, 7-Cl OS F7.135 Me HH SCH 2 6-Me, 7-Cl OS F7.136 Me HH OCH 2 4-Cl, 5-OMe OS 193- _{195 F7.137 Me HH SCH 2 4-} Cl, 5-OMe OS F7.138 MeO HH OCH 2 4-Cl, 5-OMe OS F7.139 Me HH OCH 2 4-Cl, 5-OMe OO F7.140 MeO _{HH OCH 2 4-Cl, 5} -OMe OO F7.141 Me HH OCH 2 4-Cl, 6-OMe OS F7.142 Me HH SCH 2 4-Cl, 6-OMe OS F7.144 Me HH OCH 2 4- Cl, 7-OMe OS F7.144 Me HH SCH ₂ 4-Cl, 7-OMe OS F7.145 Me HH OCH ₂ 4-OMe, 5-Cl OS F7.146 Me HH SCH ₂ 4-OMe, 5-Cl OS F7.147 Me HH OCH ₂ 5-Cl , 6-OMe OS 222-225 F7.148 Me HH SCH ₂ 5-Cl, 6-OMe OS F7.149 MeO HH OCH ₂ 5-Cl, 6-OMe OS F7.150 MeO HH OCH ₂ 5-Cl, 6 -OMe OO F7.151 Me HH OCH ₂ 5-Cl, 7-OMe OS F7.152 Me HH SCH ₂ 5-Cl, 7-OMe OS F7.153 Me HH OCH ₂ 4-OMe, 6-Cl OS F7. 154 Me HH SCH ₂ 4-OMe, 6-Cl OS F7.155 Me HH OCH ₂ 5-OMe, 6-Cl OS F7.156 Me HH SCH ₂ 5-OMe, 6-Cl OS F7.157 Me HH OCH ₂ 6-Cl, 7-OMe OS F7.158 Me HH SCH ₂ 6-Cl, 7-OMe OS F7.159 Me HH OCH ₂ 4-OMe, 7-Cl OS F7.160 Me HH SCH ₂ 4-OMe, 7 _{-Cl OS F7.161 Me HH OCH 2 5} -OMe, 7-Cl OS F7.162 Me HH SCH 2 5-OMe, 7-Cl OS F7.163 Me HH OCH 2 6-OMe, 7-Cl OS F7. _{164 Me HH SCH 2 6-OMe} , 7-Cl OS F7.165 Me HH OCH 2 4-Cl, 5-FOS F7.166 Me HH OCH 2 4-Cl, 6-FOS F7.167 Me HH OCH 2 4- Cl, 7-FOS F7.168 Me HH OCH ₂ 4-F, 5-Cl OS F7.169 Me HH OCH ₂ 5-Cl, 6-FOS 227-229 F7.170 MeO HH OCH ₂ 5-Cl, 6- _{FOS F7.171 Me HH OCH 2 5-} Cl, 6-FOO F7.172 MeO HH OCH 2 5-Cl, 6-FOO F7.173 Me HH OCH 2 6-F, 7-Cl OS 182-185 F7.174 MeO HH OCH ₂ 6-F, 7-Cl OS F7.175 Me HH OCH ₂ 5-Cl, 7-FOS F7.176 Me HH OCH ₂ 4-F, 6-Cl OS F7.177 Me HH OCH ₂ 5-F, 6- Cl OS F7.178 Me HH OCH ₂ 6-Cl, 7-FOS F7.179 Me HH OCH ₂ 4-F, 7-Cl OS F7.180 Me HH OCH ₂ 5-F, 7-Cl OS ──── ────────────────────────────────

【００５７】[0057]

【表７】 ──────────────────────────────────── 番号 R¹ R² (R³)n ACR⁴(R⁵) (R⁶)m X Q 融点（℃） ──────────────────────────────────── G1.1 Me H 2-Me OCH₂ 4-Me O S G1.2 Me H 2-Me SCH₂ 4-Me O S G1.3 MeO H 2-Me OCH₂ 4-Me O S 153-155 G1.4 Me H 2-Me OCH₂ 4-Me O O 160-161 G1.5 MeO H 2-Me OCH₂ 4-Me O O 149-151 G1.6 Me H 2-Me OCH₂ 5-Me O S 206-208 G1.7 Me H 2-Me SCH₂ 5-Me O S G1.8 MeO H 2-Me OCH₂ 5-Me O S 131-133 G1.9 Me H 2-Me OCH₂ 5-Me O O 177-180 G1.10 MeO H 2-Me OCH₂ 5-Me O O 164-166 G1.11 Me H 2-Me OCH₂ 6-Me O S 192-193 G1.12 Me H 2-Me SCH₂ 6-Me O S G1.13 MeO H 2-Me OCH₂ 6-Me O S 153-155 G1.14 Me H 2-Me OCH₂ 6-Me O O 185-188 G1.15 MeO H 2-Me OCH₂ 6-Me O O 139-142 G1.16 Me H 2-Me OCH₂ 7-Me O S G1.17 Me H 2-Me SCH₂ 7-Me O S G1.18 MeO H 2-Me OCH₂ 7-Me O S G1.19 Me H 2-Me OCH₂ 7-Me O O 170-173 G1.20 MeO H 2-Me OCH₂ 7-Me O O 157-159 G1.21 Me H 2-Me OCH₂ 5-Et O S G1.22 Me H 2-Me SCH₂ 5-Et O S G1.23 MeO H 2-Me OCH₂ 5-Et O S G1.24 MeO H 2-Me OCH₂ 5-Et O O G1.25 Me H 2-Me OCH₂ 6-Et O S G1.26 Me H 2-Me SCH₂ 6-Et O S G1.27 MeO H 2-Me OCH₂ 6-Et O S G1.28 Me H 2-Me OCH₂ 4-OMe O S G1.29 Me H 2-Me SCH₂ 4-OMe O S G1.30 MeO H 2-Me OCH₂ 4-OMe O S 125-126 G1.31 MeO H 2-Me OCH₂ 4-OMe O O G1.32 Me H 2-Me OCH₂ 5-OMe O S 203-204 G1.33 Me H 2-Me SCH₂ 5-OMe O S G1.34 MeO H 2-Me OCH₂ 5-OMe O S 159-161 G1.35 Me H 2-Me OCH₂ 5-OMe O O 173-177 G1.36 MeO H 2-Me OCH₂ 5-OMe O O 160-162 G1.37 Me H 2-Me OCH₂ 6-OMe O S 159-162 G1.38 Me H 2-Me SCH₂ 6-OMe O S G1.39 MeO H 2-Me OCH₂ 6-OMe O S 123-125 G1.40 Me H 2-Me OCH₂ 6-OMe O O G1.41 MeO H 2-Me OCH₂ 6-OMe O O G1.42 Me H 2-Me OCH₂ 7-OMe O S G1.43 Me H 2-Me SCH₂ 7-OMe O S G1.44 MeO H 2-Me OCH₂ 7-OMe O S 150-151 G1.45 MeO H 2-Me OCH₂ 7-OMe O O G1.46 Me H 2-Me OCH₂ 5-OEt O S G1.47 Me H 2-Me SCH₂ 5-OEt O S G1.48 Me H 2-Me OCH₂ 6-OEt O S G1.49 Me H 2-Me SCH₂ 6-OEt O S G1.50 Me H 2-Me OCH₂ 4-F O S 174-176 G1.51 Me H 2-Me SCH₂ 4-F O S G1.52 MeO H 2-Me OCH₂ 4-F O S 165-167 G1.53 Me H 2-Me OCH₂ 4-F O O G1.54 MeO H 2-Me OCH₂ 4-F O O G1.55 Me H 2-Me OCH₂ 5-F O S 205-207 G1.56 Me H 2-Me SCH₂ 5-F O S G1.57 MeO H 2-Me OCH₂ 5-F O S 165-168 G1.58 Me H 2-Me OCH₂ 5-F O O 183-185 G1.59 MeO H 2-Me OCH₂ 5-F O O 182-184 G1.60 Me H 2-Me OCH₂ 6-F O S 204-205 G1.61 Me H 2-Me SCH₂ 6-F O S G1.62 MeO H 2-Me OCH₂ 6-F O S 149-151 G1.63 Me H 2-Me OCH₂ 6-F O O 178-179 G1.64 MeO H 2-Me OCH₂ 6-F O O 138-140 G1.65 Me H 2-Me OCH₂ 7-F O S G1.66 Me H 2-Me SCH₂ 7-F O S G1.67 MeO H 2-Me OCH₂ 7-F O S 121-122 G1.68 Me H 2-Me OCH₂ 7-F O O 173-175 G1.69 MeO H 2-Me OCH₂ 7-F O O 138-141 G1.70 MeO H 2-Me OCH₂ 4-Cl O S G1.71 MeO H 2-Me OCH₂ 4-Cl O O G1.72 Me H 2-Me OCH₂ 5-Cl O S 213-214 G1.73 Me H 2-Me SCH₂ 5-Cl O S G1.74 MeO H 2-Me OCH₂ 5-Cl O S 179-182 G1.75 MeO H 2-Me SCH₂ 5-Cl O S G1.76 Me H 2-Me OCH₂ 5-Cl O O 207-209 G1.77 MeO H 2-Me OCH₂ 5-Cl O O 156-158 G1.78 MeO H 2-Me SCH₂ 5-Cl O O G1.79 Me H 2-Me OCH₂ 6-Cl O S G1.80 Me H 2-Me SCH₂ 6-Cl O S G1.81 MeO H 2-Me OCH₂ 6-Cl O S 150-152 G1.82 Me H 2-Me OCH₂ 6-Cl O O G1.83 MeO H 2-Me OCH₂ 6-Cl O O G1.84 Me H 2-Me OCH₂ 7-Cl O S G1.85 MeO H 2-Me OCH₂ 7-Cl O S 135-137 G1.86 MeO H 2-Me OCH₂ 7-Cl O O G1.87 Me H 2-Me OCH₂ 4-CF₃ O S 185-186 G1.88 Me H 2-Me SCH₂ 4-CF₃ O S G1.89 MeO H 2-Me OCH₂ 4-CF₃ O S 180-181 G1.90 Me H 2-Me OCH₂ 4-CF₃ O O G1.91 MeO H 2-Me OCH₂ 4-CF₃ O O G1.92 Me H 2-Me OCH₂ 5-CF₃ O S 209-210 G1.93 Me H 2-Me SCH₂ 5-CF₃ O S G1.94 MeO H 2-Me OCH₂ 5-CF₃ O S 173-176 G1.95 Me H 2-Me OCH₂ 5-CF₃ O O 216-218 G1.96 MeO H 2-Me OCH₂ 5-CF₃ O O 141-143 G1.97 Me H 2-Me OCH₂ 6-CF₃ O S 203-205 G1.98 Me H 2-Me SCH₂ 6-CF₃ O S G1.99 MeO H 2-Me OCH₂ 6-CF₃ O S 165-168 G1.100 Me H 2-Me OCH₂ 7-CF₃ O S G1.101 Me H 2-Me SCH₂ 7-CF₃ O S G1.102 Me H 2-Me OCH₂ 5-OCF₃ O S G1.103 Me H 2-Me SCH₂ 5-OCF₃ O S G1.104 MeO H 2-Me OCH₂ 5-OCF₃ O S G1.105 MeO H 2-Me OCH₂ 5-OCF₃ O O G1.106 Me H 2-Me OCH₂ 6-OCF₃ O S G1.107 Me H 2-Me SCH₂ 6-OCF₃ O S G1.108 MeO H 2-Me OCH₂ 6-OCF₃ O S G1.109 Me H 2-Me OCH₂ 5-NO₂ O O 212-216 G1.110 MeO H 2-Me OCH₂ 5-NO₂ O O G1.111 Me H 2-Me OCH₂ 4-COOMe O S G1.112 MeO H 2-Me OCH₂ 4-COOMe O S G1.113 Me H 2-Me OCH₂ 4-COOMe O O 粘土状 G1.114 MeO H 2-Me OCH₂ 4-COOMe O O 油状物 G1.115 Me H 2-Me OCH₂ 5-COOMe O S G1.116 MeO H 2-Me OCH₂ 5-COOMe O S G1.117 Me H 2-Me OCH₂ 5-COOMe O O 175-183 G1.118 MeO H 2-Me OCH₂ 5-COOMe O O 132-135 G1.119 Me H 2-Me OCH₂ 6-COOMe O S G1.120 MeO H 2-Me OCH₂ 6-COOMe O S G1.121 Me H 2-Me OCH₂ 6-COOMe O O 148-153 G1.122 MeO H 2-Me OCH₂ 6-COOMe O O 〜190 G1.123 MeO H 2-Me SCH₂ 5-F O S G1.124 MeO H 2-Me SCH₂ 5-F O O G1.125 Me H 2-Me OCH₂ 7-COOMe O S G1.126 MeO H 2-Me OCH₂ 7-COOMe O S G1.127 Me H 2-Me OCH₂ 7-COOMe O O 150-160 G1.128 MeO H 2-Me OCH₂ 7-COOMe O O 139-141 G2.1 Me H 2-Me OCH₂ 4,5-Me₂ O S G2.2 Me H 2-Me SCH₂ 4,5-Me₂ O S G2.3 MeO H 2-Me OCH₂ 4,5-Me₂ O S G2.4 Me H 2-Me OCH₂ 4,6-Me₂ O S G2.5 Me H 2-Me SCH₂ 4,6-Me₂ O S G2.6 Me H 2-Me OCH₂ 4,7-Me₂ O S G2.7 Me H 2-Me SCH₂ 4,7-Me₂ O S G2.8 Me H 2-Me OCH₂ 5,6-Me₂ O S G2.9 Me H 2-Me SCH₂ 5,6-Me₂ O S G2.10 MeO H 2-Me OCH₂ 5,6-Me₂ O S G2.11 Me H 2-Me OCH₂ 5,7-Me₂ O S G2.12 Me H 2-Me SCH₂ 5,7-Me₂ O S G2.13 Me H 2-Me OCH₂ 5,7-Me₂ O O 207-210 G2.14 MeO H 2-Me OCH₂ 5,7-Me₂ O O 154-155 G2.15 Me H 2-Me OCH₂ 6,7-Me₂ O S G2.16 Me H 2-Me SCH₂ 6,7-Me₂ O S G2.17 Me H 2-Me OCH₂ 4,5-(OMe)₂ O S G2.18 MeO H 2-Me OCH₂ 4,5-(OMe)₂ O S G2.19 Me H 2-Me OCH₂ 4,5-(OMe)₂ O S G2.20 MeO H 2-Me SCH₂ 4,5-(OMe)₂ O S G2.21 Me H 2-Me OCH₂ 4,6-(OMe)₂ O S G2.22 Me H 2-Me SCH₂ 4,6-(OMe)₂ O S G2.23 Me H 2-Me OCH₂ 4,7-(OMe)₂ O S G2.24 Me H 2-Me SCH₂ 4,7-(OMe)₂ O S G2.25 Me H 2-Me OCH₂ 5,6-(OMe)₂ O S G2.26 Me H 2-Me SCH₂ 5,6-(OMe)₂ O S G2.27 MeO H 2-Me OCH₂ 5,6-(OMe)₂ O S G2.28 Me H 2-Me OCH₂ 5,6-(OMe)₂ O O G2.29 MeO H 2-Me OCH₂ 5,6-(OMe)₂ O O G2.30 Me H 2-Me OCH₂ 5,7-(OMe)₂ O S G2.31 Me H 2-Me SCH₂ 5,7-(OMe)₂ O S G2.32 Me H 2-Me OCH₂ 6,7-(OMe)₂ O S G2.33 Me H 2-Me SCH₂ 6,7-(OMe)₂ O S G2.34 Me H 2-Me OCH₂ 4,5-F₂ O S G2.35 Me H 2-Me SCH₂ 4,5-F₂ O S G2.36 MeO H 2-Me OCH₂ 4,5-F₂ O S G2.37 Me H 2-Me OCH₂ 4,6-F₂ O S G2.38 Me H 2-Me SCH₂ 4,6-F₂ O S G2.39 MeO H 2-Me OCH₂ 4,6-F₂ O S G2.40 Me H 2-Me OCH₂ 4,7-F₂ O S G2.41 Me H 2-Me SCH₂ 4,7-F₂ O S G2.42 Me H 2-Me OCH₂ 5,6-F₂ O S 219-222 G2.43 Me H 2-Me SCH₂ 5,6-F₂ O S G2.44 MeO H 2-Me OCH₂ 5,6-F₂ O S G2.45 Me H 2-Me OCH₂ 5,7-F₂ O S G2.46 Me H 2-Me SCH₂ 5,7-F₂ O S G2.47 Me H 2-Me OCH₂ 6,7-F₂ O S G2.48 Me H 2-Me SCH₂ 6,7-F₂ O S G2.49 Me H 2-Me OCH₂ 6,7-F₂ O O 164-165 G2.50 MeO H 2-Me OCH₂ 6,7-F₂ O O 124-125 G2.51 Me H 2-Me OCH₂ 4,5-Cl₂ O S G2.52 Me H 2-Me SCH₂ 4,5-Cl₂ O S G2.53 Me H 2-Me OCH₂ 4,6-Cl₂ O S G2.54 Me H 2-Me SCH₂ 4,6-Cl₂ O S G2.55 Me H 2-Me OCH₂ 4,7-Cl₂ O S G2.56 Me H 2-Me SCH₂ 4,7-Cl₂ O S G2.57 Me H 2-Me OCH₂ 5,6-Cl₂ O S G2.58 Me H 2-Me SCH₂ 5,6-Cl₂ O S G2.59 Me H 2-Me OCH₂ 5,7-Cl₂ O S G2.60 Me H 2-Me SCH₂ 5,7-Cl₂ O S G2.61 Me H 2-Me OCH₂ 5,7-Cl₂ O O 190-193 G2.62 MeO H 2-Me OCH₂ 5,7-Cl₂ O O 130-132 G2.63 Me H 2-Me OCH₂ 6,7-Cl₂ O S G2.64 Me H 2-Me SCH₂ 6,7-Cl₂ O S G2.65 Me H 2-Me OCH₂ 4,5-(CF₃)₂ O S G2.67 Me H 2-Me SCH₂ 4,5-(CF₃)₂ O S G2.68 Me H 2-Me OCH₂ 4,6-(CF₃)₂ O S G2.69 Me H 2-Me SCH₂ 4,6-(CF₃)₂ O S G2.70 Me H 2-Me OCH₂ 4,7-(CF₃)₂ O S G2.71 Me H 2-Me SCH₂ 4,7-(CF₃)₂ O S G2.72 Me H 2-Me OCH₂ 5,6-(CF₃)₂ O S G2.73 Me H 2-Me SCH₂ 5,6-(CF₃)₂ O S G2.74 Me H 2-Me OCH₂ 5,7-(CF₃)₂ O S G2.75 Me H 2-Me SCH₂ 5,7-(CF₃)₂ O S G2.76 Me H 2-Me OCH₂ 6,7-(CF₃)₂ O S G2.77 Me H 2-Me SCH₂ 6,7-(CF₃)₂ O S G2.78 Me H 2-Me OCH₂ 4-F,5-Me O S G2.79 Me H 2-Me SCH₂ 4-F,5-Me O S G2.80 Me H 2-Me OCH₂ 4-F,6-Me O S G2.81 Me H 2-Me SCH₂ 4-F,6-Me O S G2.82 Me H 2-Me OCH₂ 4-F,7-Me O S G2.83 Me H 2-Me SCH₂ 4-F,7-Me O S G2.84 Me H 2-Me OCH₂ 4-Me,5-F O S G2.85 Me H 2-Me SCH₂ 4-Me,5-F O S G2.86 Me H 2-Me OCH₂ 5-F,6-Me O S 222-225 G2.87 Me H 2-Me SCH₂ 5-F,6-Me O S G2.88 MeO H 2-Me OCH₂ 5-F,6-Me O S G2.89 Me H 2-Me OCH₂ 5-F,6-Me O O G2.90 MeO H 2-Me OCH₂ 5-F,6-Me O O G2.91 Me H 2-Me OCH₂ 5-F,7-Me O S G2.92 Me H 2-Me SCH₂ 5-F,7-Me O S G2.93 Me H 2-Me OCH₂ 4-Me,6-F O S G2.94 Me H 2-Me SCH₂ 4-Me,6-F O S G2.95 Me H 2-Me OCH₂ 5-Me,6-F O S G2.96 Me H 2-Me SCH₂ 5-Me,6-F O S G2.97 Me H 2-Me OCH₂ 6-F,7-Me O S 191-195 G2.98 Me H 2-Me SCH₂ 6-F,7-Me O S G2.99 MeO H 2-Me OCH₂ 6-F,7-Me O S G2.100 Me H 2-Me OCH₂ 4-Me,7-F O S G2.101 Me H 2-Me SCH₂ 4-Me,7-F O S G2.102 Me H 2-Me OCH₂ 5-Me,7-F O S G2.103 Me H 2-Me SCH₂ 5-Me,7-F O S G2.104 Me H 2-Me OCH₂ 6-Me,7-F O S G2.105 Me H 2-Me SCH₂ 6-Me,7-F O S G2.106 Me H 2-Me OCH₂ 4-Cl,5-Me O S G2.107 Me H 2-Me SCH₂ 4-Cl,5-Me O S G2.108 MeO H 2-Me OCH₂ 4-Cl,5-Me O S G2.109 Me H 2-Me OCH₂ 4-Cl,6-Me O S G2.110 Me H 2-Me SCH₂ 4-Cl,6-Me O S G2.111 Me H 2-Me OCH₂ 4-Cl,7-Me O S G2.112 Me H 2-Me SCH₂ 4-Cl,7-Me O S G2.113 Me H 2-Me OCH₂ 4-Me,5-Cl O S G2.114 Me H 2-Me SCH₂ 4-Me,5-Cl O S G2.115 Me H 2-Me OCH₂ 5-Cl,6-Me O S 249-251 G2.116 Me H 2-Me SCH₂ 5-Cl,6-Me O S G2.117 MeO H 2-Me OCH₂ 5-Cl,6-Me O S G2.118 Me H 2-Me OCH₂ 5-Cl,6-Me O O G2.119 MeO H 2-Me OCH₂ 5-Cl,6-Me O O G2.120 Me H 2-Me OCH₂ 5-Cl,7-Me O S G2.121 Me H 2-Me SCH₂ 5-Cl,7-Me O S G2.122 Me H 2-Me OCH₂ 4-Me,6-Cl O S G2.123 Me H 2-Me SCH₂ 4-Me,6-Cl O S G2.124 Me H 2-Me OCH₂ 5-Me,6-Cl O S G2.125 Me H 2-Me SCH₂ 5-Me,6-Cl O S G2.126 Me H 2-Me OCH₂ 6-Cl,7-Me O S G2.127 Me H 2-Me SCH₂ 6-Cl,7-Me O S G2.128 Me H 2-Me OCH₂ 4-Me,7-Cl O S G2.129 Me H 2-Me SCH₂ 4-Me,7-Cl O S G2.130 Me H 2-Me OCH₂ 5-Me,7-Cl O S G2.131 Me H 2-Me SCH₂ 5-Me,7-Cl O S G2.132 Me H 2-Me OCH₂ 6-Me,7-Cl O S G2.133 Me H 2-Me SCH₂ 6-Me,7-Cl O S G2.134 Me H 2-Me OCH₂ 4-Cl,6-OMe O S G2.135 Me H 2-Me SCH₂ 4-Cl,6-OMe O S G2.136 MeO H 2-Me OCH₂ 4-Cl,6-OMe O S G2.137 Me H 2-Me OCH₂ 5-Cl,6-OMe O S 228-230 G2.138 Me H 2-Me SCH₂ 5-Cl,6-OMe O S G2.139 MeO H 2-Me OCH₂ 5-Cl,6-OMe O S G2.140 Me H 2-Me OCH₂ 4-Cl,5-F O S G2.141 Me H 2-Me SCH₂ 4-Cl,5-F O S G2.142 Me H 2-Me OCH₂ 4-Cl,6-F O S G2.143 Me H 2-Me SCH₂ 4-Cl,6-F O S G2.144 Me H 2-Me OCH₂ 4-Cl,7-F O S G2.145 Me H 2-Me SCH₂ 4-Cl,7-F O S G2.146 Me H 2-Me OCH₂ 4-F,5-Cl O S G2.147 Me H 2-Me SCH₂ 4-F,5-Cl O S G2.148 Me H 2-Me OCH₂ 5-Cl,6-F O S 242-245 G2.149 Me H 2-Me SCH₂ 5-Cl,6-F O S G2.150 MeO H 2-Me OCH₂ 5-Cl,6-F O S G2.151 Me H 2-Me OCH₂ 5-Cl,6-F O O G2.152 MeO H 2-Me OCH₂ 5-Cl,6-F O O G2.153 Me H 2-Me OCH₂ 5-Cl,7-F O S G2.154 Me H 2-Me SCH₂ 5-Cl,7-F O S G2.156 Me H 2-Me OCH₂ 4-F,6-Cl O S G2.157 Me H 2-Me SCH₂ 4-F,6-Cl O S G2.158 Me H 2-Me OCH₂ 5-F,6-Cl O S G2.159 Me H 2-Me SCH₂ 5-F,6-Cl O S G2.160 Me H 2-Me OCH₂ 6-Cl,7-F O S G2.161 Me H 2-Me SCH₂ 6-Cl,7-F O S G2.162 Me H 2-Me OCH₂ 4-F,7-Cl O S G2.163 Me H 2-Me SCH₂ 4-F,7-Cl O S G2.164 Me H 2-Me OCH₂ 5-F,7-Cl O S G2.165 Me H 2-Me SCH₂ 5-F,7-Cl O S G2.166 Me H 2-Me OCH₂ 6-F,7-Cl O S 218-220 G2.167 Me H 2-Me SCH₂ 6-F,7-Cl O S G2.168 MeO H 2-Me OCH₂ 6-F,7-Cl O S G3.1 Me H 3-Me OCH₂ 4-Me O S G3.2 Me H 3-Me SCH₂ 4-Me O S G3.3 Me H 3-Me OCH₂ 5-Me O S G3.4 Me H 3-Me SCH₂ 5-Me O S G3.5 Me H 3-Me OCH₂ 6-Me O S G3.6 Me H 3-Me SCH₂ 6-Me O S G3.7 Me H 3-Me OCH₂ 7-Me O S G3.8 Me H 3-Me SCH₂ 7-Me O S G3.9 Me H 3-Me OCH₂ 5-Et O S G3.10 Me H 3-Me SCH₂ 5-Et O S G3.11 Me H 3-Me OCH₂ 6-Et O S G3.12 Me H 3-Me SCH₂ 6-Et O S G3.13 Me H 3-Me OCH₂ 4-OMe O S G3.14 Me H 3-Me SCH₂ 4-OMe O S G3.15 Me H 3-Me OCH₂ 5-OMe O S G3.16 Me H 3-Me SCH₂ 5-OMe O S G3.17 Me H 3-Me OCH₂ 6-OMe O S G3.18 Me H 3-Me SCH₂ 6-OMe O S G3.19 Me H 3-Me OCH₂ 7-OMe O S G3.20 Me H 3-Me SCH₂ 7-OMe O S G3.21 Me H 3-Me OCH₂ 5-OEt O S G3.22 Me H 3-Me SCH₂ 5-OEt O S G3.23 Me H 3-Me OCH₂ 6-OEt O S G3.24 Me H 3-Me SCH₂ 6-OEt O S G3.25 Me H 3-Me OCH₂ 4-F O S G3.26 Me H 3-Me SCH₂ 4-F O S G3.27 Me H 3-Me OCH₂ 5-F O S G3.28 Me H 3-Me SCH₂ 5-F O S G3.29 Me H 3-Me OCH₂ 6-F O S G3.30 Me H 3-Me SCH₂ 6-F O S G3.31 Me H 3-Me OCH₂ 7-F O S G3.32 Me H 3-Me SCH₂ 7-F O S G3.33 Me H 3-Me OCH₂ 5-Cl O S G3.34 Me H 3-Me SCH₂ 5-Cl O S G3.35 Me H 3-Me OCH₂ 6-Cl O S G3.36 Me H 3-Me SCH₂ 6-Cl O S G3.37 Me H 3-Me OCH₂ 4-CF₃ O S G3.38 Me H 3-Me SCH₂ 4-CF₃ O S G3.39 Me H 3-Me OCH₂ 5-CF₃ O S G3.40 Me H 3-Me SCH₂ 5-CF₃ O S G3.41 Me H 3-Me OCH₂ 6-CF₃ O S G3.42 Me H 3-Me SCH₂ 6-CF₃ O S G3.45 Me H 3-Me SCH₂ 7-CF₃ O S G3.46 Me H 3-Me OCH₂ 5-OCF₃ O S G3.47 Me H 3-Me SCH₂ 5-OCF₃ O S G3.48 Me H 3-Me OCH₂ 6-OCF₃ O S G3.49 Me H 3-Me SCH₂ 6-OCF₃ O S G3.50 Me H 3-Me OCH₂ 4,5-Me₂ O S G3.51 Me H 3-Me SCH₂ 4,5-Me₂ O S G3.52 Me H 3-Me OCH₂ 4,6-Me₂ O S G3.53 Me H 3-Me SCH₂ 4,6-Me₂ O S G3.54 Me H 3-Me OCH₂ 4,7-Me₂ O S G3.55 Me H 3-Me SCH₂ 4,7-Me₂ O S G3.56 Me H 3-Me OCH₂ 5,6-Me₂ O S G3.57 Me H 3-Me SCH₂ 5,6-Me₂ O S G3.58 Me H 3-Me OCH₂ 5,7-Me₂ O S G3.59 Me H 3-Me SCH₂ 5,7-Me₂ O S G3.60 Me H 3-Me OCH₂ 6,7-Me₂ O S G3.61 Me H 3-Me SCH₂ 6,7-Me₂ O S G3.62 Me H 3-Me OCH₂ 4,5-(OMe)₂ O S G3.63 Me H 3-Me SCH₂ 4,5-(OMe)₂ O S G3.64 Me H 3-Me OCH₂ 4,6-(OMe)₂ O S G3.65 Me H 3-Me SCH₂ 4,6-(OMe)₂ O S G3.66 Me H 3-Me OCH₂ 4,7-(OMe)₂ O S G3.67 Me H 3-Me SCH₂ 4,7-(OMe)₂ O S G3.68 Me H 3-Me OCH₂ 5,6-(OMe)₂ O S G3.69 Me H 3-Me SCH₂ 5,6-(OMe)₂ O S G3.70 Me H 3-Me OCH₂ 5,7-(OMe)₂ O S G3.71 Me H 3-Me SCH₂ 5,7-(OMe)₂ O S G3.72 Me H 3-Me OCH₂ 6,7-(OMe)₂ O S G3.73 Me H 3-Me SCH₂ 6,7-(OMe)₂ O S G3.74 Me H 3-Me OCH₂ 4,5-F₂ O S G3.75 Me H 3-Me SCH₂ 4,5-F₂ O S G3.76 Me H 3-Me OCH₂ 4,6-F₂ O S G3.77 Me H 3-Me SCH₂ 4,6-F₂ O S G3.78 Me H 3-Me OCH₂ 4,7-F₂ O S G3.79 Me H 3-Me SCH₂ 4,7-F₂ O S G3.80 Me H 3-Me OCH₂ 5,6-F₂ O S G3.81 Me H 3-Me SCH₂ 5,6-F₂ O S G3.82 Me H 3-Me OCH₂ 5,7-F₂ O S G3.83 Me H 3-Me SCH₂ 5,7-F₂ O S G3.84 Me H 3-Me OCH₂ 6,7-F₂ O S G3.85 Me H 3-Me SCH₂ 6,7-F₂ O S G3.86 Me H 3-Me OCH₂ 4,5-Cl₂ O S G3.87 Me H 3-Me SCH₂ 4,5-Cl₂ O S G3.88 Me H 3-Me OCH₂ 4,6-Cl₂ O S G3.89 Me H 3-Me SCH₂ 4,6-Cl₂ O S G3.90 Me H 3-Me OCH₂ 4,7-Cl₂ O S G3.91 Me H 3-Me SCH₂ 4,7-Cl₂ O S G3.92 Me H 3-Me OCH₂ 5,6-Cl₂ O S G3.93 Me H 3-Me SCH₂ 5,6-Cl₂ O S G3.94 Me H 3-Me OCH₂ 5,7-Cl₂ O S G3.95 Me H 3-Me SCH₂ 5,7-Cl₂ O S G3.96 Me H 3-Me OCH₂ 6,7-Cl₂ O S G3.97 Me H 3-Me SCH₂ 6,7-Cl₂ O S G3.98 Me H 3-Me OCH₂ 4,5-(CF₃)₂ O S G3.99 Me H 3-Me SCH₂ 4,5-(CF₃)₂ O S G3.100 Me H 3-Me OCH₂ 4,6-(CF₃)₂ O S G3.101 Me H 3-Me SCH₂ 4,6-(CF₃)₂ O S G3.102 Me H 3-Me OCH₂ 4,7-(CF₃)₂ O S G3.103 Me H 3-Me SCH₂ 4,7-(CF₃)₂ O S G3.104 Me H 3-Me OCH₂ 5,6-(CF₃)₂ O S G3.105 Me H 3-Me SCH₂ 5,6-(CF₃)₂ O S G3.106 Me H 3-Me OCH₂ 5,7-(CF₃)₂ O S G3.107 Me H 3-Me SCH₂ 5,7-(CF₃)₂ O S G3.108 Me H 3-Me OCH₂ 6,7-(CF₃)₂ O S G3.109 Me H 3-Me SCH₂ 6,7-(CF₃)₂ O S G4.1 Me H 3-Me OCH₂ 4-F,5-Me O S G4.2 Me H 3-Me SCH₂ 4-F,5-Me O S G4.3 Me H 3-Me OCH₂ 4-F,6-Me O S G4.4 Me H 3-Me SCH₂ 4-F,6-Me O S G4.5 Me H 3-Me OCH₂ 4-F,7-Me O S G4.6 Me H 3-Me SCH₂ 4-F,7-Me O S G4.7 Me H 3-Me OCH₂ 4-Me,5-F O S G4.8 Me H 3-Me SCH₂ 4-Me,5-F O S G4.9 Me H 3-Me OCH₂ 5-F,6-Me O S G4.10 Me H 3-Me SCH₂ 5-F,6-Me O S G4.11 Me H 3-Me OCH₂ 5-F,7-Me O S G4.12 Me H 3-Me SCH₂ 5-F,7-Me O S G4.13 Me H 3-Me OCH₂ 4-Me,6-F O S G4.14 Me H 3-Me SCH₂ 4-Me,6-F O S G4.15 Me H 3-Me OCH₂ 5-Me,6-F O S G4.16 Me H 3-Me SCH₂ 5-Me,6-F O S G4.17 Me H 3-Me OCH₂ 6-F,7-Me O S G4.18 Me H 3-Me SCH₂ 6-F,7-Me O S G4.19 Me H 3-Me OCH₂ 4-Me,7-F O S G4.20 Me H 3-Me SCH₂ 4-Me,7-F O S G4.21 Me H 3-Me OCH₂ 5-Me,7-F O S G4.22 Me H 3-Me SCH₂ 5-Me,7-F O S G4.23 Me H 3-Me OCH₂ 6-Me,7-F O S G4.24 Me H 3-Me SCH₂ 6-Me,7-F O S G4.25 Me H 3-Me OCH₂ 4-Cl,5-Me O S G4.26 Me H 3-Me SCH₂ 4-Cl,5-Me O S G4.27 Me H 3-Me OCH₂ 4-Cl,6-Me O S G4.28 Me H 3-Me SCH₂ 4-Cl,6-Me O S G4.29 Me H 3-Me OCH₂ 4-Cl,7-Me O S G4.30 Me H 3-Me SCH₂ 4-Cl,7-Me O S G4.31 Me H 3-Me OCH₂ 4-Me,5-Cl O S G4.32 Me H 3-Me SCH₂ 4-Me,5-Cl O S G4.33 Me H 3-Me OCH₂ 5-Cl,6-Me O S G4.34 Me H 3-Me SCH₂ 5-Cl,6-Me O S G4.35 Me H 3-Me OCH₂ 5-Cl,7-Me O S G4.36 Me H 3-Me SCH₂ 5-Cl,7-Me O S G4.37 Me H 3-Me OCH₂ 4-Me,6-Cl O S G4.38 Me H 3-Me SCH₂ 4-Me,6-Cl O S G4.39 Me H 3-Me OCH₂ 5-Me,6-Cl O S G4.40 Me H 3-Me SCH₂ 5-Me,6-Cl O S G4.41 Me H 3-Me OCH₂ 6-Cl,7-Me O S G4.42 Me H 3-Me SCH₂ 6-Cl,7-Me O S G4.43 Me H 3-Me OCH₂ 4-Me,7-Cl O S G4.44 Me H 3-Me SCH₂ 4-Me,7-Cl O S G4.45 Me H 3-Me OCH₂ 5-Me,7-Cl O S G4.46 Me H 3-Me SCH₂ 5-Me,7-Cl O S G4.47 Me H 3-Me OCH₂ 6-Me,7-Cl O S G4.48 Me H 3-Me SCH₂ 6-Me,7-Cl O S G4.49 Me H 3-Me OCH₂ 4-Cl,5-F O S G4.50 Me H 3-Me SCH₂ 4-Cl,5-F O S G4.51 Me H 3-Me OCH₂ 4-Cl,6-F O S G4.52 Me H 3-Me SCH₂ 4-Cl,6-F O S G4.53 Me H 3-Me OCH₂ 4-Cl,7-F O S G4.54 Me H 3-Me SCH₂ 4-Cl,7-F O S G4.55 Me H 3-Me OCH₂ 4-F,5-Cl O S G4.56 Me H 3-Me SCH₂ 4-F,5-Cl O S G4.57 Me H 3-Me OCH₂ 5-Cl,6-F O S G4.58 Me H 3-Me SCH₂ 5-Cl,6-F O S G4.59 Me H 3-Me OCH₂ 5-Cl,7-F O S G4.60 Me H 3-Me SCH₂ 5-Cl,7-F O S G4.61 Me H 3-Me OCH₂ 4-F,6-Cl O S G4.62 Me H 3-Me SCH₂ 4-F,6-Cl O S G4.63 Me H 3-Me OCH₂ 5-F,6-Cl O S G4.64 Me H 3-Me SCH₂ 5-F,6-Cl O S G4.65 Me H 3-Me OCH₂ 6-Cl,7-F O S G4.66 Me H 3-Me SCH₂ 6-Cl,7-F O S G4.67 Me H 3-Me OCH₂ 4-F,7-Cl O S G4.68 Me H 3-Me SCH₂ 4-F,7-Cl O S G4.69 Me H 3-Me OCH₂ 5-F,7-Cl O S G4.70 Me H 3-Me SCH₂ 5-F,7-Cl O S G4.71 Me H 3-Me OCH₂ 6-F,7-Cl O S G4.72 Me H 3-Me SCH₂ 6-F,7-Cl O S G5.1 Me H 2-Et OCH₂ 4-Me O S G5.2 Me H 2-Et SCH₂ 4-Me O S G5.3 Me H 2-Et OCH₂ 5-Me O S 218-221 G5.4 Me H 2-Et SCH₂ 5-Me O S G5.5 MeO H 2-Et OCH₂ 5-Me O S G5.6 Me H 2-Et OCH₂ 6-Me O S 198-200 G5.7 Me H 2-Et SCH₂ 6-Me O S G5.8 MeO H 2-Et OCH₂ 6-Me O S G5.9 Me H 2-Et OCH₂ 7-Me O S G5.10 Me H 2-Et SCH₂ 7-Me O S G5.11 Me H 2-Et OCH₂ 5-Et O S G5.12 Me H 2-Et SCH₂ 5-Et O S G5.13 Me H 2-Et OCH₂ 6-Et O S G5.14 Me H 2-Et SCH₂ 6-Et O S G5.15 Me H 2-Et OCH₂ 4-OMe O S G5.16 Me H 2-Et SCH₂ 4-OMe O S G5.17 Me H 2-Et OCH₂ 5-OMe O S 169-172 G5.18 Me H 2-Et SCH₂ 5-OMe O S G5.19 MeO H 2-Et OCH₂ 5-OMe O S G5.20 Me H 2-Et OCH₂ 6-OMe O S 157-160 G5.21 Me H 2-Et SCH₂ 6-OMe O S G5.22 MeO H 2-Et OCH₂ 6-OMe O S G5.23 Me H 2-Et OCH₂ 6-OMe O O G5.24 MeO H 2-Et OCH₂ 6-OMe O O G5.25 Me H 2-Et OCH₂ 7-OMe O S G5.26 Me H 2-Et SCH₂ 7-OMe O S G5.27 Me H 2-Et OCH₂ 5-OEt O S G5.28 Me H 2-Et SCH₂ 5-OEt O S G5.29 Me H 2-Et OCH₂ 6-OEt O S G5.30 Me H 2-Et SCH₂ 6-OEt O S G5.31 Me H 2-Et OCH₂ 4-F O S G5.32 Me H 2-Et SCH₂ 4-F O S G5.33 Me H 2-Et OCH₂ 5-F O S 197-198 G5.34 Me H 2-Et SCH₂ 5-F O S G5.35 MeO H 2-Et OCH₂ 5-F O S G5.36 Me H 2-Et OCH₂ 5-F O O G5.37 MeO H 2-Et OCH₂ 5-F O O G5.38 Me H 2-Et OCH₂ 6-F O S 198-200 G5.39 Me H 2-Et SCH₂ 6-F O S G5.40 MeO H 2-Et OCH₂ 6-F O S G5.41 Me H 2-Et OCH₂ 6-F O O G5.42 MeO H 2-Et OCH₂ 6-F O O G5.43 Me H 2-Et OCH₂ 7-F O S G5.44 Me H 2-Et SCH₂ 7-F O S G5.45 Me H 2-Et OCH₂ 5-Cl O S 210-213 G5.46 Me H 2-Et SCH₂ 5-Cl O S G5.47 MeO H 2-Et OCH₂ 5-Cl O S G5.48 Me H 2-Et OCH₂ 6-Cl O S G5.49 Me H 2-Et SCH₂ 6-Cl O S G5.50 Me H 2-Et OCH₂ 4-CF₃ O S G5.51 Me H 2-Et SCH₂ 4-CF₃ O S G5.52 Me H 2-Et OCH₂ 5-CF₃ O S 210-212 G5.53 Me H 2-Et SCH₂ 5-CF₃ O S G5.54 MeO H 2-Et OCH₂ 5-CF₃ O S G5.55 Me H 2-Et OCH₂ 6-CF₃ O S G5.56 Me H 2-Et SCH₂ 6-CF₃ O S G5.57 Me H 2-Et OCH₂ 7-CF₃ O S G5.58 Me H 2-Et SCH₂ 7-CF₃ O S G5.59 Me H 2-Et OCH₂ 5-OCF₃ O S G5.60 Me H 2-Et SCH₂ 5-OCF₃ O S G5.61 Me H 2-Et OCH₂ 6-OCF₃ O S G5.62 Me H 2-Et SCH₂ 6-OCF₃ O S G6.1 Me H 2-Et OCH₂ 4,5-Me₂ O S G6.2 Me H 2-Et SCH₂ 4,5-Me₂ O S G6.3 Me H 2-Et OCH₂ 4,6-Me₂ O S G6.4 Me H 2-Et SCH₂ 4,6-Me₂ O S G6.5 Me H 2-Et OCH₂ 4,7-Me₂ O S G6.6 Me H 2-Et SCH₂ 4,7-Me₂ O S G6.7 Me H 2-Et OCH₂ 5,6-Me₂ O S G6.8 Me H 2-Et SCH₂ 5,6-Me₂ O S G6.9 Me H 2-Et OCH₂ 5,7-Me₂ O S G6.10 Me H 2-Et SCH₂ 5,7-Me₂ O S G6.11 Me H 2-Et OCH₂ 6,7-Me₂ O S G6.12 Me H 2-Et SCH₂ 6,7-Me₂ O S G6.13 Me H 2-Et OCH₂ 4,5-(OMe)₂ O S G6.14 Me H 2-Et SCH₂ 4,5-(OMe)₂ O S G6.15 Me H 2-Et OCH₂ 4,6-(OMe)₂ O S G6.16 Me H 2-Et SCH₂ 4,6-(OMe)₂ O S G6.17 Me H 2-Et OCH₂ 4,7-(OMe)₂ O S G6.18 Me H 2-Et SCH₂ 4,7-(OMe)₂ O S G6.19 Me H 2-Et OCH₂ 5,6-(OMe)₂ O S G6.20 Me H 2-Et SCH₂ 5,6-(OMe)₂ O S G6.21 Me H 2-Et OCH₂ 5,7-(OMe)₂ O S G6.22 Me H 2-Et SCH₂ 5,7-(OMe)₂ O S G6.23 Me H 2-Et OCH₂ 6,7-(OMe)₂ O S G6.24 Me H 2-Et SCH₂ 6,7-(OMe)₂ O S G6.25 Me H 2-Et OCH₂ 4,5-F₂ O S G6.26 Me H 2-Et SCH₂ 4,5-F₂ O S G6.27 Me H 2-Et OCH₂ 4,6-F₂ O S G6.28 Me H 2-Et SCH₂ 4,6-F₂ O S G6.29 Me H 2-Et OCH₂ 4,7-F₂ O S G6.30 Me H 2-Et SCH₂ 4,7-F₂ O S G6.31 Me H 2-Et OCH₂ 5,6-F₂ O S 213-214 G6.32 Me H 2-Et SCH₂ 5,6-F₂ O S G6.33 MeO H 2-Et OCH₂ 5,6-F₂ O S G6.34 Me H 2-Et OCH₂ 5,7-F₂ O S G6.35 Me H 2-Et SCH₂ 5,7-F₂ O S G6.36 Me H 2-Et OCH₂ 6,7-F₂ O S G6.37 Me H 2-Et SCH₂ 6,7-F₂ O S G6.38 Me H 2-Et OCH₂ 4,5-Cl₂ O S G6.39 Me H 2-Et SCH₂ 4,5-Cl₂ O S G6.40 Me H 2-Et OCH₂ 4,6-Cl₂ O S G6.41 Me H 2-Et SCH₂ 4,6-Cl₂ O S G6.42 Me H 2-Et OCH₂ 4,7-Cl₂ O S G6.43 Me H 2-Et SCH₂ 4,7-Cl₂ O S G6.44 Me H 2-Et OCH₂ 5,6-Cl₂ O S G6.45 Me H 2-Et SCH₂ 5,6-Cl₂ O S G6.46 Me H 2-Et OCH₂ 5,7-Cl₂ O S G6.47 Me H 2-Et SCH₂ 5,7-Cl₂ O S G6.48 Me H 2-Et OCH₂ 6,7-Cl₂ O S G6.49 Me H 2-Et SCH₂ 6,7-Cl₂ O S G6.50 Me H 2-Et OCH₂ 4,5-(CF₃)₂ O S G6.51 Me H 2-Et SCH₂ 4,5-(CF₃)₂ O S G6.52 Me H 2-Et OCH₂ 4,6-(CF₃)₂ O S G6.53 Me H 2-Et SCH₂ 4,6-(CF₃)₂ O S G6.54 Me H 2-Et OCH₂ 4,7-(CF₃)₂ O S G6.55 Me H 2-Et SCH₂ 4,7-(CF₃)₂ O S G6.56 Me H 2-Et OCH₂ 5,6-(CF₃)₂ O S G6.57 Me H 2-Et SCH₂ 5,6-(CF₃)₂ O S G6.58 Me H 2-Et OCH₂ 5,7-(CF₃)₂ O S G6.59 Me H 2-Et SCH₂ 5,7-(CF₃)₂ O S G6.60 Me H 2-Et OCH₂ 6,7-(CF₃)₂ O S G6.61 Me H 2-Et SCH₂ 6,7-(CF₃)₂ O S G6.62 Me H 2-Et OCH₂ 4-F,5-Me O S G6.63 Me H 2-Et SCH₂ 4-F,5-Me O S G6.64 Me H 2-Et OCH₂ 4-F,6-Me O S G6.65 Me H 2-Et SCH₂ 4-F,6-Me O S G6.66 Me H 2-Et OCH₂ 4-F,7-Me O S G6.67 Me H 2-Et SCH₂ 4-F,7-Me O S G6.68 Me H 2-Et OCH₂ 4-Me,5-F O S G6.69 Me H 2-Et SCH₂ 4-Me,5-F O S G6.70 Me H 2-Et OCH₂ 5-F,6-Me O S G6.71 Me H 2-Et SCH₂ 5-F,6-Me O S G6.72 Me H 2-Et OCH₂ 5-F,7-Me O S G6.73 Me H 2-Et SCH₂ 5-F,7-Me O S G6.74 Me H 2-Et OCH₂ 4-Me,6-F O S G6.75 Me H 2-Et SCH₂ 4-Me,6-F O S G6.76 Me H 2-Et OCH₂ 5-Me,6-F O S G6.77 Me H 2-Et SCH₂ 5-Me,6-F O S G6.78 Me H 2-Et OCH₂ 6-F,7-Me O S G6.79 Me H 2-Et SCH₂ 6-F,7-Me O S G6.80 Me H 2-Et OCH₂ 4-Me,7-F O S G6.81 Me H 2-Et SCH₂ 4-Me,7-F O S G6.82 Me H 2-Et OCH₂ 5-Me,7-F O S G6.83 Me H 2-Et SCH₂ 5-Me,7-F O S G6.84 Me H 2-Et OCH₂ 6-Me,7-F O S G6.85 Me H 2-Et SCH₂ 6-Me,7-F O S G6.86 Me H 2-Et OCH₂ 4-Cl,5-Me O S G6.87 Me H 2-Et SCH₂ 4-Cl,5-Me O S G6.88 Me H 2-Et OCH₂ 4-Cl,6-Me O S G6.89 Me H 2-Et SCH₂ 4-Cl,6-Me O S G6.90 Me H 2-Et OCH₂ 4-Cl,7-Me O S G6.92 Me H 2-Et OCH₂ 4-Me,5-Cl O S G6.93 Me H 2-Et SCH₂ 4-Me,5-Cl O S G6.94 Me H 2-Et OCH₂ 5-Cl,6-Me O S G6.95 Me H 2-Et SCH₂ 5-Cl,6-Me O S G6.96 Me H 2-Et OCH₂ 5-Cl,7-Me O S G6.97 Me H 2-Et SCH₂ 5-Cl,7-Me O S G6.98 Me H 2-Et OCH₂ 4-Me,6-Cl O S G6.99 Me H 2-Et SCH₂ 4-Me,6-Cl O S G6.100 Me H 2-Et OCH₂ 5-Me,6-Cl O S G6.101 Me H 2-Et SCH₂ 5-Me,6-Cl O S G6.102 Me H 2-Et OCH₂ 6-Cl,7-Me O S G6.103 Me H 2-Et SCH₂ 6-Cl,7-Me O S G6.104 Me H 2-Et OCH₂ 4-Me,7-Cl O S G6.105 Me H 2-Et SCH₂ 4-Me,7-Cl O S G6.106 Me H 2-Et OCH₂ 5-Me,7-Cl O S G6.107 Me H 2-Et SCH₂ 5-Me,7-Cl O S G6.108 Me H 2-Et OCH₂ 6-Me,7-Cl O S G6.109 Me H 2-Et SCH₂ 6-Me,7-Cl O S G6.110 Me H 2-Et OCH₂ 4-Cl,5-F O S G6.111 Me H 2-Et SCH₂ 4-Cl,5-F O S G6.112 Me H 2-Et OCH₂ 4-Cl,6-F O S G6.113 Me H 2-Et SCH₂ 4-Cl,6-F O S G6.114 Me H 2-Et OCH₂ 4-Cl,7-F O S G6.115 Me H 2-Et SCH₂ 4-Cl,7-F O S G6.116 Me H 2-Et OCH₂ 4-F,5-Cl O S G6.117 Me H 2-Et SCH₂ 4-F,5-Cl O S G6.118 Me H 2-Et OCH₂ 5-Cl,6-F O S G6.119 Me H 2-Et SCH₂ 5-Cl,6-F O S G6.120 Me H 2-Et OCH₂ 5-Cl,7-F O S G6.121 Me H 2-Et SCH₂ 5-Cl,7-F O S G6.122 Me H 2-Et OCH₂ 4-F,6-Cl O S G6.123 Me H 2-Et SCH₂ 4-F,6-Cl O S G6.124 Me H 2-Et OCH₂ 5-F,6-Cl O S G6.125 Me H 2-Et SCH₂ 5-F,6-Cl O S G6.126 Me H 2-Et OCH₂ 6-Cl,7-F O S G6.127 Me H 2-Et SCH₂ 6-Cl,7-F O S G6.128 Me H 2-Et OCH₂ 4-F,7-Cl O S G6.129 Me H 2-Et SCH₂ 4-F,7-Cl O S G6.130 Me H 2-Et OCH₂ 5-F,7-Cl O S G6.131 Me H 2-Et SCH₂ 5-F,7-Cl O S G6.132 Me H 2-Et OCH₂ 6-F,7-Cl O S G6.133 Me H 2-Et SCH₂ 6-F,7-Cl O S G7.1 Me H 3-Et OCH₂ 4-Me O S G7.2 Me H 3-Et SCH₂ 4-Me O S G7.3 Me H 3-Et OCH₂ 5-Me O S G7.4 Me H 3-Et SCH₂ 5-Me O S G7.5 Me H 3-Et OCH₂ 6-Me O S G7.6 Me H 3-Et SCH₂ 6-Me O S G7.7 Me H 3-Et OCH₂ 7-Me O S G7.8 Me H 3-Et SCH₂ 7-Me O S G7.9 Me H 3-Et OCH₂ 5-Et O S G7.10 Me H 3-Et SCH₂ 5-Et O S G7.11 Me H 3-Et OCH₂ 6-Et O S G7.12 Me H 3-Et SCH₂ 6-Et O S G7.13 Me H 3-Et OCH₂ 4-OMe O S G7.14 Me H 3-Et SCH₂ 4-OMe O S G7.15 Me H 3-Et OCH₂ 5-OMe O S G7.16 Me H 3-Et SCH₂ 5-OMe O S G7.17 Me H 3-Et OCH₂ 6-OMe O S G7.18 Me H 3-Et SCH₂ 6-OMe O S G7.19 Me H 3-Et OCH₂ 7-OMe O S G7.20 Me H 3-Et SCH₂ 7-OMe O S G7.21 Me H 3-Et OCH₂ 5-OEt O S G7.22 Me H 3-Et SCH₂ 5-OEt O S G7.23 Me H 3-Et OCH₂ 6-OEt O S G7.24 Me H 3-Et SCH₂ 6-OEt O S G7.25 Me H 3-Et OCH₂ 4-F O S G7.26 Me H 3-Et SCH₂ 4-F O S G7.27 Me H 3-Et OCH₂ 5-F O S G7.28 Me H 3-Et SCH₂ 5-F O S G7.29 Me H 3-Et OCH₂ 6-F O S G7.30 Me H 3-Et SCH₂ 6-F O S G7.31 Me H 3-Et OCH₂ 7-F O S G7.32 Me H 3-Et SCH₂ 7-F O S G7.33 Me H 3-Et OCH₂ 5-Cl O S G7.34 Me H 3-Et SCH₂ 5-Cl O S G7.35 Me H 3-Et OCH₂ 6-Cl O S G7.36 Me H 3-Et SCH₂ 6-Cl O S G7.37 Me H 3-Et OCH₂ 4-CF₃ O S G7.38 Me H 3-Et SCH₂ 4-CF₃ O S G7.39 Me H 3-Et OCH₂ 5-CF₃ O S G7.40 Me H 3-Et SCH₂ 5-CF₃ O S G7.41 Me H 3-Et OCH₂ 6-CF₃ O S G7.42 Me H 3-Et SCH₂ 6-CF₃ O S G7.43 Me H 3-Et OCH₂ 7-CF₃ O S G7.44 Me H 3-Et SCH₂ 7-CF₃ O S G7.45 Me H 3-Et OCH₂ 5-OCF₃ O S G7.46 Me H 3-Et SCH₂ 5-OCF₃ O S G7.47 Me H 3-Et OCH₂ 6-OCF₃ O S G7.48 Me H 3-Et SCH₂ 6-OCF₃ O S G7.49 Me H 2-nPr OCH₂ 4-Me O S G7.50 Me H 2-nPr SCH₂ 4-Me O S G7.51 Me H 2-nPr OCH₂ 5-Me O S G7.52 Me H 2-nPr SCH₂ 5-Me O S G7.53 Me H 2-nPr OCH₂ 6-Me O S G7.54 Me H 2-nPr SCH₂ 6-Me O S G7.55 Me H 2-nPr OCH₂ 7-Me O S G7.56 Me H 2-nPr SCH₂ 7-Me O S G7.57 Me H 2-nPr OCH₂ 5-Et O S G7.58 Me H 2-nPr SCH₂ 5-Et O S G7.59 Me H 2-nPr OCH₂ 6-Et O S G7.60 Me H 2-nPr SCH₂ 6-Et O S G7.61 Me H 2-nPr OCH₂ 4-OMe O S G7.62 Me H 2-nPr SCH₂ 4-OMe O S G7.63 Me H 2-nPr OCH₂ 5-OMe O S G7.64 Me H 2-nPr SCH₂ 5-OMe O S G7.65 Me H 2-nPr OCH₂ 6-OMe O S G7.66 Me H 2-nPr SCH₂ 6-OMe O S G7.67 Me H 2-nPr OCH₂ 7-OMe O S G7.68 Me H 2-nPr SCH₂ 7-OMe O S G7.69 Me H 2-nPr OCH₂ 5-OEt O S G7.70 Me H 2-nPr SCH₂ 5-OEt O S G7.71 Me H 2-nPr OCH₂ 6-OEt O S G7.72 Me H 2-nPr SCH₂ 6-OEt O S G7.73 Me H 2-nPr OCH₂ 4-F O S G7.74 Me H 2-nPr SCH₂ 4-F O S G7.75 Me H 2-nPr OCH₂ 5-F O S G7.76 Me H 2-nPr SCH₂ 5-F O S G7.77 Me H 2-nPr OCH₂ 6-F O S G7.78 Me H 2-nPr SCH₂ 6-F O S G7.79 Me H 2-nPr OCH₂ 7-F O S G7.80 Me H 2-nPr SCH₂ 7-F O S G7.81 Me H 2-nPr OCH₂ 5-Cl O S G7.82 Me H 2-nPr SCH₂ 5-Cl O S G7.83 Me H 2-nPr OCH₂ 6-Cl O S G7.84 Me H 2-nPr SCH₂ 6-Cl O S G7.85 Me H 2-nPr OCH₂ 4-CF₃ O S G7.86 Me H 2-nPr SCH₂ 4-CF₃ O S G7.87 Me H 2-nPr OCH₂ 5-CF₃ O S G7.88 Me H 2-nPr SCH₂ 5-CF₃ O S G7.89 Me H 2-nPr OCH₂ 6-CF₃ O S G7.90 Me H 2-nPr SCH₂ 6-CF₃ O S G7.91 Me H 2-nPr OCH₂ 7-CF₃ O S G7.92 Me H 2-nPr SCH₂ 7-CF₃ O S G7.93 Me H 2-nPr OCH₂ 5-OCF₃ O S G7.94 Me H 2-nPr SCH₂ 5-OCF₃ O S G7.95 Me H 2-nPr OCH₂ 6-OCF₃ O S G7.96 Me H 2-nPr SCH₂ 6-OCF₃ O S G7.97 Me H 3-nPr OCH₂ 4-Me O S G7.98 Me H 3-nPr SCH₂ 4-Me O S G7.99 Me H 3-nPr OCH₂ 5-Me O S G7.100 Me H 3-nPr SCH₂ 5-Me O S G7.101 Me H 3-nPr OCH₂ 6-Me O S G7.102 Me H 3-nPr SCH₂ 6-Me O S G7.103 Me H 3-nPr OCH₂ 7-Me O S G7.104 Me H 3-nPr SCH₂ 7-Me O S G7.105 Me H 3-nPr OCH₂ 5-Et O S G7.106 Me H 3-nPr SCH₂ 5-Et O S G7.107 Me H 3-nPr OCH₂ 6-Et O S G7.108 Me H 3-nPr SCH₂ 6-Et O S G7.109 Me H 3-nPr OCH₂ 4-OMe O S G7.110 Me H 3-nPr SCH₂ 4-OMe O S G7.111 Me H 3-nPr OCH₂ 5-OMe O S G7.112 Me H 3-nPr SCH₂ 5-OMe O S G7.113 Me H 3-nPr OCH₂ 6-OMe O S G7.114 Me H 3-nPr SCH₂ 6-OMe O S G7.115 Me H 3-nPr OCH₂ 7-OMe O S G7.116 Me H 3-nPr SCH₂ 7-OMe O S G7.117 Me H 3-nPr OCH₂ 5-OEt O S G7.118 Me H 3-nPr SCH₂ 5-OEt O S G7.119 Me H 3-nPr OCH₂ 6-OEt O S G7.120 Me H 3-nPr SCH₂ 6-OEt O S G7.121 Me H 3-nPr OCH₂ 4-F O S G7.122 Me H 3-nPr SCH₂ 4-F O S G7.123 Me H 3-nPr OCH₂ 5-F O S G7.124 Me H 3-nPr SCH₂ 5-F O S G7.125 Me H 3-nPr OCH₂ 6-F O S G7.126 Me H 3-nPr SCH₂ 6-F O S G7.127 Me H 3-nPr OCH₂ 7-F O S G7.128 Me H 3-nPr SCH₂ 7-F O S G7.129 Me H 3-nPr OCH₂ 5-Cl O S G7.130 Me H 3-nPr SCH₂ 5-Cl O S G7.131 Me H 3-nPr OCH₂ 6-Cl O S G7.132 Me H 3-nPr SCH₂ 6-Cl O S G7.133 Me H 3-nPr OCH₂ 4-CF₃ O S G7.134 Me H 3-nPr SCH₂ 4-CF₃ O S G7.135 Me H 3-nPr OCH₂ 5-CF₃ O S G7.136 Me H 3-nPr SCH₂ 5-CF₃ O S G7.137 Me H 3-nPr OCH₂ 6-CF₃ O S G7.138 Me H 3-nPr SCH₂ 6-CF₃ O S G7.139 Me H 3-nPr OCH₂ 7-CF₃ O S G7.140 Me H 3-nPr SCH₂ 7-CF₃ O S G7.141 Me H 3-nPr OCH₂ 5-OCF₃ O S G7.142 Me H 3-nPr SCH₂ 5-OCF₃ O S G7.143 Me H 3-nPr OCH₂ 6-OCF₃ O S G7.144 Me H 3-nPr SCH₂ 6-OCF₃ O S G8.1 Me H 2-OMe OCH₂ 4-Me O S G8.2 Me H 2-OMe SCH₂ 4-Me O S G8.3 Me H 2-OMe OCH₂ 5-Me O S G8.4 Me H 2-OMe SCH₂ 5-Me O S G8.5 MeO H 2-OMe OCH₂ 5-Me O S G8.6 Me H 2-OMe OCH₂ 6-Me O S G8.7 Me H 2-OMe SCH₂ 6-Me O S G8.8 MeO H 2-OMe OCH₂ 6-Me O S G8.9 Me H 2-OMe OCH₂ 7-Me O S G8.10 Me H 2-OMe SCH₂ 7-Me O S G8.11 Me H 2-OMe OCH₂ 5-Et O S G8.12 Me H 2-OMe SCH₂ 5-Et O S G8.13 Me H 2-OMe OCH₂ 6-Et O S G8.14 Me H 2-OMe SCH₂ 6-Et O S G8.15 Me H 2-OMe OCH₂ 4-OMe O S G8.16 Me H 2-OMe SCH₂ 4-OMe O S G8.17 Me H 2-OMe OCH₂ 5-OMe O S G8.18 Me H 2-OMe SCH₂ 5-OMe O S G8.19 Me H 2-OMe OCH₂ 6-OMe O S G8.20 Me H 2-OMe SCH₂ 6-OMe O S G8.21 Me H 2-OMe OCH₂ 7-OMe O S G8.22 Me H 2-OMe SCH₂ 7-OMe O S G8.23 Me H 2-OMe OCH₂ 5-OEt O S G8.24 Me H 2-OMe SCH₂ 5-OEt O S G8.25 Me H 2-OMe OCH₂ 6-OEt O S G8.26 Me H 2-OMe SCH₂ 6-OEt O S G8.27 Me H 2-OMe OCH₂ 4-F O S G8.28 Me H 2-OMe SCH₂ 4-F O S G8.29 MeO H 2-OMe OCH₂ 4-F O S G8.30 MeO H 2-OMe OCH₂ 4-F O O G8.31 Me H 2-OMe OCH₂ 5-F O S 170-172 G8.32 Me H 2-OMe SCH₂ 5-F O S G8.33 MeO H 2-OMe OCH₂ 5-F O S 159-162 G8.34 Me H 2-OMe OCH₂ 5-F O O G8.35 MeO H 2-OMe OCH₂ 5-F O O G8.36 EtO H 2-OMe OCH₂ 5-F O S 157-159 G8.37 EtO H 2-OMe OCH₂ 5-F O O G8.38 Me H 2-OMe OCH₂ 6-F O S 155-159 G8.39 Me H 2-OMe SCH₂ 6-F O S G8.40 MeO H 2-OMe OCH₂ 6-F O S G8.41 MeO H 2-OMe OCH₂ 6-F O O G8.42 Me H 2-OMe OCH₂ 7-F O S G8.43 Me H 2-OMe SCH₂ 7-F O S G8.44 MeO H 2-OMe OCH₂ 7-F O S G8.45 MeO H 2-OMe OCH₂ 7-F O S G8.46 Me H 2-OMe OCH₂ 5-Cl O S G8.47 Me H 2-OMe SCH₂ 5-Cl O S G8.48 Me H 2-OMe OCH₂ 6-Cl O S G8.49 Me H 2-OMe SCH₂ 6-Cl O S G8.50 Me H 2-OMe OCH₂ 4-CF₃ O S G8.51 Me H 2-OMe SCH₂ 4-CF₃ O S G8.52 Me H 2-OMe OCH₂ 5-CF₃ O S G8.53 Me H 2-OMe SCH₂ 5-CF₃ O S G8.54 Me H 2-OMe OCH₂ 6-CF₃ O S G8.55 Me H 2-OMe SCH₂ 6-CF₃ O S G8.56 Me H 2-OMe OCH₂ 7-CF₃ O S G8.57 Me H 2-OMe SCH₂ 7-CF₃ O S G8.58 Me H 2-OMe OCH₂ 5-OCF₃ O S G8.59 Me H 2-OMe SCH₂ 5-OCF₃ O S G8.60 Me H 2-OMe OCH₂ 6-OCF₃ O S G8.61 Me H 2-OMe SCH₂ 6-OCF₃ O S G8.62 Me H 2-OMe OCH₂ 4,5-Me₂ O S G9.1 Me H 2-OMe SCH₂ 4,5-Me₂ O S G9.2 Me H 2-OMe OCH₂ 4,6-Me₂ O S G9.3 Me H 2-OMe SCH₂ 4,6-Me₂ O S G9.4 Me H 2-OMe OCH₂ 4,7-Me₂ O S G9.5 Me H 2-OMe SCH₂ 4,7-Me₂ O S G9.6 Me H 2-OMe OCH₂ 5,6-Me₂ O S G9.7 Me H 2-OMe SCH₂ 5,6-Me₂ O S G9.8 Me H 2-OMe OCH₂ 5,7-Me₂ O S G9.9 Me H 2-OMe SCH₂ 5,7-Me₂ O S G9.10 Me H 2-OMe OCH₂ 6,7-Me₂ O S G9.11 Me H 2-OMe SCH₂ 6,7-Me₂ O S G9.12 Me H 2-OMe OCH₂ 4,5-(OMe)₂ O S G9.13 Me H 2-OMe SCH₂ 4,5-(OMe)₂ O S G9.14 Me H 2-OMe OCH₂ 4,6-(OMe)₂ O S G9.15 Me H 2-OMe SCH₂ 4,6-(OMe)₂ O S G9.16 Me H 2-OMe OCH₂ 4,7-(OMe)₂ O S G9.17 Me H 2-OMe SCH₂ 4,7-(OMe)₂ O S G9.18 Me H 2-OMe OCH₂ 5,6-(OMe)₂ O S G9.19 Me H 2-OMe SCH₂ 5,6-(OMe)₂ O S G9.20 Me H 2-OMe OCH₂ 5,7-(OMe)₂ O S G9.21 Me H 2-OMe SCH₂ 5,7-(OMe)₂ O S G9.22 Me H 2-OMe OCH₂ 6,7-(OMe)₂ O S G9.23 Me H 2-OMe SCH₂ 6,7-(OMe)₂ O S G9.24 Me H 2-OMe OCH₂ 4,5-F₂ O S G9.25 Me H 2-OMe SCH₂ 4,5-F₂ O S G9.26 Me H 2-OMe OCH₂ 4,6-F₂ O S G9.27 Me H 2-OMe SCH₂ 4,6-F₂ O S G9.28 Me H 2-OMe OCH₂ 4,7-F₂ O S G9.29 Me H 2-OMe SCH₂ 4,7-F₂ O S G9.30 Me H 2-OMe OCH₂ 5,6-F₂ O S G9.31 Me H 2-OMe SCH₂ 5,6-F₂ O S G9.32 Me H 2-OMe OCH₂ 5,7-F₂ O S G9.33 Me H 2-OMe SCH₂ 5,7-F₂ O S G9.34 Me H 2-OMe OCH₂ 6,7-F₂ O S G9.35 Me H 2-OMe SCH₂ 6,7-F₂ O S G9.36 Me H 2-OMe OCH₂ 4,5-Cl₂ O S G9.37 Me H 2-OMe SCH₂ 4,5-Cl₂ O S G9.38 Me H 2-OMe OCH₂ 4,6-Cl₂ O S G9.39 Me H 2-OMe SCH₂ 4,6-Cl₂ O S G9.40 Me H 2-OMe OCH₂ 4,7-Cl₂ O S G9.41 Me H 2-OMe SCH₂ 4,7-Cl₂ O S G9.42 Me H 2-OMe OCH₂ 5,6-Cl₂ O S G9.43 Me H 2-OMe SCH₂ 5,6-Cl₂ O S G9.44 Me H 2-OMe OCH₂ 5,7-Cl₂ O S G9.45 Me H 2-OMe SCH₂ 5,7-Cl₂ O S G9.46 Me H 2-OMe OCH₂ 6,7-Cl₂ O S G9.47 Me H 2-OMe SCH₂ 6,7-Cl₂ O S G9.48 Me H 2-OMe OCH₂ 4,5-(CF₃)₂ O S G9.49 Me H 2-OMe SCH₂ 4,5-(CF₃)₂ O S G9.50 Me H 2-OMe OCH₂ 4,6-(CF₃)₂ O S G9.51 Me H 2-OMe SCH₂ 4,6-(CF₃)₂ O S G9.52 Me H 2-OMe OCH₂ 4,7-(CF₃)₂ O S G9.53 Me H 2-OMe SCH₂ 4,7-(CF₃)₂ O S G9.54 Me H 2-OMe OCH₂ 5,6-(CF₃)₂ O S G9.55 Me H 2-OMe SCH₂ 5,6-(CF₃)₂ O S G9.56 Me H 2-OMe OCH₂ 5,7-(CF₃)₂ O S G9.57 Me H 2-OMe SCH₂ 5,7-(CF₃)₂ O S G9.58 Me H 2-OMe OCH₂ 6,7-(CF₃)₂ O S G9.59 Me H 2-OMe SCH₂ 6,7-(CF₃)₂ O S G9.60 Me H 2-OMe OCH₂ 4-F,5-Me O S G9.61 Me H 2-OMe SCH₂ 4-F,5-Me O S G9.62 Me H 2-OMe OCH₂ 4-F,6-Me O S G9.63 Me H 2-OMe SCH₂ 4-F,6-Me O S G9.64 Me H 2-OMe OCH₂ 4-F,7-Me O S G9.65 Me H 2-OMe SCH₂ 4-F,7-Me O S G9.66 Me H 2-OMe OCH₂ 4-Me,5-F O S G9.67 Me H 2-OMe SCH₂ 4-Me,5-F O S G9.68 Me H 2-OMe OCH₂ 5-F,6-Me O S G9.69 Me H 2-OMe SCH₂ 5-F,6-Me O S G9.70 Me H 2-OMe OCH₂ 5-F,7-Me O S G9.71 Me H 2-OMe SCH₂ 5-F,7-Me O S G9.72 Me H 2-OMe OCH₂ 4-Me,6-F O S G9.73 Me H 2-OMe SCH₂ 4-Me,6-F O S G9.74 Me H 2-OMe OCH₂ 5-Me,6-F O S G9.75 Me H 2-OMe SCH₂ 5-Me,6-F O S G9.76 Me H 2-OMe OCH₂ 6-F,7-Me O S G9.77 Me H 2-OMe SCH₂ 6-F,7-Me O S G9.78 Me H 2-OMe OCH₂ 4-Me,7-F O S G9.79 Me H 2-OMe SCH₂ 4-Me,7-F O S G9.80 Me H 2-OMe OCH₂ 5-Me,7-F O S G9.81 Me H 2-OMe SCH₂ 5-Me,7-F O S G9.82 Me H 2-OMe OCH₂ 6-Me,7-F O S G9.83 Me H 2-OMe SCH₂ 6-Me,7-F O S G9.84 Me H 2-OMe OCH₂ 4-Cl,5-Me O S G9.85 Me H 2-OMe SCH₂ 4-Cl,5-Me O S G9.86 Me H 2-OMe OCH₂ 4-Cl,6-Me O S G9.87 Me H 2-OMe SCH₂ 4-Cl,6-Me O S G9.88 Me H 2-OMe OCH₂ 4-Cl,7-Me O S G9.89 Me H 2-OMe SCH₂ 4-Cl,7-Me O S G9.90 Me H 2-OMe OCH₂ 4-Me,5-Cl O S G9.91 Me H 2-OMe SCH₂ 4-Me,5-Cl O S G9.92 Me H 2-OMe OCH₂ 5-Cl,6-Me O S G9.93 Me H 2-OMe SCH₂ 5-Cl,6-Me O S G9.94 Me H 2-OMe OCH₂ 5-Cl,7-Me O S G9.95 Me H 2-OMe SCH₂ 5-Cl,7-Me O S G9.96 Me H 2-OMe OCH₂ 4-Me,6-Cl O S G9.97 Me H 2-OMe SCH₂ 4-Me,6-Cl O S G9.98 Me H 2-OMe OCH₂ 5-Me,6-Cl O S G9.99 Me H 2-OMe SCH₂ 5-Me,6-Cl O S G9.100 Me H 2-OMe OCH₂ 6-Cl,7-Me O S G9.101 Me H 2-OMe SCH₂ 6-Cl,7-Me O S G9.102 Me H 2-OMe OCH₂ 4-Me,7-Cl O S G9.103 Me H 2-OMe SCH₂ 4-Me,7-Cl O S G9.104 Me H 2-OMe OCH₂ 5-Me,7-Cl O S G9.105 Me H 2-OMe SCH₂ 5-Me,7-Cl O S G9.106 Me H 2-OMe OCH₂ 6-Me,7-Cl O S G9.107 Me H 2-OMe SCH₂ 6-Me,7-Cl O S G9.108 Me H 2-OMe OCH₂ 4-Cl,5-F O S G9.109 Me H 2-OMe SCH₂ 4-Cl,5-F O S G9.110 Me H 2-OMe OCH₂ 4-Cl,6-F O S G9.111 Me H 2-OMe SCH₂ 4-Cl,6-F O S G9.112 Me H 2-OMe OCH₂ 4-Cl,7-F O S G9.113 Me H 2-OMe SCH₂ 4-Cl,7-F O S G9.114 Me H 2-OMe OCH₂ 4-F,5-Cl O S G9.115 Me H 2-OMe SCH₂ 4-F,5-Cl O S G9.116 Me H 2-OMe OCH₂ 5-Cl,6-F O S G9.117 Me H 2-OMe SCH₂ 5-Cl,6-F O S G9.118 Me H 2-OMe OCH₂ 5-Cl,7-F O S G9.119 Me H 2-OMe SCH₂ 5-Cl,7-F O S G9.120 Me H 2-OMe OCH₂ 4-F,6-Cl O S G9.121 Me H 2-OMe SCH₂ 4-F,6-Cl O S G9.122 Me H 2-OMe OCH₂ 5-F,6-Cl O S G9.123 Me H 2-OMe SCH₂ 5-F,6-Cl O S G9.124 Me H 2-OMe OCH₂ 7-F,6-Cl O S G9.125 Me H 2-OMe SCH₂ 7-F,6-Cl O S G9.126 Me H 2-OMe OCH₂ 4-F,7-Cl O S G9.127 Me H 2-OMe SCH₂ 4-F,7-Cl O S G9.128 Me H 2-OMe OCH₂ 5-F,7-Cl O S G9.129 Me H 2-OMe SCH₂ 5-F,7-Cl O S G9.130 Me H 2-OMe OCH₂ 6-F,7-Cl O S G9.131 Me H 2-OMe SCH₂ 6-F,7-Cl O S G10.1 Me H 3-OMe OCH₂ 4-Me O S G10.2 Me H 3-OMe SCH₂ 4-Me O S G10.3 Me H 3-OMe OCH₂ 5-Me O S G10.4 Me H 3-OMe SCH₂ 5-Me O S G10.5 Me H 3-OMe OCH₂ 6-Me O S G10.6 Me H 3-OMe SCH₂ 6-Me O S G10.7 Me H 3-OMe OCH₂ 7-Me O S G10.8 Me H 3-OMe SCH₂ 7-Me O S G10.9 Me H 3-OMe OCH₂ 5-Et O S G10.10 Me H 3-OMe SCH₂ 5-Et O S G10.11 Me H 3-OMe OCH₂ 6-Et O S G10.12 Me H 3-OMe SCH₂ 6-Et O S G10.13 Me H 3-OMe OCH₂ 4-OMe O S G10.14 Me H 3-OMe SCH₂ 4-OMe O S G10.15 Me H 3-OMe OCH₂ 5-OMe O S G10.16 Me H 3-OMe SCH₂ 5-OMe O S G10.17 Me H 3-OMe OCH₂ 6-OMe O S G10.18 Me H 3-OMe SCH₂ 6-OMe O S G10.19 Me H 3-OMe OCH₂ 7-OMe O S G10.20 Me H 3-OMe SCH₂ 7-OMe O S G10.21 Me H 3-OMe OCH₂ 5-OEt O S G10.22 Me H 3-OMe SCH₂ 5-OEt O S G10.23 Me H 3-OMe OCH₂ 6-OEt O S G10.24 Me H 3-OMe SCH₂ 6-OEt O S G10.25 Me H 3-OMe OCH₂ 4-F O S G10.26 Me H 3-OMe SCH₂ 4-F O S G10.27 Me H 3-OMe OCH₂ 5-F O S G10.28 Me H 3-OMe SCH₂ 5-F O S G10.29 MeO H 3-OMe OCH₂ 5-F O S G10.30 Me H 3-OMe OCH₂ 6-F O S G10.31 Me H 3-OMe SCH₂ 6-F O S G10.32 MeO H 3-OMe OCH₂ 6-F O S G10.33 Me H 3-OMe OCH₂ 7-F O S G10.34 Me H 3-OMe SCH₂ 7-F O S G10.35 Me H 3-OMe OCH₂ 5-Cl O S G10.36 Me H 3-OMe SCH₂ 5-Cl O S G10.37 Me H 3-OMe OCH₂ 6-Cl O S G10.38 Me H 3-OMe SCH₂ 6-Cl O S G10.39 Me H 3-OMe OCH₂ 4-CF₃ O S G10.40 Me H 3-OMe SCH₂ 4-CF₃ O S G10.41 Me H 3-OMe OCH₂ 5-CF₃ O S G10.42 Me H 3-OMe SCH₂ 5-CF₃ O S G10.43 Me H 3-OMe OCH₂ 6-CF₃ O S G10.44 Me H 3-OMe SCH₂ 6-CF₃ O S G10.45 Me H 3-OMe OCH₂ 7-CF₃ O S G10.46 Me H 3-OMe SCH₂ 7-CF₃ O S G10.47 Me H 3-OMe OCH₂ 5-OCF₃ O S G10.48 Me H 3-OMe SCH₂ 5-OCF₃ O S G10.49 Me H 3-OMe OCH₂ 6-OCF₃ O S G10.50 Me H 3-OMe SCH₂ 6-OCF₃ O S G10.51 Me H 2-OEt OCH₂ 5-F O S 177.5-179 G10.52 Me H 2-OEt SCH₂ 5-F O S G10.53 Me H 2-OEt OCH₂ 5-F O O G10.54 MeO H 2-OEt OCH₂ 5-F O S G10.55 MeO H 2-OEt SCH₂ 5-F O S G10.56 MeO H 2-OEt OCH₂ 5-F O O G10.57 Me H 2-CHF₂ OCH₂ 5-F O S 180-185 G10.58 MeO H 2-CHF₂ OCH₂ 5-F O S G10.59 Me H 2-CHF₂ OCH₂ 5-F O O G10.60 MeO H 2-CHF₂ OCH₂ 5-F O O G10.61 Me H 2-OCHF₂ OCH₂ 5-F O S 137-138 G10.62 MeO H 2-OCHF₂ OCH₂ 5-F O S G10.63 Me H 2-OCH₂CF₃ OCH₂ 5-F O S 167-168 G10.64 MeO H 2-OCH₂CF₃ OCH₂ 5-F O S G10.65 Me H 2-OCH₂CF₃ OCH₂ 5-F O O G10.66 MeO H 2-OCH₂CF₃ OCH₂ 5-F O O G11.1 Me H 2-CH₂OMe OCH₂ 4-Me O S G11.2 Me H 2-CH₂OMe SCH₂ 4-Me O S G11.3 Me H 2-CH₂OMe OCH₂ 5-Me O S G11.4 Me H 2-CH₂OMe SCH₂ 5-Me O S G11.5 Me H 2-CH₂OMe OCH₂ 6-Me O S G11.6 Me H 2-CH₂OMe SCH₂ 6-Me O S G11.7 Me H 2-CH₂OMe OCH₂ 7-Me O S G11.8 Me H 2-CH₂OMe SCH₂ 7-Me O S G11.9 Me H 2-CH₂OMe OCH₂ 5-Et O S G11.10 Me H 2-CH₂OMe SCH₂ 5-Et O S G11.11 Me H 2-CH₂OMe OCH₂ 6-Et O S G11.12 Me H 2-CH₂OMe SCH₂ 6-Et O S G11.13 Me H 2-CH₂OMe OCH₂ 4-OMe O S G11.14 Me H 2-CH₂OMe SCH₂ 4-OMe O S G11.15 Me H 2-CH₂OMe OCH₂ 5-OMe O S G11.16 Me H 2-CH₂OMe SCH₂ 5-OMe O S G11.17 Me H 2-CH₂OMe OCH₂ 6-OMe O S G11.18 Me H 2-CH₂OMe SCH₂ 6-OMe O S G11.19 Me H 2-CH₂OMe OCH₂ 7-OMe O S G11.20 Me H 2-CH₂OMe SCH₂ 7-OMe O S G11.21 Me H 2-CH₂OMe OCH₂ 5-OEt O S G11.22 Me H 2-CH₂OMe SCH₂ 5-OEt O S G11.23 Me H 2-CH₂OMe OCH₂ 6-OEt O S G11.24 Me H 2-CH₂OMe SCH₂ 6-OEt O S G11.25 Me H 2-CH₂OMe OCH₂ 4-F O S G11.26 Me H 2-CH₂OMe SCH₂ 4-F O S G11.27 Me H 2-CH₂OMe OCH₂ 5-F O S G11.28 Me H 2-CH₂OMe SCH₂ 5-F O S G11.29 Me H 2-CH₂OMe OCH₂ 6-F O S G11.30 Me H 2-CH₂OMe SCH₂ 6-F O S G11.31 Me H 2-CH₂OMe OCH₂ 7-F O S G11.32 Me H 2-CH₂OMe SCH₂ 7-F O S G11.33 Me H 2-CH₂OMe OCH₂ 5-Cl O S G11.34 Me H 2-CH₂OMe SCH₂ 5-Cl O S G11.35 Me H 2-CH₂OMe OCH₂ 6-Cl O S G11.36 Me H 2-CH₂OMe SCH₂ 6-Cl O S G11.37 Me H 2-CH₂OMe OCH₂ 4-CF₃ O S G11.38 Me H 2-CH₂OMe SCH₂ 4-CF₃ O S G11.39 Me H 2-CH₂OMe OCH₂ 5-CF₃ O S G11.40 Me H 2-CH₂OMe SCH₂ 5-CF₃ O S G11.41 Me H 2-CH₂OMe OCH₂ 6-CF₃ O S G11.42 Me H 2-CH₂OMe SCH₂ 6-CF₃ O S G11.43 Me H 2-CH₂OMe OCH₂ 7-CF₃ O S G11.44 Me H 2-CH₂OMe SCH₂ 7-CF₃ O S G11.45 Me H 2-CH₂OMe OCH₂ 5-OCF₃ O S G11.46 Me H 2-CH₂OMe SCH₂ 5-OCF₃ O S G11.47 Me H 2-CH₂OMe OCH₂ 6-OCF₃ O S G11.48 Me H 2-CH₂OMe SCH₂ 6-OCF₃ O S G11.49 Me H 3-CH₂OMe OCH₂ 4-Me O S G11.50 Me H 3-CH₂OMe SCH₂ 4-Me O S G11.51 Me H 3-CH₂OMe OCH₂ 5-Me O S G11.52 Me H 3-CH₂OMe SCH₂ 5-Me O S G11.53 Me H 3-CH₂OMe OCH₂ 6-Me O S G11.54 Me H 3-CH₂OMe SCH₂ 6-Me O S G11.55 Me H 3-CH₂OMe OCH₂ 7-Me O S G11.56 Me H 3-CH₂OMe SCH₂ 7-Me O S G11.57 Me H 3-CH₂OMe OCH₂ 5-Et O S G11.58 Me H 3-CH₂OMe SCH₂ 5-Et O S G11.59 Me H 3-CH₂OMe OCH₂ 6-Et O S G11.60 Me H 3-CH₂OMe SCH₂ 6-Et O S G11.61 Me H 3-CH₂OMe OCH₂ 4-OMe O S G11.62 Me H 3-CH₂OMe SCH₂ 4-OMe O S G11.63 Me H 3-CH₂OMe OCH₂ 5-OMe O S G11.64 Me H 3-CH₂OMe SCH₂ 5-OMe O S G11.65 Me H 3-CH₂OMe OCH₂ 6-OMe O S G11.66 Me H 3-CH₂OMe SCH₂ 6-OMe O S G11.67 Me H 3-CH₂OMe OCH₂ 7-OMe O S G11.68 Me H 3-CH₂OMe SCH₂ 7-OMe O S G11.69 Me H 3-CH₂OMe OCH₂ 5-OEt O S G11.70 Me H 3-CH₂OMe SCH₂ 5-OEt O S G11.71 Me H 3-CH₂OMe OCH₂ 6-OEt O S G11.72 Me H 3-CH₂OMe SCH₂ 6-OEt O S G11.73 Me H 3-CH₂OMe OCH₂ 4-F O S G11.74 Me H 3-CH₂OMe SCH₂ 4-F O S G11.75 Me H 3-CH₂OMe OCH₂ 5-F O S G11.76 Me H 3-CH₂OMe SCH₂ 5-F O S G11.77 Me H 3-CH₂OMe OCH₂ 6-F O S G11.78 Me H 3-CH₂OMe SCH₂ 6-F O S G11.79 Me H 3-CH₂OMe OCH₂ 7-F O S G11.80 Me H 3-CH₂OMe SCH₂ 7-F O S G11.81 Me H 3-CH₂OMe OCH₂ 5-Cl O S G11.82 Me H 3-CH₂OMe SCH₂ 5-Cl O S G11.83 Me H 3-CH₂OMe OCH₂ 6-Cl O S G11.84 Me H 3-CH₂OMe SCH₂ 6-Cl O S G11.85 Me H 3-CH₂OMe OCH₂ 4-CF₃ O S G11.86 Me H 3-CH₂OMe SCH₂ 4-CF₃ O S G11.87 Me H 3-CH₂OMe OCH₂ 5-CF₃ O S G11.88 Me H 3-CH₂OMe SCH₂ 5-CF₃ O S G11.89 Me H 3-CH₂OMe OCH₂ 6-CF₃ O S G11.90 Me H 3-CH₂OMe SCH₂ 6-CF₃ O S G11.91 Me H 3-CH₂OMe OCH₂ 7-CF₃ O S G11.92 Me H 3-CH₂OMe SCH₂ 7-CF₃ O S G11.93 Me H 3-CH₂OMe OCH₂ 5-OCF₃ O S G11.94 Me H 3-CH₂OMe SCH₂ 5-OCF₃ O S G11.95 Me H 3-CH₂OMe OCH₂ 6-OCF₃ O S G11.96 Me H 3-CH₂OMe SCH₂ 6-OCF₃ O S G12.1 Me H 2-CH₂OEt OCH₂ 4-Me O S G12.2 Me H 2-CH₂OEt SCH₂ 4-Me O S G12.3 Me H 2-CH₂OEt OCH₂ 5-Me O S G12.4 Me H 2-CH₂OEt SCH₂ 5-Me O S G12.5 Me H 2-CH₂OEt OCH₂ 6-Me O S G12.6 Me H 2-CH₂OEt SCH₂ 6-Me O S G12.7 Me H 2-CH₂OEt OCH₂ 7-Me O S G12.8 Me H 2-CH₂OEt SCH₂ 7-Me O S G12.9 Me H 2-CH₂OEt OCH₂ 5-Et O S G12.10 Me H 2-CH₂OEt SCH₂ 5-Et O S G12.11 Me H 2-CH₂OEt OCH₂ 6-Et O S G12.12 Me H 2-CH₂OEt SCH₂ 6-Et O S G12.13 Me H 2-CH₂OEt OCH₂ 4-OMe O S G12.14 Me H 2-CH₂OEt SCH₂ 4-OMe O S G12.15 Me H 2-CH₂OEt OCH₂ 5-OMe O S G12.16 Me H 2-CH₂OEt SCH₂ 5-OMe O S G12.17 Me H 2-CH₂OEt OCH₂ 6-OMe O S G12.18 Me H 2-CH₂OEt SCH₂ 6-OMe O S G12.19 Me H 2-CH₂OEt OCH₂ 7-OMe O S G12.20 Me H 2-CH₂OEt SCH₂ 7-OMe O S G12.21 Me H 2-CH₂OEt OCH₂ 5-OEt O S G12.22 Me H 2-CH₂OEt SCH₂ 5-OEt O S G12.23 Me H 2-CH₂OEt OCH₂ 6-OEt O S G12.24 Me H 2-CH₂OEt SCH₂ 6-OEt O S G12.25 Me H 2-CH₂OEt OCH₂ 4-F O S G12.26 Me H 2-CH₂OEt SCH₂ 4-F O S G12.27 Me H 2-CH₂OEt OCH₂ 5-F O S G12.28 Me H 2-CH₂OEt SCH₂ 5-F O S G12.29 Me H 2-CH₂OEt OCH₂ 6-F O S G12.30 Me H 2-CH₂OEt SCH₂ 6-F O S G12.31 Me H 2-CH₂OEt OCH₂ 7-F O S G12.32 Me H 2-CH₂OEt SCH₂ 7-F O S G12.33 Me H 2-CH₂OEt OCH₂ 5-Cl O S G12.34 Me H 2-CH₂OEt SCH₂ 5-Cl O S G12.35 Me H 2-CH₂OEt OCH₂ 6-Cl O S G12.36 Me H 2-CH₂OEt SCH₂ 6-Cl O S G12.37 Me H 2-CH₂OEt OCH₂ 4-CF₃ O S G12.38 Me H 2-CH₂OEt SCH₂ 4-CF₃ O S G12.39 Me H 2-CH₂OEt OCH₂ 5-CF₃ O S G12.40 Me H 2-CH₂OEt SCH₂ 5-CF₃ O S G12.41 Me H 2-CH₂OEt OCH₂ 6-CF₃ O S G12.42 Me H 2-CH₂OEt SCH₂ 6-CF₃ O S G12.43 Me H 2-CH₂OEt OCH₂ 7-CF₃ O S G12.44 Me H 2-CH₂OEt SCH₂ 7-CF₃ O S G12.45 Me H 2-CH₂OEt OCH₂ 5-OCF₃ O S G12.46 Me H 2-CH₂OEt SCH₂ 5-OCF₃ O S G12.47 Me H 2-CH₂OEt OCH₂ 6-OCF₃ O S G12.48 Me H 2-CH₂OEt SCH₂ 6-OCF₃ O S G12.49 Me H 3-CH₂OEt OCH₂ 4-Me O S G12.50 Me H 3-CH₂OEt SCH₂ 4-Me O S G15.51 Me H 3-CH₂OEt OCH₂ 5-Me O S G12.52 Me H 3-CH₂OEt SCH₂ 5-Me O S G12.53 Me H 3-CH₂OEt OCH₂ 6-Me O S G12.54 Me H 3-CH₂OEt SCH₂ 6-Me O S G12.55 Me H 3-CH₂OEt OCH₂ 7-Me O S G12.56 Me H 3-CH₂OEt SCH₂ 7-Me O S G12.57 Me H 3-CH₂OEt OCH₂ 5-Et O S G12.58 Me H 3-CH₂OEt SCH₂ 5-Et O S G12.59 Me H 3-CH₂OEt OCH₂ 6-Et O S G12.60 Me H 3-CH₂OEt SCH₂ 6-Et O S G12.61 Me H 3-CH₂OEt OCH₂ 4-OMe O S G12.62 Me H 3-CH₂OEt SCH₂ 4-OMe O S G12.63 Me H 3-CH₂OEt OCH₂ 5-OMe O S G12.64 Me H 3-CH₂OEt SCH₂ 5-OMe O S G12.65 Me H 3-CH₂OEt OCH₂ 6-OMe O S G12.66 Me H 3-CH₂OEt SCH₂ 6-OMe O S G12.67 Me H 3-CH₂OEt OCH₂ 7-OMe O S G12.68 Me H 3-CH₂OEt SCH₂ 7-OMe O S G12.69 Me H 3-CH₂OEt OCH₂ 5-OEt O S G12.70 Me H 3-CH₂OEt SCH₂ 5-OEt O S G12.71 Me H 3-CH₂OEt OCH₂ 6-OEt O S G12.72 Me H 3-CH₂OEt SCH₂ 6-OEt O S G12.73 Me H 3-CH₂OEt OCH₂ 4-F O S G12.74 Me H 3-CH₂OEt SCH₂ 4-F O S G12.75 Me H 3-CH₂OEt OCH₂ 5-F O S G12.76 Me H 3-CH₂OEt SCH₂ 5-F O S G12.77 Me H 3-CH₂OEt OCH₂ 6-F O S G12.78 Me H 3-CH₂OEt SCH₂ 6-F O S G12.79 Me H 3-CH₂OEt OCH₂ 7-F O S G12.80 Me H 3-CH₂OEt SCH₂ 7-F O S G12.81 Me H 3-CH₂OEt OCH₂ 5-Cl O S G12.82 Me H 3-CH₂OEt SCH₂ 5-Cl O S G12.83 Me H 3-CH₂OEt OCH₂ 6-Cl O S G12.84 Me H 3-CH₂OEt SCH₂ 6-Cl O S G12.85 Me H 3-CH₂OEt OCH₂ 4-CF₃ O S G12.86 Me H 3-CH₂OEt SCH₂ 4-CF₃ O S G12.87 Me H 3-CH₂OEt OCH₂ 5-CF₃ O S G12.88 Me H 3-CH₂OEt SCH₂ 5-CF₃ O S G12.89 Me H 3-CH₂OEt OCH₂ 6-CF₃ O S G12.90 Me H 3-CH₂OEt SCH₂ 6-CF₃ O S G12.91 Me H 3-CH₂OEt OCH₂ 7-CF₃ O S G12.92 Me H 3-CH₂OEt SCH₂ 7-CF₃ O S G12.93 Me H 3-CH₂OEt OCH₂ 5-OCF₃ O S G12.94 Me H 3-CH₂OEt SCH₂ 5-OCF₃ O S G12.95 Me H 3-CH₂OEt OCH₂ 6-OCF₃ O S G12.96 Me H 3-CH₂OEt SCH₂ 6-OCF₃ O S ────────────────────────────────────[Table 7] ──────────────────────────────────── Number R ¹ R ^Two (R ^Three ) n ACR ^Four (R ^Five ) (R ⁶ ) m XQ Melting point (℃) ──────────────────────────────────── G1.1 Me H 2- Me OCH _Two 4-Me OS G1.2 Me H 2-Me SCH _Two 4-Me OS G1.3 MeO H 2-Me OCH _Two 4-Me OS 153-155 G1.4 Me H 2-Me OCH _Two 4-Me OO 160-161 G1.5 MeO H 2-Me OCH _Two 4-Me OO 149-151 G1.6 Me H 2-Me OCH _Two 5-Me OS 206-208 G1.7 Me H 2-Me SCH _Two 5-Me OS G1.8 MeO H 2-Me OCH _Two 5-Me OS 131-133 G1.9 Me H 2-Me OCH _Two 5-Me OO 177-180 G1.10 MeO H 2-Me OCH _Two 5-Me OO 164-166 G1.11 Me H 2-Me OCH _Two 6-Me OS 192-193 G1.12 Me H 2-Me SCH _Two 6-Me OS G1.13 MeO H 2-Me OCH _Two 6-Me OS 153-155 G1.14 Me H 2-Me OCH _Two 6-Me OO 185-188 G1.15 MeO H 2-Me OCH _Two 6-Me OO 139-142 G1.16 Me H 2-Me OCH _Two 7-Me OS G1.17 Me H 2-Me SCH _Two 7-Me OS G1.18 MeO H 2-Me OCH _Two 7-Me OS G1.19 Me H 2-Me OCH _Two 7-Me OO 170-173 G1.20 MeO H 2-Me OCH _Two 7-Me OO 157-159 G1.21 Me H 2-Me OCH _Two 5-Et OS G1.22 Me H 2-Me SCH _Two 5-Et OS G1.23 MeO H 2-Me OCH _Two 5-Et OS G1.24 MeO H 2-Me OCH _Two 5-Et OO G1.25 Me H 2-Me OCH _Two 6-Et OS G1.26 Me H 2-Me SCH _Two 6-Et OS G1.27 MeO H 2-Me OCH _Two 6-Et OS G1.28 Me H 2-Me OCH _Two 4-OMe OS G1.29 Me H 2-Me SCH _Two 4-OMe OS G1.30 MeO H 2-Me OCH _Two 4-OMe OS 125-126 G1.31 MeO H 2-Me OCH _Two 4-OMe OO G1.32 Me H 2-Me OCH _Two 5-OMe OS 203-204 G1.33 Me H 2-Me SCH _Two 5-OMe OS G1.34 MeO H 2-Me OCH _Two 5-OMe OS 159-161 G1.35 Me H 2-Me OCH _Two 5-OMe OO 173-177 G1.36 MeO H 2-Me OCH _Two 5-OMe OO 160-162 G1.37 Me H 2-Me OCH _Two 6-OMe OS 159-162 G1.38 Me H 2-Me SCH _Two 6-OMe OS G1.39 MeO H 2-Me OCH _Two 6-OMe OS 123-125 G1.40 Me H 2-Me OCH _Two 6-OMe OO G1.41 MeO H 2-Me OCH _Two 6-OMe OO G1.42 Me H 2-Me OCH _Two 7-OMe OS G1.43 Me H 2-Me SCH _Two 7-OMe OS G1.44 MeO H 2-Me OCH _Two 7-OMe OS 150-151 G1.45 MeO H 2-Me OCH _Two 7-OMe OO G1.46 Me H 2-Me OCH _Two 5-OEt OS G1.47 Me H 2-Me SCH _Two 5-OEt OS G1.48 Me H 2-Me OCH _Two 6-OEt OS G1.49 Me H 2-Me SCH _Two 6-OEt OS G1.50 Me H 2-Me OCH _Two 4-FOS 174-176 G1.51 Me H 2-Me SCH _Two 4-FOS G1.52 MeO H 2-Me OCH _Two 4-FOS 165-167 G1.53 Me H 2-Me OCH _Two 4-FOO G1.54 MeO H 2-Me OCH _Two 4-FOO G1.55 Me H 2-Me OCH _Two 5-FOS 205-207 G1.56 Me H 2-Me SCH _Two 5-FOS G1.57 MeO H 2-Me OCH _Two 5-FOS 165-168 G1.58 Me H 2-Me OCH _Two 5-FOO 183-185 G1.59 MeO H 2-Me OCH _Two 5-FOO 182-184 G1.60 Me H 2-Me OCH _Two 6-FOS 204-205 G1.61 Me H 2-Me SCH _Two 6-FOS G1.62 MeO H 2-Me OCH _Two 6-FOS 149-151 G1.63 Me H 2-Me OCH _Two 6-FOO 178-179 G1.64 MeO H 2-Me OCH _Two 6-FOO 138-140 G1.65 Me H 2-Me OCH _Two 7-FOS G1.66 Me H 2-Me SCH _Two 7-FOS G1.67 MeO H 2-Me OCH _Two 7-FOS 121-122 G1.68 Me H 2-Me OCH _Two 7-FOO 173-175 G1.69 MeO H 2-Me OCH _Two 7-FOO 138-141 G1.70 MeO H 2-Me OCH _Two 4-Cl OS G1.71 MeO H 2-Me OCH _Two 4-Cl OO G1.72 Me H 2-Me OCH _Two 5-Cl OS 213-214 G1.73 Me H 2-Me SCH _Two 5-Cl OS G1.74 MeO H 2-Me OCH _Two 5-Cl OS 179-182 G1.75 MeO H 2-Me SCH _Two 5-Cl OS G1.76 Me H 2-Me OCH _Two 5-Cl OO 207-209 G1.77 MeO H 2-Me OCH _Two 5-Cl OO 156-158 G1.78 MeO H 2-Me SCH _Two 5-Cl OO G1.79 Me H 2-Me OCH _Two 6-Cl OS G1.80 Me H 2-Me SCH _Two 6-Cl OS G1.81 MeO H 2-Me OCH _Two 6-Cl OS 150-152 G1.82 Me H 2-Me OCH _Two 6-Cl OO G1.83 MeO H 2-Me OCH _Two 6-Cl OO G1.84 Me H 2-Me OCH _Two 7-Cl OS G1.85 MeO H 2-Me OCH _Two 7-Cl OS 135-137 G1.86 MeO H 2-Me OCH _Two 7-Cl OO G1.87 Me H 2-Me OCH _Two 4-CF _Three OS 185-186 G1.88 Me H 2-Me SCH _Two 4-CF _Three OS G1.89 MeO H 2-Me OCH _Two 4-CF _Three OS 180-181 G1.90 Me H 2-Me OCH _Two 4-CF _Three OO G1.91 MeO H 2-Me OCH _Two 4-CF _Three OO G1.92 Me H 2-Me OCH _Two 5-CF _Three OS 209-210 G1.93 Me H 2-Me SCH _Two 5-CF _Three OS G1.94 MeO H 2-Me OCH _Two 5-CF _Three OS 173-176 G1.95 Me H 2-Me OCH _Two 5-CF _Three OO 216-218 G1.96 MeO H 2-Me OCH _Two 5-CF _Three OO 141-143 G1.97 Me H 2-Me OCH _Two 6-CF _Three OS 203-205 G1.98 Me H 2-Me SCH _Two 6-CF _Three OS G1.99 MeO H 2-Me OCH _Two 6-CF _Three OS 165-168 G1.100 Me H 2-Me OCH _Two 7-CF _Three OS G1.101 Me H 2-Me SCH _Two 7-CF _Three OS G1.102 Me H 2-Me OCH _Two 5-OCF _Three OS G1.103 Me H 2-Me SCH _Two 5-OCF _Three OS G1.104 MeO H 2-Me OCH _Two 5-OCF _Three OS G1.105 MeO H 2-Me OCH _Two 5-OCF _Three OO G1.106 Me H 2-Me OCH _Two 6-OCF _Three OS G1.107 Me H 2-Me SCH _Two 6-OCF _Three OS G1.108 MeO H 2-Me OCH _Two 6-OCF _Three OS G1.109 Me H 2-Me OCH _Two 5-NO _Two OO 212-216 G1.110 MeO H 2-Me OCH _Two 5-NO _Two OO G1.111 Me H 2-Me OCH _Two 4-COOMe OS G1.112 MeO H 2-Me OCH _Two 4-COOMe OS G1.113 Me H 2-Me OCH _Two 4-COOMe OO Clay-like G1.114 MeO H 2-Me OCH _Two 4-COOMe OO Oil G1.115 Me H 2-Me OCH _Two 5-COOMe OS G1.116 MeO H 2-Me OCH _Two 5-COOMe OS G1.117 Me H 2-Me OCH _Two 5-COOMe OO 175-183 G1.118 MeO H 2-Me OCH _Two 5-COOMe OO 132-135 G1.119 Me H 2-Me OCH _Two 6-COOMe OS G1.120 MeO H 2-Me OCH _Two 6-COOMe OS G1.121 Me H 2-Me OCH _Two 6-COOMe OO 148-153 G1.122 MeO H 2-Me OCH _Two 6-COOMe OO ~ 190 G1.123 MeO H 2-Me SCH _Two 5-FOS G1.124 MeO H 2-Me SCH _Two 5-FOO G1.125 Me H 2-Me OCH _Two 7-COOMe OS G1.126 MeO H 2-Me OCH _Two 7-COOMe OS G1.127 Me H 2-Me OCH _Two 7-COOMe OO 150-160 G1.128 MeO H 2-Me OCH _Two 7-COOMe OO 139-141 G2.1 Me H 2-Me OCH _Two 4,5-Me _Two OS G2.2 Me H 2-Me SCH _Two 4,5-Me _Two OS G2.3 MeO H 2-Me OCH _Two 4,5-Me _Two OS G2.4 Me H 2-Me OCH _Two 4,6-Me _Two OS G2.5 Me H 2-Me SCH _Two 4,6-Me _Two OS G2.6 Me H 2-Me OCH _Two 4,7-Me _Two OS G2.7 Me H 2-Me SCH _Two 4,7-Me _Two OS G2.8 Me H 2-Me OCH _Two 5,6-Me _Two OS G2.9 Me H 2-Me SCH _Two 5,6-Me _Two OS G2.10 MeO H 2-Me OCH _Two 5,6-Me _Two OS G2.11 Me H 2-Me OCH _Two 5,7-Me _Two OS G2.12 Me H 2-Me SCH _Two 5,7-Me _Two OS G2.13 Me H 2-Me OCH _Two 5,7-Me _Two OO 207-210 G2.14 MeO H 2-Me OCH _Two 5,7-Me _Two OO 154-155 G2.15 Me H 2-Me OCH _Two 6,7-Me _Two OS G2.16 Me H 2-Me SCH _Two 6,7-Me _Two OS G2.17 Me H 2-Me OCH _Two 4,5- (OMe) _Two OS G2.18 MeO H 2-Me OCH _Two 4,5- (OMe) _Two OS G2.19 Me H 2-Me OCH _Two 4,5- (OMe) _Two OS G2.20 MeO H 2-Me SCH _Two 4,5- (OMe) _Two OS G2.21 Me H 2-Me OCH _Two 4,6- (OMe) _Two OS G2.22 Me H 2-Me SCH _Two 4,6- (OMe) _Two OS G2.23 Me H 2-Me OCH _Two 4,7- (OMe) _Two OS G2.24 Me H 2-Me SCH _Two 4,7- (OMe) _Two OS G2.25 Me H 2-Me OCH _Two 5,6- (OMe) _Two OS G2.26 Me H 2-Me SCH _Two 5,6- (OMe) _Two OS G2.27 MeO H 2-Me OCH _Two 5,6- (OMe) _Two OS G2.28 Me H 2-Me OCH _Two 5,6- (OMe) _Two OO G2.29 MeO H 2-Me OCH _Two 5,6- (OMe) _Two OO G2.30 Me H 2-Me OCH _Two 5,7- (OMe) _Two OS G2.31 Me H 2-Me SCH _Two 5,7- (OMe) _Two OS G2.32 Me H 2-Me OCH _Two 6,7- (OMe) _Two OS G2.33 Me H 2-Me SCH _Two 6,7- (OMe) _Two OS G2.34 Me H 2-Me OCH _Two 4,5-F _Two OS G2.35 Me H 2-Me SCH _Two 4,5-F _Two OS G2.36 MeO H 2-Me OCH _Two 4,5-F _Two OS G2.37 Me H 2-Me OCH _Two 4,6-F _Two OS G2.38 Me H 2-Me SCH _Two 4,6-F _Two OS G2.39 MeO H 2-Me OCH _Two 4,6-F _Two OS G2.40 Me H 2-Me OCH _Two 4,7-F _Two OS G2.41 Me H 2-Me SCH _Two 4,7-F _Two OS G2.42 Me H 2-Me OCH _Two 5,6-F _Two OS 219-222 G2.43 Me H 2-Me SCH _Two 5,6-F _Two OS G2.44 MeO H 2-Me OCH _Two 5,6-F _Two OS G2.45 Me H 2-Me OCH _Two 5,7-F _Two OS G2.46 Me H 2-Me SCH _Two 5,7-F _Two OS G2.47 Me H 2-Me OCH _Two 6,7-F _Two OS G2.48 Me H 2-Me SCH _Two 6,7-F _Two OS G2.49 Me H 2-Me OCH _Two 6,7-F _Two OO 164-165 G2.50 MeO H 2-Me OCH _Two 6,7-F _Two OO 124-125 G2.51 Me H 2-Me OCH _Two 4,5-Cl _Two OS G2.52 Me H 2-Me SCH _Two 4,5-Cl _Two OS G2.53 Me H 2-Me OCH _Two 4,6-Cl _Two OS G2.54 Me H 2-Me SCH _Two 4,6-Cl _Two OS G2.55 Me H 2-Me OCH _Two 4,7-Cl _Two OS G2.56 Me H 2-Me SCH _Two 4,7-Cl _Two OS G2.57 Me H 2-Me OCH _Two 5,6-Cl _Two OS G2.58 Me H 2-Me SCH _Two 5,6-Cl _Two OS G2.59 Me H 2-Me OCH _Two 5,7-Cl _Two OS G2.60 Me H 2-Me SCH _Two 5,7-Cl _Two OS G2.61 Me H 2-Me OCH _Two 5,7-Cl _Two OO 190-193 G2.62 MeO H 2-Me OCH _Two 5,7-Cl _Two OO 130-132 G2.63 Me H 2-Me OCH _Two 6,7-Cl _Two OS G2.64 Me H 2-Me SCH _Two 6,7-Cl _Two OS G2.65 Me H 2-Me OCH _Two 4,5- (CF _Three ) _Two OS G2.67 Me H 2-Me SCH _Two 4,5- (CF _Three ) _Two OS G2.68 Me H 2-Me OCH _Two 4,6- (CF _Three ) _Two OS G2.69 Me H 2-Me SCH _Two 4,6- (CF _Three ) _Two OS G2.70 Me H 2-Me OCH _Two 4,7- (CF _Three ) _Two OS G2.71 Me H 2-Me SCH _Two 4,7- (CF _Three ) _Two OS G2.72 Me H 2-Me OCH _Two 5,6- (CF _Three ) _Two OS G2.73 Me H 2-Me SCH _Two 5,6- (CF _Three ) _Two OS G2.74 Me H 2-Me OCH _Two 5,7- (CF _Three ) _Two OS G2.75 Me H 2-Me SCH _Two 5,7- (CF _Three ) _Two OS G2.76 Me H 2-Me OCH _Two 6,7- (CF _Three ) _Two OS G2.77 Me H 2-Me SCH _Two 6,7- (CF _Three ) _Two OS G2.78 Me H 2-Me OCH _Two 4-F, 5-Me OS G2.79 Me H 2-Me SCH _Two 4-F, 5-Me OS G2.80 Me H 2-Me OCH _Two 4-F, 6-Me OS G2.81 Me H 2-Me SCH _Two 4-F, 6-Me OS G2.82 Me H 2-Me OCH _Two 4-F, 7-Me OS G2.83 Me H 2-Me SCH _Two 4-F, 7-Me OS G2.84 Me H 2-Me OCH _Two 4-Me, 5-FOS G2.85 Me H 2-Me SCH _Two 4-Me, 5-FOS G2.86 Me H 2-Me OCH _Two 5-F, 6-Me OS 222-225 G2.87 Me H 2-Me SCH _Two 5-F, 6-Me OS G2.88 MeO H 2-Me OCH _Two 5-F, 6-Me OS G2.89 Me H 2-Me OCH _Two 5-F, 6-Me OO G2.90 MeO H 2-Me OCH _Two 5-F, 6-Me OO G2.91 Me H 2-Me OCH _Two 5-F, 7-Me OS G2.92 Me H 2-Me SCH _Two 5-F, 7-Me OS G2.93 Me H 2-Me OCH _Two 4-Me, 6-FOS G2.94 Me H 2-Me SCH _Two 4-Me, 6-FOS G2.95 Me H 2-Me OCH _Two 5-Me, 6-FOS G2.96 Me H 2-Me SCH _Two 5-Me, 6-FOS G2.97 Me H 2-Me OCH _Two 6-F, 7-Me OS 191-195 G2.98 Me H 2-Me SCH _Two 6-F, 7-Me OS G2.99 MeO H 2-Me OCH _Two 6-F, 7-Me OS G2.100 Me H 2-Me OCH _Two 4-Me, 7-FOS G2.101 Me H 2-Me SCH _Two 4-Me, 7-FOS G2.102 Me H 2-Me OCH _Two 5-Me, 7-FOS G2.103 Me H 2-Me SCH _Two 5-Me, 7-FOS G2.104 Me H 2-Me OCH _Two 6-Me, 7-FOS G2.105 Me H 2-Me SCH _Two 6-Me, 7-FOS G2.106 Me H 2-Me OCH _Two 4-Cl, 5-Me OS G2.107 Me H 2-Me SCH _Two 4-Cl, 5-Me OS G2.108 MeO H 2-Me OCH _Two 4-Cl, 5-Me OS G2.109 Me H 2-Me OCH _Two 4-Cl, 6-Me OS G2.110 Me H 2-Me SCH _Two 4-Cl, 6-Me OS G2.111 Me H 2-Me OCH _Two 4-Cl, 7-Me OS G2.112 Me H 2-Me SCH _Two 4-Cl, 7-Me OS G2.113 Me H 2-Me OCH _Two 4-Me, 5-Cl OS G2.114 Me H 2-Me SCH _Two 4-Me, 5-Cl OS G2.115 Me H 2-Me OCH _Two 5-Cl, 6-Me OS 249-251 G2.116 Me H 2-Me SCH _Two 5-Cl, 6-Me OS G2.117 MeO H 2-Me OCH _Two 5-Cl, 6-Me OS G2.118 Me H 2-Me OCH _Two 5-Cl, 6-Me OO G2.119 MeO H 2-Me OCH _Two 5-Cl, 6-Me OO G2.120 Me H 2-Me OCH _Two 5-Cl, 7-Me OS G2.121 Me H 2-Me SCH _Two 5-Cl, 7-Me OS G2.122 Me H 2-Me OCH _Two 4-Me, 6-Cl OS G2.123 Me H 2-Me SCH _Two 4-Me, 6-Cl OS G2.124 Me H 2-Me OCH _Two 5-Me, 6-Cl OS G2.125 Me H 2-Me SCH _Two 5-Me, 6-Cl OS G2.126 Me H 2-Me OCH _Two 6-Cl, 7-Me OS G2.127 Me H 2-Me SCH _Two 6-Cl, 7-Me OS G2.128 Me H 2-Me OCH _Two 4-Me, 7-Cl OS G2.129 Me H 2-Me SCH _Two 4-Me, 7-Cl OS G2.130 Me H 2-Me OCH _Two 5-Me, 7-Cl OS G2.131 Me H 2-Me SCH _Two 5-Me, 7-Cl OS G2.132 Me H 2-Me OCH _Two 6-Me, 7-Cl OS G2.133 Me H 2-Me SCH _Two 6-Me, 7-Cl OS G2.134 Me H 2-Me OCH _Two 4-Cl, 6-OMe OS G2.135 Me H 2-Me SCH _Two 4-Cl, 6-OMe OS G2.136 MeO H 2-Me OCH _Two 4-Cl, 6-OMe OS G2.137 Me H 2-Me OCH _Two 5-Cl, 6-OMe OS 228-230 G2.138 Me H 2-Me SCH _Two 5-Cl, 6-OMe OS G2.139 MeO H 2-Me OCH _Two 5-Cl, 6-OMe OS G2.140 Me H 2-Me OCH _Two 4-Cl, 5-FOS G2.141 Me H 2-Me SCH _Two 4-Cl, 5-FOS G2.142 Me H 2-Me OCH _Two 4-Cl, 6-FOS G2.143 Me H 2-Me SCH _Two 4-Cl, 6-FOS G2.144 Me H 2-Me OCH _Two 4-Cl, 7-FOS G2.145 Me H 2-Me SCH _Two 4-Cl, 7-FOS G2.146 Me H 2-Me OCH _Two 4-F, 5-Cl OS G2.147 Me H 2-Me SCH _Two 4-F, 5-Cl OS G2.148 Me H 2-Me OCH _Two 5-Cl, 6-FOS 242-245 G2.149 Me H 2-Me SCH _Two 5-Cl, 6-FOS G2.150 MeO H 2-Me OCH _Two 5-Cl, 6-FOS G2.151 Me H 2-Me OCH _Two 5-Cl, 6-FOO G2.152 MeO H 2-Me OCH _Two 5-Cl, 6-FOO G2.153 Me H 2-Me OCH _Two 5-Cl, 7-FOS G2.154 Me H 2-Me SCH _Two 5-Cl, 7-FOS G2.156 Me H 2-Me OCH _Two 4-F, 6-Cl OS G2.157 Me H 2-Me SCH _Two 4-F, 6-Cl OS G2.158 Me H 2-Me OCH _Two 5-F, 6-Cl OS G2.159 Me H 2-Me SCH _Two 5-F, 6-Cl OS G2.160 Me H 2-Me OCH _Two 6-Cl, 7-FOS G2.161 Me H 2-Me SCH _Two 6-Cl, 7-FOS G2.162 Me H 2-Me OCH _Two 4-F, 7-Cl OS G2.163 Me H 2-Me SCH _Two 4-F, 7-Cl OS G2.164 Me H 2-Me OCH _Two 5-F, 7-Cl OS G2.165 Me H 2-Me SCH _Two 5-F, 7-Cl OS G2.166 Me H 2-Me OCH _Two 6-F, 7-Cl OS 218-220 G2.167 Me H 2-Me SCH _Two 6-F, 7-Cl OS G2.168 MeO H 2-Me OCH _Two 6-F, 7-Cl OS G3.1 Me H 3-Me OCH _Two 4-Me OS G3.2 Me H 3-Me SCH _Two 4-Me OS G3.3 Me H 3-Me OCH _Two 5-Me OS G3.4 Me H 3-Me SCH _Two 5-Me OS G3.5 Me H 3-Me OCH _Two 6-Me OS G3.6 Me H 3-Me SCH _Two 6-Me OS G3.7 Me H 3-Me OCH _Two 7-Me OS G3.8 Me H 3-Me SCH _Two 7-Me OS G3.9 Me H 3-Me OCH _Two 5-Et OS G3.10 Me H 3-Me SCH _Two 5-Et OS G3.11 Me H 3-Me OCH _Two 6-Et OS G3.12 Me H 3-Me SCH _Two 6-Et OS G3.13 Me H 3-Me OCH _Two 4-OMe OS G3.14 Me H 3-Me SCH _Two 4-OMe OS G3.15 Me H 3-Me OCH _Two 5-OMe OS G3.16 Me H 3-Me SCH _Two 5-OMe OS G3.17 Me H 3-Me OCH _Two 6-OMe OS G3.18 Me H 3-Me SCH _Two 6-OMe OS G3.19 Me H 3-Me OCH _Two 7-OMe OS G3.20 Me H 3-Me SCH _Two 7-OMe OS G3.21 Me H 3-Me OCH _Two 5-OEt OS G3.22 Me H 3-Me SCH _Two 5-OEt OS G3.23 Me H 3-Me OCH _Two 6-OEt OS G3.24 Me H 3-Me SCH _Two 6-OEt OS G3.25 Me H 3-Me OCH _Two 4-FOS G3.26 Me H 3-Me SCH _Two 4-FOS G3.27 Me H 3-Me OCH _Two 5-FOS G3.28 Me H 3-Me SCH _Two 5-FOS G3.29 Me H 3-Me OCH _Two 6-FOS G3.30 Me H 3-Me SCH _Two 6-FOS G3.31 Me H 3-Me OCH _Two 7-FOS G3.32 Me H 3-Me SCH _Two 7-FOS G3.33 Me H 3-Me OCH _Two 5-Cl OS G3.34 Me H 3-Me SCH _Two 5-Cl OS G3.35 Me H 3-Me OCH _Two 6-Cl OS G3.36 Me H 3-Me SCH _Two 6-Cl OS G3.37 Me H 3-Me OCH _Two 4-CF _Three OS G3.38 Me H 3-Me SCH _Two 4-CF _Three OS G3.39 Me H 3-Me OCH _Two 5-CF _Three OS G3.40 Me H 3-Me SCH _Two 5-CF _Three OS G3.41 Me H 3-Me OCH _Two 6-CF _Three OS G3.42 Me H 3-Me SCH _Two 6-CF _Three OS G3.45 Me H 3-Me SCH _Two 7-CF _Three OS G3.46 Me H 3-Me OCH _Two 5-OCF _Three OS G3.47 Me H 3-Me SCH _Two 5-OCF _Three OS G3.48 Me H 3-Me OCH _Two 6-OCF _Three OS G3.49 Me H 3-Me SCH _Two 6-OCF _Three OS G3.50 Me H 3-Me OCH _Two 4,5-Me _Two OS G3.51 Me H 3-Me SCH _Two 4,5-Me _Two OS G3.52 Me H 3-Me OCH _Two 4,6-Me _Two OS G3.53 Me H 3-Me SCH _Two 4,6-Me _Two OS G3.54 Me H 3-Me OCH _Two 4,7-Me _Two OS G3.55 Me H 3-Me SCH _Two 4,7-Me _Two OS G3.56 Me H 3-Me OCH _Two 5,6-Me _Two OS G3.57 Me H 3-Me SCH _Two 5,6-Me _Two OS G3.58 Me H 3-Me OCH _Two 5,7-Me _Two OS G3.59 Me H 3-Me SCH _Two 5,7-Me _Two OS G3.60 Me H 3-Me OCH _Two 6,7-Me _Two OS G3.61 Me H 3-Me SCH _Two 6,7-Me _Two OS G3.62 Me H 3-Me OCH _Two 4,5- (OMe) _Two OS G3.63 Me H 3-Me SCH _Two 4,5- (OMe) _Two OS G3.64 Me H 3-Me OCH _Two 4,6- (OMe) _Two OS G3.65 Me H 3-Me SCH _Two 4,6- (OMe) _Two OS G3.66 Me H 3-Me OCH _Two 4,7- (OMe) _Two OS G3.67 Me H 3-Me SCH _Two 4,7- (OMe) _Two OS G3.68 Me H 3-Me OCH _Two 5,6- (OMe) _Two OS G3.69 Me H 3-Me SCH _Two 5,6- (OMe) _Two OS G3.70 Me H 3-Me OCH _Two 5,7- (OMe) _Two OS G3.71 Me H 3-Me SCH _Two 5,7- (OMe) _Two OS G3.72 Me H 3-Me OCH _Two 6,7- (OMe) _Two OS G3.73 Me H 3-Me SCH _Two 6,7- (OMe) _Two OS G3.74 Me H 3-Me OCH _Two 4,5-F _Two OS G3.75 Me H 3-Me SCH _Two 4,5-F _Two OS G3.76 Me H 3-Me OCH _Two 4,6-F _Two OS G3.77 Me H 3-Me SCH _Two 4,6-F _Two OS G3.78 Me H 3-Me OCH _Two 4,7-F _Two OS G3.79 Me H 3-Me SCH _Two 4,7-F _Two OS G3.80 Me H 3-Me OCH _Two 5,6-F _Two OS G3.81 Me H 3-Me SCH _Two 5,6-F _Two OS G3.82 Me H 3-Me OCH _Two 5,7-F _Two OS G3.83 Me H 3-Me SCH _Two 5,7-F _Two OS G3.84 Me H 3-Me OCH _Two 6,7-F _Two OS G3.85 Me H 3-Me SCH _Two 6,7-F _Two OS G3.86 Me H 3-Me OCH _Two 4,5-Cl _Two OS G3.87 Me H 3-Me SCH _Two 4,5-Cl _Two OS G3.88 Me H 3-Me OCH _Two 4,6-Cl _Two OS G3.89 Me H 3-Me SCH _Two 4,6-Cl _Two OS G3.90 Me H 3-Me OCH _Two 4,7-Cl _Two OS G3.91 Me H 3-Me SCH _Two 4,7-Cl _Two OS G3.92 Me H 3-Me OCH _Two 5,6-Cl _Two OS G3.93 Me H 3-Me SCH _Two 5,6-Cl _Two OS G3.94 Me H 3-Me OCH _Two 5,7-Cl _Two OS G3.95 Me H 3-Me SCH _Two 5,7-Cl _Two OS G3.96 Me H 3-Me OCH _Two 6,7-Cl _Two OS G3.97 Me H 3-Me SCH _Two 6,7-Cl _Two OS G3.98 Me H 3-Me OCH _Two 4,5- (CF _Three ) _Two OS G3.99 Me H 3-Me SCH _Two 4,5- (CF _Three ) _Two OS G3.100 Me H 3-Me OCH _Two 4,6- (CF _Three ) _Two OS G3.101 Me H 3-Me SCH _Two 4,6- (CF _Three ) _Two OS G3.102 Me H 3-Me OCH _Two 4,7- (CF _Three ) _Two OS G3.103 Me H 3-Me SCH _Two 4,7- (CF _Three ) _Two OS G3.104 Me H 3-Me OCH _Two 5,6- (CF _Three ) _Two OS G3.105 Me H 3-Me SCH _Two 5,6- (CF _Three ) _Two OS G3.106 Me H 3-Me OCH _Two 5,7- (CF _Three ) _Two OS G3.107 Me H 3-Me SCH _Two 5,7- (CF _Three ) _Two OS G3.108 Me H 3-Me OCH _Two 6,7- (CF _Three ) _Two OS G3.109 Me H 3-Me SCH _Two 6,7- (CF _Three ) _Two OS G4.1 Me H 3-Me OCH _Two 4-F, 5-Me OS G4.2 Me H 3-Me SCH _Two 4-F, 5-Me OS G4.3 Me H 3-Me OCH _Two 4-F, 6-Me OS G4.4 Me H 3-Me SCH _Two 4-F, 6-Me OS G4.5 Me H 3-Me OCH _Two 4-F, 7-Me OS G4.6 Me H 3-Me SCH _Two 4-F, 7-Me OS G4.7 Me H 3-Me OCH _Two 4-Me, 5-FOS G4.8 Me H 3-Me SCH _Two 4-Me, 5-FOS G4.9 Me H 3-Me OCH _Two 5-F, 6-Me OS G4.10 Me H 3-Me SCH _Two 5-F, 6-Me OS G4.11 Me H 3-Me OCH _Two 5-F, 7-Me OS G4.12 Me H 3-Me SCH _Two 5-F, 7-Me OS G4.13 Me H 3-Me OCH _Two 4-Me, 6-FOS G4.14 Me H 3-Me SCH _Two 4-Me, 6-FOS G4.15 Me H 3-Me OCH _Two 5-Me, 6-FOS G4.16 Me H 3-Me SCH _Two 5-Me, 6-FOS G4.17 Me H 3-Me OCH _Two 6-F, 7-Me OS G4.18 Me H 3-Me SCH _Two 6-F, 7-Me OS G4.19 Me H 3-Me OCH _Two 4-Me, 7-FOS G4.20 Me H 3-Me SCH _Two 4-Me, 7-FOS G4.21 Me H 3-Me OCH _Two 5-Me, 7-FOS G4.22 Me H 3-Me SCH _Two 5-Me, 7-FOS G4.23 Me H 3-Me OCH _Two 6-Me, 7-FOS G4.24 Me H 3-Me SCH _Two 6-Me, 7-FOS G4.25 Me H 3-Me OCH _Two 4-Cl, 5-Me OS G4.26 Me H 3-Me SCH _Two 4-Cl, 5-Me OS G4.27 Me H 3-Me OCH _Two 4-Cl, 6-Me OS G4.28 Me H 3-Me SCH _Two 4-Cl, 6-Me OS G4.29 Me H 3-Me OCH _Two 4-Cl, 7-Me OS G4.30 Me H 3-Me SCH _Two 4-Cl, 7-Me OS G4.31 Me H 3-Me OCH _Two 4-Me, 5-Cl OS G4.32 Me H 3-Me SCH _Two 4-Me, 5-Cl OS G4.33 Me H 3-Me OCH _Two 5-Cl, 6-Me OS G4.34 Me H 3-Me SCH _Two 5-Cl, 6-Me OS G4.35 Me H 3-Me OCH _Two 5-Cl, 7-Me OS G4.36 Me H 3-Me SCH _Two 5-Cl, 7-Me OS G4.37 Me H 3-Me OCH _Two 4-Me, 6-Cl OS G4.38 Me H 3-Me SCH _Two 4-Me, 6-Cl OS G4.39 Me H 3-Me OCH _Two 5-Me, 6-Cl OS G4.40 Me H 3-Me SCH _Two 5-Me, 6-Cl OS G4.41 Me H 3-Me OCH _Two 6-Cl, 7-Me OS G4.42 Me H 3-Me SCH _Two 6-Cl, 7-Me OS G4.43 Me H 3-Me OCH _Two 4-Me, 7-Cl OS G4.44 Me H 3-Me SCH _Two 4-Me, 7-Cl OS G4.45 Me H 3-Me OCH _Two 5-Me, 7-Cl OS G4.46 Me H 3-Me SCH _Two 5-Me, 7-Cl OS G4.47 Me H 3-Me OCH _Two 6-Me, 7-Cl OS G4.48 Me H 3-Me SCH _Two 6-Me, 7-Cl OS G4.49 Me H 3-Me OCH _Two 4-Cl, 5-FOS G4.50 Me H 3-Me SCH _Two 4-Cl, 5-FOS G4.51 Me H 3-Me OCH _Two 4-Cl, 6-FOS G4.52 Me H 3-Me SCH _Two 4-Cl, 6-FOS G4.53 Me H 3-Me OCH _Two 4-Cl, 7-FOS G4.54 Me H 3-Me SCH _Two 4-Cl, 7-FOS G4.55 Me H 3-Me OCH _Two 4-F, 5-Cl OS G4.56 Me H 3-Me SCH _Two 4-F, 5-Cl OS G4.57 Me H 3-Me OCH _Two 5-Cl, 6-FOS G4.58 Me H 3-Me SCH _Two 5-Cl, 6-FOS G4.59 Me H 3-Me OCH _Two 5-Cl, 7-FOS G4.60 Me H 3-Me SCH _Two 5-Cl, 7-FOS G4.61 Me H 3-Me OCH _Two 4-F, 6-Cl OS G4.62 Me H 3-Me SCH _Two 4-F, 6-Cl OS G4.63 Me H 3-Me OCH _Two 5-F, 6-Cl OS G4.64 Me H 3-Me SCH _Two 5-F, 6-Cl OS G4.65 Me H 3-Me OCH _Two 6-Cl, 7-FOS G4.66 Me H 3-Me SCH _Two 6-Cl, 7-FOS G4.67 Me H 3-Me OCH _Two 4-F, 7-Cl OS G4.68 Me H 3-Me SCH _Two 4-F, 7-Cl OS G4.69 Me H 3-Me OCH _Two 5-F, 7-Cl OS G4.70 Me H 3-Me SCH _Two 5-F, 7-Cl OS G4.71 Me H 3-Me OCH _Two 6-F, 7-Cl OS G4.72 Me H 3-Me SCH _Two 6-F, 7-Cl OS G5.1 Me H 2-Et OCH _Two 4-Me OS G5.2 Me H 2-Et SCH _Two 4-Me OS G5.3 Me H 2-Et OCH _Two 5-Me OS 218-221 G5.4 Me H 2-Et SCH _Two 5-Me OS G5.5 MeO H 2-Et OCH _Two 5-Me OS G5.6 Me H 2-Et OCH _Two 6-Me OS 198-200 G5.7 Me H 2-Et SCH _Two 6-Me OS G5.8 MeO H 2-Et OCH _Two 6-Me OS G5.9 Me H 2-Et OCH _Two 7-Me OS G5.10 Me H 2-Et SCH _Two 7-Me OS G5.11 Me H 2-Et OCH _Two 5-Et OS G5.12 Me H 2-Et SCH _Two 5-Et OS G5.13 Me H 2-Et OCH _Two 6-Et OS G5.14 Me H 2-Et SCH _Two 6-Et OS G5.15 Me H 2-Et OCH _Two 4-OMe OS G5.16 Me H 2-Et SCH _Two 4-OMe OS G5.17 Me H 2-Et OCH _Two 5-OMe OS 169-172 G5.18 Me H 2-Et SCH _Two 5-OMe OS G5.19 MeO H 2-Et OCH _Two 5-OMe OS G5.20 Me H 2-Et OCH _Two 6-OMe OS 157-160 G5.21 Me H 2-Et SCH _Two 6-OMe OS G5.22 MeO H 2-Et OCH _Two 6-OMe OS G5.23 Me H 2-Et OCH _Two 6-OMe OO G5.24 MeO H 2-Et OCH _Two 6-OMe OO G5.25 Me H 2-Et OCH _Two 7-OMe OS G5.26 Me H 2-Et SCH _Two 7-OMe OS G5.27 Me H 2-Et OCH _Two 5-OEt OS G5.28 Me H 2-Et SCH _Two 5-OEt OS G5.29 Me H 2-Et OCH _Two 6-OEt OS G5.30 Me H 2-Et SCH _Two 6-OEt OS G5.31 Me H 2-Et OCH _Two 4-FOS G5.32 Me H 2-Et SCH _Two 4-FOS G5.33 Me H 2-Et OCH _Two 5-FOS 197-198 G5.34 Me H 2-Et SCH _Two 5-FOS G5.35 MeO H 2-Et OCH _Two 5-FOS G5.36 Me H 2-Et OCH _Two 5-FOO G5.37 MeO H 2-Et OCH _Two 5-FOO G5.38 Me H 2-Et OCH _Two 6-FOS 198-200 G5.39 Me H 2-Et SCH _Two 6-FOS G5.40 MeO H 2-Et OCH _Two 6-FOS G5.41 Me H 2-Et OCH _Two 6-FOO G5.42 MeO H 2-Et OCH _Two 6-FOO G5.43 Me H 2-Et OCH _Two 7-FOS G5.44 Me H 2-Et SCH _Two 7-FOS G5.45 Me H 2-Et OCH _Two 5-Cl OS 210-213 G5.46 Me H 2-Et SCH _Two 5-Cl OS G5.47 MeO H 2-Et OCH _Two 5-Cl OS G5.48 Me H 2-Et OCH _Two 6-Cl OS G5.49 Me H 2-Et SCH _Two 6-Cl OS G5.50 Me H 2-Et OCH _Two 4-CF _Three OS G5.51 Me H 2-Et SCH _Two 4-CF _Three OS G5.52 Me H 2-Et OCH _Two 5-CF _Three OS 210-212 G5.53 Me H 2-Et SCH _Two 5-CF _Three OS G5.54 MeO H 2-Et OCH _Two 5-CF _Three OS G5.55 Me H 2-Et OCH _Two 6-CF _Three OS G5.56 Me H 2-Et SCH _Two 6-CF _Three OS G5.57 Me H 2-Et OCH _Two 7-CF _Three OS G5.58 Me H 2-Et SCH _Two 7-CF _Three OS G5.59 Me H 2-Et OCH _Two 5-OCF _Three OS G5.60 Me H 2-Et SCH _Two 5-OCF _Three OS G5.61 Me H 2-Et OCH _Two 6-OCF _Three OS G5.62 Me H 2-Et SCH _Two 6-OCF _Three OS G6.1 Me H 2-Et OCH _Two 4,5-Me _Two OS G6.2 Me H 2-Et SCH _Two 4,5-Me _Two OS G6.3 Me H 2-Et OCH _Two 4,6-Me _Two OS G6.4 Me H 2-Et SCH _Two 4,6-Me _Two OS G6.5 Me H 2-Et OCH _Two 4,7-Me _Two OS G6.6 Me H 2-Et SCH _Two 4,7-Me _Two OS G6.7 Me H 2-Et OCH _Two 5,6-Me _Two OS G6.8 Me H 2-Et SCH _Two 5,6-Me _Two OS G6.9 Me H 2-Et OCH _Two 5,7-Me _Two OS G6.10 Me H 2-Et SCH _Two 5,7-Me _Two OS G6.11 Me H 2-Et OCH _Two 6,7-Me _Two OS G6.12 Me H 2-Et SCH _Two 6,7-Me _Two OS G6.13 Me H 2-Et OCH _Two 4,5- (OMe) _Two OS G6.14 Me H 2-Et SCH _Two 4,5- (OMe) _Two OS G6.15 Me H 2-Et OCH _Two 4,6- (OMe) _Two OS G6.16 Me H 2-Et SCH _Two 4,6- (OMe) _Two OS G6.17 Me H 2-Et OCH _Two 4,7- (OMe) _Two OS G6.18 Me H 2-Et SCH _Two 4,7- (OMe) _Two OS G6.19 Me H 2-Et OCH _Two 5,6- (OMe) _Two OS G6.20 Me H 2-Et SCH _Two 5,6- (OMe) _Two OS G6.21 Me H 2-Et OCH _Two 5,7- (OMe) _Two OS G6.22 Me H 2-Et SCH _Two 5,7- (OMe) _Two OS G6.23 Me H 2-Et OCH _Two 6,7- (OMe) _Two OS G6.24 Me H 2-Et SCH _Two 6,7- (OMe) _Two OS G6.25 Me H 2-Et OCH _Two 4,5-F _Two OS G6.26 Me H 2-Et SCH _Two 4,5-F _Two OS G6.27 Me H 2-Et OCH _Two 4,6-F _Two OS G6.28 Me H 2-Et SCH _Two 4,6-F _Two OS G6.29 Me H 2-Et OCH _Two 4,7-F _Two OS G6.30 Me H 2-Et SCH _Two 4,7-F _Two OS G6.31 Me H 2-Et OCH _Two 5,6-F _Two OS 213-214 G6.32 Me H 2-Et SCH _Two 5,6-F _Two OS G6.33 MeO H 2-Et OCH _Two 5,6-F _Two OS G6.34 Me H 2-Et OCH _Two 5,7-F _Two OS G6.35 Me H 2-Et SCH _Two 5,7-F _Two OS G6.36 Me H 2-Et OCH _Two 6,7-F _Two OS G6.37 Me H 2-Et SCH _Two 6,7-F _Two OS G6.38 Me H 2-Et OCH _Two 4,5-Cl _Two OS G6.39 Me H 2-Et SCH _Two 4,5-Cl _Two OS G6.40 Me H 2-Et OCH _Two 4,6-Cl _Two OS G6.41 Me H 2-Et SCH _Two 4,6-Cl _Two OS G6.42 Me H 2-Et OCH _Two 4,7-Cl _Two OS G6.43 Me H 2-Et SCH _Two 4,7-Cl _Two OS G6.44 Me H 2-Et OCH _Two 5,6-Cl _Two OS G6.45 Me H 2-Et SCH _Two 5,6-Cl _Two OS G6.46 Me H 2-Et OCH _Two 5,7-Cl _Two OS G6.47 Me H 2-Et SCH _Two 5,7-Cl _Two OS G6.48 Me H 2-Et OCH _Two 6,7-Cl _Two OS G6.49 Me H 2-Et SCH _Two 6,7-Cl _Two OS G6.50 Me H 2-Et OCH _Two 4,5- (CF _Three ) _Two OS G6.51 Me H 2-Et SCH _Two 4,5- (CF _Three ) _Two OS G6.52 Me H 2-Et OCH _Two 4,6- (CF _Three ) _Two OS G6.53 Me H 2-Et SCH _Two 4,6- (CF _Three ) _Two OS G6.54 Me H 2-Et OCH _Two 4,7- (CF _Three ) _Two OS G6.55 Me H 2-Et SCH _Two 4,7- (CF _Three ) _Two OS G6.56 Me H 2-Et OCH _Two 5,6- (CF _Three ) _Two OS G6.57 Me H 2-Et SCH _Two 5,6- (CF _Three ) _Two OS G6.58 Me H 2-Et OCH _Two 5,7- (CF _Three ) _Two OS G6.59 Me H 2-Et SCH _Two 5,7- (CF _Three ) _Two OS G6.60 Me H 2-Et OCH _Two 6,7- (CF _Three ) _Two OS G6.61 Me H 2-Et SCH _Two 6,7- (CF _Three ) _Two OS G6.62 Me H 2-Et OCH _Two 4-F, 5-Me OS G6.63 Me H 2-Et SCH _Two 4-F, 5-Me OS G6.64 Me H 2-Et OCH _Two 4-F, 6-Me OS G6.65 Me H 2-Et SCH _Two 4-F, 6-Me OS G6.66 Me H 2-Et OCH _Two 4-F, 7-Me OS G6.67 Me H 2-Et SCH _Two 4-F, 7-Me OS G6.68 Me H 2-Et OCH _Two 4-Me, 5-FOS G6.69 Me H 2-Et SCH _Two 4-Me, 5-FOS G6.70 Me H 2-Et OCH _Two 5-F, 6-Me OS G6.71 Me H 2-Et SCH _Two 5-F, 6-Me OS G6.72 Me H 2-Et OCH _Two 5-F, 7-Me OS G6.73 Me H 2-Et SCH _Two 5-F, 7-Me OS G6.74 Me H 2-Et OCH _Two 4-Me, 6-FOS G6.75 Me H 2-Et SCH _Two 4-Me, 6-FOS G6.76 Me H 2-Et OCH _Two 5-Me, 6-FOS G6.77 Me H 2-Et SCH _Two 5-Me, 6-FOS G6.78 Me H 2-Et OCH _Two 6-F, 7-Me OS G6.79 Me H 2-Et SCH _Two 6-F, 7-Me OS G6.80 Me H 2-Et OCH _Two 4-Me, 7-FOS G6.81 Me H 2-Et SCH _Two 4-Me, 7-FOS G6.82 Me H 2-Et OCH _Two 5-Me, 7-FOS G6.83 Me H 2-Et SCH _Two 5-Me, 7-FOS G6.84 Me H 2-Et OCH _Two 6-Me, 7-FOS G6.85 Me H 2-Et SCH _Two 6-Me, 7-FOS G6.86 Me H 2-Et OCH _Two 4-Cl, 5-Me OS G6.87 Me H 2-Et SCH _Two 4-Cl, 5-Me OS G6.88 Me H 2-Et OCH _Two 4-Cl, 6-Me OS G6.89 Me H 2-Et SCH _Two 4-Cl, 6-Me OS G6.90 Me H 2-Et OCH _Two 4-Cl, 7-Me OS G6.92 Me H 2-Et OCH _Two 4-Me, 5-Cl OS G6.93 Me H 2-Et SCH _Two 4-Me, 5-Cl OS G6.94 Me H 2-Et OCH _Two 5-Cl, 6-Me OS G6.95 Me H 2-Et SCH _Two 5-Cl, 6-Me OS G6.96 Me H 2-Et OCH _Two 5-Cl, 7-Me OS G6.97 Me H 2-Et SCH _Two 5-Cl, 7-Me OS G6.98 Me H 2-Et OCH _Two 4-Me, 6-Cl OS G6.99 Me H 2-Et SCH _Two 4-Me, 6-Cl OS G6.100 Me H 2-Et OCH _Two 5-Me, 6-Cl OS G6.101 Me H 2-Et SCH _Two 5-Me, 6-Cl OS G6.102 Me H 2-Et OCH _Two 6-Cl, 7-Me OS G6.103 Me H 2-Et SCH _Two 6-Cl, 7-Me OS G6.104 Me H 2-Et OCH _Two 4-Me, 7-Cl OS G6.105 Me H 2-Et SCH _Two 4-Me, 7-Cl OS G6.106 Me H 2-Et OCH _Two 5-Me, 7-Cl OS G6.107 Me H 2-Et SCH _Two 5-Me, 7-Cl OS G6.108 Me H 2-Et OCH _Two 6-Me, 7-Cl OS G6.109 Me H 2-Et SCH _Two 6-Me, 7-Cl OS G6.110 Me H 2-Et OCH _Two 4-Cl, 5-FOS G6.111 Me H 2-Et SCH _Two 4-Cl, 5-FOS G6.112 Me H 2-Et OCH _Two 4-Cl, 6-FOS G6.113 Me H 2-Et SCH _Two 4-Cl, 6-FOS G6.114 Me H 2-Et OCH _Two 4-Cl, 7-FOS G6.115 Me H 2-Et SCH _Two 4-Cl, 7-FOS G6.116 Me H 2-Et OCH _Two 4-F, 5-Cl OS G6.117 Me H 2-Et SCH _Two 4-F, 5-Cl OS G6.118 Me H 2-Et OCH _Two 5-Cl, 6-FOS G6.119 Me H 2-Et SCH _Two 5-Cl, 6-FOS G6.120 Me H 2-Et OCH _Two 5-Cl, 7-FOS G6.121 Me H 2-Et SCH _Two 5-Cl, 7-FOS G6.122 Me H 2-Et OCH _Two 4-F, 6-Cl OS G6.123 Me H 2-Et SCH _Two 4-F, 6-Cl OS G6.124 Me H 2-Et OCH _Two 5-F, 6-Cl OS G6.125 Me H 2-Et SCH _Two 5-F, 6-Cl OS G6.126 Me H 2-Et OCH _Two 6-Cl, 7-FOS G6.127 Me H 2-Et SCH _Two 6-Cl, 7-FOS G6.128 Me H 2-Et OCH _Two 4-F, 7-Cl OS G6.129 Me H 2-Et SCH _Two 4-F, 7-Cl OS G6.130 Me H 2-Et OCH _Two 5-F, 7-Cl OS G6.131 Me H 2-Et SCH _Two 5-F, 7-Cl OS G6.132 Me H 2-Et OCH _Two 6-F, 7-Cl OS G6.133 Me H 2-Et SCH _Two 6-F, 7-Cl OS G7.1 Me H 3-Et OCH _Two 4-Me OS G7.2 Me H 3-Et SCH _Two 4-Me OS G7.3 Me H 3-Et OCH _Two 5-Me OS G7.4 Me H 3-Et SCH _Two 5-Me OS G7.5 Me H 3-Et OCH _Two 6-Me OS G7.6 Me H 3-Et SCH _Two 6-Me OS G7.7 Me H 3-Et OCH _Two 7-Me OS G7.8 Me H 3-Et SCH _Two 7-Me OS G7.9 Me H 3-Et OCH _Two 5-Et OS G7.10 Me H 3-Et SCH _Two 5-Et OS G7.11 Me H 3-Et OCH _Two 6-Et OS G7.12 Me H 3-Et SCH _Two 6-Et OS G7.13 Me H 3-Et OCH _Two 4-OMe OS G7.14 Me H 3-Et SCH _Two 4-OMe OS G7.15 Me H 3-Et OCH _Two 5-OMe OS G7.16 Me H 3-Et SCH _Two 5-OMe OS G7.17 Me H 3-Et OCH _Two 6-OMe OS G7.18 Me H 3-Et SCH _Two 6-OMe OS G7.19 Me H 3-Et OCH _Two 7-OMe OS G7.20 Me H 3-Et SCH _Two 7-OMe OS G7.21 Me H 3-Et OCH _Two 5-OEt OS G7.22 Me H 3-Et SCH _Two 5-OEt OS G7.23 Me H 3-Et OCH _Two 6-OEt OS G7.24 Me H 3-Et SCH _Two 6-OEt OS G7.25 Me H 3-Et OCH _Two 4-FOS G7.26 Me H 3-Et SCH _Two 4-FOS G7.27 Me H 3-Et OCH _Two 5-FOS G7.28 Me H 3-Et SCH _Two 5-FOS G7.29 Me H 3-Et OCH _Two 6-FOS G7.30 Me H 3-Et SCH _Two 6-FOS G7.31 Me H 3-Et OCH _Two 7-FOS G7.32 Me H 3-Et SCH _Two 7-FOS G7.33 Me H 3-Et OCH _Two 5-Cl OS G7.34 Me H 3-Et SCH _Two 5-Cl OS G7.35 Me H 3-Et OCH _Two 6-Cl OS G7.36 Me H 3-Et SCH _Two 6-Cl OS G7.37 Me H 3-Et OCH _Two 4-CF _Three OS G7.38 Me H 3-Et SCH _Two 4-CF _Three OS G7.39 Me H 3-Et OCH _Two 5-CF _Three OS G7.40 Me H 3-Et SCH _Two 5-CF _Three OS G7.41 Me H 3-Et OCH _Two 6-CF _Three OS G7.42 Me H 3-Et SCH _Two 6-CF _Three OS G7.43 Me H 3-Et OCH _Two 7-CF _Three OS G7.44 Me H 3-Et SCH _Two 7-CF _Three OS G7.45 Me H 3-Et OCH _Two 5-OCF _Three OS G7.46 Me H 3-Et SCH _Two 5-OCF _Three OS G7.47 Me H 3-Et OCH _Two 6-OCF _Three OS G7.48 Me H 3-Et SCH _Two 6-OCF _Three OS G7.49 Me H 2-nPr OCH _Two 4-Me OS G7.50 Me H 2-nPr SCH _Two 4-Me OS G7.51 Me H 2-nPr OCH _Two 5-Me OS G7.52 Me H 2-nPr SCH _Two 5-Me OS G7.53 Me H 2-nPr OCH _Two 6-Me OS G7.54 Me H 2-nPr SCH _Two 6-Me OS G7.55 Me H 2-nPr OCH _Two 7-Me OS G7.56 Me H 2-nPr SCH _Two 7-Me OS G7.57 Me H 2-nPr OCH _Two 5-Et OS G7.58 Me H 2-nPr SCH _Two 5-Et OS G7.59 Me H 2-nPr OCH _Two 6-Et OS G7.60 Me H 2-nPr SCH _Two 6-Et OS G7.61 Me H 2-nPr OCH _Two 4-OMe OS G7.62 Me H 2-nPr SCH _Two 4-OMe OS G7.63 Me H 2-nPr OCH _Two 5-OMe OS G7.64 Me H 2-nPr SCH _Two 5-OMe OS G7.65 Me H 2-nPr OCH _Two 6-OMe OS G7.66 Me H 2-nPr SCH _Two 6-OMe OS G7.67 Me H 2-nPr OCH _Two 7-OMe OS G7.68 Me H 2-nPr SCH _Two 7-OMe OS G7.69 Me H 2-nPr OCH _Two 5-OEt OS G7.70 Me H 2-nPr SCH _Two 5-OEt OS G7.71 Me H 2-nPr OCH _Two 6-OEt OS G7.72 Me H 2-nPr SCH _Two 6-OEt OS G7.73 Me H 2-nPr OCH _Two 4-FOS G7.74 Me H 2-nPr SCH _Two 4-FOS G7.75 Me H 2-nPr OCH _Two 5-FOS G7.76 Me H 2-nPr SCH _Two 5-FOS G7.77 Me H 2-nPr OCH _Two 6-FOS G7.78 Me H 2-nPr SCH _Two 6-FOS G7.79 Me H 2-nPr OCH _Two 7-FOS G7.80 Me H 2-nPr SCH _Two 7-FOS G7.81 Me H 2-nPr OCH _Two 5-Cl OS G7.82 Me H 2-nPr SCH _Two 5-Cl OS G7.83 Me H 2-nPr OCH _Two 6-Cl OS G7.84 Me H 2-nPr SCH _Two 6-Cl OS G7.85 Me H 2-nPr OCH _Two 4-CF _Three OS G7.86 Me H 2-nPr SCH _Two 4-CF _Three OS G7.87 Me H 2-nPr OCH _Two 5-CF _Three OS G7.88 Me H 2-nPr SCH _Two 5-CF _Three OS G7.89 Me H 2-nPr OCH _Two 6-CF _Three OS G7.90 Me H 2-nPr SCH _Two 6-CF _Three OS G7.91 Me H 2-nPr OCH _Two 7-CF _Three OS G7.92 Me H 2-nPr SCH _Two 7-CF _Three OS G7.93 Me H 2-nPr OCH _Two 5-OCF _Three OS G7.94 Me H 2-nPr SCH _Two 5-OCF _Three OS G7.95 Me H 2-nPr OCH _Two 6-OCF _Three OS G7.96 Me H 2-nPr SCH _Two 6-OCF _Three OS G7.97 Me H 3-nPr OCH _Two 4-Me OS G7.98 Me H 3-nPr SCH _Two 4-Me OS G7.99 Me H 3-nPr OCH _Two 5-Me OS G7.100 Me H 3-nPr SCH _Two 5-Me OS G7.101 Me H 3-nPr OCH _Two 6-Me OS G7.102 Me H 3-nPr SCH _Two 6-Me OS G7.103 Me H 3-nPr OCH _Two 7-Me OS G7.104 Me H 3-nPr SCH _Two 7-Me OS G7.105 Me H 3-nPr OCH _Two 5-Et OS G7.106 Me H 3-nPr SCH _Two 5-Et OS G7.107 Me H 3-nPr OCH _Two 6-Et OS G7.108 Me H 3-nPr SCH _Two 6-Et OS G7.109 Me H 3-nPr OCH _Two 4-OMe OS G7.110 Me H 3-nPr SCH _Two 4-OMe OS G7.111 Me H 3-nPr OCH _Two 5-OMe OS G7.112 Me H 3-nPr SCH _Two 5-OMe OS G7.113 Me H 3-nPr OCH _Two 6-OMe OS G7.114 Me H 3-nPr SCH _Two 6-OMe OS G7.115 Me H 3-nPr OCH _Two 7-OMe OS G7.116 Me H 3-nPr SCH _Two 7-OMe OS G7.117 Me H 3-nPr OCH _Two 5-OEt OS G7.118 Me H 3-nPr SCH _Two 5-OEt OS G7.119 Me H 3-nPr OCH _Two 6-OEt OS G7.120 Me H 3-nPr SCH _Two 6-OEt OS G7.121 Me H 3-nPr OCH _Two 4-FOS G7.122 Me H 3-nPr SCH _Two 4-FOS G7.123 Me H 3-nPr OCH _Two 5-FOS G7.124 Me H 3-nPr SCH _Two 5-FOS G7.125 Me H 3-nPr OCH _Two 6-FOS G7.126 Me H 3-nPr SCH _Two 6-FOS G7.127 Me H 3-nPr OCH _Two 7-FOS G7.128 Me H 3-nPr SCH _Two 7-FOS G7.129 Me H 3-nPr OCH _Two 5-Cl OS G7.130 Me H 3-nPr SCH _Two 5-Cl OS G7.131 Me H 3-nPr OCH _Two 6-Cl OS G7.132 Me H 3-nPr SCH _Two 6-Cl OS G7.133 Me H 3-nPr OCH _Two 4-CF _Three OS G7.134 Me H 3-nPr SCH _Two 4-CF _Three OS G7.135 Me H 3-nPr OCH _Two 5-CF _Three OS G7.136 Me H 3-nPr SCH _Two 5-CF _Three OS G7.137 Me H 3-nPr OCH _Two 6-CF _Three OS G7.138 Me H 3-nPr SCH _Two 6-CF _Three OS G7.139 Me H 3-nPr OCH _Two 7-CF _Three OS G7.140 Me H 3-nPr SCH _Two 7-CF _Three OS G7.141 Me H 3-nPr OCH _Two 5-OCF _Three OS G7.142 Me H 3-nPr SCH _Two 5-OCF _Three OS G7.143 Me H 3-nPr OCH _Two 6-OCF _Three OS G7.144 Me H 3-nPr SCH _Two 6-OCF _Three OS G8.1 Me H 2-OMe OCH _Two 4-Me OS G8.2 Me H 2-OMe SCH _Two 4-Me OS G8.3 Me H 2-OMe OCH _Two 5-Me OS G8.4 Me H 2-OMe SCH _Two 5-Me OS G8.5 MeO H 2-OMe OCH _Two 5-Me OS G8.6 Me H 2-OMe OCH _Two 6-Me OS G8.7 Me H 2-OMe SCH _Two 6-Me OS G8.8 MeO H 2-OMe OCH _Two 6-Me OS G8.9 Me H 2-OMe OCH _Two 7-Me OS G8.10 Me H 2-OMe SCH _Two 7-Me OS G8.11 Me H 2-OMe OCH _Two 5-Et OS G8.12 Me H 2-OMe SCH _Two 5-Et OS G8.13 Me H 2-OMe OCH _Two 6-Et OS G8.14 Me H 2-OMe SCH _Two 6-Et OS G8.15 Me H 2-OMe OCH _Two 4-OMe OS G8.16 Me H 2-OMe SCH _Two 4-OMe OS G8.17 Me H 2-OMe OCH _Two 5-OMe OS G8.18 Me H 2-OMe SCH _Two 5-OMe OS G8.19 Me H 2-OMe OCH _Two 6-OMe OS G8.20 Me H 2-OMe SCH _Two 6-OMe OS G8.21 Me H 2-OMe OCH _Two 7-OMe OS G8.22 Me H 2-OMe SCH _Two 7-OMe OS G8.23 Me H 2-OMe OCH _Two 5-OEt OS G8.24 Me H 2-OMe SCH _Two 5-OEt OS G8.25 Me H 2-OMe OCH _Two 6-OEt OS G8.26 Me H 2-OMe SCH _Two 6-OEt OS G8.27 Me H 2-OMe OCH _Two 4-FOS G8.28 Me H 2-OMe SCH _Two 4-FOS G8.29 MeO H 2-OMe OCH _Two 4-FOS G8.30 MeO H 2-OMe OCH _Two 4-FOO G8.31 Me H 2-OMe OCH _Two 5-FOS 170-172 G8.32 Me H 2-OMe SCH _Two 5-FOS G8.33 MeO H 2-OMe OCH _Two 5-FOS 159-162 G8.34 Me H 2-OMe OCH _Two 5-FOO G8.35 MeO H 2-OMe OCH _Two 5-FOO G8.36 EtO H 2-OMe OCH _Two 5-FOS 157-159 G8.37 EtO H 2-OMe OCH _Two 5-FOO G8.38 Me H 2-OMe OCH _Two 6-FOS 155-159 G8.39 Me H 2-OMe SCH _Two 6-FOS G8.40 MeO H 2-OMe OCH _Two 6-FOS G8.41 MeO H 2-OMe OCH _Two 6-FOO G8.42 Me H 2-OMe OCH _Two 7-FOS G8.43 Me H 2-OMe SCH _Two 7-FOS G8.44 MeO H 2-OMe OCH _Two 7-FOS G8.45 MeO H 2-OMe OCH _Two 7-FOS G8.46 Me H 2-OMe OCH _Two 5-Cl OS G8.47 Me H 2-OMe SCH _Two 5-Cl OS G8.48 Me H 2-OMe OCH _Two 6-Cl OS G8.49 Me H 2-OMe SCH _Two 6-Cl OS G8.50 Me H 2-OMe OCH _Two 4-CF _Three OS G8.51 Me H 2-OMe SCH _Two 4-CF _Three OS G8.52 Me H 2-OMe OCH _Two 5-CF _Three OS G8.53 Me H 2-OMe SCH _Two 5-CF _Three OS G8.54 Me H 2-OMe OCH _Two 6-CF _Three OS G8.55 Me H 2-OMe SCH _Two 6-CF _Three OS G8.56 Me H 2-OMe OCH _Two 7-CF _Three OS G8.57 Me H 2-OMe SCH _Two 7-CF _Three OS G8.58 Me H 2-OMe OCH _Two 5-OCF _Three OS G8.59 Me H 2-OMe SCH _Two 5-OCF _Three OS G8.60 Me H 2-OMe OCH _Two 6-OCF _Three OS G8.61 Me H 2-OMe SCH _Two 6-OCF _Three OS G8.62 Me H 2-OMe OCH _Two 4,5-Me _Two OS G9.1 Me H 2-OMe SCH _Two 4,5-Me _Two OS G9.2 Me H 2-OMe OCH _Two 4,6-Me _Two OS G9.3 Me H 2-OMe SCH _Two 4,6-Me _Two OS G9.4 Me H 2-OMe OCH _Two 4,7-Me _Two OS G9.5 Me H 2-OMe SCH _Two 4,7-Me _Two OS G9.6 Me H 2-OMe OCH _Two 5,6-Me _Two OS G9.7 Me H 2-OMe SCH _Two 5,6-Me _Two OS G9.8 Me H 2-OMe OCH _Two 5,7-Me _Two OS G9.9 Me H 2-OMe SCH _Two 5,7-Me _Two OS G9.10 Me H 2-OMe OCH _Two 6,7-Me _Two OS G9.11 Me H 2-OMe SCH _Two 6,7-Me _Two OS G9.12 Me H 2-OMe OCH _Two 4,5- (OMe) _Two OS G9.13 Me H 2-OMe SCH _Two 4,5- (OMe) _Two OS G9.14 Me H 2-OMe OCH _Two 4,6- (OMe) _Two OS G9.15 Me H 2-OMe SCH _Two 4,6- (OMe) _Two OS G9.16 Me H 2-OMe OCH _Two 4,7- (OMe) _Two OS G9.17 Me H 2-OMe SCH _Two 4,7- (OMe) _Two OS G9.18 Me H 2-OMe OCH _Two 5,6- (OMe) _Two OS G9.19 Me H 2-OMe SCH _Two 5,6- (OMe) _Two OS G9.20 Me H 2-OMe OCH _Two 5,7- (OMe) _Two OS G9.21 Me H 2-OMe SCH _Two 5,7- (OMe) _Two OS G9.22 Me H 2-OMe OCH _Two 6,7- (OMe) _Two OS G9.23 Me H 2-OMe SCH _Two 6,7- (OMe) _Two OS G9.24 Me H 2-OMe OCH _Two 4,5-F _Two OS G9.25 Me H 2-OMe SCH _Two 4,5-F _Two OS G9.26 Me H 2-OMe OCH _Two 4,6-F _Two OS G9.27 Me H 2-OMe SCH _Two 4,6-F _Two OS G9.28 Me H 2-OMe OCH _Two 4,7-F _Two OS G9.29 Me H 2-OMe SCH _Two 4,7-F _Two OS G9.30 Me H 2-OMe OCH _Two 5,6-F _Two OS G9.31 Me H 2-OMe SCH _Two 5,6-F _Two OS G9.32 Me H 2-OMe OCH _Two 5,7-F _Two OS G9.33 Me H 2-OMe SCH _Two 5,7-F _Two OS G9.34 Me H 2-OMe OCH _Two 6,7-F _Two OS G9.35 Me H 2-OMe SCH _Two 6,7-F _Two OS G9.36 Me H 2-OMe OCH _Two 4,5-Cl _Two OS G9.37 Me H 2-OMe SCH _Two 4,5-Cl _Two OS G9.38 Me H 2-OMe OCH _Two 4,6-Cl _Two OS G9.39 Me H 2-OMe SCH _Two 4,6-Cl _Two OS G9.40 Me H 2-OMe OCH _Two 4,7-Cl _Two OS G9.41 Me H 2-OMe SCH _Two 4,7-Cl _Two OS G9.42 Me H 2-OMe OCH _Two 5,6-Cl _Two OS G9.43 Me H 2-OMe SCH _Two 5,6-Cl _Two OS G9.44 Me H 2-OMe OCH _Two 5,7-Cl _Two OS G9.45 Me H 2-OMe SCH _Two 5,7-Cl _Two OS G9.46 Me H 2-OMe OCH _Two 6,7-Cl _Two OS G9.47 Me H 2-OMe SCH _Two 6,7-Cl _Two OS G9.48 Me H 2-OMe OCH _Two 4,5- (CF _Three ) _Two OS G9.49 Me H 2-OMe SCH _Two 4,5- (CF _Three ) _Two OS G9.50 Me H 2-OMe OCH _Two 4,6- (CF _Three ) _Two OS G9.51 Me H 2-OMe SCH _Two 4,6- (CF _Three ) _Two OS G9.52 Me H 2-OMe OCH _Two 4,7- (CF _Three ) _Two OS G9.53 Me H 2-OMe SCH _Two 4,7- (CF _Three ) _Two OS G9.54 Me H 2-OMe OCH _Two 5,6- (CF _Three ) _Two OS G9.55 Me H 2-OMe SCH _Two 5,6- (CF _Three ) _Two OS G9.56 Me H 2-OMe OCH _Two 5,7- (CF _Three ) _Two OS G9.57 Me H 2-OMe SCH _Two 5,7- (CF _Three ) _Two OS G9.58 Me H 2-OMe OCH _Two 6,7- (CF _Three ) _Two OS G9.59 Me H 2-OMe SCH _Two 6,7- (CF _Three ) _Two OS G9.60 Me H 2-OMe OCH _Two 4-F, 5-Me OS G9.61 Me H 2-OMe SCH _Two 4-F, 5-Me OS G9.62 Me H 2-OMe OCH _Two 4-F, 6-Me OS G9.63 Me H 2-OMe SCH _Two 4-F, 6-Me OS G9.64 Me H 2-OMe OCH _Two 4-F, 7-Me OS G9.65 Me H 2-OMe SCH _Two 4-F, 7-Me OS G9.66 Me H 2-OMe OCH _Two 4-Me, 5-FOS G9.67 Me H 2-OMe SCH _Two 4-Me, 5-FOS G9.68 Me H 2-OMe OCH _Two 5-F, 6-Me OS G9.69 Me H 2-OMe SCH _Two 5-F, 6-Me OS G9.70 Me H 2-OMe OCH _Two 5-F, 7-Me OS G9.71 Me H 2-OMe SCH _Two 5-F, 7-Me OS G9.72 Me H 2-OMe OCH _Two 4-Me, 6-FOS G9.73 Me H 2-OMe SCH _Two 4-Me, 6-FOS G9.74 Me H 2-OMe OCH _Two 5-Me, 6-FOS G9.75 Me H 2-OMe SCH _Two 5-Me, 6-FOS G9.76 Me H 2-OMe OCH _Two 6-F, 7-Me OS G9.77 Me H 2-OMe SCH _Two 6-F, 7-Me OS G9.78 Me H 2-OMe OCH _Two 4-Me, 7-FOS G9.79 Me H 2-OMe SCH _Two 4-Me, 7-FOS G9.80 Me H 2-OMe OCH _Two 5-Me, 7-FOS G9.81 Me H 2-OMe SCH _Two 5-Me, 7-FOS G9.82 Me H 2-OMe OCH _Two 6-Me, 7-FOS G9.83 Me H 2-OMe SCH _Two 6-Me, 7-FOS G9.84 Me H 2-OMe OCH _Two 4-Cl, 5-Me OS G9.85 Me H 2-OMe SCH _Two 4-Cl, 5-Me OS G9.86 Me H 2-OMe OCH _Two 4-Cl, 6-Me OS G9.87 Me H 2-OMe SCH _Two 4-Cl, 6-Me OS G9.88 Me H 2-OMe OCH _Two 4-Cl, 7-Me OS G9.89 Me H 2-OMe SCH _Two 4-Cl, 7-Me OS G9.90 Me H 2-OMe OCH _Two 4-Me, 5-Cl OS G9.91 Me H 2-OMe SCH _Two 4-Me, 5-Cl OS G9.92 Me H 2-OMe OCH _Two 5-Cl, 6-Me OS G9.93 Me H 2-OMe SCH _Two 5-Cl, 6-Me OS G9.94 Me H 2-OMe OCH _Two 5-Cl, 7-Me OS G9.95 Me H 2-OMe SCH _Two 5-Cl, 7-Me OS G9.96 Me H 2-OMe OCH _Two 4-Me, 6-Cl OS G9.97 Me H 2-OMe SCH _Two 4-Me, 6-Cl OS G9.98 Me H 2-OMe OCH _Two 5-Me, 6-Cl OS G9.99 Me H 2-OMe SCH _Two 5-Me, 6-Cl OS G9.100 Me H 2-OMe OCH _Two 6-Cl, 7-Me OS G9.101 Me H 2-OMe SCH _Two 6-Cl, 7-Me OS G9.102 Me H 2-OMe OCH _Two 4-Me, 7-Cl OS G9.103 Me H 2-OMe SCH _Two 4-Me, 7-Cl OS G9.104 Me H 2-OMe OCH _Two 5-Me, 7-Cl OS G9.105 Me H 2-OMe SCH _Two 5-Me, 7-Cl OS G9.106 Me H 2-OMe OCH _Two 6-Me, 7-Cl OS G9.107 Me H 2-OMe SCH _Two 6-Me, 7-Cl OS G9.108 Me H 2-OMe OCH _Two 4-Cl, 5-FOS G9.109 Me H 2-OMe SCH _Two 4-Cl, 5-FOS G9.110 Me H 2-OMe OCH _Two 4-Cl, 6-FOS G9.111 Me H 2-OMe SCH _Two 4-Cl, 6-FOS G9.112 Me H 2-OMe OCH _Two 4-Cl, 7-FOS G9.113 Me H 2-OMe SCH _Two 4-Cl, 7-FOS G9.114 Me H 2-OMe OCH _Two 4-F, 5-Cl OS G9.115 Me H 2-OMe SCH _Two 4-F, 5-Cl OS G9.116 Me H 2-OMe OCH _Two 5-Cl, 6-FOS G9.117 Me H 2-OMe SCH _Two 5-Cl, 6-FOS G9.118 Me H 2-OMe OCH _Two 5-Cl, 7-FOS G9.119 Me H 2-OMe SCH _Two 5-Cl, 7-FOS G9.120 Me H 2-OMe OCH _Two 4-F, 6-Cl OS G9.121 Me H 2-OMe SCH _Two 4-F, 6-Cl OS G9.122 Me H 2-OMe OCH _Two 5-F, 6-Cl OS G9.123 Me H 2-OMe SCH _Two 5-F, 6-Cl OS G9.124 Me H 2-OMe OCH _Two 7-F, 6-Cl OS G9.125 Me H 2-OMe SCH _Two 7-F, 6-Cl OS G9.126 Me H 2-OMe OCH _Two 4-F, 7-Cl OS G9.127 Me H 2-OMe SCH _Two 4-F, 7-Cl OS G9.128 Me H 2-OMe OCH _Two 5-F, 7-Cl OS G9.129 Me H 2-OMe SCH _Two 5-F, 7-Cl OS G9.130 Me H 2-OMe OCH _Two 6-F, 7-Cl OS G9.131 Me H 2-OMe SCH _Two 6-F, 7-Cl OS G10.1 Me H 3-OMe OCH _Two 4-Me OS G10.2 Me H 3-OMe SCH _Two 4-Me OS G10.3 Me H 3-OMe OCH _Two 5-Me OS G10.4 Me H 3-OMe SCH _Two 5-Me OS G10.5 Me H 3-OMe OCH _Two 6-Me OS G10.6 Me H 3-OMe SCH _Two 6-Me OS G10.7 Me H 3-OMe OCH _Two 7-Me OS G10.8 Me H 3-OMe SCH _Two 7-Me OS G10.9 Me H 3-OMe OCH _Two 5-Et OS G10.10 Me H 3-OMe SCH _Two 5-Et OS G10.11 Me H 3-OMe OCH _Two 6-Et OS G10.12 Me H 3-OMe SCH _Two 6-Et OS G10.13 Me H 3-OMe OCH _Two 4-OMe OS G10.14 Me H 3-OMe SCH _Two 4-OMe OS G10.15 Me H 3-OMe OCH _Two 5-OMe OS G10.16 Me H 3-OMe SCH _Two 5-OMe OS G10.17 Me H 3-OMe OCH _Two 6-OMe OS G10.18 Me H 3-OMe SCH _Two 6-OMe OS G10.19 Me H 3-OMe OCH _Two 7-OMe OS G10.20 Me H 3-OMe SCH _Two 7-OMe OS G10.21 Me H 3-OMe OCH _Two 5-OEt OS G10.22 Me H 3-OMe SCH _Two 5-OEt OS G10.23 Me H 3-OMe OCH _Two 6-OEt OS G10.24 Me H 3-OMe SCH _Two 6-OEt OS G10.25 Me H 3-OMe OCH _Two 4-FOS G10.26 Me H 3-OMe SCH _Two 4-FOS G10.27 Me H 3-OMe OCH _Two 5-FOS G10.28 Me H 3-OMe SCH _Two 5-FOS G10.29 MeO H 3-OMe OCH _Two 5-FOS G10.30 Me H 3-OMe OCH _Two 6-FOS G10.31 Me H 3-OMe SCH _Two 6-FOS G10.32 MeO H 3-OMe OCH _Two 6-FOS G10.33 Me H 3-OMe OCH _Two 7-FOS G10.34 Me H 3-OMe SCH _Two 7-FOS G10.35 Me H 3-OMe OCH _Two 5-Cl OS G10.36 Me H 3-OMe SCH _Two 5-Cl OS G10.37 Me H 3-OMe OCH _Two 6-Cl OS G10.38 Me H 3-OMe SCH _Two 6-Cl OS G10.39 Me H 3-OMe OCH _Two 4-CF _Three OS G10.40 Me H 3-OMe SCH _Two 4-CF _Three OS G10.41 Me H 3-OMe OCH _Two 5-CF _Three OS G10.42 Me H 3-OMe SCH _Two 5-CF _Three OS G10.43 Me H 3-OMe OCH _Two 6-CF _Three OS G10.44 Me H 3-OMe SCH _Two 6-CF _Three OS G10.45 Me H 3-OMe OCH _Two 7-CF _Three OS G10.46 Me H 3-OMe SCH _Two 7-CF _Three OS G10.47 Me H 3-OMe OCH _Two 5-OCF _Three OS G10.48 Me H 3-OMe SCH _Two 5-OCF _Three OS G10.49 Me H 3-OMe OCH _Two 6-OCF _Three OS G10.50 Me H 3-OMe SCH _Two 6-OCF _Three OS G10.51 Me H 2-OEt OCH _Two 5-FOS 177.5-179 G10.52 Me H 2-OEt SCH _Two 5-FOS G10.53 Me H 2-OEt OCH _Two 5-FOO G10.54 MeO H 2-OEt OCH _Two 5-FOS G10.55 MeO H 2-OEt SCH _Two 5-FOS G10.56 MeO H 2-OEt OCH _Two 5-FOO G10.57 Me H 2-CHF _Two OCH _Two 5-FOS 180-185 G10.58 MeO H 2-CHF _Two OCH _Two 5-FOS G10.59 Me H 2-CHF _Two OCH _Two 5-FOO G10.60 MeO H 2-CHF _Two OCH _Two 5-FOO G10.61 Me H 2-OCHF _Two OCH _Two 5-FOS 137-138 G10.62 MeO H 2-OCHF _Two OCH _Two 5-FOS G10.63 Me H 2-OCH _Two CF _Three OCH _Two 5-FOS 167-168 G10.64 MeO H 2-OCH _Two CF _Three OCH _Two 5-FOS G10.65 Me H 2-OCH _Two CF _Three OCH _Two 5-FOO G10.66 MeO H 2-OCH _Two CF _Three OCH _Two 5-FOO G11.1 Me H 2-CH _Two OMe OCH _Two 4-Me OS G11.2 Me H 2-CH _Two OMe SCH _Two 4-Me OS G11.3 Me H 2-CH _Two OMe OCH _Two 5-Me OS G11.4 Me H 2-CH _Two OMe SCH _Two 5-Me OS G11.5 Me H 2-CH _Two OMe OCH _Two 6-Me OS G11.6 Me H 2-CH _Two OMe SCH _Two 6-Me OS G11.7 Me H 2-CH _Two OMe OCH _Two 7-Me OS G11.8 Me H 2-CH _Two OMe SCH _Two 7-Me OS G11.9 Me H 2-CH _Two OMe OCH _Two 5-Et OS G11.10 Me H 2-CH _Two OMe SCH _Two 5-Et OS G11.11 Me H 2-CH _Two OMe OCH _Two 6-Et OS G11.12 Me H 2-CH _Two OMe SCH _Two 6-Et OS G11.13 Me H 2-CH _Two OMe OCH _Two 4-OMe OS G11.14 Me H 2-CH _Two OMe SCH _Two 4-OMe OS G11.15 Me H 2-CH _Two OMe OCH _Two 5-OMe OS G11.16 Me H 2-CH _Two OMe SCH _Two 5-OMe OS G11.17 Me H 2-CH _Two OMe OCH _Two 6-OMe OS G11.18 Me H 2-CH _Two OMe SCH _Two 6-OMe OS G11.19 Me H 2-CH _Two OMe OCH _Two 7-OMe OS G11.20 Me H 2-CH _Two OMe SCH _Two 7-OMe OS G11.21 Me H 2-CH _Two OMe OCH _Two 5-OEt OS G11.22 Me H 2-CH _Two OMe SCH _Two 5-OEt OS G11.23 Me H 2-CH _Two OMe OCH _Two 6-OEt OS G11.24 Me H 2-CH _Two OMe SCH _Two 6-OEt OS G11.25 Me H 2-CH _Two OMe OCH _Two 4-FOS G11.26 Me H 2-CH _Two OMe SCH _Two 4-FOS G11.27 Me H 2-CH _Two OMe OCH _Two 5-FOS G11.28 Me H 2-CH _Two OMe SCH _Two 5-FOS G11.29 Me H 2-CH _Two OMe OCH _Two 6-FOS G11.30 Me H 2-CH _Two OMe SCH _Two 6-FOS G11.31 Me H 2-CH _Two OMe OCH _Two 7-FOS G11.32 Me H 2-CH _Two OMe SCH _Two 7-FOS G11.33 Me H 2-CH _Two OMe OCH _Two 5-Cl OS G11.34 Me H 2-CH _Two OMe SCH _Two 5-Cl OS G11.35 Me H 2-CH _Two OMe OCH _Two 6-Cl OS G11.36 Me H 2-CH _Two OMe SCH _Two 6-Cl OS G11.37 Me H 2-CH _Two OMe OCH _Two 4-CF _Three OS G11.38 Me H 2-CH _Two OMe SCH _Two 4-CF _Three OS G11.39 Me H 2-CH _Two OMe OCH _Two 5-CF _Three OS G11.40 Me H 2-CH _Two OMe SCH _Two 5-CF _Three OS G11.41 Me H 2-CH _Two OMe OCH _Two 6-CF _Three OS G11.42 Me H 2-CH _Two OMe SCH _Two 6-CF _Three OS G11.43 Me H 2-CH _Two OMe OCH _Two 7-CF _Three OS G11.44 Me H 2-CH _Two OMe SCH _Two 7-CF _Three OS G11.45 Me H 2-CH _Two OMe OCH _Two 5-OCF _Three OS G11.46 Me H 2-CH _Two OMe SCH _Two 5-OCF _Three OS G11.47 Me H 2-CH _Two OMe OCH _Two 6-OCF _Three OS G11.48 Me H 2-CH _Two OMe SCH _Two 6-OCF _Three OS G11.49 Me H 3-CH _Two OMe OCH _Two 4-Me OS G11.50 Me H 3-CH _Two OMe SCH _Two 4-Me OS G11.51 Me H 3-CH _Two OMe OCH _Two 5-Me OS G11.52 Me H 3-CH _Two OMe SCH _Two 5-Me OS G11.53 Me H 3-CH _Two OMe OCH _Two 6-Me OS G11.54 Me H 3-CH _Two OMe SCH _Two 6-Me OS G11.55 Me H 3-CH _Two OMe OCH _Two 7-Me OS G11.56 Me H 3-CH _Two OMe SCH _Two 7-Me OS G11.57 Me H 3-CH _Two OMe OCH _Two 5-Et OS G11.58 Me H 3-CH _Two OMe SCH _Two 5-Et OS G11.59 Me H 3-CH _Two OMe OCH _Two 6-Et OS G11.60 Me H 3-CH _Two OMe SCH _Two 6-Et OS G11.61 Me H 3-CH _Two OMe OCH _Two 4-OMe OS G11.62 Me H 3-CH _Two OMe SCH _Two 4-OMe OS G11.63 Me H 3-CH _Two OMe OCH _Two 5-OMe OS G11.64 Me H 3-CH _Two OMe SCH _Two 5-OMe OS G11.65 Me H 3-CH _Two OMe OCH _Two 6-OMe OS G11.66 Me H 3-CH _Two OMe SCH _Two 6-OMe OS G11.67 Me H 3-CH _Two OMe OCH _Two 7-OMe OS G11.68 Me H 3-CH _Two OMe SCH _Two 7-OMe OS G11.69 Me H 3-CH _Two OMe OCH _Two 5-OEt OS G11.70 Me H 3-CH _Two OMe SCH _Two 5-OEt OS G11.71 Me H 3-CH _Two OMe OCH _Two 6-OEt OS G11.72 Me H 3-CH _Two OMe SCH _Two 6-OEt OS G11.73 Me H 3-CH _Two OMe OCH _Two 4-FOS G11.74 Me H 3-CH _Two OMe SCH _Two 4-FOS G11.75 Me H 3-CH _Two OMe OCH _Two 5-FOS G11.76 Me H 3-CH _Two OMe SCH _Two 5-FOS G11.77 Me H 3-CH _Two OMe OCH _Two 6-FOS G11.78 Me H 3-CH _Two OMe SCH _Two 6-FOS G11.79 Me H 3-CH _Two OMe OCH _Two 7-FOS G11.80 Me H 3-CH _Two OMe SCH _Two 7-FOS G11.81 Me H 3-CH _Two OMe OCH _Two 5-Cl OS G11.82 Me H 3-CH _Two OMe SCH _Two 5-Cl OS G11.83 Me H 3-CH _Two OMe OCH _Two 6-Cl OS G11.84 Me H 3-CH _Two OMe SCH _Two 6-Cl OS G11.85 Me H 3-CH _Two OMe OCH _Two 4-CF _Three OS G11.86 Me H 3-CH _Two OMe SCH _Two 4-CF _Three OS G11.87 Me H 3-CH _Two OMe OCH _Two 5-CF _Three OS G11.88 Me H 3-CH _Two OMe SCH _Two 5-CF _Three OS G11.89 Me H 3-CH _Two OMe OCH _Two 6-CF _Three OS G11.90 Me H 3-CH _Two OMe SCH _Two 6-CF _Three OS G11.91 Me H 3-CH _Two OMe OCH _Two 7-CF _Three OS G11.92 Me H 3-CH _Two OMe SCH _Two 7-CF _Three OS G11.93 Me H 3-CH _Two OMe OCH _Two 5-OCF _Three OS G11.94 Me H 3-CH _Two OMe SCH _Two 5-OCF _Three OS G11.95 Me H 3-CH _Two OMe OCH _Two 6-OCF _Three OS G11.96 Me H 3-CH _Two OMe SCH _Two 6-OCF _Three OS G12.1 Me H 2-CH _Two OEt OCH _Two 4-Me OS G12.2 Me H 2-CH _Two OEt SCH _Two 4-Me OS G12.3 Me H 2-CH _Two OEt OCH _Two 5-Me OS G12.4 Me H 2-CH _Two OEt SCH _Two 5-Me OS G12.5 Me H 2-CH _Two OEt OCH _Two 6-Me OS G12.6 Me H 2-CH _Two OEt SCH _Two 6-Me OS G12.7 Me H 2-CH _Two OEt OCH _Two 7-Me OS G12.8 Me H 2-CH _Two OEt SCH _Two 7-Me OS G12.9 Me H 2-CH _Two OEt OCH _Two 5-Et OS G12.10 Me H 2-CH _Two OEt SCH _Two 5-Et OS G12.11 Me H 2-CH _Two OEt OCH _Two 6-Et OS G12.12 Me H 2-CH _Two OEt SCH _Two 6-Et OS G12.13 Me H 2-CH _Two OEt OCH _Two 4-OMe OS G12.14 Me H 2-CH _Two OEt SCH _Two 4-OMe OS G12.15 Me H 2-CH _Two OEt OCH _Two 5-OMe OS G12.16 Me H 2-CH _Two OEt SCH _Two 5-OMe OS G12.17 Me H 2-CH _Two OEt OCH _Two 6-OMe OS G12.18 Me H 2-CH _Two OEt SCH _Two 6-OMe OS G12.19 Me H 2-CH _Two OEt OCH _Two 7-OMe OS G12.20 Me H 2-CH _Two OEt SCH _Two 7-OMe OS G12.21 Me H 2-CH _Two OEt OCH _Two 5-OEt OS G12.22 Me H 2-CH _Two OEt SCH _Two 5-OEt OS G12.23 Me H 2-CH _Two OEt OCH _Two 6-OEt OS G12.24 Me H 2-CH _Two OEt SCH _Two 6-OEt OS G12.25 Me H 2-CH _Two OEt OCH _Two 4-FOS G12.26 Me H 2-CH _Two OEt SCH _Two 4-FOS G12.27 Me H 2-CH _Two OEt OCH _Two 5-FOS G12.28 Me H 2-CH _Two OEt SCH _Two 5-FOS G12.29 Me H 2-CH _Two OEt OCH _Two 6-FOS G12.30 Me H 2-CH _Two OEt SCH _Two 6-FOS G12.31 Me H 2-CH _Two OEt OCH _Two 7-FOS G12.32 Me H 2-CH _Two OEt SCH _Two 7-FOS G12.33 Me H 2-CH _Two OEt OCH _Two 5-Cl OS G12.34 Me H 2-CH _Two OEt SCH _Two 5-Cl OS G12.35 Me H 2-CH _Two OEt OCH _Two 6-Cl OS G12.36 Me H 2-CH _Two OEt SCH _Two 6-Cl OS G12.37 Me H 2-CH _Two OEt OCH _Two 4-CF _Three OS G12.38 Me H 2-CH _Two OEt SCH _Two 4-CF _Three OS G12.39 Me H 2-CH _Two OEt OCH _Two 5-CF _Three OS G12.40 Me H 2-CH _Two OEt SCH _Two 5-CF _Three OS G12.41 Me H 2-CH _Two OEt OCH _Two 6-CF _Three OS G12.42 Me H 2-CH _Two OEt SCH _Two 6-CF _Three OS G12.43 Me H 2-CH _Two OEt OCH _Two 7-CF _Three OS G12.44 Me H 2-CH _Two OEt SCH _Two 7-CF _Three OS G12.45 Me H 2-CH _Two OEt OCH _Two 5-OCF _Three OS G12.46 Me H 2-CH _Two OEt SCH _Two 5-OCF _Three OS G12.47 Me H 2-CH _Two OEt OCH _Two 6-OCF _Three OS G12.48 Me H 2-CH _Two OEt SCH _Two 6-OCF _Three OS G12.49 Me H 3-CH _Two OEt OCH _Two 4-Me OS G12.50 Me H 3-CH _Two OEt SCH _Two 4-Me OS G15.51 Me H 3-CH _Two OEt OCH _Two 5-Me OS G12.52 Me H 3-CH _Two OEt SCH _Two 5-Me OS G12.53 Me H 3-CH _Two OEt OCH _Two 6-Me OS G12.54 Me H 3-CH _Two OEt SCH _Two 6-Me OS G12.55 Me H 3-CH _Two OEt OCH _Two 7-Me OS G12.56 Me H 3-CH _Two OEt SCH _Two 7-Me OS G12.57 Me H 3-CH _Two OEt OCH _Two 5-Et OS G12.58 Me H 3-CH _Two OEt SCH _Two 5-Et OS G12.59 Me H 3-CH _Two OEt OCH _Two 6-Et OS G12.60 Me H 3-CH _Two OEt SCH _Two 6-Et OS G12.61 Me H 3-CH _Two OEt OCH _Two 4-OMe OS G12.62 Me H 3-CH _Two OEt SCH _Two 4-OMe OS G12.63 Me H 3-CH _Two OEt OCH _Two 5-OMe OS G12.64 Me H 3-CH _Two OEt SCH _Two 5-OMe OS G12.65 Me H 3-CH _Two OEt OCH _Two 6-OMe OS G12.66 Me H 3-CH _Two OEt SCH _Two 6-OMe OS G12.67 Me H 3-CH _Two OEt OCH _Two 7-OMe OS G12.68 Me H 3-CH _Two OEt SCH _Two 7-OMe OS G12.69 Me H 3-CH _Two OEt OCH _Two 5-OEt OS G12.70 Me H 3-CH _Two OEt SCH _Two 5-OEt OS G12.71 Me H 3-CH _Two OEt OCH _Two 6-OEt OS G12.72 Me H 3-CH _Two OEt SCH _Two 6-OEt OS G12.73 Me H 3-CH _Two OEt OCH _Two 4-FOS G12.74 Me H 3-CH _Two OEt SCH _Two 4-FOS G12.75 Me H 3-CH _Two OEt OCH _Two 5-FOS G12.76 Me H 3-CH _Two OEt SCH _Two 5-FOS G12.77 Me H 3-CH _Two OEt OCH _Two 6-FOS G12.78 Me H 3-CH _Two OEt SCH _Two 6-FOS G12.79 Me H 3-CH _Two OEt OCH _Two 7-FOS G12.80 Me H 3-CH _Two OEt SCH _Two 7-FOS G12.81 Me H 3-CH _Two OEt OCH _Two 5-Cl OS G12.82 Me H 3-CH _Two OEt SCH _Two 5-Cl OS G12.83 Me H 3-CH _Two OEt OCH _Two 6-Cl OS G12.84 Me H 3-CH _Two OEt SCH _Two 6-Cl OS G12.85 Me H 3-CH _Two OEt OCH _Two 4-CF _Three OS G12.86 Me H 3-CH _Two OEt SCH _Two 4-CF _Three OS G12.87 Me H 3-CH _Two OEt OCH _Two 5-CF _Three OS G12.88 Me H 3-CH _Two OEt SCH _Two 5-CF _Three OS G12.89 Me H 3-CH _Two OEt OCH _Two 6-CF _Three OS G12.90 Me H 3-CH _Two OEt SCH _Two 6-CF _Three OS G12.91 Me H 3-CH _Two OEt OCH _Two 7-CF _Three OS G12.92 Me H 3-CH _Two OEt SCH _Two 7-CF _Three OS G12.93 Me H 3-CH _Two OEt OCH _Two 5-OCF _Three OS G12.94 Me H 3-CH _Two OEt SCH _Two 5-OCF _Three OS G12.95 Me H 3-CH _Two OEt OCH _Two 6-OCF _Three OS G12.96 Me H 3-CH _Two OEt SCH _Two 6-OCF _Three OS ────────────────────────────────────

【００５８】[0058]

【表８】 ──────────────────────────────────── 番号 R¹ R² (R³)n ACR⁴(R⁵) (R⁶)m X Q 融点（℃） ──────────────────────────────────── H1.1 Me H 2-CH₂Cl OCH₂ 4-Me O S H1.2 Me H 2-CH₂Cl SCH₂ 4-Me O S H1.3 Me H 2-CH₂Cl OCH₂ 5-Me O S H1.4 Me H 2-CH₂Cl SCH₂ 5-Me O S H1.5 Me H 2-CH₂Cl OCH₂ 6-Me O S H1.6 Me H 2-CH₂Cl SCH₂ 6-Me O S H1.7 Me H 2-CH₂Cl OCH₂ 7-Me O S H1.8 Me H 2-CH₂Cl SCH₂ 7-Me O S H1.9 Me H 2-CH₂Cl OCH₂ 5-Et O S H1.10 Me H 2-CH₂Cl SCH₂ 5-Et O S H1.11 Me H 2-CH₂Cl OCH₂ 6-Et O S H1.12 Me H 2-CH₂Cl SCH₂ 6-Et O S H1.13 Me H 2-CH₂Cl OCH₂ 4-OMe O S H1.14 Me H 2-CH₂Cl SCH₂ 4-OMe O S H1.15 Me H 2-CH₂Cl OCH₂ 5-OMe O S H1.16 Me H 2-CH₂Cl SCH₂ 5-OMe O S H1.17 Me H 2-CH₂Cl OCH₂ 6-OMe O S H1.18 Me H 2-CH₂Cl SCH₂ 6-OMe O S H1.19 Me H 2-CH₂Cl OCH₂ 7-OMe O S H1.20 Me H 2-CH₂Cl SCH₂ 7-OMe O S H1.21 Me H 2-CH₂Cl OCH₂ 5-OEt O S H1.22 Me H 2-CH₂Cl SCH₂ 5-OEt O S H1.23 Me H 2-CH₂Cl OCH₂ 6-OEt O S H1.24 Me H 2-CH₂Cl SCH₂ 6-OEt O S H1.25 Me H 2-CH₂Cl OCH₂ 4-F O S H1.26 Me H 2-CH₂Cl SCH₂ 4-F O S H1.27 Me H 2-CH₂Cl OCH₂ 5-F O S H1.28 Me H 2-CH₂Cl SCH₂ 5-F O S H1.29 Me H 2-CH₂Cl OCH₂ 6-F O S H1.30 Me H 2-CH₂Cl SCH₂ 6-F O S H1.31 Me H 2-CH₂Cl OCH₂ 7-F O S H1.32 Me H 2-CH₂Cl SCH₂ 7-F O S H1.33 Me H 2-CH₂Cl OCH₂ 5-Cl O S H1.34 Me H 2-CH₂Cl SCH₂ 5-Cl O S H1.35 Me H 2-CH₂Cl OCH₂ 6-Cl O S H1.36 Me H 2-CH₂Cl SCH₂ 6-Cl O S H1.37 Me H 2-CH₂Cl OCH₂ 4-CF₃ O S H1.38 Me H 2-CH₂Cl SCH₂ 4-CF₃ O S H1.39 Me H 2-CH₂Cl OCH₂ 5-CF₃ O S H1.40 Me H 2-CH₂Cl SCH₂ 5-CF₃ O S H1.41 Me H 2-CH₂Cl OCH₂ 6-CF₃ O S H1.42 Me H 2-CH₂Cl SCH₂ 6-CF₃ O S H1.43 Me H 2-CH₂Cl OCH₂ 7-CF₃ O S H1.44 Me H 2-CH₂Cl SCH₂ 7-CF₃ O S H1.45 Me H 2-CH₂Cl OCH₂ 5-OCF₃ O S H1.46 Me H 2-CH₂Cl SCH₂ 5-OCF₃ O S H1.47 Me H 2-CH₂Cl OCH₂ 6-OCF₃ O S H1.48 Me H 2-CH₂Cl SCH₂ 6-OCF₃ O S H1.49 Me H 3-CH₂Cl OCH₂ 4-Me O S H1.50 Me H 3-CH₂Cl SCH₂ 4-Me O S H1.51 Me H 3-CH₂Cl OCH₂ 5-Me O S H1.52 Me H 3-CH₂Cl SCH₂ 5-Me O S H1.54 Me H 3-CH₂Cl SCH₂ 6-Me O S H1.55 Me H 3-CH₂Cl OCH₂ 7-Me O S H1.56 Me H 3-CH₂Cl SCH₂ 7-Me O S H1.57 Me H 3-CH₂Cl OCH₂ 5-Et O S H1.58 Me H 3-CH₂Cl SCH₂ 5-Et O S H1.59 Me H 3-CH₂Cl OCH₂ 6-Et O S H1.60 Me H 3-CH₂Cl SCH₂ 6-Et O S H1.61 Me H 3-CH₂Cl OCH₂ 4-OMe O S H1.62 Me H 3-CH₂Cl SCH₂ 4-OMe O S H1.63 Me H 3-CH₂Cl OCH₂ 5-OMe O S H1.64 Me H 3-CH₂Cl SCH₂ 5-OMe O S H1.65 Me H 3-CH₂Cl OCH₂ 6-OMe O S H1.66 Me H 3-CH₂Cl SCH₂ 6-OMe O S H1.67 Me H 3-CH₂Cl OCH₂ 7-OMe O S H1.68 Me H 3-CH₂Cl SCH₂ 7-OMe O S H1.69 Me H 3-CH₂Cl OCH₂ 5-OEt O S H1.70 Me H 3-CH₂Cl SCH₂ 5-OEt O S H1.71 Me H 3-CH₂Cl OCH₂ 6-OEt O S H1.72 Me H 3-CH₂Cl SCH₂ 6-OEt O S H1.73 Me H 3-CH₂Cl OCH₂ 4-F O S H1.74 Me H 3-CH₂Cl SCH₂ 4-F O S H1.75 Me H 3-CH₂Cl OCH₂ 5-F O S H1.76 Me H 3-CH₂Cl SCH₂ 5-F O S H1.77 Me H 3-CH₂Cl OCH₂ 6-F O S H1.78 Me H 3-CH₂Cl SCH₂ 6-F O S H1.79 Me H 3-CH₂Cl OCH₂ 7-F O S H1.80 Me H 3-CH₂Cl SCH₂ 7-F O S H1.81 Me H 3-CH₂Cl OCH₂ 5-Cl O S H1.83 Me H 3-CH₂Cl SCH₂ 5-Cl O S H1.84 Me H 3-CH₂Cl OCH₂ 6-Cl O S H1.85 Me H 3-CH₂Cl SCH₂ 6-Cl O S H1.86 Me H 3-CH₂Cl OCH₂ 4-CF₃ O S H1.87 Me H 3-CH₂Cl SCH₂ 4-CF₃ O S H1.88 Me H 3-CH₂Cl OCH₂ 5-CF₃ O S H1.89 Me H 3-CH₂Cl SCH₂ 5-CF₃ O S H1.90 Me H 3-CH₂Cl OCH₂ 6-CF₃ O S H1.91 Me H 3-CH₂Cl SCH₂ 6-CF₃ O S H1.92 Me H 3-CH₂Cl OCH₂ 7-CF₃ O S H1.93 Me H 3-CH₂Cl SCH₂ 7-CF₃ O S H1.94 Me H 3-CH₂Cl OCH₂ 5-OCF₃ O S H1.95 Me H 3-CH₂Cl SCH₂ 5-OCF₃ O S H1.96 Me H 3-CH₂Cl OCH₂ 6-OCF₃ O S H1.97 Me H 3-CH₂Cl SCH₂ 6-OCF₃ O S H2.1 Me H 2-CH₂Br OCH₂ 4-Me O S H2.2 Me H 2-CH₂Br SCH₂ 4-Me O S H2.3 Me H 2-CH₂Br OCH₂ 5-Me O S H2.4 Me H 2-CH₂Br SCH₂ 5-Me O S H2.5 Me H 2-CH₂Br OCH₂ 6-Me O S H2.6 Me H 2-CH₂Br SCH₂ 6-Me O S H2.7 Me H 2-CH₂Br OCH₂ 7-Me O S H2.8 Me H 2-CH₂Br SCH₂ 7-Me O S H2.9 Me H 2-CH₂Br OCH₂ 5-Et O S H2.10 Me H 2-CH₂Br SCH₂ 5-Et O S H2.11 Me H 2-CH₂Br OCH₂ 6-Et O S H2.12 Me H 2-CH₂Br SCH₂ 6-Et O S H2.13 Me H 2-CH₂Br OCH₂ 4-OMe O S H2.14 Me H 2-CH₂Br SCH₂ 4-OMe O S H2.15 Me H 2-CH₂Br OCH₂ 5-OMe O S H2.16 Me H 2-CH₂Br SCH₂ 5-OMe O S H2.17 Me H 2-CH₂Br OCH₂ 6-OMe O S H2.18 Me H 2-CH₂Br SCH₂ 6-OMe O S H2.19 Me H 2-CH₂Br OCH₂ 7-OMe O S H2.20 Me H 2-CH₂Br SCH₂ 7-OMe O S H2.21 Me H 2-CH₂Br OCH₂ 5-OEt O S H2.22 Me H 2-CH₂Br SCH₂ 5-OEt O S H2.23 Me H 2-CH₂Br OCH₂ 6-OEt O S H2.24 Me H 2-CH₂Br SCH₂ 6-OEt O S H2.25 Me H 2-CH₂Br OCH₂ 4-F O S H2.26 Me H 2-CH₂Br SCH₂ 4-F O S H2.27 Me H 2-CH₂Br OCH₂ 5-F O S H2.28 Me H 2-CH₂Br SCH₂ 5-F O S H2.29 Me H 2-CH₂Br OCH₂ 6-F O S H2.30 Me H 2-CH₂Br SCH₂ 6-F O S H2.31 Me H 2-CH₂Br OCH₂ 7-F O S H2.32 Me H 2-CH₂Br SCH₂ 7-F O S H2.33 Me H 2-CH₂Br OCH₂ 5-Cl O S H2.34 Me H 2-CH₂Br SCH₂ 5-Cl O S H2.35 Me H 2-CH₂Br OCH₂ 6-Cl O S H2.36 Me H 2-CH₂Br SCH₂ 6-Cl O S H2.37 Me H 2-CH₂Br OCH₂ 4-CF₃ O S H2.38 Me H 2-CH₂Br SCH₂ 4-CF₃ O S H2.39 Me H 2-CH₂Br OCH₂ 5-CF₃ O S H2.40 Me H 2-CH₂Br SCH₂ 5-CF₃ O S H2.41 Me H 2-CH₂Br OCH₂ 6-CF₃ O S H2.42 Me H 2-CH₂Br SCH₂ 6-CF₃ O S H2.43 Me H 2-CH₂Br OCH₂ 7-CF₃ O S H2.44 Me H 2-CH₂Br SCH₂ 7-CF₃ O S H2.45 Me H 2-CH₂Br OCH₂ 5-OCF₃ O S H2.46 Me H 2-CH₂Br SCH₂ 5-OCF₃ O S H2.47 Me H 2-CH₂Br OCH₂ 6-OCF₃ O S H2.48 Me H 2-CH₂Br SCH₂ 6-OCF₃ O S H2.49 Me H 3-CH₂Br OCH₂ 4-Me O S H2.50 Me H 3-CH₂Br SCH₂ 4-Me O S H2.51 Me H 3-CH₂Br OCH₂ 5-Me O S H2.52 Me H 3-CH₂Br SCH₂ 5-Me O S H2.53 Me H 3-CH₂Br OCH₂ 6-Me O S H2.54 Me H 3-CH₂Br SCH₂ 6-Me O S H2.55 Me H 3-CH₂Br OCH₂ 7-Me O S H2.56 Me H 3-CH₂Br SCH₂ 7-Me O S H2.57 Me H 3-CH₂Br OCH₂ 5-Et O S H2.58 Me H 3-CH₂Br SCH₂ 5-Et O S H2.59 Me H 3-CH₂Br OCH₂ 6-Et O S H2.60 Me H 3-CH₂Br SCH₂ 6-Et O S H2.61 Me H 3-CH₂Br OCH₂ 4-OMe O S H2.62 Me H 3-CH₂Br SCH₂ 4-OMe O S H2.63 Me H 3-CH₂Br OCH₂ 5-OMe O S H2.64 Me H 3-CH₂Br SCH₂ 5-OMe O S H2.65 Me H 3-CH₂Br OCH₂ 6-OMe O S H2.67 Me H 3-CH₂Br SCH₂ 6-OMe O S H2.68 Me H 3-CH₂Br OCH₂ 7-OMe O S H2.69 Me H 3-CH₂Br SCH₂ 7-OMe O S H2.70 Me H 3-CH₂Br OCH₂ 5-OEt O S H2.71 Me H 3-CH₂Br SCH₂ 5-OEt O S H2.72 Me H 3-CH₂Br OCH₂ 6-OEt O S H2.73 Me H 3-CH₂Br SCH₂ 6-OEt O S H2.74 Me H 3-CH₂Br OCH₂ 4-F O S H2.75 Me H 3-CH₂Br SCH₂ 4-F O S H2.76 Me H 3-CH₂Br OCH₂ 5-F O S H2.77 Me H 3-CH₂Br SCH₂ 5-F O S H2.78 Me H 3-CH₂Br OCH₂ 6-F O S H2.79 Me H 3-CH₂Br SCH₂ 6-F O S H2.80 Me H 3-CH₂Br OCH₂ 7-F O S H2.81 Me H 3-CH₂Br SCH₂ 7-F O S H2.82 Me H 3-CH₂Br OCH₂ 5-Cl O S H2.83 Me H 3-CH₂Br SCH₂ 5-Cl O S H2.84 Me H 3-CH₂Br OCH₂ 6-Cl O S H2.85 Me H 3-CH₂Br SCH₂ 6-Cl O S H2.86 Me H 3-CH₂Br OCH₂ 4-CF₃ O S H2.87 Me H 3-CH₂Br SCH₂ 4-CF₃ O S H2.88 Me H 3-CH₂Br OCH₂ 5-CF₃ O S H2.89 Me H 3-CH₂Br SCH₂ 5-CF₃ O S H2.90 Me H 3-CH₂Br OCH₂ 6-CF₃ O S H2.91 Me H 3-CH₂Br SCH₂ 6-CF₃ O S H2.92 Me H 3-CH₂Br OCH₂ 7-CF₃ O S H2.93 Me H 3-CH₂Br SCH₂ 7-CF₃ O S H2.94 Me H 3-CH₂Br OCH₂ 5-OCF₃ O S H2.95 Me H 3-CH₂Br SCH₂ 5-OCF₃ O S H2.96 Me H 3-CH₂Br OCH₂ 6-OCF₃ O S H2.97 Me H 3-CH₂Br SCH₂ 6-OCF₃ O S H3.1 Me H 2-F OCH₂ 4-Me O S H3.2 Me H 2-F SCH₂ 4-Me O S H3.3 MeO H 2-F OCH₂ 4-Me O S H3.4 Me H 2-F OCH₂ 5-Me O S H3.5 Me H 2-F SCH₂ 5-Me O S H3.6 MeO H 2-F OCH₂ 5-Me O S H3.7 MeO H 2-F OCH₂ 5-Me O O H3.8 Me H 2-F OCH₂ 6-Me O S H3.9 Me H 2-F SCH₂ 6-Me O S H3.10 MeO H 2-F OCH₂ 6-Me O S H3.11 MeO H 2-F OCH₂ 6-Me O O H3.12 Me H 2-F OCH₂ 7-Me O S H3.13 Me H 2-F SCH₂ 7-Me O S H3.14 MeO H 2-F OCH₂ 7-Me O S H3.15 Me H 2-F OCH₂ 5-Et O S H3.16 Me H 2-F SCH₂ 5-Et O S H3.17 MeO H 2-F OCH₂ 5-Et O S H3.18 MeO H 2-F SCH₂ 5-Et O S H3.19 Me H 2-F OCH₂ 6-Et O S H3.20 Me H 2-F SCH₂ 6-Et O S H3.21 MeO H 2-F OCH₂ 6-Et O S H3.22 MeO H 2-F SCH₂ 6-Et O S H3.23 Me H 2-F OCH₂ 4-F O S H3.24 Me H 2-F SCH₂ 4-F O S H3.25 MeO H 2-F OCH₂ 4-F O S H3.26 Me H 2-F OCH₂ 5-F O S H3.27 Me H 2-F SCH₂ 5-F O S H3.28 MeO H 2-F OCH₂ 5-F O S H3.29 MeO H 2-F SCH₂ 5-F O S H3.30 MeO H 2-F OCH₂ 5-F O O H3.31 MeO H 2-F SCH₂ 5-F O O H3.32 Me H 2-F OCH₂ 6-F O S H3.33 Me H 2-F SCH₂ 6-F O S H3.34 MeO H 2-F OCH₂ 6-F O S H3.35 MeO H 2-F OCH₂ 6-F O O H3.36 Me H 2-F OCH₂ 7-F O S H3.37 Me H 2-F SCH₂ 7-F O S H3.38 MeO H 2-F OCH₂ 7-F O S H3.39 MeO H 2-F OCH₂ 7-F O O H3.40 Me H 2-F OCH₂ 5-Cl O S H3.41 Me H 2-F SCH₂ 5-Cl O S H3.42 Me H 2-F OCH₂ 6-Cl O S H3.43 Me H 2-F SCH₂ 6-Cl O S H3.44 Me H 2-F OCH₂ 4-OMe O S H3.45 Me H 2-F SCH₂ 4-OMe O S H3.46 Me H 2-F OCH₂ 5-OMe O S H3.47 Me H 2-F SCH₂ 5-OMe O S H3.48 MeO H 2-F OCH₂ 5-OMe O S H3.49 Me H 2-F OCH₂ 6-OMe O S H3.50 Me H 2-F SCH₂ 6-OMe O S H3.51 MeO H 2-F OCH₂ 6-OMe O S H3.52 Me H 2-F OCH₂ 6-OMe O O H3.53 MeO H 2-F OCH₂ 6-OMe O O H3.54 Me H 2-F OCH₂ 7-OMe O S H3.55 Me H 2-F SCH₂ 7-OMe O S H3.56 Me H 2-F OCH₂ 5-OEt O S H3.57 Me H 2-F SCH₂ 5-OEt O S H3.58 Me H 2-F OCH₂ 6-OEt O S H3.59 Me H 2-F SCH₂ 6-OEt O S H3.60 Me H 2-F OCH₂ 4-CF₃ O S H3.61 Me H 2-F SCH₂ 4-CF₃ O S H3.62 Me H 2-F OCH₂ 5-CF₃ O S H3.63 Me H 2-F SCH₂ 5-CF₃ O S H3.64 MeO H 2-F OCH₂ 5-CF₃ O S H3.65 Me H 2-F OCH₂ 6-CF₃ O S H3.66 Me H 2-F SCH₂ 6-CF₃ O S H3.67 Me H 2-F OCH₂ 7-CF₃ O S H3.68 Me H 2-F SCH₂ 7-CF₃ O S H3.69 Me H 2-F OCH₂ 5-OCF₃ O S H3.70 Me H 2-F SCH₂ 5-OCF₃ O S H3.71 Me H 2-F OCH₂ 6-OCF₃ O S H3.72 Me H 2-F SCH₂ 6-OCF₃ O S H3.73 Me H 3-F OCH₂ 4-Me O S H3.74 Me H 3-F SCH₂ 4-Me O S H3.75 Me H 3-F OCH₂ 5-Me O S H3.76 Me H 3-F SCH₂ 5-Me O S H3.77 Me H 3-F OCH₂ 6-Me O S H3.78 Me H 3-F SCH₂ 6-Me O S H3.79 Me H 3-F OCH₂ 7-Me O S H3.80 Me H 3-F SCH₂ 7-Me O S H3.81 Me H 3-F OCH₂ 5-Et O S H3.82 Me H 3-F SCH₂ 5-Et O S H3.83 Me H 3-F OCH₂ 6-Et O S H3.84 Me H 3-F SCH₂ 6-Et O S H3.85 Me H 3-F OCH₂ 4-OMe O S H3.86 Me H 3-F SCH₂ 4-OMe O S H3.87 Me H 3-F OCH₂ 5-OMe O S H3.88 Me H 3-F SCH₂ 5-OMe O S H3.89 Me H 3-F OCH₂ 6-OMe O S H3.90 Me H 3-F SCH₂ 6-OMe O S H3.91 Me H 3-F OCH₂ 7-OMe O S H3.92 Me H 3-F SCH₂ 7-OMe O S H3.93 Me H 3-F OCH₂ 5-OEt O S H3.94 Me H 3-F SCH₂ 5-OEt O S H3.95 Me H 3-F OCH₂ 6-OEt O S H3.96 Me H 3-F SCH₂ 6-OEt O S H3.97 Me H 3-F OCH₂ 4-F O S H3.98 Me H 3-F SCH₂ 4-F O S H3.99 Me H 3-F OCH₂ 5-F O S H3.100 Me H 3-F SCH₂ 5-F O S H3.101 Me H 3-F OCH₂ 6-F O S H3.102 Me H 3-F SCH₂ 6-F O S H3.103 Me H 3-F OCH₂ 7-F O S H3.104 Me H 3-F SCH₂ 7-F O S H3.105 Me H 3-F OCH₂ 5-Cl O S H3.106 Me H 3-F SCH₂ 5-Cl O S H3.107 Me H 3-F OCH₂ 6-Cl O S H3.108 Me H 3-F SCH₂ 6-Cl O S H3.109 Me H 3-F OCH₂ 4-CF₃ O S H3.110 Me H 3-F SCH₂ 4-CF₃ O S H3.111 Me H 3-F OCH₂ 5-CF₃ O S H3.112 Me H 3-F SCH₂ 5-CF₃ O S H3.113 Me H 3-F OCH₂ 6-CF₃ O S H3.114 Me H 3-F SCH₂ 6-CF₃ O S H3.115 Me H 3-F OCH₂ 7-CF₃ O S H3.116 Me H 3-F SCH₂ 7-CF₃ O S H3.117 Me H 3-F OCH₂ 5-OCF₃ O S H3.118 Me H 3-F SCH₂ 5-OCF₃ O S H3.119 Me H 3-F OCH₂ 6-OCF₃ O S H3.120 Me H 3-F SCH₂ 6-OCF₃ O S H4.1 Me H 2-Cl OCH₂ 4-Me O S H4.3 Me H 2-Cl OCH₂ 5-Me O S 176-179 H4.4 Me H 2-Cl SCH₂ 5-Me O S H4.5 MeO H 2-Cl OCH₂ 5-Me O S H4.6 Me H 2-Cl OCH₂ 5-Me O O H4.7 MeO H 2-Cl OCH₂ 5-Me O O H4.8 Me H 2-Cl OCH₂ 6-Me O S 151-153 H4.9 Me H 2-Cl SCH₂ 6-Me O S H4.10 MeO H 2-Cl OCH₂ 6-Me O S H4.11 Me H 2-Cl OCH₂ 7-Me O S H4.12 Me H 2-Cl SCH₂ 7-Me O S H4.13 Me H 2-Cl OCH₂ 5-Et O S H4.14 Me H 2-Cl SCH₂ 5-Et O S H4.15 Me H 2-Cl OCH₂ 6-Et O S H4.16 Me H 2-Cl SCH₂ 6-Et O S H4.17 Me H 2-Cl OCH₂ 4-OMe O S H4.18 Me H 2-Cl SCH₂ 4-OMe O S H4.19 Me H 2-Cl OCH₂ 5-OMe O S 160-163 H4.20 Me H 2-Cl SCH₂ 5-OMe O S H4.21 MeO H 2-Cl OCH₂ 5-OMe O S H4.22 Me H 2-Cl OCH₂ 6-OMe O S 148-150 H4.23 Me H 2-Cl SCH₂ 6-OMe O S H4.24 MeO H 2-Cl OCH₂ 6-OMe O S H4.25 Me H 2-Cl OCH₂ 6-OMe O O H4.26 MeO H 2-Cl OCH₂ 6-OMe O O H4.27 Me H 2-Cl OCH₂ 7-OMe O S H4.28 Me H 2-Cl SCH₂ 7-OMe O S H4.29 Me H 2-Cl OCH₂ 5-OEt O S H4.30 Me H 2-Cl SCH₂ 5-OEt O S H4.31 Me H 2-Cl OCH₂ 6-OEt O S H4.32 Me H 2-Cl SCH₂ 6-OEt O S H4.33 Me H 2-Cl OCH₂ 4-F O S H4.34 Me H 2-Cl SCH₂ 4-F O S H4.35 Me H 2-Cl OCH₂ 5-F O S 160-167 H4.36 Me H 2-Cl SCH₂ 5-F O S H4.37 MeO H 2-Cl OCH₂ 5-F O S H4.38 Me H 2-Cl OCH₂ 6-F O S 174-176 H4.39 Me H 2-Cl SCH₂ 6-F O S H4.40 MeO H 2-Cl OCH₂ 6-F O S H4.41 Me H 2-Cl OCH₂ 7-F O S H4.42 Me H 2-Cl SCH₂ 7-F O S H4.43 Me H 2-Cl OCH₂ 5-Cl O S 192-193 H4.44 Me H 2-Cl SCH₂ 5-Cl O S H4.45 MeO H 2-Cl OCH₂ 5-Cl O S H4.46 Me H 2-Cl OCH₂ 6-Cl O S H4.47 Me H 2-Cl SCH₂ 6-Cl O S H4.48 Me H 2-Cl OCH₂ 4-CF₃ O S H4.49 Me H 2-Cl SCH₂ 4-CF₃ O S H4.50 Me H 2-Cl OCH₂ 5-CF₃ O S 183-184 H4.51 Me H 2-Cl SCH₂ 5-CF₃ O S H4.52 MeO H 2-Cl OCH₂ 5-CF₃ O S H4.53 Me H 2-Cl OCH₂ 6-CF₃ O S H4.54 Me H 2-Cl SCH₂ 6-CF₃ O S H4.55 Me H 2-Cl OCH₂ 7-CF₃ O S H4.56 Me H 2-Cl SCH₂ 7-CF₃ O S H4.57 Me H 2-Cl OCH₂ 5-OCF3 O S H4.58 Me H 2-Cl SCH₂ 5-OCF3 O S H4.59 Me H 2-Cl OCH₂ 6-OCF3 O S H4.60 Me H 2-Cl SCH₂ 6-OCF3 O S H4.61 Me H 2-Cl OCH₂ 4,5-Me₂ O S H4.62 Me H 2-Cl SCH₂ 4,5-Me₂ O S H4.63 Me H 2-Cl OCH₂ 4,6-Me₂ O S H4.64 Me H 2-Cl SCH₂ 4,6-Me₂ O S H4.65 Me H 2-Cl OCH₂ 4,7-Me₂ O S H4.66 Me H 2-Cl SCH₂ 4,7-Me₂ O S H4.67 Me H 2-Cl OCH₂ 5,6-Me₂ O S H4.68 Me H 2-Cl SCH₂ 5,6-Me₂ O S H4.69 Me H 2-Cl OCH₂ 5,7-Me₂ O S H4.70 Me H 2-Cl SCH₂ 5,7-Me₂ O S H4.71 Me H 2-Cl OCH₂ 6,7-Me₂ O S H4.72 Me H 2-Cl SCH₂ 6,7-Me₂ O S H4.73 Me H 2-Cl OCH₂ 4,5-(OMe)₂ O S H4.74 Me H 2-Cl SCH₂ 4,5-(OMe)₂ O S H4.75 Me H 2-Cl OCH₂ 4,6-(OMe)₂ O S H4.76 Me H 2-Cl SCH₂ 4,6-(OMe)₂ O S H4.77 Me H 2-Cl OCH₂ 4,7-(OMe)₂ O S H4.78 Me H 2-Cl SCH₂ 4,7-(OMe)₂ O S H4.79 Me H 2-Cl OCH₂ 5,6-(OMe)₂ O S H4.80 Me H 2-Cl SCH₂ 5,6-(OMe)₂ O S H4.81 Me H 2-Cl OCH₂ 5,7-(OMe)₂ O S H4.82 Me H 2-Cl SCH₂ 5,7-(OMe)₂ O S H4.83 Me H 2-Cl OCH₂ 6,7-(OMe)₂ O S H4.84 Me H 2-Cl SCH₂ 6,7-(OMe)₂ O S H4.85 Me H 2-Cl OCH₂ 4,5-F₂ O S H4.86 Me H 2-Cl SCH₂ 4,5-F₂ O S H4.87 Me H 2-Cl OCH₂ 4,6-F₂ O S H4.88 Me H 2-Cl SCH₂ 4,6-F₂ O S H4.89 Me H 2-Cl OCH₂ 4,7-F₂ O S H4.90 Me H 2-Cl SCH₂ 4,7-F₂ O S H4.91 Me H 2-Cl OCH₂ 5,6-F₂ O S 170-172 H4.92 Me H 2-Cl SCH₂ 5,6-F₂ O S H4.93 MeO H 2-Cl OCH₂ 5,6-F₂ O S H4.94 Me H 2-Cl OCH₂ 5,7-F₂ O S H4.95 Me H 2-Cl SCH₂ 5,7-F₂ O S H4.96 Me H 2-Cl OCH₂ 6,7-F₂ O S H4.97 Me H 2-Cl SCH₂ 6,7-F₂ O S H4.98 Me H 2-Cl OCH₂ 4,5-Cl₂ O S H4.99 Me H 2-Cl SCH₂ 4,5-Cl₂ O S H4.100 Me H 2-Cl OCH₂ 4,6-Cl₂ O S H4.101 Me H 2-Cl SCH₂ 4,6-Cl₂ O S H4.102 Me H 2-Cl OCH₂ 4,7-Cl₂ O S H4.103 Me H 2-Cl SCH₂ 4,7-Cl₂ O S H4.104 Me H 2-Cl OCH₂ 5,6-Cl₂ O S H4.105 Me H 2-Cl SCH₂ 5,6-Cl₂ O S H4.106 Me H 2-Cl OCH₂ 5,7-Cl₂ O S H4.107 Me H 2-Cl SCH₂ 5,7-Cl₂ O S H4.108 Me H 2-Cl OCH₂ 6,7-Cl₂ O S H4.109 Me H 2-Cl SCH₂ 6,7-Cl₂ O S H5.1 Me H 2-Cl OCH₂ 4,5-(CF₃)₂ O S H5.2 Me H 2-Cl SCH₂ 4,5-(CF₃)₂ O S H5.3 Me H 2-Cl OCH₂ 4,6-(CF₃)₂ O S H5.4 Me H 2-Cl SCH₂ 4,6-(CF₃)₂ O S H5.5 Me H 2-Cl OCH₂ 4,7-(CF₃)₂ O S H5.6 Me H 2-Cl SCH₂ 4,7-(CF₃)₂ O S H5.7 Me H 2-Cl OCH₂ 5,6-(CF₃)₂ O S H5.8 Me H 2-Cl SCH₂ 5,6-(CF₃)₂ O S H5.9 Me H 2-Cl OCH₂ 5,7-(CF₃)₂ O S H5.10 Me H 2-Cl SCH₂ 5,7-(CF₃)₂ O S H5.11 Me H 2-Cl OCH₂ 6,7-(CF₃)₂ O S H5.12 Me H 2-Cl SCH₂ 6,7-(CF₃)₂ O S H5.13 Me H 2-Cl OCH₂ 4-F,5-Me O S H5.14 Me H 2-Cl SCH₂ 4-F,5-Me O S H5.15 Me H 2-Cl OCH₂ 4-F,6-Me O S H5.16 Me H 2-Cl SCH₂ 4-F,6-Me O S H5.17 Me H 2-Cl OCH₂ 4-F,7-Me O S H5.18 Me H 2-Cl SCH₂ 4-F,7-Me O S H5.19 Me H 2-Cl OCH₂ 4-Me,5-F O S H5.20 Me H 2-Cl SCH₂ 4-Me,5-F O S H5.21 Me H 2-Cl OCH₂ 5-F,6-Me O S H5.22 Me H 2-Cl SCH₂ 5-F,6-Me O S H5.23 Me H 2-Cl OCH₂ 5-F,7-Me O S H5.24 Me H 2-Cl SCH₂ 5-F,7-Me O S H5.25 Me H 2-Cl OCH₂ 4-Me,6-F O S H5.26 Me H 2-Cl SCH₂ 4-Me,6-F O S H5.27 Me H 2-Cl OCH₂ 5-Me,6-F O S H5.28 Me H 2-Cl SCH₂ 5-Me,6-F O S H5.29 Me H 2-Cl OCH₂ 6-F,7-Me O S H5.30 Me H 2-Cl SCH₂ 6-F,7-Me O S H5.31 Me H 2-Cl OCH₂ 4-Me,7-F O S H5.32 Me H 2-Cl SCH₂ 4-Me,7-F O S H5.34 Me H 2-Cl OCH₂ 5-Me,7-F O S H5.35 Me H 2-Cl SCH₂ 5-Me,7-F O S H5.36 Me H 2-Cl OCH₂ 6-Me,7-F O S H5.37 Me H 2-Cl SCH₂ 6-Me,7-F O S H5.38 Me H 2-Cl OCH₂ 4-Cl,5-Me O S H5.39 Me H 2-Cl SCH₂ 4-Cl,5-Me O S H5.40 Me H 2-Cl OCH₂ 4-Cl,6-Me O S H5.41 Me H 2-Cl SCH₂ 4-Cl,6-Me O S H5.42 Me H 2-Cl OCH₂ 4-Cl,7-Me O S H5.43 Me H 2-Cl SCH₂ 4-Cl,7-Me O S H5.44 Me H 2-Cl OCH₂ 4-Me,5-Cl O S H5.45 Me H 2-Cl SCH₂ 4-Me,5-Cl O S H5.46 Me H 2-Cl OCH₂ 5-Cl,6-Me O S H5.47 Me H 2-Cl SCH₂ 5-Cl,6-Me O S H5.48 Me H 2-Cl OCH₂ 5-Cl,7-Me O S H5.49 Me H 2-Cl SCH₂ 5-Cl,7-Me O S H5.50 Me H 2-Cl OCH₂ 4-Me,6-Cl O S H5.51 Me H 2-Cl SCH₂ 4-Me,6-Cl O S H5.52 Me H 2-Cl OCH₂ 5-Me,6-Cl O S H5.53 Me H 2-Cl SCH₂ 5-Me,6-Cl O S H5.54 Me H 2-Cl OCH₂ 6-Cl,7-Me O S H5.56 Me H 2-Cl SCH₂ 6-Cl,7-Me O S H5.57 Me H 2-Cl OCH₂ 4-Me,7-Cl O S H5.58 Me H 2-Cl SCH₂ 4-Me,7-Cl O S H5.59 Me H 2-Cl OCH₂ 5-Me,7-Cl O S H5.60 Me H 2-Cl SCH₂ 5-Me,7-Cl O S H5.61 Me H 2-Cl OCH₂ 6-Me,7-Cl O S H5.62 Me H 2-Cl SCH₂ 6-Me,7-Cl O S H5.63 Me H 2-Cl OCH₂ 4-Cl,5-F O S H5.64 Me H 2-Cl SCH₂ 4-Cl,5-F O S H5.65 Me H 2-Cl OCH₂ 4-Cl,6-F O S H5.66 Me H 2-Cl SCH₂ 4-Cl,6-F O S H5.67 Me H 2-Cl OCH₂ 4-Cl,7-F O S H5.68 Me H 2-Cl SCH₂ 4-Cl,7-F O S H5.69 Me H 2-Cl OCH₂ 4-F,5-Cl O S H5.70 Me H 2-Cl SCH₂ 4-F,5-Cl O S H5.71 Me H 2-Cl OCH₂ 5-Cl,6-F O S H5.72 Me H 2-Cl SCH₂ 5-Cl,6-F O S H5.73 Me H 2-Cl OCH₂ 5-Cl,7-F O S H5.74 Me H 2-Cl SCH₂ 5-Cl,7-F O S H5.75 Me H 2-Cl OCH₂ 4-F,6-Cl O S H5.76 Me H 2-Cl SCH₂ 4-F,6-Cl O S H5.77 Me H 2-Cl OCH₂ 5-F,6-Cl O S H5.78 Me H 2-Cl SCH₂ 5-F,6-Cl O S H5.79 Me H 2-Cl OCH₂ 6-Cl,7-F O S H5.80 Me H 2-Cl SCH₂ 6-Cl,7-F O S H5.81 Me H 2-Cl OCH₂ 4-F,7-Cl O S H5.82 Me H 2-Cl SCH₂ 4-F,7-Cl O S H5.83 Me H 2-Cl OCH₂ 5-F,7-Cl O S H5.84 Me H 2-Cl SCH₂ 5-F,7-Cl O S H5.85 Me H 2-Cl OCH₂ 6-F,7-Cl O S H5.86 Me H 2-Cl SCH₂ 6-F,7-Cl O S H6.1 Me H 3-Cl OCH₂ 4-Me O S H6.2 Me H 3-Cl SOCH₂ 4-Me O S H6.3 Me H 3-Cl OCH₂ 5-Me O S H6.4 Me H 3-Cl SCH₂ 5-Me O S H6.5 Me H 3-Cl OCH₂ 6-Me O S H6.6 Me H 3-Cl SCH₂ 6-Me O S H6.7 Me H 3-Cl OCH₂ 7-Me O S H6.8 Me H 3-Cl SCH₂ 7-Me O S H6.9 Me H 3-Cl OCH₂ 5-Et O S H6.10 Me H 3-Cl SCH₂ 5-Et O S H6.11 Me H 3-Cl OCH₂ 6-Et O S H6.12 Me H 3-Cl SCH₂ 6-Et O S H6.13 Me H 3-Cl OCH₂ 4-OMe O S H6.14 Me H 3-Cl SCH₂ 4-OMe O S H6.15 Me H 3-Cl OCH₂ 5-OMe O S H6.16 Me H 3-Cl SCH₂ 5-OMe O S H6.17 Me H 3-Cl OCH₂ 6-OMe O S H6.18 Me H 3-Cl SCH₂ 6-OMe O S H6.19 Me H 3-Cl OCH₂ 7-OMe O S H6.20 Me H 3-Cl SCH₂ 7-OMe O S H6.21 Me H 3-Cl OCH₂ 5-OEt O S H6.22 Me H 3-Cl SCH₂ 5-OEt O S H6.23 Me H 3-Cl OCH₂ 6-OEt O S H6.24 Me H 3-Cl SCH₂ 6-OEt O S H6.25 Me H 3-Cl OCH₂ 4-F O S H6.26 Me H 3-Cl SCH₂ 4-F O S H6.27 Me H 3-Cl OCH₂ 5-F O S H6.28 Me H 3-Cl SCH₂ 5-F O S H6.29 Me H 3-Cl OCH₂ 6-F O S H6.30 Me H 3-Cl SCH₂ 6-F O S H6.31 Me H 3-Cl OCH₂ 7-F O S H6.32 Me H 3-Cl SCH₂ 7-F O S H6.33 Me H 3-Cl OCH₂ 5-Cl O S H6.34 Me H 3-Cl SCH₂ 5-Cl O S H6.35 Me H 3-Cl OCH₂ 6-Cl O S H6.36 Me H 3-Cl SCH₂ 6-Cl O S H6.37 Me H 3-Cl OCH₂ 4-CF₃ O S H6.38 Me H 3-Cl SCH₂ 4-CF₃ O S H6.39 Me H 3-Cl OCH₂ 5-CF₃ O S H6.40 Me H 3-Cl SCH₂ 5-CF₃ O S H6.41 Me H 3-Cl OCH₂ 6-CF₃ O S H6.42 Me H 3-Cl SCH₂ 6-CF₃ O S H6.43 Me H 3-Cl OCH₂ 7-CF₃ O S H6.44 Me H 3-Cl SCH₂ 7-CF₃ O S H6.45 Me H 3-Cl OCH₂ 5-OCF₃ O S H6.46 Me H 3-Cl SCH₂ 5-OCF₃ O S H6.47 Me H 3-Cl OCH₂ 6-OCF₃ O S H6.48 Me H 3-Cl SCH₂ 6-OCF₃ O S H7.1 Me H 2,3-Me₂ OCH₂ 4-Me O S H7.2 Me H 2,3-Me₂ SCH₂ 4-Me O S H7.3 MeO H 2,3-Me₂ OCH₂ 4-Me O S H7.4 Me H 2,3-Me₂ OCH₂ 5-Me O S 260-261 H7.5 Me H 2,3-Me₂ SCH₂ 5-Me O S H7.6 MeO H 2,3-Me₂ OCH₂ 5-Me O S H7.7 Me H 2,3-Me₂ OCH₂ 5-Me O O H7.8 MeO H 2,3-Me₂ OCH₂ 5-Me O O H7.9 Me H 2,3-Me₂ OCH₂ 6-Me O S 224-226 H7.10 Me H 2,3-Me₂ SCH₂ 6-Me O S H7.11 MeO H 2,3-Me₂ OCH₂ 6-Me O S H7.12 Me H 2,3-Me₂ OCH₂ 7-Me O S H7.13 Me H 2,3-Me₂ SCH₂ 7-Me O S H7.14 MeO H 2,3-Me₂ OCH₂ 7-Me O S H7.15 Me H 2,3-Me₂ OCH₂ 4-OMe O S H7.16 Me H 2,3-Me₂ SCH₂ 4-OMe O S H7.17 MeO H 2,3-Me₂ OCH₂ 4-OMe O S H7.18 Me H 2,3-Me₂ OCH₂ 5-OMe O S 224-225 H7.19 Me H 2,3-Me₂ SCH₂ 5-OMe O S H7.20 MeO H 2,3-Me₂ OCH₂ 5-OMe O S H7.21 Me H 2,3-Me₂ OCH₂ 6-OMe O S 229-232 H7.22 Me H 2,3-Me₂ SCH₂ 6-OMe O S H7.23 MeO H 2,3-Me₂ OCH₂ 6-OMe O S H7.24 Me H 2,3-Me₂ OCH₂ 6-OMe O O H7.25 MeO H 2,3-Me₂ OCH₂ 6-OMe O O H7.26 Me H 2,3-Me₂ OCH₂ 7-OMe O S H7.27 Me H 2,3-Me₂ SCH₂ 7-OMe O S H7.28 MeO H 2,3-Me₂ OCH₂ 7-OMe O S H7.29 Me H 2,3-Me₂ OCH₂ 5-OEt O S H7.30 Me H 2,3-Me₂ SCH₂ 5-OEt O S H7.31 Me H 2,3-Me₂ OCH₂ 6-OEt O S H7.32 Me H 2,3-Me₂ SCH₂ 6-OEt O S H7.33 Me H 2,3-Me₂ OCH₂ 4-F O S H7.34 Me H 2,3-Me₂ SCH₂ 4-F O S H7.35 MeO H 2,3-Me₂ OCH₂ 4-F O S H7.36 Me H 2,3-Me₂ OCH₂ 5-F O S 245-246 H7.37 Me H 2,3-Me₂ SCH₂ 5-F O S H7.38 MeO H 2,3-Me₂ OCH₂ 5-F O S H7.39 Me H 2,3-Me₂ OCH₂ 5-F O O H7.40 MeO H 2,3-Me₂ OCH₂ 5-F O O H7.41 Me H 2,3-Me₂ OCH₂ 6-F O S 245-247 H7.42 Me H 2,3-Me₂ SCH₂ 6-F O S H7.43 MeO H 2,3-Me₂ OCH₂ 6-F O S H7.44 Me H 2,3-Me₂ OCH₂ 6-F O O H7.45 MeO H 2,3-Me₂ OCH₂ 6-F O O H7.46 Me H 2,3-Me₂ OCH₂ 7-F O S H7.47 Me H 2,3-Me₂ SCH₂ 7-F O S H7.48 MeO H 2,3-Me₂ OCH₂ 7-F O S H7.49 Me H 2,3-Me₂ OCH₂ 5-Cl O S 246-250 H7.50 Me H 2,3-Me₂ SCH₂ 5-Cl O S H7.51 MeO H 2,3-Me₂ OCH₂ 5-Cl O S H7.52 Me H 2,3-Me₂ OCH₂ 6-Cl O S H7.53 Me H 2,3-Me₂ SCH₂ 6-Cl O S H7.54 MeO H 2,3-Me₂ OCH₂ 6-Cl O S H7.55 Me H 2,3-Me₂ OCH₂ 5-Et O S H7.56 Me H 2,3-Me₂ SCH₂ 5-Et O S H7.57 MeO H 2,3-Me₂ OCH₂ 5-Et O S H7.58 Me H 2,3-Me₂ OCH₂ 6-Et O S H7.59 Me H 2,3-Me₂ SCH₂ 6-Et O S H7.60 MeO H 2,3-Me₂ OCH₂ 6-Et O S H7.61 Me H 2,3-Me₂ OCH₂ 4-CF₃ O S H7.62 Me H 2,3-Me₂ SCH₂ 4-CF₃ O S H7.63 Me H 2,3-Me₂ OCH₂ 5-CF₃ O S 262-263 H7.64 Me H 2,3-Me₂ SCH₂ 5-CF₃ O S H7.65 MeO H 2,3-Me₂ OCH₂ 5-CF₃ O S H7.66 Me H 2,3-Me₂ OCH₂ 6-CF₃ O S H7.67 Me H 2,3-Me₂ SCH₂ 6-CF₃ O S H7.68 MeO H 2,3-Me₂ OCH₂ 6-CF₃ O S H7.69 Me H 2,3-Me₂ OCH₂ 7-CF₃ O S H7.70 Me H 2,3-Me₂ SCH₂ 7-CF₃ O S H7.71 Me H 2,3-Me₂ OCH₂ 5-OCF₃ O S H7.72 Me H 2,3-Me₂ SCH₂ 5-OCF₃ O S H7.73 Me H 2,3-Me₂ OCH₂ 6-OCF₃ O S H7.74 Me H 2,3-Me₂ SCH₂ 6-OCF₃ O S H7.75 Me H 2,3-Me₂ OCH₂ 4,5-Me₂ O S H7.76 Me H 2,3-Me₂ SCH₂ 4,5-Me₂ O S H7.77 MeO H 2,3-Me₂ OCH₂ 4,5-Me₂ O S H7.78 Me H 2,3-Me₂ OCH₂ 4,6-Me₂ O S H7.79 Me H 2,3-Me₂ SCH₂ 4,6-Me₂ O S H7.80 Me H 2,3-Me₂ OCH₂ 4,7-Me₂ O S H7.81 Me H 2,3-Me₂ SCH₂ 4,7-Me₂ O S H7.82 Me H 2,3-Me₂ OCH₂ 5,6-Me₂ O S H7.83 Me H 2,3-Me₂ SCH₂ 5,6-Me₂ O S H7.84 Me H 2,3-Me₂ OCH₂ 5,7-Me₂ O S H7.85 Me H 2,3-Me₂ SCH₂ 5,7-Me₂ O S H7.86 Me H 2,3-Me₂ OCH₂ 6,7-Me₂ O S H7.87 Me H 2,3-Me₂ SCH₂ 6,7-Me₂ O S H7.88 Me H 2,3-Me₂ OCH₂ 4,5-(OMe)₂ O S H7.89 Me H 2,3-Me₂ SCH₂ 4,5-(OMe)₂ O S H7.90 Me H 2,3-Me₂ OCH₂ 4,6-(OMe)₂ O S H7.91 Me H 2,3-Me₂ SCH₂ 4,6-(OMe)₂ O S H7.92 Me H 2,3-Me₂ OCH₂ 4,7-(OMe)₂ O S H7.93 Me H 2,3-Me₂ SCH₂ 4,7-(OMe)₂ O S H7.94 Me H 2,3-Me₂ OCH₂ 5,6-(OMe)₂ O S H7.95 Me H 2,3-Me₂ SCH₂ 5,6-(OMe)₂ O S H7.96 Me H 2,3-Me₂ OCH₂ 5,7-(OMe)₂ O S H7.97 Me H 2,3-Me₂ SCH₂ 5,7-(OMe)₂ O S H7.98 Me H 2,3-Me₂ OCH₂ 6,7-(OMe)₂ O S H7.99 Me H 2,3-Me₂ SCH₂ 6,7-(OMe)₂ O S H7.100 Me H 2,3-Me₂ OCH₂ 4,5-F₂ O S H7.101 Me H 2,3-Me₂ SCH₂ 4,5-F₂ O S H7.102 Me H 2,3-Me₂ OCH₂ 4,6-F₂ O S H7.103 Me H 2,3-Me₂ SCH₂ 4,6-F₂ O S H7.104 Me H 2,3-Me₂ OCH₂ 4,7-F₂ O S H7.105 Me H 2,3-Me₂ SCH₂ 4,7-F₂ O S H7.106 Me H 2,3-Me₂ OCH₂ 5,6-F₂ O S 248-249 H7.107 Me H 2,3-Me₂ SCH₂ 5,6-F₂ O S H7.108 MeO H 2,3-Me₂ OCH₂ 5,6-F₂ O S H7.109 Me H 2,3-Me₂ OCH₂ 5,7-F₂ O S H7.110 Me H 2,3-Me₂ SCH₂ 5,7-F₂ O S H7.111 Me H 2,3-Me₂ OCH₂ 6,7-F₂ O S H7.112 Me H 2,3-Me₂ SCH₂ 6,7-F₂ O S H8.1 Me H 2,3-Me₂ OCH₂ 4,5-Cl₂ O S H8.2 Me H 2,3-Me₂ SCH₂ 4,5-Cl₂ O S H8.3 Me H 2,3-Me₂ OCH₂ 4,6-Cl₂ O S H8.4 Me H 2,3-Me₂ SCH₂ 4,6-Cl₂ O S H8.5 Me H 2,3-Me₂ OCH₂ 4,7-Cl₂ O S H8.6 Me H 2,3-Me₂ SCH₂ 4,7-Cl₂ O S H8.7 Me H 2,3-Me₂ OCH₂ 5,6-Cl₂ O S H8.8 Me H 2,3-Me₂ SCH₂ 5,6-Cl₂ O S H8.9 MeO H 2,3-Me₂ OCH₂ 5,6-Cl₂ O S H8.10 Me H 2,3-Me₂ OCH₂ 5,7-Cl₂ O S H8.11 Me H 2,3-Me₂ SCH₂ 5,7-Cl₂ O S H8.12 Me H 2,3-Me₂ OCH₂ 6,7-Cl₂ O S H8.13 Me H 2,3-Me₂ SCH₂ 6,7-Cl₂ O S H8.14 Me H 2,3-Me₂ OCH₂ 4,5-(CF₃)₂ O S H8.15 Me H 2,3-Me₂ SCH₂ 4,5-(CF₃)₂ O S H8.16 Me H 2,3-Me₂ OCH₂ 4,6-(CF₃)₂ O S H8.17 Me H 2,3-Me₂ SCH₂ 4,6-(CF₃)₂ O S H8.18 Me H 2,3-Me₂ OCH₂ 4,7-(CF₃)₂ O S H8.19 Me H 2,3-Me₂ SCH₂ 4,7-(CF₃)₂ O S H8.20 Me H 2,3-Me₂ OCH₂ 5,6-(CF₃)₂ O S H8.21 Me H 2,3-Me₂ SCH₂ 5,6-(CF₃)₂ O S H8.22 Me H 2,3-Me₂ OCH₂ 5,7-(CF₃)₂ O S H8.23 Me H 2,3-Me₂ SCH₂ 5,7-(CF₃)₂ O S H8.24 Me H 2,3-Me₂ OCH₂ 6,7-(CF₃)₂ O S H8.25 Me H 2,3-Me₂ SCH₂ 6,7-(CF₃)₂ O S H8.26 Me H 2,3-Me₂ OCH₂ 4-F,5-Me O S H8.27 Me H 2,3-Me₂ SCH₂ 4-F,5-Me O S H8.28 Me H 2,3-Me₂ OCH₂ 4-F,6-Me O S H8.29 Me H 2,3-Me₂ SCH₂ 4-F,6-Me O S H8.30 MeO H 2,3-Me₂ OCH₂ 4-F,6-Me O S H8.31 Me H 2,3-Me₂ OCH₂ 4-F,7-Me O S H8.32 Me H 2,3-Me₂ SCH₂ 4-F,7-Me O S H8.33 Me H 2,3-Me₂ OCH₂ 4-Me,5-F O S H8.34 Me H 2,3-Me₂ SCH₂ 4-Me,5-F O S H8.35 Me H 2,3-Me₂ OCH₂ 5-F,6-Me O S H8.36 Me H 2,3-Me₂ SCH₂ 5-F,6-Me O S H8.37 Me H 2,3-Me₂ OCH₂ 5-F,7-Me O S H8.38 Me H 2,3-Me₂ SCH₂ 5-F,7-Me O S H8.39 Me H 2,3-Me₂ OCH₂ 4-Me,6-F O S H8.40 Me H 2,3-Me₂ SCH₂ 4-Me,6-F O S H8.41 Me H 2,3-Me₂ OCH₂ 5-Me,6-F O S H8.42 Me H 2,3-Me₂ SCH₂ 5-Me,6-F O S H8.43 Me H 2,3-Me₂ OCH₂ 6-F,7-Me O S H8.44 Me H 2,3-Me₂ SCH₂ 6-F,7-Me O S H8.45 Me H 2,3-Me₂ OCH₂ 4-Me,7-F O S H8.46 Me H 2,3-Me₂ SCH₂ 4-Me,7-F O S H8.47 Me H 2,3-Me₂ OCH₂ 5-Me,7-F O S H8.48 Me H 2,3-Me₂ SCH₂ 5-Me,7-F O S H8.49 Me H 2,3-Me₂ OCH₂ 6-Me,7-F O S H8.50 Me H 2,3-Me₂ SCH₂ 6-Me,7-F O S H8.51 Me H 2,3-Me₂ OCH₂ 4-Cl,5-Me O S H8.52 Me H 2,3-Me₂ SCH₂ 4-Cl,5-Me O S H8.53 Me H 2,3-Me₂ OCH₂ 4-Cl,6-Me O S H8.54 Me H 2,3-Me₂ SCH₂ 4-Cl,6-Me O S H8.55 MeO H 2,3-Me₂ OCH₂ 4-Cl,6-Me O S H8.56 Me H 2,3-Me₂ OCH₂ 4-Cl,7-Me O S H8.57 Me H 2,3-Me₂ SCH₂ 4-Cl,7-Me O S H8.58 Me H 2,3-Me₂ OCH₂ 4-Me,5-Cl O S H8.59 Me H 2,3-Me₂ SCH₂ 4-Me,5-Cl O S H8.60 Me H 2,3-Me₂ OCH₂ 5-Cl,6-Me O S H8.61 Me H 2,3-Me₂ SCH₂ 5-Cl,6-Me O S H8.62 Me H 2,3-Me₂ OCH₂ 5-Cl,7-Me O S H8.63 Me H 2,3-Me₂ SCH₂ 5-Cl,7-Me O S H8.64 Me H 2,3-Me₂ OCH₂ 4-Me,6-Cl O S H8.65 Me H 2,3-Me₂ SCH₂ 4-Me,6-Cl O S H8.66 Me H 2,3-Me₂ OCH₂ 5-Me,6-Cl O S H8.67 Me H 2,3-Me₂ SCH₂ 5-Me,6-Cl O S H8.68 Me H 2,3-Me₂ OCH₂ 6-Cl,7-Me O S H8.69 Me H 2,3-Me₂ SCH₂ 6-Cl,7-Me O S H8.70 Me H 2,3-Me₂ OCH₂ 4-Me,7-Cl O S H8.71 Me H 2,3-Me₂ SCH₂ 4-Me,7-Cl O S H8.72 Me H 2,3-Me₂ OCH₂ 5-Me,7-Cl O S H8.73 Me H 2,3-Me₂ SCH₂ 5-Me,7-Cl O S H8.74 Me H 2,3-Me₂ OCH₂ 6-Me,7-Cl O S H8.75 Me H 2,3-Me₂ SCH₂ 6-Me,7-Cl O S H8.76 Me H 2,3-Me₂ OCH₂ 4-Cl,5-F O S H8.77 Me H 2,3-Me₂ SCH₂ 4-Cl,5-F O S H8.78 MeO H 2,3-Me₂ OCH₂ 4-Cl,5-F O S H8.79 Me H 2,3-Me₂ OCH₂ 4-Cl,6-F O S H8.80 Me H 2,3-Me₂ SCH₂ 4-Cl,6-F O S H8.81 Me H 2,3-Me₂ OCH₂ 4-Cl,7-F O S H8.82 Me H 2,3-Me₂ SCH₂ 4-Cl,7-F O S H8.83 Me H 2,3-Me₂ OCH₂ 4-F,5-Cl O S H8.84 Me H 2,3-Me₂ SCH₂ 4-F,5-Cl O S H8.85 Me H 2,3-Me₂ OCH₂ 5-Cl,6-F O S H8.86 Me H 2,3-Me₂ SCH₂ 5-Cl,6-F O S H8.87 Me H 2,3-Me₂ OCH₂ 5-Cl,7-F O S H8.88 Me H 2,3-Me₂ SCH₂ 5-Cl,7-F O S H8.89 Me H 2,3-Me₂ OCH₂ 4-F,6-Cl O S H8.90 Me H 2,3-Me₂ SCH₂ 4-F,6-Cl O S H8.91 Me H 2,3-Me₂ OCH₂ 5-F,6-Cl O S H8.92 Me H 2,3-Me₂ SCH₂ 5-F,6-Cl O S H8.93 Me H 2,3-Me₂ OCH₂ 6-Cl,7-F O S H8.94 Me H 2,3-Me₂ SCH₂ 6-Cl,7-F O S H8.95 Me H 2,3-Me₂ OCH₂ 4-F,7-Cl O S H8.96 Me H 2,3-Me₂ SCH₂ 4-F,7-Cl O S H8.97 Me H 2,3-Me₂ OCH₂ 5-F,7-Cl O S H8.98 Me H 2,3-Me₂ SCH₂ 5-F,7-Cl O S H8.99 Me H 2,3-Me₂ OCH₂ 6-F,7-Cl O S H8.100 Me H 2,3-Me₂ SCH₂ 6-F,7-Cl O S H8.101 MeO H 2,5-Me₂ OCH₂ 5-F O S H8.102 MeO H 2,5-Me₂ OCH₂ 5-F O O H8.103 MeO H 2,6-Me₂ OCH₂ 5-F O S H8.104 MeO H 2,6-Me₂ OCH₂ 5-F O O H8.105 MeO H 3,5-Me₂ OCH₂ 5-F O S H8.106 MeO H 3,5-Me₂ OCH₂ 5-F O O H9.1 Me H 2,3-F₂ OCH₂ 4-Me O S H9.2 Me H 2,3-F₂ SCH₂ 4-Me O S H9.3 Me H 2,3-F₂ OCH₂ 5-Me O S H9.4 Me H 2,3-F₂ SCH₂ 5-Me O S H9.5 Me H 2,3-F₂ OCH₂ 6-Me O S H9.6 Me H 2,3-F₂ SCH₂ 6-Me O S H9.7 Me H 2,3-F₂ OCH₂ 7-Me O S H9.8 Me H 2,3-F₂ SCH₂ 7-Me O S H9.10 Me H 2,3-F₂ OCH₂ 5-Et O S H9.11 Me H 2,3-F₂ SCH₂ 5-Et O S H9.12 Me H 2,3-F₂ OCH₂ 6-Et O S H9.13 Me H 2,3-F₂ SCH₂ 6-Et O S H9.14 Me H 2,3-F₂ OCH₂ 4-OMe O S H9.15 Me H 2,3-F₂ SCH₂ 4-OMe O S H9.16 Me H 2,3-F₂ OCH₂ 5-OMe O S H9.17 Me H 2,3-F₂ SCH₂ 5-OMe O S H9.18 Me H 2,3-F₂ OCH₂ 6-OMe O S H9.19 Me H 2,3-F₂ SCH₂ 6-OMe O S H9.20 Me H 2,3-F₂ OCH₂ 7-OMe O S H9.21 Me H 2,3-F₂ SCH₂ 7-OMe O S H9.22 Me H 2,3-F₂ OCH₂ 5-OEt O S H9.23 Me H 2,3-F₂ SCH₂ 5-OEt O S H9.24 Me H 2,3-F₂ OCH₂ 6-OEt O S H9.25 Me H 2,3-F₂ SCH₂ 6-OEt O S H9.26 Me H 2,3-F₂ OCH₂ 4-F O S H9.27 Me H 2,3-F₂ SCH₂ 4-F O S H9.28 Me H 2,3-F₂ OCH₂ 5-F O S H9.29 Me H 2,3-F₂ SCH₂ 5-F O S H9.30 Me H 2,3-F₂ OCH₂ 6-F O S H9.31 Me H 2,3-F₂ SCH₂ 6-F O S H9.32 Me H 2,3-F₂ OCH₂ 7-F O S H9.34 Me H 2,3-F₂ SCH₂ 7-F O S H9.35 Me H 2,3-F₂ OCH₂ 5-Cl O S H9.36 Me H 2,3-F₂ SCH₂ 5-Cl O S H9.37 Me H 2,3-F₂ OCH₂ 6-Cl O S H9.38 Me H 2,3-F₂ SCH₂ 6-Cl O S H9.39 Me H 2,3-F₂ OCH₂ 4-CF₃ O S H9.40 Me H 2,3-F₂ SCH₂ 4-CF₃ O S H9.41 Me H 2,3-F₂ OCH₂ 5-CF₃ O S H9.42 Me H 2,3-F₂ SCH₂ 5-CF₃ O S H9.43 Me H 2,3-F₂ OCH₂ 6-CF₃ O S H9.44 Me H 2,3-F₂ SCH₂ 6-CF₃ O S H9.45 Me H 2,3-F₂ OCH₂ 7-CF₃ O S H9.46 Me H 2,3-F₂ SCH₂ 7-CF₃ O S H9.47 Me H 2,3-F₂ OCH₂ 5-OCF₃ O S H9.48 Me H 2,3-F₂ SCH₂ 5-OCF₃ O S H9.49 Me H 2,3-F₂ OCH₂ 6-OCF₃ O S H9.50 Me H 2,3-F₂ SCH₂ 6-OCF₃ O S H9.51 Me H 2,3-F₂ OCH₂ 4,5-Me₂ O S H9.52 Me H 2,3-F₂ SCH₂ 4,5-Me₂ O S H9.53 Me H 2,3-F₂ OCH₂ 4,6-Me₂ O S H9.54 Me H 2,3-F₂ SCH₂ 4,6-Me₂ O S H9.55 Me H 2,3-F₂ OCH₂ 4,7-Me₂ O S H9.56 Me H 2,3-F₂ SCH₂ 4,7-Me₂ O S H9.57 Me H 2,3-F₂ OCH₂ 5,6-Me₂ O S H9.58 Me H 2,3-F₂ SCH₂ 5,6-Me₂ O S H9.60 Me H 2,3-F₂ OCH₂ 5,7-Me₂ O S H9.61 Me H 2,3-F₂ SCH₂ 5,7-Me₂ O S H9.62 Me H 2,3-F₂ OCH₂ 6,7-Me₂ O S H9.63 Me H 2,3-F₂ SCH₂ 6,7-Me₂ O S H9.64 Me H 2,3-F₂ OCH₂ 4,5-(OMe)₂ O S H9.65 Me H 2,3-F₂ SCH₂ 4,5-(OMe)₂ O S H9.66 Me H 2,3-F₂ OCH₂ 4,6-(OMe)₂ O S H9.67 Me H 2,3-F₂ SCH₂ 4,6-(OMe)₂ O S H9.68 Me H 2,3-F₂ OCH₂ 4,7-(OMe)₂ O S H9.69 Me H 2,3-F₂ SCH₂ 4,7-(OMe)₂ O S H9.70 Me H 2,3-F₂ OCH₂ 5,6-(OMe)₂ O S H9.71 Me H 2,3-F₂ SCH₂ 5,6-(OMe)₂ O S H9.72 Me H 2,3-F₂ OCH₂ 5,7-(OMe)₂ O S H9.73 Me H 2,3-F₂ SCH₂ 5,7-(OMe)₂ O S H9.74 Me H 2,3-F₂ OCH₂ 6,7-(OMe)₂ O S H9.75 Me H 2,3-F₂ SCH₂ 6,7-(OMe)₂ O S H9.76 Me H 2,3-F₂ OCH₂ 4,5-F₂ O S H9.77 Me H 2,3-F₂ SCH₂ 4,5-F₂ O S H9.78 Me H 2,3-F₂ OCH₂ 4,6-F₂ O S H9.79 Me H 2,3-F₂ SCH₂ 4,6-F₂ O S H9.80 Me H 2,3-F₂ OCH₂ 4,7-F₂ O S H9.81 Me H 2,3-F₂ SCH₂ 4,7-F₂ O S H9.82 Me H 2,3-F₂ OCH₂ 5,6-F₂ O S H9.83 Me H 2,3-F₂ SCH₂ 5,6-F₂ O S H9.84 Me H 2,3-F₂ OCH₂ 5,7-F₂ O S H9.85 Me H 2,3-F₂ SCH₂ 5,7-F₂ O S H9.86 Me H 2,3-F₂ OCH₂ 6,7-F₂ O S H9.87 Me H 2,3-F₂ SCH₂ 6,7-F₂ O S H9.88 Me H 2,3-F₂ OCH₂ 4,5-Cl₂ O S H9.89 Me H 2,3-F₂ SCH₂ 4,5-Cl₂ O S H9.90 Me H 2,3-F₂ OCH₂ 4,6-Cl₂ O S H9.91 Me H 2,3-F₂ SCH₂ 4,6-Cl₂ O S H9.92 Me H 2,3-F₂ OCH₂ 4,7-Cl₂ O S H9.93 Me H 2,3-F₂ SCH₂ 4,7-Cl₂ O S H9.94 Me H 2,3-F₂ OCH₂ 5,6-Cl₂ O S H9.95 Me H 2,3-F₂ SCH₂ 5,6-Cl₂ O S H9.96 Me H 2,3-F₂ OCH₂ 5,7-Cl₂ O S H9.97 Me H 2,3-F₂ SCH₂ 5,7-Cl₂ O S H9.98 Me H 2,3-F₂ OCH₂ 6,7-Cl₂ O S H9.99 Me H 2,3-F₂ SCH₂ 6,7-Cl₂ O S H9.100 Me H 2,3-F₂ OCH₂ 4,5-(CF₃)₂ O S H9.101 Me H 2,3-F₂ SCH₂ 4,5-(CF₃)₂ O S H9.102 Me H 2,3-F₂ OCH₂ 4,6-(CF₃)₂ O S H9.103 Me H 2,3-F₂ SCH₂ 4,6-(CF₃)₂ O S H9.104 Me H 2,3-F₂ OCH₂ 4,7-(CF₃)₂ O S H9.105 Me H 2,3-F₂ SCH₂ 4,7-(CF₃)₂ O S H9.106 Me H 2,3-F₂ OCH₂ 5,6-(CF₃)₂ O S H9.107 Me H 2,3-F₂ SCH₂ 5,6-(CF₃)₂ O S H9.108 Me H 2,3-F₂ OCH₂ 5,7-(CF₃)₂ O S H9.109 Me H 2,3-F₂ SCH₂ 5,7-(CF₃)₂ O S H9.110 Me H 2,3-F₂ OCH₂ 6,7-(CF₃)₂ O S H9.111 Me H 2,3-F₂ SCH₂ 6,7-(CF₃)₂ O S H10.1 Me H 2,3-F₂ OCH₂ 4-F,5-Me O S H10.2 Me H 2,3-F₂ SCH₂ 4-F,5-Me O S H10.3 Me H 2,3-F₂ OCH₂ 4-F,6-Me O S H10.4 Me H 2,3-F₂ SCH₂ 4-F,6-Me O S H10.5 Me H 2,3-F₂ OCH₂ 4-F,7-Me O S H10.6 Me H 2,3-F₂ SCH₂ 4-F,7-Me O S H10.7 Me H 2,3-F₂ OCH₂ 4-Me,5-F O S H10.8 Me H 2,3-F₂ SCH₂ 4-Me,5-F O S H10.9 Me H 2,3-F₂ OCH₂ 5-F,6-Me O S H10.10 Me H 2,3-F₂ SCH₂ 5-F,6-Me O S H10.11 Me H 2,3-F₂ OCH₂ 5-F,7-Me O S H10.12 Me H 2,3-F₂ SCH₂ 5-F,7-Me O S H10.13 Me H 2,3-F₂ OCH₂ 4-Me,6-F O S H10.14 Me H 2,3-F₂ SCH₂ 4-Me,6-F O S H10.15 Me H 2,3-F₂ OCH₂ 5-Me,6-F O S H10.16 Me H 2,3-F₂ SCH₂ 5-Me,6-F O S H10.17 Me H 2,3-F₂ OCH₂ 6-F,7-Me O S H10.18 Me H 2,3-F₂ SCH₂ 6-F,7-Me O S H10.19 Me H 2,3-F₂ OCH₂ 4-Me,7-F O S H10.20 Me H 2,3-F₂ SCH₂ 4-Me,7-F O S H10.21 Me H 2,3-F₂ OCH₂ 5-Me,7-F O S H10.22 Me H 2,3-F₂ SCH₂ 5-Me,7-F O S H10.23 Me H 2,3-F₂ OCH₂ 6-Me,7-F O S H10.24 Me H 2,3-F₂ SCH₂ 6-Me,7-F O S H10.25 Me H 2,3-F₂ OCH₂ 4-Cl,5-Me O S H10.26 Me H 2,3-F₂ SCH₂ 4-Cl,5-Me O S H10.27 Me H 2,3-F₂ OCH₂ 4-Cl,6-Me O S H10.28 Me H 2,3-F₂ SCH₂ 4-Cl,6-Me O S H10.29 Me H 2,3-F₂ OCH₂ 4-Cl,7-Me O S H10.30 Me H 2,3-F₂ SCH₂ 4-Cl,7-Me O S H10.31 Me H 2,3-F₂ OCH₂ 4-Me,5-Cl O S H10.32 Me H 2,3-F₂ SCH₂ 4-Me,5-Cl O S H10.33 Me H 2,3-F₂ OCH₂ 5-Cl,6-Me O S H10.34 Me H 2,3-F₂ SCH₂ 5-Cl,6-Me O S H10.35 Me H 2,3-F₂ OCH₂ 5-Cl,7-Me O S H10.36 Me H 2,3-F₂ SCH₂ 5-Cl,7-Me O S H10.37 Me H 2,3-F₂ OCH₂ 4-Me,6-Cl O S H10.38 Me H 2,3-F₂ SCH₂ 4-Me,6-Cl O S H10.39 Me H 2,3-F₂ OCH₂ 6-Cl,5-Me O S H10.40 Me H 2,3-F₂ SCH₂ 6-Cl,5-Me O S H10.41 Me H 2,3-F₂ OCH₂ 6-Cl,7-Me O S H10.42 Me H 2,3-F₂ SCH₂ 6-Cl,7-Me O S H10.43 Me H 2,3-F₂ OCH₂ 4-Me,7-Cl O S H10.44 Me H 2,3-F₂ SCH₂ 4-Me,7-Cl O S H10.45 Me H 2,3-F₂ OCH₂ 5-Me,7-Cl O S H10.46 Me H 2,3-F₂ SCH₂ 5-Me,7-Cl O S H10.47 Me H 2,3-F₂ OCH₂ 6-Me,7-Cl O S H10.48 Me H 2,3-F₂ SCH₂ 6-Me,7-Cl O S H10.49 Me H 2,3-F₂ OCH₂ 4-Cl,5-F O S H10.50 Me H 2,3-F₂ SCH₂ 4-Cl,5-F O S H10.51 Me H 2,3-F₂ OCH₂ 4-Cl,6-F O S H10.52 Me H 2,3-F₂ SCH₂ 4-Cl,6-F O S H10.53 Me H 2,3-F₂ OCH₂ 4-Cl,7-F O S H10.54 Me H 2,3-F₂ SCH₂ 4-Cl,7-F O S H10.55 Me H 2,3-F₂ OCH₂ 4-F,5-Cl O S H10.56 Me H 2,3-F₂ SCH₂ 4-F,5-Cl O S H10.57 Me H 2,3-F₂ OCH₂ 5-Cl,6-F O S H10.58 Me H 2,3-F₂ SCH₂ 5-Cl,6-F O S H10.59 Me H 2,3-F₂ OCH₂ 5-Cl,7-F O S H10.60 Me H 2,3-F₂ SCH₂ 5-Cl,7-F O S H10.61 Me H 2,3-F₂ OCH₂ 4-F,6-Cl O S H10.62 Me H 2,3-F₂ SCH₂ 4-F,6-Cl O S H10.63 Me H 2,3-F₂ OCH₂ 5-F,6-Cl O S H10.64 Me H 2,3-F₂ SCH₂ 5-F,6-Cl O S H10.65 Me H 2,3-F₂ OCH₂ 7-F,6-Cl O S H10.66 Me H 2,3-F₂ SCH₂ 7-F,6-Cl O S H10.67 Me H 2,3-F₂ OCH₂ 4-F,7-Cl O S H10.68 Me H 2,3-F₂ SCH₂ 4-F,7-Cl O S H10.69 Me H 2,3-F₂ OCH₂ 5-F,7-Cl O S H10.70 Me H 2,3-F₂ SCH₂ 5-F,7-Cl O S H10.71 Me H 2,3-F₂ OCH₂ 6-F,7-Cl O S H10.72 Me H 2,3-F₂ SCH₂ 6-F,7-Cl O S H11.1 Me H 2,3-(OMe)₂ OCH₂ 4-Me O S H11.2 Me H 2,3-(OMe)₂ SCH₂ 4-Me O S H11.3 Me H 2,3-(OMe)₂ OCH₂ 5-Me O S H11.4 Me H 2,3-(OMe)₂ SCH₂ 5-Me O S H11.5 Me H 2,3-(OMe)₂ OCH₂ 6-Me O S H11.6 Me H 2,3-(OMe)₂ SCH₂ 6-Me O S H11.7 Me H 2,3-(OMe)₂ OCH₂ 7-Me O S H11.8 Me H 2,3-(OMe)₂ SCH₂ 7-Me O S H11.9 Me H 2,3-(OMe)₂ OCH₂ 5-Et O S H11.10 Me H 2,3-(OMe)₂ SCH₂ 5-Et O S H11.11 Me H 2,3-(OMe)₂ OCH₂ 6-Et O S H11.12 Me H 2,3-(OMe)₂ SCH₂ 6-Et O S H11.13 Me H 2,3-(OMe)₂ OCH₂ 4-OMe O S H11.14 Me H 2,3-(OMe)₂ SCH₂ 4-OMe O S H11.15 Me H 2,3-(OMe)₂ OCH₂ 5-OMe O S H11.16 Me H 2,3-(OMe)₂ SCH₂ 5-OMe O S H11.17 Me H 2,3-(OMe)₂ OCH₂ 6-OMe O S H11.18 Me H 2,3-(OMe)₂ SCH₂ 6-OMe O S H11.19 Me H 2,3-(OMe)₂ OCH₂ 7-OMe O S H11.20 Me H 2,3-(OMe)₂ SCH₂ 7-OMe O S H11.21 Me H 2,3-(OMe)₂ OCH₂ 5-OEt O S H11.22 Me H 2,3-(OMe)₂ SCH₂ 5-OEt O S H11.23 Me H 2,3-(OMe)₂ OCH₂ 6-OEt O S H11.24 Me H 2,3-(OMe)₂ SCH₂ 6-OEt O S H11.25 Me H 2,3-(OMe)₂ OCH₂ 4-F O S H11.26 Me H 2,3-(OMe)₂ SCH₂ 4-F O S H11.27 Me H 2,3-(OMe)₂ OCH₂ 5-F O S H11.28 Me H 2,3-(OMe)₂ SCH₂ 5-F O S H11.29 Me H 2,3-(OMe)₂ OCH₂ 6-F O S H11.31 Me H 2,3-(OMe)₂ OCH₂ 7-F O S H11.32 Me H 2,3-(OMe)₂ SCH₂ 7-F O S H11.33 Me H 2,3-(OMe)₂ OCH₂ 5-Cl O S H11.34 Me H 2,3-(OMe)₂ SCH₂ 5-Cl O S H11.35 Me H 2,3-(OMe)₂ OCH₂ 6-Cl O S H11.36 Me H 2,3-(OMe)₂ SCH₂ 6-Cl O S H11.37 Me H 2,3-(OMe)₂ OCH₂ 4-CF₃ O S H11.38 Me H 2,3-(OMe)₂ SCH₂ 4-CF₃ O S H11.39 Me H 2,3-(OMe)₂ OCH₂ 5-CF₃ O S H11.40 Me H 2,3-(OMe)₂ SCH₂ 5-CF₃ O S H11.41 Me H 2,3-(OMe)₂ OCH₂ 6-CF₃ O S H11.42 Me H 2,3-(OMe)₂ SCH₂ 6-CF₃ O S H11.43 Me H 2,3-(OMe)₂ OCH₂ 7-CF₃ O S H11.44 Me H 2,3-(OMe)₂ SCH₂ 7-CF₃ O S H11.45 Me H 2,3-(OMe)₂ OCH₂ 5-OCF₃ O S H11.46 Me H 2,3-(OMe)₂ SCH₂ 5-OCF₃ O S H11.47 Me H 2,3-(OMe)₂ OCH₂ 6-OCF₃ O S H11.48 Me H 2,3-(OMe)₂ SCH₂ 6-OCF₃ O S H11.49 MeO H 2,3-Cl₂ OCH₂ 5-F O S H11.50 MeO H 2,5-Cl₂ OCH₂ 5-F O S H11.51 MeO H 2,6-Cl₂ OCH₂ 5-F O S H11.52 MeO H 3,5-Cl₂ OCH₂ 5-F O S ──────────────────────────────────── 上記の例示化合物中、好適なものとしては、Ａ１．１、
Ａ１．２、Ａ１．３、Ａ１．５、Ａ１．６、Ａ１．７、
Ａ１．８、Ａ１．９、Ａ１．１３、Ａ１．１６、Ａ１．
１８、Ａ１．２１、Ａ１．２５、Ａ１．２８、Ａ１．３
１、Ａ１．３２、Ａ１．４５、Ａ１．５６、Ａ１．５
８、Ａ１．６０、Ａ１．６２、Ａ１．６５、Ａ１．７
０、Ｂ１．１、Ｂ１．３、Ｂ１．５、Ｂ１．１０、Ｂ
２．３７、Ｂ２．６３、Ｃ１．１、Ｃ１．２、Ｃ１．
３、Ｃ１．５、Ｃ１．６、Ｃ１．１１、Ｃ１．１３、Ｃ
１．１７、Ｃ１．１９、Ｃ１．２３、Ｃ１．２４、Ｃ
１．２７、Ｃ１．２８、Ｃ１．３６、Ｃ１．４２、Ｃ
１．４４、Ｃ１．５２、Ｃ１．５５、Ｃ２．１、Ｃ２．
４、Ｃ２．１９、Ｃ３．３０、Ｃ３．３２、Ｃ４．２
７、Ｃ４．２９、Ｃ６．１、Ｃ６．２９、Ｃ７．５５、
Ｃ８．１、Ｃ８．２、Ｃ８．３、Ｃ８．６、Ｃ８．１
９、Ｃ８．２０、Ｃ８．２２、Ｃ８．２３、Ｃ８．３
９、Ｃ８．７２、Ｃ８．７６、Ｃ９．１、Ｃ９．３、Ｃ
９．４、Ｃ９．６、Ｃ９．２０、Ｃ９．２２、Ｃ９．２
３、Ｃ９．２４、Ｃ９．３６、Ｃ９．３８、Ｃ９．３
９、Ｃ９．４０、Ｃ９．５２、Ｃ９．５４、Ｃ９．５
５、Ｃ９．５６、Ｃ１０．１、Ｃ１０．３、Ｃ１０．
４、Ｃ１０．５、Ｃ１０．１７、Ｃ１０．２０、Ｃ１
０．４２、Ｃ１０．４４、Ｃ１０．４６、Ｃ１０．４
８、Ｃ１０．４９、Ｃ１０．５０、Ｃ１０．６２、Ｃ１
０．６４、Ｃ１０．６５、Ｃ１０．６６、Ｃ１０．７
８、Ｃ１０．８２、Ｃ１０．８４、Ｃ１０．８６、Ｃ１
０．８８、Ｃ１０．９２、Ｃ１０．９４、Ｃ１０．９
６、Ｃ１０．９８、Ｃ１１．１、Ｃ１１．４、Ｃ１１．
１７、Ｃ１１．２０、Ｃ１１．３３、Ｃ１１．４８、Ｃ
１１．６３、Ｃ１１．６４、Ｃ１１．７８、Ｃ１１．７
９、Ｃ１２．４５、Ｃ１２．４７、Ｃ１４．１５、Ｃ１
４．１８、Ｃ１４．３１、Ｃ１４．４５、Ｃ１４．７
４、Ｃ１５．３７、Ｃ１６．１１３、Ｃ１６．１２６、
Ｃ１８．１１８、Ｃ１８．１１９、Ｃ１８．１３０、Ｄ
１．１、Ｄ１．２、Ｄ１．４、Ｄ１．５、Ｄ１．８、Ｄ
１．１０、Ｄ１．１３、Ｄ１．１４、Ｄ１．１６、Ｄ
１．１８、Ｄ１．３５、Ｄ１．３７、Ｄ１．４０、Ｄ
１．４３、Ｄ１．４６、Ｄ１．４７、Ｄ１．４９、Ｄ
１．５０、Ｄ１．５１、Ｄ１．５５、Ｄ１．５６、Ｄ
１．５７、Ｄ１．６０、Ｄ１．６２、Ｄ１．６５、Ｄ
１．６７、Ｄ１．６８、Ｄ１．６９、Ｄ１．７０、Ｄ
１．７１、Ｄ１．７２、Ｄ１．７４、Ｄ１．７６、Ｄ
１．７８、Ｄ１．７９、Ｄ１．８０、Ｄ１．８１、Ｄ
１．８２、Ｄ１．８３、Ｄ１．８５、Ｄ１．８７、Ｄ
１．８８、Ｄ１．９０、Ｄ１．９１、Ｄ１．９２、Ｄ
１．９３、Ｄ１．９４、Ｄ１．９５、Ｄ１．９７、Ｄ
１．９８、Ｄ１．９９、Ｄ１．１００、Ｄ１．１０１、
Ｄ１．１０２、Ｄ１．１０３、Ｄ１．１０４、Ｄ１．１
０５、Ｄ１．１０６、Ｄ１．１０９、Ｄ１．１１０、Ｄ
１．１１２、Ｄ１．１１３、Ｄ１．１１４、Ｄ１．１１
６、Ｄ１．１１７、Ｄ１．１１８、Ｄ１．１１９、Ｄ
１．１２２、Ｄ１．１２３、Ｄ１．１２５、Ｄ１．１２
６、Ｄ１．１２８、Ｄ１．１２９、Ｄ１．１３０、Ｄ
１．１３１、Ｄ１．１３２、Ｄ１．１３５、Ｄ１．１３
６、Ｄ２．１、Ｄ２．４、Ｄ２．５、Ｄ２．６、Ｄ２．
７、Ｄ２．９、Ｄ２．１０、Ｄ２．１１、Ｄ２．１３、
Ｄ２．１４、Ｄ２．１５、Ｄ２．１７、Ｄ２．１９、Ｄ
２．２０、Ｄ２．２１、Ｄ２．２２、Ｄ２．２３、Ｄ
２．２５、Ｄ２．２６、Ｄ２．２８、Ｄ２．２９、Ｄ
２．３０、Ｄ２．３２、Ｄ２．４０、Ｄ２．４１、Ｄ
２．４２、Ｄ２．４４、Ｄ２．４５、Ｄ２．４６、Ｄ
２．４７、Ｄ２．４８、Ｄ２．５０、Ｄ２．５２、Ｄ
２．５３、Ｄ２．５４、Ｄ２．５５、Ｄ２．５６、Ｄ
２．５７、Ｄ２．６０、Ｄ２．６１、Ｄ２．６３、Ｄ
２．６５、Ｄ２．６６、Ｄ２．６７、Ｄ２．６８、Ｄ
２．７２、Ｄ２．７３、Ｄ２．７４、Ｄ２．７５、Ｄ
２．７６、Ｄ２．７７、Ｄ２．７８、Ｄ２．７９、Ｄ
２．８０、Ｄ２．８１、Ｄ２．８２、Ｄ２．８３、Ｄ
２．８４、Ｄ２．８５、Ｅ１．１、Ｅ１．３、Ｅ１．１
５、Ｅ１．１７、Ｅ４．１、Ｅ６．１、Ｅ７．５、Ｅ
７．１０、Ｅ７．１３１、Ｅ７．１３５、Ｆ１．１、Ｆ
１．３、Ｆ１．５、Ｆ１．１１、Ｆ１．１５、Ｆ１．２
１、Ｆ１．２５、Ｆ１．３１、Ｆ１．３３、Ｆ１．６
９、Ｆ３．１、Ｆ３．３、Ｆ３．１０、Ｆ３．１４、Ｆ
３．２０、Ｆ３．２１、Ｆ３．２２、Ｆ３．２９、Ｆ
３．３１、Ｆ３．５６、Ｆ４．１、Ｆ４．１１、Ｆ４．
１２、Ｆ４．１４、Ｆ４．１６、Ｆ４．１９、Ｆ４．２
０、Ｆ４．２２、Ｆ４．２３、Ｆ４．２５、Ｆ４．２
７、Ｆ４．２８、Ｆ４．３０、Ｆ４．３３、Ｆ４．４
０、Ｆ４．４１、Ｆ４．４３、Ｆ４．５９、Ｆ４．６
１、Ｆ４．６３、Ｆ４．６９、Ｆ４．７１、Ｆ４．７
９、Ｆ４．８１、Ｆ４．１０３、Ｆ５．３、Ｆ５．９、
Ｆ５．１３、Ｆ６．１１、Ｆ６．１２、Ｆ６．１５、Ｆ
６．１６、Ｆ６．１９、Ｆ６．２０、Ｆ６．２３、Ｆ
６．２４、Ｆ７．１７、Ｆ７．３４、Ｆ７．３９、Ｆ
７．４５、Ｆ７．５６、Ｆ７．６９、Ｆ７．９２、Ｆ
７．９９、Ｆ７．１２０、Ｆ７．１３６、Ｆ７．１４
７、Ｆ７．１６９、Ｆ７．１７３、Ｇ１．３、Ｇ１．
４、Ｇ１．５、Ｇ１．６、Ｇ１．８、Ｇ１．９、Ｇ１．
１０、Ｇ１．１１、Ｇ１．１３、Ｇ１．１４、Ｇ１．１
５、Ｇ１．１９、Ｇ１．２０、Ｇ１．３０、Ｇ１．３
２、Ｇ１．３４、Ｇ１．３５、Ｇ１．３６、Ｇ１．３
７、Ｇ１．３９、Ｇ１．４４、Ｇ１．５０、Ｇ１．５
２、Ｇ１．５５、Ｇ１．５７、Ｇ１．５８、Ｇ１．５
９、Ｇ１．６０、Ｇ１．６２、Ｇ１．６３、Ｇ１．６
４、Ｇ１．６７、Ｇ１．６８、Ｇ１．６９、Ｇ１．７
２、Ｇ１．７４、Ｇ１．７６、Ｇ１．７７、Ｇ１．８
１、Ｇ１．８５、Ｇ１．８７、Ｇ１．８９、Ｇ１．９
２、Ｇ１．９４、Ｇ１．９５、Ｇ１．９６、Ｇ１．９
７、Ｇ１．９９、Ｇ１．１０９、Ｇ１．１１３、Ｇ１．
１１４、Ｇ１．１１７、Ｇ１．１１８、Ｇ１．１２１、
Ｇ１．１２２、Ｇ１．１２７、Ｇ１．１２８、Ｇ２．１
３、Ｇ２．１４、Ｇ２．４２、Ｇ２．４９、Ｇ２．５
０、Ｇ２．６１、Ｇ２．６２、Ｇ２．８６、Ｇ２．９
７、Ｇ２．１１５、Ｇ２．１３７、Ｇ２．１４８、Ｇ
２．１６６、Ｇ５．３、Ｇ５．６、Ｇ５．１７、Ｇ５．
２０、Ｇ５．３３、Ｇ５．３８、Ｇ５．４５、Ｇ５．５
２、Ｇ６．３１、Ｇ８．３１、Ｇ８．３３、Ｇ８．３
６、Ｇ８．３８、Ｇ１０．５１、Ｇ１０．５７、Ｇ１
０．６１、Ｇ１０．６３、Ｈ４．３、Ｈ４．８、Ｈ４．
１９、Ｈ４．２２、Ｈ４．３５、Ｈ４．３８、Ｈ４．４
３、Ｈ４．５０、Ｈ４．９１、Ｈ７．４、Ｈ７．９、Ｈ
７．１８、Ｈ７．２１、Ｈ７．３６、Ｈ７．４１、Ｈ
７．４９、Ｈ７．６３、Ｈ７．１０６を挙げることがで
きる。[Table 8] ──────────────────────────────────── Number R ¹ R ^Two (R ^Three ) n ACR ^Four (R ^Five ) (R ⁶ ) m XQ Melting point (℃) ──────────────────────────────────── H1.1 Me H 2- CH _Two Cl OCH _Two 4-Me OS H1.2 Me H 2-CH _Two Cl SCH _Two 4-Me OS H1.3 Me H 2-CH _Two Cl OCH _Two 5-Me OS H1.4 Me H 2-CH _Two Cl SCH _Two 5-Me OS H1.5 Me H 2-CH _Two Cl OCH _Two 6-Me OS H1.6 Me H 2-CH _Two Cl SCH _Two 6-Me OS H1.7 Me H 2-CH _Two Cl OCH _Two 7-Me OS H1.8 Me H 2-CH _Two Cl SCH _Two 7-Me OS H1.9 Me H 2-CH _Two Cl OCH _Two 5-Et OS H1.10 Me H 2-CH _Two Cl SCH _Two 5-Et OS H1.11 Me H 2-CH _Two Cl OCH _Two 6-Et OS H1.12 Me H 2-CH _Two Cl SCH _Two 6-Et OS H1.13 Me H 2-CH _Two Cl OCH _Two 4-OMe OS H1.14 Me H 2-CH _Two Cl SCH _Two 4-OMe OS H1.15 Me H 2-CH _Two Cl OCH _Two 5-OMe OS H1.16 Me H 2-CH _Two Cl SCH _Two 5-OMe OS H1.17 Me H 2-CH _Two Cl OCH _Two 6-OMe OS H1.18 Me H 2-CH _Two Cl SCH _Two 6-OMe OS H1.19 Me H 2-CH _Two Cl OCH _Two 7-OMe OS H1.20 Me H 2-CH _Two Cl SCH _Two 7-OMe OS H1.21 Me H 2-CH _Two Cl OCH _Two 5-OEt OS H1.22 Me H 2-CH _Two Cl SCH _Two 5-OEt OS H1.23 Me H 2-CH _Two Cl OCH _Two 6-OEt OS H1.24 Me H 2-CH _Two Cl SCH _Two 6-OEt OS H1.25 Me H 2-CH _Two Cl OCH _Two 4-FOS H1.26 Me H 2-CH _Two Cl SCH _Two 4-FOS H1.27 Me H 2-CH _Two Cl OCH _Two 5-FOS H1.28 Me H 2-CH _Two Cl SCH _Two 5-FOS H1.29 Me H 2-CH _Two Cl OCH _Two 6-FOS H1.30 Me H 2-CH _Two Cl SCH _Two 6-FOS H1.31 Me H 2-CH _Two Cl OCH _Two 7-FOS H1.32 Me H 2-CH _Two Cl SCH _Two 7-FOS H1.33 Me H 2-CH _Two Cl OCH _Two 5-Cl OS H1.34 Me H 2-CH _Two Cl SCH _Two 5-Cl OS H1.35 Me H 2-CH _Two Cl OCH _Two 6-Cl OS H1.36 Me H 2-CH _Two Cl SCH _Two 6-Cl OS H1.37 Me H 2-CH _Two Cl OCH _Two 4-CF _Three OS H1.38 Me H 2-CH _Two Cl SCH _Two 4-CF _Three OS H1.39 Me H 2-CH _Two Cl OCH _Two 5-CF _Three OS H1.40 Me H 2-CH _Two Cl SCH _Two 5-CF _Three OS H1.41 Me H 2-CH _Two Cl OCH _Two 6-CF _Three OS H1.42 Me H 2-CH _Two Cl SCH _Two 6-CF _Three OS H1.43 Me H 2-CH _Two Cl OCH _Two 7-CF _Three OS H1.44 Me H 2-CH _Two Cl SCH _Two 7-CF _Three OS H1.45 Me H 2-CH _Two Cl OCH _Two 5-OCF _Three OS H1.46 Me H 2-CH _Two Cl SCH _Two 5-OCF _Three OS H1.47 Me H 2-CH _Two Cl OCH _Two 6-OCF _Three OS H1.48 Me H 2-CH _Two Cl SCH _Two 6-OCF _Three OS H1.49 Me H 3-CH _Two Cl OCH _Two 4-Me OS H1.50 Me H 3-CH _Two Cl SCH _Two 4-Me OS H1.51 Me H 3-CH _Two Cl OCH _Two 5-Me OS H1.52 Me H 3-CH _Two Cl SCH _Two 5-Me OS H1.54 Me H 3-CH _Two Cl SCH _Two 6-Me OS H1.55 Me H 3-CH _Two Cl OCH _Two 7-Me OS H1.56 Me H 3-CH _Two Cl SCH _Two 7-Me OS H1.57 Me H 3-CH _Two Cl OCH _Two 5-Et OS H1.58 Me H 3-CH _Two Cl SCH _Two 5-Et OS H1.59 Me H 3-CH _Two Cl OCH _Two 6-Et OS H1.60 Me H 3-CH _Two Cl SCH _Two 6-Et OS H1.61 Me H 3-CH _Two Cl OCH _Two 4-OMe OS H1.62 Me H 3-CH _Two Cl SCH _Two 4-OMe OS H1.63 Me H 3-CH _Two Cl OCH _Two 5-OMe OS H1.64 Me H 3-CH _Two Cl SCH _Two 5-OMe OS H1.65 Me H 3-CH _Two Cl OCH _Two 6-OMe OS H1.66 Me H 3-CH _Two Cl SCH _Two 6-OMe OS H1.67 Me H 3-CH _Two Cl OCH _Two 7-OMe OS H1.68 Me H 3-CH _Two Cl SCH _Two 7-OMe OS H1.69 Me H 3-CH _Two Cl OCH _Two 5-OEt OS H1.70 Me H 3-CH _Two Cl SCH _Two 5-OEt OS H1.71 Me H 3-CH _Two Cl OCH _Two 6-OEt OS H1.72 Me H 3-CH _Two Cl SCH _Two 6-OEt OS H1.73 Me H 3-CH _Two Cl OCH _Two 4-FOS H1.74 Me H 3-CH _Two Cl SCH _Two 4-FOS H1.75 Me H 3-CH _Two Cl OCH _Two 5-FOS H1.76 Me H 3-CH _Two Cl SCH _Two 5-FOS H1.77 Me H 3-CH _Two Cl OCH _Two 6-FOS H1.78 Me H 3-CH _Two Cl SCH _Two 6-FOS H1.79 Me H 3-CH _Two Cl OCH _Two 7-FOS H1.80 Me H 3-CH _Two Cl SCH _Two 7-FOS H1.81 Me H 3-CH _Two Cl OCH _Two 5-Cl OS H1.83 Me H 3-CH _Two Cl SCH _Two 5-Cl OS H1.84 Me H 3-CH _Two Cl OCH _Two 6-Cl OS H1.85 Me H 3-CH _Two Cl SCH _Two 6-Cl OS H1.86 Me H 3-CH _Two Cl OCH _Two 4-CF _Three OS H1.87 Me H 3-CH _Two Cl SCH _Two 4-CF _Three OS H1.88 Me H 3-CH _Two Cl OCH _Two 5-CF _Three OS H1.89 Me H 3-CH _Two Cl SCH _Two 5-CF _Three OS H1.90 Me H 3-CH _Two Cl OCH _Two 6-CF _Three OS H1.91 Me H 3-CH _Two Cl SCH _Two 6-CF _Three OS H1.92 Me H 3-CH _Two Cl OCH _Two 7-CF _Three OS H1.93 Me H 3-CH _Two Cl SCH _Two 7-CF _Three OS H1.94 Me H 3-CH _Two Cl OCH _Two 5-OCF _Three OS H1.95 Me H 3-CH _Two Cl SCH _Two 5-OCF _Three OS H1.96 Me H 3-CH _Two Cl OCH _Two 6-OCF _Three OS H1.97 Me H 3-CH _Two Cl SCH _Two 6-OCF _Three OS H2.1 Me H 2-CH _Two Br OCH _Two 4-Me OS H2.2 Me H 2-CH _Two Br SCH _Two 4-Me OS H2.3 Me H 2-CH _Two Br OCH _Two 5-Me OS H2.4 Me H 2-CH _Two Br SCH _Two 5-Me OS H2.5 Me H 2-CH _Two Br OCH _Two 6-Me OS H2.6 Me H 2-CH _Two Br SCH _Two 6-Me OS H2.7 Me H 2-CH _Two Br OCH _Two 7-Me OS H2.8 Me H 2-CH _Two Br SCH _Two 7-Me OS H2.9 Me H 2-CH _Two Br OCH _Two 5-Et OS H2.10 Me H 2-CH _Two Br SCH _Two 5-Et OS H2.11 Me H 2-CH _Two Br OCH _Two 6-Et OS H2.12 Me H 2-CH _Two Br SCH _Two 6-Et OS H2.13 Me H 2-CH _Two Br OCH _Two 4-OMe OS H2.14 Me H 2-CH _Two Br SCH _Two 4-OMe OS H2.15 Me H 2-CH _Two Br OCH _Two 5-OMe OS H2.16 Me H 2-CH _Two Br SCH _Two 5-OMe OS H2.17 Me H 2-CH _Two Br OCH _Two 6-OMe OS H2.18 Me H 2-CH _Two Br SCH _Two 6-OMe OS H2.19 Me H 2-CH _Two Br OCH _Two 7-OMe OS H2.20 Me H 2-CH _Two Br SCH _Two 7-OMe OS H2.21 Me H 2-CH _Two Br OCH _Two 5-OEt OS H2.22 Me H 2-CH _Two Br SCH _Two 5-OEt OS H2.23 Me H 2-CH _Two Br OCH _Two 6-OEt OS H2.24 Me H 2-CH _Two Br SCH _Two 6-OEt OS H2.25 Me H 2-CH _Two Br OCH _Two 4-FOS H2.26 Me H 2-CH _Two Br SCH _Two 4-FOS H2.27 Me H 2-CH _Two Br OCH _Two 5-FOS H2.28 Me H 2-CH _Two Br SCH _Two 5-FOS H2.29 Me H 2-CH _Two Br OCH _Two 6-FOS H2.30 Me H 2-CH _Two Br SCH _Two 6-FOS H2.31 Me H 2-CH _Two Br OCH _Two 7-FOS H2.32 Me H 2-CH _Two Br SCH _Two 7-FOS H2.33 Me H 2-CH _Two Br OCH _Two 5-Cl OS H2.34 Me H 2-CH _Two Br SCH _Two 5-Cl OS H2.35 Me H 2-CH _Two Br OCH _Two 6-Cl OS H2.36 Me H 2-CH _Two Br SCH _Two 6-Cl OS H2.37 Me H 2-CH _Two Br OCH _Two 4-CF _Three OS H2.38 Me H 2-CH _Two Br SCH _Two 4-CF _Three OS H2.39 Me H 2-CH _Two Br OCH _Two 5-CF _Three OS H2.40 Me H 2-CH _Two Br SCH _Two 5-CF _Three OS H2.41 Me H 2-CH _Two Br OCH _Two 6-CF _Three OS H2.42 Me H 2-CH _Two Br SCH _Two 6-CF _Three OS H2.43 Me H 2-CH _Two Br OCH _Two 7-CF _Three OS H2.44 Me H 2-CH _Two Br SCH _Two 7-CF _Three OS H2.45 Me H 2-CH _Two Br OCH _Two 5-OCF _Three OS H2.46 Me H 2-CH _Two Br SCH _Two 5-OCF _Three OS H2.47 Me H 2-CH _Two Br OCH _Two 6-OCF _Three OS H2.48 Me H 2-CH _Two Br SCH _Two 6-OCF _Three OS H2.49 Me H 3-CH _Two Br OCH _Two 4-Me OS H2.50 Me H 3-CH _Two Br SCH _Two 4-Me OS H2.51 Me H 3-CH _Two Br OCH _Two 5-Me OS H2.52 Me H 3-CH _Two Br SCH _Two 5-Me OS H2.53 Me H 3-CH _Two Br OCH _Two 6-Me OS H2.54 Me H 3-CH _Two Br SCH _Two 6-Me OS H2.55 Me H 3-CH _Two Br OCH _Two 7-Me OS H2.56 Me H 3-CH _Two Br SCH _Two 7-Me OS H2.57 Me H 3-CH _Two Br OCH _Two 5-Et OS H2.58 Me H 3-CH _Two Br SCH _Two 5-Et OS H2.59 Me H 3-CH _Two Br OCH _Two 6-Et OS H2.60 Me H 3-CH _Two Br SCH _Two 6-Et OS H2.61 Me H 3-CH _Two Br OCH _Two 4-OMe OS H2.62 Me H 3-CH _Two Br SCH _Two 4-OMe OS H2.63 Me H 3-CH _Two Br OCH _Two 5-OMe OS H2.64 Me H 3-CH _Two Br SCH _Two 5-OMe OS H2.65 Me H 3-CH _Two Br OCH _Two 6-OMe OS H2.67 Me H 3-CH _Two Br SCH _Two 6-OMe OS H2.68 Me H 3-CH _Two Br OCH _Two 7-OMe OS H2.69 Me H 3-CH _Two Br SCH _Two 7-OMe OS H2.70 Me H 3-CH _Two Br OCH _Two 5-OEt OS H2.71 Me H 3-CH _Two Br SCH _Two 5-OEt OS H2.72 Me H 3-CH _Two Br OCH _Two 6-OEt OS H2.73 Me H 3-CH _Two Br SCH _Two 6-OEt OS H2.74 Me H 3-CH _Two Br OCH _Two 4-FOS H2.75 Me H 3-CH _Two Br SCH _Two 4-FOS H2.76 Me H 3-CH _Two Br OCH _Two 5-FOS H2.77 Me H 3-CH _Two Br SCH _Two 5-FOS H2.78 Me H 3-CH _Two Br OCH _Two 6-FOS H2.79 Me H 3-CH _Two Br SCH _Two 6-FOS H2.80 Me H 3-CH _Two Br OCH _Two 7-FOS H2.81 Me H 3-CH _Two Br SCH _Two 7-FOS H2.82 Me H 3-CH _Two Br OCH _Two 5-Cl OS H2.83 Me H 3-CH _Two Br SCH _Two 5-Cl OS H2.84 Me H 3-CH _Two Br OCH _Two 6-Cl OS H2.85 Me H 3-CH _Two Br SCH _Two 6-Cl OS H2.86 Me H 3-CH _Two Br OCH _Two 4-CF _Three OS H2.87 Me H 3-CH _Two Br SCH _Two 4-CF _Three OS H2.88 Me H 3-CH _Two Br OCH _Two 5-CF _Three OS H2.89 Me H 3-CH _Two Br SCH _Two 5-CF _Three OS H2.90 Me H 3-CH _Two Br OCH _Two 6-CF _Three OS H2.91 Me H 3-CH _Two Br SCH _Two 6-CF _Three OS H2.92 Me H 3-CH _Two Br OCH _Two 7-CF _Three OS H2.93 Me H 3-CH _Two Br SCH _Two 7-CF _Three OS H2.94 Me H 3-CH _Two Br OCH _Two 5-OCF _Three OS H2.95 Me H 3-CH _Two Br SCH _Two 5-OCF _Three OS H2.96 Me H 3-CH _Two Br OCH _Two 6-OCF _Three OS H2.97 Me H 3-CH _Two Br SCH _Two 6-OCF _Three OS H3.1 Me H 2-F OCH _Two 4-Me OS H3.2 Me H 2-F SCH _Two 4-Me OS H3.3 MeO H 2-F OCH _Two 4-Me OS H3.4 Me H 2-F OCH _Two 5-Me OS H3.5 Me H 2-F SCH _Two 5-Me OS H3.6 MeO H 2-F OCH _Two 5-Me OS H3.7 MeO H 2-F OCH _Two 5-Me OO H3.8 Me H 2-F OCH _Two 6-Me OS H3.9 Me H 2-F SCH _Two 6-Me OS H3.10 MeO H 2-F OCH _Two 6-Me OS H3.11 MeO H 2-F OCH _Two 6-Me OO H3.12 Me H 2-F OCH _Two 7-Me OS H3.13 Me H 2-F SCH _Two 7-Me OS H3.14 MeO H 2-F OCH _Two 7-Me OS H3.15 Me H 2-F OCH _Two 5-Et OS H3.16 Me H 2-F SCH _Two 5-Et OS H3.17 MeO H 2-F OCH _Two 5-Et OS H3.18 MeO H 2-F SCH _Two 5-Et OS H3.19 Me H 2-F OCH _Two 6-Et OS H3.20 Me H 2-F SCH _Two 6-Et OS H3.21 MeO H 2-F OCH _Two 6-Et OS H3.22 MeO H 2-F SCH _Two 6-Et OS H3.23 Me H 2-F OCH _Two 4-FOS H3.24 Me H 2-F SCH _Two 4-FOS H3.25 MeO H 2-F OCH _Two 4-FOS H3.26 Me H 2-F OCH _Two 5-FOS H3.27 Me H 2-F SCH _Two 5-FOS H3.28 MeO H 2-F OCH _Two 5-FOS H3.29 MeO H 2-F SCH _Two 5-FOS H3.30 MeO H 2-F OCH _Two 5-FOO H3.31 MeO H 2-F SCH _Two 5-FOO H3.32 Me H 2-F OCH _Two 6-FOS H3.33 Me H 2-F SCH _Two 6-FOS H3.34 MeO H 2-F OCH _Two 6-FOS H3.35 MeO H 2-F OCH _Two 6-FOO H3.36 Me H 2-F OCH _Two 7-FOS H3.37 Me H 2-F SCH _Two 7-FOS H3.38 MeO H 2-F OCH _Two 7-FOS H3.39 MeO H 2-F OCH _Two 7-FOO H3.40 Me H 2-F OCH _Two 5-Cl OS H3.41 Me H 2-F SCH _Two 5-Cl OS H3.42 Me H 2-F OCH _Two 6-Cl OS H3.43 Me H 2-F SCH _Two 6-Cl OS H3.44 Me H 2-F OCH _Two 4-OMe OS H3.45 Me H 2-F SCH _Two 4-OMe OS H3.46 Me H 2-F OCH _Two 5-OMe OS H3.47 Me H 2-F SCH _Two 5-OMe OS H3.48 MeO H 2-F OCH _Two 5-OMe OS H3.49 Me H 2-F OCH _Two 6-OMe OS H3.50 Me H 2-F SCH _Two 6-OMe OS H3.51 MeO H 2-F OCH _Two 6-OMe OS H3.52 Me H 2-F OCH _Two 6-OMe OO H3.53 MeO H 2-F OCH _Two 6-OMe OO H3.54 Me H 2-F OCH _Two 7-OMe OS H3.55 Me H 2-F SCH _Two 7-OMe OS H3.56 Me H 2-F OCH _Two 5-OEt OS H3.57 Me H 2-F SCH _Two 5-OEt OS H3.58 Me H 2-F OCH _Two 6-OEt OS H3.59 Me H 2-F SCH _Two 6-OEt OS H3.60 Me H 2-F OCH _Two 4-CF _Three OS H3.61 Me H 2-F SCH _Two 4-CF _Three OS H3.62 Me H 2-F OCH _Two 5-CF _Three OS H3.63 Me H 2-F SCH _Two 5-CF _Three OS H3.64 MeO H 2-F OCH _Two 5-CF _Three OS H3.65 Me H 2-F OCH _Two 6-CF _Three OS H3.66 Me H 2-F SCH _Two 6-CF _Three OS H3.67 Me H 2-F OCH _Two 7-CF _Three OS H3.68 Me H 2-F SCH _Two 7-CF _Three OS H3.69 Me H 2-F OCH _Two 5-OCF _Three OS H3.70 Me H 2-F SCH _Two 5-OCF _Three OS H3.71 Me H 2-F OCH _Two 6-OCF _Three OS H3.72 Me H 2-F SCH _Two 6-OCF _Three OS H3.73 Me H 3-F OCH _Two 4-Me OS H3.74 Me H 3-F SCH _Two 4-Me OS H3.75 Me H 3-F OCH _Two 5-Me OS H3.76 Me H 3-F SCH _Two 5-Me OS H3.77 Me H 3-F OCH _Two 6-Me OS H3.78 Me H 3-F SCH _Two 6-Me OS H3.79 Me H 3-F OCH _Two 7-Me OS H3.80 Me H 3-F SCH _Two 7-Me OS H3.81 Me H 3-F OCH _Two 5-Et OS H3.82 Me H 3-F SCH _Two 5-Et OS H3.83 Me H 3-F OCH _Two 6-Et OS H3.84 Me H 3-F SCH _Two 6-Et OS H3.85 Me H 3-F OCH _Two 4-OMe OS H3.86 Me H 3-F SCH _Two 4-OMe OS H3.87 Me H 3-F OCH _Two 5-OMe OS H3.88 Me H 3-F SCH _Two 5-OMe OS H3.89 Me H 3-F OCH _Two 6-OMe OS H3.90 Me H 3-F SCH _Two 6-OMe OS H3.91 Me H 3-F OCH _Two 7-OMe OS H3.92 Me H 3-F SCH _Two 7-OMe OS H3.93 Me H 3-F OCH _Two 5-OEt OS H3.94 Me H 3-F SCH _Two 5-OEt OS H3.95 Me H 3-F OCH _Two 6-OEt OS H3.96 Me H 3-F SCH _Two 6-OEt OS H3.97 Me H 3-F OCH _Two 4-FOS H3.98 Me H 3-F SCH _Two 4-FOS H3.99 Me H 3-F OCH _Two 5-FOS H3.100 Me H 3-F SCH _Two 5-FOS H3.101 Me H 3-F OCH _Two 6-FOS H3.102 Me H 3-F SCH _Two 6-FOS H3.103 Me H 3-F OCH _Two 7-FOS H3.104 Me H 3-F SCH _Two 7-FOS H3.105 Me H 3-F OCH _Two 5-Cl OS H3.106 Me H 3-F SCH _Two 5-Cl OS H3.107 Me H 3-F OCH _Two 6-Cl OS H3.108 Me H 3-F SCH _Two 6-Cl OS H3.109 Me H 3-F OCH _Two 4-CF _Three OS H3.110 Me H 3-F SCH _Two 4-CF _Three OS H3.111 Me H 3-F OCH _Two 5-CF _Three OS H3.112 Me H 3-F SCH _Two 5-CF _Three OS H3.113 Me H 3-F OCH _Two 6-CF _Three OS H3.114 Me H 3-F SCH _Two 6-CF _Three OS H3.115 Me H 3-F OCH _Two 7-CF _Three OS H3.116 Me H 3-F SCH _Two 7-CF _Three OS H3.117 Me H 3-F OCH _Two 5-OCF _Three OS H3.118 Me H 3-F SCH _Two 5-OCF _Three OS H3.119 Me H 3-F OCH _Two 6-OCF _Three OS H3.120 Me H 3-F SCH _Two 6-OCF _Three OS H4.1 Me H 2-Cl OCH _Two 4-Me OS H4.3 Me H 2-Cl OCH _Two 5-Me OS 176-179 H4.4 Me H 2-Cl SCH _Two 5-Me OS H4.5 MeO H 2-Cl OCH _Two 5-Me OS H4.6 Me H 2-Cl OCH _Two 5-Me OO H4.7 MeO H 2-Cl OCH _Two 5-Me OO H4.8 Me H 2-Cl OCH _Two 6-Me OS 151-153 H4.9 Me H 2-Cl SCH _Two 6-Me OS H4.10 MeO H 2-Cl OCH _Two 6-Me OS H4.11 Me H 2-Cl OCH _Two 7-Me OS H4.12 Me H 2-Cl SCH _Two 7-Me OS H4.13 Me H 2-Cl OCH _Two 5-Et OS H4.14 Me H 2-Cl SCH _Two 5-Et OS H4.15 Me H 2-Cl OCH _Two 6-Et OS H4.16 Me H 2-Cl SCH _Two 6-Et OS H4.17 Me H 2-Cl OCH _Two 4-OMe OS H4.18 Me H 2-Cl SCH _Two 4-OMe OS H4.19 Me H 2-Cl OCH _Two 5-OMe OS 160-163 H4.20 Me H 2-Cl SCH _Two 5-OMe OS H4.21 MeO H 2-Cl OCH _Two 5-OMe OS H4.22 Me H 2-Cl OCH _Two 6-OMe OS 148-150 H4.23 Me H 2-Cl SCH _Two 6-OMe OS H4.24 MeO H 2-Cl OCH _Two 6-OMe OS H4.25 Me H 2-Cl OCH _Two 6-OMe OO H4.26 MeO H 2-Cl OCH _Two 6-OMe OO H4.27 Me H 2-Cl OCH _Two 7-OMe OS H4.28 Me H 2-Cl SCH _Two 7-OMe OS H4.29 Me H 2-Cl OCH _Two 5-OEt OS H4.30 Me H 2-Cl SCH _Two 5-OEt OS H4.31 Me H 2-Cl OCH _Two 6-OEt OS H4.32 Me H 2-Cl SCH _Two 6-OEt OS H4.33 Me H 2-Cl OCH _Two 4-FOS H4.34 Me H 2-Cl SCH _Two 4-FOS H4.35 Me H 2-Cl OCH _Two 5-FOS 160-167 H4.36 Me H 2-Cl SCH _Two 5-FOS H4.37 MeO H 2-Cl OCH _Two 5-FOS H4.38 Me H 2-Cl OCH _Two 6-FOS 174-176 H4.39 Me H 2-Cl SCH _Two 6-FOS H4.40 MeO H 2-Cl OCH _Two 6-FOS H4.41 Me H 2-Cl OCH _Two 7-FOS H4.42 Me H 2-Cl SCH _Two 7-FOS H4.43 Me H 2-Cl OCH _Two 5-Cl OS 192-193 H4.44 Me H 2-Cl SCH _Two 5-Cl OS H4.45 MeO H 2-Cl OCH _Two 5-Cl OS H4.46 Me H 2-Cl OCH _Two 6-Cl OS H4.47 Me H 2-Cl SCH _Two 6-Cl OS H4.48 Me H 2-Cl OCH _Two 4-CF _Three OS H4.49 Me H 2-Cl SCH _Two 4-CF _Three OS H4.50 Me H 2-Cl OCH _Two 5-CF _Three OS 183-184 H4.51 Me H 2-Cl SCH _Two 5-CF _Three OS H4.52 MeO H 2-Cl OCH _Two 5-CF _Three OS H4.53 Me H 2-Cl OCH _Two 6-CF _Three OS H4.54 Me H 2-Cl SCH _Two 6-CF _Three OS H4.55 Me H 2-Cl OCH _Two 7-CF _Three OS H4.56 Me H 2-Cl SCH _Two 7-CF _Three OS H4.57 Me H 2-Cl OCH _Two 5-OCF3 OS H4.58 Me H 2-Cl SCH _Two 5-OCF3 OS H4.59 Me H 2-Cl OCH _Two 6-OCF3 OS H4.60 Me H 2-Cl SCH _Two 6-OCF3 OS H4.61 Me H 2-Cl OCH _Two 4,5-Me _Two OS H4.62 Me H 2-Cl SCH _Two 4,5-Me _Two OS H4.63 Me H 2-Cl OCH _Two 4,6-Me _Two OS H4.64 Me H 2-Cl SCH _Two 4,6-Me _Two OS H4.65 Me H 2-Cl OCH _Two 4,7-Me _Two OS H4.66 Me H 2-Cl SCH _Two 4,7-Me _Two OS H4.67 Me H 2-Cl OCH _Two 5,6-Me _Two OS H4.68 Me H 2-Cl SCH _Two 5,6-Me _Two OS H4.69 Me H 2-Cl OCH _Two 5,7-Me _Two OS H4.70 Me H 2-Cl SCH _Two 5,7-Me _Two OS H4.71 Me H 2-Cl OCH _Two 6,7-Me _Two OS H4.72 Me H 2-Cl SCH _Two 6,7-Me _Two OS H4.73 Me H 2-Cl OCH _Two 4,5- (OMe) _Two OS H4.74 Me H 2-Cl SCH _Two 4,5- (OMe) _Two OS H4.75 Me H 2-Cl OCH _Two 4,6- (OMe) _Two OS H4.76 Me H 2-Cl SCH _Two 4,6- (OMe) _Two OS H4.77 Me H 2-Cl OCH _Two 4,7- (OMe) _Two OS H4.78 Me H 2-Cl SCH _Two 4,7- (OMe) _Two OS H4.79 Me H 2-Cl OCH _Two 5,6- (OMe) _Two OS H4.80 Me H 2-Cl SCH _Two 5,6- (OMe) _Two OS H4.81 Me H 2-Cl OCH _Two 5,7- (OMe) _Two OS H4.82 Me H 2-Cl SCH _Two 5,7- (OMe) _Two OS H4.83 Me H 2-Cl OCH _Two 6,7- (OMe) _Two OS H4.84 Me H 2-Cl SCH _Two 6,7- (OMe) _Two OS H4.85 Me H 2-Cl OCH _Two 4,5-F _Two OS H4.86 Me H 2-Cl SCH _Two 4,5-F _Two OS H4.87 Me H 2-Cl OCH _Two 4,6-F _Two OS H4.88 Me H 2-Cl SCH _Two 4,6-F _Two OS H4.89 Me H 2-Cl OCH _Two 4,7-F _Two OS H4.90 Me H 2-Cl SCH _Two 4,7-F _Two OS H4.91 Me H 2-Cl OCH _Two 5,6-F _Two OS 170-172 H4.92 Me H 2-Cl SCH _Two 5,6-F _Two OS H4.93 MeO H 2-Cl OCH _Two 5,6-F _Two OS H4.94 Me H 2-Cl OCH _Two 5,7-F _Two OS H4.95 Me H 2-Cl SCH _Two 5,7-F _Two OS H4.96 Me H 2-Cl OCH _Two 6,7-F _Two OS H4.97 Me H 2-Cl SCH _Two 6,7-F _Two OS H4.98 Me H 2-Cl OCH _Two 4,5-Cl _Two OS H4.99 Me H 2-Cl SCH _Two 4,5-Cl _Two OS H4.100 Me H 2-Cl OCH _Two 4,6-Cl _Two OS H4.101 Me H 2-Cl SCH _Two 4,6-Cl _Two OS H4.102 Me H 2-Cl OCH _Two 4,7-Cl _Two OS H4.103 Me H 2-Cl SCH _Two 4,7-Cl _Two OS H4.104 Me H 2-Cl OCH _Two 5,6-Cl _Two OS H4.105 Me H 2-Cl SCH _Two 5,6-Cl _Two OS H4.106 Me H 2-Cl OCH _Two 5,7-Cl _Two OS H4.107 Me H 2-Cl SCH _Two 5,7-Cl _Two OS H4.108 Me H 2-Cl OCH _Two 6,7-Cl _Two OS H4.109 Me H 2-Cl SCH _Two 6,7-Cl _Two OS H5.1 Me H 2-Cl OCH _Two 4,5- (CF _Three ) _Two OS H5.2 Me H 2-Cl SCH _Two 4,5- (CF _Three ) _Two OS H5.3 Me H 2-Cl OCH _Two 4,6- (CF _Three ) _Two OS H5.4 Me H 2-Cl SCH _Two 4,6- (CF _Three ) _Two OS H5.5 Me H 2-Cl OCH _Two 4,7- (CF _Three ) _Two OS H5.6 Me H 2-Cl SCH _Two 4,7- (CF _Three ) _Two OS H5.7 Me H 2-Cl OCH _Two 5,6- (CF _Three ) _Two OS H5.8 Me H 2-Cl SCH _Two 5,6- (CF _Three ) _Two OS H5.9 Me H 2-Cl OCH _Two 5,7- (CF _Three ) _Two OS H5.10 Me H 2-Cl SCH _Two 5,7- (CF _Three ) _Two OS H5.11 Me H 2-Cl OCH _Two 6,7- (CF _Three ) _Two OS H5.12 Me H 2-Cl SCH _Two 6,7- (CF _Three ) _Two OS H5.13 Me H 2-Cl OCH _Two 4-F, 5-Me OS H5.14 Me H 2-Cl SCH _Two 4-F, 5-Me OS H5.15 Me H 2-Cl OCH _Two 4-F, 6-Me OS H5.16 Me H 2-Cl SCH _Two 4-F, 6-Me OS H5.17 Me H 2-Cl OCH _Two 4-F, 7-Me OS H5.18 Me H 2-Cl SCH _Two 4-F, 7-Me OS H5.19 Me H 2-Cl OCH _Two 4-Me, 5-FOS H5.20 Me H 2-Cl SCH _Two 4-Me, 5-FOS H5.21 Me H 2-Cl OCH _Two 5-F, 6-Me OS H5.22 Me H 2-Cl SCH _Two 5-F, 6-Me OS H5.23 Me H 2-Cl OCH _Two 5-F, 7-Me OS H5.24 Me H 2-Cl SCH _Two 5-F, 7-Me OS H5.25 Me H 2-Cl OCH _Two 4-Me, 6-FOS H5.26 Me H 2-Cl SCH _Two 4-Me, 6-FOS H5.27 Me H 2-Cl OCH _Two 5-Me, 6-FOS H5.28 Me H 2-Cl SCH _Two 5-Me, 6-FOS H5.29 Me H 2-Cl OCH _Two 6-F, 7-Me OS H5.30 Me H 2-Cl SCH _Two 6-F, 7-Me OS H5.31 Me H 2-Cl OCH _Two 4-Me, 7-FOS H5.32 Me H 2-Cl SCH _Two 4-Me, 7-FOS H5.34 Me H 2-Cl OCH _Two 5-Me, 7-FOS H5.35 Me H 2-Cl SCH _Two 5-Me, 7-FOS H5.36 Me H 2-Cl OCH _Two 6-Me, 7-FOS H5.37 Me H 2-Cl SCH _Two 6-Me, 7-FOS H5.38 Me H 2-Cl OCH _Two 4-Cl, 5-Me OS H5.39 Me H 2-Cl SCH _Two 4-Cl, 5-Me OS H5.40 Me H 2-Cl OCH _Two 4-Cl, 6-Me OS H5.41 Me H 2-Cl SCH _Two 4-Cl, 6-Me OS H5.42 Me H 2-Cl OCH _Two 4-Cl, 7-Me OS H5.43 Me H 2-Cl SCH _Two 4-Cl, 7-Me OS H5.44 Me H 2-Cl OCH _Two 4-Me, 5-Cl OS H5.45 Me H 2-Cl SCH _Two 4-Me, 5-Cl OS H5.46 Me H 2-Cl OCH _Two 5-Cl, 6-Me OS H5.47 Me H 2-Cl SCH _Two 5-Cl, 6-Me OS H5.48 Me H 2-Cl OCH _Two 5-Cl, 7-Me OS H5.49 Me H 2-Cl SCH _Two 5-Cl, 7-Me OS H5.50 Me H 2-Cl OCH _Two 4-Me, 6-Cl OS H5.51 Me H 2-Cl SCH _Two 4-Me, 6-Cl OS H5.52 Me H 2-Cl OCH _Two 5-Me, 6-Cl OS H5.53 Me H 2-Cl SCH _Two 5-Me, 6-Cl OS H5.54 Me H 2-Cl OCH _Two 6-Cl, 7-Me OS H5.56 Me H 2-Cl SCH _Two 6-Cl, 7-Me OS H5.57 Me H 2-Cl OCH _Two 4-Me, 7-Cl OS H5.58 Me H 2-Cl SCH _Two 4-Me, 7-Cl OS H5.59 Me H 2-Cl OCH _Two 5-Me, 7-Cl OS H5.60 Me H 2-Cl SCH _Two 5-Me, 7-Cl OS H5.61 Me H 2-Cl OCH _Two 6-Me, 7-Cl OS H5.62 Me H 2-Cl SCH _Two 6-Me, 7-Cl OS H5.63 Me H 2-Cl OCH _Two 4-Cl, 5-FOS H5.64 Me H 2-Cl SCH _Two 4-Cl, 5-FOS H5.65 Me H 2-Cl OCH _Two 4-Cl, 6-FOS H5.66 Me H 2-Cl SCH _Two 4-Cl, 6-FOS H5.67 Me H 2-Cl OCH _Two 4-Cl, 7-FOS H5.68 Me H 2-Cl SCH _Two 4-Cl, 7-FOS H5.69 Me H 2-Cl OCH _Two 4-F, 5-Cl OS H5.70 Me H 2-Cl SCH _Two 4-F, 5-Cl OS H5.71 Me H 2-Cl OCH _Two 5-Cl, 6-FOS H5.72 Me H 2-Cl SCH _Two 5-Cl, 6-FOS H5.73 Me H 2-Cl OCH _Two 5-Cl, 7-FOS H5.74 Me H 2-Cl SCH _Two 5-Cl, 7-FOS H5.75 Me H 2-Cl OCH _Two 4-F, 6-Cl OS H5.76 Me H 2-Cl SCH _Two 4-F, 6-Cl OS H5.77 Me H 2-Cl OCH _Two 5-F, 6-Cl OS H5.78 Me H 2-Cl SCH _Two 5-F, 6-Cl OS H5.79 Me H 2-Cl OCH _Two 6-Cl, 7-FOS H5.80 Me H 2-Cl SCH _Two 6-Cl, 7-FOS H5.81 Me H 2-Cl OCH _Two 4-F, 7-Cl OS H5.82 Me H 2-Cl SCH _Two 4-F, 7-Cl OS H5.83 Me H 2-Cl OCH _Two 5-F, 7-Cl OS H5.84 Me H 2-Cl SCH _Two 5-F, 7-Cl OS H5.85 Me H 2-Cl OCH _Two 6-F, 7-Cl OS H5.86 Me H 2-Cl SCH _Two 6-F, 7-Cl OS H6.1 Me H 3-Cl OCH _Two 4-Me OS H6.2 Me H 3-Cl SOCH _Two 4-Me OS H6.3 Me H 3-Cl OCH _Two 5-Me OS H6.4 Me H 3-Cl SCH _Two 5-Me OS H6.5 Me H 3-Cl OCH _Two 6-Me OS H6.6 Me H 3-Cl SCH _Two 6-Me OS H6.7 Me H 3-Cl OCH _Two 7-Me OS H6.8 Me H 3-Cl SCH _Two 7-Me OS H6.9 Me H 3-Cl OCH _Two 5-Et OS H6.10 Me H 3-Cl SCH _Two 5-Et OS H6.11 Me H 3-Cl OCH _Two 6-Et OS H6.12 Me H 3-Cl SCH _Two 6-Et OS H6.13 Me H 3-Cl OCH _Two 4-OMe OS H6.14 Me H 3-Cl SCH _Two 4-OMe OS H6.15 Me H 3-Cl OCH _Two 5-OMe OS H6.16 Me H 3-Cl SCH _Two 5-OMe OS H6.17 Me H 3-Cl OCH _Two 6-OMe OS H6.18 Me H 3-Cl SCH _Two 6-OMe OS H6.19 Me H 3-Cl OCH _Two 7-OMe OS H6.20 Me H 3-Cl SCH _Two 7-OMe OS H6.21 Me H 3-Cl OCH _Two 5-OEt OS H6.22 Me H 3-Cl SCH _Two 5-OEt OS H6.23 Me H 3-Cl OCH _Two 6-OEt OS H6.24 Me H 3-Cl SCH _Two 6-OEt OS H6.25 Me H 3-Cl OCH _Two 4-FOS H6.26 Me H 3-Cl SCH _Two 4-FOS H6.27 Me H 3-Cl OCH _Two 5-FOS H6.28 Me H 3-Cl SCH _Two 5-FOS H6.29 Me H 3-Cl OCH _Two 6-FOS H6.30 Me H 3-Cl SCH _Two 6-FOS H6.31 Me H 3-Cl OCH _Two 7-FOS H6.32 Me H 3-Cl SCH _Two 7-FOS H6.33 Me H 3-Cl OCH _Two 5-Cl OS H6.34 Me H 3-Cl SCH _Two 5-Cl OS H6.35 Me H 3-Cl OCH _Two 6-Cl OS H6.36 Me H 3-Cl SCH _Two 6-Cl OS H6.37 Me H 3-Cl OCH _Two 4-CF _Three OS H6.38 Me H 3-Cl SCH _Two 4-CF _Three OS H6.39 Me H 3-Cl OCH _Two 5-CF _Three OS H6.40 Me H 3-Cl SCH _Two 5-CF _Three OS H6.41 Me H 3-Cl OCH _Two 6-CF _Three OS H6.42 Me H 3-Cl SCH _Two 6-CF _Three OS H6.43 Me H 3-Cl OCH _Two 7-CF _Three OS H6.44 Me H 3-Cl SCH _Two 7-CF _Three OS H6.45 Me H 3-Cl OCH _Two 5-OCF _Three OS H6.46 Me H 3-Cl SCH _Two 5-OCF _Three OS H6.47 Me H 3-Cl OCH _Two 6-OCF _Three OS H6.48 Me H 3-Cl SCH _Two 6-OCF _Three OS H7.1 Me H 2,3-Me _Two OCH _Two 4-Me OS H7.2 Me H 2,3-Me _Two SCH _Two 4-Me OS H7.3 MeO H 2,3-Me _Two OCH _Two 4-Me OS H7.4 Me H 2,3-Me _Two OCH _Two 5-Me OS 260-261 H7.5 Me H 2,3-Me _Two SCH _Two 5-Me OS H7.6 MeO H 2,3-Me _Two OCH _Two 5-Me OS H7.7 Me H 2,3-Me _Two OCH _Two 5-Me OO H7.8 MeO H 2,3-Me _Two OCH _Two 5-Me OO H7.9 Me H 2,3-Me _Two OCH _Two 6-Me OS 224-226 H7.10 Me H 2,3-Me _Two SCH _Two 6-Me OS H7.11 MeO H 2,3-Me _Two OCH _Two 6-Me OS H7.12 Me H 2,3-Me _Two OCH _Two 7-Me OS H7.13 Me H 2,3-Me _Two SCH _Two 7-Me OS H7.14 MeO H 2,3-Me _Two OCH _Two 7-Me OS H7.15 Me H 2,3-Me _Two OCH _Two 4-OMe OS H7.16 Me H 2,3-Me _Two SCH _Two 4-OMe OS H7.17 MeO H 2,3-Me _Two OCH _Two 4-OMe OS H7.18 Me H 2,3-Me _Two OCH _Two 5-OMe OS 224-225 H7.19 Me H 2,3-Me _Two SCH _Two 5-OMe OS H7.20 MeO H 2,3-Me _Two OCH _Two 5-OMe OS H7.21 Me H 2,3-Me _Two OCH _Two 6-OMe OS 229-232 H7.22 Me H 2,3-Me _Two SCH _Two 6-OMe OS H7.23 MeO H 2,3-Me _Two OCH _Two 6-OMe OS H7.24 Me H 2,3-Me _Two OCH _Two 6-OMe OO H7.25 MeO H 2,3-Me _Two OCH _Two 6-OMe OO H7.26 Me H 2,3-Me _Two OCH _Two 7-OMe OS H7.27 Me H 2,3-Me _Two SCH _Two 7-OMe OS H7.28 MeO H 2,3-Me _Two OCH _Two 7-OMe OS H7.29 Me H 2,3-Me _Two OCH _Two 5-OEt OS H7.30 Me H 2,3-Me _Two SCH _Two 5-OEt OS H7.31 Me H 2,3-Me _Two OCH _Two 6-OEt OS H7.32 Me H 2,3-Me _Two SCH _Two 6-OEt OS H7.33 Me H 2,3-Me _Two OCH _Two 4-FOS H7.34 Me H 2,3-Me _Two SCH _Two 4-FOS H7.35 MeO H 2,3-Me _Two OCH _Two 4-FOS H7.36 Me H 2,3-Me _Two OCH _Two 5-FOS 245-246 H7.37 Me H 2,3-Me _Two SCH _Two 5-FOS H7.38 MeO H 2,3-Me _Two OCH _Two 5-FOS H7.39 Me H 2,3-Me _Two OCH _Two 5-FOO H7.40 MeO H 2,3-Me _Two OCH _Two 5-FOO H7.41 Me H 2,3-Me _Two OCH _Two 6-FOS 245-247 H7.42 Me H 2,3-Me _Two SCH _Two 6-FOS H7.43 MeO H 2,3-Me _Two OCH _Two 6-FOS H7.44 Me H 2,3-Me _Two OCH _Two 6-FOO H7.45 MeO H 2,3-Me _Two OCH _Two 6-FOO H7.46 Me H 2,3-Me _Two OCH _Two 7-FOS H7.47 Me H 2,3-Me _Two SCH _Two 7-FOS H7.48 MeO H 2,3-Me _Two OCH _Two 7-FOS H7.49 Me H 2,3-Me _Two OCH _Two 5-Cl OS 246-250 H7.50 Me H 2,3-Me _Two SCH _Two 5-Cl OS H7.51 MeO H 2,3-Me _Two OCH _Two 5-Cl OS H7.52 Me H 2,3-Me _Two OCH _Two 6-Cl OS H7.53 Me H 2,3-Me _Two SCH _Two 6-Cl OS H7.54 MeO H 2,3-Me _Two OCH _Two 6-Cl OS H7.55 Me H 2,3-Me _Two OCH _Two 5-Et OS H7.56 Me H 2,3-Me _Two SCH _Two 5-Et OS H7.57 MeO H 2,3-Me _Two OCH _Two 5-Et OS H7.58 Me H 2,3-Me _Two OCH _Two 6-Et OS H7.59 Me H 2,3-Me _Two SCH _Two 6-Et OS H7.60 MeO H 2,3-Me _Two OCH _Two 6-Et OS H7.61 Me H 2,3-Me _Two OCH _Two 4-CF _Three OS H7.62 Me H 2,3-Me _Two SCH _Two 4-CF _Three OS H7.63 Me H 2,3-Me _Two OCH _Two 5-CF _Three OS 262-263 H7.64 Me H 2,3-Me _Two SCH _Two 5-CF _Three OS H7.65 MeO H 2,3-Me _Two OCH _Two 5-CF _Three OS H7.66 Me H 2,3-Me _Two OCH _Two 6-CF _Three OS H7.67 Me H 2,3-Me _Two SCH _Two 6-CF _Three OS H7.68 MeO H 2,3-Me _Two OCH _Two 6-CF _Three OS H7.69 Me H 2,3-Me _Two OCH _Two 7-CF _Three OS H7.70 Me H 2,3-Me _Two SCH _Two 7-CF _Three OS H7.71 Me H 2,3-Me _Two OCH _Two 5-OCF _Three OS H7.72 Me H 2,3-Me _Two SCH _Two 5-OCF _Three OS H7.73 Me H 2,3-Me _Two OCH _Two 6-OCF _Three OS H7.74 Me H 2,3-Me _Two SCH _Two 6-OCF _Three OS H7.75 Me H 2,3-Me _Two OCH _Two 4,5-Me _Two OS H7.76 Me H 2,3-Me _Two SCH _Two 4,5-Me _Two OS H7.77 MeO H 2,3-Me _Two OCH _Two 4,5-Me _Two OS H7.78 Me H 2,3-Me _Two OCH _Two 4,6-Me _Two OS H7.79 Me H 2,3-Me _Two SCH _Two 4,6-Me _Two OS H7.80 Me H 2,3-Me _Two OCH _Two 4,7-Me _Two OS H7.81 Me H 2,3-Me _Two SCH _Two 4,7-Me _Two OS H7.82 Me H 2,3-Me _Two OCH _Two 5,6-Me _Two OS H7.83 Me H 2,3-Me _Two SCH _Two 5,6-Me _Two OS H7.84 Me H 2,3-Me _Two OCH _Two 5,7-Me _Two OS H7.85 Me H 2,3-Me _Two SCH _Two 5,7-Me _Two OS H7.86 Me H 2,3-Me _Two OCH _Two 6,7-Me _Two OS H7.87 Me H 2,3-Me _Two SCH _Two 6,7-Me _Two OS H7.88 Me H 2,3-Me _Two OCH _Two 4,5- (OMe) _Two OS H7.89 Me H 2,3-Me _Two SCH _Two 4,5- (OMe) _Two OS H7.90 Me H 2,3-Me _Two OCH _Two 4,6- (OMe) _Two OS H7.91 Me H 2,3-Me _Two SCH _Two 4,6- (OMe) _Two OS H7.92 Me H 2,3-Me _Two OCH _Two 4,7- (OMe) _Two OS H7.93 Me H 2,3-Me _Two SCH _Two 4,7- (OMe) _Two OS H7.94 Me H 2,3-Me _Two OCH _Two 5,6- (OMe) _Two OS H7.95 Me H 2,3-Me _Two SCH _Two 5,6- (OMe) _Two OS H7.96 Me H 2,3-Me _Two OCH _Two 5,7- (OMe) _Two OS H7.97 Me H 2,3-Me _Two SCH _Two 5,7- (OMe) _Two OS H7.98 Me H 2,3-Me _Two OCH _Two 6,7- (OMe) _Two OS H7.99 Me H 2,3-Me _Two SCH _Two 6,7- (OMe) _Two OS H7.100 Me H 2,3-Me _Two OCH _Two 4,5-F _Two OS H7.101 Me H 2,3-Me _Two SCH _Two 4,5-F _Two OS H7.102 Me H 2,3-Me _Two OCH _Two 4,6-F _Two OS H7.103 Me H 2,3-Me _Two SCH _Two 4,6-F _Two OS H7.104 Me H 2,3-Me _Two OCH _Two 4,7-F _Two OS H7.105 Me H 2,3-Me _Two SCH _Two 4,7-F _Two OS H7.106 Me H 2,3-Me _Two OCH _Two 5,6-F _Two OS 248-249 H7.107 Me H 2,3-Me _Two SCH _Two 5,6-F _Two OS H7.108 MeO H 2,3-Me _Two OCH _Two 5,6-F _Two OS H7.109 Me H 2,3-Me _Two OCH _Two 5,7-F _Two OS H7.110 Me H 2,3-Me _Two SCH _Two 5,7-F _Two OS H7.111 Me H 2,3-Me _Two OCH _Two 6,7-F _Two OS H7.112 Me H 2,3-Me _Two SCH _Two 6,7-F _Two OS H8.1 Me H 2,3-Me _Two OCH _Two 4,5-Cl _Two OS H8.2 Me H 2,3-Me _Two SCH _Two 4,5-Cl _Two OS H8.3 Me H 2,3-Me _Two OCH _Two 4,6-Cl _Two OS H8.4 Me H 2,3-Me _Two SCH _Two 4,6-Cl _Two OS H8.5 Me H 2,3-Me _Two OCH _Two 4,7-Cl _Two OS H8.6 Me H 2,3-Me _Two SCH _Two 4,7-Cl _Two OS H8.7 Me H 2,3-Me _Two OCH _Two 5,6-Cl _Two OS H8.8 Me H 2,3-Me _Two SCH _Two 5,6-Cl _Two OS H8.9 MeO H 2,3-Me _Two OCH _Two 5,6-Cl _Two OS H8.10 Me H 2,3-Me _Two OCH _Two 5,7-Cl _Two OS H8.11 Me H 2,3-Me _Two SCH _Two 5,7-Cl _Two OS H8.12 Me H 2,3-Me _Two OCH _Two 6,7-Cl _Two OS H8.13 Me H 2,3-Me _Two SCH _Two 6,7-Cl _Two OS H8.14 Me H 2,3-Me _Two OCH _Two 4,5- (CF _Three ) _Two OS H8.15 Me H 2,3-Me _Two SCH _Two 4,5- (CF _Three ) _Two OS H8.16 Me H 2,3-Me _Two OCH _Two 4,6- (CF _Three ) _Two OS H8.17 Me H 2,3-Me _Two SCH _Two 4,6- (CF _Three ) _Two OS H8.18 Me H 2,3-Me _Two OCH _Two 4,7- (CF _Three ) _Two OS H8.19 Me H 2,3-Me _Two SCH _Two 4,7- (CF _Three ) _Two OS H8.20 Me H 2,3-Me _Two OCH _Two 5,6- (CF _Three ) _Two OS H8.21 Me H 2,3-Me _Two SCH _Two 5,6- (CF _Three ) _Two OS H8.22 Me H 2,3-Me _Two OCH _Two 5,7- (CF _Three ) _Two OS H8.23 Me H 2,3-Me _Two SCH _Two 5,7- (CF _Three ) _Two OS H8.24 Me H 2,3-Me _Two OCH _Two 6,7- (CF _Three ) _Two OS H8.25 Me H 2,3-Me _Two SCH _Two 6,7- (CF _Three ) _Two OS H8.26 Me H 2,3-Me _Two OCH _Two 4-F, 5-Me OS H8.27 Me H 2,3-Me _Two SCH _Two 4-F, 5-Me OS H8.28 Me H 2,3-Me _Two OCH _Two 4-F, 6-Me OS H8.29 Me H 2,3-Me _Two SCH _Two 4-F, 6-Me OS H8.30 MeO H 2,3-Me _Two OCH _Two 4-F, 6-Me OS H8.31 Me H 2,3-Me _Two OCH _Two 4-F, 7-Me OS H8.32 Me H 2,3-Me _Two SCH _Two 4-F, 7-Me OS H8.33 Me H 2,3-Me _Two OCH _Two 4-Me, 5-FOS H8.34 Me H 2,3-Me _Two SCH _Two 4-Me, 5-FOS H8.35 Me H 2,3-Me _Two OCH _Two 5-F, 6-Me OS H8.36 Me H 2,3-Me _Two SCH _Two 5-F, 6-Me OS H8.37 Me H 2,3-Me _Two OCH _Two 5-F, 7-Me OS H8.38 Me H 2,3-Me _Two SCH _Two 5-F, 7-Me OS H8.39 Me H 2,3-Me _Two OCH _Two 4-Me, 6-FOS H8.40 Me H 2,3-Me _Two SCH _Two 4-Me, 6-FOS H8.41 Me H 2,3-Me _Two OCH _Two 5-Me, 6-FOS H8.42 Me H 2,3-Me _Two SCH _Two 5-Me, 6-FOS H8.43 Me H 2,3-Me _Two OCH _Two 6-F, 7-Me OS H8.44 Me H 2,3-Me _Two SCH _Two 6-F, 7-Me OS H8.45 Me H 2,3-Me _Two OCH _Two 4-Me, 7-FOS H8.46 Me H 2,3-Me _Two SCH _Two 4-Me, 7-FOS H8.47 Me H 2,3-Me _Two OCH _Two 5-Me, 7-FOS H8.48 Me H 2,3-Me _Two SCH _Two 5-Me, 7-FOS H8.49 Me H 2,3-Me _Two OCH _Two 6-Me, 7-FOS H8.50 Me H 2,3-Me _Two SCH _Two 6-Me, 7-FOS H8.51 Me H 2,3-Me _Two OCH _Two 4-Cl, 5-Me OS H8.52 Me H 2,3-Me _Two SCH _Two 4-Cl, 5-Me OS H8.53 Me H 2,3-Me _Two OCH _Two 4-Cl, 6-Me OS H8.54 Me H 2,3-Me _Two SCH _Two 4-Cl, 6-Me OS H8.55 MeO H 2,3-Me _Two OCH _Two 4-Cl, 6-Me OS H8.56 Me H 2,3-Me _Two OCH _Two 4-Cl, 7-Me OS H8.57 Me H 2,3-Me _Two SCH _Two 4-Cl, 7-Me OS H8.58 Me H 2,3-Me _Two OCH _Two 4-Me, 5-Cl OS H8.59 Me H 2,3-Me _Two SCH _Two 4-Me, 5-Cl OS H8.60 Me H 2,3-Me _Two OCH _Two 5-Cl, 6-Me OS H8.61 Me H 2,3-Me _Two SCH _Two 5-Cl, 6-Me OS H8.62 Me H 2,3-Me _Two OCH _Two 5-Cl, 7-Me OS H8.63 Me H 2,3-Me _Two SCH _Two 5-Cl, 7-Me OS H8.64 Me H 2,3-Me _Two OCH _Two 4-Me, 6-Cl OS H8.65 Me H 2,3-Me _Two SCH _Two 4-Me, 6-Cl OS H8.66 Me H 2,3-Me _Two OCH _Two 5-Me, 6-Cl OS H8.67 Me H 2,3-Me _Two SCH _Two 5-Me, 6-Cl OS H8.68 Me H 2,3-Me _Two OCH _Two 6-Cl, 7-Me OS H8.69 Me H 2,3-Me _Two SCH _Two 6-Cl, 7-Me OS H8.70 Me H 2,3-Me _Two OCH _Two 4-Me, 7-Cl OS H8.71 Me H 2,3-Me _Two SCH _Two 4-Me, 7-Cl OS H8.72 Me H 2,3-Me _Two OCH _Two 5-Me, 7-Cl OS H8.73 Me H 2,3-Me _Two SCH _Two 5-Me, 7-Cl OS H8.74 Me H 2,3-Me _Two OCH _Two 6-Me, 7-Cl OS H8.75 Me H 2,3-Me _Two SCH _Two 6-Me, 7-Cl OS H8.76 Me H 2,3-Me _Two OCH _Two 4-Cl, 5-FOS H8.77 Me H 2,3-Me _Two SCH _Two 4-Cl, 5-FOS H8.78 MeO H 2,3-Me _Two OCH _Two 4-Cl, 5-FOS H8.79 Me H 2,3-Me _Two OCH _Two 4-Cl, 6-FOS H8.80 Me H 2,3-Me _Two SCH _Two 4-Cl, 6-FOS H8.81 Me H 2,3-Me _Two OCH _Two 4-Cl, 7-FOS H8.82 Me H 2,3-Me _Two SCH _Two 4-Cl, 7-FOS H8.83 Me H 2,3-Me _Two OCH _Two 4-F, 5-Cl OS H8.84 Me H 2,3-Me _Two SCH _Two 4-F, 5-Cl OS H8.85 Me H 2,3-Me _Two OCH _Two 5-Cl, 6-FOS H8.86 Me H 2,3-Me _Two SCH _Two 5-Cl, 6-FOS H8.87 Me H 2,3-Me _Two OCH _Two 5-Cl, 7-FOS H8.88 Me H 2,3-Me _Two SCH _Two 5-Cl, 7-FOS H8.89 Me H 2,3-Me _Two OCH _Two 4-F, 6-Cl OS H8.90 Me H 2,3-Me _Two SCH _Two 4-F, 6-Cl OS H8.91 Me H 2,3-Me _Two OCH _Two 5-F, 6-Cl OS H8.92 Me H 2,3-Me _Two SCH _Two 5-F, 6-Cl OS H8.93 Me H 2,3-Me _Two OCH _Two 6-Cl, 7-FOS H8.94 Me H 2,3-Me _Two SCH _Two 6-Cl, 7-FOS H8.95 Me H 2,3-Me _Two OCH _Two 4-F, 7-Cl OS H8.96 Me H 2,3-Me _Two SCH _Two 4-F, 7-Cl OS H8.97 Me H 2,3-Me _Two OCH _Two 5-F, 7-Cl OS H8.98 Me H 2,3-Me _Two SCH _Two 5-F, 7-Cl OS H8.99 Me H 2,3-Me _Two OCH _Two 6-F, 7-Cl OS H8.100 Me H 2,3-Me _Two SCH _Two 6-F, 7-Cl OS H8.101 MeO H 2,5-Me _Two OCH _Two 5-FOS H8.102 MeO H 2,5-Me _Two OCH _Two 5-FOO H8.103 MeO H 2,6-Me _Two OCH _Two 5-FOS H8.104 MeO H 2,6-Me _Two OCH _Two 5-FOO H8.105 MeO H 3,5-Me _Two OCH _Two 5-FOS H8.106 MeO H 3,5-Me _Two OCH _Two 5-FOO H9.1 Me H 2,3-F _Two OCH _Two 4-Me OS H9.2 Me H 2,3-F _Two SCH _Two 4-Me OS H9.3 Me H 2,3-F _Two OCH _Two 5-Me OS H9.4 Me H 2,3-F _Two SCH _Two 5-Me OS H9.5 Me H 2,3-F _Two OCH _Two 6-Me OS H9.6 Me H 2,3-F _Two SCH _Two 6-Me OS H9.7 Me H 2,3-F _Two OCH _Two 7-Me OS H9.8 Me H 2,3-F _Two SCH _Two 7-Me OS H9.10 Me H 2,3-F _Two OCH _Two 5-Et OS H9.11 Me H 2,3-F _Two SCH _Two 5-Et OS H9.12 Me H 2,3-F _Two OCH _Two 6-Et OS H9.13 Me H 2,3-F _Two SCH _Two 6-Et OS H9.14 Me H 2,3-F _Two OCH _Two 4-OMe OS H9.15 Me H 2,3-F _Two SCH _Two 4-OMe OS H9.16 Me H 2,3-F _Two OCH _Two 5-OMe OS H9.17 Me H 2,3-F _Two SCH _Two 5-OMe OS H9.18 Me H 2,3-F _Two OCH _Two 6-OMe OS H9.19 Me H 2,3-F _Two SCH _Two 6-OMe OS H9.20 Me H 2,3-F _Two OCH _Two 7-OMe OS H9.21 Me H 2,3-F _Two SCH _Two 7-OMe OS H9.22 Me H 2,3-F _Two OCH _Two 5-OEt OS H9.23 Me H 2,3-F _Two SCH _Two 5-OEt OS H9.24 Me H 2,3-F _Two OCH _Two 6-OEt OS H9.25 Me H 2,3-F _Two SCH _Two 6-OEt OS H9.26 Me H 2,3-F _Two OCH _Two 4-FOS H9.27 Me H 2,3-F _Two SCH _Two 4-FOS H9.28 Me H 2,3-F _Two OCH _Two 5-FOS H9.29 Me H 2,3-F _Two SCH _Two 5-FOS H9.30 Me H 2,3-F _Two OCH _Two 6-FOS H9.31 Me H 2,3-F _Two SCH _Two 6-FOS H9.32 Me H 2,3-F _Two OCH _Two 7-FOS H9.34 Me H 2,3-F _Two SCH _Two 7-FOS H9.35 Me H 2,3-F _Two OCH _Two 5-Cl OS H9.36 Me H 2,3-F _Two SCH _Two 5-Cl OS H9.37 Me H 2,3-F _Two OCH _Two 6-Cl OS H9.38 Me H 2,3-F _Two SCH _Two 6-Cl OS H9.39 Me H 2,3-F _Two OCH _Two 4-CF _Three OS H9.40 Me H 2,3-F _Two SCH _Two 4-CF _Three OS H9.41 Me H 2,3-F _Two OCH _Two 5-CF _Three OS H9.42 Me H 2,3-F _Two SCH _Two 5-CF _Three OS H9.43 Me H 2,3-F _Two OCH _Two 6-CF _Three OS H9.44 Me H 2,3-F _Two SCH _Two 6-CF _Three OS H9.45 Me H 2,3-F _Two OCH _Two 7-CF _Three OS H9.46 Me H 2,3-F _Two SCH _Two 7-CF _Three OS H9.47 Me H 2,3-F _Two OCH _Two 5-OCF _Three OS H9.48 Me H 2,3-F _Two SCH _Two 5-OCF _Three OS H9.49 Me H 2,3-F _Two OCH _Two 6-OCF _Three OS H9.50 Me H 2,3-F _Two SCH _Two 6-OCF _Three OS H9.51 Me H 2,3-F _Two OCH _Two 4,5-Me _Two OS H9.52 Me H 2,3-F _Two SCH _Two 4,5-Me _Two OS H9.53 Me H 2,3-F _Two OCH _Two 4,6-Me _Two OS H9.54 Me H 2,3-F _Two SCH _Two 4,6-Me _Two OS H9.55 Me H 2,3-F _Two OCH _Two 4,7-Me _Two OS H9.56 Me H 2,3-F _Two SCH _Two 4,7-Me _Two OS H9.57 Me H 2,3-F _Two OCH _Two 5,6-Me _Two OS H9.58 Me H 2,3-F _Two SCH _Two 5,6-Me _Two OS H9.60 Me H 2,3-F _Two OCH _Two 5,7-Me _Two OS H9.61 Me H 2,3-F _Two SCH _Two 5,7-Me _Two OS H9.62 Me H 2,3-F _Two OCH _Two 6,7-Me _Two OS H9.63 Me H 2,3-F _Two SCH _Two 6,7-Me _Two OS H9.64 Me H 2,3-F _Two OCH _Two 4,5- (OMe) _Two OS H9.65 Me H 2,3-F _Two SCH _Two 4,5- (OMe) _Two OS H9.66 Me H 2,3-F _Two OCH _Two 4,6- (OMe) _Two OS H9.67 Me H 2,3-F _Two SCH _Two 4,6- (OMe) _Two OS H9.68 Me H 2,3-F _Two OCH _Two 4,7- (OMe) _Two OS H9.69 Me H 2,3-F _Two SCH _Two 4,7- (OMe) _Two OS H9.70 Me H 2,3-F _Two OCH _Two 5,6- (OMe) _Two OS H9.71 Me H 2,3-F _Two SCH _Two 5,6- (OMe) _Two OS H9.72 Me H 2,3-F _Two OCH _Two 5,7- (OMe) _Two OS H9.73 Me H 2,3-F _Two SCH _Two 5,7- (OMe) _Two OS H9.74 Me H 2,3-F _Two OCH _Two 6,7- (OMe) _Two OS H9.75 Me H 2,3-F _Two SCH _Two 6,7- (OMe) _Two OS H9.76 Me H 2,3-F _Two OCH _Two 4,5-F _Two OS H9.77 Me H 2,3-F _Two SCH _Two 4,5-F _Two OS H9.78 Me H 2,3-F _Two OCH _Two 4,6-F _Two OS H9.79 Me H 2,3-F _Two SCH _Two 4,6-F _Two OS H9.80 Me H 2,3-F _Two OCH _Two 4,7-F _Two OS H9.81 Me H 2,3-F _Two SCH _Two 4,7-F _Two OS H9.82 Me H 2,3-F _Two OCH _Two 5,6-F _Two OS H9.83 Me H 2,3-F _Two SCH _Two 5,6-F _Two OS H9.84 Me H 2,3-F _Two OCH _Two 5,7-F _Two OS H9.85 Me H 2,3-F _Two SCH _Two 5,7-F _Two OS H9.86 Me H 2,3-F _Two OCH _Two 6,7-F _Two OS H9.87 Me H 2,3-F _Two SCH _Two 6,7-F _Two OS H9.88 Me H 2,3-F _Two OCH _Two 4,5-Cl _Two OS H9.89 Me H 2,3-F _Two SCH _Two 4,5-Cl _Two OS H9.90 Me H 2,3-F _Two OCH _Two 4,6-Cl _Two OS H9.91 Me H 2,3-F _Two SCH _Two 4,6-Cl _Two OS H9.92 Me H 2,3-F _Two OCH _Two 4,7-Cl _Two OS H9.93 Me H 2,3-F _Two SCH _Two 4,7-Cl _Two OS H9.94 Me H 2,3-F _Two OCH _Two 5,6-Cl _Two OS H9.95 Me H 2,3-F _Two SCH _Two 5,6-Cl _Two OS H9.96 Me H 2,3-F _Two OCH _Two 5,7-Cl _Two OS H9.97 Me H 2,3-F _Two SCH _Two 5,7-Cl _Two OS H9.98 Me H 2,3-F _Two OCH _Two 6,7-Cl _Two OS H9.99 Me H 2,3-F _Two SCH _Two 6,7-Cl _Two OS H9.100 Me H 2,3-F _Two OCH _Two 4,5- (CF _Three ) _Two OS H9.101 Me H 2,3-F _Two SCH _Two 4,5- (CF _Three ) _Two OS H9.102 Me H 2,3-F _Two OCH _Two 4,6- (CF _Three ) _Two OS H9.103 Me H 2,3-F _Two SCH _Two 4,6- (CF _Three ) _Two OS H9.104 Me H 2,3-F _Two OCH _Two 4,7- (CF _Three ) _Two OS H9.105 Me H 2,3-F _Two SCH _Two 4,7- (CF _Three ) _Two OS H9.106 Me H 2,3-F _Two OCH _Two 5,6- (CF _Three ) _Two OS H9.107 Me H 2,3-F _Two SCH _Two 5,6- (CF _Three ) _Two OS H9.108 Me H 2,3-F _Two OCH _Two 5,7- (CF _Three ) _Two OS H9.109 Me H 2,3-F _Two SCH _Two 5,7- (CF _Three ) _Two OS H9.110 Me H 2,3-F _Two OCH _Two 6,7- (CF _Three ) _Two OS H9.111 Me H 2,3-F _Two SCH _Two 6,7- (CF _Three ) _Two OS H10.1 Me H 2,3-F _Two OCH _Two 4-F, 5-Me OS H10.2 Me H 2,3-F _Two SCH _Two 4-F, 5-Me OS H10.3 Me H 2,3-F _Two OCH _Two 4-F, 6-Me OS H10.4 Me H 2,3-F _Two SCH _Two 4-F, 6-Me OS H10.5 Me H 2,3-F _Two OCH _Two 4-F, 7-Me OS H10.6 Me H 2,3-F _Two SCH _Two 4-F, 7-Me OS H10.7 Me H 2,3-F _Two OCH _Two 4-Me, 5-FOS H10.8 Me H 2,3-F _Two SCH _Two 4-Me, 5-FOS H10.9 Me H 2,3-F _Two OCH _Two 5-F, 6-Me OS H10.10 Me H 2,3-F _Two SCH _Two 5-F, 6-Me OS H10.11 Me H 2,3-F _Two OCH _Two 5-F, 7-Me OS H10.12 Me H 2,3-F _Two SCH _Two 5-F, 7-Me OS H10.13 Me H 2,3-F _Two OCH _Two 4-Me, 6-FOS H10.14 Me H 2,3-F _Two SCH _Two 4-Me, 6-FOS H10.15 Me H 2,3-F _Two OCH _Two 5-Me, 6-FOS H10.16 Me H 2,3-F _Two SCH _Two 5-Me, 6-FOS H10.17 Me H 2,3-F _Two OCH _Two 6-F, 7-Me OS H10.18 Me H 2,3-F _Two SCH _Two 6-F, 7-Me OS H10.19 Me H 2,3-F _Two OCH _Two 4-Me, 7-FOS H10.20 Me H 2,3-F _Two SCH _Two 4-Me, 7-FOS H10.21 Me H 2,3-F _Two OCH _Two 5-Me, 7-FOS H10.22 Me H 2,3-F _Two SCH _Two 5-Me, 7-FOS H10.23 Me H 2,3-F _Two OCH _Two 6-Me, 7-FOS H10.24 Me H 2,3-F _Two SCH _Two 6-Me, 7-FOS H10.25 Me H 2,3-F _Two OCH _Two 4-Cl, 5-Me OS H10.26 Me H 2,3-F _Two SCH _Two 4-Cl, 5-Me OS H10.27 Me H 2,3-F _Two OCH _Two 4-Cl, 6-Me OS H10.28 Me H 2,3-F _Two SCH _Two 4-Cl, 6-Me OS H10.29 Me H 2,3-F _Two OCH _Two 4-Cl, 7-Me OS H10.30 Me H 2,3-F _Two SCH _Two 4-Cl, 7-Me OS H10.31 Me H 2,3-F _Two OCH _Two 4-Me, 5-Cl OS H10.32 Me H 2,3-F _Two SCH _Two 4-Me, 5-Cl OS H10.33 Me H 2,3-F _Two OCH _Two 5-Cl, 6-Me OS H10.34 Me H 2,3-F _Two SCH _Two 5-Cl, 6-Me OS H10.35 Me H 2,3-F _Two OCH _Two 5-Cl, 7-Me OS H10.36 Me H 2,3-F _Two SCH _Two 5-Cl, 7-Me OS H10.37 Me H 2,3-F _Two OCH _Two 4-Me, 6-Cl OS H10.38 Me H 2,3-F _Two SCH _Two 4-Me, 6-Cl OS H10.39 Me H 2,3-F _Two OCH _Two 6-Cl, 5-Me OS H10.40 Me H 2,3-F _Two SCH _Two 6-Cl, 5-Me OS H10.41 Me H 2,3-F _Two OCH _Two 6-Cl, 7-Me OS H10.42 Me H 2,3-F _Two SCH _Two 6-Cl, 7-Me OS H10.43 Me H 2,3-F _Two OCH _Two 4-Me, 7-Cl OS H10.44 Me H 2,3-F _Two SCH _Two 4-Me, 7-Cl OS H10.45 Me H 2,3-F _Two OCH _Two 5-Me, 7-Cl OS H10.46 Me H 2,3-F _Two SCH _Two 5-Me, 7-Cl OS H10.47 Me H 2,3-F _Two OCH _Two 6-Me, 7-Cl OS H10.48 Me H 2,3-F _Two SCH _Two 6-Me, 7-Cl OS H10.49 Me H 2,3-F _Two OCH _Two 4-Cl, 5-FOS H10.50 Me H 2,3-F _Two SCH _Two 4-Cl, 5-FOS H10.51 Me H 2,3-F _Two OCH _Two 4-Cl, 6-FOS H10.52 Me H 2,3-F _Two SCH _Two 4-Cl, 6-FOS H10.53 Me H 2,3-F _Two OCH _Two 4-Cl, 7-FOS H10.54 Me H 2,3-F _Two SCH _Two 4-Cl, 7-FOS H10.55 Me H 2,3-F _Two OCH _Two 4-F, 5-Cl OS H10.56 Me H 2,3-F _Two SCH _Two 4-F, 5-Cl OS H10.57 Me H 2,3-F _Two OCH _Two 5-Cl, 6-FOS H10.58 Me H 2,3-F _Two SCH _Two 5-Cl, 6-FOS H10.59 Me H 2,3-F _Two OCH _Two 5-Cl, 7-FOS H10.60 Me H 2,3-F _Two SCH _Two 5-Cl, 7-FOS H10.61 Me H 2,3-F _Two OCH _Two 4-F, 6-Cl OS H10.62 Me H 2,3-F _Two SCH _Two 4-F, 6-Cl OS H10.63 Me H 2,3-F _Two OCH _Two 5-F, 6-Cl OS H10.64 Me H 2,3-F _Two SCH _Two 5-F, 6-Cl OS H10.65 Me H 2,3-F _Two OCH _Two 7-F, 6-Cl OS H10.66 Me H 2,3-F _Two SCH _Two 7-F, 6-Cl OS H10.67 Me H 2,3-F _Two OCH _Two 4-F, 7-Cl OS H10.68 Me H 2,3-F _Two SCH _Two 4-F, 7-Cl OS H10.69 Me H 2,3-F _Two OCH _Two 5-F, 7-Cl OS H10.70 Me H 2,3-F _Two SCH _Two 5-F, 7-Cl OS H10.71 Me H 2,3-F _Two OCH _Two 6-F, 7-Cl OS H10.72 Me H 2,3-F _Two SCH _Two 6-F, 7-Cl OS H11.1 Me H 2,3- (OMe) _Two OCH _Two 4-Me OS H11.2 Me H 2,3- (OMe) _Two SCH _Two 4-Me OS H11.3 Me H 2,3- (OMe) _Two OCH _Two 5-Me OS H11.4 Me H 2,3- (OMe) _Two SCH _Two 5-Me OS H11.5 Me H 2,3- (OMe) _Two OCH _Two 6-Me OS H11.6 Me H 2,3- (OMe) _Two SCH _Two 6-Me OS H11.7 Me H 2,3- (OMe) _Two OCH _Two 7-Me OS H11.8 Me H 2,3- (OMe) _Two SCH _Two 7-Me OS H11.9 Me H 2,3- (OMe) _Two OCH _Two 5-Et OS H11.10 Me H 2,3- (OMe) _Two SCH _Two 5-Et OS H11.11 Me H 2,3- (OMe) _Two OCH _Two 6-Et OS H11.12 Me H 2,3- (OMe) _Two SCH _Two 6-Et OS H11.13 Me H 2,3- (OMe) _Two OCH _Two 4-OMe OS H11.14 Me H 2,3- (OMe) _Two SCH _Two 4-OMe OS H11.15 Me H 2,3- (OMe) _Two OCH _Two 5-OMe OS H11.16 Me H 2,3- (OMe) _Two SCH _Two 5-OMe OS H11.17 Me H 2,3- (OMe) _Two OCH _Two 6-OMe OS H11.18 Me H 2,3- (OMe) _Two SCH _Two 6-OMe OS H11.19 Me H 2,3- (OMe) _Two OCH _Two 7-OMe OS H11.20 Me H 2,3- (OMe) _Two SCH _Two 7-OMe OS H11.21 Me H 2,3- (OMe) _Two OCH _Two 5-OEt OS H11.22 Me H 2,3- (OMe) _Two SCH _Two 5-OEt OS H11.23 Me H 2,3- (OMe) _Two OCH _Two 6-OEt OS H11.24 Me H 2,3- (OMe) _Two SCH _Two 6-OEt OS H11.25 Me H 2,3- (OMe) _Two OCH _Two 4-FOS H11.26 Me H 2,3- (OMe) _Two SCH _Two 4-FOS H11.27 Me H 2,3- (OMe) _Two OCH _Two 5-FOS H11.28 Me H 2,3- (OMe) _Two SCH _Two 5-FOS H11.29 Me H 2,3- (OMe) _Two OCH _Two 6-FOS H11.31 Me H 2,3- (OMe) _Two OCH _Two 7-FOS H11.32 Me H 2,3- (OMe) _Two SCH _Two 7-FOS H11.33 Me H 2,3- (OMe) _Two OCH _Two 5-Cl OS H11.34 Me H 2,3- (OMe) _Two SCH _Two 5-Cl OS H11.35 Me H 2,3- (OMe) _Two OCH _Two 6-Cl OS H11.36 Me H 2,3- (OMe) _Two SCH _Two 6-Cl OS H11.37 Me H 2,3- (OMe) _Two OCH _Two 4-CF _Three OS H11.38 Me H 2,3- (OMe) _Two SCH _Two 4-CF _Three OS H11.39 Me H 2,3- (OMe) _Two OCH _Two 5-CF _Three OS H11.40 Me H 2,3- (OMe) _Two SCH _Two 5-CF _Three OS H11.41 Me H 2,3- (OMe) _Two OCH _Two 6-CF _Three OS H11.42 Me H 2,3- (OMe) _Two SCH _Two 6-CF _Three OS H11.43 Me H 2,3- (OMe) _Two OCH _Two 7-CF _Three OS H11.44 Me H 2,3- (OMe) _Two SCH _Two 7-CF _Three OS H11.45 Me H 2,3- (OMe) _Two OCH _Two 5-OCF _Three OS H11.46 Me H 2,3- (OMe) _Two SCH _Two 5-OCF _Three OS H11.47 Me H 2,3- (OMe) _Two OCH _Two 6-OCF _Three OS H11.48 Me H 2,3- (OMe) _Two SCH _Two 6-OCF _Three OS H11.49 MeO H 2,3-Cl _Two OCH _Two 5-FOS H11.50 MeO H 2,5-Cl _Two OCH _Two 5-FOS H11.51 MeO H 2,6-Cl _Two OCH _Two 5-FOS H11.52 MeO H 3,5-Cl _Two OCH _Two 5-FOS 中 Among the above exemplified compounds, preferred are , A1.1,
A1.2, A1.3, A1.5, A1.6, A1.7,
A1.8, A1.9, A1.13, A1.16, A1.
18, A1.21, A1.25, A1.28, A1.3
1, A1.32, A1.45, A1.56, A1.5
8, A1.60, A1.62, A1.65, A1.7
0, B1.1, B1.3, B1.5, B1.10, B
2.37, B2.63, C1.1, C1.2, C1.
3, C1.5, C1.6, C1.11, C1.13, C
1.17, C1.19, C1.23, C1.24, C
1.27, C1.28, C1.36, C1.42, C
1.44, C1.52, C1.55, C2.1, C2.
4, C2.19, C3.30, C3.32, C4.2
7, C4.29, C6.1, C6.29, C7.55,
C8.1, C8.2, C8.3, C8.6, C8.1
9, C8.20, C8.22, C8.23, C8.3
9, C8.72, C8.76, C9.1, C9.3, C
9.4, C9.6, C9.20, C9.22, C9.2
3, C9.24, C9.36, C9.38, C9.3
9, C9.40, C9.52, C9.54, C9.5
5, C9.56, C10.1, C10.3, C10.
4, C10.5, C10.17, C10.20, C1
0.42, C10.44, C10.46, C10.4
8, C10.49, C10.50, C10.62, C1
0.64, C10.65, C10.66, C10.7
8, C10.82, C10.84, C10.86, C1
0.88, C10.92, C10.94, C10.9
6, C10.98, C11.1, C11.4, C11.
17, C11.20, C11.33, C11.48, C
11.63, C11.64, C11.78, C11.7
9, C12.45, C12.47, C14.15, C1
4.18, C14.31, C14.45, C14.7
4, C15.37, C16.113, C16.126,
C18.118, C18.119, C18.130, D
1.1, D1.2, D1.4, D1.5, D1.8, D
1.10, D1.13, D1.14, D1.16, D
1.18, D1.35, D1.37, D1.40, D
1.43, D1.46, D1.47, D1.49, D
1.50, D1.51, D1.55, D1.56, D
1.57, D1.60, D1.62, D1.65, D
1.67, D1.68, D1.69, D1.70, D
1.71, D1.72, D1.74, D1.76, D
1.78, D1.79, D1.80, D1.81, D
1.82, D1.83, D1.85, D1.87, D
1.88, D1.90, D1.91, D1.92, D
1.93, D1.94, D1.95, D1.97, D
1.98, D1.99, D1.100, D1.101,
D1.102, D1.103, D1.104, D1.1
05, D1.106, D1.109, D1.110, D
1.112, D1.113, D1.114, D1.11
6, D1.117, D1.118, D1.119, D
1.122, D1.123, D1.125, D1.12
6, D1.128, D1.129, D1.130, D
1.131, D1.132, D1.135, D1.13
6, D2.1, D2.4, D2.5, D2.6, D2.
7, D2.9, D2.10, D2.11, D2.13,
D2.14, D2.15, D2.17, D2.19, D
2.20, D2.21, D2.22, D2.23, D
2.25, D2.26, D2.28, D2.29, D
2.30, D2.32, D2.40, D2.41, D
2.42, D2.44, D2.45, D2.46, D
2.47, D2.48, D2.50, D2.52, D
2.53, D2.54, D2.55, D2.56, D
2.57, D2.60, D2.61, D2.63, D
2.65, D2.66, D2.67, D2.68, D
2.72, D2.73, D2.74, D2.75, D
2.76, D2.77, D2.78, D2.79, D
2.80, D2.81, D2.82, D2.83, D
2.84, D2.85, E1.1, E1.3, E1.1
5, E1.17, E4.1, E6.1, E7.5, E
7.10, E7.131, E7.135, F1.1, F
1.3, F1.5, F1.11, F1.15, F1.2
1, F1.25, F1.31, F1.33, F1.6
9, F3.1, F3.3, F3.10, F3.14, F
3.20, F3.21, F3.22, F3.29, F
3.31, F3.56, F4.1, F4.11, F4.
12, F4.14, F4.16, F4.19, F4.2
0, F4.22, F4.23, F4.25, F4.2
7, F4.28, F4.30, F4.33, F4.4
0, F4.41, F4.43, F4.59, F4.6
1, F4.63, F4.69, F4.71, F4.7
9, F4.81, F4.103, F5.3, F5.9,
F5.13, F6.11, F6.12, F6.15, F
6.16, F6.19, F6.20, F6.23, F
6.24, F7.17, F7.34, F7.39, F
7.45, F7.56, F7.69, F7.92, F
7.99, F7.120, F7.136, F7.14
7, F7.169, F7.173, G1.3, G1.
4, G1.5, G1.6, G1.8, G1.9, G1.
10, G1.11, G1.13, G1.14, G1.1
5, G1.19, G1.20, G1.30, G1.3
2, G1.34, G1.35, G1.36, G1.3
7, G1.39, G1.44, G1.50, G1.5
2, G1.55, G1.57, G1.58, G1.5
9, G1.60, G1.62, G1.63, G1.6
4, G1.67, G1.68, G1.69, G1.7
2, G1.74, G1.76, G1.77, G1.8
1, G1.85, G1.87, G1.89, G1.9
2, G1.94, G1.95, G1.96, G1.9
7, G1.99, G1.109, G1.113, G1.
114, G1.117, G1.118, G1.121,
G1.122, G1.127, G1.128, G2.1
3, G2.14, G2.42, G2.49, G2.5
0, G2.61, G2.62, G2.86, G2.9
7, G2.115, G2.137, G2.148, G
2.166, G5.3, G5.6, G5.17, G5.
20, G5.33, G5.38, G5.45, G5.5
2, G6.31, G8.31, G8.33, G8.3
6, G8.38, G10.51, G10.57, G1
0.61, G10.63, H4.3, H4.8, H4.
19, H4.22, H4.35, H4.38, H4.4
3, H4.50, H4.91, H7.4, H7.9, H
7.18, H7.21, H7.36, H7.41, H
7.49, H7.63, H7.106
Wear.

【００５９】更に好適には、Ａ１．１、Ａ１．２、Ａ
１．５、Ａ１．６、Ａ１．７、Ａ１．９、Ａ１．１８、
Ａ１．２１、Ａ１．２５、Ａ１．２８、Ａ１．６２、Ａ
１．６５、Ａ１．７０、Ｂ１．１、Ｂ１．３、Ｂ１．
５、Ｂ１．１０、Ｂ２．６３、Ｃ１．１、Ｃ１．２、Ｃ
１．５、Ｃ１．６、Ｃ１．１７、Ｃ１．２３、Ｃ１．２
４、Ｃ１．３６、Ｃ１．４２、Ｃ１．４４、Ｃ１．５
２、Ｃ１．５５、Ｃ２．１、Ｃ２．４、Ｃ２．１９、Ｃ
３．３０、Ｃ３．３２、Ｃ８．１、Ｃ８．２、Ｃ８．
３、Ｃ８．６、Ｃ８．１９、Ｃ８．２０、Ｃ８．２２、
Ｃ８．２３、Ｃ８．３９、Ｃ９．１、Ｃ９．３、Ｃ９．
４、Ｃ９．６、Ｃ９．２０、Ｃ９．２２、Ｃ９．２３、
Ｃ９．２４、Ｃ９．３６、Ｃ９．３８、Ｃ９．３９、Ｃ
９．４０、Ｃ９．５２、Ｃ９．５４、Ｃ９．５５、Ｃ
９．５６、Ｃ１１．１、Ｄ１．１、Ｄ１．２、Ｄ１．
４、Ｄ１．５、Ｄ１．８、Ｄ１．１０、Ｄ１．４７、Ｄ
１．４９、Ｄ１．５０、Ｄ１．５１、Ｄ１．５５、Ｄ
１．６６、Ｄ１．６８、Ｄ１．７０、Ｄ１．７１、Ｄ
１．７２、Ｄ１．７４、Ｄ１．１０３、Ｄ１．１０５、
Ｄ１．１０６、Ｄ２．１、Ｄ２．４、Ｄ２．５、Ｄ２．
６、Ｄ２．７、Ｄ２．９、Ｄ２．１０、Ｄ２．１１、Ｄ
２．１９、Ｄ２．２０、Ｄ２．２６、Ｄ２．２８、Ｄ
２．３０、Ｄ２．４０、Ｄ２．６５、Ｄ２．７３、Ｄ
２．７４、Ｄ２．７５、Ｄ２．７６、Ｄ２．７７、Ｄ
２．７８、Ｄ２．７９、Ｄ２．８４、Ｅ１．１、Ｅ１．
１５、Ｆ１．１、Ｆ１．３、Ｆ１．５、Ｆ１．１１、Ｆ
１．１５、Ｆ１．２１、Ｆ１．２５、Ｆ１．３１、Ｆ
１．３３、Ｆ３．１、Ｆ３．３、Ｆ３．１０、Ｆ３．１
４、Ｆ３．２０、Ｆ３．２２、Ｆ３．２９、Ｆ３．３
１、Ｆ３．５６、Ｆ４．１、Ｆ４．１１、Ｆ４．１２、
Ｆ４．１４、Ｆ４．１９、Ｆ４．２０、Ｆ４．２２、Ｆ
４．２３、Ｆ４．２５、Ｆ４．２７、Ｆ４．２８、Ｆ
４．３０、Ｆ４．３３、Ｆ４．４０、Ｆ４．４１、Ｆ
４．４３、Ｆ４．５９、Ｆ４．６１、Ｆ４．６３、Ｆ
４．６９、Ｆ４．７１、Ｆ４．７９、Ｆ４．８１、Ｆ
４．１０３、Ｆ５．１３、Ｆ６．２４、Ｆ７．３４、Ｆ
７．３９、Ｆ７．４５、Ｆ７．５６、Ｇ１．３、Ｇ１．
４、Ｇ１．５、Ｇ１．６、Ｇ１．８、Ｇ１．９、Ｇ１．
１０、Ｇ１．１１、Ｇ１．１３、Ｇ１．１４、Ｇ１．１
５、Ｇ１．１９、Ｇ１．２０、Ｇ１．３０、Ｇ１．３
２、Ｇ１．３４、Ｇ１．３５、Ｇ１．３６、Ｇ１．３
７、Ｇ１．３９、Ｇ１．４４、Ｇ１．５０、Ｇ１．５
２、Ｇ１．５５、Ｇ１．５７、Ｇ１．５８、Ｇ１．５
９、Ｇ１．６０、Ｇ１．６２、Ｇ１．６３、Ｇ１．６
４、Ｇ１．６７、Ｇ１．６８、Ｇ１．６９、Ｇ１．７
２、Ｇ１．７４、Ｇ１．７６、Ｇ１．７７、Ｇ１．８
１、Ｇ１．８５、Ｇ１．９２、Ｇ２．５、Ｇ２．４２、
Ｇ５．３、Ｇ５．６、Ｇ５．１７、Ｇ５．３３、Ｇ５．
３８、Ｇ５．４５、Ｇ６．３１、Ｇ８．３１、Ｇ８．３
３、Ｇ８．３６、Ｇ８．３８、Ｇ１０．５１、Ｈ４．
３、Ｈ４．８、Ｈ４．１９、Ｈ４．２２、Ｈ４．３５、
Ｈ４．３８、Ｈ４．４３、Ｈ４．９１、Ｈ７．３６を挙
げることができる。More preferably, A1.1, A1.2, A
1.5, A1.6, A1.7, A1.9, A1.18,
A1.21, A1.25, A1.28, A1.62, A
1.65, A1.70, B1.1, B1.3, B1.
5, B1.10, B2.63, C1.1, C1.2, C
1.5, C1.6, C1.17, C1.23, C1.2
4, C1.36, C1.42, C1.44, C1.5
2, C1.55, C2.1, C2.4, C2.19, C
3.30, C3.32, C8.1, C8.2, C8.
3, C8.6, C8.19, C8.20, C8.22,
C8.23, C8.39, C9.1, C9.3, C9.
4, C9.6, C9.20, C9.22, C9.23,
C9.24, C9.36, C9.38, C9.39, C
9.40, C9.52, C9.54, C9.55, C
9.56, C11.1, D1.1, D1.2, D1.
4, D1.5, D1.8, D1.10, D1.47, D
1.49, D1.50, D1.51, D1.55, D
1.66, D1.68, D1.70, D1.71, D
1.72, D1.74, D1.103, D1.105,
D1.106, D2.1, D2.4, D2.5, D2.
6, D2.7, D2.9, D2.10, D2.11, D
2.19, D2.20, D2.26, D2.28, D
2.30, D2.40, D2.65, D2.73, D
2.74, D2.75, D2.76, D2.77, D
2.78, D2.79, D2.84, E1.1, E1.
15, F1.1, F1.3, F1.5, F1.11, F
1.15, F1.21, F1.25, F1.31, F
1.33, F3.1, F3.3, F3.10, F3.1
4, F3.20, F3.22, F3.29, F3.3
1, F3.56, F4.1, F4.11, F4.12,
F4.14, F4.19, F4.20, F4.22, F
4.23, F4.25, F4.27, F4.28, F
4.30, F4.33, F4.40, F4.41, F
4.43, F4.59, F4.61, F4.63, F
4.69, F4.71, F4.79, F4.81, F
4.103, F5.13, F6.24, F7.34, F
7.39, F7.45, F7.56, G1.3, G1.
4, G1.5, G1.6, G1.8, G1.9, G1.
10, G1.11, G1.13, G1.14, G1.1
5, G1.19, G1.20, G1.30, G1.3
2, G1.34, G1.35, G1.36, G1.3
7, G1.39, G1.44, G1.50, G1.5
2, G1.55, G1.57, G1.58, G1.5
9, G1.60, G1.62, G1.63, G1.6
4, G1.67, G1.68, G1.69, G1.7
2, G1.74, G1.76, G1.77, G1.8
1, G1.85, G1.92, G2.5, G2.42,
G5.3, G5.6, G5.17, G5.33, G5.
38, G5.45, G6.31, G8.31, G8.3
3, G8.36, G8.38, G10.51, H4.
3, H4.8, H4.19, H4.22, H4.35,
H4.38, H4.43, H4.91 and H7.36 can be mentioned.

【００６０】より更に好適には、Ｃ１．１、Ｃ１．２、
Ｃ１．５、Ｃ１．６、Ｄ１．４７、Ｄ１．７０、Ｄ２．
４、Ｄ２．５、Ｄ２．７５、Ｄ２．７６、Ｄ２．８４、
Ｇ１．３２、Ｇ１．３４、Ｇ１．３５、Ｇ１．３６、Ｇ
１．３７、Ｇ１．３９、Ｇ１．５０、Ｇ１．５２、Ｇ
１．５５、Ｇ１．５７、Ｇ１．５８、Ｇ１．５９、Ｇ
１．６０、Ｇ１．６２、Ｇ１．６３、Ｇ１．６４、Ｇ
１．７２、Ｇ１．７４、Ｇ１．７６、Ｇ１．７７、Ｇ
１．８１を挙げることができる。Even more preferably, C1.1, C1.2,
C1.5, C1.6, D1.47, D1.70, D2.
4, D2.5, D2.75, D2.76, D2.84,
G1.32, G1.34, G1.35, G1.36, G
1.37, G1.39, G1.50, G1.52, G
1.55, G1.57, G1.58, G1.59, G
1.60, G1.62, G1.63, G1.64, G
1.72, G1.74, G1.76, G1.77, G
1.81 can be mentioned.

【００６１】最も好適には、Ｃ１．１Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］アセトアミド、Ｃ１．２Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−メチルフェニル］アセトアミド、Ｃ１．５メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］カルバマート、Ｃ１．６メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］カルバマート、Ｄ１．４７メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−ヒドロキシメチル
カルバマート、Ｄ１．７０メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−プロピオニルオキ
シメチルカルバマート、Ｄ２．４Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニルプロピ
オンアミド、Ｇ１．３９メチルＮ−［４−（６−メトキシベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト、Ｇ１．５７メチルＮ−［４−（５−フルオロベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト、Ｇ１．６２メチルＮ−［４−（６−フルオロベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
トを挙げることできる。Most preferably, C1.1 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] acetamide, C1.2 N- [4- (benzoxazol-2-ylmethoxy)
-2-methylphenyl] acetamide, C1.5 methyl N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] carbamate, C1.6 methyl N- [4- (benzoxazol-2-ylmethoxy) -2-methylphenyl] carbamate, D1.47 methyl N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] -N-hydroxymethylcarbamate, D1.70 methyl N- [4- (benzo Thiazol-2-ylmethoxy) -2-methylphenyl] -N-propionyloxymethylcarbamate, D2.4 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylpropionamide, G1.39 methyl N- [4- (6-methoxybenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamate, G1.57 methyl N- [4- (5-fluorobenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamate, G1.62 methyl N- [4- (6-fluorobenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamate.

【００６２】[0062]

【発明の実施の形態】本発明の化合物は、通常本系統の
化合物を製造する際に使用される公知の方法により製造
することができる。より具体的には、例えば、以下に記
載する方法によって製造することができる。BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention can be produced by a known method usually used for producing a compound of this system. More specifically, for example, it can be produced by the method described below.

【００６３】（ｉ）下記一般式（ＩＩ）(I) The following general formula (II)

【００６４】[0064]

【化４】 Embedded image

【００６５】［式中、Ｒ³ 、Ａ及びｎは、前記と同意義
を示し、Ｋは、基Ｎ（Ｒ² ）Ｃ（＝Ｘ）Ｒ¹ （Ｒ¹ 、Ｘ
及びＲ² は、前記と同意義を示す。）、ニトロ基又はア
ミノ基を示す。］の化合物を、下記の式（ＩＩＩ）Wherein R ³ , A and n are as defined above, and K is a group N (R ² ) C (＝ X) R ¹ (R ¹ , X
And R ² are as defined above. ), A nitro group or an amino group. With the following formula (III):

【００６６】[0066]

【化５】 Embedded image

【００６７】［式中、Ｒ⁴ 、Ｒ⁵ 、Ｑ及びｍは前記と同
意義を示し、Ｌは、脱離基を示す。］の化合物と反応さ
せて、下記の式（Ｉａ）、（ＶＩａ）又は（ＶＩＩａ）[Wherein, R ⁴ , R ⁵ , Q and m have the same meanings as described above, and L represents a leaving group. And the following formula (Ia), (VIa) or (VIIa)

【００６８】[0068]

【化６】 Embedded image

【００６９】［式中、Ｒ³ 、Ａ、Ｒ⁴ 、Ｒ⁵ 、Ｒ⁶ 、
Ｑ、ｍ及びｎは、前記と同意義を示し、Ｋは、上記に記
載の基を示す。］を製造する方法。[Wherein R ³ , A, R ⁴ , R ⁵ , R ⁶ ,
Q, m and n have the same meaning as described above, and K represents the group described above. ].

【００７０】（ｉｉ）前記の方法（ｉ）において、Ｋが
ニトロ基である式（ＶＩａ）の化合物を、還元剤と反応
させることにより、Ｋがアミノ基である式（ＶＩＩａ）
の化合物を製造する方法。(Ii) In the above method (i), a compound of the formula (VIa) in which K is a nitro group is reacted with a reducing agent to give a compound of the formula (VIIa) in which K is an amino group.
A method for producing a compound of the formula:

【００７１】（ｉｉｉ）前記の方法（ｉ）又は（ｉｉ）
において製造される式（ＶＩＩａ）の化合物を、式Ｒ¹
Ｃ（＝Ｘ）Ｌ² ［式中、Ｒ¹ 及びＸは前記と同意義を示
し、Ｌ² は、脱離基を示す。］の化合物と反応させて、
下記の式（Ｉａ’）(Iii) The above method (i) or (ii)
The compounds of formula are prepared (VIIa) in the formula R ¹
C (= X) L ² wherein R ¹ and X have the same meanings as described above, and L ² represents a leaving group. With the compound of formula
The following formula (Ia ′)

【００７２】[0072]

【化７】 Embedded image

【００７３】［式中、Ｒ¹ 、Ｘ、Ｒ³ 、Ａ、Ｒ⁴ 、Ｒ
⁵ 、Ｒ⁶ 、Ｑ、ｍ及びｎは、前記と同意義を示す。］の
化合物を製造する方法。[Wherein R ¹ , X, R ³ , A, R ⁴ , R
⁵ , R ⁶ , Q, m and n are as defined above. ] The method for producing the compound of [1].

【００７４】（ｉｖ）前記した式（Ｉａ’）を、必要に
応じて、式Ｒ^2aＬ³ ［式中、Ｒ^2aは、前記したＲ² より
水素原子を除いた基を示し、Ｌ³ は、脱離基を示す。］
の化合物と反応させることにより、下記の式（Ｉｂ’）(Iv) The above-mentioned formula (Ia ′) is optionally converted to a compound of the formula R ^2a L ³ [wherein R ^2a represents a group obtained by removing a hydrogen atom from the above-mentioned R ² , and L ³ represents And a leaving group. ]
By reacting with the compound of the following formula (Ib ′)

【００７５】[0075]

【化８】 Embedded image

【００７６】［式中、Ｒ¹ 、Ｒ^2a、Ｘ、Ｒ³ 、Ａ、Ｒ
⁴ 、Ｒ⁵ 、Ｒ⁶ 、Ｑ、ｍ及びｎは、前記と同意義を示
す。］の化合物を製造する方法。[Wherein R ¹ , R ^2a , X, R ³ , A, R
⁴ , R ⁵ , R ⁶ , Q, m and n are as defined above. ] The method for producing the compound of [1].

【００７７】（ｖ）前記した式（Ｉｂ’）を、必要に応
じて、適当な試薬と反応させることにより、下記の式
（Ｉｃ’）(V) The above-mentioned formula (Ib ') is reacted with an appropriate reagent, if necessary, to give the following formula (Ic')

【００７８】[0078]

【化９】 Embedded image

【００７９】［式中、Ｒ^2cは、前記したＲ² に含まれる
基であり、さらに、前記した式（Ｉｂ’）のＲ^2aより導
かれる基である。］の化合物を製造する方法。[Wherein, R ^2c is a group contained in R ² described above, and is a group derived from R ^{2a in the} above formula (Ib ′). ] The method for producing the compound of [1].

【００８０】本発明の化合物である（Ｉａ）、（Ｉ
ａ’）、（Ｉｂ’）及び（Ｉｃ’）は、必要により塩の
形態で提供することもできる。The compounds (Ia) and (Ia) of the present invention
a ′), (Ib ′) and (Ic ′) can be provided in the form of a salt, if necessary.

【００８１】本発明の化合物（Ｉ）は、さらに具体的
に、以下に記載する工程の方法によって製造することが
できる。The compound (I) of the present invention can be more specifically produced by the following method.

【００８２】（工程Ａ）(Step A)

【００８３】[0083]

【化１０】 Embedded image

【００８４】［上記工程中、Ｒ¹ 、Ｒ² 、Ｒ³ 、Ｒ⁴ 、
Ｒ⁵ 、Ｒ⁶ 、Ａ、Ｘ、Ｑ、ｍ及びｎは、前記と同意義を
示し、Ｋは、工程中に記載された基を示し、Ｌは、基Ｚ
¹ を示し、Ｚ¹ は、塩素原子、臭素原子、よう素原子又
は、基ＯＲ⁹ （Ｒ⁹ は、メタンスルホニル基のようなア
ルキルスルホニル基、ｐ−トルエンスルホニル基のよう
なアリールスルホニル基又はジメチルホスフィニル基又
はジエチルホスフィニル基のようなジアルキルホスフィ
ニル基を示す。）を示す。］Ａ−１工程工程Ａは、出発物質である式（ＩＩ）の化合物における
Ｋにより、（ｉ）Ｋが、式Ｎ（Ｒ² ）Ｃ（＝Ｘ）Ｒ¹ で
ある場合には、本発明の化合物（Ｉａ）を提供する反応
であり、（ｉｉ）Ｋが、ニトロ基又はアミノ基である場
合には、本発明の化合物（Ｉ）を製造する際の出発物質
となる式（ＶＩａ）又は（ＶＩＩａ）の化合物を提供す
る反応である。[In the above process, R ¹ , R ² , R ³ , R ⁴ ,
R ⁵ , R ⁶ , A, X, Q, m and n have the same meanings as above, K represents the group described in the step, L represents the group Z
^And Z ¹ is a chlorine atom, a bromine atom, an iodine atom or a group OR ⁹ (R ⁹ is an alkylsulfonyl group such as a methanesulfonyl group, an arylsulfonyl group such as a p-toluenesulfonyl group, or dimethyl A dialkylphosphinyl group such as a phosphinyl group or a diethylphosphinyl group). Step A-1 Step A is a process according to the present invention, wherein (i) K is a compound of the formula N (R ² ) C (＝ X) R ¹ by K in the compound of the formula (II) as a starting material. (Ii) when K is a nitro group or an amino group, a compound of formula (VIa) or (VIa) which is a starting material for producing the compound (I) of the present invention. This is a reaction to provide the compound of (VIIa).

【００８５】Ａ−１工程は、下記のＢ工程により製造さ
れるフェノール化合物又はチオフェノール化合物（Ｉ
Ｉ）と、下記のＣ及びＤ工程により製造されるベンゾチ
アゾール化合物又はベンゾオキサゾール化合物（ＩＩ
Ｉ）とを縮合させる工程である。本工程は、溶媒の存在
下、必要により塩基の存在下で行われる。In the step A-1, the phenol compound or thiophenol compound (I) produced in the following step B is used.
I) and a benzothiazole compound or a benzoxazole compound (II) produced by the following steps C and D
This is a step of condensing with I). This step is performed in the presence of a solvent, if necessary, in the presence of a base.

【００８６】使用される塩基としては、水酸化ナトリウ
ム、水酸化カリウムのようなアルカリ金属水酸化物；炭
酸ナトリウム、炭酸カリウム、炭酸セシウムのようなア
ルカリ金属炭酸塩；ナトリウムメトキシド、ナトリウム
エトキシド、カリウムｔ−ブトキシドのような金属アル
コキシド；水素化ナトリウム、水素化カリウムのような
アルカリ金属水素化物；トリエチルアミン、トリｎ−ブ
チルアミン、ジイソプロピルエチルアミンのような脂肪
族三級アミン類；１，４−ジアザビシクロ［２．２．
２］オクタン（ＤＡＢＣＯ）、１，８−ジアザビシクロ
［５．４．０］ウンデセ−７−エン（ＤＢＵ）のような
脂肪族環状三級アミン類；ピリジン、コリジン、４−
（Ｎ，Ｎ−ジメチルアミノ）ピリジンのようなピリジン
類；ｎ−ブチルリチウム、ｓ−ブチルリチウム、リチウ
ムジイソプロピルアミド、ナトリウムビストリメチ
ルシリルアミド、リチウムビストリメチルシリルアミ
ドのような有機金属塩基類等を挙げることができる。Examples of the base used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; sodium methoxide, sodium ethoxide, Metal alkoxides such as potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; aliphatic tertiary amines such as triethylamine, tri-n-butylamine and diisopropylethylamine; 1,4-diazabicyclo [ 2.2.
2] Aliphatic cyclic tertiary amines such as octane (DABCO), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU); pyridine, collidine, 4-
Pyridines such as (N, N-dimethylamino) pyridine; and organic metal bases such as n-butyllithium, s-butyllithium, lithium diisopropylamide, sodium bistrimethylsilylamide, and lithium bistrimethylsilylamide. it can.

【００８７】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；メタノール、エタノール、ｔ
−ブタノールのようなアルコール類；アセトン、メチル
イソブチルケトンのようなケトン類；アセトニトリルの
ようなニトリル類；酢酸エチルのようなエステル類；塩
化メチレン、クロロホルム、ジクロルエタンのようなハ
ロゲン化炭化水素類；ジエチルエーテル、テトラヒドロ
フラン、ジオキサンのようなエーテル類；トルエンのよ
うな芳香族炭化水素類；ジメチルホルムアミド、ジメチ
ルアセトアミドのようなアミド類；ジメチルスルホキシ
ドのようなスルホキシド類等、及びこれらの混合溶剤を
挙げることができる。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent.
Alcohols such as butanol; ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; diethyl. Ethers such as ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as toluene; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethylsulfoxide; and mixed solvents thereof. it can.

【００８８】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、０℃乃至１００℃である。The reaction temperature is usually -90 ° C to 200 ° C, preferably 0 ° C to 100 ° C.

【００８９】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、１５分乃至６
時間である。The reaction time mainly depends on the reaction temperature, starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 15 minutes to 6 hours
Time.

【００９０】（工程Ｂ）(Step B)

【００９１】[0091]

【化１１】 Embedded image

【００９２】上記工程中、Ｒ¹⁰はＲ^10a 又はＲ^10b を示
し、Ｒ^10a は、水酸基の保護基又はメルカプト基の保護
基を示し、Ｒ^10b は、基（ＩＩＩａ）In the above process, R ¹⁰ represents R ^10a or R ^10b , R ^10a represents a protecting group for a hydroxyl group or a mercapto group, and R ^10b represents a group (IIIa)

【００９３】[0093]

【化１２】 Embedded image

【００９４】［式中、Ｒ⁴ 、Ｒ⁵ 、Ｒ⁶ 、Ｑ及びｍは、
前記と同意義を示す。］を示し、Ｒ¹、Ｒ² 、Ｒ³ 、Ｒ⁴
、Ｒ⁵ 、Ｒ⁶ 、Ａ、Ｑ、Ｘ、ｍ及びｎは前記と同意義
を示し、Ｒ^2aは、Ｃ１〜Ｃ６アルキル基（当該アルキル
基は、水酸基又は１乃至４個のハロゲン原子により置換
されても良い）、Ｃ３〜Ｃ６シクロアルキル基、Ｃ２〜
Ｃ６アルケニル基（当該アルケニル基は、１乃至４個の
ハロゲン原子により置換されても良い）、Ｃ２〜Ｃ６ア
ルキニル基（当該アルキニル基は、１乃至４個のハロゲ
ン原子により置換されても良い）又は基（−ＹＲ⁷ ）を
示し、Ｒ⁷ 及びＹは前記と同意義を示し、Ｒ^2bは、基Ｃ
Ｈ₂ ＯＨ、ＣＨ₂ ＣＨ₂ ＯＨ、ＣＨ₂ ＯＲ⁷ 又はＣＨ₂
ＣＨ₂ ＯＲ⁷ より選ばれる一つの基を示し、Ｒ^2cは、基
ＣＨ₂ ＯＨ、ＣＨ₂ ＣＨ₂ ＯＨ、ＣＨ₂ ＯＲ⁷ 、ＣＨ₂
ＣＨ₂ ＯＲ⁷ 、ＣＨ₂ ＯＣＯＲ⁷ 又はＣＨ₂ ＣＨ₂ ＯＣ
ＯＲ⁷ より選ばれる一つの基を示す。Wherein R ⁴ , R ⁵ , R ⁶ , Q and m are
The meaning is as defined above. And R ¹ , R ² , R ³ , R ⁴
, R ⁵ , R ⁶ , A, Q, X, m and n are as defined above, and R ^2a is a C1 to C6 alkyl group (the alkyl group is substituted by a hydroxyl group or 1 to 4 halogen atoms) C3 to C6 cycloalkyl group, C2 to C6
A C6 alkenyl group (the alkenyl group may be substituted by 1 to 4 halogen atoms), a C2 to C6 alkynyl group (the alkynyl group may be substituted by 1 to 4 halogen atoms) or A group (—YR ⁷ ), R ⁷ and Y are as defined above, and R ^2b is a group C
H ₂ OH, CH ₂ CH ₂ OH, CH ₂ OR ⁷ or CH ₂
CH ₂ OR ⁷ represents one group selected from the group ^consisting of CH ₂ OH, CH ₂ CH ₂ OH, CH ₂ OR ⁷ and CH ₂
CH ₂ OR ⁷ , CH ₂ OCOR ⁷ or CH ₂ CH ₂ OC
Shows one group selected from OR ^7.

【００９５】Ｒ^10a の定義における「水酸基の保護基又
はメルカプト基の保護基」とは、その後の工程において
水酸基又はメルカプト基が反応せず、又、他の置換基が
反応しない条件下において、水酸基又はメルカプト基か
ら脱離するものであれば特に限定はないが、好適には、
アセチル、プロピオニルのようなアシル基；メトキシカ
ルボニル基、エトキシカルボニル基のようなアルコキシ
カルボニル基である。The term “protecting group for hydroxyl group or mercapto group” in the definition of R ^10a means that a hydroxyl group or a mercapto group does not react in a subsequent step and that a hydroxyl group does not react with other substituents. Or if it is eliminated from the mercapto group, there is no particular limitation, but preferably,
Acyl groups such as acetyl and propionyl; and alkoxycarbonyl groups such as methoxycarbonyl and ethoxycarbonyl.

【００９６】Ｂ−１工程Ｂ−１工程は、フェノール化合物又はチオフェノール化
合物（ＩＶ）の水酸基又はメルカプト基を保護基Ｒ^10a
で保護し、化合物（Ｖ）を得る工程である。 Step B-1 In step B-1, the hydroxyl group or mercapto group of the phenol compound or thiophenol compound (IV) is protected with a protecting group R ^10a
And the step of obtaining a compound (V).

【００９７】本工程は、溶媒中、塩基の存在下、化合物
（ＩＶ）と、一般式Ｒ^10a Ｌ¹ で表される化合物［式
中、Ｒ^10a は前記と同意義を示し、Ｌ¹ は脱離基（ここ
で脱離基とは、通常求核残基として脱離する基のことを
いい、好適には、塩素原子、臭素原子、沃素原子のよう
なハロゲン原子；メタンスルホニルオキシ、p-トルエン
スルホニルオキシのようなスルホニルオキシ基；メチル
スルフィニルオキシ、エチルスルフィニルオキシのよう
なスルフィニルオキシ基；ジメチルホスフィニルオキ
シ、ジエチルホスフィニルオキシのようなホスフィニル
オキシ基である。）を示す。］とを反応することにより
行われる。In this step, in a solvent in the presence of a base, compound (IV) and a compound represented by the general formula R ^10a L ¹ [wherein R ^10a has the same meaning as described above, and L ¹ is Leaving group (here, leaving group refers to a group which usually leaves as a nucleophilic residue, preferably a halogen atom such as a chlorine atom, a bromine atom and an iodine atom; methanesulfonyloxy, p- A sulfonyloxy group such as toluenesulfonyloxy; a sulfinyloxy group such as methylsulfinyloxy and ethylsulfinyloxy; and a phosphinyloxy group such as dimethylphosphinyloxy and diethylphosphinyloxy. By reacting

【００９８】使用される塩基としては、フェノール類又
はチオフェノール類のプロトンを脱離させる強さの塩基
であれば特に限定はないが、好適には、水酸化ナトリウ
ム、水酸化カリウムのようなアルカリ金属水酸化物；炭
酸ナトリウム、炭酸カリウムのようなアルカリ金属炭酸
塩；ナトリウムメトキシド、ナトリウムエトキシド、カ
リウムt-ブトキシドのような金属アルコキシド；水素化
ナトリウム、水素化カリウムのようなアルカリ金属水素
化物；トリエチルアミン、トリｎ−ブチルアミン、ジイ
ソプロピルエチルアミンのような脂肪族三級アミン類；
１，４−ジアザビシクロ［２．２．２］オクタン（ＤＡ
ＢＣＯ）、１，８−ジアザビシクロ［５．４．０］ウン
デセ−７−エン（ＤＢＵ）のような脂肪族環状三級アミ
ン類；ピリジン、コリジン、４−（Ｎ，Ｎ−ジメチルア
ミノ）ピリジンのようなピリジン類等を挙げることがで
きる。The base to be used is not particularly limited as long as it is a base capable of removing the proton of phenols or thiophenols, but is preferably an alkali such as sodium hydroxide or potassium hydroxide. Metal hydroxides; alkali metal carbonates such as sodium carbonate and potassium carbonate; metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride Aliphatic tertiary amines such as triethylamine, tri-n-butylamine, diisopropylethylamine;
1,4-diazabicyclo [2.2.2] octane (DA
BCO), aliphatic cyclic tertiary amines such as 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU); pyridine, collidine, 4- (N, N-dimethylamino) pyridine Such pyridines can be mentioned.

【００９９】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；メタノール、エタノール、ｔ
−ブタノールのようなアルコール類；アセトン、メチル
イソブチルケトンのようなケトン類；アセトニトリルの
ようなニトリル類；酢酸エチルのようなエステル類；塩
化メチレン、クロロホルム、ジクロルエタンのようなハ
ロゲン化炭化水素類；ジエチルエーテル、テトラヒドロ
フラン、ジオキサンのようなエーテル類；トルエンのよ
うな芳香族炭化水素類；ジメチルホルムアミド、ジメチ
ルアセトアミドのようなアミド類、ジメチルスルホキシ
ドのようなスルホキシド類等である。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent.
Alcohols such as butanol; ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; diethyl. Ethers such as ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as toluene; amides such as dimethylformamide and dimethylacetamide; and sulfoxides such as dimethylsulfoxide.

【０１００】反応温度は、通常−７０℃乃至２００℃で
あり、好適には、−１０℃乃至８０℃である。The reaction temperature is usually from -70 ° C to 200 ° C, preferably from -10 ° C to 80 ° C.

【０１０１】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、３０分乃至５
時間である。The reaction time mainly depends on the reaction temperature, the starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 30 minutes to 5 hours
Time.

【０１０２】Ｂ−２工程Ｂ−２工程は、Ｂ−１工程により製造される化合物
（Ｖ）をニトロ化し、水酸基又はメルカプト基のパラ位
（フェノール又はチオフェノールの４位）がニトロ化さ
れた化合物（ＶＩｂ）を得る工程である。 Step B-2 In step B-2, the compound (V) produced in step B-1 is nitrated, and the hydroxyl group or the mercapto group is nitrated at the para position (position 4 of phenol or thiophenol). This is a step of obtaining a compound (VIb).

【０１０３】本反応は、例えば濃硫酸−濃硝酸の混酸を
用いる方法や硝酸カリウムを用いる方法のような、通常
芳香環をニトロ化する際の常法に従って行なうことがで
きる。This reaction can be carried out according to a conventional method for nitrating an aromatic ring, such as a method using a mixed acid of concentrated sulfuric acid and concentrated nitric acid or a method using potassium nitrate.

【０１０４】本工程は、溶媒の存在下又は非存在下行わ
れる。使用される溶媒としては、反応を阻害しないもの
であれば特に限定はないが、好適には、酢酸；ジクロロ
メタン、クロロホルム、１，２−ジクロロエタンのよう
なハロゲン化炭化水素類等を挙げることができる。This step is performed in the presence or absence of a solvent. The solvent used is not particularly limited as long as it does not inhibit the reaction, but preferably includes acetic acid; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane. .

【０１０５】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、−５０℃乃至８０℃である。The reaction temperature is usually from -90 ° C to 200 ° C, preferably from -50 ° C to 80 ° C.

【０１０６】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、３０分乃至６
時間である。The reaction time mainly depends on the reaction temperature, starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 30 minutes to 6 hours
Time.

【０１０７】Ｂ−３工程Ｂ−３工程は、使用される出発物質により、（ｉ）Ｒ¹⁰
が前記した保護基のＲ^10a である場合、Ｂ−２工程によ
り製造される化合物（ＶＩｂ）のニトロ基を還元し、化
合物（ＶＩＩ）の一部である４−アミノフェノール又は
４−アミノチオフェノール化合物（ＶＩＩｂ）を得る工
程であり、（ｉｉ）Ｒ¹⁰が前記したＲ^10b である場合、
Ａ−１工程やＤ−７工程により製造される化合物（ＶＩ
ａ）のニトロ基を還元し、化合物（ＶＩＩ）の一部であ
る４−アミノフェノール又は４−アミノチオフェノール
化合物（ＶＩＩａ）を得る工程である。 Step B-3 Step B-3 depends on (i) R ¹⁰ depending on the starting materials used.
Is the protecting group R ^10a described above, the nitro group of the compound (VIb) produced in Step B-2 is reduced, and 4-aminophenol or 4-aminothiophenol which is a part of the compound (VII) is reduced. A step of obtaining a compound (VIIb), wherein (ii) when R ¹⁰ is R ^10b described above,
Compound (VI) produced by step A-1 or step D-7
In this step, the nitro group of a) is reduced to obtain a 4-aminophenol or 4-aminothiophenol compound (VIIa) which is a part of the compound (VII).

【０１０８】本工程は、例えばＰｄ−Ｃ触媒下水素添加
する方法、濃塩酸存在下塩化第一スズを用いる方法、酢
酸中亜鉛を用いる方法のような、通常ニトロ基をアミノ
基に還元する際の常法に従って行なうことができる。This step is usually carried out when a nitro group is reduced to an amino group, such as a method of hydrogenation in the presence of a Pd-C catalyst, a method of using stannous chloride in the presence of concentrated hydrochloric acid, or a method of using zinc in acetic acid. Can be carried out according to the conventional method.

【０１０９】本工程は、溶媒の存在下又は非存在下行わ
れる。This step is performed in the presence or absence of a solvent.

【０１１０】使用される溶媒としては、反応を阻害しな
いものであれば特に限定はなが、好適には、水；メタノ
ール、エタノール、ｔ−ブタノールのようなアルコール
類；酢酸エチルのようなエステル類；ジエチルエーテ
ル、テトラヒドロフラン、ジオキサンのようなエーテル
類；トルエンのような芳香族炭化水素類；ジメチルホル
ムアミド、ジメチルアセトアミドのようなアミド類、ジ
メチルスルホキシドのようなスルホキシド類等を挙げる
ことができる。The solvent used is not particularly limited as long as it does not inhibit the reaction, but is preferably water; alcohols such as methanol, ethanol and t-butanol; and esters such as ethyl acetate. Ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as toluene; amides such as dimethylformamide and dimethylacetamide; and sulfoxides such as dimethylsulfoxide.

【０１１１】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、０℃乃至１００℃である。The reaction temperature is generally -90 ° C to 200 ° C, preferably 0 ° C to 100 ° C.

【０１１２】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、３０分乃至１
２時間である。The reaction time mainly depends on the reaction temperature, starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 30 minutes to 1 hour
2 hours.

【０１１３】Ｂ−４工程Ｂ−４工程は、使用される出発物質により、（ｉ）化合
物（ＶＩＩａ）を、溶媒の存在下又は非存在下、必要に
応じて塩基の存在下、一般式Ｒ¹ Ｃ（＝Ｘ）Ｌ² で表わ
される化合物［式中、Ｒ¹ 及びＸは前記と同意義を示
し、Ｌ² は、例えば、塩素原子、臭素原子、よう素原
子、メタンスルホニルオキシ基又はｐ−トルエンスルホ
ニルオキシ基のようなスルホニルオキシ基、メチルスル
フィニルオキシ基又はエチルスルフィニルオキシ基のよ
うなアルキルスルフィニルオキシ基及びジメチルホスフ
ィニルオキシ基又はジエチルホスフィニルオキシキ基の
ようなジアルキルホスフィニルオキシ基のような脱離基
を示す。］と反応させる場合には、式（Ｉａ）の化合物
を製造する工程であり、（ｉｉ）化合物（ＶＩＩｂ）
を、溶媒の存在下又は非存在下、必要に応じて塩基の存
在下、一般式Ｒ¹ Ｃ（＝Ｘ）Ｌ² で表わされる化合物
［式中、Ｒ¹ 、Ｘ及びＬ² は前記と同意義を示す。］と
反応させる場合には、式（ＶＩＩＩ）の化合物を製造す
る工程である。 Step B-4 Step B-4 is a step of subjecting (i) compound (VIIa) to a compound represented by the general formula R in the presence or absence of a solvent, if necessary, in the presence of a base, depending on the starting materials used. A compound represented by ¹ C (2X) L ² wherein R ¹ and X are as defined above, and L ² is, for example, a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group or p A sulfonyloxy group such as a toluenesulfonyloxy group, an alkylsulfinyloxy group such as a methylsulfinyloxy group or an ethylsulfinyloxy group, and a dialkylphosphinyl group such as a dimethylphosphinyloxy group or a diethylphosphinyloxy group. A leaving group such as an oxy group is shown. Is a step of producing a compound of the formula (Ia), wherein (ii) the compound (VIIb)
Is a compound represented by the general formula R ¹ C (ＣX) L ² in the presence or absence of a solvent, if necessary, in the presence of a base, wherein R ¹ , X and L ² are the same as defined above. Show meaning. Is a step of producing a compound of the formula (VIII).

【０１１４】使用される塩基としては、水酸化ナトリウ
ム、水酸化カリウムのようなアルカリ金属水酸化物；炭
酸ナトリウム、炭酸カリウムのようなアルカリ金属炭酸
塩；ナトリウムメトキシド、ナトリウムエトキシド、カ
リウムｔ−ブトキシドのような金属アルコキシド；水素
化ナトリウム、水素化カリウムのようなアルカリ金属水
素化物；トリエチルアミン、トリｎ−ブチルアミン、ジ
イソプロピルエチルアミンのような脂肪族三級アミン
類；Ｎ，Ｎ−ジメチルアニリン、Ｎ，Ｎ−ジエチルアニ
リンのような三級アニリン類；１，４−ジアザビシクロ
［２．２．２］オクタン（ＤＡＢＣＯ）、１，８−ジア
ザビシクロ［５．４．０］ウンデセ−７−エン（ＤＢ
Ｕ）のような脂肪族環状三級アミン類；ピリジン、コリ
ジン、４−（Ｎ，Ｎ−ジメチルアミノ）ピリジンのよう
なピリジン類；ｎ−ブチルリチウム、ｓ−ブチルリチウ
ム、リチウムジイソプロピルアミド、ナトリウムビ
ストリメチルシリルアミド、リチウムビストリメチル
シリルアミドのような有機金属塩基類等を挙げることが
できる。Examples of the base used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium methoxide, sodium ethoxide and potassium tert-oxide. Metal alkoxides such as butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; aliphatic tertiary amines such as triethylamine, tri-n-butylamine and diisopropylethylamine; N, N-dimethylaniline; Tertiary anilines such as N-diethylaniline; 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [5.4.0] undec-7-ene (DB
Aliphatic cyclic tertiary amines such as U); pyridines such as pyridine, collidine, 4- (N, N-dimethylamino) pyridine; n-butyllithium, s-butyllithium, lithium diisopropylamide, sodium bis Organometallic bases such as trimethylsilylamide and lithium bistrimethylsilylamide can be exemplified.

【０１１５】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；メタノール、エタノール、ｔ
−ブタノールのようなアルコール類；アセトン、メチル
イソブチルケトンのようなケトン類；アセトニトリルの
ようなニトリル類；酢酸エチルのようなエステル類；塩
化メチレン、クロロホルム、ジクロルエタンのようなハ
ロゲン化炭化水素類；ジエチルエーテル、テトラヒドロ
フラン、ジオキサンのようなエーテル類；トルエンのよ
うな芳香族炭化水素類等、及びこれらの混合溶剤を挙げ
ることができる。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but is preferably water; methanol, ethanol, t
Alcohols such as butanol; ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; diethyl. Examples thereof include ethers such as ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as toluene; and a mixed solvent thereof.

【０１１６】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、−１０℃乃至１００℃である。The reaction temperature is generally -90 ° C to 200 ° C, preferably -10 ° C to 100 ° C.

【０１１７】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、１５分乃至６
時間である。The reaction time mainly depends on the reaction temperature, starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 15 minutes to 6 hours
Time.

【０１１８】本工程は、Ｒ¹ がＲ^1a［Ｒ^1aはＣ１〜Ｃ６
アルコキシ基（当該アルコキシ基は、１乃至４個のハロ
ゲン原子により置換されても良い）又はＣ１〜Ｃ６アル
キルチオ基（当該アルキルチオ基は、１乃至４個のハロ
ゲン原子により置換されても良い）を示す。］である場
合、溶媒の存在下又は非存在下、必要により塩基の存在
下、式（ＶＩＩ）の化合物を、Ｃ（＝Ｘ）Ｃｌ₂ で表わ
される化合物（Ｘは、前記と同意義を示す。）と反応さ
せて、イソシアネート又はイソチオシアネートを中間体
として生成し、更に、溶媒の存在下又は非存在下、必要
により塩基存在下で、Ｒ^1aＺ² で表わされる化合物［式
中、Ｒ^1aは、前記と同意義を示し、Ｚ²は水素原子又は
ナトリウム、カリウムのようなアルカリ金属を示す。］
とを反応することによっても行うことができる。In this step, R ¹ is R ^1a [R ^1a is C1 to C6
Represents an alkoxy group (the alkoxy group may be substituted by 1 to 4 halogen atoms) or a C1 to C6 alkylthio group (the alkylthio group may be substituted by 1 to 4 halogen atoms) . In the presence of a solvent, a compound of the formula (VII) is converted to a compound represented by C (= X) Cl ₂ (X is as defined above) in the presence or absence of a solvent, if necessary, in the presence of a base. ) To produce an isocyanate or isothiocyanate as an intermediate, and in the presence or absence of a solvent, if necessary, in the presence of a base, a compound represented by R ^1a Z ² [wherein R ^1a Has the same meaning as described above, and Z ² represents a hydrogen atom or an alkali metal such as sodium or potassium. ]
The reaction can also be performed by reacting

【０１１９】使用される塩基としては、水酸化ナトリウ
ム、水酸化カリウムのようなアルカリ金属水酸化物；炭
酸ナトリウム、炭酸カリウム、炭酸セシウムのようなア
ルカリ金属炭酸塩；ナトリウムメトキシド、ナトリウム
エトキシド、カリウムｔ−ブトキシドのような金属アル
コキシド；水素化ナトリウム、水素化カリウムのような
アルカリ金属水素化物；トリエチルアミン、トリｎ−ブ
チルアミン、ジイソプロピルエチルアミンのような脂肪
族三級アミン類；１，４−ジアザビシクロ［２．２．
２］オクタン（ＤＡＢＣＯ）、１，８−ジアザビシクロ
［５．４．０］ウンデセ−７−エン（ＤＢＵ）のような
脂肪族環状三級アミン類；ピリジン、コリジン、４−
（Ｎ，Ｎ−ジメチルアミノ）ピリジンのようなピリジン
類；ｎ−ブチルリチウム、ｓ−ブチルリチウム、リチウ
ムジイソプロピルアミド、ナトリウムビストリメチ
ルシリルアミド、リチウムビストリメチルシリルアミ
ドのような有機金属塩基類を挙げることができる。Examples of the base used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; sodium methoxide, sodium ethoxide, Metal alkoxides such as potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; aliphatic tertiary amines such as triethylamine, tri-n-butylamine and diisopropylethylamine; 1,4-diazabicyclo [ 2.2.
2] Aliphatic cyclic tertiary amines such as octane (DABCO), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU); pyridine, collidine, 4-
Pyridines such as (N, N-dimethylamino) pyridine; and organometallic bases such as n-butyllithium, s-butyllithium, lithium diisopropylamide, sodium bistrimethylsilylamide, and lithium bistrimethylsilylamide. .

【０１２０】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、メタノール、エタノール、ｔ−ブ
タノールのようなアルコール類；アセトン、メチルイソ
ブチルケトンのようなケトン類；酢酸エチルのようなエ
ステル類；塩化メチレン、クロロホルム、ジクロルエタ
ンのようなハロゲン化炭化水素類；ジエチルエーテル、
テトラヒドロフラン、ジオキサンのようなエーテル類；
トルエンのような芳香族炭化水素類；ジメチルホルムア
ミド、ジメチルアセトアミドのようなアミド類、ジメチ
ルスルホキシドのようなスルホキシド類等、及びこれら
の混合溶剤を挙げることができる。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but is preferably alcohols such as methanol, ethanol and t-butanol; Ketones such as methyl isobutyl ketone; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; diethyl ether;
Ethers such as tetrahydrofuran and dioxane;
Aromatic hydrocarbons such as toluene; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethylsulfoxide; and a mixed solvent thereof.

【０１２１】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、−１０℃乃至１００℃である。The reaction temperature is usually from -90 ° C to 200 ° C, preferably from -10 ° C to 100 ° C.

【０１２２】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常３分乃至２４時間であり、好適には、５分乃至６時
間である。The reaction time mainly depends on the reaction temperature, starting compound,
Depending on the type of reaction reagent and solvent used,
It is usually from 3 minutes to 24 hours, preferably from 5 minutes to 6 hours.

【０１２３】さらに、本工程は、Ｘが硫黄原子であり、
Ｒ¹ がＣ１〜Ｃ６アルキルチオ基（当該アルキルチオ基
は、Ｃ１〜Ｃ６アルコキシ基又は、１乃至４個のハロゲ
ン原子により置換されてよい）である場合、溶媒の存在
下又は非存在下、塩基存在下で、二硫化炭素とＲ^1bＺ³
で表わされる化合物［式中、Ｒ^1bは、Ｃ１〜Ｃ６アルキ
ル基（当該アルキル基は、Ｃ１〜Ｃ６アルコキシ基又
は、１乃至４個のハロゲン原子により置換されてもよ
い）を示し、Ｚ³ は、塩素原子、臭素原子又は沃素原子
を示す。］と反応することによっても行うことができ
る。Further, in this step, X is a sulfur atom;
When R ¹ is a C1 to C6 alkylthio group (the alkylthio group may be substituted with a C1 to C6 alkoxy group or 1 to 4 halogen atoms), in the presence or absence of a solvent, in the presence of a base And carbon disulfide and R ^1b Z ³
Wherein R ^1b represents a C1-C6 alkyl group (the alkyl group may be substituted with a C1-C6 alkoxy group or 1-4 halogen atoms), and Z ³ represents , A chlorine atom, a bromine atom or an iodine atom. ] Can also be carried out.

【０１２４】使用される塩基としては、水酸化ナトリウ
ム、水酸化カリウムのようなアルカリ金属水酸化物；炭
酸ナトリウム、炭酸カリウム、炭酸セシウムのようなア
ルカリ金属炭酸塩；ナトリウムメトキシド、ナトリウム
エトキシド、カリウムｔ−ブトキシドのような金属アル
コキシド；水素化ナトリウム、水素化カリウムのような
アルカリ金属水素化物；トリエチルアミン、トリｎ−ブ
チルアミン、ジイソプロピルエチルアミンのような脂肪
族三級アミン類；１，４−ジアザビシクロ［２．２．
２．］オクタン（ＤＡＢＣＯ）、１，８−ジアザビシク
ロ［５，４，０］ウンデセ−７−エン（ＤＢＵ）のよう
な脂肪族環状三級アミン類；ピリジン、コリジン、４−
（Ｎ，Ｎ−ジメチルアミノ) ピリジンのようなピリジン
類；ｎ−ブチルリチウム、ｓ−ブチルリチウム、リチウ
ムジイソプロピルアミド、ナトリウムビストリメチ
ルシリルアミド、リチウムビストリメチルシリルアミ
ドのような有機金属塩基類を挙げることができる。Examples of the base used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; sodium methoxide, sodium ethoxide, Metal alkoxides such as potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; aliphatic tertiary amines such as triethylamine, tri-n-butylamine and diisopropylethylamine; 1,4-diazabicyclo [ 2.2.
2. Aliphatic cyclic tertiary amines such as octane (DABCO) and 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU); pyridine, collidine, 4-
Pyridines such as (N, N-dimethylamino) pyridine; and organometallic bases such as n-butyllithium, s-butyllithium, lithium diisopropylamide, sodium bistrimethylsilylamide, and lithium bistrimethylsilylamide. .

【０１２５】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；メタノール、エタノール、ｔ
−ブタノールのようなアルコール類；アセトン、メチル
イソブチルケトンのようなケトン類；アセトニトリルの
ようなニトリル類；酢酸エチルのようなエステル類；塩
化メチレン、クロロホルム、ジクロルエタンのようなハ
ロゲン化炭化水素類；ジエチルエーテル、テトラヒドロ
フラン、ジオキサンのようなエーテル類；トルエンのよ
うな芳香族炭化水素類；ジメチルホルムアミド、ジメチ
ルアセトアミドのようなアミド類、ジメチルスルホキシ
ドのようなスルホキシド類等、及びこれらの混合溶剤を
挙げることができる。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent.
Alcohols such as butanol; ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; diethyl. Ethers such as ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as toluene; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethylsulfoxide; and mixed solvents thereof. it can.

【０１２６】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、−１０℃乃至１００℃である。The reaction temperature is usually from -90 ° C to 200 ° C, preferably from -10 ° C to 100 ° C.

【０１２７】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、１０分乃至６
時間である。The reaction time mainly depends on the reaction temperature, the starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 10 minutes to 6 hours
Time.

【０１２８】Ｂ−５工程Ｂ−５工程は、化合物（Ｉａ）又は（ＶＩＩＩ）のアミ
ド基又はカルバマート基の窒素原子に置換基Ｒ^2aを導入
する工程である。 Step B-5 Step B-5 is a step of introducing a substituent R ^2a into the nitrogen atom of the amide group or carbamate group of compound (Ia) or (VIII).

【０１２９】本工程は、溶媒中、塩基の存在下、一般式
Ｒ^2aＬ³ で表される化合物［式中、Ｒ^2aは、前記Ｒ² に
おいて水素原子を除いたものと同意義を示し、Ｌ³ は脱
離基（ここで脱離基とは、通常求核残基として脱離する
基のことをいい、好適には、塩素原子、臭素原子、沃素
原子のようなハロゲン原子；メタンスルホニルオキシ、
ｐ−トルエンスルホニルオキシのようなスルホニルオキ
シ基；メチルスルフィニルオキシ、エチルスルフィニル
オキシのようなスルフィニルオキシ基；ジメチルホスフ
ィニルオキシ、ジエチルホスフィニルオキシのようなホ
スフィニルオキシ基である。）を示す。］と反応するこ
とにより行われる。In this step, in a solvent in the presence of a base, a compound represented by the general formula R ^2a L ³ [wherein R ^2a has the same meaning as in R ² except for removing a hydrogen atom, L ³ is a leaving group (here, leaving group means a group which usually leaves as a nucleophilic residue, preferably a halogen atom such as a chlorine atom, a bromine atom and an iodine atom; methanesulfonyl) Oxy,
sulfonyloxy groups such as p-toluenesulfonyloxy; sulfinyloxy groups such as methylsulfinyloxy and ethylsulfinyloxy; phosphinyloxy groups such as dimethylphosphinyloxy and diethylphosphinyloxy. ). And the reaction is carried out.

【０１３０】使用される塩基としては、フェノール類又
はチオフェノール類のプロトンを脱離させる強さの塩基
であれば特に限定はないが、好適には、水酸化ナトリウ
ム、水酸化カリウムのようなアルカリ金属水酸化物；炭
酸ナトリウム、炭酸カリウムのようなアルカリ金属炭酸
塩；ナトリウムメトキシド、ナトリウムエトキシド、カ
リウムt-ブトキシドのような金属アルコキシド；水素化
ナトリウム、水素化カリウムのようなアルカリ金属水素
化物；トリエチルアミン、トリｎ−ブチルアミン、ジイ
ソプロピルエチルアミンのような脂肪族三級アミン類；
１，４−ジアザビシクロ［２．２．２］オクタン（ＤＡ
ＢＣＯ）、１，８−ジアザビシクロ［５．４．０］ウン
デセ−７−エン（ＤＢＵ）のような脂肪族環状三級アミ
ン類；ピリジン、コリジン、４−（Ｎ，Ｎ−ジメチルア
ミノ）ピリジンのようなピリジン類等を挙げることがで
きる。The base to be used is not particularly limited as long as it is a base capable of desorbing protons of phenols or thiophenols, but is preferably an alkali such as sodium hydroxide or potassium hydroxide. Metal hydroxides; alkali metal carbonates such as sodium carbonate and potassium carbonate; metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride Aliphatic tertiary amines such as triethylamine, tri-n-butylamine, diisopropylethylamine;
1,4-diazabicyclo [2.2.2] octane (DA
BCO), aliphatic cyclic tertiary amines such as 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU); pyridine, collidine, 4- (N, N-dimethylamino) pyridine Such pyridines can be mentioned.

【０１３１】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；メタノール、エタノール、ｔ
−ブタノールのようなアルコール類；アセトン、メチル
イソブチルケトンのようなケトン類；アセトニトリルの
ようなニトリル類；酢酸エチルのようなエステル類；塩
化メチレン、クロロホルム、ジクロルエタンのようなハ
ロゲン化炭化水素類；ジエチルエーテル、テトラヒドロ
フラン、ジオキサンのようなエーテル類；トルエンのよ
うな芳香族炭化水素類；ジメチルホルムアミド、ジメチ
ルアセトアミドのようなアミド類、ジメチルスルホキシ
ドのようなスルホキシド類等である。The solvent used is not particularly limited as long as it does not hinder the reaction and dissolves the starting materials to some extent, but is preferably water; methanol, ethanol, t
Alcohols such as butanol; ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; diethyl. Ethers such as ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as toluene; amides such as dimethylformamide and dimethylacetamide; and sulfoxides such as dimethylsulfoxide.

【０１３２】反応温度は、通常−７０℃乃至２００℃で
あり、好適には、−１０℃乃至８０℃である。The reaction temperature is usually from -70 ° C to 200 ° C, preferably from -10 ° C to 80 ° C.

【０１３３】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、３０分乃至５
時間である。The reaction time mainly depends on the reaction temperature, starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 30 minutes to 5 hours
Time.

【０１３４】さらに、本工程は、Ｒ^2aが基ＣＨ₂ ＯＨで
ある場合、化合物（Ｉａ）又は（ＶＩＩＩ）を、溶媒の
存在下又は非存在下、必要により塩基の存在下、ホルマ
リンと反応させることにより化合物（Ｉｂ）又は（Ｉ
Ｘ）を製造することができる。Further, in this step, when R ^2a is a group CH ₂ OH, the compound (Ia) or (VIII) is reacted with formalin in the presence or absence of a solvent and, if necessary, in the presence of a base. Compound (Ib) or (I
X) can be produced.

【０１３５】使用される塩基としては、水酸化ナトリウ
ム、水酸化カリウムのようなアルカリ金属水酸化物；炭
酸ナトリウム、炭酸カリウム、炭酸セシウムのようなア
ルカリ金属炭酸塩を挙げることができるが、好適には炭
酸ナトリウム、炭酸カリウム、炭酸セシウムのようなア
ルカリ金属炭酸塩である。Examples of the base used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate. Is an alkali metal carbonate such as sodium carbonate, potassium carbonate, cesium carbonate.

【０１３６】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；メタノール、エタノール、ｔ
−ブタノールのようなアルコール類；アセトン、メチル
イソブチルケトンのようなケトン類；アセトニトリルの
ようなニトリル類；酢酸エチルのようなエステル類；塩
化メチレン、クロロホルム、ジクロルエタンのようなハ
ロゲン化炭化水素類；ジエチルエーテル、テトラヒドロ
フラン、ジオキサンのようなエーテル類；トルエンのよ
うな芳香族炭化水素類；ジメチルホルムアミド、ジメチ
ルアセトアミドのようなアミド類、ジメチルスルホキシ
ドのようなスルホキシド類等、及びこれらの混合溶剤を
挙げることができる。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. Preferably, the solvent is water; methanol, ethanol, t
Alcohols such as butanol; ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; diethyl. Ethers such as ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as toluene; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethylsulfoxide; and mixed solvents thereof. it can.

【０１３７】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、０℃乃至５０℃である。The reaction temperature is usually -90 ° C to 200 ° C, preferably 0 ° C to 50 ° C.

【０１３８】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、１０分乃至６
時間であり、本製造法は、通常超音波の照射下に行なう
のが好ましい。The reaction time mainly depends on the reaction temperature, the starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 10 minutes to 6 hours
It is preferable that the production method is usually performed under irradiation of ultrasonic waves.

【０１３９】Ｂ−６工程Ｂ−６工程は、Ｂ−４工程により製造される化合物（Ｖ
ＩＩＩ）又はＢ−５工程により製造される化合物（Ｉ
Ｘ）の保護基Ｒ^10a を脱保護し、Ａ−１工程の原料であ
るフェノール化合物又はチオフェノール化合物（ＩＩ
ａ）を得る工程である。 Step B-6 Step B-6 is a step of preparing the compound (V) produced by Step B-4.
III) or compound (I) produced by step B-5
Deprotection of the protecting group R ^10a of X), the phenol compound or thiophenol compound (II
This is the step of obtaining a).

【０１４０】本工程は、保護されたフェノール又はチオ
フェノールの脱保護反応に通常使われる製造法により行
われ、その方法は保護基の種類により変わりうる。This step is carried out by a production method usually used for a deprotection reaction of a protected phenol or thiophenol, and the method may vary depending on the type of the protecting group.

【０１４１】例えば、本工程は、アルカリ存在下、加水
分解して脱保護基を行うことにより行なわれる。For example, this step is carried out by performing hydrolysis and deprotection in the presence of an alkali.

【０１４２】使用されるアルカリとしては、例えば、水
酸化ナトリウム、水酸化カリウムのようなアルカリ金属
水酸化物；炭酸ナトリウム、炭酸カリウム、炭酸セシウ
ムのようなアルカリ金属炭酸塩；炭酸水素ナトリウムの
ようなアルカリ金属炭酸水素塩等を挙げることができ
る。Examples of the alkali used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; Alkali metal bicarbonate and the like can be mentioned.

【０１４３】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；メタノール、エタノール、ｔ
−ブタノールのようなアルコール類；ジエチルエーテ
ル、テトラヒドロフラン、ジオキサンのようなエーテル
類；トルエンのような芳香族炭化水素類等、及びこれら
の混合溶剤を挙げることができる。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but is preferably water; methanol, ethanol, t
Alcohols such as butanol; ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as toluene; and mixed solvents thereof.

【０１４４】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、−５０乃至１００℃である。The reaction temperature is generally -90 ° C to 200 ° C, preferably -50 ° C to 100 ° C.

【０１４５】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、３０分乃至１
２時間である。The reaction time mainly depends on the reaction temperature, starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 30 minutes to 1 hour
2 hours.

【０１４６】Ｂ−７工程工程Ｂ−７は、工程Ｂ−５により製造した化合物（Ｉ
ｂ）において、Ｒ^2bが更にＲ^2cに変換可能な基である場
合、適当な試薬と反応させることにより、本発明に含ま
れる化合物（Ｉｃ）を得る工程である。[0146] B-7. Step B-7, the compound prepared by a process B-5 (I
In b), when R ^2b is a group that can be further converted to R ^2c , this is a step of obtaining a compound (Ic) included in the present invention by reacting with an appropriate reagent.

【０１４７】本工程で使用される反応試薬と反応条件
は、Ｒ^2bの変換反応の種類により変わりうる。The reaction reagents and reaction conditions used in this step can vary depending on the type of the R ^2b conversion reaction.

【０１４８】Ｒ^2bが、基ＣＨ₂ ＯＨ又は基ＣＨ₂ ＣＨ₂
ＯＨである化合物（Ｉｂ）において、本工程を適用する
ことができ、Ｒ^2cが基ＣＨ₂ ＯＣＯＲ⁷ 、基ＣＨ₂ ＣＨ
₂ ＯＣＯＲ⁷ 、基ＣＨ₂ ＯＲ⁷ 又は基ＣＨ₂ ＣＨ₂ ＯＲ
⁷ である化合物を製造することができる。R ^2b is a group CH ₂ OH or a group CH ₂ CH ₂
This step can be applied to the compound (Ib) which is OH, wherein R ^2c is a group CH ₂ OCOR ^{7 or} a group CH ₂ CH
₂ OCOR ⁷ , group CH ₂ OR ⁷ or group CH ₂ CH ₂ OR
⁷ can be prepared.

【０１４９】本反応は、Ｒ^2cが基ＣＨ₂ ＯＣＯＲ⁷ 又は
基ＣＨ₂ ＣＨ₂ ＯＣＯＲ⁷ である場合、通常エステル化
反応として知られている反応であり、工程Ｂ−４に準じ
て行なうことができる。When R ^2c is a group CH ₂ OCOR ⁷ or a group CH ₂ CH ₂ OCOR ⁷ , this reaction is a reaction generally known as an esterification reaction, and can be carried out according to Step B-4. it can.

【０１５０】本反応は、Ｒ^2cが基ＣＨ₂ ＯＲ⁷ 又はＣＨ
₂ ＣＨ₂ ＯＲ⁷ である場合、通常エーテル交換反応とし
て知られている反応であり、例えば、酸性の反応助剤の
存在下、過剰のＲ⁷ ＯＨを用いることにより行われる。In this reaction, R ^2c is a group of CH ₂ OR ⁷ or CH ₂
_{In the case of 2} CH ₂ OR ⁷ , this is a reaction generally known as a transesterification reaction, and is carried out, for example, by using an excess of R ⁷ OH in the presence of an acidic reaction auxiliary.

【０１５１】そのような反応助剤としては、例えば塩
酸、硫酸などの無機酸、四塩化チタン、三フッ化ホウ素
エーテル錯体、ジクロロ亜鉛などのルイス酸、及びトリ
フルオロ酢酸、トリフルオロメタンスルホン酸、ｐ−ト
ルエンスルホン酸などの有機酸等であり、好適には塩酸
のような無機酸である。Examples of such reaction assistants include inorganic acids such as hydrochloric acid and sulfuric acid, Lewis acids such as titanium tetrachloride, boron trifluoride ether complex and dichlorozinc, trifluoroacetic acid, trifluoromethanesulfonic acid, An organic acid such as toluenesulfonic acid, and preferably an inorganic acid such as hydrochloric acid.

【０１５２】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；アセトニトリルのようなニト
リル類；酢酸エチルのようなエステル類；塩化メチレ
ン、クロロホルム、ジクロルエタンのようなハロゲン化
炭化水素類；ジエチルエーテル、テトラヒドロフラン、
ジオキサンのようなエーテル類；トルエンのような芳香
族炭化水素類及びこれらの混合溶剤を挙げることができ
る。The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent, but is preferably water; nitriles such as acetonitrile; Esters; halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane; diethyl ether, tetrahydrofuran,
Examples include ethers such as dioxane; aromatic hydrocarbons such as toluene; and mixed solvents thereof.

【０１５３】反応温度は、通常−１０℃乃至１００℃で
あり、好適には、０℃乃至４０℃である。The reaction temperature is usually from -10 ° C to 100 ° C, preferably from 0 ° C to 40 ° C.

【０１５４】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、１０分乃至６
時間である。The reaction time mainly depends on the reaction temperature, the starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 10 minutes to 6 hours
Time.

【０１５５】Ｒ^2bが、基ＣＨ₂ Ｏ（テトラヒドロピラン
−２−イル）又は基ＣＨ₂ ＣＨ₂ Ｏ（テトラヒドロピラ
ン−２−イル）のような保護されたアルコールである化
合物（Ｉｂ）においても、本工程を適用することがで
き、Ｒ^2cが、基ＣＨ₂ ＯＨ又は基ＣＨ₂ ＣＨ₂ ＯＨであ
る化合物（Ｉｃ）を得ることができる。In the compound (Ib) wherein R ^2b is a protected alcohol such as the group CH ₂ O (tetrahydropyran-2-yl) or the group CH ₂ CH ₂ O (tetrahydropyran-2-yl), This step can be applied to obtain a compound (Ic) in which R ^2c is a group CH ₂ OH or a group CH ₂ CH ₂ OH.

【０１５６】本反応は、通常保護されたアルコールの脱
保護反応として知られている反応であり、例えば、酸性
又は塩基性の反応助剤の存在下行われるが、好適には、
酸性の反応助剤である。そのような反応助剤としては、
例えば塩酸、硫酸などの無機酸、四塩化チタン、三フッ
化ホウ素エーテル錯体、ジクロロ亜鉛などのルイス酸、
及びトリフルオロ酢酸、トリフルオロメタンスルホン
酸、ｐ−トルエンスルホン酸などの有機酸等であり、好
適には有機酸である。This reaction is a reaction generally known as a deprotection reaction of a protected alcohol. For example, the reaction is carried out in the presence of an acidic or basic reaction auxiliary.
It is an acidic reaction aid. Such reaction aids include:
For example, hydrochloric acid, inorganic acids such as sulfuric acid, titanium tetrachloride, boron trifluoride ether complex, Lewis acids such as dichlorozinc,
And organic acids such as trifluoroacetic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid, and are preferably organic acids.

【０１５７】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；メタノール、エタノール、ｔ
−ブタノールのようなアルコール類；アセトン、メチル
イソブチルケトンのようなケトン類；アセトニトリルの
ようなニトリル類；酢酸エチルのようなエステル類；塩
化メチレン、クロロホルム、ジクロルエタンのようなハ
ロゲン化炭化水素類；ジエチルエーテル、テトラヒドロ
フラン、ジオキサンのようなエーテル類；トルエンのよ
うな芳香族炭化水素類；ジメチルホルムアミド、ジメチ
ルアセトアミドのようなアミド類、ジメチルスルホキシ
ドのようなスルホキシド類等、及びこれらの混合溶剤を
挙げることができる。The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Preferably, the solvent is water; methanol, ethanol, t
Alcohols such as butanol; ketones such as acetone and methyl isobutyl ketone; nitriles such as acetonitrile; esters such as ethyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; diethyl. Ethers such as ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as toluene; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethylsulfoxide; and mixed solvents thereof. it can.

【０１５８】反応温度は、通常−１０℃乃至１００℃で
あり、好適には、０℃乃至４０℃である。The reaction temperature is usually from -10 ° C to 100 ° C, preferably from 0 ° C to 40 ° C.

【０１５９】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、１０分乃至６
時間である。The reaction time mainly depends on the reaction temperature, the starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 10 minutes to 6 hours
Time.

【０１６０】工程Ｂで、基ＡＨの保護化をＢ−１工程で
示し、また基ＡＲ^10a の脱保護化をＢ−６工程で示した
のは、化合物（ＩＩａ）を製造するのに最も一般的な方
法であると考えられるからである。従って、Ｂ−２工程
で示したベンゼン環へのニトロ化、Ｂ−３工程で示した
ニトロ基からアミノ基への還元、Ｂ−４工程で示したア
ミノ基のアシル化又はカルバマート化、及びＢ−５工程
で示したアシル基又はカルバマート基の窒素原子への置
換基の導入の各反応にとって特に問題がない限り、基Ａ
Ｈの保護化、脱保護化は任意の段階で行なうことがで
き、場合によっては何ら保護を必要としない場合もあ
る。化合物（ＩＩａ）の製造方法は、それらの方法の全
てを包含するものである。[0160] In step B, the shows the protected group AH in Step B-1, also showed deprotection of group AR ^10a in B-6 step, most commonly for the production of compound (IIa) This is because it is considered to be a typical method. Accordingly, nitration to a benzene ring shown in Step B-2, reduction of a nitro group to an amino group shown in Step B-3, acylation or carbamate formation of an amino group shown in Step B-4, and B Unless there is a particular problem for each reaction of introducing a substituent to a nitrogen atom of an acyl group or a carbamate group shown in Step -5, the group A
The protection and deprotection of H can be performed at any stage, and in some cases, no protection is required. The method for producing compound (IIa) encompasses all of those methods.

【０１６１】さらに、Ｂ−６工程の原料である化合物
（ＶＩＩＩ）のうち、Ｒ¹⁰が基Ｃ（＝Ｘ）Ｒ¹ である化
合物は、対応する４−アミノフェノール又は４−アミノ
チオフェノールのアミノ基及び基ＡＨを、同時に直接反
応することによっても製造することができる。この反応
は、Ｂ−４工程に準じて行なうことができるが、Ｒ¹ Ｃ
（＝Ｘ）Ｌ² で表される化合物は出発物質に対して２当
量以上添加する必要がある。Further, among the compounds (VIII), which are the starting materials for the step B-6, those in which R ¹⁰ is a group C (＝ X) R ¹ are those of the corresponding 4-aminophenol or 4-aminothiophenol The group and the group AH can also be produced by simultaneously reacting directly. This reaction can be carried out according to B-4 step, R ¹ C
The compound represented by (= X) L ² needs to be added in an amount of 2 equivalents or more based on the starting material.

【０１６２】（工程Ｃ）(Step C)

【０１６３】[0163]

【化１３】 Embedded image

【０１６４】上記工程中、Ｒ⁶ 、Ｑ及びｍは、前記と同
意義を示し、Ｚ¹ は、塩素原子、臭素原子又は沃素原子
を示す。In the above process, R ⁶ , Q and m have the same meaning as described above, and Z ¹ represents a chlorine atom, a bromine atom or an iodine atom.

【０１６５】Ｃ−１工程Ｃ−１工程は、ベンゾチアゾール又はベンゾオキサゾー
ルの２位がメチル基の化合物（Ｘ）をハロゲン化するこ
とにより、２位がハロメチル基である化合物（ＩＩＩ
ｂ）を製造する工程である。化合物（ＩＩＩｂ）は、前
記した工程Ａの出発物質である。 Step C-1 Step C-1 is a step of halogenating the compound (X) in which the 2-position of benzothiazole or benzoxazole is a methyl group to form a compound (III) in which the 2-position is a halomethyl group.
This is the step of manufacturing b). Compound (IIIb) is the starting material for step A described above.

【０１６６】本工程は、溶媒の存在下又は非存在下、場
合によりラジカル開始剤の存在下、化合物（Ｘ）を、ハ
ロゲン化剤と反応することにより行なわれる。This step is carried out by reacting compound (X) with a halogenating agent in the presence or absence of a solvent, optionally in the presence of a radical initiator.

【０１６７】使用されるハロゲン化剤としては、塩素分
子、臭素分子、Ｎ−クロロスクシンイミド、Ｎ−ブロモ
スクシンイミド、Ｎ−ヨードスクシンイミドなどを挙げ
ることができる。Examples of the halogenating agent to be used include chlorine molecules, bromine molecules, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide and the like.

【０１６８】使用されるラジカル開始剤としてはジベン
ゾイルパーオキサイド（ＢＰＯ）、アゾビスイソブチロ
ニトリル（ＡＩＢＮ）などを挙げることができる。Examples of the radical initiator used include dibenzoyl peroxide (BPO) and azobisisobutyronitrile (AIBN).

【０１６９】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；四塩化炭素、塩化メチレン、
クロロホルム、ジクロルエタンのようなハロゲン化炭化
水素類；酢酸；ジメチルホルムアミド（ＤＭＦ）を挙げ
ることができる。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. Preferably, the solvent is water;
Halogenated hydrocarbons such as chloroform and dichloroethane; acetic acid; dimethylformamide (DMF).

【０１７０】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、−１０℃乃至１００℃である。The reaction temperature is usually -90 ° C to 200 ° C, preferably -10 ° C to 100 ° C.

【０１７１】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常３０分乃至１００時間であり、好適には、１時間乃
至５０時間である。The reaction time mainly depends on the reaction temperature, the starting compound,
Depending on the type of reaction reagent and solvent used,
It is usually from 30 minutes to 100 hours, preferably from 1 hour to 50 hours.

【０１７２】本工程の出発物質である２−メチル化合物
（Ｘ）は、J.Org.Chem., 39, 3277(1974)、J.Org.Che
m., 43, 2296 (1978)及びJ.Chem.Soc.Perkin Trans 2,
1582(1972)に記載の方法に準じて製造することができ
る。The 2-methyl compound (X) as a starting material in this step was prepared according to J. Org. Chem., 39 , 3277 (1974), J. Org.
m., 43 , 2296 (1978) and J. Chem. Soc. Perkin Trans 2,
It can be produced according to the method described in 1582 (1972).

【０１７３】又、本工程の目的化合物（ＩＩＩａ）は、
Synthetic Communications, 19, 2921 (1989) 、J.Med.
Chem., 35, 457 (1992) 、J. Med. Chem., 35, 3792 (1
992)及びSynthesis, 102 (1979) に記載の方法に準じて
製造することもできる。The target compound (IIIa) of this step is
Synthetic Communications, 19 , 2921 (1989), J. Med.
Chem., 35 , 457 (1992), J. Med.Chem., 35 , 3792 (1
992) and Synthesis, 102 (1979).

【０１７４】（Ｄ工程）(Step D)

【０１７５】[0175]

【化１４】 Embedded image

【０１７６】上記式中、Ｒ⁴ 、Ｒ⁵ 、Ｒ⁶ 、Ｑ、ｍ及び
Ｒ⁹ は、前記と同意義を示し、Ｒ¹¹は、Ｃ１〜Ｃ６アル
キル基を示し、Ｒ^4a及びＲ^5aは、それぞれ同一又は異な
って、Ｃ１〜Ｃ６アルキル基を示す。In the above formula, R ⁴ , R ⁵ , R ⁶ , Q, m and R ⁹ are as defined above, R ¹¹ is a C1-C6 alkyl group, and R ^4a and R ^5a are The same or different, and each represents a C1 to C6 alkyl group.

【０１７７】Ｄ−１工程Ｄ−１工程は、ベンゾチアゾール環又はベンゾオキサゾ
ール環の２位ニトリル化合物（ＸＩ）を、式Ｒ¹¹ＯＨ
（Ｒ¹¹は前記と同意義を示す。）で表されるアルコール
化合物（例えば、メタノール、エタノール）の存在下、
加水分解し、ベンゾチアゾール環又はベンゾオキサゾー
ル環の２位アルコキシカルボニル化合物（ＸＩＩ）を製
造する工程である。 Step D-1 Step D-1 is a step of converting a 2-position nitrile compound (XI) having a benzothiazole ring or a benzoxazole ring into a compound of the formula R ¹¹ OH
(R ¹¹ is as defined above) in the presence of an alcohol compound (eg, methanol, ethanol).
This is a step for producing a 2-position alkoxycarbonyl compound (XII) having a benzothiazole ring or a benzoxazole ring by hydrolysis.

【０１７８】本工程は、アルコール化合物（Ｒ¹¹ＯＨ）
及び酸の存在下、化合物（ＸＩ）を加水分解することに
よって行なうことができる。In this step, the alcohol compound (R ¹¹ OH)
And hydrolysis of compound (XI) in the presence of an acid.

【０１７９】使用される酸としては、例えば、塩酸、硫
酸のような無機酸；ｐ−トルエンスルホン酸のような有
機酸等を挙げることができる。Examples of the acid used include inorganic acids such as hydrochloric acid and sulfuric acid; and organic acids such as p-toluenesulfonic acid.

【０１８０】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好ましくは、メタノール、エタノールのよう
なアルコール類を挙げることができる。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but preferably includes alcohols such as methanol and ethanol.

【０１８１】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、０℃乃至１００℃である。The reaction temperature is usually -90 ° C to 200 ° C, preferably 0 ° C to 100 ° C.

【０１８２】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常１分乃至１２時間であり、好適には、２分乃至６時
間である。The reaction time mainly depends on the reaction temperature, the starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 1 minute to 12 hours, preferably 2 minutes to 6 hours.

【０１８３】本工程の出発物質である２−シアノベンゾ
チアゾール化合物又は２−シアノベンゾオキサゾール化
合物（ＸＩ）は、J.Heterocyclic Chem., 29, 639 (199
2)に記載の方法に準じて製造することができる。The 2-cyanobenzothiazole compound or 2-cyanobenzoxazole compound (XI) as a starting material in this step was prepared according to the method described in J. Heterocyclic Chem., 29 , 639 (199).
It can be produced according to the method described in 2).

【０１８４】また、本工程の目的化合物（ＸＩＩ）は、
Synthetic Communication, 14, 947(1984) 及びTetrahe
dron Letters, 645 (1973) に記載の方法に準じて製造
することもできる。The target compound (XII) in this step is
Synthetic Communication, 14 , 947 (1984) and Tetrahe
It can also be produced according to the method described in dron Letters, 645 (1973).

【０１８５】Ｄ−２工程Ｄ−２工程は、Ｄ−１工程により製造される化合物（Ｘ
ＩＩ）のベンゾチアゾール環又はベンゾオキサゾール環
２位のアルコキシカルボニル基を還元し、ベンゾチアゾ
ール環又はベンゾオキサゾール環の２位がヒドロキシメ
チル基である化合物（ＸＩＩＩａ）を製造する工程であ
る。 Step D-2 Step D-2 is a step of preparing the compound (X
This is a step of reducing the alkoxycarbonyl group at the 2-position of the benzothiazole ring or benzoxazole ring in II) to produce a compound (XIIIa) in which the 2-position of the benzothiazole ring or the benzoxazole ring is a hydroxymethyl group.

【０１８６】本工程は、水素化ホウ素ナトリウム、水素
化ホウ素リチウムのような還元剤を用いて、通常エステ
ルを一級アルコールに還元する際の常法に従って行なう
ことができる。This step can be carried out using a reducing agent such as sodium borohydride or lithium borohydride, according to a usual method for reducing an ester to a primary alcohol.

【０１８７】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、メタノール、エタノールのようなアルコール
類を挙げることができる。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent, and examples thereof include alcohols such as methanol and ethanol.

【０１８８】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、−２０℃乃至８０℃である。The reaction temperature is usually from -90 ° C to 200 ° C, preferably from -20 ° C to 80 ° C.

【０１８９】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、１０分乃至１
２時間である。The reaction time mainly depends on the reaction temperature, the starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 10 minutes to 1 hour
2 hours.

【０１９０】又、本工程の目的化合物（ＸＩＩＩａ）
は、Helvetica Chimica Acta, 55, 1782 (1972) に記載
の方法に準じて製造することもできる。The target compound (XIIIa) of this step
Can also be produced according to the method described in Helvetica Chimica Acta, 55 , 1782 (1972).

【０１９１】Ｄ−３工程Ｄ−３工程は、Ｄ−２工程により製造される２−ヒドロ
キシメチルベンゾチアゾール化合物又は２−ヒドロキシ
メチルベンゾオキサゾール化合物（ＸＩＩＩａ）の２位
ヒドロキシメチル基をホルミル基に酸化して、２−ホル
ミルベンゾチアゾール化合物又は２−ホルミルベンゾオ
キサゾール化合物（ＸＩＶ）を得る工程である。 Step D-3 In the step D-3, the 2-hydroxymethyl group of the 2-hydroxymethylbenzothiazole compound or the 2-hydroxymethylbenzoxazole compound (XIIIa) produced in the step D-2 is oxidized to a formyl group. To obtain a 2-formylbenzothiazole compound or a 2-formylbenzoxazole compound (XIV).

【０１９２】本工程は、例えば、Swern 酸化、Jones 酸
化などのような、ヒドロキシメチル基をホルミル基に酸
化する際の常法に従って、行なうことができる。This step can be performed according to a conventional method for oxidizing a hydroxymethyl group to a formyl group, such as Swern oxidation or Jones oxidation.

【０１９３】又、本工程の目的化合物（ＸＩＶ）は、Li
ebigs.Ann.Chem., 542 (1980) に記載の方法に準じて製
造することもできる。The target compound (XIV) in this step is Li
It can also be produced according to the method described in ebigs.Ann.Chem., 542 (1980).

【０１９４】Ｄ−４工程Ｄ−４工程は、Ｄ−３工程により製造される２−ホルミ
ルベンゾチアゾール化合物又は２−ホルミルベンゾオキ
サゾール化合物（ＸＩＶ）を、Ｒ^4aＭｇＺ¹ で表される
グリニャール試薬（式中、Ｚ¹ は、塩素原子、臭素原子
及び沃素原子を示す。）と反応させることにより、化合
物（ＸＩＩＩｂ）を製造する工程である。 Step D-4 In step D-4, the 2-formylbenzothiazole compound or 2-formylbenzoxazole compound (XIV) produced in step D-3 is converted to a Grignard reagent represented by R ^4a MgZ ¹ ( In the formula, Z ¹ represents a chlorine atom, a bromine atom and an iodine atom) to produce a compound (XIIIb).

【０１９５】本工程は、通常のグリニャール反応の方法
に従って行なうことができる。This step can be carried out according to a usual Grignard reaction method.

【０１９６】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、ジエチルエーテル、テトラヒドロフラン、ジ
オキサンのようなエーテル類を挙げることができる。The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. Examples thereof include ethers such as diethyl ether, tetrahydrofuran and dioxane.

【０１９７】反応温度は、通常−１００℃乃至１００℃
であり、好適には、−４０℃乃至５０℃である。The reaction temperature is usually from -100 ° C to 100 ° C.
, Preferably -40 ° C to 50 ° C.

【０１９８】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、１０分乃至１
２時間である。The reaction time mainly depends on the reaction temperature, the starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 10 minutes to 1 hour
2 hours.

【０１９９】Ｄ−５工程Ｄ−５工程は、Ｄ−１工程により製造される２−アルコ
キシカルボニルベンゾチアゾール化合物又は２−アルコ
キシカルボニルベンゾオキサゾール化合物（ＸＩＩ）
を、Ｒ^4aＭｇＸで表されるグリニャール試薬及びＲ^5aＭ
ｇＸで表されるグリニャール試薬（式中、Ｒ⁴ 、Ｒ⁵ 及
びＸは前記と同意義を示す。）と反応させることによ
り、化合物（ＸＩＩＩｃ）を製造する工程である。 Step D-5 Step D-5 is a 2-alkoxycarbonylbenzothiazole compound or 2-alkoxycarbonylbenzoxazole compound (XII) produced in Step D-1
With a Grignard reagent represented by R ^4a MgX and R ^5a M
This is a step of producing a compound (XIIIc) by reacting with a Grignard reagent represented by gX (wherein R ⁴ , R ⁵ and X have the same meanings as described above).

【０２００】本工程は、Ｄ−４工程に準じて行なうこと
ができる。This step can be carried out according to step D-4.

【０２０１】本工程においては、Ｒ^4aとＲ^5aが同一の場
合は出発物質に対してグリニャール試薬を２当量以上、
Ｒ^4aとＲ^5aが異なる場合は２種類のグリニャール試薬を
それぞれ１当量以上ずつ添加することが望ましい。In this step, when R ^4a and R ^5a are the same, 2 or more equivalents of the Grignard reagent to the starting material are used.
When R ^4a and R ^5a are different, it is desirable to add two or more Grignard reagents each in an amount of 1 equivalent or more.

【０２０２】Ｄ−６工程Ｄ−６工程は、Ｄ−２工程、Ｄ−４工程及びＤ−５工程
によりそれぞれ製造される化合物（ＸＩＩＩａ）、（Ｘ
ＩＩＩｂ）及び（ＸＩＩＩｃ）を原料として用いて、一
般式Ｒ⁹ Ｌ⁴ で表される化合物［式中、Ｒ⁹ は前記と同
意義を示し、Ｌ⁴ は脱離基（ここで脱離基とは、通常求
核残基として脱離する基のことをいい、好適には、塩素
原子、臭素原子、沃素原子のようなハロゲン原子であ
る。）を示す。］と反応させ、水酸基をスルホニル化又
はホスフィニル化することにより、脱離基である−ＯＲ
⁹ 基を有する化合物（ＩＩＩｂ）を製造する工程であ
る。 Step D-6 Step D-6 is a compound of the formula (XIIIa), (XIIIa) or (XIIIa) produced by Steps D-2, D-4 and D-5, respectively.
IIIb) and (XIIIc) as starting materials, a compound represented by the general formula R ⁹ L ⁴ wherein R ⁹ has the same meaning as described above, and L ⁴ is a leaving group (here, leaving group Represents a group which usually leaves as a nucleophilic residue, and is preferably a halogen atom such as a chlorine atom, a bromine atom and an iodine atom.) And sulfonylation or phosphinylation of the hydroxyl group to form a leaving group -OR.
^This is a step for producing a compound (IIIb) having ⁹ groups.

【０２０３】本工程は、溶媒の存在下、必要により塩基
存在下で行われる。This step is carried out in the presence of a solvent, if necessary, in the presence of a base.

【０２０４】使用される塩基としては、水酸化ナトリウ
ム、水酸化カリウムのようなアルカリ金属水酸化物；炭
酸ナトリウム、炭酸カリウムのようなアルカリ金属炭酸
塩；ナトリウムメトキシド、ナトリウムエトキシド、カ
リウムｔ−ブトキシドのような金属アルコキシド；水素
化ナトリウム、水素化カリウムのようなアルカリ金属水
素化物；トリエチルアミン、トリｎ−ブチルアミン、ジ
イソプロピルエチルアミンのような脂肪族三級アミン
類；Ｎ，Ｎ−ジメチルアニリン、Ｎ，Ｎ−ジエチルアニ
リンのような三級アニリン類；１，４−ジアザビシクロ
［２．２．２］オクタン（ＤＡＢＣＯ）、１，８−ジア
ザビシクロ［５．４．０］ウンデセ−７−エン（ＤＢ
Ｕ）のような脂肪族環状三級アミン類；ピリジン、コリ
ジン、４−（Ｎ，Ｎ−ジメチルアミノ）ピリジンのよう
なピリジン類；ｎ−ブチルリチウム、ｓ−ブチルリチウ
ム、リチウムジイソプロピルアミド、ナトリウムビ
ストリメチルシリルアミド、リチウムビストリメチル
シリルアミドのような有機金属塩基類等を挙げることが
できる。Examples of the base to be used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium methoxide, sodium ethoxide and potassium t-oxide. Metal alkoxides such as butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; aliphatic tertiary amines such as triethylamine, tri-n-butylamine and diisopropylethylamine; N, N-dimethylaniline; Tertiary anilines such as N-diethylaniline; 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [5.4.0] undec-7-ene (DB
Aliphatic cyclic tertiary amines such as U); pyridines such as pyridine, collidine, 4- (N, N-dimethylamino) pyridine; n-butyllithium, s-butyllithium, lithium diisopropylamide, sodium bis Organometallic bases such as trimethylsilylamide and lithium bistrimethylsilylamide can be exemplified.

【０２０５】使用される溶媒としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、水；アセトン、メチルイソブチル
ケトンのようなケトン類；アセトニトリルのようなニト
リル類；酢酸エチルのようなエステル類；塩化メチレ
ン、クロロホルム、ジクロルエタンのようなハロゲン化
炭化水素類；ジエチルエーテル、テトラヒドロフラン、
ジオキサンのようなエーテル類；トルエンのような芳香
族炭化水素類、及びこれらの混合溶剤を挙げることがで
きる。The solvent used is not particularly limited as long as it does not hinder the reaction and dissolves the starting materials to some extent, but is preferably water; ketones such as acetone and methyl isobutyl ketone; acetonitrile Nitrates; ethyl acetate; halogenated hydrocarbons, such as methylene chloride, chloroform, dichloroethane; diethyl ether, tetrahydrofuran,
Examples include ethers such as dioxane; aromatic hydrocarbons such as toluene; and mixed solvents thereof.

【０２０６】反応温度は、通常−９０℃乃至２００℃で
あり、好適には、−２０℃乃至１００℃である。The reaction temperature is usually -90 ° C to 200 ° C, preferably -20 ° C to 100 ° C.

【０２０７】反応時間は、主に反応温度、原料化合物、
反応試薬及び使用される溶媒の種類によって異なるが、
通常５分乃至２４時間であり、好適には、１５分乃至６
時間である。The reaction time mainly depends on the reaction temperature, the starting compound,
Depending on the type of reaction reagent and solvent used,
Usually 5 minutes to 24 hours, preferably 15 minutes to 6 hours
Time.

【０２０８】工程Ｄ−７Ｄ−７工程は、Ｄ−２工程、Ｄ−４工程及びＤ−５工程
によりそれぞれ製造される化合物（ＸＩＩＩａ）、（Ｘ
ＩＩＩｂ）及び（ＸＩＩＩｃ）を原料として用いて、化
合物（ＸＩＶ）［式中、Ｒ³ 及びｎは前記と同意義を示
し、Ｚ⁴ は、弗素原子、塩素原子又は臭素原子を示
す。］と反応させることにより、Ａが酸素原子である化
合物（ＶＩａ）［式中、Ｒ³ 、Ｒ⁴ 、Ｒ⁵ 、Ｒ⁶ 、ｍ及
びｎは、前記と同意義を示す。］を製造する工程であ
る。 Step D-7 Step D-7 is a compound of the formula (XIIIa) (XIIIa) or (XIIIa) which is produced respectively by steps D-2, D-4 and D-5.
Using compound (IIIb) and (XIIIc) as raw materials, compound (XIV) wherein R ³ and n have the same meanings as described above, and Z ⁴ represents a fluorine atom, a chlorine atom or a bromine atom. And a compound (VIa) wherein A is an oxygen atom, wherein R ³ , R ⁴ , R ⁵ , R ⁶ , m and n have the same meaning as described above. ] Is a process of manufacturing.

【０２０９】本工程は、工程Ｄ−６の条件に準じて行な
うことができる。This step can be performed according to the conditions of step D-6.

【０２１０】上記の工程Ａ及びＢにおいては、Ｂ−２工
程で示したベンゼン環へのニトロ化、Ｂ−３工程で示し
たニトロ基からアミノ基への還元、Ｂ−４工程で示した
アミノ基のアシル化又はカルバマート化及びＢ−５工程
で示したアミド基又はカルバマート基の窒素原子への置
換基の導入の後に、化合物（ＩＩ）と化合物（ＩＩＩ）
との縮合反応を行なう記載となっているが、特に問題が
ない限り、化合物（ＩＩ）と（ＩＩＩ）との縮合反応は
任意の段階で行なうことができる。すなわち、上記の工
程はニトロ化→還元→アシル化又はカルバマート化→ア
ミド基又はカルバマート基への置換基の導入→（ＩＩ
Ｉ）との縮合と簡略化することができるが、例えば、ニ
トロ化→還元→（ＩＩＩ）との縮合→アシル化又はカル
バマート化→アミド基又はカルバマート基への置換基の
導入という工程、ニトロ化→（ＩＩＩ）との縮合→還元
→アシル化又はカルバマート化→アミド基又はカルバマ
ート基への置換基の導入という工程、（ＩＩＩ）との縮
合→ニトロ化→還元→アシル化又はカルバマート化→ア
ミド基又はカルバマート基への置換基の導入という工程
等の順序で行なうこともできる。本願化合物の製造方法
は、それらの方法の全てを包含するものである。In the above steps A and B, the nitration to the benzene ring shown in step B-2, the reduction of the nitro group to the amino group shown in step B-3, and the amino group shown in step B-4 After the acylation or carbamate of the group and the introduction of a substituent to the nitrogen atom of the amide or carbamate group shown in step B-5, compound (II) and compound (III)
Is described, but the condensation reaction between compounds (II) and (III) can be carried out at any stage, unless otherwise specified. That is, the above-mentioned step is performed by nitration → reduction → acylation or carbamate → introduction of a substituent to an amide group or a carbamate group → (II
The condensation with I) can be simplified, for example, a step of nitration → reduction → condensation with (III) → acylation or carbamate → introduction of a substituent to an amide group or a carbamate group, → condensation with (III) → reduction → acylation or carbamate → introduction of a substituent to an amide group or carbamate group; condensation with (III) → nitration → reduction → acylation or carbamate → amide group Alternatively, they can be carried out in the order of a step of introducing a substituent into a carbamate group. The method for producing the compound of the present invention includes all of those methods.

【０２１１】上記各反応工程終了後、各工程の目的化合
物は常法に従って反応混合物から採取することができ
る。例えば、反応混合物を適宜中和し、又、不溶物が存
在する場合には濾過により除去した後、水と混和しない
有機溶媒を加え、水洗後、溶剤を留去することによって
得られる。得られた目的化合物は必要ならば、常法、例
えば再結晶、再沈殿又はクロマトグラフィ−等によって
更に精製できる。After completion of each of the above reaction steps, the target compound of each step can be collected from the reaction mixture according to a conventional method. For example, it can be obtained by appropriately neutralizing the reaction mixture, removing any insoluble matter by filtration, adding an organic solvent immiscible with water, washing with water, and distilling off the solvent. If necessary, the obtained target compound can be further purified by a conventional method, for example, recrystallization, reprecipitation or chromatography.

【０２１２】本発明の化合物は、担体及び必要に応じて
他の補助剤（界面活性剤等）と混合して、除草剤として
通常用いられる製剤形態、例えば粉剤、粗粉剤、粒剤、
顆粒剤、水和剤、水溶剤、乳剤、液剤等に調製して使用
される。ここでいう担体とは、有効成分化合物の植物へ
の到達性を助け又は有効成分の貯蔵、輸送若しくは取り
扱いを容易にするために除草剤中に混合される、合成又
は天然の無機又は有機物質を意味する。The compound of the present invention may be mixed with a carrier and, if necessary, other adjuvants (surfactants and the like) to prepare a preparation usually used as a herbicide, for example, powder, coarse powder, granule,
It is prepared and used in granules, wettable powders, aqueous solvents, emulsions, liquids and the like. A carrier as used herein refers to a synthetic or natural inorganic or organic substance that is mixed into a herbicide to help the active ingredient compound reach plants or to facilitate storage, transport or handling of the active ingredient. means.

【０２１３】適当な固体担体としては、例えば、カオリ
ナイト群、モンモリロナイト群、アタパルジャイト群等
で代表されるクレー類、タルク、雲母、葉ロウ石、軽
石、バーミキュライト、石膏、ドロマイト、けいそう
土、マグネシウム石灰、燐石灰、ゼオライト、無水ケイ
酸、合成ケイ酸カルシウム、カオリン、ベントナイト、
炭酸カルシウム等の無機物質、大豆粉、タバコ粉、クル
ミ粉、小麦粉、木粉、澱粉、結晶セルロース等の植物性
有機物質、クマロン樹脂、石油樹脂、アルキド樹脂、ポ
リ塩化ビニル、ポリアルキレングリコール、ケトン樹
脂、エステルガム、コーパルガム、ダンマルガム等の合
成又は天然の高分子化合物、カルナバロウ、パラフィン
ロウ、蜜ロウ等のワックス類或は尿素等を挙げることが
できる。Suitable solid carriers include, for example, clays represented by kaolinite group, montmorillonite group, attapulgite group, etc., talc, mica, phyllite, pumice, vermiculite, gypsum, dolomite, diatomaceous earth, magnesium Lime, phosphorous lime, zeolite, silicic anhydride, synthetic calcium silicate, kaolin, bentonite,
Inorganic substances such as calcium carbonate, soybean flour, tobacco flour, walnut flour, flour, wood flour, starch, vegetable organic substances such as crystalline cellulose, coumarone resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone Synthetic or natural polymer compounds such as resin, ester gum, copal gum, dammar gum, etc .; waxes such as carnauba wax, paraffin wax and beeswax; urea;

【０２１４】適当な液体担体としては、例えば、ケロシ
ン、鉱油、スピンドル油、ホワイトオイル等のパラフィ
ン系若しくはナフテン系炭化水素、ベンゼン、トルエ
ン、キシレン、エチルベンゼン、クメン、メチルナフタ
レン等の芳香族炭化水素、四塩化炭素、クロロホルム、
トリクロルエチレン、モノクロルベンゼン、クロルトル
エン等の塩素化炭化水素、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、
ジイソブチルケトン、シクロヘキサノン、アセトフェノ
ン、イソホロン等のケトン類、酢酸エチル、酢酸アミ
ル、エチレングリコールアセテート、ジエチレングリコ
ールアセテート、マレイン酸ジブチル、コハク酸ジエチ
ル等のエステル類、メタノール、n-ヘキサノール、エチ
レングリコール、ジエチレングリコール、シクロヘキサ
ノール、ベンジルアルコール等のアルコール類、エチレ
ングリコールエチルエーテル、エチレングリコールフェ
ニルエーテル、ジエチレングリコールエチルエーテル、
ジエチレングリコールブチルエーテル等のエーテルアル
コール類、ジメチルホルムアミド、ジメチルスルホキシ
ド等の極性溶媒或は水等を挙げることができる。Suitable liquid carriers include, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil and white oil; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene and methylnaphthalene; Carbon tetrachloride, chloroform,
Chlorinated hydrocarbons such as trichloroethylene, monochlorobenzene, and chlorotoluene; ethers such as dioxane and tetrahydrofuran; acetone; methyl ethyl ketone;
Ketones such as diisobutyl ketone, cyclohexanone, acetophenone and isophorone, esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate and diethyl succinate, methanol, n-hexanol, ethylene glycol, diethylene glycol and cyclo Hexanol, alcohols such as benzyl alcohol, ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether,
Examples thereof include ether alcohols such as diethylene glycol butyl ether, polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

【０２１５】乳化、分散、湿潤、拡展、結合、崩壊性調
節、有効成分安定化、流動性改良、防錆、植物への吸収
促進等の目的で使用される界面活性剤は、イオン性でも
非イオン性でもよい。Surfactants used for the purpose of emulsification, dispersion, wetting, spreading, binding, control of disintegration, stabilization of active ingredients, improvement of fluidity, rust prevention, promotion of absorption into plants, etc. may be ionic. It may be non-ionic.

【０２１６】適当な非イオン性界面活性剤としては、例
えば、脂肪酸の蔗糖エステル、ラウリルアルコール、ス
テアリルアルコール、オレイルアルコール等の高級脂肪
族アルコールの酸化エチレン重合付加物、イソオクチル
フェノール、ノニルフェノール等のアルキルフェノール
の酸化エチレン重合付加物、ブチルナフトール、オクチ
ルナフトール等のアルキルナフトールの酸化エチレン重
合付加物、パルミチン酸、ステアリン酸、オレイン酸等
の高級脂肪酸の酸化エチレン重合付加物、ステアリル燐
酸ジラウリル燐酸等のモノ若しくはジアルキル燐酸の酸
化エチレン重合付加物、ドデシルアミン、ステアリン酸
アミド等の高級脂肪族アミンの酸化エチレン重合付加
物、ソルビタン等の多価アルコールの高級脂肪酸エステ
ル及びその酸化エチレン重合付加物並びに酸化エチレン
と酸化プロピレンの共重合体等を挙げることができる。Suitable nonionic surfactants include, for example, sucrose esters of fatty acids, ethylene oxide polymerization adducts of higher aliphatic alcohols such as lauryl alcohol, stearyl alcohol and oleyl alcohol, and alkylphenols such as isooctylphenol and nonylphenol. Polymerized adducts of ethylene oxide, ethylene oxide adducts of alkyl naphthols such as butyl naphthol and octyl naphthol, ethylene oxide polymer adducts of higher fatty acids such as palmitic acid, stearic acid and oleic acid, mono- and dialkyls such as stearyl phosphate dilauryl phosphate Polymerized ethylene oxide adducts of phosphoric acid, ethylene oxide adducts of higher aliphatic amines such as dodecylamine and stearamide, higher fatty acid esters of polyhydric alcohols such as sorbitan, and their oxidized oxides Copolymers of emissions polymerization adducts and ethylene oxide and propylene oxide can be cited.

【０２１７】適当な陰イオン性界面活性剤としては、例
えば、ラウリル硫酸ナトリウム、オレイルアルコール硫
酸エステルアミン塩等のアルキル硫酸エステル塩、スル
ホコハク酸ジオクチルエステルナトリウム、オレイン酸
ナトリウム、ステアリン酸ナトリウム等の脂肪酸塩類、
イソプロピルナフタレンスルホン酸ナトリウム、メチレ
ンビスナフタレンスルホン酸ナトリウム、リグニンスル
ホン酸ナトリウム、ドデシルベンゼンスルホン酸ナトリ
ウム等のアルキルアリールスルホン酸塩等を挙げること
ができる。Suitable anionic surfactants include, for example, alkyl sulfates such as sodium lauryl sulfate and amine salt of oleyl alcohol sulfate, and fatty acid salts such as sodium dioctyl sulfosuccinate, sodium oleate and sodium stearate. ,
Alkyl aryl sulfonates such as sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, sodium ligninsulfonate and sodium dodecylbenzenesulfonate can be mentioned.

【０２１８】適当な陽イオン性界面活性剤としては、例
えば、高級脂肪族アミン、第４級アンモニウム塩類、ア
ルキルピリジニウム塩類等を挙げることができる。Suitable cationic surfactants include, for example, higher aliphatic amines, quaternary ammonium salts, alkylpyridinium salts and the like.

【０２１９】さらに、本発明の除草剤には、製剤の性状
を改善し生物効果を高める目的で、他の成分として、例
えば、ゼラチン、アラビアゴム、カゼイン、アルブミ
ン、ニカワ、アルギン酸ソーダ、ポリビニルアルコー
ル、カルボキシメチルセルロース、メチルセルロース、
ヒドロキシメチルセルロース等の高分子化合物、ポリリ
ン酸ナトリウム、ベントナイト等のチキソトロピー剤及
びその他の補助剤を含有することもある。Further, the herbicide of the present invention may further contain other components such as gelatin, gum arabic, casein, albumin, glue, sodium alginate, polyvinyl alcohol, and the like, for the purpose of improving the properties of the preparation and enhancing the biological effect. Carboxymethylcellulose, methylcellulose,
It may contain a high molecular compound such as hydroxymethylcellulose, a thixotropic agent such as sodium polyphosphate, bentonite, and other auxiliary agents.

【０２２０】上記の担体及び種々の補助剤は製剤の剤型
適用場面を考慮して、目的に応じてそれぞれ単独に或は
組み合わされて適宜使用される。The above carriers and various auxiliaries are used singly or in combination as appropriate according to the purpose, taking into account the application of the dosage form of the preparation.

【０２２１】粉剤は有効成分化合物を通常２乃至１０重
量部含有し、残部は固体担体である。Dusts usually contain 2 to 10 parts by weight of an active ingredient compound, and the remainder is a solid carrier.

【０２２２】水和剤は有効成分を通常１０乃至８０重量
部含有し、残部は固体担体、分散湿潤剤であって、必要
に応じて保護コロイド剤、チキソトロピー剤、消泡剤等
が加えられる。The wettable powder usually contains 10 to 80 parts by weight of the active ingredient, and the balance is a solid carrier and a dispersing wetting agent. If necessary, a protective colloid agent, a thixotropic agent, an antifoaming agent and the like are added.

【０２２３】粒剤は有効成分化合物を通常０．１乃至１
０重量部含有し、残部は大部分が固体担体である。有効
成分化合物は固体担体と均一に混合されているか或は固
体担体の表面に均一に固着若しくは吸着されており、粒
の径は約０．２乃至１．５ｍｍ程度である。The granules usually contain the active ingredient compound in an amount of 0.1 to 1%.
It contains 0 parts by weight, and the balance is mostly solid carrier. The active ingredient compound is uniformly mixed with the solid carrier or is uniformly fixed or adsorbed on the surface of the solid carrier, and the diameter of the particles is about 0.2 to 1.5 mm.

【０２２４】乳剤は有効成分を通常１乃至５０重量部含
有しており、これに約５乃至２０重量部の乳剤が含ま
れ、残部は液体担体であり、必要に応じて防錆剤が加え
られる。The emulsion usually contains 1 to 50 parts by weight of the active ingredient, and contains about 5 to 20 parts by weight of the emulsion, the remainder being a liquid carrier, and if necessary, a rust inhibitor is added. .

【０２２５】このようにして種々の剤型に調製された本
発明の化合物を、例えば、水田において雑草の発芽前又
は発芽後に土壌処理するときは、１０ａあたり有効成分
として１ｇ乃至１０００ｇ好ましくは１０ｇ乃至３００
ｇを処理することにより、有効に雑草を駆除することが
できる。When the compound of the present invention thus prepared in various dosage forms is subjected to soil treatment before or after germination of weeds in a paddy field, for example, 1 g to 1000 g, preferably 10 g to 10 g as an active ingredient per 10 a 300
By treating g, weeds can be effectively controlled.

【０２２６】本発明の除草剤に対して、殺草スペクトラ
ムを広げるために他の除草剤が配合されることは好まし
く、場合によっては相乗効果を期待することもできる。The herbicide of the present invention is preferably blended with another herbicide in order to broaden the herbicidal spectrum, and in some cases, a synergistic effect can be expected.

【０２２７】本発明の除草剤は、もちろん他の植物成長
調節剤、殺菌剤、殺虫剤、殺ダニ剤、殺線虫剤或は肥料
等と混合して使用することができる。The herbicide of the present invention can of course be used in admixture with other plant growth regulators, fungicides, insecticides, acaricides, nematicides or fertilizers.

【０２２８】以下に本発明の実施例及び製剤例を示し具
体的に説明するが、本発明はこれらに限られるものでは
ない。The present invention will now be described in more detail with reference to Examples and Formulation Examples, but it should not be construed that the invention is limited thereto.

【０２２９】[0229]

【Example】

【０２３０】[0230]

【実施例１】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］アセトアミド（化合物番号Ａ１．１）（工程Ａ
−１）４−アセトアミドフェノール１３３．９ｍｇをジメチル
ホルムアミド（ＤＭＦ）２．７ｍｌに溶解後、６０％水
素化ナトリウム０．２４ｇを加えた。ついで２−ブロモ
メチルベンゾチアゾール２０５．６ｍｇの２ｍｌＤＭＦ
溶液を加え、室温にて７時間撹袢した。反応液を酢酸エ
チルで希釈後、水洗し、硫酸ナトリウムで乾燥した。ろ
過後、溶媒を減圧下留去し、シリカゲルカラムクロマト
グラフィー（溶出溶媒ヘキサン：酢酸エチル＝１：
２）で精製し、融点１６８〜１７０℃を有する標記化合
物２２１．１ｍｇ（収率８４％）を得た。Example 1 N- [4- (benzothiazol-2-ylmethoxy) phenyl
[Enyl] acetamide (Compound No. A1.1) (Step A
-1) After 133.9 mg of 4-acetamidophenol was dissolved in 2.7 ml of dimethylformamide (DMF), 0.24 g of 60% sodium hydride was added. Then 205.6 mg of 2-bromomethylbenzothiazole in 2 ml of DMF
The solution was added and stirred at room temperature for 7 hours. The reaction solution was diluted with ethyl acetate, washed with water, and dried over sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 1).
Purification in 2) gave 221.1 mg (84% yield) of the title compound having a melting point of 168-170 ° C.

【０２３１】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.03 (1H, d, J=7.4Hz), 7.90 (1H,d, J=6.9Hz), 7.55
-7.35 (2H, m), 7.42 (2H, d, J=9.0Hz), 7.07 (1H, b
r.s),7.00 (2H, d, J=9.0Hz), 5.47 (2H, s), 2.16 (3
H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.03 (1H, d, J = 7.4Hz), 7.90 (1H, d, J = 6.9Hz), 7.55
-7.35 (2H, m), 7.42 (2H, d, J = 9.0Hz), 7.07 (1H, b
rs), 7.00 (2H, d, J = 9.0Hz), 5.47 (2H, s), 2.16 (3
H, s).

【０２３２】[0232]

【実施例２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ) フ
ェニル］プロピオンアミド（化合物番号Ａ１．１８）（１）４−（ベンゾチアゾール−２−イルメトキシ）
アニリン（工程Ａ−１）４−アミノフェノール２．１７ｇを７０ｍｌのアセトン
に溶解し、それに２−ブロモメチルベンゾチアゾール
４．５６ｇと、次いで炭酸セシウム３．２５ｇを加え、
室温にて８．５時間撹拌した後、更に炭酸セシウム３．
２５ｇを加え４時間撹拌した。反応溶液をろ過し、ろ液
を減圧下濃縮した。得られた粗結晶をシリカゲルカラム
クロマトグラフィー（溶出溶媒ヘキサン：酢酸エチル
＝１：１〜３：２）で精製し、融点８７〜８９℃を有す
る標記化合物２．６７ｇ（収率５２％）を得た。Example 2 N- [4- (benzothiazol-2-ylmethoxy) phenyl
[Enyl] propionamide (Compound No. A1.18) (1) 4- (benzothiazol-2-ylmethoxy)
Aniline (Step A-1) 2.17 g of 4-aminophenol was dissolved in 70 ml of acetone, and 4.56 g of 2-bromomethylbenzothiazole and then 3.25 g of cesium carbonate were added thereto.
After stirring at room temperature for 8.5 hours, cesium carbonate was further added.
25 g was added and the mixture was stirred for 4 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The obtained crude crystals are purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 1 to 3: 2) to obtain 2.67 g (yield: 52%) of the title compound having a melting point of 87 to 89 ° C. Was.

【０２３３】ＮＭＲスペクトル(200MHz,CDCl₃+CD₃OD)
δppm: 8.00 (1H, d, J=7.5Hz), 7.92(1H, d, J=8.0H
z), 7.56-7.38 (3H, m), 6.89 (2H, br.d, J=9.0Hz),
6.70 (2H, br.d, J=9.0Hz), 5.41 (2H,s). （２）Ｎ−［４−（ベンゾチアゾール−２−イルメト
キシ) フェニル］プロピオンアミド（化合物番号Ａ１．
１８）（工程Ｂ−４）上記（１）の方法で製造された４−（ベンゾチアゾール
−２−イルメトキシ）アニリン１４９．１ｍｇを塩化メ
チレン６ｍｌに溶解後、氷水浴中、トリエチルアミン
０．０９ｍｌ、プロピオニルクロリド０．０６ｍｌを加
え、同温で３時間撹拌した。反応液中に水を加え、塩化
メチレンで抽出した。抽出液を水洗した後、硫酸ナトリ
ウムで乾燥し、ろ過後、溶媒を減圧下留去し、シリカゲ
ルカラムクロマトグラフィー（溶出溶媒ヘキサン：酢
酸エチル＝１：２）で精製し、融点１８２℃を有する標
記化合物１６５．５ｍｇ（９１％）を得た。NMR spectrum (200 MHz, CDCl ₃ + CD ₃ OD)
δppm: 8.00 (1H, d, J = 7.5Hz), 7.92 (1H, d, J = 8.0H
z), 7.56-7.38 (3H, m), 6.89 (2H, br.d, J = 9.0Hz),
6.70 (2H, br.d, J = 9.0 Hz), 5.41 (2H, s). (2) N- [4- (benzothiazol-2-ylmethoate)
Xy) phenyl] propionamide (Compound No. A1.
18) (Step B-4) After dissolving 149.1 mg of 4- (benzothiazol-2-ylmethoxy) aniline prepared by the method of the above (1) in 6 ml of methylene chloride, 0.09 ml of triethylamine and propionyl in an ice water bath. Chloride (0.06 ml) was added, and the mixture was stirred at the same temperature for 3 hours. Water was added to the reaction solution, and extracted with methylene chloride. The extract was washed with water, dried over sodium sulfate, filtered, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 2). 165.5 mg (91%) of the compound were obtained.

【０２３４】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.03 (1H, d, J=7.7Hz), 7.90 (1H,d, J=7.7Hz), 7.55
-7.36 (2H, m), 7.44 (2H, d, J=8.8Hz), 7.00 (3H, b
r.d, J=8.9Hz), 5.47 (2H, s), 2.37 (2H, q, J=7.6H
z), 1.24 (3H, t, J=7.5Hz).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.03 (1H, d, J = 7.7Hz), 7.90 (1H, d, J = 7.7Hz), 7.55
-7.36 (2H, m), 7.44 (2H, d, J = 8.8Hz), 7.00 (3H, b
rd, J = 8.9Hz), 5.47 (2H, s), 2.37 (2H, q, J = 7.6H
z), 1.24 (3H, t, J = 7.5Hz).

【０２３５】[0235]

【実施例３】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］クロロアセトアミド（化合物番号Ａ１．４５）（１）Ｏ−（ベンゾチアゾール−２−イルメチル）−
４−ニトロフェノール（工程Ａ−１）４−ニトロフェノール２．８３ｇをＤＭＦ３０ｍｌに溶
解後、氷水浴中、６０％水素化ナトリウム８５５．５ｍ
ｇを加えた。同温で５分間撹拌した後、２−ブロモメチ
ルベンゾチアゾール４．８８ｇの２５ｍｌＤＭＦ溶液を
加えた。室温に昇温後、４時間撹拌した後、氷水浴中冷
却し、反応液に水１００ｍｌを加えた。析出した結晶を
水洗後、更にヘキサンで洗浄した。得られた粗結晶をシ
リカゲルカラムクロマトグラフィー（溶出溶媒ヘキサ
ン：酢酸エチル＝１０：１）で精製し、融点１８９〜１
９１℃を有する標記化合物４．９９ｇ（８６％）を得
た。Example 3 N- [4- (benzothiazol-2-ylmethoxy) phenyl
Enyl] chloroacetamide (Compound No. A1.45) (1) O- (benzothiazol-2-ylmethyl)-
4-Nitrophenol (Step A-1) After dissolving 2.83 g of 4-nitrophenol in 30 ml of DMF, 855.5 m of 60% sodium hydride was placed in an ice water bath.
g was added. After stirring at the same temperature for 5 minutes, a solution of 4.88 g of 2-bromomethylbenzothiazole in 25 ml of DMF was added. After heating to room temperature and stirring for 4 hours, the mixture was cooled in an ice water bath, and 100 ml of water was added to the reaction solution. The precipitated crystals were washed with water and further washed with hexane. The obtained crude crystals were purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 10: 1) to give a melting point of 189-1.
4.99 g (86%) of the title compound having a temperature of 91 ° C. were obtained.

【０２３６】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.24 (2H, br.d, J=9.3Hz), 8.06 (1H, d, J=7.7Hz),
7.92 (1H, d, J=7.3Hz), 7.58-7.40 (2H, m), 7.14 (2
H, br.d, J=9.3Hz), 5.59 (2H, s). （２）４−（ベンゾチアゾール−２−イルメトキシ）
アニリン（工程Ｂ−３）上記（１）の方法で製造されたＯ−（ベンゾチアゾール
−２−イルメチル）−４−ニトロフェノール４．９９ｇ
をエチルアルコール１００ｍｌに懸濁させ、氷水浴中、
濃塩酸１５ｍｌを静かに加えた後、同温で塩化第一スズ
８．２６ｇを少量ずつ加えた。室温に昇温し３０分撹拌
した後、更に５０℃にて１．５時間撹拌した後、再び濃
塩酸１５ｍｌと塩化第一スズ８．２６ｇを加え５０℃で
４時間撹拌した。室温まで放冷し、反応液に水酸化ナト
リウム水溶液をｐＨ１０になるまで加え、酢酸エチルで
抽出した。抽出液を水洗した後、硫酸ナトリウムで乾燥
した。ろ過後、溶媒を減圧下留去し、得られた粗結晶を
ヘキサン：酢酸エチル（１０：１）の混合溶媒で洗浄
し、融点８７〜９０℃を有する標記化合物１．９２ｇ
（収率４３％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.24 (2H, br.d, J = 9.3Hz), 8.06 (1H, d, J = 7.7Hz),
7.92 (1H, d, J = 7.3Hz), 7.58-7.40 (2H, m), 7.14 (2
H, br.d, J = 9.3 Hz), 5.59 (2H, s). (2) 4- (benzothiazol-2-ylmethoxy)
Aniline (Step B-3) 4.99 g of O- (benzothiazol-2-ylmethyl) -4-nitrophenol produced by the method of (1) above.
Is suspended in 100 ml of ethyl alcohol, and in an ice water bath,
After gently adding 15 ml of concentrated hydrochloric acid, 8.26 g of stannous chloride was added little by little at the same temperature. After raising the temperature to room temperature and stirring for 30 minutes, the mixture was further stirred at 50 ° C. for 1.5 hours, and then 15 ml of concentrated hydrochloric acid and 8.26 g of stannous chloride were added again, followed by stirring at 50 ° C. for 4 hours. After cooling to room temperature, an aqueous sodium hydroxide solution was added to the reaction solution until the pH reached 10, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the obtained crude crystals were washed with a mixed solvent of hexane: ethyl acetate (10: 1) to give 1.92 g of the title compound having a melting point of 87 to 90 ° C.
(43% yield).

【０２３７】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.02 (1H, d, J=7.9Hz), 7.90 (1H,d, J=7.6Hz), 7.53
-7.35 (2H, m), 6.88 (2H, br.d, J=8.8Hz), 6.65 (2H,
br.d, J=8.8Hz), 5.41 (2H, s), 3.65-3.20 (2H, br.
s). （３）Ｎ−［４−（ベンゾチアゾール−２−イルメト
キシ）フェニル］クロロアセトアミド（化合物番号Ａ
１．４５）（工程Ｂ−４）上記（２）の方法で製造された４−（ベンゾチアゾール
−２−イルメトキシ）アニリン３００ｍｇを塩化メチレ
ン６ｍｌに溶解後、氷水浴中、トリエチルアミン０．２
４ｍｌ、クロロアセチルクロリド０．１７ｍｌを加え、
１時間撹拌した。反応液中に飽和塩化アンモニウム水溶
液を加え、塩化メチレンで抽出した。水洗後、硫酸ナト
リウムで乾燥し、ろ過後、溶媒を減圧下留去し、塩化メ
チレンとヘキサンの混合溶剤より再結晶し、融点１９６
〜１９７℃を有する標記化合物２５９．４ｍｇ（６５．
５％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.02 (1H, d, J = 7.9Hz), 7.90 (1H, d, J = 7.6Hz), 7.53
-7.35 (2H, m), 6.88 (2H, br.d, J = 8.8Hz), 6.65 (2H, m
br.d, J = 8.8Hz), 5.41 (2H, s), 3.65-3.20 (2H, br.
s). (3) N- [4- (benzothiazol-2-ylmethoate)
Xy) phenyl] chloroacetamide (Compound No. A
1.45) (Step B-4) After dissolving 300 mg of 4- (benzothiazol-2-ylmethoxy) aniline prepared by the method of the above (2) in 6 ml of methylene chloride, triethylamine 0.2 was dissolved in an ice water bath.
4 ml and chloroacetyl chloride 0.17 ml were added,
Stir for 1 hour. A saturated aqueous solution of ammonium chloride was added to the reaction solution, and extracted with methylene chloride. After washing with water, drying over sodium sulfate and filtration, the solvent was distilled off under reduced pressure, and the residue was recrystallized from a mixed solvent of methylene chloride and hexane.
259.4 mg (65.
5%).

【０２３８】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.17-8.10 (1H, br.s), 8.06 (1H, m), 7.94-7.90 (1
H, m), 7.59-7.44 (4H, m), 7.07-7.03 (2H, m), 5.55
(2H, s), 4.19 (2H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.17-8.10 (1H, br.s), 8.06 (1H, m), 7.94-7.90 (1
H, m), 7.59-7.44 (4H, m), 7.07-7.03 (2H, m), 5.55
(2H, s), 4.19 (2H, s).

【０２３９】[0239]

【実施例４】Ｎ−［（４−ベンゾチアゾール−２−イルメトキシ）−
２−フルオロフェニル］アセトアミド（化合物番号Ｃ
９．１）（１）メチル３−フルオロフェニルカーボネート
（工程Ｂ−１）水酸化ナトリウム２．００ｇを１８ｍｌの水に溶解した
後、３−フルオロフェノール４．００ｇを加え、氷水浴
中３．７ｍｌのクロロ炭酸メチル加え、２０分間撹袢し
た後、室温に昇温し更に２時間撹拌した。その後、酢酸
エチルを加え、有機層を水、塩化ナトリウム水溶液で洗
浄後、硫酸マグネシウムで乾燥させた。ろ過後、溶媒を
留去し、標記化合物の粗結晶を５．８５ｇ得た。Example 4 N-[(4-benzothiazol-2-ylmethoxy)-
2-Fluorophenyl] acetamide (Compound No. C
9.1) (1) Methyl 3-fluorophenyl carbonate (Step B-1) After dissolving 2.00 g of sodium hydroxide in 18 ml of water, 4.00 g of 3-fluorophenol was added, and 3.7 ml of an ice-water bath was added. After stirring for 20 minutes, the mixture was heated to room temperature and further stirred for 2 hours. Thereafter, ethyl acetate was added, and the organic layer was washed with water and an aqueous sodium chloride solution, and then dried over magnesium sulfate. After filtration, the solvent was distilled off to obtain 5.85 g of crude crystals of the title compound.

【０２４０】（２）メチル３−フルオロ−４−ニト
ロフェニルカーボネート（工程Ｂ−２）上記（１）の方法で製造された粗結晶５．８５ｇに氷水
浴中３．６ｍｌの濃硫酸を加え撹拌した後、３．０ｍｌ
の濃硝酸と３．０ｍｌの濃硫酸の混酸をを静かに滴下し
た。１時間撹拌後、反応液を氷水中に静かに加え、生成
した結晶をろ過し、水洗後、減圧下乾燥し、標記化合物
を含む粗結晶７．５８を得た。(2) Methyl 3-fluoro-4-nitto
Lophenyl carbonate (Step B-2) To 5.85 g of the crude crystals produced by the method of the above (1), 3.6 ml of concentrated sulfuric acid was added in an ice water bath and stirred, and then 3.0 ml.
A mixed acid of concentrated nitric acid and 3.0 ml of concentrated sulfuric acid was gently added dropwise. After stirring for 1 hour, the reaction solution was gently added to ice water, the generated crystals were filtered, washed with water, and dried under reduced pressure to obtain crude crystals containing the title compound 7.58.

【０２４１】（３）３−フルオロ−４−ニトロフェノ
ール上記（２）の方法で製造された粗結晶７．５８ｇを１２
０ｍｌのメチルアルコールに溶解した後、氷水浴中３Ｎ
−水酸化ナトリウム水溶液３６ｍｌを加えた。室温に昇
温後、１．５時間撹拌した。その後、反応液中に濃塩酸
をｐＨ１になるまで加えた後、溶媒を留去した。酢酸エ
チルを加え水洗後、硫酸マグネシウムで乾燥した。ろ過
後、溶媒を留去し、シリカゲルカラムクロマトグラフィ
ー（溶出溶媒ヘキサン：酢酸エチル＝２０：１、１
０：１、１：１）で精製し、黄色固体の標記化合物１．
２１ｇ（収率２２％）を得た。(3) 3-fluoro-4-nitropheno
The crude crystals 7.58g produced by the method of Lumpur (2) 12
After dissolving in 0 ml of methyl alcohol, 3N
-36 ml of aqueous sodium hydroxide solution were added. After heating to room temperature, the mixture was stirred for 1.5 hours. Thereafter, concentrated hydrochloric acid was added to the reaction solution until the pH reached 1, and the solvent was distilled off. Ethyl acetate was added, washed with water, and dried over magnesium sulfate. After filtration, the solvent was distilled off and the residue was subjected to silica gel column chromatography (elution solvent: hexane: ethyl acetate = 20: 1, 1: 1).
0: 1, 1: 1) to give the title compound 1.
21 g (22% yield) was obtained.

【０２４２】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.07 (1H, t, J=8.9Hz), 7.32 (1H,br.s), 6.75 (2H,
d, J=11.2Hz). （４）Ｎ−（２−フルオロ−４−ヒドロキシフェニ
ル）アセトアミド（工程Ｂ−３，Ｂ−４）上記（３）の方法で製造された３−フルオロ−４−ニト
ロフェノール３００ｍｇを氷酢酸６ｍｌに溶解し、３７
３．３ｍｇの鉄粉を加えた。還流下６時間撹拌した後、
室温にまで放冷し、氷水を加えろ過した後、ろ液に酢酸
エチルを加え、水で洗浄後、硫酸ナトリウムで乾燥させ
た。ろ過後、溶媒を留去し、シリカゲルカラムクロマト
グラフィー（溶出溶媒ヘキサン：酢酸エチル＝２：
１、１：１）で精製し、茶褐色固体の標記化合物２０
６．８ｍｇ（収率６４％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.07 (1H, t, J = 8.9Hz), 7.32 (1H, br.s), 6.75 (2H,
d, J = 11.2Hz). (4) N- (2-fluoro-4-hydroxyphenyl )
A) Acetamide (Steps B-3 and B-4) Dissolve 300 mg of 3-fluoro-4-nitrophenol produced by the method of the above (3) in 6 ml of glacial acetic acid.
3.3 mg of iron powder was added. After stirring for 6 hours under reflux,
After allowing to cool to room temperature, adding ice water and filtering, ethyl acetate was added to the filtrate, washed with water and dried over sodium sulfate. After filtration, the solvent was distilled off and the residue was subjected to silica gel column chromatography (elution solvent: hexane: ethyl acetate = 2:
1, 1: 1) to give the title compound 20 as a brown solid.
6.8 mg (64% yield) were obtained.

【０２４３】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.92 (1H, t, J=8.5Hz), 7.12 (1H,br.s), 6.66-6.52
(2H, m), 5.64 (1H, br.s). （５）Ｎ−［（４−ベンゾチアゾール−２−イルメト
キシ）−２−フルオロフェニル］アセトアミド（化合物
番号Ｃ９．１）（工程Ａ−１）上記（４）の方法で製造されたＮ−（２−フルオロ−４
−ヒドロキシフェニル）アセトアミド２０６．８ｍｇを
５ｍｌのＤＭＦに溶解し、氷水浴中６０％水素化ナト
リウム５３．８ｍｇを加え５分間撹袢した後、２−ブロ
モメチルベンゾチアゾール３０５．７ｍｇを加えた。室
温に昇温後、更に２．５時間撹拌した。飽和塩化アンモ
ニウム水溶液を加え、酢酸エチルで抽出後、飽和食塩水
で洗浄後、無水硫酸ナトリウムで乾燥した。ろ過後、溶
媒を留去し、塩化メチレンとヘキサンの混合溶剤より再
結晶し、融点１６７〜１６９℃を有する標記化合物２８
７．２ｍｇ（収率７４．４％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.92 (1H, t, J = 8.5Hz), 7.12 (1H, br.s), 6.66-6.52
(2H, m), 5.64 (1H, br.s). (5) N-[(4-benzothiazol-2-ylmethoate)
Xy) -2-fluorophenyl] acetamide (compound
No. C9.1) (Step A-1) N- (2-fluoro-4) produced by the method of the above (4)
206.8 mg of -hydroxyphenyl) acetamide was dissolved in 5 ml of DMF, 53.8 mg of 60% sodium hydride was added in an ice water bath, and the mixture was stirred for 5 minutes, and 305.7 mg of 2-bromomethylbenzothiazole was added. After the temperature was raised to room temperature, the mixture was further stirred for 2.5 hours. A saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate, washed with saturated saline, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off and recrystallized from a mixed solvent of methylene chloride and hexane to give the title compound 28 having a melting point of 167 to 169 ° C.
7.2 mg (74.4% yield) were obtained.

【０２４４】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.19-7.88 (3H, m), 7.51-7.41 (2H,m), 7.15 (1H, b
r.s), 6.86-6.80 (2H,m), 5.46 (2H, s), 2.19 (3H,
s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.19-7.88 (3H, m), 7.51-7.41 (2H, m), 7.15 (1H, b
rs), 6.86-6.80 (2H, m), 5.46 (2H, s), 2.19 (3H,
s).

【０２４５】[0245]

【実施例５】Ｎ−［４−（６−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］アセトアミド（化合物番号Ｆ４．
３０) （１）メチル（６−フルオロベンゾチアゾール−２
−イル）ホーメート（工程Ｄ−１）２−シアノ−６−フルオロベンゾチアゾール１３７．２
ｍｇにメチルアルコール２．７ｍｌを加え撹拌しなが
ら、氷水浴中、塩化水素ガスを３分間導入した。２分間
撹拌した後、水を加え、酢酸エチルで抽出した。抽出液
を、水、塩化ナトリウム水溶液で洗浄後、硫酸ナトリウ
ムで乾燥した。ろ過後、溶媒を留去し、シリカゲルカラ
ムクロマトグラフィー（溶出溶媒ヘキサン：酢酸エチ
ル＝５：１）で精製し、薄黄色結晶の標記化合物１０
６．８ｍｇ（収率６８％）を得た。Example 5 N- [4- (6-fluorobenzothiazol-2-yl)
Methoxy) phenyl] acetamide (Compound No. F4.
30) (1) Methyl (6-fluorobenzothiazole-2)
-Yl) formate (Step D-1) 2-cyano-6-fluorobenzothiazole 137.2
2.7 ml of methyl alcohol was added to the mg, and while stirring, hydrogen chloride gas was introduced for 3 minutes in an ice water bath. After stirring for 2 minutes, water was added and extracted with ethyl acetate. The extract was washed with water and an aqueous sodium chloride solution, and then dried over sodium sulfate. After filtration, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 5: 1) to give the title compound 10 as pale yellow crystals.
6.8 mg (68% yield) were obtained.

【０２４６】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.21 (1H, dd, J=9.1, 4.9Hz), 7.66(1H, dd, J=8.1,
2.5Hz), 7.34 (1H, td, J=8.9Hz, 2.6Hz), 4.09 (3H,
s). （２）２−ヒドロキシメチル−６−フルオロベンゾチ
アゾール（工程Ｄ−２）上記（１）の方法で製造されたメチル（６−フルオロ
ベンゾチアゾール−２−イル）ホーメート１０６．１ｍ
ｇをメチルアルコール２．１ｍｌに溶解し、氷水浴中、
水素化ホウ素リチウム１６．５ｍｇを加え、１０分間撹
拌した後、更に水素化ホウ素リチウム１０ｍｇを加え、
１０分間撹拌した。反応液中に水を加え、酢酸エチルで
抽出した。抽出液を、水、塩化ナトリウム水溶液で洗浄
後、硫酸ナトリウムで乾燥した。ろ過後、溶媒を留去
し、白色粗結晶の標記化合物９３．１ｍｇを得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.21 (1H, dd, J = 9.1, 4.9Hz), 7.66 (1H, dd, J = 8.1,
2.5Hz), 7.34 (1H, td, J = 8.9Hz, 2.6Hz), 4.09 (3H,
s). (2) 2-hydroxymethyl-6-fluorobenzothi
Azole (Step D-2) Methyl (6-fluorobenzothiazol-2-yl) formate 106.1 m produced by the method of the above (1)
g in 2.1 ml of methyl alcohol and placed in an ice water bath.
After adding 16.5 mg of lithium borohydride and stirring for 10 minutes, further adding 10 mg of lithium borohydride,
Stir for 10 minutes. Water was added to the reaction solution, and extracted with ethyl acetate. The extract was washed with water and an aqueous sodium chloride solution, and then dried over sodium sulfate. After filtration, the solvent was distilled off to obtain 93.1 mg of the title compound as white crude crystals.

【０２４７】（３）６−フルオロ−２−メタンスルホ
ニルオキシメチルベンゾチアゾール（工程Ｄ−６）上記（２）の方法で製造された２−ヒドロキシメチル−
６−フルオロベンゾチアゾール９３．１ｍｇを塩化メチ
レン１．８ｍｌに溶解し、氷水浴中、０．０８ｍｌのト
リエチルアミンと０．０５ｍｌのメタンスルホニルクロ
リドを加えた後、室温に昇温し１時間撹拌した。反応液
中に水を加え、塩化メチレンで抽出した後、水、塩化ナ
トリウム水溶液で洗浄後、硫酸ナトリウムで乾燥した。
ろ過後、溶媒を留去し、シリカゲルカラムクロマトグラ
フィー（溶出溶媒ヘキサン：酢酸エチル＝１：１）で
精製し、融点６８〜７２℃を有する標記化合物１２５．
３ｍｇ（収率９４％）を得た。(3) 6-fluoro-2-methanesulfo
Nyloxymethylbenzothiazole (Step D-6) 2-hydroxymethyl- produced by the method of (2) above
93.1 mg of 6-fluorobenzothiazole was dissolved in 1.8 ml of methylene chloride, and 0.08 ml of triethylamine and 0.05 ml of methanesulfonyl chloride were added in an ice-water bath, followed by heating to room temperature and stirring for 1 hour. Water was added to the reaction solution, extracted with methylene chloride, washed with water and an aqueous sodium chloride solution, and dried over sodium sulfate.
After filtration, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 1) to give the title compound having a melting point of 68 to 72 ° C.
3 mg (94% yield) were obtained.

【０２４８】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.01 (1H, dd, J=8.9, 4.8Hz), 7.61(1H, dd, J=8.1,
2.5Hz), 7.23 (1H, td, J=8.9Hz, 2.5Hz), 5.58 (2H,
s), 3.15 (3H, s). （４）Ｎ−［４−（６−フルオロベンゾチアゾール−
２−イルメトキシ）フェニル］アセトアミド（化合物番
号Ｆ４．３０）（工程Ａ−１）４−アセトアミドフェノール６４．６ｍｇをＤＭＦ１．
３ｍｌに溶解し、氷水浴中、６０％水素化ナトリウム１
８．８ｍｇを加え、３分間撹拌した後、上記（３）の方
法で製造された６−フルオロ−２−メタンスルホニルオ
キシメチルベンゾチアゾール１２２．８ｍｇをＤＭＦ
０．４ｍｌに溶解した溶液を加えた。室温に昇温し３時
間撹拌した後、飽和塩化アンモニウム水溶液を加え、酢
酸エチルで抽出した。抽出液を、水、塩化ナトリウム水
溶液で洗浄後、硫酸ナトリウムで乾燥した。ろ過後、溶
媒を留去し、シリカゲルカラムクロマトグラフィー（溶
出溶媒ヘキサン：酢酸エチル＝１：２）で精製し、融
点２０４〜２０５℃を有する標記化合物３８．３ｍｇ
（収率２８％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.01 (1H, dd, J = 8.9, 4.8Hz), 7.61 (1H, dd, J = 8.1,
2.5Hz), 7.23 (1H, td, J = 8.9Hz, 2.5Hz), 5.58 (2H,
s), 3.15 (3H, s). (4) N- [4- (6-fluorobenzothiazole-
2-ylmethoxy) phenyl] acetamide (Compound No.
No. F4.30) (Step A-1) 64.6 mg of 4-acetamidophenol was added to DMF1.
Dissolve in 3 ml and place in 60% sodium hydride 1 in an ice water bath.
After adding 8.8 mg and stirring for 3 minutes, 122.8 mg of 6-fluoro-2-methanesulfonyloxymethylbenzothiazole produced by the method of the above (3) was added to DMF.
A solution dissolved in 0.4 ml was added. After warming to room temperature and stirring for 3 hours, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and an aqueous sodium chloride solution, and then dried over sodium sulfate. After filtration, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 2), and 38.3 mg of the title compound having a melting point of 204 to 205 ° C.
(Yield 28%) was obtained.

【０２４９】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.97 (1H, dd, J=8.8, 4.8Hz), 7.57(1H, dd, J=8.0,
2.5Hz), 7.43 (2H, d, J=8.8Hz), 7.31-7.18 (1H, m),
7.08(1H, br.s), 7.00 (2H, d, J=9.0Hz), 5.44 (2H,
s), 2.16 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.97 (1H, dd, J = 8.8, 4.8Hz), 7.57 (1H, dd, J = 8.0,
2.5Hz), 7.43 (2H, d, J = 8.8Hz), 7.31-7.18 (1H, m),
7.08 (1H, br.s), 7.00 (2H, d, J = 9.0Hz), 5.44 (2H,
s), 2.16 (3H, s).

【０２５０】[0250]

【実施例６】Ｎ−［４−（６−メトキシベンゾチアゾール−２−イル
メトキシ）フェニル］アセトアミド（化合物番号Ｆ３．
２０）（１）２−ブロモメチル−６−メトキシベンゾチアゾ
ール（工程Ｃ−１）２−メチル−６−メトキシベンゾチアゾール０．８ｍｌ
を四塩化炭素２０ｍｌに溶解し、Ｎ−ブロモスクシンイ
ミド１．０５ｇとジベンゾイルパーオキサイド（ＢＰ
Ｏ）１７．４ｍｇを加え、還流下５時間撹拌した。室温
に放冷後、塩化メチレンで抽出した。抽出液を、飽和亜
硫酸ナトリウム水溶液、水、塩化ナトリウム水溶液で洗
浄後、硫酸ナトリウムで乾燥した。ろ過後、溶媒を留去
し、シリカゲルカラムクロマトグラフィー（溶出溶媒
ヘキサン：酢酸エチル＝８：１）で精製し、融点７８〜
８１℃を有する標記化合物６４９．３ｍｇ（収率４７
％）を得た。Example 6 N- [4- (6-methoxybenzothiazol-2-yl)
Methoxy) phenyl] acetamide (Compound No. F3.
20) (1) 2-bromomethyl-6-methoxybenzothiazo
Lumpur (Step C-1) 2-methyl-6-methoxy-benzothiazole 0.8ml
Was dissolved in 20 ml of carbon tetrachloride, and 1.05 g of N-bromosuccinimide and dibenzoyl peroxide (BP
O) 17.4 mg was added, and the mixture was stirred under reflux for 5 hours. After cooling to room temperature, the mixture was extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium sulfite, water and an aqueous solution of sodium chloride, and then dried over sodium sulfate. After filtration, the solvent is distilled off, and silica gel column chromatography (elution solvent
Hexane: ethyl acetate = 8: 1) to give a melting point of 78-
649.3 mg of the title compound having a temperature of 81 ° C (yield 47).
%).

【０２５１】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.91 (1H, d, J=9.0Hz), 7.32 (1H,d, J=2.5Hz), 7.10
(1H, dd, J=9.0, 2.5Hz), 4.80 (2H, s), 3.89 (3H,
s). （２）Ｎ−［４−（６−メトキシベンゾチアゾール−
２−イルメトキシ）フェニル］アセトアミド（化合物番
号Ｆ３．２０）（工程Ａ−１）４−アセトアミドフェノール１９７．８ｍｇをＤＭＦ４
ｍｌに溶解し、氷水浴中、６０％水素化ナトリウム５
７．６ｍｇを加え、５分間撹拌した後、上記（１）の方
法で製造された２−ブロモメチル−６−メトキシベンゾ
チアゾール３７１．５ｍｇをＤＭＦ１ｍｌに溶解した溶
液を加えた。室温に昇温し２時間撹拌した後、飽和塩化
アンモニウム水溶液を加え、酢酸エチルで抽出した。抽
出液を、水、塩化ナトリウム水溶液で洗浄後、硫酸ナト
リウムで乾燥した。ろ過後、溶媒を留去し、シリカゲル
カラムクロマトグラフィー（溶出溶媒ヘキサン：酢酸
エチル＝１：２）で精製し、融点１４５〜１４７℃を有
する標記化合物３９９．１ｍｇ（収率９３％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.91 (1H, d, J = 9.0Hz), 7.32 (1H, d, J = 2.5Hz), 7.10
(1H, dd, J = 9.0, 2.5Hz), 4.80 (2H, s), 3.89 (3H,
s). (2) N- [4- (6-methoxybenzothiazole-
2-ylmethoxy) phenyl] acetamide (Compound No.
No. F3.20) (Step A-1) 197.8 mg of 4-acetamidophenol was added to DMF4.
and 60% sodium hydride 5 in an ice-water bath.
After adding 7.6 mg and stirring for 5 minutes, a solution of 371.5 mg of 2-bromomethyl-6-methoxybenzothiazole prepared in the above method (1) dissolved in 1 ml of DMF was added. After warming to room temperature and stirring for 2 hours, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and an aqueous sodium chloride solution, and then dried over sodium sulfate. After filtration, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 2) to obtain 399.1 mg (yield: 93%) of the title compound having a melting point of 145 to 147 ° C. .

【０２５２】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.90 (1H, d, J=9.0Hz), 7.41 (2H,d, J=9.1Hz), 7.33
(1H, d, J=2.5Hz),7.16 (1H, br.s), 7.11 (1H, dd, J
=8.9,2.5Hz), 6.77 (2H, d, J=9.1Hz), 5.41 (2H, s),
3.88 (3H, s), 2.15 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.90 (1H, d, J = 9.0Hz), 7.41 (2H, d, J = 9.1Hz), 7.33
(1H, d, J = 2.5Hz), 7.16 (1H, br.s), 7.11 (1H, dd, J
= 8.9,2.5Hz), 6.77 (2H, d, J = 9.1Hz), 5.41 (2H, s),
3.88 (3H, s), 2.15 (3H, s).

【０２５３】[0253]

【実施例７】Ｎ−｛４−［１−（ベンゾチアゾール−２−イル）エト
キシ］フェニル｝アセトアミド（化合物番号Ｅ１．１）（１）２−ホルミルベンゾチアゾール（工程Ｄ−３）２−ヒドロキシメチルベンゾチアゾール２．２６ｇをア
セトン２０ｍｌに溶解し、室温下、二酸化マンガン５．
４７ｇを加えた。還流下５時間撹袢した後、室温にまで
放冷し、１４時間放置した。更に二酸化マンガン３．０
６ｇを加え、還流下６時間撹袢した後、室温にまで放冷
しろ過した。ろ液を濃縮後、得られた粗結晶に石油エー
テルを加え、更にろ過し、ろ液を約半分に濃縮した時点
で析出した結晶をろ取し、融点６９〜７０℃を有する標
記化合物４３２．６ｍｇ（収率１９．３％）を得た。Example 7 N- {4- [1- (benzothiazol-2-yl) ethoate
[Xy] phenyl} acetamide (Compound No. E1.1) (1) 2- Formylbenzothiazole (Step D-3) 2.26 g of 2-hydroxymethylbenzothiazole is dissolved in 20 ml of acetone, and manganese dioxide is added at room temperature.
47 g were added. After stirring for 5 hours under reflux, the mixture was allowed to cool to room temperature and left for 14 hours. Further, manganese dioxide 3.0
After adding 6 g and stirring under reflux for 6 hours, the mixture was allowed to cool to room temperature and filtered. After the filtrate was concentrated, petroleum ether was added to the obtained crude crystals, which was further filtered. When the filtrate was concentrated to about half, the precipitated crystals were collected by filtration to give the title compound 432. having a melting point of 69 to 70 ° C. 6 mg (19.3% yield) was obtained.

【０２５４】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
10.18 (1H, s), 8.28-8.23 (1H, m),8.05-8.00 (1H,
m), 7.68-7.54 (2H, m). （２）２−（１−ヒドロキシエチル）ベンゾチアゾー
ル（工程Ｄ−４）上記（１）の方法で製造された２−ホルミルベンゾチア
ゾール０．６１ｇをテトラヒドロフラン（ＴＨＦ）１２
ｍｌに溶解し、アセトン−ドライアイス浴中、メチルマ
グネシウムブロミド５．０ｍｌを滴下した。反応容器を
氷水浴中に移し、３．５時間撹拌した。反応液中に飽和
塩化アンモニウム水溶液を加え、酢酸エチルで抽出し
た。抽出液を、塩化ナトリウム水溶液で洗浄後、硫酸ナ
トリウムで乾燥した。ろ過後、溶媒を留去し、シリカゲ
ルカラムクロマトグラフィー（溶出溶媒ヘキサン：酢
酸エチル＝４：１）で精製し、融点５９〜６０℃を有す
る標記化合物０．４４ｇ（収率６６％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
10.18 (1H, s), 8.28-8.23 (1H, m), 8.05-8.00 (1H,
m), 7.68-7.54 (2H, m). (2) 2- (1-hydroxyethyl) benzothiazole
Le (Step D-4) above (1) was prepared by the process 2-formyl-benzothiazole 0.61g of tetrahydrofuran (THF) 12
Then, 5.0 ml of methylmagnesium bromide was added dropwise in an acetone-dry ice bath. The reaction vessel was transferred into an ice-water bath and stirred for 3.5 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over sodium sulfate. After filtration, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 4: 1) to obtain 0.44 g (66% yield) of the title compound having a melting point of 59 to 60 ° C. .

【０２５５】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.97 (1H, d, J=8.3Hz), 7.87 (1H,dd, J=8.2, 1.3H
z), 7.47 (1H, td, J=7.7Hz, 1.5Hz), 7.37 (1H, td, J
t=7.5Hz, Jd=1.4Hz), 5.26 (1H, qd, J=14.1Hz, 4.8H
z), 3.7-3.5 (1H, br.s), 1.71 (1H, d, J=6.6Hz). （３）２−( １−メタンスルホニルオキシエチル) ベ
ンゾチアゾール（工程Ｄ−６）上記（２）の方法で製造された２−（１−ヒドロキシエ
チル）−ベンゾチアゾール３８４．４ｍｇを４ｍｌの塩
化メチレンに溶解し、氷水浴中０．３３ｍｌのトリエチ
ルアミンを加え、更に０．１８ｍｌのメタンスルホニル
クロリドを加えた。室温に昇温後、２時間撹袢した。食
塩水を加えた後、塩化メチレンで抽出し、水洗後、無水
硫酸ナトリウムで乾燥した。ろ過後、溶媒を留去し、オ
イル状の標記化合物５１９．４ｍｇ（収率９４．３％）
を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.97 (1H, d, J = 8.3Hz), 7.87 (1H, dd, J = 8.2, 1.3H
z), 7.47 (1H, td, J = 7.7Hz, 1.5Hz), 7.37 (1H, td, J
t = 7.5Hz, Jd = 1.4Hz), 5.26 (1H, qd, J = 14.1Hz, 4.8H
z), 3.7-3.5 (1H, br.s), 1.71 (1H, d, J = 6.6Hz). (3) 2- (1-methanesulfonyloxyethyl)
Nzothiazole (Step D-6) Dissolve 384.4 mg of 2- (1-hydroxyethyl) -benzothiazole prepared by the method of (2) in 4 ml of methylene chloride and add 0.33 ml of triethylamine in an ice water bath. And an additional 0.18 ml of methanesulfonyl chloride. After the temperature was raised to room temperature, the mixture was stirred for 2 hours. After adding saline, the mixture was extracted with methylene chloride, washed with water, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the oily title compound (519.4 mg, yield 94.3%) was obtained.
I got

【０２５６】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.05 (1H, dd, J=7.5, 1.3Hz), 7.92(1H, dd, J=7.7,
2.0Hz), 7.51 (1H, td, J=7.2Hz, 1.4Hz), 7.44 (1H, t
d, J=7.7Hz, 1.5Hz), 6.10 (1H, q, J=6.6Hz), 3.07 (3
H, s), 1.93 (3H, d, J=6.6Hz). （４）Ｎ−｛４−［１−（ベンゾチアゾール−２−イ
ル）エトキシ］フェニル｝アセトアミド（化合物番号Ｅ
１．１）（工程Ａ−１）上記（３）の方法で製造された２−（１−メタンスルホ
ニルオキシエチル）−ベンゾチアゾール１４３．３ｍｇ
と４−アセトアミドフェノール８４ｍｇを２．３ｍｌの
ＤＭＦに溶解し、氷水浴中２２ｍｇの６０％水素化ナト
リウムを加え、室温に昇温後、２．５時間撹袢した。水
を加えた後、酢酸エチルで抽出し、飽和食塩水で洗浄
後、無水硫酸ナトリウムで乾燥させた。ろ過後、溶媒を
留去し、分取用薄層クロマトグラフィーで分取し、オイ
ル状の標記化合物７０．４ｍｇ（収率４０．５％）を得
た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.05 (1H, dd, J = 7.5, 1.3Hz), 7.92 (1H, dd, J = 7.7,
2.0Hz), 7.51 (1H, td, J = 7.2Hz, 1.4Hz), 7.44 (1H, t
d, J = 7.7Hz, 1.5Hz), 6.10 (1H, q, J = 6.6Hz), 3.07 (3
H, s), 1.93 (3H, d, J = 6.6 Hz). (4) N- {4- [1- (benzothiazol-2-i)
Ru) ethoxy] phenyl} acetamide (Compound No. E
1.1) (Step A-1) 143.3 mg of 2- (1-methanesulfonyloxyethyl) -benzothiazole produced by the method of (3) above.
And 84 mg of 4-acetamidophenol were dissolved in 2.3 ml of DMF, 22 mg of 60% sodium hydride was added in an ice water bath, and the mixture was heated to room temperature and stirred for 2.5 hours. After adding water, the mixture was extracted with ethyl acetate, washed with saturated saline, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the residue was separated by preparative thin-layer chromatography to obtain 70.4 mg (yield: 40.5%) of the title compound as an oil.

【０２５７】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.01 (1H, d, J=7.3Hz), 7.86 (1H,dd, J=7.2, 1.3H
z), 7.49 (1H, td, J=7.6Hz, 1.4Hz), 7.42-7.34 (1H,
m), 7.35 (2H, d, J=9.0Hz), 7.05 (1H, br.s), 6.96
(2H, d, J=9.0Hz), 5.70 (1H, q,J=6.5Hz), 2.13 (3H,
s), 1.83 (3H, d, J=6.5Hz).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.01 (1H, d, J = 7.3Hz), 7.86 (1H, dd, J = 7.2, 1.3H
z), 7.49 (1H, td, J = 7.6Hz, 1.4Hz), 7.42-7.34 (1H,
m), 7.35 (2H, d, J = 9.0Hz), 7.05 (1H, br.s), 6.96
(2H, d, J = 9.0Hz), 5.70 (1H, q, J = 6.5Hz), 2.13 (3H,
s), 1.83 (3H, d, J = 6.5Hz).

【０２５８】[0258]

【実施例８】Ｎ−｛４−［１−メチル−１−（ベンゾチアゾール−２
−イル）エトキシ］フェニル｝アセトアミド（化合物番
号Ｅ４．１）（１）２−（１−メチル−１−ヒドロキシエチル）ベ
ンゾチアゾール（工程Ｄ−５）エチル（ベンゾチアゾール−２−イル）カルボキシレ
ート３０４．４ｍｇをジエチルエーテル６．１ｍｌに溶
解し、アセトン−ドライアイス浴中、３Ｍ−メチルマグ
ネシウムブロミド／ＴＨＦ溶液５．０ｍｌを滴下した。
同温度下、３０分間撹拌した後、室温にまで昇温し、２
時間撹拌した。反応液中に１Ｎ−塩酸を加え、ジエチル
エーテルで抽出した。抽出液を、水、塩化ナトリウム水
溶液で洗浄後、硫酸ナトリウムで乾燥した。ろ過後、溶
媒を留去し、シリカゲルカラムクロマトグラフィー（溶
出溶媒ヘキサン：酢酸エチル＝６：１）で精製し、白
色結晶状の標記化合物１９７．１ｍｇ（収率７０％）を
得た。Example 8 N- {4- [1-methyl-1- (benzothiazole-2)
-Yl) ethoxy] phenyl} acetamide (compound number
No. E4.1) (1) 2- (1-methyl-1-hydroxyethyl) be
Nzothiazole (Step D-5) 304.4 mg of ethyl (benzothiazol-2-yl) carboxylate is dissolved in 6.1 ml of diethyl ether, and 5.0 ml of a 3M-methylmagnesium bromide / THF solution is placed in an acetone-dry ice bath. It was dropped.
After stirring at the same temperature for 30 minutes, the temperature is raised to room temperature,
Stirred for hours. 1N-hydrochloric acid was added to the reaction solution, and extracted with diethyl ether. The extract was washed with water and an aqueous sodium chloride solution, and then dried over sodium sulfate. After filtration, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 6: 1) to obtain 197.1 mg (yield: 70%) of the title compound as white crystals.

【０２５９】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.99 (1H, br.d, J=8.8Hz), 7.89 (1H, br.d, J=7.7H
z), 7.52-7.30 (2H, m), 3.06 (1H, s), 1.76 (6H, s). （２）Ｏ−［１−メチル−１−（ベンゾチアゾール−
２−イル）エチル］−４−ニトロフェノール（工程Ｄ−
７）上記（１）の方法で製造された２−（１−メチル−１−
ヒドロキシエチル）ベンゾチアゾール１５６．６ｍｇを
３．１ｍｌのＤＭＦに溶解し、カリウムｔ−ブトキシド
１０８．９ｍｇと４−クロロニトロベンゼン１３４．１
ｍｇを加え、３時間撹袢した後、６０℃にて４時間撹袢
した。更に９０℃にて５時間撹袢した後、室温にまで放
冷した。飽和塩化アンモニウム水溶液を加え、酢酸エチ
ルで抽出した。水、食塩水で洗浄後、無水硫酸ナトリウ
ムで乾燥し、ろ過後、溶媒を留去し、シリカゲルカラム
クロマトグラフィー（溶出溶媒ヘキサン：酢酸エチル
＝１０：１）で精製し、オイル状の標記化合物１９７．
１ｍｇ（収率７０％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.99 (1H, br.d, J = 8.8Hz), 7.89 (1H, br.d, J = 7.7H
z), 7.52-7.30 (2H, m), 3.06 (1H, s), 1.76 (6H, s). (2) O- [1-methyl-1- (benzothiazole-
2-yl) ethyl] -4-nitrophenol (Step D-
7) 2- (1-methyl-1-) produced by the method of the above (1)
(Hydroxyethyl) benzothiazole (156.6 mg) was dissolved in 3.1 ml of DMF, and 108.9 mg of potassium t-butoxide and 134.1 of 4-chloronitrobenzene were dissolved.
The mixture was stirred for 3 hours, and then stirred at 60 ° C. for 4 hours. After further stirring at 90 ° C. for 5 hours, the mixture was allowed to cool to room temperature. A saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous sodium sulfate, filtered, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 10: 1) to give the title compound 197 as an oil. .
1 mg (70% yield) was obtained.

【０２６０】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.06 (3H, br.d, J=9.4Hz), 7.87 (1H, d, J=7.4Hz),
7.58-7.38 (2H, m), 6.87 (2H, d, J=9.2Hz), 1.99 (6
H, s). （３）Ｏ−［１−メチル−１−（ベンゾチアゾール−
２−イル）エチル］−４−アミノフェノール（工程Ｂ−
３）上記（２）の方法で製造されたＯ−［１−メチル−１−
（ベンゾチアゾール−２−イル）エチル］−４−ニトロ
フェノール５５．２ｍｇをメチルアルコール１．１ｍｌ
に溶解し、５％パラジウム−炭素触媒下、水素を添加し
た。４．５時間後、反応容器中を窒素ガスで置換した。
ろ過した後、溶媒を留去し、オイル状の粗成生物４５．
３ｍｇを得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.06 (3H, br.d, J = 9.4Hz), 7.87 (1H, d, J = 7.4Hz),
7.58-7.38 (2H, m), 6.87 (2H, d, J = 9.2Hz), 1.99 (6
H, s). (3) O- [1-methyl-1- (benzothiazole-
2-yl) ethyl] -4-aminophenol (Step B-
3) O- [1-methyl-1-) produced by the method of the above (2).
(Benzothiazol-2-yl) ethyl] -4-nitrophenol (55.2 mg) in methyl alcohol (1.1 ml)
And hydrogen was added under a 5% palladium-carbon catalyst. After 4.5 hours, the inside of the reaction vessel was replaced with nitrogen gas.
After filtration, the solvent was distilled off to obtain an oily crude product.
3 mg were obtained.

【０２６１】（４）Ｎ−｛４−［１−メチル−１−
（ベンゾチアゾール−２−イル）エトキシ］フェニル｝
アセトアミド（化合物番号Ｅ４．１）（工程Ａ−１）上記（３）の方法で製造された粗成生物４５．３ｍｇを
塩化メチレン４ｍｌに溶解し、氷水浴中０．０２５ｍｌ
のトリエチルアミンと０．０１３ｍｌの塩化アセチルを
加えた。室温に昇温後、２時間撹袢した。水を加え、塩
化メチレンで抽出し、水、食塩水で洗浄後、無水硫酸ナ
トリウムで乾燥した。ろ過後、溶媒を留去後、シリカゲ
ルカラムクロマトグラフィー（溶出溶媒ヘキサン：酢
酸エチル＝１：２）で精製し、融点１４９〜１５０℃を
有する標記化合物４８．０ｍｇ（収率８４％）を得た。(4) N- {4- [1-methyl-1-
(Benzothiazol-2-yl) ethoxy] phenyl}
Acetamide (Compound No. E4.1) (Step A-1) 45.3 mg of the crude product produced by the method of the above (3) is dissolved in 4 ml of methylene chloride and 0.025 ml in an ice water bath.
Of triethylamine and 0.013 ml of acetyl chloride were added. After the temperature was raised to room temperature, the mixture was stirred for 2 hours. Water was added, extracted with methylene chloride, washed with water and brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 2) to obtain 48.0 mg (yield 84%) of the title compound having a melting point of 149 to 150 ° C. .

【０２６２】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.03 (1H, br.d, J=8.6Hz), 7.90 (1H, br.d, J=7.6H
z), 7.53-7.28 (4H, m), 7.05 (1H, br.s), 6.85 (2H,
d, J=8.9Hz), 2.14 (3H, s), 1.84 (6H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.03 (1H, br.d, J = 8.6Hz), 7.90 (1H, br.d, J = 7.6H)
z), 7.53-7.28 (4H, m), 7.05 (1H, br.s), 6.85 (2H,
d, J = 8.9Hz), 2.14 (3H, s), 1.84 (6H, s).

【０２６３】[0263]

【実施例９】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］ブチルアミド（化合物番号Ｆ４．
１９）（１）Ｏ−（５−フルオロベンゾチアゾール−２−イ
ルメチル）−４−ニトロフェノール（工程Ａ−１）４−ニトロフェノール１．５ｇをＤＭＦ３０ｍｌに溶解
し、氷水浴中、６０％水素化ナトリウム４５２．９ｍｇ
を加え、５分間撹拌した後、２−ブロモメチル−５−フ
ルオロベンゾチアゾール２．７９ｇをＤＭＦ５ｍｌに溶
解した溶液を加えた。室温に昇温し３時間撹拌した後、
飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出
した。抽出液を、水、塩化ナトリウム水溶液で洗浄後、
硫酸ナトリウムで乾燥した。ろ過後、溶媒を留去し、塩
化メチレン−ヘキサン混合溶媒により洗浄し、標記化合
物の粗結晶２．３３ｇを得た。Example 9 N- [4- (5-fluorobenzothiazol-2-yl)
Methoxy) phenyl] butyramide (Compound No. F4.
19) (1) O- (5-fluorobenzothiazol-2-i
( Methyl) -4-nitrophenol (Step A-1) 1.5 g of 4-nitrophenol was dissolved in 30 ml of DMF, and 452.9 mg of 60% sodium hydride was placed in an ice water bath.
After stirring for 5 minutes, a solution obtained by dissolving 2.79 g of 2-bromomethyl-5-fluorobenzothiazole in 5 ml of DMF was added. After warming to room temperature and stirring for 3 hours,
A saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. After washing the extract with water and aqueous sodium chloride solution,
Dried over sodium sulfate. After filtration, the solvent was distilled off, and the residue was washed with a mixed solvent of methylene chloride and hexane to obtain 2.33 g of crude crystals of the title compound.

【０２６４】（２）４−（５−フルオロベンゾチアゾ
ール−２−イルメトキシ）アニリン（工程Ｂ−３）上記（１）の方法で製造されたＯ−（５−フルオロベン
ゾチアゾ−ル−２−イルメチル）−４−ニトロフェノー
ル２．３３ｇにエチルアルコール４７ｍｌを加え撹拌し
ながら、濃塩酸１．５ｍｌを静かに加え、次いで、塩化
第一スズ３．６３ｇを少量ずつ加えた。室温下３０分間
撹拌した後、更に濃塩酸３ｍｌを加え、１．５時間撹拌
した。次いで、５０℃にて４時間撹拌した後、氷水浴中
で冷却し、１０％水酸化ナトリウム水溶液を加え、ｐＨ
１０に調整した。酢酸エチルで抽出し、抽出液を、水、
塩化ナトリウム水溶液で洗浄後、硫酸ナトリウムで乾燥
した。ろ過後、溶媒を留去し、塩化メチレン−ヘキサン
混合溶媒より再結晶し、融点１２５〜１２８℃を有する
標記化合物１．５４ｇ（収率７３％）を得た。(2) 4- (5-fluorobenzothiazo )
2-ylmethoxy) aniline (Step B-3) 2.33 g of O- (5-fluorobenzothiazol-2-ylmethyl) -4-nitrophenol produced by the method of the above (1) was added with ethyl. While adding 47 ml of alcohol and stirring, 1.5 ml of concentrated hydrochloric acid was gently added, and then 3.63 g of stannous chloride was added little by little. After stirring at room temperature for 30 minutes, 3 ml of concentrated hydrochloric acid was further added, and the mixture was stirred for 1.5 hours. Next, after stirring at 50 ° C. for 4 hours, the mixture was cooled in an ice-water bath, and a 10% aqueous sodium hydroxide solution was added thereto.
Adjusted to 10. Extract with ethyl acetate, extract the water,
After washing with an aqueous sodium chloride solution, the extract was dried over sodium sulfate. After filtration, the solvent was distilled off, and the residue was recrystallized from a mixed solvent of methylene chloride and hexane to obtain 1.54 g (yield 73%) of the title compound having a melting point of 125 to 128 ° C.

【０２６５】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.84 (1H, dd, J=9.0, 4.7Hz), 7.72(1H, dd, J=9.5,
2.5Hz), 7.23-7.12 (1H, m), 6.87 (2H, br.d, J=8.8H
z), 6.65 (2H, br.d, J=8.9Hz), 5.39 (2H, s), 3.48
(2H, br.s). （３）Ｎ−［４−（５−フルオロベンゾチアゾール−
２−イルメトキシ）フェニル］ブチルアミド（化合物番
号Ｆ４．１９）（工程Ｂ−４）上記（２）の方法で製造された４−（５−フルオロベン
ゾチアゾール−２−イルメトキシ）アニリン１５０．８
ｍｇを塩化メチレン３ｍｌに溶解し、氷水浴中、０．０
９ｍｌのトリエチルアミンと０．０７ｍｌの塩化ブチリ
ルを加えた後、室温に昇温し１時間撹拌した。反応液中
に水を加え、塩化メチレンで抽出した。抽出液を、水、
塩化ナトリウム水溶液で洗浄後、硫酸ナトリウムで乾燥
した。ろ過後、溶媒を留去し、得られた粗結晶を塩化メ
チレン−ヘキサン混合溶媒より再結晶し、融点２０１〜
２０２℃を有する標記化合物１０４．５ｍｇ（収率５５
％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.84 (1H, dd, J = 9.0, 4.7Hz), 7.72 (1H, dd, J = 9.5,
2.5Hz), 7.23-7.12 (1H, m), 6.87 (2H, br.d, J = 8.8H
z), 6.65 (2H, br.d, J = 8.9Hz), 5.39 (2H, s), 3.48
(2H, br.s). (3) N- [4- (5-fluorobenzothiazole-
2-ylmethoxy) phenyl] butyramide (compound number
(Step F -4) 4- (5-fluorobenzothiazol-2-ylmethoxy) aniline 150.8 produced by the method of (2) above.
mg in 3 ml of methylene chloride and placed in an ice water bath at 0.0
After adding 9 ml of triethylamine and 0.07 ml of butyryl chloride, the mixture was heated to room temperature and stirred for 1 hour. Water was added to the reaction solution, and extracted with methylene chloride. Extract, water,
After washing with an aqueous sodium chloride solution, the extract was dried over sodium sulfate. After filtration, the solvent was distilled off, and the obtained crude crystals were recrystallized from a methylene chloride-hexane mixed solvent to give a melting point of
104.5 mg of the title compound having a temperature of 202 ° C. (yield 55
%).

【０２６６】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.82 (1H, dd, J=8.8, 5.1Hz), 7.70(1H, dd, J=9.5,
2.5Hz), 7.45 (2H, d, J=9.0Hz), 7.18 (1H, td, J=8.9
Hz, 2.5Hz), 7.02 (1H, br.s), 6.99 (2H, d, J=9.2H
z), 5.45 (2H, s), 2.32 (2H, t, J=7.5Hz), 1.76 (2H,
sextet, J=7.3Hz), 1.01 (2H, t, J=7.4Hz).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.82 (1H, dd, J = 8.8, 5.1Hz), 7.70 (1H, dd, J = 9.5,
2.5Hz), 7.45 (2H, d, J = 9.0Hz), 7.18 (1H, td, J = 8.9
Hz, 2.5Hz), 7.02 (1H, br.s), 6.99 (2H, d, J = 9.2H
z), 5.45 (2H, s), 2.32 (2H, t, J = 7.5Hz), 1.76 (2H,
sextet, J = 7.3Hz), 1.01 (2H, t, J = 7.4Hz).

【０２６７】[0267]

【実施例１０】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］−Ｎ−メチルアセトアミド（化合物番号Ｂ１．
１）（工程Ｂ−５）上記実施例１の方法により製造されたＮ−［４−（ベン
ゾチアゾール−２−イルメトキシ）フェニル］アセトア
ミド１０２．０ｍｇを２ｍｌのＤＭＦに溶解し、氷水浴
中、６０％水素化ナトリウム１５．１ｍｇを加え、５分
間撹袢した後、０．０２３ｍｌの沃化メチルを加えた。
室温にまで昇温後、１．５時間撹袢した。飽和塩化アン
モニウム水溶液を加え、酢酸エチルで抽出し、水、食塩
水で洗浄後、無水硫酸ナトリウムで乾燥させた。ろ過
後、溶媒を留去し、シリカゲルカラムクロマトグラフィ
ー（溶出溶媒ヘキサン：酢酸エチル＝１：１）で精製
し、融点１１９〜１２０℃を有する標記化合物１０６．
８ｍｇ（収率１００％）を得た。Example 10 N- [4- (benzothiazol-2-ylmethoxy) phenyl
Enyl] -N-methylacetamide (Compound No. B1.
1) (Step B-5) 102.0 mg of N- [4- (benzothiazol-2-ylmethoxy) phenyl] acetamide prepared by the method of Example 1 above was dissolved in 2 ml of DMF, and dissolved in an ice water bath. After adding 15.1 mg of sodium hydride and stirring for 5 minutes, 0.023 ml of methyl iodide was added.
After the temperature was raised to room temperature, the mixture was stirred for 1.5 hours. A saturated aqueous solution of ammonium chloride was added, extracted with ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 1) to give the title compound having a melting point of 119 to 120 ° C.
8 mg (100% yield) was obtained.

【０２６８】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.05 (1H, br.d, J=7.7Hz), 7.92 (1H, br.d, J=8.3H
z), 7.65-7.38 (2H, m), 7.15 (2H, d, J=9.0Hz), 7.05
(2H, d, J=9.0Hz), 5.51 (2H, s), 3.22 (3H, s), 1.8
5 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.05 (1H, br.d, J = 7.7Hz), 7.92 (1H, br.d, J = 8.3H
z), 7.65-7.38 (2H, m), 7.15 (2H, d, J = 9.0Hz), 7.05
(2H, d, J = 9.0Hz), 5.51 (2H, s), 3.22 (3H, s), 1.8
5 (3H, s).

【０２６９】[0269]

【実施例１１】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）フェニル］カルバマート（化合物番号Ａ１．５）
（工程Ｂ−４）上記実施例３（２）の方法により得た４−（ベンゾチア
ゾール−２−イルメトキシ）アニリン２５０ｍｇを塩化
メチレン５ｍｌに溶解し、氷水浴中、０．１４ｍｌのト
リエチルアミンと０．０８ｍｌのクロロ蟻酸メチルを加
え５０分間撹袢し、更に室温に昇温後３０分間撹拌し
た。反応液中に水を加え、塩化メチレンで抽出した後、
水で洗浄し、硫酸ナトリウムで乾燥した。ろ過後、溶媒
を留去し、シリカゲルカラムクロマトグラフィー（溶出
溶媒ヘキサン：酢酸エチル＝３：１）で精製し、融点
１４２〜１４４℃を有する標記化合物２４３．１ｍｇ
（収率７９％）を得た。Example 11 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) phenyl] carbamate (Compound No. A1.5)
(Step B-4) 250 mg of 4- (benzothiazol-2-ylmethoxy) aniline obtained by the method of Example 3 (2) is dissolved in 5 ml of methylene chloride, and 0.14 ml of triethylamine and 0.1 mg of 0.1% are dissolved in an ice water bath. 08 ml of methyl chloroformate was added, the mixture was stirred for 50 minutes, and the temperature was raised to room temperature, followed by stirring for 30 minutes. After adding water to the reaction solution and extracting with methylene chloride,
Washed with water and dried over sodium sulfate. After filtration, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 3: 1) to give 243.1 mg of the title compound having a melting point of 142 to 144 ° C.
(79% yield).

【０２７０】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.03 (1H, dd, J=8.8, 1.5Hz), 7.90(1H, dd, J=6.9,
1.0Hz), 7.54-7.36 (2H,m), 7.15 (4H, m), 6.48 (1H,
br.s), 5.46 (2H, s), 3.76 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.03 (1H, dd, J = 8.8, 1.5Hz), 7.90 (1H, dd, J = 6.9,
1.0Hz), 7.54-7.36 (2H, m), 7.15 (4H, m), 6.48 (1H,
br.s), 5.46 (2H, s), 3.76 (3H, s).

【０２７１】[0271]

【実施例１２】エチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）フェニル］カルバマート（化合物番号Ａ１．２
１）（工程Ｂ−４）上記実施例３（２）の方法により得た４−（ベンゾチア
ゾール−２−イルメトキシ）アニリン２５０ｍｇを塩化
メチレン５ｍｌに溶解し、氷水浴中、０．１４ｍｌのト
リエチルアミンと０．０８ｍｌのクロロ蟻酸エチルを加
え１．５時間撹拌した。反応液中に水を加え、塩化メチ
レンで抽出した後、水で洗浄し、硫酸ナトリウムで乾燥
した。ろ過後、溶媒を留去し、シリカゲルカラムクロマ
トグラフィー（溶出溶媒ヘキサン：酢酸エチル＝３：
１）で精製し、融点１４９〜１５０℃を有する標記化合
物２８４．８ｍｇ（収率８８％）を得た。Example 12 Ethyl N- [4- (benzothiazol-2-ylmethoate)
Xy) phenyl] carbamate (Compound No. A1.2
1) (Step B-4) 250 mg of 4- (benzothiazol-2-ylmethoxy) aniline obtained by the method of Example 3 (2) was dissolved in 5 ml of methylene chloride, and 0.14 ml of triethylamine was dissolved in an ice water bath. 0.08 ml of ethyl chloroformate was added and stirred for 1.5 hours. Water was added to the reaction solution, extracted with methylene chloride, washed with water, and dried over sodium sulfate. After filtration, the solvent was distilled off and the residue was subjected to silica gel column chromatography (elution solvent: hexane: ethyl acetate = 3:
Purification in 1) gave 284.8 mg (88% yield) of the title compound having a melting point of 149-150 ° C.

【０２７２】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.03 (1H, d, J=5.9Hz), 7.90 (1H,dd, J=7.6, 0.9H
z), 7.54-7.36 (2H, m), 7.15 (4H, m), 6.47 (1H, br.
s), 5.50 (2H, s), 4.21 (2H, q, J=7.2Hz), 1.30 (3H,
t, J=7.0Hz).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.03 (1H, d, J = 5.9Hz), 7.90 (1H, dd, J = 7.6, 0.9H
z), 7.54-7.36 (2H, m), 7.15 (4H, m), 6.47 (1H, br.
s), 5.50 (2H, s), 4.21 (2H, q, J = 7.2Hz), 1.30 (3H,
t, J = 7.0Hz).

【０２７３】[0273]

【実施例１３】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）フェニル］−Ｎ−メチルカルバマート（化合物番
号Ｂ１．３）（工程Ｂ−５）上記実施例１１の方法により得たメチルＮ−［４−
（ベンゾチアゾール−２−イルメトキシ）フェニル］カ
ルバマート１３８．６ｍｇをＤＭＦ５ｍｌに溶解後、氷
水浴中、沃化メチル０．２７ｍｌを加え、更に６０％水
素化ナトリウム１９．４ｍｇを加えた。１０分間撹袢し
た後、室温に昇温し、３０分間撹拌し、反応液中に水を
加え、酢酸エチルで抽出した後、水、塩化ナトリウム水
溶液で洗浄し、硫酸ナトリウムで乾燥した。ろ過後、溶
媒を留去し、得られた粗結晶をシリカゲルカラムクロマ
トグラフィー（溶出溶媒ヘキサン：酢酸エチル＝２：
１）で精製し、融点８５〜８７℃を有する標記化合物１
２６．７ｍｇ（８７％）を得た。Example 13 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) phenyl] -N-methylcarbamate (Compound No.
No. B1.3) (Step B-5) Methyl N- [4-
After 138.6 mg of (benzothiazol-2-ylmethoxy) phenyl] carbamate was dissolved in 5 ml of DMF, 0.27 ml of methyl iodide was added in an ice water bath, and 19.4 mg of 60% sodium hydride was further added. After stirring for 10 minutes, the mixture was heated to room temperature, stirred for 30 minutes, water was added to the reaction solution, extracted with ethyl acetate, washed with water and an aqueous sodium chloride solution, and dried over sodium sulfate. After filtration, the solvent was distilled off, and the resulting crude crystals were subjected to silica gel column chromatography (elution solvent: hexane: ethyl acetate = 2:
The title compound 1 which is purified in 1) and has a melting point of 85-87 ° C.
26.7 mg (87%) were obtained.

【０２７４】ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐ
ｍ：８．０４（１Ｈ，ｄｄ，Ｊ＝８．７，
１．２Ｈｚ），７．９１（１Ｈ，ｄｄ，Ｊ＝６．
８，０．９Ｈｚ），７．５６−７．４１（２Ｈ，
ｍ），７．１７（２Ｈ，ｄ，Ｊ＝９．０Ｈ
ｚ），７．０６−６．９９（２Ｈ，ｍ），５．
４８（２Ｈ，ｓ），３．６９（３Ｈ，ｓ），
３．２６（３Ｈ，ｓ）．NMR spectrum (200 MHz, CDCl ₃ ), δpp
m: 8.04 (1H, dd, J = 8.7,
1.2 Hz), 7.91 (1H, dd, J = 6.
8, 0.9 Hz), 7.56-7.41 (2H,
m), 7.17 (2H, d, J = 9.0H
z), 7.06-6.99 (2H, m), 5.
48 (2H, s), 3.69 (3H, s),
3.26 (3H, s).

【０２７５】[0275]

【実施例１４】Ｓ−メチルＮ−［４−（ベンゾチアゾール−２−イル
メトキシ）−２−メチルフェニル］ジチオカルバマート
（化合物番号Ｃ１．１３）（工程Ｂ−４）下記実施例２１（２）の方法により得た４−（ベンゾチ
アゾール−２−イルメトキシ）−２−メチルアニリン５
００ｍｇと水酸化カリウム１１４．５ｍｇをＤＭＦ６ｍ
ｌと水６ｍｌに溶解後、氷水浴中撹袢し、二硫化炭素
０．１３ｍｌを加えて１０分間撹袢した。室温に昇温
後、更に３０分間撹袢した。再び、氷水浴中冷却し、沃
化メチル０．１５ｍｌを加え１０分間撹袢した。室温に
昇温後、２．５時間撹袢した。水を加え、酢酸エチルで
抽出し、水洗後、無水硫酸ナトリウムで乾燥した。ろ過
後、溶媒を留去し、得られた粗結晶をシリカゲルカラム
クロマトグラフィー（溶出溶媒ヘキサン：酢酸エチル
＝３：１）で精製し、融点１３３〜１３５℃を有する標
記化合物４５８．２ｍｇ（６８％）を得た。Example 14 S-methyl N- [4- (benzothiazol-2-yl
Methoxy) -2-methylphenyl] dithiocarbamate
(Compound No. C1.13) (Step B-4) 4- (benzothiazol-2-ylmethoxy) -2-methylaniline 5 obtained by the method of Example 21 (2) below
00 mg and 114.5 mg of potassium hydroxide in 6 m of DMF
After dissolving in water and 6 ml of water, the mixture was stirred in an ice water bath, 0.13 ml of carbon disulfide was added, and the mixture was stirred for 10 minutes. After the temperature was raised to room temperature, the mixture was further stirred for 30 minutes. The mixture was cooled again in an ice water bath, and 0.15 ml of methyl iodide was added thereto, followed by stirring for 10 minutes. After the temperature was raised to room temperature, the mixture was stirred for 2.5 hours. Water was added, extracted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the resulting crude crystals were purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 3: 1) to give 458.2 mg (68%) of the title compound having a melting point of 133 to 135 ° C. ) Got.

【０２７６】ＮＭＲスペクトル（２００ＭＨｚ，ＣＤＣ
ｌ_３）， δppm: 8.70-8.60 (1H, br.m), 8.04 (1H,
d, J=8.1Hz), 7.91 (1H, dd, J=11.1, 7.3Hz), 7.56-7.
38 (2H, m), 7.24 (1H, d, J=9.9Hz), 6.97-6.88 (2H,
m), 5.49 (2H, s), 2.62 (3H, s), 2.28 (3H, s).An NMR spectrum (200 MHz, CDC
_{l 3), δppm: 8.70-8.60 (} 1H, br.m), 8.04 (1H,
d, J = 8.1Hz), 7.91 (1H, dd, J = 11.1, 7.3Hz), 7.56-7.
38 (2H, m), 7.24 (1H, d, J = 9.9Hz), 6.97-6.88 (2H,
m), 5.49 (2H, s), 2.62 (3H, s), 2.28 (3H, s).

【０２７７】[0277]

【実施例１５】メチルＮ−［４−（６−フルオロベンゾチアゾ−ル−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト（化合物番号Ｇ１．６２）（１）メチルＮ−（４−ヒドロキシ−２−メチルフ
ェニル）カルバマート（工程Ｂ−４）４−アミノ−３−メチルフェノ−ル１００ｇをアセトン
４００ｍｌに溶解し、氷冷下、炭酸カリウム１２．０ｇ
を加え、次いで、クロロ蟻酸メチル８０ｍｌを加え、同
温度で３時間攪拌した。反応終了後、反応混合物をろ過
し、ろ液を減圧下に濃縮して、アモルファスとして標記
化合物１５１ｇ（収率１００％）を得た。ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.22 (1H, b
r.s), 6.61-6.52 (2H, m), 6.26 (2H, br.s), 3.76 (3
H, s), 2.17 (3H, s). （２）メチルＮ−［４−（６−フルオロベンゾチア
ゾ−ル−２−イルメトキシ）−２−メチルフェニル］カ
ルバマート（化合物番号Ｇ１．６２）（工程Ａ−１）上記（１）の方法により得たメチルＮ−［４−ヒドロ
キシ−２−メチルフェニル］カルバマート６２．６ｍｇ
をＤＭＦ４ｍｌに溶解後、氷水浴中６０％水素化ナトリ
ウム１５．２ｍｇを加えた。１０分間撹袢した後、上記
実施例５（３）の方法により得た６−フルオロ−２−メ
タンスルホニルオキシメチルベンゾチアゾール１００．
０ｍｇを加え、室温に昇温後、３時間撹拌し、反応液中
に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽
出した。抽出液を、水で洗浄後、無水硫酸ナトリウムで
乾燥した。ろ過後、溶媒を留去し、得られた粗結晶をシ
リカゲルカラムクロマトグラフィー（溶出溶媒ヘキサ
ン：酢酸エチル＝３：１）で精製し、更に得られた結晶
をエチルエーテルで洗浄し、融点１４９〜１５１℃を有
する標記化合物４１．４ｍｇ（３５％）を得た。Example 15 Methyl N- [4- (6-fluorobenzothiazol-)
2-ylmethoxy) -2-methylphenyl] carbamer
(Compound No. G1.62) (1) Methyl N- (4-hydroxy-2-methylf)
Enyl) carbamate (Step B-4) 100 g of 4-amino-3-methylphenol are dissolved in 400 ml of acetone, and 12.0 g of potassium carbonate is added under ice cooling.
Was added, and then 80 ml of methyl chloroformate was added, followed by stirring at the same temperature for 3 hours. After completion of the reaction, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 151 g (yield 100%) of the title compound as amorphous. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.22 (1H, b
rs), 6.61-6.52 (2H, m), 6.26 (2H, br.s), 3.76 (3
H, s), 2.17 (3H, s). (2) Methyl N- [4- (6-fluorobenzothia
Zol-2-ylmethoxy) -2-methylphenyl] ca
Rubamate (Compound No. G1.62) (Step A-1) 62.6 mg of methyl N- [4-hydroxy-2-methylphenyl] carbamate obtained by the method of the above (1).
Was dissolved in 4 ml of DMF, and 15.2 mg of 60% sodium hydride was added in an ice water bath. After stirring for 10 minutes, 6-fluoro-2-methanesulfonyloxymethylbenzothiazole obtained by the method of Example 5 (3) above was used.
After adding 0 mg, the mixture was heated to room temperature and stirred for 3 hours, a saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the obtained crude crystals were purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 3: 1), and the obtained crystals were washed with ethyl ether to give a melting point of 149 ° C. 41.4 mg (35%) of the title compound having 151 ° C. were obtained.

【０２７８】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.00-7.93 (1H, m), 7.66-7.54 (2H,m), 7.38-7.31 (1
H, br.m), 6.89-6.86 (2H, m), 6.22-6.20 (1H, br.m),
5.43(2H, s), 3.76 (3H, s), 2.24 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.00-7.93 (1H, m), 7.66-7.54 (2H, m), 7.38-7.31 (1
H, br.m), 6.89-6.86 (2H, m), 6.22-6.20 (1H, br.m),
5.43 (2H, s), 3.76 (3H, s), 2.24 (3H, s).

【０２７９】[0279]

【実施例１６】Ｏ−メチルＮ−［４−（ベンゾチアゾール−２−イル
メトキシ）フェニル］チオカルバマート（化合物番号Ａ
１．９）（工程Ｂ−４）上記実施例３（２）の方法により得た４−（ベンゾチア
ゾール−２−イルメトキシ）アニリン５０．２ｍｇを塩
化メチレン２ｍｌに溶解し、炭酸水素ナトリウム２０．
８ｍｌとチオホスゲンを０．０５ｍｌ加え、室温下２時
間撹袢した。反応溶液を塩化メチレンで希釈し、水で洗
浄後、無水硫酸ナトリウムで乾燥した。ろ過後、溶媒を
留去し、得た残さをテトラヒドロフラン（ＴＨＦ）３ｍ
ｌに溶解し、メチルアルコール０．０１ｍｌと６０％水
素化ナトリウム１３．２ｍｇを加え、３０分間撹袢し
た。更にナトリウムメチラート５ｍｇを加え、３０分間
撹袢した後、塩化ナトリウム水溶液を加え、酢酸エチル
で抽出した。抽出液を、塩化ナトリウム水溶液で洗浄
後、無水硫酸ナトリウムで乾燥した。ろ過後、溶媒を留
去し、得た粗結晶を、酢酸エチル−ヘキサンの混合溶剤
で再結晶することにより、融点１６０〜１６２℃を有す
る標記化合物４９．７ｍｇ（７６％）を得た。Example 16 O-methyl N- [4- (benzothiazol-2-yl
Methoxy) phenyl] thiocarbamate (Compound No. A
1.9) (Step B-4) 40.2 mg of 4- (benzothiazol-2-ylmethoxy) aniline obtained by the method of Example 3 (2) above was dissolved in 2 ml of methylene chloride, and sodium hydrogencarbonate 20.
8 ml and 0.05 ml of thiophosgene were added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with methylene chloride, washed with water, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the obtained residue was treated with tetrahydrofuran (THF) 3m
Then, 0.01 ml of methyl alcohol and 13.2 mg of 60% sodium hydride were added, and the mixture was stirred for 30 minutes. Further, 5 mg of sodium methylate was added, and after stirring for 30 minutes, an aqueous solution of sodium chloride was added, followed by extraction with ethyl acetate. The extract was washed with an aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate-hexane to give 49.7 mg (76%) of the title compound having a melting point of 160 to 162 ° C.

【０２８０】ＮＭＲスペクトル(200MHz,DMSO-d₆), δpp
m: 11.02 (1H, br.s), 8.16-8.02 (2H, m), 7.60-7.44
(3H, m), 7.30-7.24 (1H, m), 7.14-7.07 (2H, m), 5.6
1 (2H,s), 3.96 (3H, br.s).NMR spectrum (200 MHz, DMSO-d ₆ ), δpp
m: 11.02 (1H, br.s), 8.16-8.02 (2H, m), 7.60-7.44
(3H, m), 7.30-7.24 (1H, m), 7.14-7.07 (2H, m), 5.6
1 (2H, s), 3.96 (3H, br.s).

【０２８１】[0281]

【実施例１７】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−３−クロロフェニル］カルバマート（化合物番
号Ｃ９．５５）（１）メチルＮ−（３−クロロ−４−ヒドロキシフ
ェニル）カルバマート（工程Ｂ−４）４−アミノ−２−クロロフェノール１．７０ｇに水５ｍ
ｌと１０％水酸化ナトリウム水溶液２．５ｍｌを、氷冷
下静かに加え、クロロ蟻酸メチル２ｍｌを滴下した。室
温で３時間撹袢した後、２Ｎ−塩酸４ｍｌで酸性にし、
塩化メチレンで抽出した。抽出液を、水で洗浄後、無水
硫酸ナトリウムで乾燥した。ろ過後、溶媒を留去し、得
られた粗結晶をシリカゲルカラムクロマトグラフィーで
精製し、うす茶色結晶の標記化合物２．０８ｇ（収率８
７％）を得た。Example 17 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -3-chlorophenyl] carbamate (compound number
No. C9.55) (1) Methyl N- (3-chloro-4-hydroxy )
Enyl) carbamate (Step B-4) 4-amino-2-chlorophenol 1.70 g and water 5 m
and 2.5 ml of a 10% aqueous sodium hydroxide solution were gently added under ice-cooling, and 2 ml of methyl chloroformate was added dropwise. After stirring at room temperature for 3 hours, the mixture was acidified with 4 ml of 2N hydrochloric acid,
Extracted with methylene chloride. The extract was washed with water and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the obtained crude crystals were purified by silica gel column chromatography to give the title compound (2.08 g, light brown crystals, yield 8).
7%).

【０２８２】（２）メチルＮ−［４−（ベンゾチア
ゾール−２−イルメトキシ）−３−クロロフェニル］カ
ルバマート（化合物番号Ｃ９．５５）（工程Ａ−１）上記（１）の方法により得たメチルＮ−（３−クロロ
−４−ヒドロキシフェニル）カルバマート２０３．６ｍ
ｇをＤＭＦ４ｍｌに溶解後、氷水浴中６０％水素化ナト
リウム４４．４ｍｇを加えた。３分間撹拌した後、２−
ブロモメチルベンゾチアゾール２４１．９ｍｇを加え
た。室温に昇温後、１．５時間撹拌し、反応液中に飽和
塩化アンモニウム水溶液を加え、酢酸エチルで抽出し、
水、飽和塩化ナトリウム水溶液で洗浄後、無水硫酸ナト
リウムで乾燥した。ろ過後、溶媒を留去し、得られた粗
結晶をシリカゲルカラムクロマトグラフィー（溶出溶媒
ヘキサン：酢酸エチル＝２：１）で精製し、融点１３
３〜１３５℃を有する標記化合物の２８６．９ｍｇ（収
率８１％）を得た。(2) Methyl N- [4- (benzothia)
Zol-2-ylmethoxy) -3-chlorophenyl] ca
Rubamate (Compound No. C9.55) (Step A-1) 203.6 m of methyl N- (3-chloro-4-hydroxyphenyl) carbamate obtained by the method of the above (1)
g was dissolved in 4 ml of DMF, and 44.4 mg of 60% sodium hydride was added in an ice water bath. After stirring for 3 minutes,
241.9 mg of bromomethylbenzothiazole were added. After heating to room temperature, the mixture was stirred for 1.5 hours, a saturated aqueous solution of ammonium chloride was added to the reaction solution, and the mixture was extracted with ethyl acetate.
After washing with water and a saturated aqueous sodium chloride solution, the extract was dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the resulting crude crystals were purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 2: 1) to give a melting point of 13
286.9 mg (81% yield) of the title compound having a temperature of 3-135 ° C. were obtained.

【０２８３】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.03 (1H, br.d, J=7.0Hz), 7.92 (1H, br.d, J=7.6H
z), 7.58-7.37 (3H, m), 7.18 (1H, dd, J=8.8, 2.7H
z), 7.00(1H, d, J=8.9Hz), 6.53 (1H, br.s), 5.51 (2
H, s), 3.77 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.03 (1H, br.d, J = 7.0Hz), 7.92 (1H, br.d, J = 7.6H
z), 7.58-7.37 (3H, m), 7.18 (1H, dd, J = 8.8, 2.7H
z), 7.00 (1H, d, J = 8.9Hz), 6.53 (1H, br.s), 5.51 (2
H, s), 3.77 (3H, s).

【０２８４】[0284]

【実施例１８】メチルＮ−（２−ヒドロキシエチル）−Ｎ−［２−メ
チル−４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］カルバマート（化合物番号Ｄ１．１０６）（工
程Ｂ−７）下記実施例２１により得たメチルＮ−［４−（ベンゾ
チアゾール−２−イルメトキシ）−２−メチルフェニ
ル］カルバマート及び２−（２−テトラヒドロピラニル
オキシ）エチルから上記実施例１３の方法に準じて製造
したメチルＮ−［２−（２−テトラヒドロピラニルオ
キシ）エチル）］−Ｎ−［２−メチル−４−（ベンゾチ
アゾール−２−イルメトキシ）フェニル］カルバマート
（化合物番号Ｄ１．１１９）６５８．１ｍｇを６．６ｍ
ｌのメタノールに溶解し、ｐ−トルエンスルホン酸一水
和物を触媒量（約１０ｍｇ）加え、室温下、２時間攪拌
した。反応溶液に水を加え、酢酸エチルで抽出した後、
水、飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。
ろ過後、溶媒を留去し、シリカゲルカラムクロマトグラ
フィー（溶出溶媒ヘキサン：酢酸エチル＝１：２）で
精製し、融点１０９〜１１０℃を有する標記化合物７０
２．５ｍｇ（収率９４．１％）を得た。Example 18 Methyl N- (2-hydroxyethyl) -N- [2-meth
Tyl-4- (benzothiazol-2-ylmethoxy) phenyl
Enyl] carbamate (Compound No. D1.106) (Step B-7) Methyl N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] carbamate and 2- (2- Methyl N- [2- (2-tetrahydropyranyloxy) ethyl)]-N- [2-methyl-4- (benzothiazole-2) prepared from tetrahydropyranyloxy) ethyl according to the method of Example 13 above. -Ylmethoxy) phenyl] carbamate (Compound No. D1.119) 658.1 mg in 6.6 m
The mixture was dissolved in 1 l of methanol, p-toluenesulfonic acid monohydrate was added in a catalytic amount (about 10 mg), and the mixture was stirred at room temperature for 2 hours. After adding water to the reaction solution and extracting with ethyl acetate,
The extract was washed with water and saturated saline and dried over sodium sulfate.
After filtration, the solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 2) to give the title compound 70 having a melting point of 109 to 110 ° C.
2.5 mg (94.1% yield) were obtained.

【０２８５】ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐ
ｍ：８．０４（１Ｈ，ｄ，Ｊ＝８．２Ｈｚ），
７．９２（１Ｈ，ｄ，Ｊ＝７．９Ｈｚ），７．
５７−７．３７（２Ｈ，ｍ），７．１９−６．８
０（３Ｈ，ｍ），５．４７（２Ｈ，ｓ），
４．０２−３．４２（４Ｈ，ｍ），３．６６
（３Ｈ，ｓ），２．７０−２．６０（１Ｈ，
ｍ），２．２１（３Ｈ，ｓ）．NMR spectrum (200 MHz, CDCl ₃ ), δpp
m: 8.04 (1H, d, J = 8.2 Hz),
7.92 (1H, d, J = 7.9 Hz);
57-7.37 (2H, m), 7.19-6.8
0 (3H, m), 5.47 (2H, s),
4.02-3.42 (4H, m), 3.66
(3H, s), 2.70-2.60 (1H,
m), 2.21 (3H, s).

【０２８６】[0286]

【実施例１９】メチルＮ−ヒドロキシメチル−Ｎ−［２−メチル−４
−（ベンゾチアゾール−２−イルメトキシ）フェニル］
カルバマート（化合物番号Ｄ１．４７）（工程Ｂ−５）下記実施例２１（３）により得たメチルＮ−［２−メ
チル−４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］カルバマート１０．０１ｇとパラホルムアルデ
ヒド５．０ｇにアセトン１３０ｍｌと水０．５ｍｌの混
合溶媒を室温で加え、さらに０．３０ｇの炭酸カリウム
を加えた後、超音波の照射下、３０℃で１２時間撹袢し
た。反応溶液をろ過し、溶媒を留去後、シリカゲルカラ
ムクロマトグラフィー（溶出溶媒塩化メチレン：アセ
トン＝９：１〜８：２）で精製し、融点１２１〜１２３
℃を有する標記化合物８．０２ｇ（収率７３．４％）を
得た。Example 19: Methyl N-hydroxymethyl-N- [2-methyl-4
-(Benzothiazol-2-ylmethoxy) phenyl]
Carbamate (Compound No. D1.47) (Step B-5) 10.01 g of methyl N- [2-methyl-4- (benzothiazol-2-ylmethoxy) phenyl] carbamate obtained by the following Example 21 (3) was added A mixed solvent of 130 ml of acetone and 0.5 ml of water was added to 5.0 g of formaldehyde at room temperature, and 0.30 g of potassium carbonate was further added. Then, the mixture was stirred at 30 ° C. for 12 hours under ultrasonic irradiation. After the reaction solution was filtered and the solvent was distilled off, the residue was purified by silica gel column chromatography (elution solvent: methylene chloride: acetone = 9: 1 to 8: 2) to give a melting point of 121 to 123.
8.02 g (yield 73.4%) of the title compound having a temperature of ° C. were obtained.

【０２８７】ＮＭＲスペクトル（２００ＭＨｚ，ＣＤＣ
ｌ_３）， δppm: 8.06-7.88 (2H, m), 7.55-7.37 (2H,
m), 7.14 (1H, d, J=8.4Hz), 6.93 (1H, d, J=3.0Hz),
6.86 (1H, dd, J=8.4,3.0Hz), 5.47 (2H, s), 5.20-5.1
1 (1H, m), 4.84-4.75 (1H, m), 3.90-3.62 (3H, m),
3.51-3.43 (1H, m), 2.22 (3H, s).An NMR spectrum (200 MHz, CDC
_{l 3), δppm: 8.06-7.88 (} 2H, m), 7.55-7.37 (2H,
m), 7.14 (1H, d, J = 8.4Hz), 6.93 (1H, d, J = 3.0Hz),
6.86 (1H, dd, J = 8.4,3.0Hz), 5.47 (2H, s), 5.20-5.1
1 (1H, m), 4.84-4.75 (1H, m), 3.90-3.62 (3H, m),
3.51-3.43 (1H, m), 2.22 (3H, s).

【０２８８】[0288]

【実施例２０】メチルＮ−ブトキシメチル−Ｎ−［４−（ベンゾチア
ゾール−２−イルメトキシ）−２−メチルフェニル］カ
ルバマート（化合物番号Ｄ１．５７）（工程Ｂ−７）上記実施例１９により得たメチルＮ−ヒドロキシメチ
ル−Ｎ−［４−（ベンゾチアゾール−２−イルメトキ
シ）−２−メチルフェニル］カルバマート４９．８ｍｇ
をブチルアルコール２ｍｌに溶解し、濃硫酸でｐＨ３に
調製した。触媒量（２ｍｇ）のヒドロキノンを加え、８
５℃にて１時間攪拌した。放冷後、炭酸水素ナトリウム
水溶液を加え、酢酸エチルで抽出した。抽出液を飽和食
塩水で洗浄後、無水硫酸ナトリウムで乾燥し、ろ過後、
減圧下、溶媒を留去して、オイル状の標記化合物を５
５．７ｍｇ（収率９３．５％）得た。Example 20: Methyl N-butoxymethyl-N- [4- (benzothia
Zol-2-ylmethoxy) -2-methylphenyl] ca
Rubamate (Compound No. D1.57) (Step B-7) 49.8 mg of methyl N-hydroxymethyl-N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] carbamate obtained in Example 19 above.
Was dissolved in 2 ml of butyl alcohol and adjusted to pH 3 with concentrated sulfuric acid. A catalytic amount (2 mg) of hydroquinone was added and 8
The mixture was stirred at 5 ° C for 1 hour. After cooling, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated saline, dried over anhydrous sodium sulfate, filtered,
The solvent was distilled off under reduced pressure to give the title compound as an oil.
5.7 mg (93.5% yield) was obtained.

【０２８９】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.07-7.89 (2H, m), 7.55-7.37 (2H,m), 7.09 (1H, d,
J=8.4Hz), 6.92 (1H, d, J=3.0Hz), 6.86 (1H, dd, J=
8.4,2.8Hz), 5.46 (2H, s), 4.96 (2H, ABq, J=10.4Hz,
Δν=106.1Hz), 3.82-3.50 (5H, m), 2.18 (3H, s), 1.
60-1.27 (4H, m), 0.91 (3H, t, J=7.2Hz).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.07-7.89 (2H, m), 7.55-7.37 (2H, m), 7.09 (1H, d,
J = 8.4Hz), 6.92 (1H, d, J = 3.0Hz), 6.86 (1H, dd, J =
8.4,2.8Hz), 5.46 (2H, s), 4.96 (2H, ABq, J = 10.4Hz,
Δν = 106.1Hz), 3.82-3.50 (5H, m), 2.18 (3H, s), 1.
60-1.27 (4H, m), 0.91 (3H, t, J = 7.2Hz).

【０２９０】[0290]

【実施例２１】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］カルバマート（化合物番
号Ｃ１．５）（１）Ｏ−（ベンゾチアゾール−２−イルメチル）−
３−メチル−４−ニトロフェノール（工程Ａ−１）３−メチル−４−ニトロフェノール８０．０ｇをＤＭＦ
７００ｍｌに溶解後、氷浴中６０％水素化ナトリウム２
３．０ｇを加えた。２０分間撹拌した後、２−クロロメ
チルベンゾチアゾール９５．９ｇの５０ｍｌＤＭＦ溶液
を加えた。８０℃に昇温後、２時間撹拌し、反応溶液を
氷水中に静かに加え、析出した結晶を水洗した。得られ
た粗結晶をトルエンで再結晶し、融点１４５〜１４７℃
を有する標記化合物９８．８ｇ（収率６３％）を得た。Example 21 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] carbamate (compound number
No. C1.5) (1) O- (benzothiazol-2-ylmethyl)-
3-Methyl-4-nitrophenol (Step A-1) 80.0 g of 3-methyl-4-nitrophenol was added to DMF.
After dissolving in 700 ml, 60% sodium hydride 2
3.0 g were added. After stirring for 20 minutes, a solution of 95.9 g of 2-chloromethylbenzothiazole in 50 ml of DMF was added. After the temperature was raised to 80 ° C., the mixture was stirred for 2 hours, the reaction solution was gently added to ice water, and the precipitated crystals were washed with water. The obtained crude crystals were recrystallized from toluene, and the melting point was 145 to 147 ° C.
98.8 g (yield 63%) of the title compound having the formula was obtained.

【０２９１】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.08 (1H, d, J=9.8Hz), 8.05 (1H,dd, J=8.9, 1.5H
z), 7.91 (1H, dd, J=7.7, 1.5Hz), 7.57-7.39 (2H,
m), 6.99-6.93 (2H, m), 5.56 (2H, s), 2.63 (3H, s). （２）４−（ベンゾチアゾール−２−イルメトキシ）
−２−メチルアニリン（工程Ｂ−３）上記（１）の方法で製造されたＯ−（ベンゾチアゾール
−２−イルメチル）−３−メチル−４−ニトロフェノー
ル３５．０ｇをＴＨＦ５００ｍｌに溶解させ、二酸化白
金１．０ｇを加えた後、水素雰囲気下室温にて２時間激
しく撹拌した。反応溶液にセライトを加えてろ過した
後、ろ液を濃縮し、残渣をジイソプロピルエーテルで洗
浄し、融点１１０〜１１１℃を有する標記化合物３２．
１ｇ（収率１００％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.08 (1H, d, J = 9.8Hz), 8.05 (1H, dd, J = 8.9, 1.5H
z), 7.91 (1H, dd, J = 7.7, 1.5Hz), 7.57-7.39 (2H,
m), 6.99-6.93 (2H, m), 5.56 (2H, s), 2.63 (3H, s). (2) 4- (benzothiazol-2-ylmethoxy)
-2-Methylaniline (Step B-3) 35.0 g of O- (benzothiazol-2-ylmethyl) -3-methyl-4-nitrophenol produced by the method of (1) is dissolved in 500 ml of THF, and After adding 1.0 g of platinum, the mixture was vigorously stirred at room temperature under a hydrogen atmosphere for 2 hours. After adding celite to the reaction solution and filtering, the filtrate was concentrated, and the residue was washed with diisopropyl ether to give the title compound having a melting point of 110 to 111 ° C.
1 g (100% yield) was obtained.

【０２９２】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.01 (1H, d, J=8.1Hz), 7.87 (1H,dd, J=7.7, 1.5H
z), 7.52-7.33 (2H, m), 6.81-6.71 (2H, m), 6.59 (1
H, d, J=8.4Hz), 5.39 (2H, s), 3.40 (2H, br.s), 2.1
4 (3H, s). （３）メチルＮ−［４−（ベンゾチアゾール−２−
イルメトキシ）−２−メチルフェニル］カルバマート
（化合物番号Ｃ１．５）（工程Ｂ−４）上記（２）の方法で製造された４−（ベンゾチアゾール
−２−イルメトキシ）−２−メチルアニリン５５．０ｇ
をＤＭＦ４００ｍｌに溶解後、氷水浴中ピリジン８２．
５ｍｌ、クロロ蟻酸メチル１８．９ｍｌを加え、２時間
撹拌した。反応溶液を水中に静かに加え、析出した結晶
を水洗後、さらにジエチルエーテルで洗浄した。得られ
た粗結晶を四塩化炭素−アセトン（４：１）で再結晶
し、融点１４７〜１４９℃を有する標記化合物３６．２
ｇ（収率５４％）を得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.01 (1H, d, J = 8.1Hz), 7.87 (1H, dd, J = 7.7, 1.5H
z), 7.52-7.33 (2H, m), 6.81-6.71 (2H, m), 6.59 (1
(H, d, J = 8.4Hz), 5.39 (2H, s), 3.40 (2H, br.s), 2.1
4 (3H, s). (3) Methyl N- [4- (benzothiazole-2-
Ylmethoxy) -2-methylphenyl] carbamate
(Compound No. C1.5) (Step B-4) 55.0 g of 4- (benzothiazol-2-ylmethoxy) -2-methylaniline produced by the method of the above (2).
Was dissolved in 400 ml of DMF, and then pyridine was dissolved in an ice water bath.
5 ml and 18.9 ml of methyl chloroformate were added, and the mixture was stirred for 2 hours. The reaction solution was gently added to water, and the precipitated crystals were washed with water and further washed with diethyl ether. The obtained crude crystals were recrystallized from carbon tetrachloride-acetone (4: 1) to give the title compound 36.2 having a melting point of 147 to 149 ° C.
g (54% yield).

【０２９３】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.03 (1H, d, J=7.3Hz), 7.90 (1H,dd, J=6.8, 0.8H
z), 7.55-7.36 (3H, m), 6.91-6.86 (2H, m), 6.21 (2
H, br.s), 5.46 (2H, s), 3.76 (3H, s), 2.24 (3H,
s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.03 (1H, d, J = 7.3Hz), 7.90 (1H, dd, J = 6.8, 0.8H
z), 7.55-7.36 (3H, m), 6.91-6.86 (2H, m), 6.21 (2
H, br.s), 5.46 (2H, s), 3.76 (3H, s), 2.24 (3H,
s).

【０２９４】[0294]

【実施例２２】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］カルバマート（化合物番
号Ｃ１．５）（工程Ａ−１）上記実施例１５（１）の方法で得たメチルＮ−（４−
ヒドロキシ−２−メチルフェニル）カルバマート１０．
０ｇを、ＤＭＦ３０ｍｌ及び水６ｍｌに溶かし、氷冷
下、水酸化カリウム３．６ｇの水溶液１０ｍｌを加え、
同温度で２０分間撹袢した。その後、同温度で、２−ク
ロロメチルベンゾチアゾール１０．０ｇのＤＭＦ溶液２
５ｍｌを加え、室温で１時間、６０℃で２時間撹袢し
た。反応終了後、反応混合物を水に注ぎ、結晶が析出し
た。結晶をろ取し、水、ジエチルエーテルで順に洗浄
後、酢酸エチルで再結晶することにより、標記化合物１
０．５ｇ（収率５９％）を１４７〜１４９℃の融点を有
する結晶として得た。ＮＭＲスペクトルは上記実施例２
１で得たものと一致した。Example 22: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] carbamate (compound number
No. C1.5) (Step A-1) Methyl N- (4-) obtained by the method of Example 15 (1) above.
9. (hydroxy-2-methylphenyl) carbamate
0 g was dissolved in DMF (30 ml) and water (6 ml), and an aqueous solution of potassium hydroxide (3.6 g) (10 ml) was added under ice-cooling.
The mixture was stirred at the same temperature for 20 minutes. Thereafter, at the same temperature, a solution of 10.0 g of 2-chloromethylbenzothiazole in DMF 2
5 ml was added, and the mixture was stirred at room temperature for 1 hour and at 60 ° C. for 2 hours. After the completion of the reaction, the reaction mixture was poured into water to precipitate crystals. The crystals were collected by filtration, washed sequentially with water and diethyl ether, and recrystallized from ethyl acetate to give the title compound 1
0.5 g (59% yield) were obtained as crystals having a melting point of 147-149 ° C. The NMR spectrum is shown in Example 2 above.
This was consistent with that obtained in 1.

【０２９５】[0295]

【実施例２３】Ｎ−［４−（ベンゾチアゾール−２−イルメチルチオ）
フェニル］アセトアミド（化合物番号Ａ１．３）（工程
Ａ−１）４−アセトアミドチオフェノール３０３．１ｍｇのＤＭ
Ｆ溶液６ｍｌに、６０％水素化ナトリウム７９．７ｍｇ
を、室温で加え、更に、２−ブロモメチルベンゾチアゾ
ール４５４．８ｍｇのジメチルホルムアミド溶液１ｍｌ
を加え、室温で２時間撹袢した。反応終了後、酢酸エチ
ルを加え、水で洗浄し、無水硫酸ナトリウムで乾燥し
た。ろ過後、減圧下に溶媒を留去し、得られた残さをシ
リカゲルカラムクロマトグラフィー（ヘキサン：酢酸エ
チル＝１：２）で精製することにより、標記化合物４６
２．７ｍｇ（収率８１％）を１４７〜１４９℃の融点を
有する固体として得た。ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.94 (1H, b
r.d, J=7.8Hz), 7.83 (1H, br.d, J=6.7Hz), 7.50-7.30
(6H, m), 7.14 (1H, br.s), 4.47 (2H, s), 2.15 (3H,
s).Example 23 N- [4- (benzothiazol-2-ylmethylthio)
Phenyl] acetamide (Compound No. A1.3) (Step A-1) 303.1 mg of 4-acetamidothiophenol DM
79.7 mg of 60% sodium hydride in 6 ml of F solution
At room temperature, and a solution of 454.8 mg of 2-bromomethylbenzothiazole in 1 ml of dimethylformamide
Was added and stirred at room temperature for 2 hours. After completion of the reaction, ethyl acetate was added, washed with water, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 1: 2) to give the title compound 46.
2.7 mg (81% yield) were obtained as a solid with a melting point of 147-149 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.94 (1H, b
rd, J = 7.8Hz), 7.83 (1H, br.d, J = 6.7Hz), 7.50-7.30
(6H, m), 7.14 (1H, br.s), 4.47 (2H, s), 2.15 (3H,
s).

【０２９６】[0296]

【実施例２４】メチルＮ−［４−（ベンゾチアゾール−２−イルメチ
ルチオ）フェニル］カルバマート（化合物番号Ａ１．
７）（１）メチルＮ−（４−メルカプトフェニル）カル
バマート（工程Ｂ−４）４−アミノチオフェノール２．４０ｇに、１０％水酸化
ナトリウム水溶液１７．４ｍｌを、室温で静かに加え、
更に、クロロ蟻酸メチル３．２７ｍｌを滴下して、室温
のまま２時間撹袢した。反応終了後、４Ｎ塩酸１．５ｍ
ｌを加えて、反応混合物を酸性にし、塩化メチレンで抽
出した。有機層を水で洗浄し、無水硫酸ナトリウムで乾
燥した。ろ過後、減圧下に溶媒を留去し、粗結晶を得
た。粗結晶に、メタノール４ｍｌ及びナトリウムメトキ
シドのメタノール溶液（２Ｍ）１０ｍｌを、室温で加
え、同温度で１時間３０分撹袢した。撹袢終了後、４Ｎ
塩酸２ｍｌを加えて、反応混合物を酸性にし、塩化メチ
レンで抽出した。有機層を水で洗浄し、無水硫酸ナトリ
ウムで乾燥した。ろ過後、減圧下に溶媒を留去し、得ら
れた粗結晶を塩化メチレン−ヘキサンの混合溶媒で再結
晶することにより、標記化合物１．１３５ｇ（収率３２
％）を９４〜９６℃の融点を有する固体として得た。Example 24 Methyl N- [4- (benzothiazol-2-ylmethyl)
Ruthio) phenyl] carbamate (Compound No. A1.
7) (1) Methyl N- (4-mercaptophenyl) car
Bamate (Step B-4) To 2.40 g of 4-aminothiophenol, 17.4 ml of a 10% aqueous sodium hydroxide solution was gently added at room temperature.
Further, 3.27 ml of methyl chloroformate was added dropwise, and the mixture was stirred at room temperature for 2 hours. After the reaction, 4N hydrochloric acid 1.5m
The reaction mixture was acidified by the addition of 1 and extracted with methylene chloride. The organic layer was washed with water and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain a crude crystal. 4 ml of methanol and 10 ml of a methanol solution of sodium methoxide (2M) were added to the crude crystals at room temperature, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. After stirring, 4N
The reaction mixture was acidified by adding 2 ml of hydrochloric acid and extracted with methylene chloride. The organic layer was washed with water and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the obtained crude crystals were recrystallized with a mixed solvent of methylene chloride-hexane to give 1.135 g of the title compound (yield 32).
%) As a solid with a melting point of 94-96 ° C.

【０２９７】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.27 (4H, s), 6.54 (1H, br.s), 3.77 (3H, s), 1.57
(1H, s). （２）メチルＮ−［４−（ベンゾチアゾール−２−
イルメチルチオ）フェニル］カルバマート（工程Ａ−
１）上記（１）の方法で得たメチルＮ−（４−メルカプト
フェニル）カルバマート４１８．５ｍｇをＤＭＦ８．４
ｍｌに溶かし、氷冷下、６０％水素化ナトリウム１０
０．５ｍｇを加え、同温度で１０分間撹袢した。更に、
同温度で２−ブロモメチルベンゾチアゾール５７３．１
ｍｇを加え、室温で３時間３０分撹袢した。反応終了
後、反応混合物に、飽和塩化アンモニウム水溶液を加
え、酢酸エチルで抽出した。有機層は、水で洗浄し、無
水硫酸ナトリウムで乾燥した。ろ過後、減圧下に溶媒を
留去し、得られた粗結晶をシリカゲルカラムクロマトグ
ラフィー（溶出溶媒ヘキサン：酢酸エチル＝４：１）
で精製することにより、標記化合物４６２．７ｍｇ（収
率８１％）を１３９〜１４１℃の融点を有する固体とし
て得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.27 (4H, s), 6.54 (1H, br.s), 3.77 (3H, s), 1.57
(1H, s). (2) Methyl N- [4- (benzothiazole-2-
Ylmethylthio) phenyl] carbamate (Step A-
1) 418.5 mg of methyl N- (4-mercaptophenyl) carbamate obtained by the method of the above (1) was added to DMF 8.4.
and 60% sodium hydride 10% under ice-cooling.
0.5 mg was added, and the mixture was stirred at the same temperature for 10 minutes. Furthermore,
At the same temperature, 2-bromomethylbenzothiazole 573.1
The mixture was stirred at room temperature for 3 hours and 30 minutes. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the resulting crude crystals were subjected to silica gel column chromatography (elution solvent: hexane: ethyl acetate = 4: 1).
To give 462.7 mg (yield 81%) of the title compound as a solid having a melting point of 139-141 ° C.

【０２９８】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.94 (1H, br.d, J=7.6Hz), 7.83 (1H, br.d, J=6.5H
z), 7.49-7.26 (6H, m), 6.56 (1H, br.s), 4.45 (2H,
s), 3.76 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.94 (1H, br.d, J = 7.6Hz), 7.83 (1H, br.d, J = 6.5H)
z), 7.49-7.26 (6H, m), 6.56 (1H, br.s), 4.45 (2H,
s), 3.76 (3H, s).

【０２９９】[0299]

【実施例２５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］−Ｎ−エトキシカルボニルアセトアミド（化合
物番号Ｂ２．６３）（工程Ｂ−５）上記実施例１の方法で得たＮ−［４−（ベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド１８７
ｍｇのＤＭＦ溶液４ｍｌに、氷冷下、６０％水素化ナト
リウム２８ｍｇを加え、同温度で５分間撹袢した。更
に、同温度でクロロ蟻酸エチル０．０６６ｍｌを加え、
室温で５時間撹袢した。反応終了後、反応混合物に、飽
和塩化アンモニウム水溶液を加え、酢酸エチルで抽出し
た。有機層は、水、飽和食塩水で、順に洗浄し、無水硫
酸ナトリウムで乾燥した。ろ過後、減圧下に溶媒を留去
し、得られた粗結晶をシリカゲルカラムクロマトグラフ
ィー（溶出溶媒ヘキサン：酢酸エチル＝１：１）で精
製することにより、標記化合物２５．６ｍｇ（収率８１
％）を１５５〜１６０℃の融点を有する固体として得
た。Example 25 N- [4- (benzothiazol-2-ylmethoxy) phenyl
Enyl] -N-ethoxycarbonylacetamide (compound
( Product number B2.63) (Step B-5) N- [4- (benzothiazol-2-ylmethoxy) phenyl] acetamide 187 obtained by the method of Example 1 above.
28 mg of 60% sodium hydride was added to 4 ml of the DMF solution under ice-cooling, and the mixture was stirred at the same temperature for 5 minutes. Further, 0.066 ml of ethyl chloroformate was added at the same temperature,
The mixture was stirred at room temperature for 5 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline in this order, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the obtained crude crystals were purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 1) to give 25.6 mg of the title compound (yield 81).
%) Was obtained as a solid with a melting point of 155-160 ° C.

【０３００】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.04 (1H, d, J=6.3Hz), 7.72 (1H,d, J=6.9Hz), 7.55
-7.26 (4H, m), 7.06 (2H, s), 5.50 (2H, s), 4.18 (2
H, q,J=6.6Hz), 2.60 (3H, s), 1.18 (3H, t, J=6.7H
z).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.04 (1H, d, J = 6.3Hz), 7.72 (1H, d, J = 6.9Hz), 7.55
-7.26 (4H, m), 7.06 (2H, s), 5.50 (2H, s), 4.18 (2
H, q, J = 6.6Hz), 2.60 (3H, s), 1.18 (3H, t, J = 6.7H
z).

【０３０１】[0301]

【実施例２６】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（３，３−ジメチ
ル−２−オキソブチル）カルバマート（化合物番号Ｄ
１．３５）（工程Ｂ−５）上記実施例２２の方法で得たＮ−［４−（ベンゾチアゾ
ール−２−イルメトキシ）−２−メチルフェニル］アセ
トアミドカルバマート１００ｍｇのＤＭＦ溶液３ｍｌ
に、氷冷下、６０％水素化ナトリウム１８ｍｇを加え、
同温度で３０分間撹袢した。更に、同温度で２−ブロモ
−３，３−ジメチル−２−ブタノン０．０６２ｍｌを加
え、室温で１時間撹袢した。反応終了後、反応混合物
に、水を加え、酢酸エチルで抽出した。有機層は、水、
飽和食塩水で、順に洗浄し、無水硫酸ナトリウムで乾燥
した。ろ過後、減圧下に溶媒を留去し、得られた残さを
分取薄層クロマトグラフィー（溶出溶媒ヘキサン：酢
酸エチル＝１：１）で精製することにより、標記化合物
９２ｍｇ（収率７１％）を油状物として得た。Example 26 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (3,3-dimethyl)
2-oxobutyl) carbamate (Compound No. D
1.35) (Step B-5) 3 ml of a DMF solution of 100 mg of N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] acetamidocarbamate obtained by the method of Example 22 above
, 18 mg of 60% sodium hydride was added thereto under ice cooling,
The mixture was stirred at the same temperature for 30 minutes. Further, at the same temperature, 0.062 ml of 2-bromo-3,3-dimethyl-2-butanone was added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer is water,
The extract was washed sequentially with saturated saline and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the obtained residue was purified by preparative thin-layer chromatography (elution solvent: hexane: ethyl acetate = 1: 1) to give the title compound (92 mg, yield 71%). Was obtained as an oil.

【０３０２】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.02 (1H, d, J=7.6Hz), 7.90 (1H,d, J=7.7Hz), 7.38
-7.54 (2H, m), 7.31 (1H, t, J=9.3Hz), 6.79-6.94 (2
H, m), 5.46 (2H, s), 3.64 (3H, s), 2.24 (3H, s),
1.18 (9H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.02 (1H, d, J = 7.6Hz), 7.90 (1H, d, J = 7.7Hz), 7.38
-7.54 (2H, m), 7.31 (1H, t, J = 9.3Hz), 6.79-6.94 (2
H, m), 5.46 (2H, s), 3.64 (3H, s), 2.24 (3H, s),
1.18 (9H, s).

【０３０３】[0303]

【実施例２７】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−プロピオニルオキ
シメチルカルバマート（化合物番号Ｄ１．７０）（工程
Ｂ−７）上記実施例１９の方法で得たＮ−［４−（ベンゾチアゾ
ール−２−イルメトキシ）−２−メチルフェニル］−Ｎ
−ヒドロキシメチルカルバマート１２１ｍｇの塩化メチ
レン溶液２ｍｌに、氷冷下、ピリジン０．１ｍｌ及び塩
化プロピオニル０．１ｍｌを加え、同温度で１０分間撹
袢した。反応終了後、反応混合物に、水を加え、塩化メ
チレンで抽出した。有機層は、水で洗浄し、無水硫酸ナ
トリウムで乾燥した。ろ過後、減圧下に溶媒を留去し、
得られた残さをシリカゲルカラムクロマトグラフィー
（溶出溶媒ヘキサン：酢酸エチル＝５：１）で精製す
ることにより、標記化合物１３３ｍｇ（収率９４％）を
油状物として得た。Example 27 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-propionyloxy
Cimethylcarbamate (Compound No. D1.70) (Step B-7) N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] -N obtained by the method of Example 19 above
To 2 ml of a methylene chloride solution of 121 mg of -hydroxymethyl carbamate were added 0.1 ml of pyridine and 0.1 ml of propionyl chloride under ice cooling, and the mixture was stirred at the same temperature for 10 minutes. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with methylene chloride. The organic layer was washed with water and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure,
The obtained residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 5: 1) to give 133 mg (yield 94%) of the title compound as an oil.

【０３０４】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.06-7.89 (2H, m), 7.55-7.37 (2H,m), 7.09 (1H, d,
J=8.0Hz), 6.93 (1H, d, J=2.8Hz), 6.86 (1H, dd, J=
8.6,2.8Hz), 5.56 (2H, Abq, J=10.2Hz, Dn=62.2Hz),
5.47 (2H, s), 3.81-3.65 (3H, m), 2.34 (2H, q, J=7.
6Hz), 2.20 (3H, s), 1.11 (3H, t, J=7.6Hz).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.06-7.89 (2H, m), 7.55-7.37 (2H, m), 7.09 (1H, d,
J = 8.0Hz), 6.93 (1H, d, J = 2.8Hz), 6.86 (1H, dd, J =
8.6,2.8Hz), 5.56 (2H, Abq, J = 10.2Hz, Dn = 62.2Hz),
5.47 (2H, s), 3.81-3.65 (3H, m), 2.34 (2H, q, J = 7.
6Hz), 2.20 (3H, s), 1.11 (3H, t, J = 7.6Hz).

【０３０５】[0305]

【実施例２８】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］カルバマート（化合物
番号Ｃ１．６）（１）２−ブロモメチルベンゾオキサゾール（工程Ｃ
−１）２−メチルベンゾオキサゾール５６ｍｌ及びＮ−ブロモ
スクシンイミド１８．７３ｇを四塩化炭素２０ｍｌに加
え、更に室温で過酸化ベンゾイル５０９．８ｍｇを加え
て、６時間加熱還流した。反応終了後、ろ過し、減圧下
に溶媒を留去し、粗結晶を得た。粗結晶を酢酸エチルに
溶かし、飽和亜硫酸ナトリウム水溶液、水、飽和食塩水
で、順に洗浄し、無水硫酸ナトリウムで乾燥した。ろ過
後、減圧下に溶媒を留去し、得られた残さをシリカゲル
カラムクロマトグラフィー（溶出溶媒ヘキサン：酢酸
エチル＝１０：１）で精製することにより、標記化合物
３．３４ｇ（収率３７％）を油状物として得た。Example 28: Methyl N- [4- (benzoxazol-2-ylmeth)
Toxi) -2-methylphenyl] carbamate (compound
No. C1.6) (1) 2-bromomethylbenzoxazole (Step C
-1) 56 ml of 2-methylbenzoxazole and 18.73 g of N-bromosuccinimide were added to 20 ml of carbon tetrachloride, and 509.8 mg of benzoyl peroxide was further added at room temperature, followed by heating under reflux for 6 hours. After completion of the reaction, the mixture was filtered and the solvent was distilled off under reduced pressure to obtain a crude crystal. The crude crystals were dissolved in ethyl acetate, washed sequentially with a saturated aqueous solution of sodium sulfite, water and saturated saline, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 10: 1) to give 3.34 g (yield 37%) of the title compound. Was obtained as an oil.

【０３０６】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.79-7.68 (2H, m), 7.58-7.50 (2H,m), 7.46-7.30 (4
H, m), 4.60 (2H, s). （２）メチルＮ−［４−（ベンゾオキサゾール−２
−イルメトキシ）−２−メチルフェニル］カルバマート
（工程Ａ−１）上記実施例１５（１）の方法で得たメチルＮ−（４−
ヒドロキシ−２−メチルフェニル）カルバマート２００
ｍｇをＤＭＦ５ｍｌに溶かし、氷冷下、６０％水素化ナ
トリウム５２．８ｍｇを加え、同温度で５分間撹袢し
た。更に、同温度で、上記（１）の方法で得た２−ブロ
モメチルベンゾオキサゾール３０５．４ｍｇを加え、室
温で２０分間、５０℃で１時間撹袢した。反応終了後、
反応混合物に、飽和塩化アンモニウム水溶液を加え、酢
酸エチルで抽出した。有機層は、水、飽和食塩水で、順
に洗浄し、無水硫酸ナトリウムで乾燥した。ろ過後、減
圧下に溶媒を留去し、得られた粗結晶をシリカゲルカラ
ムクロマトグラフィー（溶出溶媒ヘキサン：酢酸エチ
ル＝２：１）で精製することにより、標記化合物３２
０．４ｍｇ（収率８５．５％）を１５９〜１６２℃の融
点を有する固体として得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.79-7.68 (2H, m), 7.58-7.50 (2H, m), 7.46-7.30 (4
H, m), 4.60 (2H, s). (2) Methyl N- [4- (benzoxazole-2
-Ylmethoxy) -2-methylphenyl] carbamate (Step A-1) Methyl N- (4-
(Hydroxy-2-methylphenyl) carbamate 200
mg was dissolved in 5 ml of DMF, and 52.8 mg of 60% sodium hydride was added under ice-cooling, followed by stirring at the same temperature for 5 minutes. Furthermore, 305.4 mg of 2-bromomethylbenzoxazole obtained by the method (1) was added at the same temperature, and the mixture was stirred at room temperature for 20 minutes and at 50 ° C. for 1 hour. After the reaction,
A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline in this order, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the resulting crude crystals were purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 2: 1) to give the title compound 32.
0.4 mg (85.5% yield) was obtained as a solid with a melting point of 159-162 ° C.

【０３０７】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.78-7.73 (1H, m), 7.61-7.51 (1H,m), 7.41-7.32 (3
H, m), 6.93-6.88 (2H, m), 6.22 (1H, br.s), 5.30 (2
H, s), 3.76 (3H, s), 2.24 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.78-7.73 (1H, m), 7.61-7.51 (1H, m), 7.41-7.32 (3
H, m), 6.93-6.88 (2H, m), 6.22 (1H, br.s), 5.30 (2
H, s), 3.76 (3H, s), 2.24 (3H, s).

【０３０８】[0308]

【実施例２９】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］アセトアミド（化合物番号Ｃ１．
１）（１）２−ブロモメチルベンゾチアゾール（工程Ｃ−
１）２−メチルベンゾチアゾール５．８７ｇ及びＮ−ブロモ
スクシンイミド１５．４ｇを四塩化炭素６０ｍｌに加
え、更に室温で過酸化ベンゾイル４７６ｍｇを加えて、
９時間加熱還流した。反応終了後、ろ過し、減圧下に溶
媒を留去し、粗結晶を得た。得られた粗結晶をシリカゲ
ルカラムクロマトグラフィー（溶出溶媒ヘキサン：酢酸
エチル＝１０：１）で精製することにより、標記化合物
６．１０ｇ（収率６８％）を４３〜４５℃の融点を有す
る固体として得た。 Working Example 29 N- [4- (Benzothiazol-2-ylmethoxy)-
2-Methylphenyl] acetamide (Compound No. C1.
1) (1) 2-bromomethylbenzothiazole (Step C-
1) 5.87 g of 2-methylbenzothiazole and 15.4 g of N-bromosuccinimide were added to 60 ml of carbon tetrachloride, and 476 mg of benzoyl peroxide was further added at room temperature.
The mixture was refluxed for 9 hours. After completion of the reaction, the mixture was filtered and the solvent was distilled off under reduced pressure to obtain a crude crystal. The obtained crude crystals were purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 10: 1) to give 6.10 g (yield 68%) of the title compound as a solid having a melting point of 43-45 ° C. Obtained.

【０３０９】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.03 (1H, d, J=7.6Hz), 7.89 (1H,dd, J=6.8, 1.1H
z), 7.56-7.39 (2H, m), 4.82 (2H, s). （２）Ｎ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］アセトアミド（工程Ａ−
１）４−アセトアミド−３−メチルフェノール９７．７ｍｇ
をＤＭＦ３ｍｌに溶かし、氷冷下、６０％水素化ナトリ
ウム２３．３ｍｇを加え、同温度で３分間撹袢した。更
に、同温度で、上記（２）の方法で得た２−ブロモメチ
ルベンゾチアゾール１３２．２ｍｇを加え、室温で３時
間撹袢した。反応終了後、反応混合物に、飽和塩化アン
モニウム水溶液を加え、酢酸エチルで抽出した。有機層
は、水、飽和食塩水で、順に洗浄し、無水硫酸ナトリウ
ムで乾燥した。ろ過後、減圧下に溶媒を留去し、得られ
た残さを塩化メチレン−ヘキサン混合溶媒で再結晶する
ことにより、標記化合物８５．７ｍｇ（収率８２％）を
１７９〜１８２℃の融点を有する固体として得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.03 (1H, d, J = 7.6Hz), 7.89 (1H, dd, J = 6.8, 1.1H
z), 7.56-7.39 (2H, m), 4.82 (2H, s). (2) N- [4- (benzothiazol-2-ylmethoate)
[Xy) -2-methylphenyl] acetamide (Step A-
1) 97.7 mg of 4-acetamido-3-methylphenol
Was dissolved in 3 ml of DMF, 23.3 mg of 60% sodium hydride was added under ice cooling, and the mixture was stirred at the same temperature for 3 minutes. Further, at the same temperature, 132.2 mg of 2-bromomethylbenzothiazole obtained by the above method (2) was added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline in this order, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the obtained residue was recrystallized from a methylene chloride-hexane mixed solvent to give 85.7 mg (yield 82%) of the title compound having a melting point of 179 to 182 ° C. Obtained as a solid.

【０３１０】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.05-7.85 (2H, m), 7.55-7.28 (3H,m), 5.46 (2H,
s), 2.24 (3H, s), 2.19 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.05-7.85 (2H, m), 7.55-7.28 (3H, m), 5.46 (2H, m
s), 2.24 (3H, s), 2.19 (3H, s).

【０３１１】[0311]

【実施例３０】Ｎ−［４−（ベンゾオキサゾール−２−
イルメトキシ）−２−メチルフェニル］アセトアミド
（化合物番号Ｃ１．２）（工程Ａ−１）４−アセトアミド−３−メチルフェノール２００．０ｍ
ｇをＤＭＦ１０ｍｌに溶かし、氷冷下、６０％水素化ナ
トリウム５３．２ｍｇを加え、同温度で５分間撹袢し
た。更に、同温度で、上記実施例２８（１）の方法で得
た２−ブロモメチルベンゾオキサゾール３０７．９ｍｇ
を加え、室温で３０分間、５０℃で１時間３０分撹袢し
た。反応終了後、反応混合物に、飽和塩化アンモニウム
水溶液を加え、酢酸エチルで抽出した。有機層は、水、
飽和食塩水で、順に洗浄し、無水硫酸ナトリウムで乾燥
した。ろ過後、減圧下に溶媒を留去し、得られた粗結晶
をシリカゲルカラムクロマトグラフィー（溶出溶媒ヘ
キサン：酢酸エチル＝１：３）で精製することにより、
標記化合物２１８．５ｍｇ（収率６１％）を１６０℃の
融点を有する固体として得た。Working Example 30 N- [4- (benzoxazole-2-
Ylmethoxy) -2-methylphenyl] acetamide
(Compound No. C1.2) (Step A-1) 4-acetamido-3-methylphenol 200.0 m
g was dissolved in 10 ml of DMF, and 53.2 mg of 60% sodium hydride was added under ice-cooling, followed by stirring at the same temperature for 5 minutes. Further, at the same temperature, 307.9 mg of 2-bromomethylbenzoxazole obtained by the method of Example 28 (1) above.
Was added and the mixture was stirred at room temperature for 30 minutes and at 50 ° C. for 1 hour 30 minutes. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer is water,
The extract was washed sequentially with saturated saline and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the resulting crude crystals were purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 1: 3) to give
218.5 mg (61% yield) of the title compound were obtained as a solid having a melting point of 160.degree.

【０３１２】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.78-7.74 (1H, m), 7.58-7.51 (2H,m), 7.39-7.34 (1
H, m), 6.92-6.84 (3H, m), 5.30 (2H, s), 2.24 (3H,
s), 2.18 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.78-7.74 (1H, m), 7.58-7.51 (2H, m), 7.39-7.34 (1
H, m), 6.92-6.84 (3H, m), 5.30 (2H, s), 2.24 (3H,
s), 2.18 (3H, s).

【０３１３】[0313]

【実施例３１】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２−
クロロプロピオンアミド（化合物番号Ｄ２．４０）（工
程Ｂ−５）上記実施例２２の方法で得たＮ−［４−（ベンゾチアゾ
ール−２−イルメトキシ）−２−メチルフェニル］アセ
トアミドカルバマート１００ｍｇのＤＭＦ溶液４ｍｌ
に、氷冷下、６０％水素化ナトリウム１８ｍｇを加え、
同温度で１５分間撹袢した。更に、同温度で２−クロロ
プロピオン酸クロライド０．０５９ｍｌを加え、室温で
３時間撹袢した。反応終了後、反応混合物に、水を加
え、酢酸エチルで抽出した。有機層は、水、飽和食塩水
で、順に洗浄し、無水硫酸ナトリウムで乾燥した。ろ過
後、減圧下に溶媒を留去し、得られた残さを分取薄層ク
ロマトグラフィー（ヘキサン：酢酸エチル＝１：１）で
精製することにより、標記化合物７０ｍｇ（収率５４
％）を油状物として得た。Example 31 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2-
Chloropropionamide (Compound No. D2.40) (Step B-5) DMF of 100 mg of N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] acetamidocarbamate obtained by the method of Example 22 above 4 ml of solution
, 18 mg of 60% sodium hydride was added thereto under ice cooling,
The mixture was stirred at the same temperature for 15 minutes. Further, 0.059 ml of 2-chloropropionic chloride was added at the same temperature, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline in this order, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the obtained residue was purified by preparative thin-layer chromatography (hexane: ethyl acetate = 1: 1) to give 70 mg of the title compound (yield 54).
%) As an oil.

【０３１４】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
8.04 (1H, d, J=7.3Hz), 7.92 (1H,d, J=7.5Hz), 7.34
-7.56 (2H, m), 6.84-7.07 (3H, m), 5.73 (1H, dq, J
d =1.4Hz, J q =6.7Hz), 5.48 (2H, s), 3.75 (3
H, s), 2.16 (s) + 2.10 (s)(3H), 1.74 (d, J=6.7Hz)
+ 1.73 (d, J=6.7Hz) (3H).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
8.04 (1H, d, J = 7.3Hz), 7.92 (1H, d, J = 7.5Hz), 7.34
-7.56 (2H, m), 6.84-7.07 (3H, m), 5.73 (1H, dq, J
d = 1.4Hz, J q = 6.7Hz), 5.48 (2H, s), 3.75 (3
H, s), 2.16 (s) + 2.10 (s) (3H), 1.74 (d, J = 6.7Hz)
+ 1.73 (d, J = 6.7Hz) (3H).

【０３１５】[0315]

【実施例３２】メチルＮ−［４−（６−メトキシベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト（化合物番号Ｇ１．３９）（工程Ａ−１）上記実施例１５（１）で得られたメチルＮ−（４−ヒ
ドロキシ−２−メチルフェニル）カルバマート８２ｍｇ
をＤＭＦ５ｍｌに溶かし、氷冷下、６０％水素化ナトリ
ウム２３ｍｇを加え、同温度で１５分間撹袢した。更
に、同温度で、上記実施例６（１）の方法で得た２−ブ
ロモメチル−６−メトキシベンゾチアゾール１５０ｍｇ
を加え、室温で６時間撹袢した。反応終了後、反応混合
物に、飽和塩化アンモニウム水溶液を加え、酢酸エチル
で抽出した。有機層は、水で洗浄し、無水硫酸ナトリウ
ムで乾燥した。ろ過後、減圧下に溶媒を留去し、得られ
た残さをシリカゲルカラムクロマトグラフィー（溶出溶
媒ヘキサン：酢酸エチル＝２：１）で精製することに
より、標記化合物１１０ｍｇ（収率６８％）を１２３〜
１２５℃の融点を有する固体として得た。Example 32: Methyl N- [4- (6-methoxybenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamer
(Compound No. G1.39) (Step A-1) 82 mg of methyl N- (4-hydroxy-2-methylphenyl) carbamate obtained in Example 15 (1) above
Was dissolved in 5 ml of DMF, 23 mg of 60% sodium hydride was added under ice cooling, and the mixture was stirred at the same temperature for 15 minutes. Further, at the same temperature, 150 mg of 2-bromomethyl-6-methoxybenzothiazole obtained by the method of Example 6 (1) above.
Was added and stirred at room temperature for 6 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 2: 1) to obtain 110 mg of the title compound (yield 68%). ~
Obtained as a solid with a melting point of 125 ° C.

【０３１６】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.90 (1H, d, J=8.9Hz), 7.52 (1H,br.s), 7.33 (1H,
d, J=2.5Hz), 7.09(1H, dd, J=8.9, 2.5Hz), 6.90-6.86
(2H,m), 6.20-6.19 (1H, br.m), 5.41 (2H, s), 3.88
(3H, s), 3.76 (3H, s), 2.23 (3H, s).NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.90 (1H, d, J = 8.9Hz), 7.52 (1H, br.s), 7.33 (1H,
d, J = 2.5Hz), 7.09 (1H, dd, J = 8.9, 2.5Hz), 6.90-6.86
(2H, m), 6.20-6.19 (1H, br.m), 5.41 (2H, s), 3.88
(3H, s), 3.76 (3H, s), 2.23 (3H, s).

【０３１７】[0317]

【実施例３３】メチルＮ−［４−（５−フルオロベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト（化合物番号Ｇ１．５７）（１）２−ブロモメチル−５−フルオロベンゾチアゾ
ール（工程Ｃ−１）２−メチル−５−フルオロベンゾチアゾール８．７９ｇ
及びＮ−ブロモスクシンイミド２０．６ｇを四塩化炭素
８８ｍｌに加え、更に室温で過酸化ベンゾイル１２７ｍ
ｇを加えて、６時間加熱還流した。反応終了後、ろ過
し、減圧下に溶媒を留去し、粗結晶を得た。得られた粗
結晶をシリカゲルカラムクロマトグラフィー（溶出溶媒
ヘキサン：酢酸エチル＝１０：１）で精製することに
より、標記化合物８５０ｍｇ（収率７％）を固体として
得た。Working Example 33 Methyl N- [4- (5-fluorobenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamer
(Compound No. G1.57) (1) 2-bromomethyl-5-fluorobenzothiazo
Lumpur (Step C-1) 2-methyl-5-fluoro-benzothiazole 8.79g
And 20.6 g of N-bromosuccinimide were added to 88 ml of carbon tetrachloride.
g was added and the mixture was heated under reflux for 6 hours. After completion of the reaction, the mixture was filtered and the solvent was distilled off under reduced pressure to obtain a crude crystal. The obtained crude crystals were purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 10: 1) to give 850 mg (yield 7%) of the title compound as a solid.

【０３１８】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.81 (1H, dd, J=8.9, 5.1Hz), 7.70(1H, dd, J=9.3,
2.4Hz), 7.26-7.16 (1H, m), 4.80 (2H, s). （２）メチルＮ−［４−（５−フルオロベンゾチア
ゾール−２−イルメトキシ）−２−メチルフェニル］カ
ルバマート（工程Ａ−１）上記の実施例１５（１）の方法で得たＮ−（４−ヒドロ
キシ−２−メチルフェニル）カルバマート２０４．９ｍ
ｇをＤＭＦ５ｍｌに溶かし、氷冷下、６０％水素化ナト
リウム５４．６ｍｇを加え、同温度で５分間撹袢した。
更に、同温度で、上記（１）の方法で得た２−ブロモメ
チル−５−フルオロベンゾチアゾール３６６．２ｍｇを
加え、室温で１時間３０分撹袢した。反応終了後、反応
混合物に、飽和塩化アンモニウム水溶液を加え、酢酸エ
チルで抽出した。有機層は、水、飽和食塩水で、順に洗
浄し、無水硫酸ナトリウムで乾燥した。ろ過後、減圧下
に溶媒を留去し、得られた粗結晶をシリカゲルカラムク
ロマトグラフィー（溶出溶媒ヘキサン：酢酸エチル＝
３：１）で精製することにより、標記化合物２６３．３
ｍｇ（収率６５％）を１６５〜１６８℃の融点を有する
固体として得た。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.81 (1H, dd, J = 8.9, 5.1Hz), 7.70 (1H, dd, J = 9.3,
2.4Hz), 7.26-7.16 (1H, m), 4.80 (2H, s). (2) Methyl N- [4- (5-fluorobenzothia
Zol-2-ylmethoxy) -2-methylphenyl] ca
Rubamate (Step A-1) N- (4-hydroxy-2-methylphenyl) carbamate 204.9m obtained by the method of Example 15 (1) above.
g was dissolved in 5 ml of DMF, and 54.6 mg of 60% sodium hydride was added under ice-cooling, followed by stirring at the same temperature for 5 minutes.
Further, at the same temperature, 366.2 mg of 2-bromomethyl-5-fluorobenzothiazole obtained by the method (1) was added, and the mixture was stirred at room temperature for 1 hour and 30 minutes. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline in this order, and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the resulting crude crystals were subjected to silica gel column chromatography (elution solvent: hexane: ethyl acetate =
3: 1) to give the title compound 263.3.
mg (65% yield) was obtained as a solid with a melting point of 165-168 ° C.

【０３１９】ＮＭＲスペクトル(200MHz,CDCl₃), δppm:
7.82 (1H, dd, J=8.8, 5.1Hz), 7.70(1H, dd, J=9.4,
2.4Hz), 7.60-7.50 (1H, br.s), 7.18 (1H, td, J=8.8,
2.4Hz), 6.90-6.84 (2H, m), 6.22 (1H, br.s), 5.43
(2H, s), 3.76 (3H, s). 上記、実施例１乃至３３の方法に準じて、以下の実施例
３４乃至４５５に示す化合物を製造した。NMR spectrum (200 MHz, CDCl ₃ ), δ ppm:
7.82 (1H, dd, J = 8.8, 5.1Hz), 7.70 (1H, dd, J = 9.4,
2.4Hz), 7.60-7.50 (1H, br.s), 7.18 (1H, td, J = 8.8,
2.4Hz), 6.90-6.84 (2H, m), 6.22 (1H, br.s), 5.43
(2H, s), 3.76 (3H, s). The compounds shown in the following Examples 34 to 455 were produced according to the methods of Examples 1 to 33 described above.

【０３２０】実施例３４乃至８６に示す化合物は、実施
例１の方法に準じて製造した。The compounds shown in Examples 34 to 86 were produced according to the method of Example 1.

【０３２１】実施例８７乃至９０に示す化合物は、実施
例２の方法に準じて製造した。The compounds shown in Examples 87 to 90 were produced according to the method of Example 2.

【０３２２】実施例９１乃至１１２に示す化合物は、実
施例３の方法に準じて製造した。The compounds shown in Examples 91 to 112 were produced according to the method of Example 3.

【０３２３】実施例１１３乃至１４７に示す化合物は、
実施例４の方法に準じて製造した。The compounds shown in Examples 113 to 147 were
Manufactured according to the method of Example 4.

【０３２４】実施例１４８乃至１９８に示す化合物は、
実施例５の方法に準じて製造した。The compounds shown in Examples 148 to 198 were
Manufactured according to the method of Example 5.

【０３２５】実施例１９９乃至２２１に示す化合物は、
実施例６の方法に準じて製造した。The compounds shown in Examples 199 to 221 were
It was manufactured according to the method of Example 6.

【０３２６】実施例２２２乃至２５５及び４５５に示す
化合物は、実施例１０の方法に準じて製造した。The compounds shown in Examples 222 to 255 and 455 were produced according to the method of Example 10.

【０３２７】実施例２５６乃至２６７に示す化合物は、
実施例１１の方法に準じて製造した。The compounds shown in Examples 256 to 267 were
Manufactured according to the method of Example 11.

【０３２８】実施例２６８乃至２７９に示す化合物は、
実施例１２の方法に準じて製造した。The compounds shown in Examples 268 to 279 were
Produced according to the method of Example 12.

【０３２９】実施例２８０乃至３３１に示す化合物は、
実施例１３の方法に準じて製造した。The compounds shown in Examples 280 to 331 were
Manufactured according to the method of Example 13.

【０３３０】実施例３３２乃至３６３に示す化合物は、
実施例１５の方法に準じて製造した。The compounds shown in Examples 332 to 363 were
Produced according to the method of Example 15.

【０３３１】実施例３６４及び３６５に示す化合物は、
実施例１６の方法に準じて製造した。The compounds shown in Examples 364 and 365 were
Manufactured according to the method of Example 16.

【０３３２】実施例３６６及び４０５に示す化合物は、
実施例１７の方法に準じて製造した。The compounds shown in Examples 366 and 405 were
Manufactured according to the method of Example 17.

【０３３３】実施例４０６に示す化合物は、実施例１８
の方法に準じて製造した。The compound shown in Example 406 was prepared according to Example 18
It was manufactured according to the method described in above.

【０３３４】実施例４０７に示す化合物は、実施例１９
の方法に準じて製造した。The compound shown in Example 407 was prepared in Example 19
It was manufactured according to the method described in above.

【０３３５】実施例４０８及び４５２に示す化合物は、
実施例２０の方法に準じて製造した。The compounds shown in Examples 408 and 452 are
Produced according to the method of Example 20.

【０３３６】実施例４５３及び４５４に示す化合物は、
実施例２６の方法に準じて製造した。The compounds shown in Examples 453 and 454 are as follows:
Manufactured according to the method of Example 26.

【０３３７】[0337]

【実施例３４】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
フェニル］アセトアミド（化合物番号A1.2）融点：146 −148 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.73
(1H, m); 7.59-7.48 (1H,m); 7.48-7.25 (4H, m); 7.19
-6.95 (3H, m); 5.31 (2H, s); 2.16 (3H, s).Example 34 N- [4- (benzoxazol-2-ylmethoxy)
Phenyl] acetamide (Compound No. A1.2) Melting point: 146-148 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.73
(1H, m); 7.59-7.48 (1H, m); 7.48-7.25 (4H, m); 7.19
-6.95 (3H, m); 5.31 (2H, s); 2.16 (3H, s).

【０３３８】[0338]

【実施例３５】Ｓ−メチルＮ−［４−（ベンゾチアゾール−２−イル
メトキシ）フェニル］チオカルバマート（化合物番号A
1.13 ）融点：162 −164 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H, d
d, J=8.7 & 1.0 Hz); 7.93-7.88 (1H, m); 7.51-7.33
(4H, m); 7.03-6.96 (3H, m); 5.47 (2H, s); 2.41 (3
H, s). Working Example 35 S-methyl N- [4- (benzothiazol-2-yl)
Methoxy) phenyl] thiocarbamate (Compound No. A
1.13) Melting point: 162-164 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.03 (1H, d
d, J = 8.7 & 1.0 Hz); 7.93-7.88 (1H, m); 7.51-7.33
(4H, m); 7.03-6.96 (3H, m); 5.47 (2H, s); 2.41 (3
H, s).

【０３３９】[0339]

【実施例３６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−メトキシフェニル］アセトアミド（化合物番号C8.1
9 ）融点：108 −113 ℃ ＮＭＲスペクトル(270MHz,CDCl₃), δppm: 8.01 (1H,
d, J=7.7 Hz); 7.89 (1H,d, J=7.7 Hz); 7.52-7.32 (2
H, m); 6.92 (1H, d, J=8.6 Hz); 6.74 (1H, dd,J=2.5
& 8.6 Hz); 5.50 (2H, s); 3.89 (3H, s); 2.14 (3H,
s). Working Example 36 N- [4- (benzothiazol-2-ylmethoxy)-
3-methoxyphenyl] acetamide (Compound No. C8.1
9) Melting point: 108-113 ° C NMR spectrum (270MHz, CDCl ₃ ), δppm: 8.01 (1H,
d, J = 7.7 Hz); 7.89 (1H, d, J = 7.7 Hz); 7.52-7.32 (2
H, m); 6.92 (1H, d, J = 8.6 Hz); 6.74 (1H, dd, J = 2.5
& 8.6 Hz); 5.50 (2H, s); 3.89 (3H, s); 2.14 (3H, s)
s).

【０３４０】[0340]

【実施例３７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−トリフルオロメチルフェニル］アセトアミド（化合
物番号C10.1 ）融点：178 ℃ ＮＭＲスペクトル(200MHz,CDCl₃+CD₃OD), δppm: 7.97
(1H, dd, J=8.7 & 1.3 Hz); 7.86 (1H, dd, J=7.9 & 1.
3 Hz); 7.69 (1H, d, J=9.2 Hz); 7.51-7.14 (4H, m);
5.44 (2H, s); 2.12 (3H, s). Working Example 37 N- [4- (Benzothiazol-2-ylmethoxy)-
2-trifluoromethylphenyl] acetamide (compound
Article No. C10.1) Melting point: 178 ° C NMR spectrum (200 MHz, CDCl ₃ + CD ₃ OD), δppm: 7.97
(1H, dd, J = 8.7 & 1.3 Hz); 7.86 (1H, dd, J = 7.9 & 1.
3 Hz); 7.69 (1H, d, J = 9.2 Hz); 7.51-7.14 (4H, m);
5.44 (2H, s); 2.12 (3H, s).

【０３４１】[0341]

【実施例３８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−ニトロフェニル］アセトアミド（化合物番号C10.4
6）融点：191 −193 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 10.09 (1H,
br.s); 8.70 (1H, d, J=9.3 Hz); 8.08-8.04 (1H, m);
7.94-7.86 (2H, m); 7.57-7.35 (3H, m); 5.53 (2H,
s); 2.27 (3H, s). Working Example 38 N- [4- (Benzothiazol-2-ylmethoxy)-
2-nitrophenyl] acetamide (compound number C10.4
6) Melting point: 191-193 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 10.09 (1H,
br.s); 8.70 (1H, d, J = 9.3 Hz); 8.08-8.04 (1H, m);
7.94-7.86 (2H, m); 7.57-7.35 (3H, m); 5.53 (2H, m
s); 2.27 (3H, s).

【０３４２】[0342]

【実施例３９】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−ニトロフェニル］アセトアミド（化合物番号C10.6
2）融点：188 −190 ℃ ＮＭＲスペクトル(270MHz,CDCl₃), δｐｐｍ：９．２
２（１Ｈ，ｂｒ．ｓ）；８．１５（１Ｈ，
ｄ，Ｊ＝２．７Ｈｚ）；８．０３（１Ｈ，
ｄ，Ｊ＝９．０Ｈｚ）；７．９４（１Ｈ，
ｄ，Ｊ＝９．０Ｈｚ）；７．９３（１Ｈ，ｄ
ｄ，Ｊ＝２．７＆９．０Ｈｚ）；７．５７−
７．３７（２Ｈ，ｍ）；７．１４（１Ｈ，
ｄ，Ｊ＝９．０Ｈｚ）；５．５９（２Ｈ，
ｓ）；２．１５（３Ｈ，ｓ）． Working Example 39 N- [4- (Benzothiazol-2-ylmethoxy)-
3-nitrophenyl] acetamide (Compound No. C10.6
2) Melting point: 188-190 ° C NMR spectrum (270 MHz, CDCl ₃ ), δ ppm: 9.2
8. (1H, br.s);
d, J = 2.7 Hz); 8.03 (1H,
d, J = 9.0 Hz); 7.94 (1H,
d, J = 9.0 Hz); 7.93 (1H, d
d, J = 2.7 & 9.0 Hz); 7.57-
7.37 (2H, m); 7.14 (1H,
d, J = 9.0 Hz); 5.59 (2H,
s); 2.15 (3H, s).

【０３４３】[0343]

【実施例４０】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−エトキシカルボニルフェニル］アセトアミド（化合
物番号Ｃ１０．８２）融点：140 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 10.84 (1H,
br.s); 8.65 (1H, d, J=9.3 Hz); 8.02 (1H, dd, J=8.5
& 1.0 Hz); 7.89 (1H, dd, J=7.9 & 1.9 Hz); 7.68 (1
H, d, J=3.1 Hz); 7.54-7.36 (2H, m); 7.24 (2H, dd,
J=9.3 & 3.1 Hz);5.48 (2H, s); 4.36 (2H, q, J=7.1 H
z); 2.20 (3H, s); 1.40 (3H, t, J=7.1Hz). Working Example 40 N- [4- (benzothiazol-2-ylmethoxy)-
2-ethoxycarbonylphenyl] acetamide (compound
Article No. C10.82) Melting point: 140 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 10.84 (1H
br.s); 8.65 (1H, d, J = 9.3 Hz); 8.02 (1H, dd, J = 8.5
& 1.0 Hz); 7.89 (1H, dd, J = 7.9 & 1.9 Hz); 7.68 (1
H, d, J = 3.1 Hz); 7.54-7.36 (2H, m); 7.24 (2H, dd,
J = 9.3 & 3.1 Hz); 5.48 (2H, s); 4.36 (2H, q, J = 7.1 H
z); 2.20 (3H, s); 1.40 (3H, t, J = 7.1Hz).

【０３４４】[0344]

【実施例４１】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−プロポキシカルボニルフェニル］アセトアミド（化
合物番号C10.84）融点：127 −128 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 10.86 (1H,
br.s); 8.66 (1H, d, J=9.2 Hz); 8.03 (1H, d, J=7.8
Hz); 7.90 (1H, dd, J=7.3 & 1.4 Hz); 7.68 (1H, d, J
=3.1 Hz); 7.55-7.40 (2H, m); 7.25 (1H, dd, J=9.2 &
3.1 Hz); 5.49 (2H, s); 4.27 (2H, t, J=6.6 Hz); 2.
21 (3H, s); 1.79 (2H, sextet, J=7.1 Hz); 1.02 (3H,
t, J=7.4 Hz). Working Example 41 N- [4- (benzothiazol-2-ylmethoxy)-
2-propoxycarbonylphenyl] acetamide
Compound No. C10.84) Melting point: 127-128 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 10.86 (1H,
br.s); 8.66 (1H, d, J = 9.2 Hz); 8.03 (1H, d, J = 7.8
Hz); 7.90 (1H, dd, J = 7.3 & 1.4 Hz); 7.68 (1H, d, J
= 3.1 Hz); 7.55-7.40 (2H, m); 7.25 (1H, dd, J = 9.2 &
3.1 Hz); 5.49 (2H, s); 4.27 (2H, t, J = 6.6 Hz); 2.
21 (3H, s); 1.79 (2H, sextet, J = 7.1 Hz); 1.02 (3H,
t, J = 7.4 Hz).

【０３４５】[0345]

【実施例４２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−イソプロポキシカルボニルフェニル］アセトアミド
（化合物番号C10.86）融点：127 −128 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 10.89 (1H,
br.s); 8.65 (1H, d, J=9.3 Hz); 8.03 (1H, d, J=7.1
Hz); 7.90 (1H, dd, J=7.2 & 1.1 Hz); 7.67 (1H, d, J
=3.1 Hz); 7.54-7.40 (2H, m); 7.24 (1H, dd, J=9.3 &
3.1 Hz); 5.48 (2H, s); 5.22 (1H, heptet, J=6.3 H
z); 2.20 (3H, s); 1.38 (6H, d, J=6.3 Hz). Working Example 42 N- [4- (benzothiazol-2-ylmethoxy)-
2-Isopropoxycarbonylphenyl] acetamide
(Compound No. C10.86) Melting point: 127-128 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 10.89 (1H,
br.s); 8.65 (1H, d, J = 9.3 Hz); 8.03 (1H, d, J = 7.1
Hz); 7.90 (1H, dd, J = 7.2 & 1.1 Hz); 7.67 (1H, d, J
= 3.1 Hz); 7.54-7.40 (2H, m); 7.24 (1H, dd, J = 9.3 &
3.1 Hz); 5.48 (2H, s); 5.22 (1H, heptet, J = 6.3 H
z); 2.20 (3H, s); 1.38 (6H, d, J = 6.3 Hz).

【０３４６】[0346]

【実施例４３】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−メトキシカルボニルフェニル］アセトアミド（化合
物番号C10.88）融点：167 −168 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.02 (1H,
d, J=8.5 Hz); 7.94-7.75(3H, m); 7.55-7.37 (2H, m);
7.06 (1H, d, J=8.9 Hz); 5.53 (2H, s); 3.96(3H,
s); 2.17 (3H, s).Example 43 N- [4- (benzothiazol-2-ylmethoxy)-
3-methoxycarbonylphenyl] acetamide (compound
Compound No. C10.88) Melting point: 167-168 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.02 (1H,
d, J = 8.5 Hz); 7.94-7.75 (3H, m); 7.55-7.37 (2H, m);
7.06 (1H, d, J = 8.9 Hz); 5.53 (2H, s); 3.96 (3H,
s); 2.17 (3H, s).

【０３４７】[0347]

【実施例４４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−エトキシカルボニルフェニル］アセトアミド（化合
物番号C10.92）融点：164 −165 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.96-7.72
(4H, m); 7.45-7.35 (3H,m); 7.00 (1H, d, J=9.0 Hz);
5.45 (2H, s); 4.35 (2H, q, J=7.0 Hz); 2.06(3H,
s); 1.33 (3H, t, J=7.0 Hz).Example 44 N- [4- (benzothiazol-2-ylmethoxy)-
3-ethoxycarbonylphenyl] acetamide (compound
Compound No. C10.92) Melting point: 164-165 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 7.96-7.72
(4H, m); 7.45-7.35 (3H, m); 7.00 (1H, d, J = 9.0 Hz);
5.45 (2H, s); 4.35 (2H, q, J = 7.0 Hz); 2.06 (3H, s)
s); 1.33 (3H, t, J = 7.0 Hz).

【０３４８】[0348]

【実施例４５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−プロポキシカルボニルフェニル］アセトアミド（化
合物番号C10.94）融点：129 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.00 (1H,
d, J=8.2 Hz); 7.91-7.70(4H, m); 7.52-7.34 (2H, m);
7.00 (1H, d, J=9.0 Hz); 5.49 (2H, s); 4.28(2H, t,
J=6.7 Hz); 2.13 (3H, s); 1.76 (2H, sextet, J=7.1
Hz); 0.97 (3H,t, J=7.4 Hz). Working Example 45 N- [4- (Benzothiazol-2-ylmethoxy)-
3-propoxycarbonylphenyl] acetamide
Compound No. C10.94) Melting point: 129 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.00 (1H,
d, J = 8.2 Hz); 7.91-7.70 (4H, m); 7.52-7.34 (2H, m);
7.00 (1H, d, J = 9.0 Hz); 5.49 (2H, s); 4.28 (2H, t,
J = 6.7 Hz); 2.13 (3H, s); 1.76 (2H, sextet, J = 7.1
Hz); 0.97 (3H, t, J = 7.4 Hz).

【０３４９】[0349]

【実施例４６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−イソプロポキシカルボニルフェニル］アセトアミド
（化合物番号C10.96）融点：153.5 −155 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H, d
d, J=8.1 & 1.5 Hz); 7.92 (1H, dd, J=7.7 & 1.0 Hz);
7.82-7.77 (2H, m); 7.55-7.37 (2H, m); 7.18(1H, b
r.s); 7.06 (1H, d, J=9.9 Hz); 5.53 (2H, s); 5.30
(1H, heptet, J=6.3 Hz); 2.17 (3H, s); 1.38 (6H, d,
J=6.3 Hz). Working Example 46 N- [4- (Benzothiazol-2-ylmethoxy)-
3-Isopropoxycarbonylphenyl] acetamide
(Compound No. C10.96) Melting point: 153.5-155 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H, d
d, J = 8.1 & 1.5 Hz); 7.92 (1H, dd, J = 7.7 & 1.0 Hz);
7.82-7.77 (2H, m); 7.55-7.37 (2H, m); 7.18 (1H, b
rs); 7.06 (1H, d, J = 9.9 Hz); 5.53 (2H, s); 5.30
(1H, heptet, J = 6.3 Hz); 2.17 (3H, s); 1.38 (6H, d,
J = 6.3 Hz).

【０３５０】[0350]

【実施例４７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−ホルミルフェニル］アセトアミド（化合物番号C10.
98）融点：174 −176 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 10.89 (1H,
s); 9.87 (1H, s); 8.71(1H, d, J=10.3 Hz); 8.04 (1
H, dd, J=8.2 & 1.3 Hz); 7.91 (1H, dd, J=7.6& 1.5 H
z); 7.56-7.31 (4H, m); 5.54 (2H, s); 2.23 (3H, s). Working Example 47 N- [4- (benzothiazol-2-ylmethoxy)-
2-formylphenyl] acetamide (compound number C10.
98) Melting point: 174-176 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 10.89 (1H,
s); 9.87 (1H, s); 8.71 (1H, d, J = 10.3 Hz); 8.04 (1
H, dd, J = 8.2 & 1.3 Hz); 7.91 (1H, dd, J = 7.6 & 1.5 H
z); 7.56-7.31 (4H, m); 5.54 (2H, s); 2.23 (3H, s).

【０３５１】[0351]

【実施例４８】Ｎ−｛４−［１−( ベンゾチアゾール−２−イル）エト
キシ］−２−メチルフェニル｝アセトアミド（化合物番
号E1.15 ）融点：57−60℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.00 (1H,
d, J=7.7 Hz); 7.85 (1H,d, J=7.7 Hz); 7.30-7.51 (2
H, m); 7.05 (1H, br.s); 6.76-6.92 (2H, m); 5.68 (1
H, q, J=6.5 Hz); 2.15 (3H, s); 2.11 (3H, s); 1.81
(3H, s).Working Example 48 N- {4- [1- (benzothiazol-2-yl) ethoate
[Xy] -2-methylphenyl} acetamide (compound number
No. E1.15) Melting point: 57-60 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.00 (1H,
d, J = 7.7 Hz); 7.85 (1H, d, J = 7.7 Hz); 7.30-7.51 (2
H, m); 7.05 (1H, br.s); 6.76-6.92 (2H, m); 5.68 (1
H, q, J = 6.5 Hz); 2.15 (3H, s); 2.11 (3H, s); 1.81
(3H, s).

【０３５２】[0352]

【実施例４９】Ｎ−｛４−［１−( ベンゾチアゾール−２−イル）プロ
ポキシ］フェニル｝アセトアミド（化合物番号E6.1）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.01 (1H,
d, J=8.2 Hz); 7.85 (1H,d, J=7.7 Hz); 7.25-7.52 (4
H, m); 6.94 (2H, d, J=9.1 Hz); 5.46 (1H, t, J=6.2
Hz); 2.10-2.24 (2H, m); 2.10 (3H, s); 1.11 (3H, t,
J=7.4 Hz).Example 49 N- {4- [1- (benzothiazol-2-yl) pro]
[Poxy] phenyl} acetamide (Compound No. E6.1) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.01 (1H,
d, J = 8.2 Hz); 7.85 (1H, d, J = 7.7 Hz); 7.25-7.52 (4
H, m); 6.94 (2H, d, J = 9.1 Hz); 5.46 (1H, t, J = 6.2
Hz); 2.10-2.24 (2H, m); 2.10 (3H, s); 1.11 (3H, t,
J = 7.4 Hz).

【０３５３】[0353]

【実施例５０】Ｎ−｛４−［１−( ベンゾチアゾール−２−イル）プロ
ポキシ］−２−メチルフェニル｝アセトアミド（化合物
番号E7.5）ガム状ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.02 (1H,
d, J=8.1 Hz); 7.86 (1H,d, J=7.9 Hz); 7.31-7.51 (3
H, m); 6.78-6.99 (3H, m); 5.47 (1H, t, J=5.8Hz);
2.10-2.23 (2H, m); 2.16 (3H, s); 2.13 (3H, s); 1.1
0 (3H, t, J=7.3 Hz).Example 50 N- {4- [1- (benzothiazol-2-yl) pro]
POXY] -2-methylphenyl} acetamide (compound
No. E7.5) gummy NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.02 (1H,
d, J = 8.1 Hz); 7.86 (1H, d, J = 7.9 Hz); 7.31-7.51 (3
H, m); 6.78-6.99 (3H, m); 5.47 (1H, t, J = 5.8Hz);
2.10-2.23 (2H, m); 2.16 (3H, s); 2.13 (3H, s); 1.1
0 (3H, t, J = 7.3 Hz).

【０３５４】[0354]

【実施例５１】Ｎ−｛４−［１−( ベンゾチアゾール−２−イル）−２
−メチルプロポキシ］フェニル｝アセトアミド（化合物
番号E7.131）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.02 (1H,
d, J=8.1 Hz); 7.85 (1H,d, J=7.6 Hz); 7.28-7.51 (4
H, m); 6.91 (2H, d, J=9.0 Hz); 5.24 (1H, d, J=6.4
Hz); 2.39 (1H, heptet, J=6.7 Hz); 2.08 (3H, s); 1.
16 (3H, d, J=6.7Hz); 1.04 (3H, d, J=6.7 Hz).Working Example 51 N- {4- [1- (benzothiazol-2-yl) -2]
-Methylpropoxy] phenyl} acetamide (compound
No.E7.131) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.02 (1H,
d, J = 8.1 Hz); 7.85 (1H, d, J = 7.6 Hz); 7.28-7.51 (4
H, m); 6.91 (2H, d, J = 9.0 Hz); 5.24 (1H, d, J = 6.4
Hz); 2.39 (1H, heptet, J = 6.7 Hz); 2.08 (3H, s); 1.
16 (3H, d, J = 6.7 Hz); 1.04 (3H, d, J = 6.7 Hz).

【０３５５】[0355]

【実施例５２】Ｎ−｛４−［１−( ベンゾチアゾール−２−イル）−２
−メチルプロポキシ］−２−メチルフェニル｝アセトア
ミド（化合物番号E7.135）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
２（１Ｈ，ｄ，Ｊ＝８．４Ｈｚ）；７．８５
（１Ｈ，ｄ，Ｊ＝７．５Ｈｚ）；７．３１−
７．５５（３Ｈ，ｍ）；６．７８−６．９０
（３Ｈ，ｍ）；５．２６（１Ｈ，ｄ，Ｊ＝
６．３Ｈｚ）；２．３９（１Ｈ，ｈｅｐｔｅｔ，
Ｊ＝６．８Ｈｚ）；２．１６（３Ｈ，ｓ）；
２．１４（３Ｈ，ｓ）；１．１６（３Ｈ，
ｄ，Ｊ＝６．８Ｈｚ）；１．０４（３Ｈ，
ｄ，Ｊ＝６．８Ｈｚ）．Working Example 52 N- {4- [1- (benzothiazol-2-yl) -2]
-Methylpropoxy] -2-methylphenyl} acetoa
Mide (Compound No. E7.135) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
2. (1H, d, J = 8.4 Hz); 7.85
(1H, d, J = 7.5 Hz);
7.55 (3H, m); 6.78-6.90
(3H, m); 5.26 (1H, d, J =
6.3 Hz); 2.39 (1H, heptet,
J = 6.8 Hz); 2.16 (3H, s);
2.14 (3H, s); 1.16 (3H, s)
d, J = 6.8 Hz); 1.04 (3H,
d, J = 6.8 Hz).

【０３５６】[0356]

【実施例５３】Ｎ−［４−（４−メチルベンゾチアゾール−２−イルメ
トキシ）フェニル］アセトアミド（化合物番号Ｆ１．
１）融点：154 −156 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.72 (1H,
t, J=4.7 Hz); 7.45-7.40(2H, m); 7.29 (2H, d, J=5.2
9 Hz); 7.05-6.98 (3H, m); 5.48 (2H, s); 2.76(3H,
s); 2.16 (3H, s).Example 53 N- [4- (4-methylbenzothiazol-2-ylmethine)
Toxy) phenyl] acetamide (Compound No. F1.
1) Melting point: 154-156 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 7.72 (1H,
t, J = 4.7 Hz); 7.45-7.40 (2H, m); 7.29 (2H, d, J = 5.2
9 Hz); 7.05-6.98 (3H, m); 5.48 (2H, s); 2.76 (3H,
s); 2.16 (3H, s).

【０３５７】[0357]

【実施例５４】Ｎ−［４−（６−メチルベンゾチアゾール−２−イルメ
トキシ）フェニル］アセトアミド（化合物番号F1.21 ）融点：201 −202 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.90 (1H,
d, J=8.3 Hz); 7.68 (1H,s); 7.43-7.39 (2H, m); 7.34
-7.28 (1H, m); 7.10 (1H, br.s); 7.01-6.97 (2H, m);
5.44 (2H, s); 2.49 (3H, s); 2.15 (3H, s).Example 54 N- [4- (6-Methylbenzothiazol-2-ylmethine)
Toxi) phenyl] acetamide (Compound No. F1.21) Melting point: 201-202 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.90 (1H,
d, J = 8.3 Hz); 7.68 (1H, s); 7.43-7.39 (2H, m); 7.34
-7.28 (1H, m); 7.10 (1H, br.s); 7.01-6.97 (2H, m);
5.44 (2H, s); 2.49 (3H, s); 2.15 (3H, s).

【０３５８】[0358]

【実施例５５】Ｎ−［４−（４−メトキシベンゾチアゾール−２−イル
メトキシ）フェニル］アセトアミド（化合物番号F3.1）融点：147 −148 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.49-7.31
(4H, m); 7.07-6.90 (4H,m); 5.49 (2H, s); 4.67 (3H,
s); 2.15 (3H, s).Example 55 N- [4- (4-methoxybenzothiazol-2-yl)
Methoxy) phenyl] acetamide (Compound No. F3.1) Melting point: 147-148 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.49-7.31
(4H, m); 7.07-6.90 (4H, m); 5.49 (2H, s); 4.67 (3H,
s); 2.15 (3H, s).

【０３５９】[0359]

【実施例５６】Ｎ−［４−（５−メトキシベンゾチアゾール−２−イル
メトキシ）フェニル］アセトアミド（化合物番号F3.10
）融点：217 −219 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.73 (1H,
d, J=8.8 Hz); 7.51 (1H,d, J=2.2 Hz); 7.44-7.40 (2
H, m); 7.08-6.97 (4H, m); 5.44 (2H, s); 3.90(3H,
s); 2.15 (3H, s).Working Example 56 N- [4- (5-methoxybenzothiazol-2-yl)
Methoxy) phenyl] acetamide (Compound No.F3.10
) Melting point: 217-219 ° C NMR spectrum (200MHz, CDCl ₃ ), δ ppm: 7.73 (1H,
d, J = 8.8 Hz); 7.51 (1H, d, J = 2.2 Hz); 7.44-7.40 (2
H, m); 7.08-6.97 (4H, m); 5.44 (2H, s); 3.90 (3H,
s); 2.15 (3H, s).

【０３６０】[0360]

【実施例５７】Ｎ−［４−（７−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］アセトアミド（化合物番号F4.40
）融点：149 −152 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.83 (1H,
d, J=8.1 Hz); 7.48-7.41(3H, m); 7.17-7.08 (2H, m);
7.02-6.97 (2H, m); 5.46 (2H, s); 2.16 (3H,s).Example 57 N- [4- (7-fluorobenzothiazol-2-yl)
Methoxy) phenyl] acetamide (Compound No. F4.40
) Melting point: 149-152 ° C NMR spectrum (200MHz, CDCl ₃ ), δ ppm: 7.83 (1H,
d, J = 8.1 Hz); 7.48-7.41 (3H, m); 7.17-7.08 (2H, m);
7.02-6.97 (2H, m); 5.46 (2H, s); 2.16 (3H, s).

【０３６１】[0361]

【実施例５８】Ｎ−［４−（４−メトキシカルボニルベンゾオキサゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号F6.11 ）融点：158 −160 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=7.9 Hz); 7.79 (1H,dd, J=1.0 & 8.1 Hz); 7.31-
7.49 (4H, m); 6.98 (2H, d, J=8.9 Hz); 5.36 (2H,
s); 4.03 (3H, s); 2.14 (3H, s).Working Example 58 N- [4- (4-methoxycarbonylbenzoxazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Article number F6.11) Melting point: 158-160 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.05 (1H,
d, J = 7.9 Hz); 7.79 (1H, dd, J = 1.0 & 8.1 Hz); 7.31-
7.49 (4H, m); 6.98 (2H, d, J = 8.9 Hz); 5.36 (2H,
s); 4.03 (3H, s); 2.14 (3H, s).

【０３６２】[0362]

【実施例５９】メチルＮ−［４−（４−メトキシカルボニルベンゾオ
キサゾール−２−イルメトキシ）フェニル］カルバマー
ト（化合物番号F6.12 ）ガム状ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.8 Hz); 7.76 (1H,d, J=8.2 Hz); 7.44 (1H, t,
J=8.0 Hz); 7.23-7.37 (3H, m); 7.00 (2H, d, J=8.9 H
z); 6.61 (1H, br.s); 5.36 (2H, s); 4.03 (3H, s);
3.75 (3H, s).Working Example 59 Methyl N- [4- (4-methoxycarbonylbenzoo)
Xazol-2-ylmethoxy) phenyl] carbamer
(Compound No.F6.12) gum-like NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.04 (1H,
d, J = 7.8 Hz); 7.76 (1H, d, J = 8.2 Hz); 7.44 (1H, t,
J = 8.0 Hz); 7.23-7.37 (3H, m); 7.00 (2H, d, J = 8.9 H
z); 6.61 (1H, br.s); 5.36 (2H, s); 4.03 (3H, s);
3.75 (3H, s).

【０３６３】[0363]

【実施例６０】Ｎ−［４−（５−メトキシカルボニルベンゾオキサゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号F6.15 ）融点：165 −168 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.45 (1H,
s); 8.14 (1H, dd, J=1.7& 8.5 Hz); 7.60 (1H, d, J=
8.5 Hz); 7.43 (2H, d, J=9.0 Hz); 7.13 (1H, br.s);
7.02 (2H, d, J=9.0 Hz); 5.32 (2H, s); 3.96 (3H,
s); 2.16 (3H, s).Working Example 60 N- [4- (5-methoxycarbonylbenzoxazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product number F6.15) Melting point: 165-168 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.45 (1H,
s); 8.14 (1H, dd, J = 1.7 & 8.5 Hz); 7.60 (1H, d, J =
8.5 Hz); 7.43 (2H, d, J = 9.0 Hz); 7.13 (1H, br.s);
7.02 (2H, d, J = 9.0 Hz); 5.32 (2H, s); 3.96 (3H,
s); 2.16 (3H, s).

【０３６４】[0364]

【実施例６１】メチルＮ−［４−（５−メトキシカルボニルベンゾオ
キサゾール−２−イルメトキシ）フェニル］カルバマー
ト（化合物番号F6.16 ）融点：163 −167 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.45 (1H,
d, J=1.6 Hz); 8.13 (1H,dd, J=1.6 & 8.6 Hz); 7.59
(1H, d, J=8.6 Hz); 7.31 (2H, d, J=9.0 Hz); 7.02 (2
H, d, J=9.0 Hz); 6.51 (1H, br.s); 5.31 (2H, s); 3.
96 (3H, s); 3.76(3H, s).Working Example 61 Methyl N- [4- (5-methoxycarbonylbenzoo)
Xazol-2-ylmethoxy) phenyl] carbamer
(Compound number F6.16) melting point: 163-167 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.45 (1H,
d, J = 1.6 Hz); 8.13 (1H, dd, J = 1.6 & 8.6 Hz); 7.59
(1H, d, J = 8.6 Hz); 7.31 (2H, d, J = 9.0 Hz); 7.02 (2
(H, d, J = 9.0 Hz); 6.51 (1H, br.s); 5.31 (2H, s); 3.
96 (3H, s); 3.76 (3H, s).

【０３６５】[0365]

【実施例６２】Ｎ−［４−（６−メトキシカルボニルベンゾオキサゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号F6.19 ）融点：155 −158 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.24 (1H,
d, J=1.6 Hz); 8.09 (1H,dd, J=1.6 & 8.4 Hz); 7.78
(1H, d, J=8.4 Hz); 7.43 (2H, d, J=9.3 Hz); 7.01 (2
H, d, J=9.3 Hz); 5.32 (2H, s); 3.96 (3H, s); 2.05
(3H, s).Example 62 N- [4- (6-Methoxycarbonylbenzoxazo)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product number F6.19) Melting point: 155-158 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.24 (1H,
d, J = 1.6 Hz); 8.09 (1H, dd, J = 1.6 & 8.4 Hz); 7.78
(1H, d, J = 8.4 Hz); 7.43 (2H, d, J = 9.3 Hz); 7.01 (2
(H, d, J = 9.3 Hz); 5.32 (2H, s); 3.96 (3H, s); 2.05
(3H, s).

【０３６６】[0366]

【実施例６３】メチルＮ−［４−（６−メトキシカルボニルベンゾオ
キサゾール−２−イルメトキシ）フェニル］カルバマー
ト（化合物番号F6.20 ）融点：約230 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.25 (1H,
d, J=0.8 Hz); 8.09 (1H,dd, J=0.8 & 8.4 Hz); 7.78
(1H, d, J=8.4 Hz); 7.32 (2H, d, J=9.2 Hz); 7.01 (2
H, d, J=9.2 Hz); 6.50 (1H, br.s); 5.33 (2H, s); 3.
97 (3H, s); 3.76(3H, s).Example 63 Methyl N- [4- (6-methoxycarbonylbenzoo)
Xazol-2-ylmethoxy) phenyl] carbamer
(Compound No. F6.20) Melting point: about 230 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.25 (1H,
d, J = 0.8 Hz); 8.09 (1H, dd, J = 0.8 & 8.4 Hz); 7.78
(1H, d, J = 8.4 Hz); 7.32 (2H, d, J = 9.2 Hz); 7.01 (2
(H, d, J = 9.2 Hz); 6.50 (1H, br.s); 5.33 (2H, s); 3.
97 (3H, s); 3.76 (3H, s).

【０３６７】[0367]

【実施例６４】Ｎ−［４−（７−メトキシカルボニルベンゾオキサゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号F6.23 ）融点：102 −105 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.02 (1H,
d, J=7.8 Hz); 7.95 (1H,d, J=7.8 Hz); 7.46-7.39 (4
H, m); 7.01 (2H, d, J=8.8 Hz); 5.34 (2H, s);4.01
(3H, s); 2.14 (3H, s).Example 64 N- [4- (7-methoxycarbonylbenzoxazoline)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Article No. F6.23) Melting point: 102-105 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.02 (1H,
d, J = 7.8 Hz); 7.95 (1H, d, J = 7.8 Hz); 7.46-7.39 (4
H, m); 7.01 (2H, d, J = 8.8 Hz); 5.34 (2H, s); 4.01
(3H, s); 2.14 (3H, s).

【０３６８】[0368]

【実施例６５】メチルＮ−［４−（７−メトキシカルボニルベンゾオ
キサゾール−２−イルメトキシ）フェニル］カルバマー
ト（化合物番号F6.24 ）融点：142 −146 ℃ ＮＭＲスペクトル(200MHz,CDCl₃+CD₃OD), δppm: 7.96
(1H, dd, J=7.8 & 1.1 Hz); 7.88 (1H, dd, J=8.0 & 1.
1 Hz); 7.42-7.25 (3H, m); 6.95 (2H, d, J=9.1Hz);
5.28 (2H, s); 3.95 (3H, s); 3.67 (3H, s).Working Example 65 Methyl N- [4- (7-methoxycarbonylbenzoic)
Xazol-2-ylmethoxy) phenyl] carbamer
(Compound No. F6.24) Melting point: 142-146 ° C NMR spectrum (200 MHz, CDCl ₃ + CD ₃ OD), δ ppm: 7.96
(1H, dd, J = 7.8 & 1.1 Hz); 7.88 (1H, dd, J = 8.0 & 1.
1 Hz); 7.42-7.25 (3H, m); 6.95 (2H, d, J = 9.1Hz);
5.28 (2H, s); 3.95 (3H, s); 3.67 (3H, s).

【０３６９】[0369]

【実施例６６】Ｎ−［２−メチル−４−（４−メチルベンゾオキサゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号G1.4）融点：160 −161 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.56-7.51
(1H, m); 7.40-7.36 (1H,m); 7.29-7.22 (1H, m); 7.17
-7.13 (1H, m); 6.92-6.82 (3H, m); 5.29 (2H,s); 2.6
3 (3H, s); 2.24 (3H, s); 2.18 (3H, d, J=2.5 Hz).Working Example 66 N- [2-Methyl-4- (4-methylbenzoxazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product No. G1.4) Melting point: 160-161 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.56-7.51
(1H, m); 7.40-7.36 (1H, m); 7.29-7.22 (1H, m); 7.17
-7.13 (1H, m); 6.92-6.82 (3H, m); 5.29 (2H, s); 2.6
3 (3H, s); 2.24 (3H, s); 2.18 (3H, d, J = 2.5 Hz).

【０３７０】[0370]

【実施例６７】Ｎ−［２−メチル−４−（５−メチルベンゾオキサゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号G1.9）融点：177 −180 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.55-7.51
(2H, m); 7.42 (1H, d, J=7.9 Hz); 7.19-7.15 (1H,
m); 6.91-6.87 (3H, m); 5.27 (2H, s); 2.47 (3H,s);
2.23 (3H, s); 2.18 (3H, s).Working Example 67 N- [2-Methyl-4- (5-methylbenzoxazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product No. G1.9) Melting point: 177-180 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.55-7.51
(2H, m); 7.42 (1H, d, J = 7.9 Hz); 7.19-7.15 (1H,
m); 6.91-6.87 (3H, m); 5.27 (2H, s); 2.47 (3H, s);
2.23 (3H, s); 2.18 (3H, s).

【０３７１】[0371]

【実施例６８】Ｎ−［２−メチル−４−（６−メチルベンゾオキサゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号G1.14 ）融点：185 −188 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.61 (1H,
d, J=8.2 Hz); 7.55-7.50(1H, m); 7.35 (1H, s); 7.19
-7.14 (1H, m); 6.91-6.82 (3H, m); 5.30 (2H,s); 2.4
9 (3H, s); 2.23 (3H, s); 2.18 (3H, s).Working Example 68 N- [2-Methyl-4- (6-methylbenzoxazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Compound No. G1.14) Melting point: 185-188 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 7.61 (1H,
d, J = 8.2 Hz); 7.55-7.50 (1H, m); 7.35 (1H, s); 7.19
-7.14 (1H, m); 6.91-6.82 (3H, m); 5.30 (2H, s); 2.4
9 (3H, s); 2.23 (3H, s); 2.18 (3H, s).

【０３７２】[0372]

【実施例６９】Ｎ−［２−メチル−４−（７−メチルベンゾオキサゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号G1.19 ）融点：170 −173 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.60-7.51
(2H, m); 7.29-7.14 (2H,m); 6.95-6.89 (2H, m); 6.85
-6.59 (1H, br.m); 5.29 (2H, s); 2.54 (3H, s); 2.19
(3H, s).Working Example 69 N- [2-Methyl-4- (7-methylbenzoxazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Article No. G1.19) Melting point: 170-173 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.60-7.51
(2H, m); 7.29-7.14 (2H, m); 6.95-6.89 (2H, m); 6.85
-6.59 (1H, br.m); 5.29 (2H, s); 2.54 (3H, s); 2.19
(3H, s).

【０３７３】[0373]

【実施例７０】Ｎ−［４−（５−フルオロベンゾオキサゾール−２−イ
ルメトキシ）−２−メチルフェニル］アセトアミド（化
合物番号G1.58 ）融点：183 −185 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．５
３−７．４６（３Ｈ，ｍ）；７．１５−７．０５
（１Ｈ，ｍ）；６．９１−６．８９（３Ｈ，
ｍ）；５．２８（２Ｈ，ｓ）；２．２４（３
Ｈ，ｓ）；２．１９（３Ｈ，ｓ）．Working Example 70 N- [4- (5-Fluorobenzoxazol-2-i
Rumethoxy) -2-methylphenyl] acetamide
Compound No. G1.58) Melting point: 183-185 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.5
3-7.46 (3H, m); 7.15-7.05
(1H, m); 6.91-6.89 (3H,
m); 5.28 (2H, s); 2.24 (3
H, s); 2.19 (3H, s).

【０３７４】[0374]

【実施例７１】Ｎ−［４−（６−フルオロベンゾオキサゾール−２−イ
ルメトキシ）−２−メチルフェニル］アセトアミド（化
合物番号Ｇ１．６３）融点：178 −179 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.72-7.65
(1H, m); 7.57-7.52 (1H,m); 7.31-7.24 (1H, m); 6.91
-6.81 (3H, m); 5.27 (2H, s); 2.24 (3H, s); 2.19 (3
H, s).Working Example 71 N- [4- (6-Fluorobenzoxazol-2-i
Rumethoxy) -2-methylphenyl] acetamide
Compound No. G1.63) Melting point: 178-179 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.72-7.65
(1H, m); 7.57-7.52 (1H, m); 7.31-7.24 (1H, m); 6.91
-6.81 (3H, m); 5.27 (2H, s); 2.24 (3H, s); 2.19 (3
H, s).

【０３７５】[0375]

【実施例７２】Ｎ−［４−（７−フルオロベンゾオキサゾール−２−イ
ルメトキシ）−２−メチルフェニル］アセトアミド（化
合物番号G1.68 ）融点：173 −175 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.55 (2H,
d, J=7.1 Hz); 7.33-7.25(1H, m); 7.13 (1H, d, J=9.2
Hz); 6.92-6.82 (3H, m); 5.31 (2H, s); 2.24(3H,
s); 2.19 (3H, s).Working Example 72 N- [4- (7-Fluorobenzoxazol-2-i
Rumethoxy) -2-methylphenyl] acetamide
Compound No. G1.68) Melting point: 173-175 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.55 (2H,
d, J = 7.1 Hz); 7.33-7.25 (1H, m); 7.13 (1H, d, J = 9.2
Hz); 6.92-6.82 (3H, m); 5.31 (2H, s); 2.24 (3H,
s); 2.19 (3H, s).

【０３７６】[0376]

【実施例７３】Ｎ−［４−（５−クロロベンゾオキサゾール−２−イル
メトキシ）−２−メチルフェニル］アセトアミド（化合
物番号G1.76 ）融点：207 −209 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.74 (1H,
d, J=1.9 Hz); 7.56-7.46(2H, m); 7.35 (1H, dd, J=8.
8 & 1.8 Hz); 6.90-6.81 (3H, m); 5.28 (2H, s); 2.24
(3H, s); 2.19 (3H, s).Working Example 73 N- [4- (5-Chlorobenzoxazol-2-yl)
Methoxy) -2-methylphenyl] acetamide (compound
Compound No. G1.76) Melting point: 207-209 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.74 (1H,
d, J = 1.9 Hz); 7.56-7.46 (2H, m); 7.35 (1H, dd, J = 8.
8 & 1.8 Hz); 6.90-6.81 (3H, m); 5.28 (2H, s); 2.24
(3H, s); 2.19 (3H, s).

【０３７７】[0377]

【実施例７４】Ｎ−［２−メチル−４−（５−トリフルオロメチルベン
ゾオキサゾール−２−イルメトキシ）フェニル］アセト
アミド（化合物番号G1.95 ）融点：216 −218 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
s); 7.67 (2H, d, J=1.2Hz); 7.58-7.53 (1H, m); 6.91
-6.81(3H, m); 5.33 (2H, m); 2.25 (3H, s); 2.19 (3
H, s).Example 74 N- [2-methyl-4- (5-trifluoromethylben
Zoxazol-2-ylmethoxy) phenyl] aceto
Amide (Compound No. G1.95) Melting point: 216-218 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
s); 7.67 (2H, d, J = 1.2Hz); 7.58-7.53 (1H, m); 6.91
-6.81 (3H, m); 5.33 (2H, m); 2.25 (3H, s); 2.19 (3
H, s).

【０３７８】[0378]

【実施例７５】Ｎ−［２−メチル−４−（５−ニトロベンゾオキサゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号G1.109）融点：212 −216 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.65 (1H,
d, J=2.5 Hz); 8.39-8.33(1H, m); 7.68 (1H, d, J=8.8
Hz); 7.58-7.53 (1H, m); 6.95-6.81 (3H, m);5.34 (2
H, s); 2.24 (3H, s); 2.19 (3H, s).Working Example 75 N- [2-Methyl-4- (5-nitrobenzoxazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Compound No. G1.109) Melting point: 212-216 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.65 (1H,
d, J = 2.5 Hz); 8.39-8.33 (1H, m); 7.68 (1H, d, J = 8.8
Hz); 7.58-7.53 (1H, m); 6.95-6.81 (3H, m); 5.34 (2
H, s); 2.24 (3H, s); 2.19 (3H, s).

【０３７９】[0379]

【実施例７６】Ｎ−［４−（４−メトキシカルボニルベンゾオキサゾー
ル−２−イルメトキシ）−２−メチルフェニル］アセト
アミド（化合物番号G1.113）ガム状ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=7.7 Hz); 7.76 (1H,dd, J=1.0 & 8.2 Hz); 7.47
(2H, q, J=8.0 Hz); 6.81-6.95 (3H, m); 5.36 (2H,
s); 4.04 (3H, s); 2.23 (3H, s); 2.18 (3H, s).Working Example 76 N- [4- (4-methoxycarbonylbenzoxazole)
Ru-2-ylmethoxy) -2-methylphenyl] aceto
Amide (Compound No.G1.113) gum NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
d, J = 7.7 Hz); 7.76 (1H, dd, J = 1.0 & 8.2 Hz); 7.47
(2H, q, J = 8.0 Hz); 6.81-6.95 (3H, m); 5.36 (2H,
s); 4.04 (3H, s); 2.23 (3H, s); 2.18 (3H, s).

【０３８０】[0380]

【実施例７７】メチルＮ−［４−（４−メトキシカルボニルベンゾオ
キサゾール−２−イルメトキシ）−２−メチルフェニ
ル］カルバマート（化合物番号G1.114）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
５（１Ｈ，ｄｄ，Ｊ＝１．０＆７．７Ｈ
ｚ）；７．７７（１Ｈ，ｄｄ，Ｊ＝１．０＆
８．３Ｈｚ）；７．５２（１Ｈ，ｂｒ．
ｓ）；７．４５（１Ｈ，ｔ，Ｊ＝７．８Ｈ
ｚ）；６．８６−６．９４（２Ｈ，ｍ）；６．
２１（１Ｈ，ｂｒ．ｓ）；５．３７（２Ｈ，
ｓ）；４．０４（３Ｈ，ｓ）；３．７６（３
Ｈ，ｓ）；２．２３（３Ｈ，ｓ）．Working Example 77 Methyl N- [4- (4-methoxycarbonylbenzoo)
Xazol-2-ylmethoxy) -2-methylpheni
] Carbamate (Compound No. G1.114) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
5 (1H, dd, J = 1.0 & 7.7 H
z); 7.77 (1H, dd, J = 1.0 &
7.53); 7.52 (1H, br.
s); 7.45 (1H, t, J = 7.8H)
6.86-6.94 (2H, m);
21 (1H, br.s); 5.37 (2H, br.s)
4.04 (3H, s); 3.76 (3
H, s); 2.23 (3H, s).

【０３８１】[0381]

【実施例７８】Ｎ−［４−（５−メトキシカルボニルベンゾオキサゾー
ル−２−イルメトキシ）−２−メチルフェニル］アセト
アミド（化合物番号Ｇ１．１１７）融点：175 −183 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.37 (1H,
d, J=1.5 Hz); 8.06 (1H,dd, J=1.5 & 8.7 Hz); 7.55
(1H, d, J=8.7 Hz); 7.31 (1H, d, J=8.5 Hz); 6.78-6.
92 (2H, m); 5.25 (2H, s); 3.90 (3H, s); 2.16 (3H,
s); 2.09 (3H, s).Working Example 78 N- [4- (5-methoxycarbonylbenzoxazo)
Ru-2-ylmethoxy) -2-methylphenyl] aceto
Amide (Compound No. G1.117) Melting point: 175-183 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.37 (1H,
d, J = 1.5 Hz); 8.06 (1H, dd, J = 1.5 & 8.7 Hz); 7.55
(1H, d, J = 8.7 Hz); 7.31 (1H, d, J = 8.5 Hz); 6.78-6.
92 (2H, m); 5.25 (2H, s); 3.90 (3H, s); 2.16 (3H,
s); 2.09 (3H, s).

【０３８２】[0382]

【実施例７９】メチルＮ−［４−（５−メトキシカルボニルベンゾオ
キサゾール−２−イルメトキシ）−２−メチルフェニ
ル］カルバマート（化合物番号G1.118）融点：132 −135 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.45 (1H,
d, J=1.2 Hz); 8.13 (1H,dd, J=1.2 & 8.6 Hz); 7.59
(1H, d, J=8.6 Hz); 7.55 (1H, br.s); 6.85-6.94(2H,
m); 6.21 (1H, br.s); 5.31 (2H, s); 3.96 (3H, s);
3.76 (3H, s); 2.24 (3H, s).Working Example 79 Methyl N- [4- (5-methoxycarbonylbenzoo)
Xazol-2-ylmethoxy) -2-methylpheni
] Carbamate (compound number G1.118) melting point: 132-135 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.45 (1H,
d, J = 1.2 Hz); 8.13 (1H, dd, J = 1.2 & 8.6 Hz); 7.59
(1H, d, J = 8.6 Hz); 7.55 (1H, br.s); 6.85-6.94 (2H,
m); 6.21 (1H, br.s); 5.31 (2H, s); 3.96 (3H, s);
3.76 (3H, s); 2.24 (3H, s).

【０３８３】[0383]

【実施例８０】Ｎ−［４−（６−メトキシカルボニルベンゾオキサゾー
ル−２−イルメトキシ）−２−メチルフェニル］アセト
アミド（化合物番号G1.121）融点：148 −153 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.25 (1H,
d, J=1.4 Hz); 8.09 (1H,dd, J=1.4 & 8.4 Hz); 7.53
(1H, d, J=8.5 Hz); 6.83-6.94 (2H, m); 5.31 (2H,
s); 3.96 (3H, s); 2.23 (3H, s); 2.18 (3H, s).Working Example 80 N- [4- (6-methoxycarbonylbenzoxazo)
Ru-2-ylmethoxy) -2-methylphenyl] aceto
Amide (Compound No. G1.121) Melting point: 148-153 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.25 (1H,
d, J = 1.4 Hz); 8.09 (1H, dd, J = 1.4 & 8.4 Hz); 7.53
(1H, d, J = 8.5 Hz); 6.83-6.94 (2H, m); 5.31 (2H,
s); 3.96 (3H, s); 2.23 (3H, s); 2.18 (3H, s).

【０３８４】[0384]

【実施例８１】メチルＮ−［４−（６−メトキシカルボニルベンゾオ
キサゾール−２−イルメトキシ）−２−メチルフェニ
ル］カルバマート（化合物番号G1.122）融点：約 190℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.25 (1H,
d, J=0.8 Hz); 8.11 (1H,dd, J=0.8 & 8.4 Hz); 7.79
(1H, d, J=8.4 Hz); 7.54 (1H, br.s); 6.84-6.93(2H,
m); 6.21 (1H, br.s); 5.32 (2H, s); 3.97 (3H, s);
3.76 (3H, s); 2.24 (3H, s).Example 81: Methyl N- [4- (6-methoxycarbonylbenzoo)
Xazol-2-ylmethoxy) -2-methylpheni
] Carbamate (compound number G1.122) melting point: about 190 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.25 (1H,
d, J = 0.8 Hz); 8.11 (1H, dd, J = 0.8 & 8.4 Hz); 7.79
(1H, d, J = 8.4 Hz); 7.54 (1H, br.s); 6.84-6.93 (2H,
m); 6.21 (1H, br.s); 5.32 (2H, s); 3.97 (3H, s);
3.76 (3H, s); 2.24 (3H, s).

【０３８５】[0385]

【実施例８２】Ｎ−［４−（７−メトキシカルボニルベンゾオキサゾー
ル−２−イルメトキシ）−２−メチルフェニル］アセト
アミド（化合物番号G1.127）融点：150 −160 ℃ ＮＭＲスペクトル(270MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.0 Hz); 7.95 (1H,d, J=7.6 Hz); 7.57-7.40 (2
H, m); 6.96-6.89 (3H, m)5.34 (2H, s); 4.01 (3H,
s); 2.23 (3H, s).2.18 (3H, s).Working Example 82 N- [4- (7-methoxycarbonylbenzoxazole)
Ru-2-ylmethoxy) -2-methylphenyl] aceto
Amide (Compound No. G1.127) Melting point: 150-160 ° C NMR spectrum (270 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.0 Hz); 7.95 (1H, d, J = 7.6 Hz); 7.57-7.40 (2
H, m); 6.96-6.89 (3H, m) 5.34 (2H, s); 4.01 (3H,
s); 2.23 (3H, s) .2.18 (3H, s).

【０３８６】[0386]

【実施例８３】メチルＮ−［４−（７−メトキシカルボニルベンゾオ
キサゾール−２−イルメトキシ）−２−メチルフェニ
ル］カルバマート（化合物番号G1.128）融点：139 −141 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.02 (1H,
d, J=7.9 Hz); 7.95 (1H,d, J=8.0 & 1.3 Hz ); 7.46-
7.33 (2H, m); 6.94-6.88 (2H, m); 6.26 (1H, br.s);
5.34 (2H, s); 4.01 (3H, s); 3.75 (3H, s); 2.23 (3
H, s).Working Example 83 Methyl N- [4- (7-methoxycarbonylbenzoic)
Xazol-2-ylmethoxy) -2-methylpheni
] Carbamate (Compound No. G1.128) Melting point: 139-141 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.02 (1H,
d, J = 7.9 Hz); 7.95 (1H, d, J = 8.0 & 1.3 Hz); 7.46-
7.33 (2H, m); 6.94-6.88 (2H, m); 6.26 (1H, br.s);
5.34 (2H, s); 4.01 (3H, s); 3.75 (3H, s); 2.23 (3
H, s).

【０３８７】[0387]

【実施例８４】Ｎ−［４−（５，７−ジメチルベンゾオキサゾール−２
−イルメトキシ）−２−メチルフェニル］アセトアミド
（化合物番号G2.13 ）融点：207 −210 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.54-7.49
(1H, m); 7.35-7.34 (1H,m); 6.98-6.83 (4H, m); 5.26
(2H, s); 2.48 (3H, s); 2.42 (3H, s); 2.23 (3H,
s); 2.18 (3H, s). Working Example 84 N- [4- (5,7-dimethylbenzoxazole-2)
-Ylmethoxy) -2-methylphenyl] acetamide
(Compound No. G2.13) Melting point: 207-210 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.54-7.49
(1H, m); 7.35-7.34 (1H, m); 6.98-6.83 (4H, m); 5.26
(2H, s); 2.48 (3H, s); 2.42 (3H, s); 2.23 (3H, s)
s); 2.18 (3H, s).

【０３８８】[0388]

【実施例８５】Ｎ−［４−（６，７−ジフルオロベンゾオキサゾール−
２−イルメトキシ）−２−メチルフェニル］アセトアミ
ド（化合物番号G2.49 ）融点：164 −165 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.54-7.50
(1H, m); 7.51-7.42 (1H,m); 7.28-7.15 (1H, m); 6.91
-6.80 (3H, m); 5.29 (2H, s); 2.24 (3H, s); 2.19 (3
H, s). Working Example 85 N- [4- (6,7-difluorobenzoxazole-
2-ylmethoxy) -2-methylphenyl] acetami
(Compound number G2.49) Melting point: 164-165 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.54-7.50
(1H, m); 7.51-7.42 (1H, m); 7.28-7.15 (1H, m); 6.91
-6.80 (3H, m); 5.29 (2H, s); 2.24 (3H, s); 2.19 (3
H, s).

【０３８９】[0389]

【実施例８６】Ｎ−［４−（５，７−ジクロロベンゾオキサゾール−２
−イルメトキシ）−２−メチルフェニル］アセトアミド
（化合物番号G2.61 ）融点：190 −193 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.64 (1H,
d, J=1.9 Hz); 7.58-7.40(1H, m); 6.93-6.81 (3H, m);
5.29 (2H, s); 2.24 (3H, s); 2.19 (3H, s). Working Example 86 N- [4- (5,7-dichlorobenzoxazole-2)
-Ylmethoxy) -2-methylphenyl] acetamide
(Compound No. G2.61) Melting point: 190-193 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.64 (1H,
d, J = 1.9 Hz); 7.58-7.40 (1H, m); 6.93-6.81 (3H, m);
5.29 (2H, s); 2.24 (3H, s); 2.19 (3H, s).

【０３９０】[0390]

【実施例８７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニチルプロピオンアミド（化合物番号A1.32 ）融点：156 −158 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.2 Hz); 7.90 (1H,dd, J=8.1 & 1.4 Hz); 7.56-
7.35 (2H, m); 7.46 (2H, d, J=9.0 Hz); 7.23 (1H, b
r.s); 7.00 (2H, d, J=9.0 Hz); 5.40 (2H, s); 1.30
(9H, s)Example 87 N- [4- (benzothiazol-2-ylmethoxy) phenyl
Enthylpropionamide (Compound No. A1.32) Melting point: 156-158 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.03 (1H,
d, J = 7.2 Hz); 7.90 (1H, dd, J = 8.1 & 1.4 Hz); 7.56-
7.35 (2H, m); 7.46 (2H, d, J = 9.0 Hz); 7.23 (1H, b
rs); 7.00 (2H, d, J = 9.0 Hz); 5.40 (2H, s); 1.30
(9H, s)

【０３９１】[0391]

【実施例８８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−２−エトキシアセトアミド（化
合物番号C1.36 ）融点：94−95℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.17 (br.
s),8.03 (1H, dd, J=8.0 & 1.3 Hz); 7.95 (1H, dd, J=
8.0 & 1.3 Hz); 7.83-7.78(1H, m); 7.50 (1H, td, J=
8.0 & 1.3 Hz); 7.39 (1H, td, J=8.0 & 1.3 Hz);6.92-
6.88 (2H, m); 5.46 (2H, s); 4.08 (2H, s); 3.67 (2
H, q, J=7.9 Hz); 2.25 (3H, s); 1.30 (3H, t, J=7.0
Hz). Working Example 88 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -2-ethoxyacetamide
Compound No. C1.36) Melting point: 94-95 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.17 (br.
s), 8.03 (1H, dd, J = 8.0 & 1.3 Hz); 7.95 (1H, dd, J =
8.0 & 1.3 Hz); 7.83-7.78 (1H, m); 7.50 (1H, td, J =
8.0 & 1.3 Hz); 7.39 (1H, td, J = 8.0 & 1.3 Hz); 6.92
6.88 (2H, m); 5.46 (2H, s); 4.08 (2H, s); 3.67 (2
H, q, J = 7.9 Hz); 2.25 (3H, s); 1.30 (3H, t, J = 7.0
Hz).

【０３９２】[0392]

【実施例８９】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メトキシカルボニルフェニル］アセトアミド（化合
物番号C10.78）融点：192 −193 ℃ ＮＭＲスペクトル(200MHz, DMSO-d₆）, δppm: 10.22
(1H, br.s); 8.14 (1H, d, J=7.5 Hz); 8.03 (2H, br.
d, J=7.9 Hz); 7.61-7.34 (4H, m); 5.65 (2H, s);3.84
(3H, s); 2.08 (3H, s). Working Example 89 N- [4- (benzothiazol-2-ylmethoxy)-
2-methoxycarbonylphenyl] acetamide (compound
Article No. C10.78) Melting point: 192-193 ° C NMR spectrum (200 MHz, DMSO-d ₆ ), δppm: 10.22
(1H, br.s); 8.14 (1H, d, J = 7.5 Hz); 8.03 (2H, br.s)
d, J = 7.9 Hz); 7.61-7.34 (4H, m); 5.65 (2H, s); 3.84
(3H, s); 2.08 (3H, s).

【０３９３】[0393]

【実施例９０】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２，３，６−トリクロロフェニル］アセトアミド（化合
物番号C14.74）融点：194 −197 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.95 (1H,
d, J=7.7 Hz); 7.86 (1H,dd, J=1.2 & 7.7 Hz); 7.32-
7.50 (2H, m); 7.09 (1H, s); 5.47 (2H, s); 2.13 (3
H, s). Working Example 90 N- [4- (benzothiazol-2-ylmethoxy)-
2,3,6-trichlorophenyl] acetamide (compound
Product No. C14.74) Melting point: 194-197 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 7.95 (1H,
d, J = 7.7 Hz); 7.86 (1H, dd, J = 1.2 & 7.7 Hz); 7.32-
7.50 (2H, m); 7.09 (1H, s); 5.47 (2H, s); 2.13 (3
H, s).

【０３９４】[0394]

【実施例９１】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］−４−ブロモブチルアミド（化合物番号A1.58
）融点：163 −165 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05-8.01
(1H, m); 7.93-7.88 (1H,m); 7.51-7.28 (4H, m); 7.11
(1H, br.s); 7.03-6.99 (2H, m); 5.47 (2H, s); 3.54
(2H, t, J=6.2 Hz); 2.55 (2H, t, J=6.9 Hz); 2.28
(2H, t, J=6.3 Hz). Working Example 91 N- [4- (benzothiazol-2-ylmethoxy) phenyl
Enyl] -4-bromobutyramide (Compound No. A1.58
) Mp: 163 -165 ° C. NMR spectrum _{(200MHz, CDCl 3), δppm} : 8.05-8.01
(1H, m); 7.93-7.88 (1H, m); 7.51-7.28 (4H, m); 7.11
(1H, br.s); 7.03-6.99 (2H, m); 5.47 (2H, s); 3.54
(2H, t, J = 6.2 Hz); 2.55 (2H, t, J = 6.9 Hz); 2.28
(2H, t, J = 6.3 Hz).

【０３９５】[0395]

【実施例９２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］−５−ブロモペンタンアミド（化合物番号A1.6
0 ）融点：151 −153 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05-8.01
(1H, m); 7.92-7.87 (1H,m); 7.51-7.40 (4H, m); 7.05
-6.98 (3H, m); 5.47 (2H, s); 3.48-3.42 (2H,m); 2.3
8-2.35 (2H, m); 1.95-1.90 (4H, br.m). Working Example 92 N- [4- (benzothiazol-2-ylmethoxy) phenyl
Enyl] -5-bromopentanamide (compound number A1.6
0) Melting point: 151-153 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.05-8.01
(1H, m); 7.92-7.87 (1H, m); 7.51-7.40 (4H, m); 7.05
-6.98 (3H, m); 5.47 (2H, s); 3.48-3.42 (2H, m); 2.3
8-2.35 (2H, m); 1.95-1.90 (4H, br.m).

【０３９６】[0396]

【実施例９３】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］−２−メトキシアセトアミド（化合物番号A1.6
2 ）融点：140 −143 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.16 (1H, b
r.s); 8.03 (1H, d, J=7.4 Hz); 7.90 (1H, d, J=8.8 H
z); 7.51 (2H, d, J=9.1 Hz); 7.10 (2H, d, J=9.1 H
z); 5.47 (2H, s); 4.00 (2H, s); 3.50 (3H, s). Working Example 93 N- [4- (benzothiazol-2-ylmethoxy) phenyl
Enyl] -2-methoxyacetamide (Compound No.A1.6
2) Melting point: 140-143 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.16 (1H, b
rs); 8.03 (1H, d, J = 7.4 Hz); 7.90 (1H, d, J = 8.8 H
z); 7.51 (2H, d, J = 9.1 Hz); 7.10 (2H, d, J = 9.1 H
z); 5.47 (2H, s); 4.00 (2H, s); 3.50 (3H, s).

【０３９７】[0397]

【実施例９４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］−２−エトキシアセトアミド（化合物番号A1.6
5 ）融点：118 −120 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.22 (1H, b
r.s); 8.03 (1H, d, J=7.7 Hz); 7.90 (1H, dd, J=6.8
& 0.7 Hz); 7.54-7.35 (2H, m); 7.51 (2H, d, J=9.0 H
z); 7.02 (2H, d, J=9.0 Hz); 5.47 (2H, s); 4.03 (2
H, s); 3.65 (2H,q, J=7.0 Hz); 1.29 (3H, t, J=7.0 H
z).Example 94 N- [4- (benzothiazol-2-ylmethoxy) phenyl
Enyl] -2-ethoxyacetamide (Compound No. A1.6
5) Melting point: 118-120 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.22 (1H, b
rs); 8.03 (1H, d, J = 7.7 Hz); 7.90 (1H, dd, J = 6.8
& 0.7 Hz); 7.54-7.35 (2H, m); 7.51 (2H, d, J = 9.0 H
z); 7.02 (2H, d, J = 9.0 Hz); 5.47 (2H, s); 4.03 (2
H, s); 3.65 (2H, q, J = 7.0 Hz); 1.29 (3H, t, J = 7.0 H
z).

【０３９８】[0398]

【実施例９５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）フ
ェニル］−３−メトキシプロピオンアミド（化合物番号
A1.70 ）融点：156 −158 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.12 (1H, b
r.s),8.03 (1H, d, J=8.0 Hz); 7.90 (1H, d, J=7.7 H
z); 7.54-7.36 (2H, m); 7.45(2H, d, J=8.9 Hz); 6.99
(2H, d, J=8.9 Hz); 5.47 (2H, s); 3.71 (2H, t, J=
5.5 Hz); 3.43 (3H, s); 2.61 (2H, t, J=5.5 Hz).Example 95 N- [4- (benzothiazol-2-ylmethoxy) phenyl
Enyl] -3-methoxypropionamide (compound number
A1.70) Melting point: 156-158 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.12 (1H, b
rs), 8.03 (1H, d, J = 8.0 Hz); 7.90 (1H, d, J = 7.7 H
z); 7.54-7.36 (2H, m); 7.45 (2H, d, J = 8.9 Hz); 6.99
(2H, d, J = 8.9 Hz); 5.47 (2H, s); 3.71 (2H, t, J =
5.5 Hz); 3.43 (3H, s); 2.61 (2H, t, J = 5.5 Hz).

【０３９９】[0399]

【実施例９６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−３−メトキシプロピオンアミド
（化合物番号C1.42 ）融点：135 −137 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.14 (1H, b
r.s); 8.03 (1H, d, J=7.9 Hz); 7.89 (1H, d, J=7.9 H
z); 7.81-7.77 (1H, m); 7.50-7.40 (2H, m); 6.89-6.8
6 (2H, m); 5.46 (2H, s); 3.73 (2H, t, J=5.9 Hz);
3.46 (3H, s); 2.66 (2H, t, J=5.9 Hz); 2.23 (3H,
s). Working Example 96 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -3-methoxypropionamide
(Compound No. C1.42) Melting point: 135-137 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.14 (1H, b
rs); 8.03 (1H, d, J = 7.9 Hz); 7.89 (1H, d, J = 7.9 H
z); 7.81-7.77 (1H, m); 7.50-7.40 (2H, m); 6.89-6.8
6 (2H, m); 5.46 (2H, s); 3.73 (2H, t, J = 5.9 Hz);
3.46 (3H, s); 2.66 (2H, t, J = 5.9 Hz); 2.23 (3H, s)
s).

【０４００】[0400]

【実施例９７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メトキシメチルフェニル］アセトアミド（化合物番
号C6.1）融点：157 −160 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.33-8.30
(1H, m); 8.06-8.01 (2H,m); 7.92-7.88 (1H, m); 7.51
-7.40 (2H, m); 7.04-6.98 (1H, m); 6.89-6.88(1H,
m); 5.47 (2H, s); 4.48 (2H, s); 3.37 (3H, s); 2.16
(3H, s). Working Example 97 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methoxymethylphenyl] acetamide (compound number
No. C6.1) Melting point: 157-160 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.33-8.30
(1H, m); 8.06-8.01 (2H, m); 7.92-7.88 (1H, m); 7.51
-7.40 (2H, m); 7.04-6.98 (1H, m); 6.89-6.88 (1H,
m); 5.47 (2H, s); 4.48 (2H, s); 3.37 (3H, s); 2.16
(3H, s).

【０４０１】[0401]

【実施例９８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−エトキシメチルフェニル］アセトアミド（化合物番
号C6.29 ）融点：154 −156 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.52-8.50
(1H, m); 8.08-8.01 (2H,m); 7.93-7.88 (1H, m); 7.54
-7.40 (2H, m); 7.03-6.97 (1H, m); 6.88-6.87(1H,
m); 5.46 (2H, s); 4.53 (2H, s); 3.53 (2H, q, J=7.1
Hz); 2.16 (3H, s); 1.25 (3H, t, J=7.0 Hz). Working Example 98 N- [4- (Benzothiazol-2-ylmethoxy)-
2-ethoxymethylphenyl] acetamide (compound number
No. C6.29) Melting point: 154-156 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.52-8.50
(1H, m); 8.08-8.01 (2H, m); 7.93-7.88 (1H, m); 7.54
-7.40 (2H, m); 7.03-6.97 (1H, m); 6.88-6.87 (1H,
m); 5.46 (2H, s); 4.53 (2H, s); 3.53 (2H, q, J = 7.1
Hz); 2.16 (3H, s); 1.25 (3H, t, J = 7.0 Hz).

【０４０２】[0402]

【実施例９９】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メトキシフェニル］アセトアミド（化合物番号C8.
1）融点：163 −165 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.24 (1H,
d, J=8.8 Hz); 8.06 (1H,dd, J=1.2 & 7.7 Hz); 7.90
(1H, dd, J=1.2 & 8.1 Hz); 7.55-7.40 (3H, m);6.65-
6.58 (2H, m); 5.47 (2H, s); 3.87 (3H, s); 2.18 (3
H, s). Working Example 99 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methoxyphenyl] acetamide (compound number C8.
1) Melting point: 163-165 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.24 (1H,
d, J = 8.8 Hz); 8.06 (1H, dd, J = 1.2 & 7.7 Hz); 7.90
(1H, dd, J = 1.2 & 8.1 Hz); 7.55-7.40 (3H, m); 6.65-
6.58 (2H, m); 5.47 (2H, s); 3.87 (3H, s); 2.18 (3
H, s).

【０４０３】[0403]

【実施例１００】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−メトキシフェニル］アセトアミド（化合物番号C
8.2）融点：118 −119 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.24 (1H,
d, J=8.8 Hz); 7.79-7.74(1H, m); 7.59-7.54 (2H, m);
7.39-7.35 (2H, m); 6.67-6.59 (2H, m); 5.31(2H,
s); 3.85 (3H, s); 2.18 (3H, s). Working Example 100 N- [4- (benzoxazol-2-ylmethoxy)
-2-methoxyphenyl] acetamide (Compound No. C
8.2) Melting point: 118-119 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.24 (1H,
d, J = 8.8 Hz); 7.79-7.74 (1H, m); 7.59-7.54 (2H, m);
7.39-7.35 (2H, m); 6.67-6.59 (2H, m); 5.31 (2H, m
s); 3.85 (3H, s); 2.18 (3H, s).

【０４０４】[0404]

【実施例１０１】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−３−メトキシフェニル］アセトアミド（化合物番号C
8.22 ）融点：98−100 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．７
６−７．７１（１Ｈ，ｍ）；７．５８−７．５３
（１Ｈ，ｍ）；７．４２−７．３３（３Ｈ，
ｍ）；７．２３（１Ｈ，ｂｒ．ｓ）；６．９８
（１Ｈ，ｄ，Ｊ＝８．６Ｈｚ）；６．７５
（１Ｈ，ｄｄ，Ｊ＝８．６＆２．２Ｈｚ）；
５．３３（２Ｈ，ｓ）；３．８６（３Ｈ，
ｓ）；２．１４（３Ｈ，ｓ）． Working Example 101 N- [4- (benzoxazol-2-ylmethoxy)
-3-methoxyphenyl] acetamide (Compound No. C
8.22) Melting point: 98-100 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.7
6-7.71 (1H, m); 7.58-7.53
(1H, m); 7.42-7.33 (3H,
m); 7.23 (1H, br.s); 6.98
(1H, d, J = 8.6 Hz); 6.75
(1H, dd, J = 8.6 & 2.2 Hz);
5.33 (2H, s); 3.86 (3H,
s); 2.14 (3H, s).

【０４０５】[0405]

【実施例１０２】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−３−フルオロフェニル］アセトアミド（化合物番号Ｃ
９．２２）融点：140 −142 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.78-7.74
(1H, m); 7.59-7.55 (1H,m); 7.49-7.35 (3H, m); 7.10
-7.06 (3H, m); 5.36 (2H, s); 2.16 (3H, s). Working Example 102 N- [4- (benzoxazol-2-ylmethoxy)
-3-fluorophenyl] acetamide (Compound No. C
9.22) Melting point: 140-142 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.78-7.74
(1H, m); 7.59-7.55 (1H, m); 7.49-7.35 (3H, m); 7.10
-7.06 (3H, m); 5.36 (2H, s); 2.16 (3H, s).

【０４０６】[0406]

【実施例１０３】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−トリフルオロメチルフェニル］アセトアミド（化
合物番号C10.3 ）融点：145 −147 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.99 (1H, d
d, J=9.7 & 1.0 Hz); 7.80-7.75 (1H, m); 7.59-7.55
(1H, m); 7.43-7.24 (4H, m); 5.35 (2H, s); 2.20 (3
H.s).Example 103 N- [4- (benzoxazol-2-ylmethoxy)
-2-trifluoromethylphenyl] acetamide
Compound No. C10.3) Melting point: 145-147 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.99 (1H, d
d, J = 9.7 & 1.0 Hz); 7.80-7.75 (1H, m); 7.59-7.55
(1H, m); 7.43-7.24 (4H, m); 5.35 (2H, s); 2.20 (3
Hs).

【０４０７】[0407]

【実施例１０４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−トリフルオロメチルフェニル］アセトアミド（化合
物番号C10.17）融点：174 −175 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.94 (1H,
d, J=7.4 Hz); 7.85 (1H,d, J=7.4 Hz); 7.61-7.74 (2
H, m); 7.31-7.49 (2H, m); 7.01 (1H, d, J=8.8Hz);
5.46 (2H, s); 2.06 (3H, s). Working Example 104 N- [4- (benzothiazol-2-ylmethoxy)-
3-trifluoromethylphenyl] acetamide (compound
Product No. C10.17) Melting point: 174-175 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.94 (1H,
d, J = 7.4 Hz); 7.85 (1H, d, J = 7.4 Hz); 7.61-7.74 (2
H, m); 7.31-7.49 (2H, m); 7.01 (1H, d, J = 8.8Hz);
5.46 (2H, s); 2.06 (3H, s).

【０４０８】[0408]

【実施例１０５】Ｎ−［２−アセチル−４−（ベンゾチアゾール−２−イ
ルメトキシ）フェニル］アセトアミド（化合物番号C10.
42）融点：134 −137 ℃ ＮＭＲスペクトル(200MHz, acetone-d₆ ）, δppm: 11.
30 (1H, br.s); 8.65 (1H, d, J=9.2 Hz); 8.12-8.00
(2H, m); 7.79 (1H, d, J=3.0 Hz); 7.60-7.35 (3H,
m); 5.65 (2H, s); 2.71 (3H, s); 2.12 (3H, s).Working Example 105 N- [2-acetyl-4- (benzothiazole-2-i
Rumethoxy) phenyl] acetamide (Compound No.C10.
42) Melting point: 134 -137 ° C. NMR spectrum _{(200MHz, acetone-d 6)} , δppm: 11.
30 (1H, br.s); 8.65 (1H, d, J = 9.2 Hz); 8.12-8.00
(2H, m); 7.79 (1H, d, J = 3.0 Hz); 7.60-7.35 (3H,
m); 5.65 (2H, s); 2.71 (3H, s); 2.12 (3H, s).

【０４０９】[0409]

【実施例１０６】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−ニトロフェニル］アセトアミド（化合物番号C10.
49）融点：162 −165 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 10.11 (1H,
br.s); 8.71 (1H, d, J=9.3 Hz); 7.89 (1H, d, J=3.1
Hz); 7.79-7.75 (1H, m); 7.60-7.55 (1H, m); 7.44-7.
36 (3H, m); 5.38 (2H, s); 2.27 (3H, s). Working Example 106 N- [4- (benzoxazol-2-ylmethoxy)
-2-nitrophenyl] acetamide (compound number C10.
49) Melting point: 162-165 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 10.11 (1H,
br.s); 8.71 (1H, d, J = 9.3 Hz); 7.89 (1H, d, J = 3.1
Hz); 7.79-7.75 (1H, m); 7.60-7.55 (1H, m); 7.44-7.
36 (3H, m); 5.38 (2H, s); 2.27 (3H, s).

【０４１０】[0410]

【実施例１０７】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］ペンタンアミド（化合物番号F4.2
0 ）融点：189 −191 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.82 (1H, d
d, J=8.9 & 5.1 Hz); 7.70 (1H, dd, J=9.4 & 2.4 Hz);
7.45 (2H, d, J=8.9 Hz); 7.18 (1H, td, Jt =8.8 Hz
& Jd=2.6 Hz); 7.05 (1H, br.s); 6.99 (2H, d, J=9.1
Hz); 5.45 (2H, s); 2.34 (2H, t, J=7.6 Hz); 1.71 (2
H, sextet, J=7.5 Hz); 1.40 (2H, quintet, J=7.5 H
z); 0.95 (3H, t, J=7.2 Hz).Working Example 107 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) phenyl] pentanamide (Compound No. F4.2
0) Melting point: 189-191 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 7.82 (1H, d
d, J = 8.9 & 5.1 Hz); 7.70 (1H, dd, J = 9.4 & 2.4 Hz);
7.45 (2H, d, J = 8.9 Hz); 7.18 (1H, td, Jt = 8.8 Hz
& Jd = 2.6 Hz); 7.05 (1H, br.s); 6.99 (2H, d, J = 9.1
Hz); 5.45 (2H, s); 2.34 (2H, t, J = 7.6 Hz); 1.71 (2
H, sextet, J = 7.5 H); 1.40 (2H, quintet, J = 7.5 H)
z); 0.95 (3H, t, J = 7.2 Hz).

【０４１１】[0411]

【実施例１０８】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］シクロヘキサンカルボキサミド
（化合物番号F4.22 ）融点：211 −212 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．８
２（１Ｈ，ｄｄ，Ｊ＝９．０＆５．１Ｈ
ｚ）；７．７０（１Ｈ，ｄｄ，Ｊ＝９．２＆
２．５Ｈｚ）；７．４６（２Ｈ，ｄ，Ｊ＝
９．１Ｈｚ）；７．１８（１Ｈ，ｔｄ，Ｊ＝
８．８＆２．５Ｈｚ）；７．０５（１Ｈ，ｂ
ｒ．ｓ）；６．９９（２Ｈ，ｄ，Ｊ＝９．１
Ｈｚ）；５．４５（２Ｈ，ｓ）；２．３０−
２．１０（１Ｈ，ｍ）；２．０３−１．１８
（１０Ｈ，ｍ）．Working Example 108 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) phenyl] cyclohexanecarboxamide
(Compound No. F4.22) melting point: 211-212 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.8
2 (1H, dd, J = 9.0 & 5.1 H
7.70 (1H, dd, J = 9.2 &
7.46 (2H, d, J =
9.1 Hz); 7.18 (1H, td, J =
8.8 & 2.5 Hz); 7.05 (1H, b
r. s); 6.99 (2H, d, J = 9.1)
Hz); 5.45 (2H, s); 2.30-
2.10 (1H, m); 2.03-1.18
(10H, m).

【０４１２】[0412]

【実施例１０９】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］−２−フルオロアセトアミド（化
合物番号Ｆ４．２３）融点：192 −193 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.84 (1H, b
r.s); 7.83 (1H, dd, J=8.8 & 5.1 Hz); 7.71 (1H, dd,
J=7.4 & 2.5 Hz); 7.51 (2H, d, J=9.1 Hz); 7.19 (1
H, td, J=8.8 & 2.4 Hz); 7.03 (2H, d, J=9.0 Hz); 5.
47 (2H, s); 4.92(2H, d, J=47.5 Hz).Working Example 109 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) phenyl] -2-fluoroacetamide
Compound No. F4.23) Melting point: 192 ° -193 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.84 (1H, b
rs); 7.83 (1H, dd, J = 8.8 & 5.1 Hz); 7.71 (1H, dd,
J = 7.4 & 2.5 Hz); 7.51 (2H, d, J = 9.1 Hz); 7.19 (1
H, td, J = 8.8 & 2.4 Hz); 7.03 (2H, d, J = 9.0 Hz); 5.
47 (2H, s); 4.92 (2H, d, J = 47.5 Hz).

【０４１３】[0413]

【実施例１１０】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］−２−クロロアセトアミド（化合
物番号F4.25 ）融点：198 −200 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.18 (1H, b
r.s); 7.83 (1H, dd, J=8.8 & 5.1 Hz); 7.71 (1H, dd,
J=9.6 & 2.6 Hz); 7.49 (2H, d, J=9.0 Hz); 7.19 (1
H, td, J=8.8 & 2.4 Hz); 7.03 (2H, d, J=9.1 Hz); 5.
47 (2H, s); 4.19(2H, s).Working Example 110 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) phenyl] -2-chloroacetamide (compound
Article number F4.25) Melting point: 198-200 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.18 (1H, b
rs); 7.83 (1H, dd, J = 8.8 & 5.1 Hz); 7.71 (1H, dd,
J = 9.6 & 2.6 Hz); 7.49 (2H, d, J = 9.0 Hz); 7.19 (1
H, td, J = 8.8 & 2.4 Hz); 7.03 (2H, d, J = 9.1 Hz); 5.
47 (2H, s); 4.19 (2H, s).

【０４１４】[0414]

【実施例１１１】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］−２，２−ジクロロアセトアミド
（化合物番号F4.27 ）融点：208 −209 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
５（１Ｈ，ｂｒ．ｓ）；７．８３（１Ｈ，ｄ
ｄ，Ｊ＝８．９＆５．１Ｈｚ）；７．７１
（１Ｈ，ｄｄ，Ｊ＝９．３＆２．０Ｈｚ）；
７．５０（２Ｈ，ｄ，Ｊ＝９．１Ｈｚ）；
７．１９（１Ｈ，ｔ，ｄ，Ｊ＝８．８，２．５
Ｈｚ）；７．０５（２Ｈ，ｄ，Ｊ＝９．１
Ｈｚ）；６．０３（１Ｈ，ｓ）；５．４８（２
Ｈ，ｓ）．Working Example 111 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) phenyl] -2,2-dichloroacetamide
(Compound No. F4.27) Melting point: 208-209 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
5 (1H, br.s); 7.83 (1H, d
d, J = 8.9 & 5.1 Hz); 7.71
(1H, dd, J = 9.3 & 2.0 Hz);
7.50 (2H, d, J = 9.1 Hz);
7.19 (1H, t, d, J = 8.8, 2.5
Hz); 7.05 (2H, d, J = 9.1)
Hz); 6.03 (1H, s); 5.48 (2
H, s).

【０４１５】[0415]

【実施例１１２】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］−２，２，２−トリフルオロアセ
トアミド（化合物番号Ｆ４．２８）融点：204 −206 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.88-7.68
(3H, m); 7.52 (2H, d, J=9.0 Hz); 7.20-7.14 (1H,
m); 7.06 (2H, d, J=9.1 Hz); 5.48 (2H, s).Working Example 112 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) phenyl] -2,2,2-trifluoroace
Toamide (Compound No. F4.28) Melting point: 204-206 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.88-7.68
(3H, m); 7.52 (2H, d, J = 9.0 Hz); 7.20-7.14 (1H,
m); 7.06 (2H, d, J = 9.1 Hz); 5.48 (2H, s).

【０４１６】[0416]

【実施例１１３】Ｓ−メチルＮ−［４−（ベンゾチアゾール−２−イル
メトキシ）フェニル］ジチオカルバマート（化合物番号
A1.16 ）融点：136 −138 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.70-8.65
(1H, br.m); 8.07-8.03 (1H, m); 7.94-7.89 (1H, m);
7.55-7.33 (3H, m); 7.09-7.04 (2H, m); 5.51 (2H,
s); 2.64 (3H, s). Working Example 113 S-methyl N- [4- (benzothiazol-2-yl)
Methoxy) phenyl] dithiocarbamate (compound number
A1.16) Melting point: 136-138 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.70-8.65
(1H, br.m); 8.07-8.03 (1H, m); 7.94-7.89 (1H, m);
7.55-7.33 (3H, m); 7.09-7.04 (2H, m); 5.51 (2H, m
s); 2.64 (3H, s).

【０４１７】[0417]

【実施例１１４】Ｎ−［４−（ベンゾチアゾール−２−イルメチルチオ)
−２−メチルフェニル］アセトアミド（化合物番号C1.
3）融点：116 −117 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.98-7.72
(3H, m); 7.50-7.20 (4H,m); 6.87 (1H, br.s); 4.48
(2H, s); 2.19 (3H, s).Working Example 114 N- [4- (Benzothiazol-2-ylmethylthio)
-2-methylphenyl] acetamide (compound number C1.
3) Melting point: 116-117 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 7.98-7.72
(3H, m); 7.50-7.20 (4H, m); 6.87 (1H, br.s); 4.48
(2H, s); 2.19 (3H, s).

【０４１８】[0418]

【実施例１１５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−メチルフェニル］アセトアミド（化合物番号C1.52
）融点：157 −159 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05-7.89
(2H, m); 7.51-7.22 (2H,m); 7.05 (1H, br.s); 6.86
(1H, d, J=8.8 Hz); 5.46 (2H, s); 2.35 (3H, s); 2.1
5 (3H, s). Working Example 115 N- [4- (Benzothiazol-2-ylmethoxy)-
3-methylphenyl] acetamide (Compound No. C1.52
) Melting point: 157-159 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.05-7.89
(2H, m); 7.51-7.22 (2H, m); 7.05 (1H, br.s); 6.86
(1H, d, J = 8.8 Hz); 5.46 (2H, s); 2.35 (3H, s); 2.1
5 (3H, s).

【０４１９】[0419]

【実施例１１６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−エチルフェニル］アセトアミド（化合物番号C2.1）融点：165 −168 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=9.2 Hz); 7.90 (1H,dd, J=7.7 & 1.0 Hz); 7.52
(1H, d, J=8.5 Hz); 7.46-7.40 (2H, m); 6.93-6.82 (3
H, m); 5.46 (2H, s); 2.58 (2H, q, J=7.7 Hz); 2.18
(3H, s); 1.22 (3H, t, J=7.7 Hz). Working Example 116 N- [4- (Benzothiazol-2-ylmethoxy)-
2-ethylphenyl] acetamide (Compound No. C2.1) Melting point: 165-168 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 9.2 Hz); 7.90 (1H, dd, J = 7.7 & 1.0 Hz); 7.52
(1H, d, J = 8.5 Hz); 7.46-7.40 (2H, m); 6.93-6.82 (3
H, m); 5.46 (2H, s); 2.58 (2H, q, J = 7.7 Hz); 2.18
(3H, s); 1.22 (3H, t, J = 7.7 Hz).

【０４２０】[0420]

【実施例１１７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−エチルフェニル］アセトアミド（化合物番号C2.19
）融点：135 −137 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.2 Hz); 7.91 (1H,dd, J=6.8 & 0.8 Hz); 7.51-
7.40 (2H, m); 7.31-7.28 (2H, m); 7.03 (1H, br.s);
6.88 (1H, d, J=9.4 Hz); 5.47 (2H, s); 2.77 (2H, q,
J=7.5 Hz); 2.15(3H, s); 1.27 (3H, t, J=7.5 Hz). Working Example 117 N- [4- (Benzothiazol-2-ylmethoxy)-
3-ethylphenyl] acetamide (compound number C2.19
) Melting point: 135-137 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.03 (1H,
d, J = 8.2 Hz); 7.91 (1H, dd, J = 6.8 & 0.8 Hz); 7.51-
7.40 (2H, m); 7.31-7.28 (2H, m); 7.03 (1H, br.s);
6.88 (1H, d, J = 9.4 Hz); 5.47 (2H, s); 2.77 (2H, q,
J = 7.5 Hz); 2.15 (3H, s); 1.27 (3H, t, J = 7.5 Hz).

【０４２１】[0421]

【実施例１１８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−イソプロピルフェニル］アセトアミド（化合物番号
C3.30 ）融点：165 −170 ℃ ＮＭＲスペクトル(270MHz,CDCl₃), δｐｐｍ：８．０
３（１Ｈ，ｄ，Ｊ＝８．７Ｈｚ）；７．９１
（１Ｈ，ｄ，Ｊ＝８．７Ｈｚ）；７．５７−
７．３６（３Ｈ，ｍ）；７．１５−６．７８
（２Ｈ，ｍ）；５．４６（２Ｈ，ｓ）；３．
１０−２．８７（１Ｈ，ｍ）；２．１８（３
Ｈ，ｓ）；１．２１（６Ｈ，ｄ，Ｊ＝６．８
Ｈｚ）． Working Example 118 N- [4- (benzothiazol-2-ylmethoxy)-
2-isopropylphenyl] acetamide (compound number
C3.30) Melting point: 165-170 ° C NMR spectrum (270 MHz, CDCl ₃ ), δ ppm: 8.0
3. (1H, d, J = 8.7 Hz); 7.91
(1H, d, J = 8.7 Hz); 7.57-
7.36 (3H, m); 7.15-6.78
(2H, m); 5.46 (2H, s);
10-2.87 (1H, m); 2.18 (3
H, s); 1.21 (6H, d, J = 6.8)
Hz).

【０４２２】[0422]

【実施例１１９】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−ｔ−ブチルフェニル］アセトアミド（化合物番号Ｃ
４．２７）融点：158 −165 ℃ ＮＭＲスペクトル(270MHz,CDCl₃), δppm: 8.04 (1H,
d, J=8.8 Hz); 7.91 (1H,d, J=8.8 Hz); 7.55-7.30 (2
H, m); 7.18-6.81 (3H, m); 5.46 (2H, s); 2.19(3H,
s); 1.38 (9H, s). Working Example 119 N- [4- (Benzothiazol-2-ylmethoxy)-
2-t-butylphenyl] acetamide (Compound No. C
4.27) Melting point: 158-165 ° C NMR spectrum (270 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 8.8 Hz); 7.91 (1H, d, J = 8.8 Hz); 7.55-7.30 (2
H, m); 7.18-6.81 (3H, m); 5.46 (2H, s); 2.19 (3H,
s); 1.38 (9H, s).

【０４２３】[0423]

【実施例１２０】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−ジフルオロメチルフェニル］アセトアミド（化合物
番号C7.55 ）融点：195 −198 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.7 Hz); 7.91 (1H,dd, J=6.6 & 0.8 Hz); 7.81-
7.77 (1H, m); 7.56-7.42 (2H, m); 7.32 (1H, br.s);
7.17-7.13 (2H, m); 6.65 (1H, t, J=55.3 Hz); 5.50
(2H, s); 2.19 (3H,s). Working Example 120 N- [4- (benzothiazol-2-ylmethoxy)-
2-difluoromethylphenyl] acetamide (compound
No. C7.55) Melting point: 195-198 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.04 (1H,
d, J = 7.7 Hz); 7.91 (1H, dd, J = 6.6 & 0.8 Hz); 7.81-
7.77 (1H, m); 7.56-7.42 (2H, m); 7.32 (1H, br.s);
7.17-7.13 (2H, m); 6.65 (1H, t, J = 55.3 Hz); 5.50
(2H, s); 2.19 (3H, s).

【０４２４】[0424]

【実施例１２１】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−エトキシフェニル］アセトアミド（化合物番号C8.3
9 ）融点：131 −133 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．２
５（１Ｈ，ｄ，Ｊ＝８．５Ｈｚ）；８．０３
（１Ｈ，ｄｄ，Ｊ＝８．５＆１．２Ｈｚ）；
７．９０（１Ｈ，ｄｄ，Ｊ＝７．６＆１．
６Ｈｚ）；７．５６（１Ｈ，ｓ）；７．５１
（１Ｈ，ｔｄ，Ｊ＝７．６＆１．５Ｈｚ）；
７．４０（１Ｈ，ｔｄ，Ｊ＝７．８＆１．
４Ｈｚ）；６．６３−６．５６（１Ｈ，ｍ）；
６．６１（１Ｈ，ｓ）；５．４６（２Ｈ，
ｓ）；４．０９（２Ｈ，ｑ，Ｊ＝７．０Ｈ
ｚ）；２．１８（３Ｈ，ｓ）；１．４６（３
Ｈ，ｔ，Ｊ＝７．０Ｈｚ）． Working Example 121 N- [4- (Benzothiazol-2-ylmethoxy)-
2-ethoxyphenyl] acetamide (Compound No. C8.3
9) Melting point: 131-133 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.2
5 (1H, d, J = 8.5 Hz); 8.03
(1H, dd, J = 8.5 & 1.2 Hz);
7.90 (1H, dd, J = 7.6 & 1.
7.56 (1H, s); 7.51
(1H, td, J = 7.6 & 1.5 Hz);
7.40 (1H, td, J = 7.8 & 1.
4.63-6.56 (1H, m);
6.61 (1H, s); 5.46 (2H,
s); 4.09 (2H, q, J = 7.0 H)
z); 2.18 (3H, s); 1.46 (3
H, t, J = 7.0 Hz).

【０４２５】[0425]

【実施例１２２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−ジフルオロメトキシフェニル］アセトアミド（化合
物番号Ｃ８．７２）融点：120 −121 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.23 (1H,
d, J=9.4 Hz); 8.04 (1H,dd, J=7.1 & 1.4 Hz); 7.91
(1H, dd, J=7.1 & 1.4 Hz); 7.56-7.28 (3H, m);6.92-
6.87 (2H, m); 6.52 (1H, t, J=73.2 Hz); 5.47 (2H,
s); 2.20 (3H, s). Working Example 122 N- [4- (benzothiazol-2-ylmethoxy)-
2-difluoromethoxyphenyl] acetamide (compound
Article No. C8.72) Melting point: 120-121 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.23 (1H,
d, J = 9.4 Hz); 8.04 (1H, dd, J = 7.1 & 1.4 Hz); 7.91
(1H, dd, J = 7.1 & 1.4 Hz); 7.56-7.28 (3H, m); 6.92-
6.87 (2H, m); 6.52 (1H, t, J = 73.2 Hz); 5.47 (2H, m
s); 2.20 (3H, s).

【０４２６】[0426]

【実施例１２３】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−（２，２，２−トリフルオロエトキシ) フェニル］
アセトアミド（化合物番号C8.76 ）融点：136 −138 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.24 (1H,
d, J=9.0 Hz); 8.04 (1H,d, J=7.6 Hz); 7.90 (1H, dd,
J=7.9 & 1.8 Hz); 7.56-7.37 (3H, m); 6.72 (1H, dd,
J=9.0 & 2.6 Hz); 6.64 (1H, d, J=2.6 Hz); 5.47 (2
H, s); 4.40 (2H,q, J=8.0 Hz); 2.19 (3H, s). Working Example 123 N- [4- (Benzothiazol-2-ylmethoxy)-
2- (2,2,2-trifluoroethoxy) phenyl]
Acetamide (Compound No. C8.76) Melting point: 136-138 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.24 (1H,
d, J = 9.0 Hz); 8.04 (1H, d, J = 7.6 Hz); 7.90 (1H, dd,
J = 7.9 & 1.8 Hz); 7.56-7.37 (3H, m); 6.72 (1H, dd,
J = 9.0 & 2.6 Hz); 6.64 (1H, d, J = 2.6 Hz); 5.47 (2
H, s); 4.40 (2H, q, J = 8.0 Hz); 2.19 (3H, s).

【０４２７】[0427]

【実施例１２４】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−フルオロフェニル］アセトアミド（化合物番号C
9.3）融点：135 −136 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.15 (1H,
d, J=8.8 Hz); 7.79-7.74(1H, m); 7.59-7.54 (1H, m);
7.43-7.36 (2H, m); 7.18 (1H, br.s); 6.90-6.83 (2
H, m); 5.30 (2H, s); 2.20 (3H, s).Example 124 N- [4- (benzoxazol-2-ylmethoxy)
-2-fluorophenyl] acetamide (Compound No. C
9.3) Melting point: 135-136 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.15 (1H,
d, J = 8.8 Hz); 7.79-7.74 (1H, m); 7.59-7.54 (1H, m);
7.43-7.36 (2H, m); 7.18 (1H, br.s); 6.90-6.83 (2
H, m); 5.30 (2H, s); 2.20 (3H, s).

【０４２８】[0428]

【実施例１２５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−フルオロフェニル］アセトアミド（化合物番号C9.2
0 ）融点：150 −151 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05-7.89
(2H, m); 7.51-7.28 (3H,m); 7.04-7.02 (3H, m); 5.53
(2H, s); 2.16 (3H, s). Working Example 125 N- [4- (Benzothiazol-2-ylmethoxy)-
3-Fluorophenyl] acetamide (Compound No. C9.2
0) Melting point: 150-151 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.05-7.89
(2H, m); 7.51-7.28 (3H, m); 7.04-7.02 (3H, m); 5.53
(2H, s); 2.16 (3H, s).

【０４２９】[0429]

【実施例１２６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−クロロフェニル］アセトアミド（化合物番号C9.36
）融点：159 −161 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.23 (1H,
d, J=9.2 Hz); 8.04 (1H,d, J=8.1 Hz); 7.90 (1H, dd,
J=7.0 & 0.8 Hz); 7.56-7.37 (3H, m); 7.10 (1H, d,
J=2.8 Hz); 6.97 (1H, dd, J=9.2 & 2.8 Hz); 5.45 (2
H, s); 2.22 (3H,s). Working Example 126 N- [4- (Benzothiazol-2-ylmethoxy)-
2-chlorophenyl] acetamide (Compound No. C9.36
) Melting point: 159-161 ° C NMR spectrum (200MHz, CDCl ₃ ), δ ppm: 8.23 (1H,
d, J = 9.2 Hz); 8.04 (1H, d, J = 8.1 Hz); 7.90 (1H, dd,
J = 7.0 & 0.8 Hz); 7.56-7.37 (3H, m); 7.10 (1H, d,
J = 2.8 Hz); 6.97 (1H, dd, J = 9.2 & 2.8 Hz); 5.45 (2
H, s); 2.22 (3H, s).

【０４３０】[0430]

【実施例１２７】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−クロロフェニル］アセトアミド（化合物番号C9.3
8 ）融点：130 −131 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.23 (1H,
d, J=9.0 Hz); 7.79-7.75(1H, m); 7.59-7.55 (1H, m);
7.45-7.29 (3H, m); 7.12 (1H, d, J=2.8 Hz);6.99 (1
H, dd, J=9.0 & 2.8 Hz); 5.29 (2H, s); 2.22 (3H,
s); 1.57 (3H, s). Working Example 127 N- [4- (benzoxazol-2-ylmethoxy)
-2-chlorophenyl] acetamide (compound number C9.3
8) Melting point: 130-131 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.23 (1H,
d, J = 9.0 Hz); 7.79-7.75 (1H, m); 7.59-7.55 (1H, m);
7.45-7.29 (3H, m); 7.12 (1H, d, J = 2.8 Hz); 6.99 (1
H, dd, J = 9.0 & 2.8 Hz); 5.29 (2H, s); 2.22 (3H,
s); 1.57 (3H, s).

【０４３１】[0431]

【実施例１２８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３−クロロフェニル］アセトアミド（化合物番号C9.52
）融点：168 −169 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
３（１Ｈ，ｄ，Ｊ＝８．１Ｈｚ）；７．９２
（１Ｈ，ｄｄ，Ｊ＝６．７＆１．０Ｈｚ）；
７．６７（１Ｈ，ｄ，Ｊ＝２．５Ｈｚ）；
７．６７−７．２７（２Ｈ，ｍ）；７．０８
（１Ｈ，ｂｒ．ｓ）；７．００（１Ｈ，ｄ，
Ｊ＝８．９Ｈｚ）；５．５３（２Ｈ，ｓ）；
２．１６（３Ｈ，ｓ）． Working Example 128 N- [4- (Benzothiazol-2-ylmethoxy)-
3-chlorophenyl] acetamide (Compound No. C9.52
) Melting point: 168-169 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
3. (1H, d, J = 8.1 Hz); 7.92
(1H, dd, J = 6.7 & 1.0 Hz);
7.67 (1H, d, J = 2.5 Hz);
7.67-7.27 (2H, m); 7.08
(1H, br.s); 7.00 (1H, d,
J = 8.9 Hz); 5.53 (2H, s);
2.16 (3H, s).

【０４３２】[0432]

【実施例１２９】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−３−クロロフェニル］アセトアミド（化合物番号Ｃ
９．５４）融点：161 −165 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.78-7.73
(1H, m); 7.63-7.55 (2H,m); 7.43-7.29 (3H, m); 7.09
(1H, br.s); 7.09 (1H, d, J=8.7 Hz); 5.36 (2H, s);
2.16 (3H, s). Working Example 129 N- [4- (benzoxazol-2-ylmethoxy)
-3-chlorophenyl] acetamide (Compound No. C
9.54) Melting point: 161-165 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.78-7.73
(1H, m); 7.63-7.55 (2H, m); 7.43-7.29 (3H, m); 7.09
(1H, br.s); 7.09 (1H, d, J = 8.7 Hz); 5.36 (2H, s);
2.16 (3H, s).

【０４３３】[0433]

【実施例１３０】Ｎ−［３−アセチル−４−（ベンゾチアゾール−２−イ
ルメトキシ）フェニル］アセトアミド（化合物番号C10.
44）融点：233 −238 ℃ ＮＭＲスペクトル(200MHz, DMSO-d₆）, δppm: 10.00
(1H, br.s); 8.17 (1H, d, J=8.3 Hz); 8.05 (1H, d, J
=7.8 Hz); 7.85 (1H, d, J=2.9 Hz); 7.77 (1H, dd, J=
8.8 & 2.9 Hz); 7.62-7.45 (2H, m); 7.31 (1H, d, J=
8.8 Hz); 5.72 (2H,s); 2.67 (3H, s); 2.03 (3H, s).Working Example 130 N- [3-acetyl-4- (benzothiazol-2-i)
Rumethoxy) phenyl] acetamide (Compound No.C10.
44) Melting point: 233-238 ° C NMR spectrum (200 MHz, DMSO-d ₆ ), δppm: 10.00
(1H, br.s); 8.17 (1H, d, J = 8.3 Hz); 8.05 (1H, d, J
= 7.8 Hz); 7.85 (1H, d, J = 2.9 Hz); 7.77 (1H, dd, J =
8.8 & 2.9 Hz); 7.62-7.45 (2H, m); 7.31 (1H, d, J =
8.8 Hz); 5.72 (2H, s); 2.67 (3H, s); 2.03 (3H, s).

【０４３４】[0434]

【実施例１３１】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−３−ニトロフェニル］アセトアミド（化合物番号C10.
65）融点：148 −150 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=2.9 Hz); 7.78-7.72(2H, m); 7.60-7.56 (1H, m);
7.42-7.30 (4H, m); 5.45 (2H, s); 2.19 (3H,s).Example 131 N- [4- (benzoxazol-2-ylmethoxy)
-3-nitrophenyl] acetamide (compound number C10.
65) Melting point: 148-150 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.03 (1H,
d, J = 2.9 Hz); 7.78-7.72 (2H, m); 7.60-7.56 (1H, m);
7.42-7.30 (4H, m); 5.45 (2H, s); 2.19 (3H, s).

【０４３５】[0435]

【実施例１３２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２，３−ジメチルフェニル］アセトアミド（化合物番号
C11.1 ）融点：207 −209 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.0 Hz); 7.91 (1H,d, J=7.6 Hz); 7.51-7.40 (2
H, m); 7.03 (2H, AB q, J=8.9 Hz, Dn=85.6 ）;6.89
(1H, br.s); 5.46 (2H, s); 2.31 (3H, s); 2.19 (6H,
s). Working Example 132 N- [4- (Benzothiazol-2-ylmethoxy)-
2,3-dimethylphenyl] acetamide (compound number
C11.1) Melting point: 207-209 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.0 Hz); 7.91 (1H, d, J = 7.6 Hz); 7.51-7.40 (2
H, m); 7.03 (2H, AB q, J = 8.9 Hz, Dn = 85.6); 6.89
(1H, br.s); 5.46 (2H, s); 2.31 (3H, s); 2.19 (6H,
s).

【０４３６】[0436]

【実施例１３３】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２，５−ジメチルフェニル］アセトアミド（化合物番号
C11.17）融点：90−94℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.5 Hz); 7.92 (1H,d, J=7.7 Hz); 7.51-7.44 (2
H, m); 7.40 (1H, s); 6.80 (1H, s); 6.75 (1H,s); 5.
45 (2H, s); 2.31 (3H, s); 2.20 (3H, s); 2.18 (3H,
s). Working Example 133 N- [4- (Benzothiazol-2-ylmethoxy)-
2,5-dimethylphenyl] acetamide (compound number
C11.17) Melting point: 90-94 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.03 (1H,
d, J = 7.5 Hz); 7.92 (1H, d, J = 7.7 Hz); 7.51-7.44 (2
H, m); 7.40 (1H, s); 6.80 (1H, s); 6.75 (1H, s); 5.
45 (2H, s); 2.31 (3H, s); 2.20 (3H, s); 2.18 (3H, s)
s).

【０４３７】[0437]

【実施例１３４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２，６−ジメチルフェニル］アセトアミド（化合物番号
C11.33）融点：198 −204 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.8 Hz); 7.91 (1H,dd, J=7.7 & 0.8 Hz); 7.51-
7.41 (2H, m); 6.77 (2H, s); 6.59 (1H, s); 5.44 (2
H, s); 2.22 (6H, s); 2.20 (3H, s). Working Example 134 N- [4- (benzothiazol-2-ylmethoxy)-
2,6-dimethylphenyl] acetamide (compound number
C11.33) Melting point: 198-204 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.8 Hz); 7.91 (1H, dd, J = 7.7 & 0.8 Hz); 7.51-
7.41 (2H, m); 6.77 (2H, s); 6.59 (1H, s); 5.44 (2
H, s); 2.22 (6H, s); 2.20 (3H, s).

【０４３８】[0438]

【実施例１３５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３，５−ジメチルフェニル］アセトアミド（化合物番号
C11.48）融点：151 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．２
３（１Ｈ，ｂｒ．ｓ）；８．００（１Ｈ，
ｄ，Ｊ＝７．６Ｈｚ）；７．９０（１Ｈ，
ｄ，Ｊ＝８．１Ｈｚ）；７．５２−７．３５
（２Ｈ，ｍ）；７．１９（２Ｈ，ｓ）；５．
１４（２Ｈ，ｓ）；２．２６（６Ｈ，ｓ）；
２．１３（３Ｈ，ｓ）． Working Example 135 N- [4- (Benzothiazol-2-ylmethoxy)-
3,5-dimethylphenyl] acetamide (compound number
C11.48) Melting point: 151 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.2
3 (1H, br.s); 8.00 (1H, br.s)
d, J = 7.6 Hz); 7.90 (1H,
d, J = 8.1 Hz); 7.52-7.35.
(2H, m); 7.19 (2H, s);
14 (2H, s); 2.26 (6H, s);
2.13 (3H, s).

【０４３９】[0439]

【実施例１３６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２，３，５−トリメチルフェニル］アセトアミド（化合
物番号Ｃ１１．６３）融点：215 −220 ℃ ＮＭＲスペクトル(270MHz,CDCl₃+CD₃OD), δppm: 7.94
(1H, d, J=9.0 Hz); 7.90 (1H, d, J=9.0 Hz); 7.50-7.
31 (2H, m); 7.02 (1H, s); 5.08 (2H, s); 2.24(3H,
s); 2.20 (3H, s); 2.10 (3H, s); 2.05 (3H, s). Working Example 136 N- [4- (Benzothiazol-2-ylmethoxy)-
2,3,5-trimethylphenyl] acetamide (compound
Compound No. C11.63) Melting point: 215-220 ° C NMR spectrum (270 MHz, CDCl ₃ + CD ₃ OD), δ ppm: 7.94
(1H, d, J = 9.0 Hz); 7.90 (1H, d, J = 9.0 Hz); 7.50-7.
31 (2H, m); 7.02 (1H, s); 5.08 (2H, s); 2.24 (3H,
s); 2.20 (3H, s); 2.10 (3H, s); 2.05 (3H, s).

【０４４０】[0440]

【実施例１３７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２，３，６−トリメチルフェニル］アセトアミド（化合
物番号C11.78）融点：217 −225 ℃ ＮＭＲスペクトル(270MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.1 Hz); 7.92 (1H,d, J=8.1 Hz); 7.56-7.36 (2
H, m); 6.69 (1H, s); 5.43 (2H, s); 2.32-2.16(12H,
m). Working Example 137 N- [4- (Benzothiazol-2-ylmethoxy)-
2,3,6-trimethylphenyl] acetamide (compound
Compound No. C11.78) Melting point: 217-225 ° C NMR spectrum (270 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.1 Hz); 7.92 (1H, d, J = 8.1 Hz); 7.56-7.36 (2
H, m); 6.69 (1H, s); 5.43 (2H, s); 2.32-2.16 (12H,
m).

【０４４１】[0441]

【実施例１３８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３，５−ジメトキシフェニル］アセトアミド（化合物番
号C12.45）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.00 (1H, d
d, J=8.8 & 1.2 Hz); 7.93 (1H, dd, J=6.7 & 1.1 Hz);
7.51-7.35 (2H, m); 7.17 (1H, br.s); 6.82 (2H, s);
5.38 (2H, s); 3.82 (6H, s); 2.17 (3H, s). Working Example 138 N- [4- (Benzothiazol-2-ylmethoxy)-
3,5-Dimethoxyphenyl] acetamide (Compound No.
No. C12.45) Amorphous NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.00 (1H, d
d, J = 8.8 & 1.2 Hz); 7.93 (1H, dd, J = 6.7 & 1.1 Hz);
7.51-7.35 (2H, m); 7.17 (1H, br.s); 6.82 (2H, s);
5.38 (2H, s); 3.82 (6H, s); 2.17 (3H, s).

【０４４２】[0442]

【実施例１３９】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２，５−ジクロロフェニル］アセトアミド（化合物番号
C14.15）融点：188 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.49 (1H,
s); 8.04 (1H, d, J=8.3Hz); 7.93 (1H, d, J=9.2 Hz);
7.38 (3H, m); 7.10 (1H, s); 5.51 (2H, s); 2.23 (3
H, s). Working Example 139 N- [4- (Benzothiazol-2-ylmethoxy)-
2,5-dichlorophenyl] acetamide (compound number
C14.15) Melting point: 188 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.49 (1H,
s); 8.04 (1H, d, J = 8.3Hz); 7.93 (1H, d, J = 9.2 Hz);
7.38 (3H, m); 7.10 (1H, s); 5.51 (2H, s); 2.23 (3
H, s).

【０４４３】[0443]

【実施例１４０】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２，６−ジクロロフェニル］アセトアミド（化合物番号
C14.31）融点：169 −172 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.6 Hz); 7.89 (1H,d, J=8.1 Hz); 7.56-7.42 (2
H, m); 7.13 (1H, d, J=1.8 Hz); 6.97 (1H, d, J=1.8
Hz); 5.47 (2H, s); 2.26 (3H, br.s). Working Example 140 N- [4- (Benzothiazol-2-ylmethoxy)-
2,6-dichlorophenyl] acetamide (compound number
C14.31) Melting point: 169-172 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.6 Hz); 7.89 (1H, d, J = 8.1 Hz); 7.56-7.42 (2
H, m); 7.13 (1H, d, J = 1.8 Hz); 6.97 (1H, d, J = 1.8
Hz); 5.47 (2H, s); 2.26 (3H, br.s).

【０４４４】[0444]

【実施例１４１】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３，５−ジクロロフェニル］アセトアミド（化合物番号
C14.45）融点：173.5 −175 ℃ ＮＭＲスペクトル(200MHz,CDCl₃+CD₃OD), δppm: 7.96
(1H, dd, J=8.7 & 1.5 Hz); 7.89 (1H, dd, J=7.9 & 1.
4 Hz); 7.57 (2H, s); 7.49-7.37 (2H, m); 5.34(2H,
s); 2.08 (3H, s). Working Example 141 N- [4- (Benzothiazol-2-ylmethoxy)-
3,5-dichlorophenyl] acetamide (compound number
C14.45) Melting point: 173.5-175 ° C NMR spectrum (200 MHz, CDCl ₃ + CD ₃ OD), δ ppm: 7.96
(1H, dd, J = 8.7 & 1.5 Hz); 7.89 (1H, dd, J = 7.9 & 1.
4 Hz); 7.57 (2H, s); 7.49-7.37 (2H, m); 5.34 (2H, s)
s); 2.08 (3H, s).

【０４４５】[0445]

【実施例１４２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
３，５−ジブロモフェニル］アセトアミド（化合物番号
C15.37） 198 ℃で分解ＮＭＲスペクトル(270MHz,CDCl₃+CD₃OD), δppm: 7.90-
7.80 (2H, m); 7.70 (2H, s); 7.41-7.25 (2H, m); 5.2
4 (2H, s); 1.98 (3H, s). Working Example 142 N- [4- (benzothiazol-2-ylmethoxy)-
3,5-dibromophenyl] acetamide (compound number
C15.37) Decomposed at 198 ° C NMR spectrum (270MHz, CDCl ₃ + CD ₃ OD), δppm: 7.90-
7.80 (2H, m); 7.70 (2H, s); 7.41-7.25 (2H, m); 5.2
4 (2H, s); 1.98 (3H, s).

【０４４６】[0446]

【実施例１４３】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−クロロ−６−メチルフェニル］カルバマー
ト（化合物番号C16.113 ）融点：184 −187 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.3 Hz); 7.90 (1H,d, J=7.7 Hz); 7.55-7.37 (2
H, m); 6.97 (1H, d, J=2.6 Hz); 6.83 (1H, d, J=2.6
Hz); 6.18 (1H, br.s); 5.43 (2H, s); 3.75 (3H, br.
s); 2.28 (3H, s). Working Example 143: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-chloro-6-methylphenyl] carbamer
(Compound number C16.113) melting point: 184-187 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.3 Hz); 7.90 (1H, d, J = 7.7 Hz); 7.55-7.37 (2
H, m); 6.97 (1H, d, J = 2.6 Hz); 6.83 (1H, d, J = 2.6
Hz); 6.18 (1H, br.s); 5.43 (2H, s); 3.75 (3H, br.
s); 2.28 (3H, s).

【０４４７】[0447]

【実施例１４４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
５−イソプロピル−２−メチルフェニル］アセトアミド
（化合物番号C18.118 ）融点：153 −156 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=8.6 Hz); 7.92 (1H,d, J=8.3 Hz); 7.51-7.41 (3
H, m); 6.84 (1H, d, J=8.3 Hz); 6.76 (2H, s);5.46
(2H, s); 3.42 (1H, q, J=6.7 Hz); 2.21 (3H, s); 2.1
9 (3H, s); 1.28 (6H, d, J=6.8 Hz). Working Example 144 N- [4- (benzothiazol-2-ylmethoxy)-
5-isopropyl-2-methylphenyl] acetamide
(Compound No. C18.118) Melting point: 153-156 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 8.6 Hz); 7.92 (1H, d, J = 8.3 Hz); 7.51-7.41 (3
H, m); 6.84 (1H, d, J = 8.3 Hz); 6.76 (2H, s); 5.46
(2H, s); 3.42 (1H, q, J = 6.7 Hz); 2.21 (3H, s); 2.1
9 (3H, s); 1.28 (6H, d, J = 6.8 Hz).

【０４４８】[0448]

【実施例１４５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−クロロ−６−メトキシカルボニルフェニル］アセト
アミド（化合物番号C18.130 ）融点：141 −143 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07 (1H, b
r.s); 8.04 (1H, d, J=8.5 Hz); 7.91 (1H, d, J=8.5 H
z); 7.37-7.57 (3H, m); 7.31 (1H, s); 5.49 (2H, s);
3.89 (3H, s); 2.20 (3H, s). Working Example 145 N- [4- (Benzothiazol-2-ylmethoxy)-
2-chloro-6-methoxycarbonylphenyl] aceto
Amide (Compound No. C18.130) Melting point: 141-143 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07 (1H, b
rs); 8.04 (1H, d, J = 8.5 Hz); 7.91 (1H, d, J = 8.5 H
z); 7.37-7.57 (3H, m); 7.31 (1H, s); 5.49 (2H, s);
3.89 (3H, s); 2.20 (3H, s).

【０４４９】[0449]

【実施例１４６】Ｎ−［４−（５−メトキシベンゾオキサゾール−２−イ
ルメトキシ）−２−メチルフェニル］アセトアミド（化
合物番号G1.35 ）融点：173 −177 ℃ ＮＭＲスペクトル(200MHz,CDCl₃)δppm: 7.56-7.51 (1
H, m); 7.43 (1H, d, J=9.0 Hz); 7.22 (1H, d, J=2.6
Hz); 6.99-6.82 (4H, m); 5.26 (2H, s); 3.86 (3H,
s); 2.24 (3H, s); 2.19 (3H, s).Working Example 146 N- [4- (5-methoxybenzoxazol-2-i
Rumethoxy) -2-methylphenyl] acetamide
Compound No. G1.35) Melting point: 173-177 ° C. NMR spectrum (200 MHz, CDCl ₃ ) δ ppm: 7.56-7.51 (1
H, m); 7.43 (1H, d, J = 9.0 Hz); 7.22 (1H, d, J = 2.6
Hz); 6.99-6.82 (4H, m); 5.26 (2H, s); 3.86 (3H,
s); 2.24 (3H, s); 2.19 (3H, s).

【０４５０】[0450]

【実施例１４７】メチルＮ−［４−（５−メトキシベンゾオキサゾール
−２−イルメトキシ）−２−メチルフェニル］カルバマ
ート（化合物番号G1.36 ）融点：160 −162 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.55-7.49
(1H, br.m); 7.43 (1H, d, J=8.7 Hz); 7.22 (1H, d, J
=2.4 Hz); 6.99-6.88 (3H, m); 6.19 (1H, br.s);5.26
(2H, s); 3.86 (3H, s); 3.76 (3H, s); 2.23 (3H, s).Working Example 147 Methyl N- [4- (5-methoxybenzoxazole)
-2-ylmethoxy) -2-methylphenyl] carbama
Melting point: 160-162 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.55-7.49
(1H, br.m); 7.43 (1H, d, J = 8.7 Hz); 7.22 (1H, d, J
= 2.4 Hz); 6.99-6.88 (3H, m); 6.19 (1H, br.s); 5.26
(2H, s); 3.86 (3H, s); 3.76 (3H, s); 2.23 (3H, s).

【０４５１】[0451]

【実施例１４８】Ｎ−［４−（５−メチルベンゾチアゾール−２−イルメ
トキシ）フェニル］アセトアミド（化合物番号F1.11 ）融点：211 −213 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.82 (1H,
s); 7.76 (1H, d, J=8.3Hz); 7.44-7.38 (2H, m); 7.26
-7.21 (1H, m); 7.09-7.03 (1H, m); 7.01-6.95(2H,
m); 5.45 (2H, s); 2.51 (3H, s); 2.15 (3H, s). Working Example 148 N- [4- (5-methylbenzothiazol-2-ylmethine)
Toxi) phenyl] acetamide (Compound No. F1.11) Melting point: 211-213 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.82 (1H,
s); 7.76 (1H, d, J = 8.3Hz); 7.44-7.38 (2H, m); 7.26
-7.21 (1H, m); 7.09-7.03 (1H, m); 7.01-6.95 (2H,
m); 5.45 (2H, s); 2.51 (3H, s); 2.15 (3H, s).

【０４５２】[0452]

【実施例１４９】Ｎ−［４−（７−メチルベンゾチアゾール−２−イルメ
トキシ）フェニル］アセトアミド（化合物番号F1.31 ）融点：164 −166 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.87 (1H,
d, J=7.9 Hz); 7.45-7.38(3H, m); 7.20 (1H, d, J=7.0
Hz); 7.07-6.98 (3H, m); 5.47 (2H, s); 2.57(3H,
s); 2.16 (3H, s). Working Example 149 N- [4- (7-Methylbenzothiazol-2-ylmethine)
Toxi) phenyl] acetamide (Compound No. F1.31) Melting point: 164 ° -166 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.87 (1H,
d, J = 7.9 Hz); 7.45-7.38 (3H, m); 7.20 (1H, d, J = 7.0
Hz); 7.07-6.98 (3H, m); 5.47 (2H, s); 2.57 (3H,
s); 2.16 (3H, s).

【０４５３】[0453]

【実施例１５０】Ｎ−［４−（７−メトキシベンゾチアゾール−２−イル
メトキシ）フェニル］アセトアミド（化合物番号F3.29
）融点：163 −164 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.65 (1H,
d, J=8.4 Hz); 7.48-7.39(3H, m); 7.02-6.82 (4H, m);
5.45 (2H, s); 3.98 (3H, s); 2.16 (3H, s).Working Example 150 N- [4- (7-methoxybenzothiazol-2-yl)
Methoxy) phenyl] acetamide (Compound No.F3.29
) Mp: 163 -164 ° C. NMR spectrum _{(200MHz, CDCl 3), δppm} : 7.65 (1H,
d, J = 8.4 Hz); 7.48-7.39 (3H, m); 7.02-6.82 (4H, m);
5.45 (2H, s); 3.98 (3H, s); 2.16 (3H, s).

【０４５４】[0454]

【実施例１５１】Ｎ−［４−（４−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］アセトアミド（化合物番号F4.1）融点：156 −158 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.66 (1H,
d, J=8.0 Hz); 7.45-7.32(3H, m); 7.25-7.16 (1H, m);
7.08-7.01 (1H, m); 6.98-6.97 (2H, m); 5.49(2H,
s); 2.16 (3H, s).Working Example 151 N- [4- (4-Fluorobenzothiazol-2-yl)
Methoxy) phenyl] acetamide (Compound No. F4.1) Melting point: 156-158 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.66 (1H,
d, J = 8.0 Hz); 7.45-7.32 (3H, m); 7.25-7.16 (1H, m);
7.08-7.01 (1H, m); 6.98-6.97 (2H, m); 5.49 (2H,
s); 2.16 (3H, s).

【０４５５】[0455]

【実施例１５２】Ｎ−［４−（５−クロロベンゾチアゾール−２−イルメ
トキシ）フェニル］アセトアミド（化合物番号F4.59 ）融点：230 −232 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.01 (1H,
d, J=2.0 Hz); 7.81 (1H,d, J=8.8 Hz); 7.45-7.36 (3
H, m); 7.09-7.08 (1H, m); 7.01-6.95 (2H, m);5.45
(2H, s); 2.16 (3H, s). Working Example 152 N- [4- (5-chlorobenzothiazol-2-ylmethine)
Toxi) phenyl] acetamide (Compound No. F4.59) Melting point: 230-232 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.01 (1H,
d, J = 2.0 Hz); 7.81 (1H, d, J = 8.8 Hz); 7.45-7.36 (3
H, m); 7.09-7.08 (1H, m); 7.01-6.95 (2H, m); 5.45
(2H, s); 2.16 (3H, s).

【０４５６】[0456]

【実施例１５３】Ｎ−［４−（６−クロロベンゾチアゾール−２−イルメ
トキシ）フェニル］アセトアミド（化合物番号F4.69 ）融点：218 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．９
３（１Ｈ，ｄ，Ｊ＝８．６Ｈｚ）；７．８８
（１Ｈ，ｄ，Ｊ＝２．１Ｈｚ）；７．４９−
７．４１（３Ｈ，ｍ）；７．０１−６．９７
（３Ｈ，ｍ）；５．４４（２Ｈ，ｓ）；２．
１６（３Ｈ，ｓ）．Example 153 N- [4- (6-chlorobenzothiazol-2-ylmethine)
Toxy) phenyl] acetamide (Compound No. F4.69) Melting point: 218 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.9
3. (1H, d, J = 8.6 Hz); 7.88
(1H, d, J = 2.1 Hz); 7.49-
7.41 (3H, m); 7.01-6.97
(3H, m); 5.44 (2H, s);
16 (3H, s).

【０４５７】[0457]

【実施例１５４】Ｎ−［４−（７−クロロベンゾチアゾール−２−イルメ
トキシ）フェニル］アセトアミド（化合物番号Ｆ４．７
９）融点：172 −175 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.94-7.90
(1H, m); 7.50-7.41 (4H,m); 7.08-6.98 (3H, m); 5.45
(2H, s); 2.16 (3H, s).Example 154 N- [4- (7-chlorobenzothiazol-2-ylmethine)
Toxi) phenyl] acetamide (Compound No. F4.7)
9) Melting point: 172-175 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.94-7.90
(1H, m); 7.50-7.41 (4H, m); 7.08-6.98 (3H, m); 5.45
(2H, s); 2.16 (3H, s).

【０４５８】[0458]

【実施例１５５】Ｎ−［４−（６−ブロモベンゾチアゾール−２−イルメ
トキシ）フェニル］アセトアミド（化合物番号F4.103）融点：218 −221 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04-8.03
(1H, m); 7.78 (1H, d, J=8.8 Hz); 7.62-7.61 (1H,
m); 7.45-7.41 (2H, m); 7.01-6.97 (3H, m); 5.43(2H,
s); 2.16 (3H, s).Example 155 N- [4- (6-bromobenzothiazol-2-ylmethine)
Toxi) phenyl] acetamide (Compound No. F4.103) Melting point: 218-221 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04-8.03
(1H, m); 7.78 (1H, d, J = 8.8 Hz); 7.62-7.61 (1H,
m); 7.45-7.41 (2H, m); 7.01-6.97 (3H, m); 5.43 (2H,
s); 2.16 (3H, s).

【０４５９】[0459]

【実施例１５６】Ｎ−［４−（４，５−ジフルオロベンゾチアゾール−２
−イルメトキシ）フェニル］アセトアミド（化合物番号
F7.34 ）融点：178 −180 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.62-7.54
(1H, m); 7.46-7.41 (2H,m); 7.35-7.22 (1H, m); 7.08
-6.97 (3H, m); 5.48 (2H, s); 2.16 (3H, s). Working Example 156 N- [4- (4,5-difluorobenzothiazole-2)
-Ylmethoxy) phenyl] acetamide (compound number
F7.34) Melting point: 178-180 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.62-7.54
(1H, m); 7.46-7.41 (2H, m); 7.35-7.22 (1H, m); 7.08
-6.97 (3H, m); 5.48 (2H, s); 2.16 (3H, s).

【０４６０】[0460]

【実施例１５７】Ｎ−［４−（４，６−ジフルオロベンゾチアゾール−２
−イルメトキシ）フェニル］アセトアミド（化合物番号
F7.39 ）融点：198 −200 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．４
５−７．３６（３Ｈ，ｍ）；７．０７−６．９６
（４Ｈ，ｍ）；５．４５（２Ｈ，ｓ）；２．
１６（３Ｈ，ｓ）． Working Example 157 N- [4- (4,6-difluorobenzothiazole-2)
-Ylmethoxy) phenyl] acetamide (compound number
F7.39) Melting point: 198-200 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.4
5-7.36 (3H, m); 7.07-6.96
(4H, m); 5.45 (2H, s);
16 (3H, s).

【０４６１】[0461]

【実施例１５８】Ｎ−［４−（５，６−ジフルオロベンゾチアゾール−２
−イルメトキシ）フェニル］アセトアミド（化合物番号
Ｆ７．４５）融点：212 −214 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.85-7.76
(1H, m); 7.71-7.62 (1H,m); 7.45-7.41 (2H, m); 7.01
-6.96 (3H, m); 5.43 (2H, s); 2.16 (3H, s). Working Example 158 N- [4- (5,6-difluorobenzothiazole-2)
-Ylmethoxy) phenyl] acetamide (compound number
F7.45) Melting point: 212-214 ° C NMR spectrum (200MHz, CDCl ₃ ), δ ppm: 7.85-7.76
(1H, m); 7.71-7.62 (1H, m); 7.45-7.41 (2H, m); 7.01
-6.96 (3H, m); 5.43 (2H, s); 2.16 (3H, s).

【０４６２】[0462]

【実施例１５９】Ｎ−［４−（５−フルオロ−６−メチルベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号F7.92 ）融点：231 −234 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.67 (1H,
s); 7.63 (1H, d, J=4.7Hz); 7.57 (1H, d, J=8.9 Hz);
7.42 (1H, d, J=5.1 Hz); 7.06 (1H, br.s); 6.98 (1
H, d, J=9.1 Hz); 6.99 (1H, d, J=4.3 Hz); 5.43 (2H,
s); 2.41 (3H, d,J=2.2 Hz); 2.16 (3H, s).Working Example 159 N- [4- (5-Fluoro-6-methylbenzothiazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product number F7.92) Melting point: 231-234 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.67 (1H,
s); 7.63 (1H, d, J = 4.7Hz); 7.57 (1H, d, J = 8.9 Hz);
7.42 (1H, d, J = 5.1 Hz); 7.06 (1H, br.s); 6.98 (1
H, d, J = 9.1 Hz); 6.99 (1H, d, J = 4.3 Hz); 5.43 (2H,
s); 2.41 (3H, d, J = 2.2 Hz); 2.16 (3H, s).

【０４６３】[0463]

【実施例１６０】Ｎ−［４−（６−フルオロ−５−メチルベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号F7.99 ）融点：231 −234 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.81 (1H,
d, J=6.8 Hz); 7.53-7.34(3H, m); 7.01-6.96 (3H, m);
5.42 (2H, s); 2.42 (3H, d, J=2.2 Hz); 2.16(3H,
s).Working Example 160 N- [4- (6-Fluoro-5-methylbenzothiazolate)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product number F7.99) Melting point: 231-234 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.81 (1H,
d, J = 6.8 Hz); 7.53-7.34 (3H, m); 7.01-6.96 (3H, m);
5.42 (2H, s); 2.42 (3H, d, J = 2.2 Hz); 2.16 (3H,
s).

【０４６４】[0464]

【実施例１６１】Ｎ−［４−（５−クロロ−６−メチルベンゾチアゾール
−２−イルメトキシ）フェニル］アセトアミド（化合物
番号F7.120）融点：236 −239 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.01 (1H,
s); 7.73 (1H, s); 7.42(2H, d, J=8.9 Hz); 7.05-6.96
(3H, m); 5.43 (2H, s); 2.50 (3H, s); 2.16 (3H,
s).Working Example 161 N- [4- (5-Chloro-6-methylbenzothiazole)
-2-ylmethoxy) phenyl] acetamide (compound
No. F7.120) melting point: 236-239 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.01 (1H,
s); 7.73 (1H, s); 7.42 (2H, d, J = 8.9 Hz); 7.05-6.96
(3H, m); 5.43 (2H, s); 2.50 (3H, s); 2.16 (3H,
s).

【０４６５】[0465]

【実施例１６２】Ｎ−［４−（５−クロロ−６−メトキシベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号F7.147）融点：222 −225 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.01 (1H,
s); 7.43-7.35 (2H, m);7.06-6.96 (3H, m); 5.41 (2H,
s); 3.96 (3H, s); 2.15 (3H, s).Working Example 162 N- [4- (5-Chloro-6-methoxybenzothiazolate)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Article No. F7.147) Melting point: 222-225 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.01 (1H,
s); 7.43-7.35 (2H, m); 7.06-6.96 (3H, m); 5.41 (2H,
s); 3.96 (3H, s); 2.15 (3H, s).

【０４６６】[0466]

【実施例１６３】Ｎ−［４−（５−クロロ−６−フルオロベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号F7.169）融点：227 −229 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=6.7 Hz); 7.66 (1H,d, J=8.3 Hz); 7.45-7.41 (2
H, m); 7.06-6.96 (3H, m); 5.43 (2H, s); 2.16(3H,
s).Working Example 163 N- [4- (5-chloro-6-fluorobenzothiazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Article No. F7.169) Melting point: 227-229 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
d, J = 6.7 Hz); 7.66 (1H, d, J = 8.3 Hz); 7.45-7.41 (2
H, m); 7.06-6.96 (3H, m); 5.43 (2H, s); 2.16 (3H,
s).

【０４６７】[0467]

【実施例１６４】Ｎ−［４−（７−クロロ−６−フルオロベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号F7.173）融点：182 −185 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.87 (1H,
m); 7.46-7.42 (2H, m);7.35 (1H, d, J=9.1 Hz); 7.09
-6.97 (3H, m); 5.43 (2H, s); 2.16 (3H, s).Working Example 164 N- [4- (7-Chloro-6-fluorobenzothiazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Article number F7.173) Melting point: 182-185 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.87 (1H,
m); 7.46-7.42 (2H, m); 7.35 (1H, d, J = 9.1 Hz); 7.09
-6.97 (3H, m); 5.43 (2H, s); 2.16 (3H, s).

【０４６８】[0468]

【実施例１６５】Ｎ−［２−メチル−４−（５−メチルベンゾチアゾール
−２−イルメトキシ）フェニル］アセトアミド（化合物
番号G1.6）融点：206 −208 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.83 (1H,
s); 7.76 (1H, d, J=8.7Hz); 7.53 (1H, d, J=8.9 Hz);
7.27-7.21 (1H, m); 6.91-6.84 (3H, m); 5.44(2H,
s); 2.52 (3H, s); 2.24 (3H, s); 2.19 (3H, s).Working Example 165 N- [2-Methyl-4- (5-methylbenzothiazole)
-2-ylmethoxy) phenyl] acetamide (compound
No. G1.6) melting point: 206-208 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.83 (1H,
s); 7.76 (1H, d, J = 8.7 Hz); 7.53 (1H, d, J = 8.9 Hz);
7.27-7.21 (1H, m); 6.91-6.84 (3H, m); 5.44 (2H, m
s); 2.52 (3H, s); 2.24 (3H, s); 2.19 (3H, s).

【０４６９】[0469]

【実施例１６６】Ｎ−［２−メチル−４−（６−メチルベンゾチアゾール
−２−イルメトキシ）フェニル］アセトアミド（化合物
番号G1.11 ）融点：192 −193 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.90 (1H,
d, J=8.4 Hz); 7.68 (1H,s); 7.53 (1H, d, J=9.1 Hz);
7.30 (1H, d, J=8.8 Hz); 6.89-6.81 (3H, m);5.43 (2
H, s); 2.49 (3H, s); 2.23 (3H, s); 2.18 (3H, s).Working Example 166 N- [2-Methyl-4- (6-methylbenzothiazole)
-2-ylmethoxy) phenyl] acetamide (compound
No. G1.11) melting point: 192-193 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.90 (1H,
d, J = 8.4 Hz); 7.68 (1H, s); 7.53 (1H, d, J = 9.1 Hz);
7.30 (1H, d, J = 8.8 Hz); 6.89-6.81 (3H, m); 5.43 (2
H, s); 2.49 (3H, s); 2.23 (3H, s); 2.18 (3H, s).

【０４７０】[0470]

【実施例１６７】Ｎ−［４−（５−メトキシベンゾチアゾール−２−イル
メトキシ）−２−メチルフェニル］アセトアミド（化合
物番号G1.32 ）融点：203 −204 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 9.23 (1H,
s); 7.99 (1H, d, J=8.8Hz); 7.58 (1H, d, J=2.4 Hz);
7.26 (1H, d, J=8.8 Hz); 7.12 (1H, dd, J=8.8& 2.5
Hz); 7.10 (1H, d, J=2.5 Hz); 6.92 (1H, br.d, J=8.8
Hz); 5.56 (1H,s); 3.87 (3H, s); 2.18 (3H, s); 2.0
3 (3H, s).Working Example 167 N- [4- (5-methoxybenzothiazol-2-yl)
Methoxy) -2-methylphenyl] acetamide (compound
Product number G1.32) Melting point: 203-204 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 9.23 (1H,
s); 7.99 (1H, d, J = 8.8Hz); 7.58 (1H, d, J = 2.4 Hz);
7.26 (1H, d, J = 8.8 Hz); 7.12 (1H, dd, J = 8.8 & 2.5
Hz); 7.10 (1H, d, J = 2.5 Hz); 6.92 (1H, br.d, J = 8.8
Hz); 5.56 (1H, s); 3.87 (3H, s); 2.18 (3H, s); 2.0
3 (3H, s).

【０４７１】[0471]

【実施例１６８】Ｎ−［４−（６−メトキシベンゾチアゾール−２−イル
メトキシ）−２−メチルフェニル］アセトアミド（化合
物番号G1.37 ）融点：159 −162 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．９
０（１Ｈ，ｄ，Ｊ＝９．１Ｈｚ）；７．５５
−７．５１（１Ｈ，ｍ）；７．３４（１Ｈ，
ｄ，Ｊ＝２．６Ｈｚ）；７．１２−７．０６
（１Ｈ，ｍ）；６．８９−６．８６（３Ｈ，
ｍ）；５．４１（２Ｈ，ｓ）；３．８８（３
Ｈ，ｓ）；２．２４（３Ｈ，ｓ）；２．１９
（３Ｈ，ｓ）．Working Example 168 N- [4- (6-Methoxybenzothiazol-2-yl)
Methoxy) -2-methylphenyl] acetamide (compound
Compound No. G1.37) Melting point: 159-162 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.9
0 (1H, d, J = 9.1 Hz); 7.55
-7.51 (1H, m); 7.34 (1H,
d, J = 2.6 Hz); 7.12-7.06
(1H, m); 6.89-6.86 (3H,
m); 5.41 (2H, s); 3.88 (3
H, s); 2.24 (3H, s); 2.19
(3H, s).

【０４７２】[0472]

【実施例１６９】Ｎ−［４−（４−フルオロベンゾチアゾール−２−イル
メトキシ）−２−メチルフェニル］アセトアミド（化合
物番号Ｇ１．５０）融点：174 −176 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.65-7.64
(2H, m); 7.29-7.24 (2H,m); 6.89-6.86 (3H, m); 5.48
(2H, s); 2.25 (3H, s); 2.19 (3H, s).Working Example 169 N- [4- (4-Fluorobenzothiazol-2-yl)
Methoxy) -2-methylphenyl] acetamide (compound
Compound No. G1.50) Melting point: 174-176 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.65-7.64
(2H, m); 7.29-7.24 (2H, m); 6.89-6.86 (3H, m); 5.48
(2H, s); 2.25 (3H, s); 2.19 (3H, s).

【０４７３】[0473]

【実施例１７０】Ｎ−［４−（６−フルオロベンゾチアゾール−２−イル
メトキシ）−２−メチルフェニル］アセトアミド（化合
物番号G1.60 ）融点：204 −205 ℃ ＮＭＲスペクトル(200MHz, DMSO-d₆）, δppm: 9.22 (1
H, s); 8.09-8.02 (2H,m); 7.42 (1H, td, J=9.2 & 2.8
Hz); 7.25 (1H, d, J=8.6 Hz); 6.99-6.86 (2H, m);
5.56 (2H, s); 2.17 (3H, s); 2.02 (3H, s).Working Example 170 N- [4- (6-Fluorobenzothiazol-2-yl)
Methoxy) -2-methylphenyl] acetamide (compound
Things No. G1.60) mp: 204 -205 ° C. NMR spectrum _{(200MHz, DMSO-d 6)} , δppm: 9.22 (1
H, s); 8.09-8.02 (2H, m); 7.42 (1H, td, J = 9.2 & 2.8
Hz); 7.25 (1H, d, J = 8.6 Hz); 6.99-6.86 (2H, m);
5.56 (2H, s); 2.17 (3H, s); 2.02 (3H, s).

【０４７４】[0474]

【実施例１７１】Ｎ−［４−（５−クロロベンゾチアゾール−２−イルメ
トキシ）−２−メチルフェニル］アセトアミド（化合物
番号G1.72 ）融点：213 −214 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.08 (1H,
d, J=1.8 Hz); 7.81 (1H,d, J=8.6 Hz); 7.55 (1H, d,
J=8.6 Hz); 7.38 (1H, dd, J=8.7 & 2.1 Hz); 6.89 (1
H, s); 6.87 (1H, d, J=7.7 Hz); 6.84 (1H, br.s); 5.
44 (2H, s); 2.24(3H, s); 2.19 (3H, s).Example 171 N- [4- (5-chlorobenzothiazol-2-ylmethine)
Toxi) -2-methylphenyl] acetamide (compound
No. G1.72) melting point: 213-214 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.08 (1H,
d, J = 1.8 Hz); 7.81 (1H, d, J = 8.6 Hz); 7.55 (1H, d,
J = 8.6 Hz); 7.38 (1H, dd, J = 8.7 & 2.1 Hz); 6.89 (1
H, s); 6.87 (1H, d, J = 7.7 Hz); 6.84 (1H, br.s); 5.
44 (2H, s); 2.24 (3H, s); 2.19 (3H, s).

【０４７５】[0475]

【実施例１７２】Ｎ−［２−メチル−４−（４−トリフルオロメチルベン
ゾチアゾール−２−イルメトキシ）フェニル］アセトア
ミド（化合物番号G1.87 ）融点：185 −186 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.10 (1H,
d, J=8.0 Hz); 7.80 (1H,d, J=8.0 Hz); 7.55 (1H, d,
J=8.8 Hz); 7.48 (1H, t, J=8.0 Hz); 6.96-6.84(3H,
m); 5.52 (2H, s); 2.24 (3H, s); 2.19 (3H, s).Working Example 172 N- [2-Methyl-4- (4-trifluoromethylbenz)
Zothiazol-2-ylmethoxy) phenyl] acetoa
Mide (Compound No. G1.87) Melting point: 185-186 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.10 (1H,
d, J = 8.0 Hz); 7.80 (1H, d, J = 8.0 Hz); 7.55 (1H, d,
J = 8.8 Hz); 7.48 (1H, t, J = 8.0 Hz); 6.96-6.84 (3H,
m); 5.52 (2H, s); 2.24 (3H, s); 2.19 (3H, s).

【０４７６】[0476]

【実施例１７３】Ｎ−［２−メチル−４−（６−トリフルオロメチルベン
ゾチアゾール−２−イルメトキシ）フェニル］アセトア
ミド化合物番号G1.97 ）融点：203 −205 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.20-8.09
(2H, m); 7.77-7.72 (1H,m); 7.55-7.52 (1H, m); 6.90
-6.80 (3H, m); 5.48 (2H, s); 2.25 (3H, s); 2.19 (3
H, m s).Working Example 173 N- [2-methyl-4- (6-trifluoromethylben
Zothiazol-2-ylmethoxy) phenyl] acetoa
Mido compound number G1.97) Melting point: 203-205 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.20-8.09
(2H, m); 7.77-7.72 (1H, m); 7.55-7.52 (1H, m); 6.90
-6.80 (3H, m); 5.48 (2H, s); 2.25 (3H, s); 2.19 (3
H, ms).

【０４７７】[0477]

【実施例１７４】Ｎ−［４−（５，６−ジフルオロベンゾチアゾール−２
−イルメトキシ）−２−メチルフェニル］アセトアミド
（化合物番号G2.42 ）融点：219 −222 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.84-7.53
(3H, m); 6.88-6.83 (3H,m); 5.42 (2H, s); 2.24 (3H,
s); 2.19 (3H, s). Working Example 174 N- [4- (5,6-difluorobenzothiazole-2)
-Ylmethoxy) -2-methylphenyl] acetamide
(Compound No. G2.42) Melting point: 219-222 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.84-7.53
(3H, m); 6.88-6.83 (3H, m); 5.42 (2H, s); 2.24 (3H,
s); 2.19 (3H, s).

【０４７８】[0478]

【実施例１７５】Ｎ−［４−（５−フルオロ−６−メチルベンゾチアゾー
ル−２−イルメトキシ）−２−メチルフェニル］アセト
アミド（化合物番号G2.86 ）融点：222 −225 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.67 (1H,
s); 7.64 (1H, d, J=4.8Hz); 7.54 (1H, d, J=8.8 Hz);
6.88 (2H, s); 6.85-6.82 (1H, m); 5.42 (2H,s); 2.4
1 (2H, d, J=1.8 Hz); 2.24 (3H, s); 2.19 (3H, s).Working Example 175 N- [4- (5-Fluoro-6-methylbenzothiazole)
Ru-2-ylmethoxy) -2-methylphenyl] aceto
Amide (Compound No. G2.86) Melting point: 222-225 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.67 (1H,
s); 7.64 (1H, d, J = 4.8Hz); 7.54 (1H, d, J = 8.8 Hz);
6.88 (2H, s); 6.85-6.82 (1H, m); 5.42 (2H, s); 2.4
1 (2H, d, J = 1.8 Hz); 2.24 (3H, s); 2.19 (3H, s).

【０４７９】[0479]

【実施例１７６】Ｎ−［４−（６−フルオロ- ７−メチルベンゾチアゾー
ル−２−イルメトキシ）−２−メチルフェニル］アセト
アミド（化合物番号G2.97 ）融点：191 −195 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.80 (1H,
m); 7.54 (1H, d, J=8.5Hz); 7.19 (1H, d, J=8.9 Hz);
6.89 (2H, s); 6.86-6.81 (1H, m); 5.42 (2H,s); 2.4
7 (3H, d, J=1.6 Hz); 2.24 (3H, s); 2.19 (3H, s).Working Example 176 N- [4- (6-Fluoro-7-methylbenzothiazole)
Ru-2-ylmethoxy) -2-methylphenyl] aceto
Amide (Compound No. G2.97) Melting point: 191 ° -195 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.80 (1H,
m); 7.54 (1H, d, J = 8.5Hz); 7.19 (1H, d, J = 8.9 Hz);
6.89 (2H, s); 6.86-6.81 (1H, m); 5.42 (2H, s); 2.4
7 (3H, d, J = 1.6 Hz); 2.24 (3H, s); 2.19 (3H, s).

【０４８０】[0480]

【実施例１７７】Ｎ−［４−（５−クロロ−６−メチルベンゾチアゾール
−２−イルメトキシ）−２−メチルフェニル］アセトア
ミド（化合物番号G2.115）融点：249 −251 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.01 (1H,
s); 7.73 (1H, s); 7.54(1H, d, J=9.1 Hz); 6.88-6.81
(3H, m); 5.42 (2H, s); 2.50 (3H, s); 2.24 (3H,
s); 2.19 (3H, s).Working Example 177 N- [4- (5-Chloro-6-methylbenzothiazole)
-2-ylmethoxy) -2-methylphenyl] acetoa
Mide (Compound No. G2.115) Melting point: 249-251 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.01 (1H,
s); 7.73 (1H, s); 7.54 (1H, d, J = 9.1 Hz); 6.88-6.81
(3H, m); 5.42 (2H, s); 2.50 (3H, s); 2.24 (3H,
s); 2.19 (3H, s).

【０４８１】[0481]

【実施例１７８】Ｎ−［４−（５−クロロ−６−メトキシベンゾチアゾー
ル−２−イルメトキシ）−２−メチルフェニル］アセト
アミド（化合物番号G2.137）融点：228 −230 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.02 (1H,
s); 7.54 (1H, d, J=8.9Hz); 7.36 (1H, s); 6.88 (2H,
s); 6.85-6.81 (1H, m); 5.40 (2H, s); 3.97 (3H,
s); 2.24 (3H, s); 2.19 (3H, s).Working Example 178 N- [4- (5-chloro-6-methoxybenzothiazole)
Ru-2-ylmethoxy) -2-methylphenyl] aceto
Amide (Compound No. G2.137) Melting point: 228-230 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.02 (1H,
s); 7.54 (1H, d, J = 8.9Hz); 7.36 (1H, s); 6.88 (2H,
s); 6.85-6.81 (1H, m); 5.40 (2H, s); 3.97 (3H,
s); 2.24 (3H, s); 2.19 (3H, s).

【０４８２】[0482]

【実施例１７９】Ｎ−［４−（５−クロロ−６−フルオロベンゾチアゾー
ル−２−イルメトキシ）−２−メチルフェニル］アセト
アミド（化合物番号G2.148）融点：242 −245 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
５（１Ｈ，ｄ，Ｊ＝６．６Ｈｚ）；７．６６
（１Ｈ，ｄ，Ｊ＝８．１Ｈｚ）；７．５５
（１Ｈ，ｄ，Ｊ＝８．６Ｈｚ）；６．８８
（２Ｈ，ｓ）；６．８４−６．８３（１Ｈ，
ｍ）；５．４２（２Ｈ，ｓ）；２．２５（３
Ｈ，ｓ）；２．１９（３Ｈ，ｓ）．Working Example 179 N- [4- (5-chloro-6-fluorobenzothiazole)
Ru-2-ylmethoxy) -2-methylphenyl] aceto
Amide (Compound No. G2.148) Melting point: 242 ° -245 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
5. (1H, d, J = 6.6 Hz); 7.66
(1H, d, J = 8.1 Hz); 7.55
(1H, d, J = 8.6 Hz); 6.88
(2H, s); 6.84-6.83 (1H,
m); 5.42 (2H, s); 2.25 (3
H, s); 2.19 (3H, s).

【０４８３】[0483]

【実施例１８０】Ｎ−［４−（７−クロロ−６−フルオロベンゾチアゾー
ル−２−イルメトキシ）−２−メチルフェニル］アセト
アミド（化合物番号Ｇ２．１６６）融点：218 −220 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.87 (1H,
m); 7.59-7.54 (1H, m);7.35 (1H, d, J=9.1 Hz); 6.89
(2H, s); 6.88-6.82 (1H, m); 5.42 (2H, s); 2.25 (3
H, s); 2.19 (3H, s).Working Example 180 N- [4- (7-Chloro-6-fluorobenzothiazole)
Ru-2-ylmethoxy) -2-methylphenyl] aceto
Amide (Compound No. G2.166) Melting point: 218-220 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.87 (1H,
m); 7.59-7.54 (1H, m); 7.35 (1H, d, J = 9.1 Hz); 6.89
(2H, s); 6.88-6.82 (1H, m); 5.42 (2H, s); 2.25 (3
H, s); 2.19 (3H, s).

【０４８４】[0484]

【実施例１８１】Ｎ−［２−エチル−４−（５−メチルベンゾチアゾール
−２−イルメトキシ）フェニル］アセトアミド（化合物
番号G5.3）融点：218 −221 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.83-7.75
(3H, m); 7.53-7.50 (1H,m); 6.92-6.90 (3H, m); 5.45
(2H, s); 2.60-2.52 (2H, m); 2.59 (3H, s); 2.19 (3
H, s); 1.22 (3H, t, J=7.2 Hz).Working Example 181 N- [2-ethyl-4- (5-methylbenzothiazole)
-2-ylmethoxy) phenyl] acetamide (compound
No. G5.3) Melting point: 218-221 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.83-7.75
(3H, m); 7.53-7.50 (1H, m); 6.92-6.90 (3H, m); 5.45
(2H, s); 2.60-2.52 (2H, m); 2.59 (3H, s); 2.19 (3
H, s); 1.22 (3H, t, J = 7.2 Hz).

【０４８５】[0485]

【実施例１８２】Ｎ−［２−エチル−４−（６−メチルベンゾチアゾール
−２−イルメトキシ）フェニル］アセトアミド（化合物
番号G5.6）融点：198 −200 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.90 (1H,
d, J=9.2 Hz); 7.69 (1H,s); 7.52 (1H, d, J=8.6 Hz);
7.33-7.28 (1H, m); 6.93-6.82 (3H, m); 5.44(2H,
s); 2.57 (2H, q, J=7.8 Hz); 2.50 (3H, s); 1.22 (3
H, t, J=7.6 Hz).Working Example 182 N- [2-ethyl-4- (6-methylbenzothiazole)
-2-ylmethoxy) phenyl] acetamide (compound
No. G5.6) Melting point: 198-200 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.90 (1H,
d, J = 9.2 Hz); 7.69 (1H, s); 7.52 (1H, d, J = 8.6 Hz);
7.33-7.28 (1H, m); 6.93-6.82 (3H, m); 5.44 (2H, m
s); 2.57 (2H, q, J = 7.8 Hz); 2.50 (3H, s); 1.22 (3
(H, t, J = 7.6 Hz).

【０４８６】[0486]

【実施例１８３】Ｎ−［２−エチル−４−（５−メトキシベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号G5.17 ）融点：169 −172 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.74 (1H,
d, J=8.6 Hz); 7.50-7.51(2H, m); 7.05 (1H, dd, J=4.
3 & 2.6 Hz); 6.93-6.82 (3H, m); 5.44 (2H, s); 3.90
(3H, s); 2.58 (2H, q, J=7.4 Hz); 2.19 (3H, s); 1.
22 (3H, t, J=7.6Hz).Working Example 183 N- [2-ethyl-4- (5-methoxybenzothiazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product number G5.17) Melting point: 169-172 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.74 (1H,
d, J = 8.6 Hz); 7.50-7.51 (2H, m); 7.05 (1H, dd, J = 4.
3 & 2.6 Hz); 6.93-6.82 (3H, m); 5.44 (2H, s); 3.90
(3H, s); 2.58 (2H, q, J = 7.4 Hz); 2.19 (3H, s); 1.
22 (3H, t, J = 7.6Hz).

【０４８７】[0487]

【実施例１８４】Ｎ−［２−エチル−４−（６−フルオロベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号G5.38 ）融点：198 −200 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.00-7.93
(1H, m); 7.60-7.51 (2H,m); 7.26-7.23 (1H, m); 6.93
-6.81 (3H, m); 5.44 (2H, s); 2.58 (2H, q, J=7.6 H
z); 2.19 (3H, s); 1.22 (3H, t, J=7.6 Hz).Working Example 184 N- [2-ethyl-4- (6-fluorobenzothiazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Article No. G5.38) Melting point: 198-200 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.00-7.93
(1H, m); 7.60-7.51 (2H, m); 7.26-7.23 (1H, m); 6.93
-6.81 (3H, m); 5.44 (2H, s); 2.58 (2H, q, J = 7.6 H
z); 2.19 (3H, s); 1.22 (3H, t, J = 7.6 Hz).

【０４８８】[0488]

【実施例１８５】Ｎ−［４−（５−クロロベンゾチアゾール−２−イルメ
トキシ）−２−エチルフェニル］アセトアミド（化合物
番号G5.45 ）融点：210 −213 ℃ ＮＭＲスペクトル(200MHz,CDCl₃+CD₃OD), δppm: 8.00
(1H, d, J=2.0 Hz); 7.85 (1H, d, J=8.6 Hz); 7.39 (1
H, dd, J=2.0 & 8.6 Hz); 7.30-6.60 (3H, m); 5.46 (2
H, s); 2.59 (2H, q, J=7.6 Hz); 2.16 (3H, s); 1.21
(3H, t, J=7.6 Hz). Working Example 185 N- [4- (5-chlorobenzothiazol-2-ylmethine)
Toxi) -2-ethylphenyl] acetamide (compound
No. G5.45) melting point: 210-213 ° C. NMR spectrum (200 MHz, CDCl ₃ + CD ₃ OD), δ ppm: 8.00
(1H, d, J = 2.0 Hz); 7.85 (1H, d, J = 8.6 Hz); 7.39 (1
H, dd, J = 2.0 & 8.6 Hz); 7.30-6.60 (3H, m); 5.46 (2
H, s); 2.59 (2H, q, J = 7.6 Hz); 2.16 (3H, s); 1.21
(3H, t, J = 7.6 Hz).

【０４８９】[0489]

【実施例１８６】Ｎ−［４−（５，６−ジフルオロベンゾチアゾール−２
−イルメトキシ）−２−エチルフェニル］アセトアミド
（化合物番号G6.31 ）融点：213 −214 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．２
４（１Ｈ，ｄ，Ｊ＝９．８Ｈｚ）；７．８６
−７．６３（２Ｈ，ｍ）；７．４５−７．３９
（１Ｈ，ｍ）；７．０（１Ｈ，ｄ，Ｊ＝２．
４Ｈｚ）；６．９８−６．９２（１Ｈ，ｍ）；
５．４２（２Ｈ，ｓ）；２．２２（３Ｈ，
ｓ）． Working Example 186 N- [4- (5,6-difluorobenzothiazole-2)
-Ylmethoxy) -2-ethylphenyl] acetamide
(Compound No. G6.31) Melting point: 213-214 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.2
4. (1H, d, J = 9.8 Hz); 7.86
-7.63 (2H, m); 7.45-7.39
(1H, m); 7.0 (1H, d, J = 2.
6.98-6.92 (1H, m);
5.42 (2H, s); 2.22 (3H, s)
s).

【０４９０】[0490]

【実施例１８７】Ｎ−［２−クロロ−４−（５−メチルベンゾチアゾール
−２−イルメトキシ）フェニル］アセトアミド（化合物
番号Ｈ４．３）融点：176 −179 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.22 (1H,
d, J=8.9 Hz); 7.83 (1H,s); 7.81 (1H, d, J=7.5 Hz);
7.35-7.26 (2H, m); 7.09 (1H, d, J=2.7 Hz);6.99-6.
95 (1H, m); 5.44 (2H, s); 2.52 (3H, s); 2.22 (3H,
s).Working Example 187 N- [2-chloro-4- (5-methylbenzothiazole)
-2-ylmethoxy) phenyl] acetamide (compound
No. H4.3) melting point: 176-179 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.22 (1H,
d, J = 8.9 Hz); 7.83 (1H, s); 7.81 (1H, d, J = 7.5 Hz);
7.35-7.26 (2H, m); 7.09 (1H, d, J = 2.7 Hz); 6.99-6.
95 (1H, m); 5.44 (2H, s); 2.52 (3H, s); 2.22 (3H,
s).

【０４９１】[0490]

【実施例１８８】Ｎ−［２−クロロ−４−（６−メチルベンゾチアゾール
−２−イルメトキシ）フェニル］アセトアミド（化合物
番号H4.8）融点：151 −153 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.22 (1H,
d, J=8.8 Hz); 7.91 (1H,d, J=8.4 Hz); 7.68 (1H, s);
7.41 (1H, s); 7.30 (1H, dd, J=8.2 & 3.0 Hz); 7.09
(1H, d, J=3.0 Hz); 6.96 (1H, dd, J=9.2 & 3.2 Hz);
5.43 (2H, s); 2.50 (3H, s); 2.22 (3H, s).Working Example 188 N- [2-Chloro-4- (6-methylbenzothiazole)
-2-ylmethoxy) phenyl] acetamide (compound
No. H4.8) Melting point: 151-153 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.22 (1H,
d, J = 8.8 Hz); 7.91 (1H, d, J = 8.4 Hz); 7.68 (1H, s);
7.41 (1H, s); 7.30 (1H, dd, J = 8.2 & 3.0 Hz); 7.09
(1H, d, J = 3.0 Hz); 6.96 (1H, dd, J = 9.2 & 3.2 Hz);
5.43 (2H, s); 2.50 (3H, s); 2.22 (3H, s).

【０４９２】[0492]

【実施例１８９】Ｎ−［２−クロロ−４−（５−メトキシベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号H4.19 ）融点：160 −163 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.23 (1H,
d, J=9.0 Hz); 7.74 (1H,d, J=8.8 Hz); 7.52 (1H, d,
J=2.4 Hz); 7.41 (1H, s); 7.10-6.94 (3H, m);5.43 (2
H, s); 3.90 (3H, s); 2.22 (3H, s).Working Example 189 N- [2-chloro-4- (5-methoxybenzothiazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product number H4.19) Melting point: 160-163 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.23 (1H,
d, J = 9.0 Hz); 7.74 (1H, d, J = 8.8 Hz); 7.52 (1H, d,
J = 2.4 Hz); 7.41 (1H, s); 7.10-6.94 (3H, m); 5.43 (2
H, s); 3.90 (3H, s); 2.22 (3H, s).

【０４９３】[0493]

【実施例１９０】Ｎ−［２−クロロ−４−（６−フルオロベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号H4.38 ）融点：174 −176 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.24 (1H,
d, J=9.2 Hz); 8.03-7.94(1H, m); 7.58 (1H, dd, J=8.
0 & 2.6 Hz); 7.41 (1H, s); 7.30-7.19 (1H, m); 7.09
(1H, d, J=2.8 Hz); 6.96 (1H, dd, J=9.2 & 2.6 Hz);
5.42 (2H, s); 2.22 (3H, s).Working Example 190 N- [2-Chloro-4- (6-fluorobenzothiazolate)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product number H4.38) Melting point: 174-176 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.24 (1H,
d, J = 9.2 Hz); 8.03-7.94 (1H, m); 7.58 (1H, dd, J = 8.
0 & 2.6 Hz); 7.41 (1H, s); 7.30-7.19 (1H, m); 7.09
(1H, d, J = 2.8 Hz); 6.96 (1H, dd, J = 9.2 & 2.6 Hz);
5.42 (2H, s); 2.22 (3H, s).

【０４９４】[0494]

【実施例１９１】Ｎ−［２−クロロ−４−（５−クロロベンゾチアゾール
−２−イルメトキシ）フェニル］アセトアミド（化合物
番号H4.43 ）融点：192 −193 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.24 (1H,
d, J=8.9 Hz); 8.20 (1H,d, J=2.0 Hz); 7.82 (1H, d,
J=8.6 Hz); 7.42-7.37 (2H, m); 7.09 (1H, d, J=2.9 H
z); 6.99-6.93 (1H, m); 5.44 (2H, s); 2.22 (3H, s).Working Example 191 N- [2-Chloro-4- (5-chlorobenzothiazole)
-2-ylmethoxy) phenyl] acetamide (compound
No. H4.43) melting point: 192-193 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.24 (1H,
d, J = 8.9 Hz); 8.20 (1H, d, J = 2.0 Hz); 7.82 (1H, d,
J = 8.6 Hz); 7.42-7.37 (2H, m); 7.09 (1H, d, J = 2.9 H
z); 6.99-6.93 (1H, m); 5.44 (2H, s); 2.22 (3H, s).

【０４９５】[0495]

【実施例１９２】Ｎ−［２−クロロ−４−（５，６−ジフルオロベンゾチ
アゾール−２−イルメトキシ）フェニル］アセトアミド
（化合物番号H4.91 ）融点：170 −172 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.24 (1H,
d, J=9.8 Hz); 7.86-7.63(2H, m); 7.45-7.39 (1H, m);
7.08 (1H, d, J=2.4 Hz); 6.98-6.92 (1H, m);5.42 (2
H, s); 2.22 (3H, s).Working Example 192 N- [2-Chloro-4- (5,6-difluorobenzothi)
Azol-2-ylmethoxy) phenyl] acetamide
(Compound No. H4.91) Melting point: 170-172 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.24 (1H,
d, J = 9.8 Hz); 7.86-7.63 (2H, m); 7.45-7.39 (1H, m);
7.08 (1H, d, J = 2.4 Hz); 6.98-6.92 (1H, m); 5.42 (2
H, s); 2.22 (3H, s).

【０４９６】[0496]

【実施例１９３】Ｎ−［２，３−ジメチル−４−（５−メチルベンゾチア
ゾール−２−イルメトキシ）フェニル］アセトアミド
（化合物番号H7.4）融点：260 −261 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．８
３−７．７５（３Ｈ，ｍ）；７．２９−７．２６
（２Ｈ，ｍ）；６．８３−６．７９（２Ｈ，
ｍ）；５．４４（２Ｈ，ｓ）；２．５２（３
Ｈ，ｓ）；２．３１（３Ｈ，ｓ）；２．１９
（３Ｈ，ｓ）．Working Example 193 N- [2,3-dimethyl-4- (5-methylbenzothia)
Zol-2-ylmethoxy) phenyl] acetamide
(Compound No. H7.4) Melting point: 260-261 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.8
3-7.75 (3H, m); 7.29-7.26
(2H, m); 6.83-6.79 (2H, m);
m); 5.44 (2H, s); 2.52 (3
H, s); 2.31 (3H, s); 2.19
(3H, s).

【０４９７】[0497]

【実施例１９４】Ｎ−［２，３−ジメチル−４−（６−メチルベンゾチア
ゾール−２−イルメトキシ）フェニル］アセトアミド
（化合物番号Ｈ７．９）融点：224 −226 ℃ ＮＭＲスペクトル(200MHz, DMSO-d₆）, δppm: 9.30 (1
H, s); 7.93 (1H, s); 7.91 (1H, d, J=8.4 Hz); 7.37
(1H, dd, J=7.8 & 1.4 Hz); 7.05 (1H, d, J=8.8Hz);
6.93 (1H, d, J=9.0 Hz); 5.54 (2H, s); 2.46 (3H,
s); 2.24 (3H, s);2.09 (3H, s); 2.02 (3H, s).Working Example 194 N- [2,3-dimethyl-4- (6-methylbenzothia)
Zol-2-ylmethoxy) phenyl] acetamide
(Compound No. H7.9) melting point: 224-226 ° C. NMR spectrum (200 MHz, DMSO-d ₆ ), δ ppm: 9.30 (1
H, s); 7.93 (1H, s); 7.91 (1H, d, J = 8.4 Hz); 7.37
(1H, dd, J = 7.8 & 1.4 Hz); 7.05 (1H, d, J = 8.8Hz);
6.93 (1H, d, J = 9.0 Hz); 5.54 (2H, s); 2.46 (3H,
s); 2.24 (3H, s); 2.09 (3H, s); 2.02 (3H, s).

【０４９８】[0498]

【実施例１９５】Ｎ−［４−（６−メトキシベンゾチアゾール−２−イル
メトキシ）−２，３−ジメチルフェニル］アセトアミド
（化合物番号H7.21 ）融点：229 −232 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.90 (1H,
d, J=8.9 Hz); 7.35 (1H,d, J=2.2 Hz); 7.23-7.08 (1
H, m); 6.84-6.79 (3H, m); 5.41 (2H, s); 3.88(3H,
s); 2.30 (3H, s); 2.19 (6H, s).Working Example 195 N- [4- (6-Methoxybenzothiazol-2-yl)
Methoxy) -2,3-dimethylphenyl] acetamide
(Compound No. H7.21) Melting point: 229-232 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.90 (1H,
d, J = 8.9 Hz); 7.35 (1H, d, J = 2.2 Hz); 7.23-7.08 (1
H, m); 6.84-6.79 (3H, m); 5.41 (2H, s); 3.88 (3H,
s); 2.30 (3H, s); 2.19 (6H, s).

【０４９９】[0499]

【実施例１９６】Ｎ−［４−（６−フルオロベンゾチアゾール−２−イル
メトキシ）−２，３−ジメチルフェニル］アセトアミド
（化合物番号H7.41 ）融点：245 −247 ℃ ＮＭＲスペクトル(200MHz, DMSO-d₆）, δppm: 9.30 (1
H, s); 8.09-8.02 (2H,m); 7.42 (1H, td, J=8.6 & 2.6
Hz); 7.05 (2H, q, J=9.0 Hz); 6.94 (2H, d,J=8.6 H
z); 5.56 (2H, s); 2.25 (3H, s); 2.09 (3H, s); 2.02
(3H, s).Working Example 196 N- [4- (6-Fluorobenzothiazol-2-yl)
Methoxy) -2,3-dimethylphenyl] acetamide
(Compound No. H7.41) Melting point: 245-247 ° C. NMR spectrum (200 MHz, DMSO-d ₆ ), δ ppm: 9.30 (1
H, s); 8.09-8.02 (2H, m); 7.42 (1H, td, J = 8.6 & 2.6
Hz); 7.05 (2H, q, J = 9.0 Hz); 6.94 (2H, d, J = 8.6 H
z); 5.56 (2H, s); 2.25 (3H, s); 2.09 (3H, s); 2.02
(3H, s).

【０５００】[0500]

【実施例１９７】Ｎ−［４−（５−クロロベンゾチアゾール−２−イルメ
トキシ）−２，３−ジメチルフェニル］アセトアミド
（化合物番号H7.49 ）融点：246 −250 ℃ ＮＭＲスペクトル(200MHz, DMSO-d₆）, δppm: 9.29-9.
27 (1H, br.s); 8.27-8.06 (2H, m); 7.49 (1H, dd, J=
2.2 & 8.5 Hz); 7.04 (1H, d, J=8.4 Hz); 6.91(1H, d,
J=8.4 Hz); 5.55 (2H, s); 2.25 (3H, s); 2.10 (3H,
s); 2.02 (3H, s). Working Example 197 N- [4- (5-chlorobenzothiazol-2-ylmethine)
Toxi) -2,3-dimethylphenyl] acetamide
(Compound No. H7.49) Melting point: 246-250 ° C. NMR spectrum (200 MHz, DMSO-d ₆ ), δ ppm: 9.29-9.
27 (1H, br.s); 8.27-8.06 (2H, m); 7.49 (1H, dd, J =
2.2 & 8.5 Hz); 7.04 (1H, d, J = 8.4 Hz); 6.91 (1H, d,
J = 8.4 Hz); 5.55 (2H, s); 2.25 (3H, s); 2.10 (3H, s)
s); 2.02 (3H, s).

【０５０１】[0501]

【実施例１９８】Ｎ−［４−（５，６−ジフルオロベンゾチアゾール−２
−イルメトキシ）−２，３−ジメチルフェニル］アセト
アミド（化合物番号H7.106）融点：248 −249 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.80 (1H, d
d, J=10.5 & 7.3 Hz); 7.67 (1H, dd, J=9.5 & 7.7 H
z); 7.29-7.25 (1H, m); 6.87 (1H, br.s); 6.80 (1H,
d, J=8.8 Hz); 5.42 (2H, s); 2.30 (3H, s); 2.20 (6
H, s). Working Example 198 N- [4- (5,6-difluorobenzothiazole-2)
-Ylmethoxy) -2,3-dimethylphenyl] aceto
Amide (Compound No. H7.106) Melting point: 248-249 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.80 (1H, d
d, J = 10.5 & 7.3 Hz); 7.67 (1H, dd, J = 9.5 & 7.7 H
z); 7.29-7.25 (1H, m); 6.87 (1H, br.s); 6.80 (1H,
d, J = 8.8 Hz); 5.42 (2H, s); 2.30 (3H, s); 2.20 (6
H, s).

【０５０２】[0502]

【実施例１９９】Ｎ−［４−（６−メトキシベンゾチアゾール−２−イル
メチルチオ) フェニル］アセトアミド（化合物番号F3.2
1 ）融点：124 −125 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.80 (1H,
d, J=8.8 Hz); 7.45-7.10(6H, m); 7.04 (1H, dd, J=8.
9 & 2.7 Hz); 4.42 (2H, s); 3.86 (3H, s); 2.15 (3H,
s).Working Example 199 N- [4- (6-Methoxybenzothiazol-2-yl)
Methylthio) phenyl] acetamide (Compound No. F3.2
1) Melting point: 124-125 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 7.80 (1H,
d, J = 8.8 Hz); 7.45-7.10 (6H, m); 7.04 (1H, dd, J = 8.
9 & 2.7 Hz); 4.42 (2H, s); 3.86 (3H, s); 2.15 (3H,
s).

【０５０３】[0503]

【実施例２００】Ｎ−［４−（６−エトキシベンゾチアゾール−２−イル
メトキシ）フェニル］アセトアミド（化合物番号F3.56
）融点：139 −141 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．８
９（１Ｈ，ｄ，Ｊ＝９．１Ｈｚ）；７．４３
−７．３１（３Ｈ，ｍ）；７．１１−６．９７
（４Ｈ，ｍ）；５．４１（２Ｈ，ｓ）；４．
０９（２Ｈ，ｑ，Ｊ＝７．１Ｈｚ）；２．１
３（３Ｈ，ｓ）；１．４５（３Ｈ，ｔ，Ｊ＝
７．０Ｈｚ）．Working Example 200 N- [4- (6-ethoxybenzothiazol-2-yl)
Methoxy) phenyl] acetamide (Compound No.F3.56
) Melting point: 139-141 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.8
9 (1H, d, J = 9.1 Hz); 7.43
-7.31 (3H, m); 7.11-6.97.
(4H, m); 5.41 (2H, s);
09 (2H, q, J = 7.1 Hz); 2.1
3 (3H, s); 1.45 (3H, t, J =
7.0 Hz).

【０５０４】[0504]

【実施例２０１】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）フェニル］アセトアミド（化合物番号Ｆ４．
１１）融点：201 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.86-7.79
(1H, m); 7.70 (1H, dd,J=9.3 & 2.5 Hz); 7.43 (2H,
d, J=9.0 Hz); 7.30-7.10 (2H, m); 7.05 (1H, br.s);
7.00 (2H, d, J=8.9 Hz); 5.45 (2H, s); 2.16 (3H,
s).Working Example 201 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) phenyl] acetamide (Compound No. F4.
11) Melting point: 201 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.86-7.79
(1H, m); 7.70 (1H, dd, J = 9.3 & 2.5 Hz); 7.43 (2H,
d, J = 9.0 Hz); 7.30-7.10 (2H, m); 7.05 (1H, br.s);
7.00 (2H, d, J = 8.9 Hz); 5.45 (2H, s); 2.16 (3H,
s).

【０５０５】[0505]

【実施例２０２】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メチルチオ) フェニル］アセトアミド（化合物番号F4.1
6 ）融点：108 −109 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.74 (1H, d
d, J=8.8 & 5.1 Hz); 7.61 (1H, dd, J=9.5 & 2.5 Hz);
7.45-7.33 (4H, m); 7.13 (1H, td, J=8.8 & 2.5 Hz);
4.44 (2H, s); 2.14 (3H, s).Working Example 202 N- [4- (5-Fluorobenzothiazol-2-yl)
Methylthio) phenyl] acetamide (Compound No.F4.1
6) Melting point: 108-109 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 7.74 (1H, d
d, J = 8.8 & 5.1 Hz); 7.61 (1H, dd, J = 9.5 & 2.5 Hz);
7.45-7.33 (4H, m); 7.13 (1H, td, J = 8.8 & 2.5 Hz);
4.44 (2H, s); 2.14 (3H, s).

【０５０６】[0506]

【実施例２０３】Ｎ−［４−（５−トリフルオロメチルベンゾチアゾール
−２−イルメトキシ）フェニル］アセトアミド（化合物
番号F5.9）融点：208 −210 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.29 (1H,
s); 8.02 (1H, d, J=8.4Hz); 7.67-7.66 (1H, m); 7.46
-7.41 (2H, m); 7.09-7.02 (1H, br.m); 7.01-6.97 (2
H, m); 5.48 (2H, s); 2.16 (3H, s).Working Example 203 N- [4- (5-trifluoromethylbenzothiazole)
-2-ylmethoxy) phenyl] acetamide (compound
No. F5.9) melting point: 208-210 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.29 (1H,
s); 8.02 (1H, d, J = 8.4Hz); 7.67-7.66 (1H, m); 7.46
-7.41 (2H, m); 7.09-7.02 (1H, br.m); 7.01-6.97 (2
H, m); 5.48 (2H, s); 2.16 (3H, s).

【０５０７】[0507]

【実施例２０４】Ｎ−［４−（４−クロロ−５−メトキシベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号F7.136）融点：193 −195 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.73 (1H,
d, J=8.7 Hz); 7.43 (2H,d, J=9.2 Hz); 7.15-6.97 (4
H, m); 5.50 (2H, s); 4.01 (3H, s); 2.16 (3H,s).Working Example 204 N- [4- (4-Chloro-5-methoxybenzothiazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Article No. F7.136) Melting point: 193-195 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.73 (1H,
d, J = 8.7 Hz); 7.43 (2H, d, J = 9.2 Hz); 7.15-6.97 (4
H, m); 5.50 (2H, s); 4.01 (3H, s); 2.16 (3H, s).

【０５０８】[0508]

【実施例２０５】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）−２−メチルフェニル］アセトアミド（化合
物番号G1.55 ）融点：205 −207 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.86-7.79
(1H, m); 7.74-7.68 (1H,m); 7.69-7.53 (1H, m); 7.19
-7.18 (1H, m); 6.89-6.85 (3H, m); 5.44 (2H,s); 2.2
5 (3H, s); 2.19 (3H, s).Working Example 205 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) -2-methylphenyl] acetamide (compound
Product No. G1.55) Melting point: 205-207 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 7.86-7.79
(1H, m); 7.74-7.68 (1H, m); 7.69-7.53 (1H, m); 7.19
-7.18 (1H, m); 6.89-6.85 (3H, m); 5.44 (2H, s); 2.2
5 (3H, s); 2.19 (3H, s).

【０５０９】[0509]

【実施例２０６】Ｎ−［２−メチル−４−（５−トリフルオロメチルベン
ゾチアゾール−２−イルメトキシ）フェニル］アセトア
ミド（化合物番号G1.92 ）融点：209 −210 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.29 (1H,
s); 8.02 (1H, d, J=8.7Hz); 7.67-7.53 (2H, m); 6.89
(1H, s); 6.85-6.82 (2H, m); 5.48 (2H, s); 2.25 (3
H, s); 2.19 (3H, s).Working Example 206 N- [2-methyl-4- (5-trifluoromethylbenz)
Zothiazol-2-ylmethoxy) phenyl] acetoa
Mide (Compound No. G1.92) Melting point: 209-210 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.29 (1H,
s); 8.02 (1H, d, J = 8.7Hz); 7.67-7.53 (2H, m); 6.89
(1H, s); 6.85-6.82 (2H, m); 5.48 (2H, s); 2.25 (3
H, s); 2.19 (3H, s).

【０５１０】[0510]

【実施例２０７】Ｎ−［２−エチル−４−（６−メトキシベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号G5.20 ）融点：157 −160 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．９
０（１Ｈ，ｄ，Ｊ＝８．９Ｈｚ）；７．５１
（１Ｈ，ｄ，Ｊ＝８．６Ｈｚ）；７．３４
（１Ｈ，ｄ，Ｊ＝２．３Ｈｚ）；７．０９
（１Ｈ，ｄｄ，Ｊ＝９．０＆２．６Ｈｚ）；
６．９１−５．８２（３Ｈ，ｍ）；５．４１
（２Ｈ，ｓ）；３．８８（３Ｈ，ｓ）；２．
５７（２Ｈ，ｑ，Ｊ＝７．４Ｈｚ）；２．１
８（３Ｈ，ｓ）；１．２１（３Ｈ，ｔ，Ｊ
＝７．４Ｈｚ）．Working Example 207 N- [2-ethyl-4- (6-methoxybenzothiazolate)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Compound No. G5.20) Melting point: 157-160 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.9
0 (1H, d, J = 8.9 Hz); 7.51
(1H, d, J = 8.6 Hz); 7.34
(1H, d, J = 2.3 Hz); 7.09
(1H, dd, J = 9.0 & 2.6 Hz);
6.91-5.82 (3H, m); 5.41
(2H, s); 3.88 (3H, s);
57 (2H, q, J = 7.4 Hz); 2.1
8 (3H, s); 1.21 (3H, t, J
= 7.4 Hz).

【０５１１】[0511]

【実施例２０８】Ｎ−［２−エチル−４−（５−フルオロベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号Ｇ５．３３）融点：197 −198 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.86-7.79
(1H, m); 7.74-7.68 (1H,m); 7.53 (1H, d, J=8.4 Hz);
7.26-7.18 (1H, m); 6.92-6.84 (3H, m); 5.45(2H,
s); 2.58 (2H, q, J=7.2 Hz); 2.19 (3H, s); 1.23 (3
H, t, J=7.5 Hz).Working Example 208 N- [2-ethyl-4- (5-fluorobenzothiazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Article No. G5.33) Melting point: 197-198 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.86-7.79
(1H, m); 7.74-7.68 (1H, m); 7.53 (1H, d, J = 8.4 Hz);
7.26-7.18 (1H, m); 6.92-6.84 (3H, m); 5.45 (2H,
s); 2.58 (2H, q, J = 7.2 Hz); 2.19 (3H, s); 1.23 (3
(H, t, J = 7.5 Hz).

【０５１２】[0512]

【実施例２０９】Ｎ−［２−エチル−４−（５−トリフルオロメチルベン
ゾチアゾール−２−イルメトキシ）フェニル］アセトア
ミド（化合物番号G5.52 ）融点：210 −212 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.29 (1H,
s); 8.02 (1H, d, J=8.4Hz); 7.64 (1H, dd, J=9.0 &
1.8 Hz); 7.54 (1H, d, J=8.8 Hz); 6.93 (1H, s); 6.8
8 (4H, dd, J=11.8 & 3.1 Hz); 5.49 (2H, s); 2.59 (2
H, q, J=7.6 Hz);2.19 (3H, s); 1.23 (3H, t, J=7.5 H
z).Working Example 209 N- [2-ethyl-4- (5-trifluoromethylbenz)
Zothiazol-2-ylmethoxy) phenyl] acetoa
Mide (Compound No. G5.52) Melting point: 210-212 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.29 (1H,
s); 8.02 (1H, d, J = 8.4Hz); 7.64 (1H, dd, J = 9.0 &
(1.8 Hz); 7.54 (1H, d, J = 8.8 Hz); 6.93 (1H, s); 6.8
8 (4H, dd, J = 11.8 & 3.1 Hz); 5.49 (2H, s); 2.59 (2
H, q, J = 7.6 Hz); 2.19 (3H, s); 1.23 (3H, t, J = 7.5 H
z).

【０５１３】[0513]

【実施例２１０】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）−２−メトキシフェニル］アセトアミド（化
合物番号G8.31 ）融点：170 −172 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.24 (1H,
d, J=8.8 Hz); 7.82 (1H,dd, J=8.8 & 5.1 Hz); 7.71
(1H, dd, J=9.3 & 2.4 Hz); 7.55 (1H, br.s); 7.19 (1
H, td, J=8.8 & 2.4 Hz); 6.63-6.55 (2H, m); 5.45 (2
H, s); 3.87 (3H,s); 2.18 (3H, s).Working Example 210 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) -2-methoxyphenyl] acetamide
Compound No. G8.31) Melting point: 170-172 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.24 (1H,
d, J = 8.8 Hz); 7.82 (1H, dd, J = 8.8 & 5.1 Hz); 7.71
(1H, dd, J = 9.3 & 2.4 Hz); 7.55 (1H, br.s); 7.19 (1
H, td, J = 8.8 & 2.4 Hz); 6.63-6.55 (2H, m); 5.45 (2
H, s); 3.87 (3H, s); 2.18 (3H, s).

【０５１４】[0514]

【実施例２１１】Ｎ−［４−（６−フルオロベンゾチアゾール−２−イル
メトキシ）−２−メトキシフェニル］アセトアミド（化
合物番号G8.38 ）融点：155 −159 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.24 (1H,
d, J=8.8 Hz); 7.97 (1H,dd, J=8.8 & 4.8 Hz); 7.57
(1H, dd, J=8.1 & 2.5 Hz); 7.24 (1H, td, J=8.8& 2.5
Hz); 6.63-6.55 (2H, m); 5.54 (2H, s); 3.87 (3H,
s); 2.17 (3H, s).Working Example 211 N- [4- (6-Fluorobenzothiazol-2-yl)
Methoxy) -2-methoxyphenyl] acetamide
Compound No. G8.38) Melting point: 155-159 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.24 (1H,
d, J = 8.8 Hz); 7.97 (1H, dd, J = 8.8 & 4.8 Hz); 7.57
(1H, dd, J = 8.1 & 2.5 Hz); 7.24 (1H, td, J = 8.8 & 2.5
Hz); 6.63-6.55 (2H, m); 5.54 (2H, s); 3.87 (3H,
s); 2.17 (3H, s).

【０５１５】[0515]

【実施例２１２】Ｎ−［２−エトキシ−４−（５−フルオロベンゾチアゾ
ール−２−イルメトキシ）フェニル］アセトアミド（化
合物番号G10.51）融点：177.5 −179 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.25 (1H,
d, J=8.7 Hz); 7.82 (1H,dd, J=8.8 & 5.0 Hz); 7.71
(1H, dd, J=9.4 & 2.5 Hz); 7.57 (1H, br.s); 7.18 (1
H, td, J=8.8 & 2.5 Hz); 6.62-6.54 (2H, m); 5.44 (2
H, s); 4.10 (2H,q, J=7.0 Hz); 2.18 (3H, s); 1.46
(3H, t, J=7.0 Hz).Working Example 212 N- [2-ethoxy-4- (5-fluorobenzothiazo)
2-ylmethoxy) phenyl] acetamide
Compound No. G10.51) Melting point: 177.5-179 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.25 (1H,
d, J = 8.7 Hz); 7.82 (1H, dd, J = 8.8 & 5.0 Hz); 7.71
(1H, dd, J = 9.4 & 2.5 Hz); 7.57 (1H, br.s); 7.18 (1
H, td, J = 8.8 & 2.5 Hz); 6.62-6.54 (2H, m); 5.44 (2
H, s); 4.10 (2H, q, J = 7.0 Hz); 2.18 (3H, s); 1.46
(3H, t, J = 7.0 Hz).

【０５１６】[0516]

【実施例２１３】Ｎ−［２−ジフルオロメチル−４−（５−フルオロベン
ゾチアゾール−２−イルメトキシ）フェニル］アセトア
ミド（化合物番号G10.57）融点：180 −185 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.87-7.69
(3H, m); 7.31-7.12 (4H,m); 6.66 (1H, t, J=54.7 H
z); 5.48 (2H, s); 2.20 (3H, s).Working Example 213 N- [2-Difluoromethyl-4- (5-fluorobenzene)
Zothiazol-2-ylmethoxy) phenyl] acetoa
Mide (Compound No. G10.57) Melting point: 180-185 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.87-7.69
(3H, m); 7.31-7.12 (4H, m); 6.66 (1H, t, J = 54.7 H
z); 5.48 (2H, s); 2.20 (3H, s).

【０５１７】[0517]

【実施例２１４】Ｎ−［２−ジフルオロメトキシ−４−（５−フルオロベ
ンゾチアゾール−２−イルメトキシ）フェニル］アセト
アミド（化合物番号G10.61）融点：137 −138 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.24 (1H,
d, J=9.8 Hz); 7.83 (1H,dd, J=8.8 & 4.8 Hz); 7.71
(1H, dd, J=9.3 & 2.4 Hz); 7.34-7.30 (1H, m);7.20
(1H, td, J=8.8 & 2.5 Hz); 6.91-6.86 (2H, m); 6.52
(1H, t, J=73.1 Hz); 5.45 (2H, s); 2.20 (3H, s). Working Example 214 N- [2-difluoromethoxy-4- (5-fluorobe)
Nzothiazol-2-ylmethoxy) phenyl] aceto
Amide (Compound No. G10.61) Melting point: 137-138 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.24 (1H,
d, J = 9.8 Hz); 7.83 (1H, dd, J = 8.8 & 4.8 Hz); 7.71
(1H, dd, J = 9.3 & 2.4 Hz); 7.34-7.30 (1H, m); 7.20
(1H, td, J = 8.8 & 2.5 Hz); 6.91-6.86 (2H, m); 6.52
(1H, t, J = 73.1 Hz); 5.45 (2H, s); 2.20 (3H, s).

【０５１８】[0518]

【実施例２１５】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）−２−（２，２，２−トリフルオロエトキ
シ) フェニル］アセトアミド（化合物番号G10.63）融点：167 −168 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.25 (1H,
d, J=9.0 Hz); 7.83 (1H,dd, J=8.8 & 5.1 Hz); 7.71
(1H, dd, J=9.3 & 2.4 Hz); 7.42 (1H, br.s); 7.20 (1
H, td, J=8.8 & 2.5 Hz); 6.70 (1H, dd, J=8.9 & 2.7
Hz); 6.63 (1H, d,J=2.6 Hz); 5.45 (2H, s); 4.39 (2
H, q, J=8.0 Hz); 2.19 (3H, s).Working Example 215 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) -2- (2,2,2-trifluoroethoxy)
B) Phenyl] acetamide (Compound No. G10.63) Melting point: 167-168 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.25 (1H,
d, J = 9.0 Hz); 7.83 (1H, dd, J = 8.8 & 5.1 Hz); 7.71
(1H, dd, J = 9.3 & 2.4 Hz); 7.42 (1H, br.s); 7.20 (1
H, td, J = 8.8 & 2.5 Hz); 6.70 (1H, dd, J = 8.9 & 2.7
Hz); 6.63 (1H, d, J = 2.6 Hz); 5.45 (2H, s); 4.39 (2
(H, q, J = 8.0 Hz); 2.19 (3H, s).

【０５１９】[0519]

【実施例２１６】Ｎ−［２−クロロ−４−（６−メトキシベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号H4.22 ）融点：148 −150 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.21 (1H,
d, J=9.0 Hz); 7.91 (1H,d, J=8.8 Hz); 7.42 (1H, s);
7.34 (1H, d, J=2.5 Hz); 7.13-7.07 (2H, m);6.96 (1
H, dd, J=9.0 & 2.9 Hz); 5.40 (2H, s); 3.88 (3H,
s); 2.22 (3H, s).Working Example 216 N- [2-Chloro-4- (6-methoxybenzothiazolate)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product number H4.22) Melting point: 148-150 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.21 (1H,
d, J = 9.0 Hz); 7.91 (1H, d, J = 8.8 Hz); 7.42 (1H, s);
7.34 (1H, d, J = 2.5 Hz); 7.13-7.07 (2H, m); 6.96 (1
H, dd, J = 9.0 & 2.9 Hz); 5.40 (2H, s); 3.88 (3H,
s); 2.22 (3H, s).

【０５２０】[0520]

【実施例２１７】Ｎ−［２−クロロ−４−（５−フルオロベンゾチアゾー
ル−２−イルメトキシ）フェニル］アセトアミド（化合
物番号H4.35 ）融点：160 −167 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．２
３（１Ｈ，ｄ，Ｊ＝８．９Ｈｚ）；７．８３
（１Ｈ，ｄｄ，Ｊ＝８．８＆５．１Ｈｚ）；
７．７１（１Ｈ，ｄｄ，Ｊ＝９．４＆２．
５Ｈｚ）；７．４２（１Ｈ，ｂｒ．ｓ）；
７．１９（１Ｈ，ｔｄ，Ｊ＝８．８＆２．５
Ｈｚ）；７．０９（１Ｈ，ｄ，Ｊ＝２．９
Ｈｚ）；６．９６（１Ｈ，ｄｄ，Ｊ＝９．１＆
２．９Ｈｚ）；５．４４（２Ｈ，ｓ）；
２．２２（３Ｈ，ｓ）．Working Example 217 N- [2-chloro-4- (5-fluorobenzothiazole)
Ru-2-ylmethoxy) phenyl] acetamide (compound
Product number H4.35) Melting point: 160-167 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.2
3. (1H, d, J = 8.9 Hz); 7.83
(1H, dd, J = 8.8 & 5.1 Hz);
7.71 (1H, dd, J = 9.4 & 2.
7.42 (1H, br.s);
7.19 (1H, td, J = 8.8 & 2.5
Hz); 7.09 (1H, d, J = 2.9)
Hz); 6.96 (1H, dd, J = 9.1 &
2.9 Hz); 5.44 (2H, s);
2.22 (3H, s).

【０５２１】[0521]

【実施例２１８】Ｎ−［２−クロロ−４−（５−トリフルオロメチルベン
ゾチアゾール−２−イルメトキシ）フェニル］アセトア
ミド（化合物番号Ｈ４．５０）融点：183 −184 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.29 (1H,
s); 8.25 (1H, d, J=9.0Hz); 8.03 (1H, d, J=8.4 Hz);
7.66 (1H, dd, J=8.4 & 1.6 Hz); 7.42 (1H, s); 7.10
(1H, d, J=2.9 Hz); 6.97 (1H, dd, J=9.0 & 2.9 Hz);
5.48 (2H, s); 2.22 (3H, s).Working Example 218 N- [2-chloro-4- (5-trifluoromethylbenz)
Zothiazol-2-ylmethoxy) phenyl] acetoa
Mide (Compound No. H4.50) Melting point: 183-184 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.29 (1H,
s); 8.25 (1H, d, J = 9.0Hz); 8.03 (1H, d, J = 8.4 Hz);
7.66 (1H, dd, J = 8.4 & 1.6 Hz); 7.42 (1H, s); 7.10
(1H, d, J = 2.9 Hz); 6.97 (1H, dd, J = 9.0 & 2.9 Hz);
5.48 (2H, s); 2.22 (3H, s).

【０５２２】[0522]

【実施例２１９】Ｎ−［４−（５−メトキシベンゾチアゾール−２−イル
メトキシ）−２，３−ジメチルフェニル］アセトアミド
（化合物番号H7.18 ）融点：224 −225 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 9.30 (1H,
s); 8.01 (1H, d, J=8.9Hz); 7.57 (1H, d, J=2.4 Hz);
7.15-6.92 (3H, m); 5.55 (2H, s); 3.87 (3H,s); 2.2
5 (3H, s); 2.10 (3H, s); 2.03 (3H, s).Working Example 219 N- [4- (5-Methoxybenzothiazol-2-yl)
Methoxy) -2,3-dimethylphenyl] acetamide
(Compound No. H7.18) Melting point: 224-225 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 9.30 (1H,
s); 8.01 (1H, d, J = 8.9Hz); 7.57 (1H, d, J = 2.4 Hz);
7.15-6.92 (3H, m); 5.55 (2H, s); 3.87 (3H, s); 2.2
5 (3H, s); 2.10 (3H, s); 2.03 (3H, s).

【０５２３】[0523]

【実施例２２０】Ｎ−［４−（５−フルオロベンゾチアゾール−２−イル
メトキシ）−２，３−ジメチルフェニル］アセトアミド
（化合物番号H7.36 ）融点：245 −246 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.84-7.79
(1H, m); 7.73-7.69 (1H,m); 7.28-7.18 (2H, m); 6.83
-6.78 (2H, m); 5.44 (2H, s); 2.32 (3H, s); 2.20 (6
H, s).Working Example 220 N- [4- (5-Fluorobenzothiazol-2-yl)
Methoxy) -2,3-dimethylphenyl] acetamide
(Compound No. H7.36) Melting point: 245-246 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.84-7.79
(1H, m); 7.73-7.69 (1H, m); 7.28-7.18 (2H, m); 6.83
-6.78 (2H, m); 5.44 (2H, s); 2.32 (3H, s); 2.20 (6
H, s).

【０５２４】[0524]

【実施例２２１】Ｎ−［２，３−ジメチル−４−（５−トリフルオロメチ
ルベンゾチアゾール−２−イルメトキシ）フェニル］ア
セトアミド（化合物番号H7.63 ）融点：262 −263 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.29 (1H,
s); 8.03 (1H, d, J=8.7Hz); 7.65 (1H, d, J=8.3 Hz);
6.90 (1H, s); 6.81 (2H, d, J=8.5 Hz); 5.47(2H,
s); 2.32 (3H, s); 2.20 (6H, s).Working Example 221 N- [2,3-dimethyl-4- (5-trifluoromethyl)
Rubenzothiazol-2-ylmethoxy) phenyl] a
Cetamide (Compound No. H7.63) Melting point: 262-263 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.29 (1H,
s); 8.03 (1H, d, J = 8.7Hz); 7.65 (1H, d, J = 8.3 Hz);
6.90 (1H, s); 6.81 (2H, d, J = 8.5 Hz); 5.47 (2H,
s); 2.32 (3H, s); 2.20 (6H, s).

【０５２５】[0525]

【実施例２２２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メチルアセトアミド（化合
物番号D1.1）融点：108 −109 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H, d
d, J=7.2 & 1.3 Hz); 7.92 (1H, dd, J=7.2 & 1.3 Hz);
7.52 (1H, td, J=7.2 & 1.3 Hz); 7.42 (1H, td, J=7.
2 & 1.3 Hz); 7.06 (1H, d, J=8.4 Hz); 6.96 (1H, d,
J=2.5 Hz); 6.89(1H, dd, J=8.4 & 2.5 Hz); 5.49 (2H,
s); 3.15 (3H, s); 2.21 (3H, s); 1.76(3H, s). Working Example 222 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methylacetamide (compound
Compound No. D1.1) Melting point: 108-109 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.05 (1H, d
d, J = 7.2 & 1.3 Hz); 7.92 (1H, dd, J = 7.2 & 1.3 Hz);
7.52 (1H, td, J = 7.2 & 1.3 Hz); 7.42 (1H, td, J = 7.
2 & 1.3 Hz); 7.06 (1H, d, J = 8.4 Hz); 6.96 (1H, d,
J = 2.5 Hz); 6.89 (1H, dd, J = 8.4 & 2.5 Hz); 5.49 (2H,
s); 3.15 (3H, s); 2.21 (3H, s); 1.76 (3H, s).

【０５２６】[0526]

【実施例２２３】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−エチルアセトアミド（化合
物番号D1.5）アモルファスＮＭＲスペクトル(200Mz,CDCl₃),δppm: 8.04 (1H, dd,
J=7.3 & 1.3 Hz); 7.92(1H, dd, J=7.3 & 1.3 Hz); 7.
52 (1H, td, J=7.3 & 1.3 Hz); 7.42 (1H, td,J=7.3 &
1.3 Hz); 7.02 (1H, d, J=8.6 Hz); 6.98 (1H, d, J=2.
4 Hz); 6.89 (1H, dd, J=8.6 & 2.4 Hz); 5.49 (2H,
s); 4.04 (1H, sextet, J=7.3 Hz); 3.22(1H, sextet,
J=7.3 Hz); 2.21 (3H, s); 1.74 (3H, s); 1.10 (3H,
t, J=7.0 Hz). Working Example 223 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-ethylacetamide (compound
Product number D1.5 ) Amorphous NMR spectrum (200Mz, CDCl ₃ ), δppm: 8.04 (1H, dd,
J = 7.3 & 1.3 Hz); 7.92 (1H, dd, J = 7.3 & 1.3 Hz); 7.92
52 (1H, td, J = 7.3 & 1.3 Hz); 7.42 (1H, td, J = 7.3 &
1.3 Hz); 7.02 (1H, d, J = 8.6 Hz); 6.98 (1H, d, J = 2.
4 Hz); 6.89 (1H, dd, J = 8.6 & 2.4 Hz); 5.49 (2H,
s); 4.04 (1H, sextet, J = 7.3 Hz); 3.22 (1H, sextet,
J = 7.3 Hz); 2.21 (3H, s); 1.74 (3H, s); 1.10 (3H, s)
t, J = 7.0 Hz).

【０５２７】[0527]

【実施例２２４】Ｎ−アリル−Ｎ−［４−（ベンゾチアゾール−２−イル
メトキシ）−２−メチルフェニル］アセトアミド（化合
物番号D1.13 ）油状物ＮＭＲスペクトル(200Mz,CDCl₃),δppm: 8.05 (1H, dd,
J=7.5 & 1.3 Hz); 7.92(1H, dd, J=7.5 & 1.3 Hz); 7.
52 (1H, td, J=7.5 & 1.3 Hz); 7.42 (1H, td,J=7.5 &
1.3 Hz); 7.00 (1H, d, J=8.6 Hz); 6.96 (1H, d, J=3.
1 Hz); 6.86 (1H, dd, J=8.6 & 3.1 Hz); 5.97-5.77 (1
H, m); 5.48 (2H, s); 5.11-4.99 (2H,m); 4.68-4.57
(1H, m); 3.73 (1H, dd, J=14.4 & 7.2 Hz); 2.21 (3H,
s); 1.76 (3H, s).Working Example 224 N-allyl-N- [4- (benzothiazol-2-yl)
Methoxy) -2-methylphenyl] acetamide (compound
Product number D1.13) Oil NMR spectrum (200 Mz, CDCl ₃ ), δ ppm: 8.05 (1H, dd,
J = 7.5 & 1.3 Hz); 7.92 (1H, dd, J = 7.5 & 1.3 Hz); 7.
52 (1H, td, J = 7.5 & 1.3 Hz); 7.42 (1H, td, J = 7.5 &
1.30); 7.00 (1H, d, J = 8.6 Hz); 6.96 (1H, d, J = 3.
1 Hz); 6.86 (1H, dd, J = 8.6 & 3.1 Hz); 5.97-5.77 (1
H, m); 5.48 (2H, s); 5.11-4.99 (2H, m); 4.68-4.57
(1H, m); 3.73 (1H, dd, J = 14.4 & 7.2 Hz); 2.21 (3H,
s); 1.76 (3H, s).

【０５２８】[0528]

【実施例２２５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシメチルアセトアミ
ド（化合物番号D1.50 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-8.03
(1H, m); 7.94-7.90 (1H,m); 7.56-7.42 (2H, m); 7.08
(1H, d, J=8.4 Hz); 6.97 (1H, d, J=3.0Hz); 6.90 (1
H, dd, J=8.4 & 3.0 Hz); 5.49 (2H, s); 4.94 (2H, AB
q, J=9.8Hz, Dn=158.1 ）; 3.43 (3H, s); 2.22 (3H,
s); 1.80 (3H, s). Working Example 225 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxymethylacetamide
(Compound No. D1.50) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-8.03
(1H, m); 7.94-7.90 (1H, m); 7.56-7.42 (2H, m); 7.08
(1H, d, J = 8.4 Hz); 6.97 (1H, d, J = 3.0 Hz); 6.90 (1
H, dd, J = 8.4 & 3.0 Hz); 5.49 (2H, s); 4.94 (2H, AB
q, J = 9.8Hz, Dn = 158.1); 3.43 (3H, s); 2.22 (3H,
s); 1.80 (3H, s).

【０５２９】[0529]

【実施例２２６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−（２−エトキシエチル）ア
セトアミド（化合物番号D1.109）油状物ＮＭＲスペクトル(200Mz,CDCl₃),δppm: 8.05 (1H, dd,
J=7.2 & 1.3 Hz); 7.92(1H, dd, J=7.2 & 1.3 Hz); 7.
52 (1H, td, J=7.2 & 1.3 Hz); 7.42 (1H, td,J=7.2 &
1.3 Hz); 7.11 (1H, d, J=8.4 Hz); 6.95 (1H, d, J=2.
9 Hz); 6.88 (1H, dd, J=8.4 & 2.9 Hz); 5.48 (2H,
s); 4.26-4.07 (1H, m); 3.61-3.26 (5H,m); 2.21 (3H,
s); 1.75 (3H, s); 1.13 (3H, t, J=7.0 Hz). Working Example 226 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- (2-ethoxyethyl) a
Cetamide (Compound No.D1.109) oil NMR spectrum (200 Mz, CDCl ₃ ), δ ppm: 8.05 (1H, dd,
J = 7.2 & 1.3 Hz); 7.92 (1H, dd, J = 7.2 & 1.3 Hz); 7.92
52 (1H, td, J = 7.2 & 1.3 Hz); 7.42 (1H, td, J = 7.2 &
1.3 Hz); 7.11 (1H, d, J = 8.4 Hz); 6.95 (1H, d, J = 2.
9 Hz); 6.88 (1H, dd, J = 8.4 & 2.9 Hz); 5.48 (2H,
s); 4.26-4.07 (1H, m); 3.61-3.26 (5H, m); 2.21 (3H,
s); 1.75 (3H, s); 1.13 (3H, t, J = 7.0 Hz).

【０５３０】[0530]

【実施例２２７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−［２−（テトラヒドロピラ
ン−２−イルオキシ）エチル］アセトアミド（化合物番
号D1.118）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=7.2 Hz); 7.92 (1H,d, J=5.9 Hz); 7.56-7.37 (2
H, m); 7.12 (1H, dd, J=8.5 & 5.4 Hz); 6.96-6.83 (2
H, m); 5.49 (2H, s); 4.59-4.50 (1H, br.m); 4.38-4.
12 (1H, m); 3.95-3.18 (7H, m); 2.21 (3H, br.s); 1.
75 (3H, s); 1.80-1.35 (4H, m). Working Example 227 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- [2- (tetrahydropyra
N-2-yloxy) ethyl] acetamide (Compound No.
No. D1.118) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
d, J = 7.2 Hz); 7.92 (1H, d, J = 5.9 Hz); 7.56-7.37 (2
H, m); 7.12 (1H, dd, J = 8.5 & 5.4 Hz); 6.96-6.83 (2
H, m); 5.49 (2H, s); 4.59-4.50 (1H, br.m); 4.38-4.
12 (1H, m); 3.95-3.18 (7H, m); 2.21 (3H, br.s); 1.
75 (3H, s); 1.80-1.35 (4H, m).

【０５３１】[0531]

【実施例２２８】Ｎ−アセチル−Ｎ−［４−（ベンゾチアゾール−２−イ
ルメトキシ）−２−メチルフェニル］アセトアミド（化
合物番号D2.1）融点：119 −121 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=8.2 Hz); 7.92 (1H,dd, J=7.7 & 1.6 Hz); 7.53-
7.42 (2H, m); 6.99-6.96 (3H, m); 5.49 (2H, s); 2.2
7 (6H, s); 2.13 (3H, s).Working Example 228 N-acetyl-N- [4- (benzothiazol-2-i
Rumethoxy) -2-methylphenyl] acetamide
Compound No. D2.1) Melting point: 119-121 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 8.2 Hz); 7.92 (1H, dd, J = 7.7 & 1.6 Hz); 7.53-
7.42 (2H, m); 6.99-6.96 (3H, m); 5.49 (2H, s); 2.2
7 (6H, s); 2.13 (3H, s).

【０５３２】[0532]

【実施例２２９】Ｎ−アセチル−Ｎ−［４−（ベンゾチアゾール−２−イ
ルメトキシ）−２−メチルフェニル］ブチルアミド（化
合物番号D2.6）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.4 Hz); 7.91 (1H,d, J=7.7 Hz); 7.54-7.41 (2
H, m); 7.01-6.95 (3H, m); 5.49 (3H, s); 2.53-2.36
(2H, m); 2.32 (3H, s); 2.11 (3H, s); 1.63 (2H, q,
J=7.2 Hz); 0.89 (3H, t, J=7.2 Hz).Working Example 229 N-acetyl-N- [4- (benzothiazol-2-i
Rumethoxy) -2-methylphenyl] butyramide
Compound No.D2.6) Oil NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.04 (1H,
d, J = 7.4 Hz); 7.91 (1H, d, J = 7.7 Hz); 7.54-7.41 (2
H, m); 7.01-6.95 (3H, m); 5.49 (3H, s); 2.53-2.36
(2H, m); 2.32 (3H, s); 2.11 (3H, s); 1.63 (2H, q,
J = 7.2 Hz); 0.89 (3H, t, J = 7.2 Hz).

【０５３３】[0533]

【実施例２３０】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−エトキシカルボニルプロピ
オンアミド（化合物番号D2.19 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.0 Hz); 7.90 (1H,dd, J=8.4 & 1.5 Hz); 7.54-
7.39 (2H, m); 6.98-6.90 (3H, m); 5.47 (2H, s); 4.2
1-4.13 (2H, m); 3.03-2.91 (2H, m); 2.09 (3H, s);
1.25-1.13 (6H, m). Working Example 230 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-ethoxycarbonylpropyl
Onamide (Compound No. D2.19) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.0 Hz); 7.90 (1H, dd, J = 8.4 & 1.5 Hz); 7.54-
7.39 (2H, m); 6.98-6.90 (3H, m); 5.47 (2H, s); 4.2
1-4.13 (2H, m); 3.03-2.91 (2H, m); 2.09 (3H, s);
1.25-1.13 (6H, m).

【０５３４】[0534]

【実施例２３１】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２−
エトキシアセトアミド（化合物番号D2.20 ）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H, d
d, J=7.2 & 1.3 Hz); 7.91 (1H, dd, J=7.2 & 1.3 Hz);
7.51 (1H, td, J=7.2 & 1.3 Hz); 7.41 (1H, td, J=7.
2 & 1.3 Hz); 6.99-6.87 (3H, m); 5.47 (2H, s); 4.75
(2H, s); 3.71 (3H, s); 3.62 (2H, q, J=7.0 Hz); 2.
10 (3H, s); 1.26 (3H, t, J=7.0 Hz). Working Example 231 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2-
Ethoxyacetamide (Compound No. D2.20) amorphous NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.04 (1H, d
d, J = 7.2 & 1.3 Hz); 7.91 (1H, dd, J = 7.2 & 1.3 Hz);
7.51 (1H, td, J = 7.2 & 1.3 Hz); 7.41 (1H, td, J = 7.
2 & 1.3 Hz); 6.99-6.87 (3H, m); 5.47 (2H, s); 4.75
(2H, s); 3.71 (3H, s); 3.62 (2H, q, J = 7.0 Hz); 2.
10 (3H, s); 1.26 (3H, t, J = 7.0 Hz).

【０５３５】[0535]

【実施例２３２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２−
ブテンアミド（化合物番号D2.21 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.2 Hz); 7.90 (1H,d, J=7.6 Hz); 7.53-7.40 (2
H, m); 7.14-6.75 (5H, m); 5.47 (2H, s); 3.73(3H,
s); 2.11 (3H, s); 1.91 (3H, dd, J=6.8 & 1.5 Hz). Working Example 232 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2-
Butenamide (Compound No. D2.21) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.2 Hz); 7.90 (1H, d, J = 7.6 Hz); 7.53-7.40 (2
H, m); 7.14-6.75 (5H, m); 5.47 (2H, s); 3.73 (3H,
s); 2.11 (3H, s); 1.91 (3H, dd, J = 6.8 & 1.5 Hz).

【０５３６】[0536]

【実施例２３３】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−３−
メチル−２−ブテンアミド（化合物番号D2.22 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
２（１Ｈ，ｄ，Ｊ＝８．１Ｈｚ）；７．８８
（１Ｈ，ｄ，Ｊ＝８．０Ｈｚ）；７．５２−
７．３７（２Ｈ，ｍ）；７．０２−６．８８
（３Ｈ，ｍ）；６．４９（１Ｈ，ｂｒ．ｓ）；
５．４５（２Ｈ，ｓ）；３．７０（３Ｈ，
ｓ）；２．１２（６Ｈ，ｓ）；１．９３（３
Ｈ，ｂｒ．ｓ）． Working Example 233 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-3-
Methyl-2-butenamide (Compound No. D2.22) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
2. (1H, d, J = 8.1 Hz); 7.88
(1H, d, J = 8.0 Hz); 7.52-
7.37 (2H, m); 7.02-6.88.
(3H, m); 6.49 (1H, br.s);
5.45 (2H, s); 3.70 (3H,
2.12 (6H, s); 1.93 (3
H, br. s).

【０５３７】[0537]

【実施例２３４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−エトキシカルボニル−２−
メトキシアセトアミド（化合物番号Ｄ２．２３）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=8.8 Hz); 7.92 (1H,dd, J=7.3 & 1.5 Hz); 7.55-
7.41 (2H, m); 6.99-6.91 (3H, m); 5.48 (2H, s); 4.7
0 (2H, s); 4.22-4.11 (2H, m); 3.48 (3H, s); 2.10
(3H, s); 1.17 (3H,t, J=7.1 Hz). Working Example 234 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-ethoxycarbonyl-2-
Methoxyacetamide (Compound No. D2.23) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 8.8 Hz); 7.92 (1H, dd, J = 7.3 & 1.5 Hz); 7.55-
7.41 (2H, m); 6.99-6.91 (3H, m); 5.48 (2H, s); 4.7
0 (2H, s); 4.22-4.11 (2H, m); 3.48 (3H, s); 2.10
(3H, s); 1.17 (3H, t, J = 7.1 Hz).

【０５３８】[0538]

【実施例２３５】Ｎ−アセチル−Ｎ−［４−（ベンゾチアゾール−２−イ
ルメトキシ）−２−メチルフェニル］−２−メトキシア
セトアミド（化合物番号D2.25 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=7.2 Hz); 7.92 (1H,dd, J=7.8 & 1.8 Hz); 7.55-
7.42 (2H, m); 7.04-6.96 (3H, m); 5.50 (2H, s); 4.3
7 (2H, q, J=17.6 Hz); 3.44 (3H, s); 2.17 (2H, s);
2.13 (6H, s).Working Example 235 N-acetyl-N- [4- (benzothiazol-2-i
Methoxy) -2-methylphenyl] -2-methoxya
Cetamide (Compound No. D2.25) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
d, J = 7.2 Hz); 7.92 (1H, dd, J = 7.8 & 1.8 Hz); 7.55-
7.42 (2H, m); 7.04-6.96 (3H, m); 5.50 (2H, s); 4.3
7 (2H, q, J = 17.6 Hz); 3.44 (3H, s); 2.17 (2H, s);
2.13 (6H, s).

【０５３９】[0539]

【実施例２３６】Ｎ−アセチル−Ｎ−［４−（ベンゾチアゾール−２−イ
ルメトキシ）−２−メチルフェニル］−３−メトキシプ
ロピオンアミド（化合物番号D2.29 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-8.02
(1H, m); 7.93-7.90 (1H,m); 7.56-7.42 (2H, m); 7.03
-6.95 (3H, m); 5.49 (2H, s); 3.64 (2H, t, J=5.9 H
z); 3.32 (3H, s); 2.76-2.63 (2H, m); 2.35 (3H, s);
2.13 (3H, s).Working Example 236 N-acetyl-N- [4- (benzothiazol-2-i
Methoxy) -2-methylphenyl] -3-methoxyprop
Lopionamide (Compound No. D2.29) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-8.02
(1H, m); 7.93-7.90 (1H, m); 7.56-7.42 (2H, m); 7.03
-6.95 (3H, m); 5.49 (2H, s); 3.64 (2H, t, J = 5.9 H
z); 3.32 (3H, s); 2.76-2.63 (2H, m); 2.35 (3H, s);
2.13 (3H, s).

【０５４０】[0540]

【実施例２３７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−３−
メトキシプロピオンアミド（化合物番号D2.30 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.7 Hz); 7.91 (1H,dd, J=6.8 & 0.9 Hz); 7.55-
7.41 (2H, m); 6.99-6.90 (3H, m); 5.47 (2H, s); 3.7
4 (2H, t, J=6.2 Hz); 3.72 (3H, s); 3.35 (3H, s);
3.32-3.18 (2H, s);2.10 (3H, s). Working Example 237 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-3-
Methoxypropionamide (Compound No. D2.30) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.7 Hz); 7.91 (1H, dd, J = 6.8 & 0.9 Hz); 7.55-
7.41 (2H, m); 6.99-6.90 (3H, m); 5.47 (2H, s); 3.7
4 (2H, t, J = 6.2 Hz); 3.72 (3H, s); 3.35 (3H, s);
3.32-3.18 (2H, s); 2.10 (3H, s).

【０５４１】[0541]

【実施例２３８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−３−
エトキシプロピオンアミド（化合物番号D2.32 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.9 Hz); 7.91 (1H,d, J=7.9 Hz); 7.37-7.56 (2
H, m); 6.86-7.00 (3H, m); 5.47 (2H, s); 3.77(2H,
t, J=6.2 Hz); 3.72 (3H, s); 3.51 (2H, q, J=7.0 H
z); 3.22 (2H, m); 2.11 (3H, s); 1.18 (3H, t, J=7.0
Hz). Working Example 238 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-3-
Ethoxypropionamide (Compound No. D2.32) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.9 Hz); 7.91 (1H, d, J = 7.9 Hz); 7.37-7.56 (2
H, m); 6.86-7.00 (3H, m); 5.47 (2H, s); 3.77 (2H,
t, J = 6.2 Hz); 3.72 (3H, s); 3.51 (2H, q, J = 7.0 H
z); 3.22 (2H, m); 2.11 (3H, s); 1.18 (3H, t, J = 7.0
Hz).

【０５４２】[0542]

【実施例２３９】Ｎ−アセチル−Ｎ−［４−（ベンゾチアゾール−２−イ
ルメトキシ）−２−メチルフェニル］ベンズアミド（化
合物番号D2.41 ）融点：111 −113 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.7 Hz); 7.91 (1H,d, J=7.7 Hz); 7.58-7.28 (7
H, m); 7, 03 (1H, d, J=8.5 Hz); 6.93-6.84 (2H, m);
5.44 (2H, s); 2.35 (3H, s); 2.24 (3H, s).Working Example 239 N-acetyl-N- [4- (benzothiazol-2-i
Rumethoxy) -2-methylphenyl] benzamide
Compound No. D2.41) Melting point: 111-113 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.7 Hz); 7.91 (1H, d, J = 7.7 Hz); 7.58-7.28 (7
H, m); 7, 03 (1H, d, J = 8.5 Hz); 6.93-6.84 (2H, m);
5.44 (2H, s); 2.35 (3H, s); 2.24 (3H, s).

【０５４３】[0543]

【実施例２４０】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−４−
ｔ−ブチルベンズアミド（化合物番号D2.45 ）融点：130 −131.5 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.5 Hz); 7.92 (1H,dd, J=8.0 & 1.1 Hz); 7.66
(2H, d, J=8.5 Hz); 7.54-7.37 (4H, m); 7.12 (1H, d,
J=8.5 Hz); 6.99-6.89 (2H, m); 5.49 (2H, s); 3.67
(3H, s); 2.27 (3H, s); 1.34 (9H, s). Working Example 240 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-4-
t-Butylbenzamide (Compound No. D2.45) Melting point: 130-131.5 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.5 Hz); 7.92 (1H, dd, J = 8.0 & 1.1 Hz); 7.66
(2H, d, J = 8.5 Hz); 7.54-7.37 (4H, m); 7.12 (1H, d,
J = 8.5 Hz); 6.99-6.89 (2H, m); 5.49 (2H, s); 3.67
(3H, s); 2.27 (3H, s); 1.34 (9H, s).

【０５４４】[0544]

【実施例２４１】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２−
クロロベンズアミド（化合物番号D2.46 ）融点：136 −137 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=8.1 Hz); 7.92 (1H,d, J=7.3 Hz); 7.56-7.35 (6
H, m); 7.20 (1H, d, J=8.5 Hz); 7.02-6.95 (2H,m);
5.51 (2H, s); 3.64 (3H, s); 2.27 (3H, s). Working Example 241 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2-
Chlorobenzamide (Compound No. D2.46) Melting point: 136-137 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
d, J = 8.1 Hz); 7.92 (1H, d, J = 7.3 Hz); 7.56-7.35 (6
H, m); 7.20 (1H, d, J = 8.5 Hz); 7.02-6.95 (2H, m);
5.51 (2H, s); 3.64 (3H, s); 2.27 (3H, s).

【０５４５】[0545]

【実施例２４２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−３−
クロロベンズアミド（化合物番号D2.47 ）融点：108.5 −110.5 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=8.1 Hz); 7.92 (1H,d, J=8.0 Hz); 7.65-7.33 (6
H, m); 7.11 (1H, d, J=8.4 Hz); 6.98-6.90 (2H,m);
5.49 (2H, s); 3.68 (3H, s); 2.26 (3H, s). Working Example 242 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-3-
Chlorobenzamide (Compound No. D2.47) Melting point: 108.5-110.5 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.05 (1H,
d, J = 8.1 Hz); 7.92 (1H, d, J = 8.0 Hz); 7.65-7.33 (6
H, m); 7.11 (1H, d, J = 8.4 Hz); 6.98-6.90 (2H, m);
5.49 (2H, s); 3.68 (3H, s); 2.26 (3H, s).

【０５４６】[0546]

【実施例２４３】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−４−
クロロベンズアミド（化合物番号D2.48 ）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
４（１Ｈ，ｄｄ，Ｊ＝８．０＆０．８Ｈ
ｚ）；７．９０（１Ｈ，ｄｄ，Ｊ＝８．３＆
１．５Ｈｚ）；７．６３（２Ｈ，ｄ，Ｊ＝
８．５Ｈｚ）；７．５４−７．３６（４Ｈ，
ｍ）；７．１０（１Ｈ，ｄ，Ｊ＝８．６Ｈ
ｚ）；６．９９−６．９５（２Ｈ，ｍ）；５．
４７（２Ｈ，ｓ）；３．６７（３Ｈ，ｓ）；
２．２５（３Ｈ，ｓ）． Working Example 243 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-4-
Chlorobenzamide (Compound No. D2.48) amorphous NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
4 (1H, dd, J = 8.0 & 0.8 H
7.90 (1H, dd, J = 8.3 &
7.63 (2H, d, J =
7.54-7.36 (4H,
m); 7.10 (1H, d, J = 8.6H)
6.99-6.95 (2H, m);
47 (2H, s); 3.67 (3H, s);
2.25 (3H, s).

【０５４７】[0547]

【実施例２４４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２，
６−ジクロロベンズアミド（化合物番号Ｄ２．５０）融点：191 −193 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=7.7 Hz); 7.92 (1H,dd, J=7.4 & 1.3 Hz); 7.56-
7.19 (6H, m); 7.04-6.95 (2H, m); 5.51 (2H, s); 3.6
5 (3H, s); 2.30 (3H, s). Working Example 244 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2,
6-dichlorobenzamide (Compound No. D2.50) Melting point: 191-193 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
d, J = 7.7 Hz); 7.92 (1H, dd, J = 7.4 & 1.3 Hz); 7.56-
7.19 (6H, m); 7.04-6.95 (2H, m); 5.51 (2H, s); 3.6
5 (3H, s); 2.30 (3H, s).

【０５４８】[0548]

【実施例２４５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−３，
４−ジクロロベンズアミド（化合物番号D2.51 ）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.3 Hz); 7.90 (1H,d, J=8.1 Hz); 7.75 (1H, d,
J=1.4 Hz); 7.54-7.36 (4H, m); 7.09 (1H, d, J=8.4 H
z); 6.97-6.90 (2H, m); 5.48 (2H, s); 3.68 (3H, s);
2.24 (3H, s). Working Example 245 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-3,
4-Dichlorobenzamide (Compound No. D2.51) amorphous NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.3 Hz); 7.90 (1H, d, J = 8.1 Hz); 7.75 (1H, d,
J = 1.4 Hz); 7.54-7.36 (4H, m); 7.09 (1H, d, J = 8.4 H
z); 6.97-6.90 (2H, m); 5.48 (2H, s); 3.68 (3H, s);
2.24 (3H, s).

【０５４９】[0549]

【実施例２４６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２，
６−ジフルオロベンズアミド（化合物番号D2.53）融点：151 −152.5 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=7.5 Hz); 7.92 (1H,d, J=7.3 Hz); 7.56-7.31 (3
H, m); 7.14 (1H, d, J=8.6 Hz); 7.02-6.92 (4H,m);
5.50 (2H, s); 3.67 (3H, s); 2.25 (3H, s). Working Example 246 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2,
6-difluorobenzamide (Compound No. D2.53) Melting point: 151-152.5 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
d, J = 7.5 Hz); 7.92 (1H, d, J = 7.3 Hz); 7.56-7.31 (3
H, m); 7.14 (1H, d, J = 8.6 Hz); 7.02-6.92 (4H, m);
5.50 (2H, s); 3.67 (3H, s); 2.25 (3H, s).

【０５５０】[0550]

【実施例２４７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−３−
メトキシベンズアミド（化合物番号D2.56 ）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.6 Hz); 7.90 (1H,d, J=7.7 Hz); 7.55-7.22 (5
H, m); 7.13-6.89 (4H, m); 5.48 (2H, s); 3.82(3H,
s); 3.65 (3H, s); 2.27 (3H, s). Working Example 247 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-3-
Methoxybenzamide (Compound No. D2.56) amorphous NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.04 (1H,
d, J = 7.6 Hz); 7.90 (1H, d, J = 7.7 Hz); 7.55-7.22 (5
H, m); 7.13-6.89 (4H, m); 5.48 (2H, s); 3.82 (3H,
s); 3.65 (3H, s); 2.27 (3H, s).

【０５５１】[0551]

【実施例２４８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−４−
メトキシベンズアミド（化合物番号D2.57 ）融点：126 −128 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.6 Hz); 7.90 (1H,d, J=8.6 Hz); 7.71 (2H, d,
J=8.6 Hz); 7.53-7.39 (2H, m); 7.11 (1H, d, J=8.4 H
z); 6.96-6.89 (4H, m); 5.46 (2H, s); 3.84 (3H, s);
3.68 (3H, s); 2.26 (3H, s). Working Example 248 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-4-
Methoxybenzamide (Compound No. D2.57) Melting point: 126-128 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.6 Hz); 7.90 (1H, d, J = 8.6 Hz); 7.71 (2H, d,
J = 8.6 Hz); 7.53-7.39 (2H, m); 7.11 (1H, d, J = 8.4 H
z); 6.96-6.89 (4H, m); 5.46 (2H, s); 3.84 (3H, s);
3.68 (3H, s); 2.26 (3H, s).

【０５５２】[0552]

【実施例２４９】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２−
メチルベンズアミド（化合物番号D2.60 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.7 Hz); 7.90 (1H,d, J=7.4 Hz); 7.54-7.18 (6
H, m); 7.13 (1H, d, J=8.6 Hz); 7.01-6.92 (2H,m);
5.49 (2H, s); 3.58 (3H, s); 2.45 (3H, s); 2.27 (3
H, s). Working Example 249 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2-
Methylbenzamide (Compound No.D2.60) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.7 Hz); 7.90 (1H, d, J = 7.4 Hz); 7.54-7.18 (6
H, m); 7.13 (1H, d, J = 8.6 Hz); 7.01-6.92 (2H, m);
5.49 (2H, s); 3.58 (3H, s); 2.45 (3H, s); 2.27 (3
H, s).

【０５５３】[0553]

【実施例２５０】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−（２−フロイル）アセトア
ミド（化合物番号D2.63 ）油状物ＮＭＲスペクトル(200MzCDCl₃), δｐｐｍ：８．０７
−８．０２（１Ｈ，ｍ）；７．９５−７．９０
（１Ｈ，ｍ）；７．５３−７．４２（３Ｈ，
ｍ）；７．０８−６．９５（３Ｈ，ｍ）；６．
３２−６．２９（１Ｈ，ｍ）；６．１３−６．１
１（１Ｈ，ｍ）；５．４９（２Ｈ，ｓ）；
２．５６（３Ｈ，ｓ）；２．１７（３Ｈ，
ｓ）． Working Example 250 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- (2-furoyl) acetoa
Mide (Compound No. D2.63) Oil NMR spectrum (200 MzCDCl ₃ ), δ ppm: 8.07
-8.02 (1H, m); 7.95-7.90
(1H, m); 7.53-7.42 (3H,
m); 7.08-6.95 (3H, m);
32-6.29 (1H, m); 6.13-6.1.
1 (1H, m); 5.49 (2H, s);
2.56 (3H, s); 2.17 (3H, s)
s).

【０５５４】[0554]

【実施例２５１】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−メチルフェニル］−Ｎ−メトキシカルボニルフラ
ン−２−カルボキサミド（化合物番号Ｄ２．６５）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H,m); 7.51 (1H, d, J=0.7 Hz);
7.40-7.36 (2H, m); 7.13 (1H, d, J=8.5 Hz);6.99-6.
94 (2H, m); 6.91 (2H, d, J=3.6 Hz); 6.47 (1H, dd,
J=3.6 & 1.7 Hz); 5.33 (2H, s); 3.77 (3H, s); 2.23
(3H, s). Working Example 251 N- [4- (benzoxazol-2-ylmethoxy)
-2-methylphenyl] -N-methoxycarbonylfura
2-Carboxamide (Compound No. D2.65) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H, m); 7.51 (1H, d, J = 0.7 Hz);
7.40-7.36 (2H, m); 7.13 (1H, d, J = 8.5 Hz); 6.99-6.
94 (2H, m); 6.91 (2H, d, J = 3.6 Hz); 6.47 (1H, dd,
J = 3.6 & 1.7 Hz); 5.33 (2H, s); 3.77 (3H, s); 2.23
(3H, s).

【０５５５】[0555]

【実施例２５２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニルチオフ
ェン−２−カルボキサミド（化合物番号D2.66 ）ガム状ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.2 Hz); 7.92 (1H,dd, J=1.6 & 7.2 Hz); 7.38-
7.55 (4H, m); 7.14 (1H, d, J=8.6 Hz); 6.87-7.01 (3
H, m); 5.49 (2H, s); 3.80 (3H, s); 2.25 (3H, s). Working Example 252 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylthiof
2-Carboxamide (Compound No. D2.66) gum NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.2 Hz); 7.92 (1H, dd, J = 1.6 & 7.2 Hz); 7.38-
7.55 (4H, m); 7.14 (1H, d, J = 8.6 Hz); 6.87-7.01 (3
H, m); 5.49 (2H, s); 3.80 (3H, s); 2.25 (3H, s).

【０５５６】[0556]

【実施例２５３】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−（２−テノイル）アセトア
ミド（化合物番号D2.67 ）油状物ＮＭＲスペクトル(200MzCDCl₃), δppm: 8.07-8.02 (1
H, m); 7.95-7.91 (1H, m); 7.53-7.42 (3H, m); 7.19-
6.87 (5H, m); 5.50 (2H, s); 2.63 (3H, s); 2.17 (3
H, s). Working Example 253 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- (2-thenoyl) acetoa
Amide (Compound No.D2.67) oil NMR spectrum (200 MzCDCl ₃ ), δ ppm: 8.07-8.02 (1
H, m); 7.95-7.91 (1H, m); 7.53-7.42 (3H, m); 7.19-
6.87 (5H, m); 5.50 (2H, s); 2.63 (3H, s); 2.17 (3
H, s).

【０５５７】[0557]

【実施例２５４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニルニコチ
ンアミド（化合物番号D2.68 ）融点：104 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.89 (1H,
m); 8.72 (1H, dd, J=1.4& 4.9 Hz); 7.87-8.06 (3H,
m); 7.34-7.56 (3H, m); 7.11 (1H, d, J=8.4 Hz); 6.8
9-6.99 (2H, m); 5.49 (2H, s); 3.68 (3H, m); 2.26
(3H, s). Working Example 254 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylnicotine
Amide (Compound No. D2.68) melting point: 104 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.89 (1H,
m); 8.72 (1H, dd, J = 1.4 & 4.9 Hz); 7.87-8.06 (3H,
m); 7.34-7.56 (3H, m); 7.11 (1H, d, J = 8.4 Hz); 6.8
9-6.99 (2H, m); 5.49 (2H, s); 3.68 (3H, m); 2.26
(3H, s).

【０５５８】[0558]

【実施例２５５】Ｎ−｛４−［１−( ベンゾチアゾール−２−イル）プロ
ポキシ］−２−メチルフェニル｝−Ｎ−エチルアセトア
ミド（化合物番号E7.10 ）油状物ＮＭＲスペクトル(200Mz,CDCl₃),δppm: 8.03 (1H, dd,
J=7.4 & 1.4 Hz); 7.87(1H, dd, J=7.4 & 1.4 Hz); 7.
50 (1H, td, J=7.4 & 1.4 Hz); 7.39 (1H, td,J=7.4 &
1.4 Hz); 6.93 (1H, d, J=2.4 Hz); 6.92 (1H, d, J=8.
6 Hz); 6.83 (1H, dd, J=8.6 & 2.4 Hz); 5.50 (1H, d
d, J=7.0 & 5.6 Hz); 4.10-3.93 (1H, m); 3.25-3.08
(1H, m); 2.26-2.09 (2H, m); 2.14 (3H, s); 1.70 (3
H, d, J=1.3Hz); 1.13 (3H, t, J=7.3 Hz); 1.07 (3H,
td, J=7.2 & 2.2 Hz).Working Example 255 N- {4- [1- (Benzothiazol-2-yl) pro]
Poxy] -2-methylphenyl} -N-ethylacetoa
Amide (Compound No.E7.10) oil NMR spectrum (200 Mz, CDCl ₃ ), δ ppm: 8.03 (1H, dd,
J = 7.4 & 1.4 Hz); 7.87 (1H, dd, J = 7.4 & 1.4 Hz); 7.87
50 (1H, td, J = 7.4 & 1.4 Hz); 7.39 (1H, td, J = 7.4 &
1.4 Hz); 6.93 (1H, d, J = 2.4 Hz); 6.92 (1H, d, J = 8.
6 Hz); 6.83 (1H, dd, J = 8.6 & 2.4 Hz); 5.50 (1H, d
d, J = 7.0 & 5.6 Hz); 4.10-3.93 (1H, m); 3.25-3.08
(1H, m); 2.26-2.09 (2H, m); 2.14 (3H, s); 1.70 (3
H, d, J = 1.3Hz); 1.13 (3H, t, J = 7.3 Hz); 1.07 (3H,
td, J = 7.2 & 2.2 Hz).

【０５５９】[0559]

【実施例２５６】プロピルＮ−［４−（ベンゾチアゾール−２−イルメ
トキシ）フェニル］カルバマート（化合物番号A1.25 ）融点：159 −163 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H, d
d, J=8.3 & 0.9 Hz); 7.90 (1H, dd, J=7.1 & 1.1 Hz);
7.53-7.40 (2H, m); 7.15 (4H, m); 6.46 (1H,br.s);
5.46 (2H, s); 4.11 (2H, t, J=6.7 Hz); 1.69 (2H, se
xtet, J=6.7 Hz); 0.96 (3H, t, J=6.7 Hz). Working Example 256 Propyl N- [4- (benzothiazol-2-ylmethine)
Toxi) phenyl] carbamate (Compound No. A1.25) Melting point: 159-163 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H, d
d, J = 8.3 & 0.9 Hz); 7.90 (1H, dd, J = 7.1 & 1.1 Hz);
7.53-7.40 (2H, m); 7.15 (4H, m); 6.46 (1H, br.s);
5.46 (2H, s); 4.11 (2H, t, J = 6.7 Hz); 1.69 (2H, se
xtet, J = 6.7 Hz); 0.96 (3H, t, J = 6.7 Hz).

【０５６０】[0560]

【実施例２５７】イソプロピルＮ−［４−（ベンゾチアゾール−２−イ
ルメトキシ）フェニル］カルバマート（化合物番号A1.2
8 ）融点：176 −178 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.2 Hz); 7.90 (1H,dd, J=8.0 & 0.9 Hz); 7.54-
7.36 (2H, m); 7.20 (4H, m); 6.41 (1H, br.s);5.46
(2H, s); 5.00 (1H, heptet, J=6.3 Hz); 1.29 (6H, d,
J=6.3 Hz).Working Example 257 Isopropyl N- [4- (benzothiazole-2-i
Rumethoxy) phenyl] carbamate (Compound No. A1.2
8) Melting point: 176-178 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.03 (1H,
d, J = 8.2 Hz); 7.90 (1H, dd, J = 8.0 & 0.9 Hz); 7.54-
7.36 (2H, m); 7.20 (4H, m); 6.41 (1H, br.s); 5.46
(2H, s); 5.00 (1H, heptet, J = 6.3 Hz); 1.29 (6H, d,
J = 6.3 Hz).

【０５６１】[0561]

【実施例２５８】ブチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）フェニル］カルバマート（化合物番号A1.31 ）融点：149 −152 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H.d,
J=7.5 Hz); 7.90 (1H,dd, J=7.9 &1.5 Hz); 7.54-7.36
(2H, m); 7.15 (4H, m); 6.45 (1H, br.s); 5.46 (2H,
s); 4.15 (2H, t, J=6.6 Hz); 1.61 (2H, quintet, J=
4.5 Hz); 1.41 (2H, sextet, J=7.0 Hz); 0.94 (3H, t,
J=7.3 Hz). Working Example 258: Butyl N- [4- (benzothiazol-2-ylmethoate)
Xy) phenyl] carbamate (Compound No. A1.31) Melting point: 149 ° -152 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H.d,
J = 7.5 Hz); 7.90 (1H, dd, J = 7.9 & 1.5 Hz); 7.54-7.36
(2H, m); 7.15 (4H, m); 6.45 (1H, br.s); 5.46 (2H,
s); 4.15 (2H, t, J = 6.6 Hz); 1.61 (2H, quintet, J =
4.5 Hz); 1.41 (2H, sextet, J = 7.0 Hz); 0.94 (3H, t,
J = 7.3 Hz).

【０５６２】[0562]

【実施例２５９】２，２，２−トリクロロエチルＮ−［４−（ベンゾチ
アゾール−２−イルメトキシ）フェニル］カルバマート
（化合物番号A1.56 ）融点：153 −154 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.1 Hz); 7.90 (1H,dd, J=6.7 & 0.7 Hz); 7.51-
7.32 (4H, m); 7.03 (2H, d, J=9.1 Hz); 6.78 (1H, b
r.s); 5.48 (2H, s); 4.81 (2H, s). Working Example 259 2,2,2-Trichloroethyl N- [4- (benzothi
Azol-2-ylmethoxy) phenyl] carbamate
(Compound No. A1.56) Melting point: 153-154 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.1 Hz); 7.90 (1H, dd, J = 6.7 & 0.7 Hz); 7.51-
7.32 (4H, m); 7.03 (2H, d, J = 9.1 Hz); 6.78 (1H, b
rs); 5.48 (2H, s); 4.81 (2H, s).

【０５６３】[0563]

【実施例２６０】Ｓ−メチルＮ−［４−（ベンゾチアゾール−２−イル
メトキシ）−２−メチルフェニル］チオカルバマート
（化合物番号C1.11 ）融点：145 −147 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
６−８．０１（１Ｈ，ｍ）；７．９２−７．８８
（１Ｈ，ｍ）；７．５１−７．３７（３Ｈ，
ｍ）；６．９２−６．８６（２Ｈ，ｍ）；６．
７３（１Ｈ，ｂｒ．ｓ）；５．４７（２Ｈ，
ｓ）；２．３６（３Ｈ，ｓ）；２．２６（３
Ｈ，ｓ）． Working Example 260 S-methyl N- [4- (benzothiazol-2-yl)
Methoxy) -2-methylphenyl] thiocarbamate
(Compound No. C1.11) Melting point: 145-147 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
6-8.01 (1H, m); 7.92-7.88
(1H, m); 7.51-7.37 (3H,
6.92-6.86 (2H, m);
73 (1H, br.s);
2.36 (3H, s); 2.26 (3
H, s).

【０５６４】[0564]

【実施例２６１】エチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］カルバマート（化合物番
号Ｃ１．１７）融点：124 −127 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.2 Hz); 7.90 (1H,d, J=6.9 Hz); 7.55-7.36 (3
H, m); 6.91-6.84 (2H, m); 6.19 (1H, br.s); 5.46 (2
H, s); 4.21 (2H, q, J=7.1 Hz); 2.24 (3H, s); 1.30
(3H, t, J=7.1 Hz). Working Example 261 Ethyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] carbamate (compound number
No. C1.17) Melting point: 124-127 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.2 Hz); 7.90 (1H, d, J = 6.9 Hz); 7.55-7.36 (3
H, m); 6.91-6.84 (2H, m); 6.19 (1H, br.s); 5.46 (2
H, s); 4.21 (2H, q, J = 7.1 Hz); 2.24 (3H, s); 1.30
(3H, t, J = 7.1 Hz).

【０５６５】[0565]

【実施例２６２】２，２，２−トリクロロエチルＮ−［４−（ベンゾチ
アゾール−２−イルメトキシ）−２−メチルフェニル］
カルバマート（化合物番号C1.19 ）融点：166 −168 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.3 Hz); 7.90 (1H,dd, J=6.9 & 0.8 Hz); 7.54-
7.36 (3H, m); 6.91-6.87 (2H, m); 6.49 (1H, br.s);
5.47 (2H, s); 4.81 (2H, s); 2.28 (3H, s). Working Example 262 2,2,2-Trichloroethyl N- [4- (benzothienyl)
Azol-2-ylmethoxy) -2-methylphenyl]
Carbamate (Compound No. C1.19) Melting point: 166-168 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.3 Hz); 7.90 (1H, dd, J = 6.9 & 0.8 Hz); 7.54-
7.36 (3H, m); 6.91-6.87 (2H, m); 6.49 (1H, br.s);
5.47 (2H, s); 4.81 (2H, s); 2.28 (3H, s).

【０５６６】[0566]

【実施例２６３】イソプロピルＮ−［４−（ベンゾチアゾール−２−イ
ルメトキシ）−２−メチルフェニル］カルバマート（化
合物番号C1.23 ）融点：118 −120 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H, d
d, J=8.9 & 1.6 Hz); 7.90 (1H, dd, J=7.1 & 1.5 Hz);
7.62-7.36 (3H, m); 6.89-6.86 (2H, m); 6.14(1H, b
r.s); 5.46 (2H, s); 4.99 (1H, heptet, J=6.2 Hz);
2.24 (3H, s); 1.29 (6H, d, J=6.2 Hz).Working Example 263 Isopropyl N- [4- (benzothiazole-2-i
Rumethoxy) -2-methylphenyl] carbamate
Compound No. C1.23) Melting point: 118-120 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H, d
d, J = 8.9 & 1.6 Hz); 7.90 (1H, dd, J = 7.1 & 1.5 Hz);
7.62-7.36 (3H, m); 6.89-6.86 (2H, m); 6.14 (1H, b
rs); 5.46 (2H, s); 4.99 (1H, heptet, J = 6.2 Hz);
2.24 (3H, s); 1.29 (6H, d, J = 6.2 Hz).

【０５６７】[0567]

【実施例２６４】プロピルＮ−［４−（ベンゾチアゾール−２−イルメ
トキシ）−２−メチルフェニル］カルバマート（化合物
番号C1.24 ）融点：121 −124 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.3 Hz); 7.90 (1H,d, J=6.9 Hz); 7.62-7.36 (3
H, m); 6.91-6.84 (2H, m); 6.19 (1H, br.s); 5.45 (2
H, s); 4.11 (2H, d, J=6.8 Hz); 2.24 (3H, s); 1.69
(2H, sextet, J=6.8 Hz); 0.97 (3H, t, J=6.8 Hz). Working Example 264: Propyl N- [4- (benzothiazol-2-ylmeth)
Toxi) -2-methylphenyl] carbamate (compound
No. C1.24) melting point: 121-124 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.3 Hz); 7.90 (1H, d, J = 6.9 Hz); 7.62-7.36 (3
H, m); 6.91-6.84 (2H, m); 6.19 (1H, br.s); 5.45 (2
H, s); 4.11 (2H, d, J = 6.8 Hz); 2.24 (3H, s); 1.69
(2H, sextet, J = 6.8 Hz); 0.97 (3H, t, J = 6.8 Hz).

【０５６８】[0568]

【実施例２６５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−２，２−ジメチルプロピオンア
ミド（化合物番号C1.27 ）融点：140 −142 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.0 Hz); 7.89 (1H,d, J=7.2 Hz); 7.63 (1H, d,
J=9.4 Hz); 7.35-7.53 (2H, m); 7.09 (1H, br.s); 6.8
4-6.91 (2H, m); 5.46 (2H, s); 2.22 (3H, s); 1.33
(9H, s). Working Example 265 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -2,2-dimethylpropiona
Mide (Compound No. C1.27) Melting point: 140-142 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.0 Hz); 7.89 (1H, d, J = 7.2 Hz); 7.63 (1H, d,
J = 9.4 Hz); 7.35-7.53 (2H, m); 7.09 (1H, br.s); 6.8
4-6.91 (2H, m); 5.46 (2H, s); 2.22 (3H, s); 1.33
(9H, s).

【０５６９】[0569]

【実施例２６６】ブチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］カルバマート（化合物番
号C1.28 ）融点：127 −128 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.2 Hz); 7.90 (1H,dd, J=7.4 & 1.5 Hz); 7.55-
7.36 (3H, m); 6.91-6.84 (2H, m); 6.18 (1H, br.s);
5.46 (2H, s); 4.15 (2H, t, J=7.2 Hz); 2.24 (3H,
s); 1.66 (2H, heptet, J=7.2 Hz); 1.40 (2H, sextet,
J=7.2 Hz); 0.94 (3H, t, J=7.2 Hz). Working Example 266 Butyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] carbamate (compound number
No. C1.28) Melting point: 127-128 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.2 Hz); 7.90 (1H, dd, J = 7.4 & 1.5 Hz); 7.55-
7.36 (3H, m); 6.91-6.84 (2H, m); 6.18 (1H, br.s);
5.46 (2H, s); 4.15 (2H, t, J = 7.2 Hz); 2.24 (3H,
s); 1.66 (2H, heptet, J = 7.2 Hz); 1.40 (2H, sextet,
J = 7.2 Hz); 0.94 (3H, t, J = 7.2 Hz).

【０５７０】[0570]

【実施例２６７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−３−エトキシプロピオンアミド
（化合物番号C1.44 ）融点：135 −137 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.19 (1H, b
r.s); 8.03 (1H, d, J=7.9 Hz); 7.89 (1H, d, J=7.4 H
z); 7.79 (1H, d, J=9.6 Hz); 7.35-7.54 (2H, m); 6.8
6-6.91 (2H, m); 5.46 (2H, s); 3.77 (2H, t, J=5.6 H
z); 3.60 (2H, q,J=7.0 Hz); 2.66 (2H, t, J=5.6 Hz);
2.24 (3H, s); 1.56 (3H, t, J=7.0 Hz).Working Example 267 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -3-ethoxypropionamide
(Compound No. C1.44) Melting point: 135-137 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.19 (1H, b
rs); 8.03 (1H, d, J = 7.9 Hz); 7.89 (1H, d, J = 7.4 H
z); 7.79 (1H, d, J = 9.6 Hz); 7.35-7.54 (2H, m); 6.8
6-6.91 (2H, m); 5.46 (2H, s); 3.77 (2H, t, J = 5.6 H
z); 3.60 (2H, q, J = 7.0 Hz); 2.66 (2H, t, J = 5.6 Hz);
2.24 (3H, s); 1.56 (3H, t, J = 7.0 Hz).

【０５７１】[0571]

【実施例２６８】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メトキシフェニル］カルバマート（化合物
番号C8.3）融点：112 −114 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-8.01
(1H, m); 7.92-7.88 (1H,m); 7.55-7.36 (3H, m); 7.01
(1H, br.s); 6.64-6.57 (2H, m); 5.46 (2H, s); 3.85
(3H, s); 3.76 (3H, s). Working Example 268 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methoxyphenyl] carbamate (compound
No. C8.3) Melting point: 112-114 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.06-8.01
(1H, m); 7.92-7.88 (1H, m); 7.55-7.36 (3H, m); 7.01
(1H, br.s); 6.64-6.57 (2H, m); 5.46 (2H, s); 3.85
(3H, s); 3.76 (3H, s).

【０５７２】[0572]

【実施例２６９】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メトキシフェニル］カルバマート（化合
物番号C8.6）融点：91−93℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.94-7.91
(1H, m); 7.79-7.74 (1H,m); 7.59-7.54 (1H, m); 7.42
-7.35 (2H, m); 7.00 (1H, br.s); 6.67-6.59 (2H, m);
5.03 (2H, s); 3.84 (3H, s); 3.76 (3H, s). Working Example 269 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -2-methoxyphenyl] carbamate (compound
Article No. C8.6) Melting point: 91-93 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.94-7.91
(1H, m); 7.79-7.74 (1H, m); 7.59-7.54 (1H, m); 7.42
-7.35 (2H, m); 7.00 (1H, br.s); 6.67-6.59 (2H, m);
5.03 (2H, s); 3.84 (3H, s); 3.76 (3H, s).

【０５７３】[0573]

【実施例２７０】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−３−メトキシフェニル］カルバマート（化合物
番号C8.20 ）融点：93−96℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
２（１Ｈ，ｄ，Ｊ＝７．２Ｈｚ）；７．８９
（１Ｈ，ｄｄ，Ｊ＝６．８＆１．０Ｈｚ）；
７．５３−７．３５（２Ｈ，ｍ）；７．２８
（１Ｈ，ｂｒ．ｓ）；６．９４（１Ｈ，ｄ，
Ｊ＝８．６Ｈｚ）；６．６５（１Ｈ，ｄｄ，
Ｊ＝８．６＆２．５Ｈｚ）；６．５３（１
Ｈ，ｂｒ．ｓ）；５．５０（２Ｈ，ｓ）；３．
９２（３Ｈ，ｓ）；３．７６（３Ｈ，ｓ）． Working Example 270 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -3-methoxyphenyl] carbamate (compound
No. C8.20) Melting point: 93-96 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
2. (1H, d, J = 7.2 Hz); 7.89
(1H, dd, J = 6.8 & 1.0 Hz);
7.53-7.35 (2H, m); 7.28
(1H, br.s); 6.94 (1H, d,
J = 8.6 Hz); 6.65 (1H, dd,
J = 8.6 & 2.5 Hz); 6.53 (1
H, br. 5.50 (2H, s);
92 (3H, s); 3.76 (3H, s).

【０５７４】[0574]

【実施例２７１】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−３−メトキシフェニル］カルバマート（化合
物番号Ｃ８．２３）融点：97−99℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.76-7.72
(2H, m); 7.58-7.54 (1H,m); 7.38-7.33 (2H, m); 6.99
(1H, d, J=8.7 Hz); 6.67 (1H, dd, J=8.7 & 1.9 Hz);
6.52 (1H, br.s); 5.33 (2H, s); 3.87 (3H, s); 3.76
(3H, s). Working Example 271 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -3-methoxyphenyl] carbamate (compound
Article No. C8.23) Melting point: 97-99 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.76-7.72
(2H, m); 7.58-7.54 (1H, m); 7.38-7.33 (2H, m); 6.99
(1H, d, J = 8.7 Hz); 6.67 (1H, dd, J = 8.7 & 1.9 Hz);
6.52 (1H, br.s); 5.33 (2H, s); 3.87 (3H, s); 3.76
(3H, s).

【０５７５】[0575]

【実施例２７２】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−フルオロフェニル］カルバマート（化合
物番号C9.6）融点：110 −115 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.00-7.89
(1H, m); 7.79-7.74 (1H,m); 7.59-7.54 (1H, m); 7.42
-7.36 (2H, m); 6.89-6.81 (2H, m); 6.63 (1H,br.s);
5.29 (2H, s); 3.78 (3H, s). Working Example 272 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -2-fluorophenyl] carbamate (compound
Article No. C9.6) Melting point: 110-115 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.00-7.89
(1H, m); 7.79-7.74 (1H, m); 7.59-7.54 (1H, m); 7.42
-7.36 (2H, m); 6.89-6.81 (2H, m); 6.63 (1H, br.s);
5.29 (2H, s); 3.78 (3H, s).

【０５７６】[0576]

【実施例２７３】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−３−フルオロフェニル］カルバマート（化合
物番号C9.24 ）融点：135 −138 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.78-7.73
(1H, m); 7.60-7.55 (1H,m); 7.41-7.32 (3H, m); 7.09
(1H, t, J=8.8 Hz); 6.96-6.90 (1H, m); 6.52(1H, b
r.s); 5.35 (2H, s); 3.77 (3H, s). Working Example 273 Methyl N- [4- (benzoxazol-2-ylmeth)
Toxi) -3-fluorophenyl] carbamate (compound
Product number C9.24) Melting point: 135-138 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.78-7.73
(1H, m); 7.60-7.55 (1H, m); 7.41-7.32 (3H, m); 7.09
(1H, t, J = 8.8 Hz); 6.96-6.90 (1H, m); 6.52 (1H, b
rs); 5.35 (2H, s); 3.77 (3H, s).

【０５７７】[0577]

【実施例２７４】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−３−クロロフェニル］カルバマート（化合物
番号C9.56 ）融点：164 −166 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.77-7.73
(1H, m); 7.59-7.50 (2H,m); 7.42-7.35 (2H, m); 7.19
(1H, dd, J=8.8 & 2.2 Hz); 7.06 (1H, d, J=8.8 Hz);
6.63 (1H, br.s); 5.35 (2H, s); 3.76 (3H, s). Working Example 274 Methyl N- [4- (benzoxazol-2-ylmethy)
Toxi) -3-chlorophenyl] carbamate (compound
No. C9.56) mp: 164 -166 ° C. NMR spectrum _{(200MHz, CDCl 3), δppm} : 7.77-7.73
(1H, m); 7.59-7.50 (2H, m); 7.42-7.35 (2H, m); 7.19
(1H, dd, J = 8.8 & 2.2 Hz); 7.06 (1H, d, J = 8.8 Hz);
6.63 (1H, br.s); 5.35 (2H, s); 3.76 (3H, s).

【０５７８】[0578]

【実施例２７５】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−トリフルオロメチルフェニル］カルバマ
ート（化合物番号C10.5 ）融点：69−71℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.93 (1H,
d, J=9.2 Hz); 7.79-7.75(1H, m); 7.60-7.53 (1H, m);
7.43-7.21 (4H, m); 6.71 (1H, br.s); 5.34 (2H, s);
3.78 (3H, s). Working Example 275 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -2-trifluoromethylphenyl] carbama
(Compound No. C10.5) Melting point: 69-71 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.93 (1H,
d, J = 9.2 Hz); 7.79-7.75 (1H, m); 7.60-7.53 (1H, m);
7.43-7.21 (4H, m); 6.71 (1H, br.s); 5.34 (2H, s);
3.78 (3H, s).

【０５７９】[0579]

【実施例２７６】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−３−トリフルオロメチルフェニル］カルバマー
ト（化合物番号C10.20）融点：142 −146 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.3 Hz); 7.91 (1H,dd, J=8.1 & 1.3 Hz); 7.73-
7.56 (3H, m); 7.65 (1H, d, J=1.3 Hz); 7.07 (1H, d,
J=8.8 Hz); 6.59 (1H, br.s); 5.55 (2H, s); 3.78 (3
H, s). Working Example 276 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -3-trifluoromethylphenyl] carbamer
(Compound number C10.20) melting point: 142-146 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.3 Hz); 7.91 (1H, dd, J = 8.1 & 1.3 Hz); 7.73-
7.56 (3H, m); 7.65 (1H, d, J = 1.3 Hz); 7.07 (1H, d,
J = 8.8 Hz); 6.59 (1H, br.s); 5.55 (2H, s); 3.78 (3
H, s).

【０５８０】[0580]

【実施例２７７】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−ニトロフェニル］カルバマート（化合物
番号C10.50）融点：130 −132 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：９．６
６（１Ｈ，ｂｒ．ｓ）；８．５１（１Ｈ，
ｄ，Ｊ＝９．４Ｈｚ）；７．８９（１Ｈ，
ｄ，Ｊ＝３．０Ｈｚ）；７．７９−７．７５
（１Ｈ，ｍ）；７．４４−７．３７（３Ｈ，
ｍ）；５．３７（２Ｈ，ｓ）；３．８２（３
Ｈ，ｓ）． Working Example 277 Methyl N- [4- (benzoxazol-2-ylmeth)
Toxi) -2-nitrophenyl] carbamate (compound
No. C10.50) Melting point: 130-132 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 9.6
8.5 (1H, br.s); 8.51 (1H, br.s)
d, J = 9.4 Hz); 7.89 (1H,
d, J = 3.0 Hz); 7.79-7.75
(1H, m); 7.44-7.37 (3H,
m); 5.37 (2H, s); 3.82 (3
H, s).

【０５８１】[0581]

【実施例２７８】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２，３，５−トリメチルフェニル］カルバマー
ト（化合物番号Ｃ１１．６４）融点：158 −160 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.94
(2H, m); 7.55-7.23 (3H,m); 6.26 (1H, br.s); 5.16
(2H, s); 3.78 (3H, s); 2.34 (3H, s); 2.29 (3H, s);
2.16 (3H, s). Working Example 278 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2,3,5-trimethylphenyl] carbamer
(Compound No. C11.64) Melting point: 158-160 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-7.94
(2H, m); 7.55-7.23 (3H, m); 6.26 (1H, br.s); 5.16
(2H, s); 3.78 (3H, s); 2.34 (3H, s); 2.29 (3H, s);
2.16 (3H, s).

【０５８２】[0582]

【実施例２７９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２，５−ジクロロフェニル］カルバマート（化
合物番号C14.18）融点：131 −133 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.28 (1H,
s); 8.04 (1H, d, J=7.9Hz); 7.92 (1H, dd, J=7.8 &
1.9 Hz); 7.53-7.39 (2H, m); 7.09 (1H, s); 6.86 (1
H, br.s); 5.50 (2H, s); 3.81 (3H, s). Working Example 279 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2,5-dichlorophenyl] carbamate
Compound No. C14.18) Melting point: 131-133 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.28 (1H,
s); 8.04 (1H, d, J = 7.9Hz); 7.92 (1H, dd, J = 7.8 &
1.9 Hz); 7.53-7.39 (2H, m); 7.09 (1H, s); 6.86 (1
H, br.s); 5.50 (2H, s); 3.81 (3H, s).

【０５８３】[0583]

【実施例２８０】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）フェニル］−Ｎ−メチルカルバマート（化合物
番号B1.5）融点：76−78℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.44
(1H, m); 7.59-7.55 (1H,m); 7.40-7.35 (2H, m); 7.19
-7.14 (2H, m); 7.08-7.02 (2H, m); 5.32 (2H,s); 3.6
8 (3H, s); 3.25 (3H, s). Working Example 280: Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) phenyl] -N-methylcarbamate (compound
No. B1.5) Melting point: 76-78 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.44
(1H, m); 7.59-7.55 (1H, m); 7.40-7.35 (2H, m); 7.19
-7.14 (2H, m); 7.08-7.02 (2H, m); 5.32 (2H, s); 3.6
8 (3H, s); 3.25 (3H, s).

【０５８４】[0584]

【実施例２８１】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）フェニル］−Ｎ−エチルカルバマート（化合物
番号B1.10 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H,m); 7.43-7.02 (4H, m); 5.32
(2H, s); 3.66 (3H, s); 3.65 (2H, q, J=7.1 Hz); 1.
12 (3H, t, J=7.1 Hz). Working Example 281 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) phenyl] -N-ethylcarbamate (compound
No. B1.10) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H, m); 7.43-7.02 (4H, m); 5.32
(2H, s); 3.66 (3H, s); 3.65 (2H, q, J = 7.1 Hz); 1.
12 (3H, t, J = 7.1 Hz).

【０５８５】[0585]

【実施例２８２】メチルＮ−アリル−Ｎ−［４−（ベンゾオキサゾール
−２−イルメトキシ）フェニル］カルバマート（化合物
番号B2.37 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H,m); 7.43-7.33 (2H, m); 7.18
-7.10 (2H, m); 7.06-7.00 (2H, m); 5.97-5.79(1H,
m); 5.31 (2H, s); 5.17-5.15 (1H, m); 5.11-5.07 (1
H, m); 4.22-4.18 (2H, m); 3.68 (3H, br.s).Working Example 282 Methyl N-allyl-N- [4- (benzoxazole
-2-ylmethoxy) phenyl] carbamate (compound
No. B2.37) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H, m); 7.43-7.33 (2H, m); 7.18
-7.10 (2H, m); 7.06-7.00 (2H, m); 5.97-5.79 (1H,
m); 5.31 (2H, s); 5.17-5.15 (1H, m); 5.11-5.07 (1
H, m); 4.22-4.18 (2H, m); 3.68 (3H, br.s).

【０５８６】[0586]

【実施例２８３】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−メチルカルバマー
ト（化合物番号D1.2）融点：88−91℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.3 Hz); 7.91 (1H,d, J=7.3 Hz); 7.55-7.41 (2
H, m); 7.05 (2H, d, J=8.3 Hz); 6.93-6.83 (2H,m);
5.46 (2H, s); 3.63 (3H, s); 3.16 (3H, s); 2.18 (3
H, s). Working Example 283 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-methylcarbamer
(Compound No. D1.2) Melting point: 88-91 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.3 Hz); 7.91 (1H, d, J = 7.3 Hz); 7.55-7.41 (2
H, m); 7.05 (2H, d, J = 8.3 Hz); 6.93-6.83 (2H, m);
5.46 (2H, s); 3.63 (3H, s); 3.16 (3H, s); 2.18 (3
H, s).

【０５８７】[0587]

【実施例２８４】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−メチルカルバマ
ート（化合物番号D1.4）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．７
９−７．７５（１Ｈ，ｍ）；７．５９−７．５５
（１Ｈ，ｍ）；７．４３−７．３６（２Ｈ，
ｍ）；７．０７−７．０２（１Ｈ，ｍ）；６．
９４−６．８６（２Ｈ，ｍ）；５．３１（２
Ｈ，ｓ）；３．６３（３Ｈ，ｓ）；３．１６
（３Ｈ，ｓ）；２．１７（３Ｈ，ｓ）． Working Example 284 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -2-methylphenyl] -N-methylcarbama
(Compound No. D1.4) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.7
9-7.75 (1H, m); 7.59-7.55
(1H, m); 7.43-7.36 (2H,
7.07-7.02 (1H, m);
94-6.86 (2H, m); 5.31 (2
H, s); 3.63 (3H, s); 3.16
(3H, s); 2.17 (3H, s).

【０５８８】[0588]

【実施例２８５】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−エチルカルバマ
ート（化合物番号Ｄ１．８）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.59-7.55 (1H,m); 7.43-7.36 (2H, m); 7.04
-6.86 (3H, m); 5.31 (2H, s); 3.78-3.37 (2H,br.m);
3.62 (3H, s); 2.17 (3H, s); 1.12 (3H, t, J=7.4 H
z). Working Example 285 Methyl N- [4- (benzoxazol-2-ylmeth)
Toxi) -2-methylphenyl] -N-ethylcarbama
(Compound No. D1.8) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.59-7.55 (1H, m); 7.43-7.36 (2H, m); 7.04
-6.86 (3H, m); 5.31 (2H, s); 3.78-3.37 (2H, br.m);
3.62 (3H, s); 2.17 (3H, s); 1.12 (3H, t, J = 7.4 H
z).

【０５８９】[0589]

【実施例２８６】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−イソプロピルカル
バマート（化合物番号D1.10 ）融点：98−100 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.89
(2H, m); 7.52-7.41 (2H,m); 7.00 (1H, d, J=8.8 Hz);
6.94 (1H, d, J=3.0 Hz); 6.87-6.82 (1H, m);5.47 (2
H, s); 4.48 (1H, br.s); 3.62 (3H, br.s); 2.17 (3H,
s); 1.27 (3H,d, J=6.8 Hz); 0.94 (3H, d, J=6.8 H
z). Working Example 286 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-isopropylcarb
Bamate (Compound No. D1.10) Melting point: 98-100 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.89
(2H, m); 7.52-7.41 (2H, m); 7.00 (1H, d, J = 8.8 Hz);
6.94 (1H, d, J = 3.0 Hz); 6.87-6.82 (1H, m); 5.47 (2
H, s); 4.48 (1H, br.s); 3.62 (3H, br.s); 2.17 (3H,
s); 1.27 (3H, d, J = 6.8 Hz); 0.94 (3H, d, J = 6.8 H
z).

【０５９０】[0590]

【実施例２８７】メチルＮ−アリル−Ｎ−［４−（ベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト（化合物番号D1.14 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
２（１Ｈ，ｄｄ，Ｊ＝８．０＆１．５Ｈ
ｚ）；７．８９（１Ｈ，ｄｄ，Ｊ＝８．０＆
１．５Ｈｚ）；７．４９（１Ｈ，ｔｄ，Ｊ
＝８．０＆１．５Ｈｚ）；７．３９（１Ｈ，
ｔｄ，Ｊ＝８．０＆１．５Ｈｚ）；７．０
１（１Ｈ，ｄ，Ｊ＝８．４Ｈｚ）；６．９１
（１Ｈ，ｄ，Ｊ＝２．６Ｈｚ）；６，８３
（１Ｈ，ｄｄ，Ｊ＝８．４＆２．６Ｈｚ）；
５．９８−５．７９（１Ｈ，ｍ）；５．４４
（２Ｈ，ｓ）；５．１２−５．０４（２Ｈ，
ｍ）；４．４０−４．２６（１Ｈ，ｍ）；３．
９５−３．８０（１Ｈ，ｍ）；３．７８−３．６
３（３Ｈ，ｍ）；２．１７（３Ｈ，ｓ）．Working Example 287 Methyl N-allyl-N- [4- (benzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamer
(Compound No. D1.14) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
2 (1H, dd, J = 8.0 & 1.5 H
7.89 (1H, dd, J = 8.0 &
7.49 (1H, td, J)
= 8.0 & 1.5 Hz); 7.39 (1H,
td, J = 8.0 & 1.5 Hz); 7.0
1 (1H, d, J = 8.4 Hz); 6.91
(1H, d, J = 2.6 Hz); 6, 83
(1H, dd, J = 8.4 & 2.6 Hz);
5.98-5.79 (1H, m); 5.44
(2H, s); 5.12-5.04 (2H, s);
m); 4.40-4.26 (1H, m);
95-3.80 (1H, m); 3.78-3.6
3 (3H, m); 2.17 (3H, s).

【０５９１】[0591]

【実施例２８８】メチルＮ−アリル−Ｎ−［４−（ベンゾオキサゾール
−２−イルメトキシ）−２−メチルフェニル］カルバマ
ート（化合物番号Ｄ１．１６）油状物ＮＭＲスペクトル(200Mz,CDCl₃),δppm: 7.80-7.73 (1
H, m); 7.60-7.53 (1H, m); 7.43-7.33 (2H, m); 7.02
(1H, d, J=8.7 Hz); 6.94 (1H, d, J=2.9 Hz); 6.86 (1
H, dd, J=8.7 & 2.9 Hz); 6.00-5.80 (1H, m); 5.30 (2
H, s); 5.13-5.04(2H, m); 4.41-4.28 (1H, m); 3.94-
3.83 (1H, m); 3.78-3.64 (3H, m); 2.17 (3H, s).Working Example 288 Methyl N-allyl-N- [4- (benzoxazole
-2-ylmethoxy) -2-methylphenyl] carbama
(Compound No. D1.16) Oil NMR spectrum (200 Mz, CDCl ₃ ), δ ppm: 7.80-7.73 (1
H, m); 7.60-7.53 (1H, m); 7.43-7.33 (2H, m); 7.02
(1H, d, J = 8.7 Hz); 6.94 (1H, d, J = 2.9 Hz); 6.86 (1
H, dd, J = 8.7 & 2.9 Hz); 6.00-5.80 (1H, m); 5.30 (2
H, s); 5.13-5.04 (2H, m); 4.41-4.28 (1H, m); 3.94-
3.83 (1H, m); 3.78-3.64 (3H, m); 2.17 (3H, s).

【０５９２】[0592]

【実施例２８９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−プロピニ
ル）カルバマート（化合物番号D1.18 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.2 Hz); 7.92 (1H,d, J=7.1 Hz); 7.57-7.35 (2
H, m); 7.19 (1H, d, J=8.5 Hz); 6.96-6.83 (2H,m);
5.47 (2H, s); 4.57-4.10 (2H, m); 3.82-3.66 (3H,
m); 2.22 (4H, br.s). Working Example 289 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-propini
B) Carbamate (Compound No. D1.18) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.2 Hz); 7.92 (1H, d, J = 7.1 Hz); 7.57-7.35 (2
H, m); 7.19 (1H, d, J = 8.5 Hz); 6.96-6.83 (2H, m);
5.47 (2H, s); 4.57-4.10 (2H, m); 3.82-3.66 (3H,
m); 2.22 (4H, br.s).

【０５９３】[0593]

【実施例２９０】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（４−クロロフェ
ナシル）カルバマート（化合物番号D1.40 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (2H,
d, J=7.4 Hz); 7.88 (3H,d, J=8.6Hz); 7.54-7.34 (4H,
m); 6.92-6.81 (2H, m); 5.45 (2H, s); 4.88 (2H, AB
q, J=16.9Hz, Dn=183.3）；３．６９（３Ｈ，
ｓ）；２．２８（３Ｈ，ｓ）． Working Example 290 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (4-chlorophene
Nasyl) carbamate (Compound No. D1.40) oil NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.03 (2H,
d, J = 7.4 Hz); 7.88 (3H, d, J = 8.6Hz); 7.54-7.34 (4H,
m); 6.92-6.81 (2H, m); 5.45 (2H, s); 4.88 (2H, AB
q, J = 16.9Hz, Dn = 183.3); 3.69 (3H,
s); 2.28 (3H, s).

【０５９４】[0594]

【実施例２９１】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−エトキシカルボニ
ルメチルカルバマート（化合物番号Ｄ１．４３）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=8.0 Hz); 7.91 (1H,d, J=8.1 Hz); 7.55-7.31 (3
H, m); 6.92-6.82 (2H, m); 5.46 (2H, s); 4.59(1H,
d, J=17.4 Hz); 4.21 (2H, q, J=7.2 Hz); 3.77 (1H,
s); 3.76 (3H, s);2.22 (3H, s); 1.27 (3H, t, J=7.2
Hz). Working Example 291 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-ethoxycarboni
Lemethylcarbamate (Compound No. D1.43) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 8.0 Hz); 7.91 (1H, d, J = 8.1 Hz); 7.55-7.31 (3
H, m); 6.92-6.82 (2H, m); 5.46 (2H, s); 4.59 (1H,
d, J = 17.4 Hz); 4.21 (2H, q, J = 7.2 Hz); 3.77 (1H,
s); 3.76 (3H, s); 2.22 (3H, s); 1.27 (3H, t, J = 7.2
Hz).

【０５９５】[0595]

【実施例２９２】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−メチルチオメチル
カルバマート（化合物番号D1.62 ）融点：87−88℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.89
(2H, m); 7.56-7.38 (2H,m); 7.19-7.15 (1H, m); 6.95
-6.86 (2H, m); 5.48 (2H, s); 4.73 (2H, AB q,J=13.8
Hz, Dn=111.3 ）; 3.88 (3H, s); 3.81-3.61 (3H, m);
2.23 (3H, s); 2.20 (3H, s). Working Example 292 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-methylthiomethyl
Carbamate (Compound No. D1.62) Melting point: 87-88 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.89
(2H, m); 7.56-7.38 (2H, m); 7.19-7.15 (1H, m); 6.95
-6.86 (2H, m); 5.48 (2H, s); 4.73 (2H, AB q, J = 13.8
Hz, Dn = 111.3); 3.88 (3H, s); 3.81-3.61 (3H, m);
2.23 (3H, s); 2.20 (3H, s).

【０５９６】[0596]

【実施例２９３】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−ベンジルオキシメ
チルカルバマート（化合物番号D1.67 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
５（１Ｈ，ｄｄ，Ｊ＝８．０＆０．７Ｈ
ｚ）；７．９１（１Ｈ，ｄｄ，Ｊ＝７．６＆
１．７Ｈｚ）；７．５２（１Ｈ，ｔｄ，Ｊ
＝７．６＆１．４Ｈｚ）；７．４１（１Ｈ，
ｔｄ，Ｊ＝７．５＆１．３Ｈｚ）；７．３
３（５Ｈ，ｍ）；７．１２（１Ｈ，ｄ，Ｊ
＝８．６Ｈｚ）；６．９５−６．８４（２Ｈ，
ｍ）；５．４８（２Ｈ，ｓ）；５．３１（１
Ｈ，ｄ，Ｊ＝１０．０Ｈｚ）；４．７９（１
Ｈ，ｄ，Ｊ＝１０．３Ｈｚ）；４．６９（２
Ｈ，ｂｒ．ｓ）；３．７０（３Ｈ，ｓ）；
２．２１（３Ｈ，ｓ）． Working Example 293 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-benzyloxime
Tilcarbamate (Compound No. D1.67) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
5 (1H, dd, J = 8.0 & 0.7H
z); 7.91 (1H, dd, J = 7.6 &
7.52 (1H, td, J)
= 7.6 & 1.4 Hz); 7.41 (1H,
td, J = 7.5 & 1.3 Hz); 7.3
3 (5H, m); 7.12 (1H, d, J
= 8.6 Hz); 6.95-6.84 (2H,
m); 5.48 (2H, s); 5.31 (1
H, d, J = 10.0 Hz); 4.79 (1
H, d, J = 10.3 Hz); 4.69 (2
H, br. s); 3.70 (3H, s);
2.21 (3H, s).

【０５９７】[0597]

【実施例２９４】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−エトキシエ
チル）カルバマート（化合物番号Ｄ１．１１０）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.9 Hz); 7.91 (1H,dd, J=6.9 & 1.0 Hz); 7.51
(1H, td, J=7.6 & 1.4 Hz); 7.10 (1H, d, J=8.6Hz);
6.92-6.83 (2H, m); 5.47 (2H, s); 4.00-3.70 (2H,
m); 3.63 (3H, s); 3.60-3.48 (2H, m); 3.44 (2H, q,
J=7.0 Hz); 2.18 (3H, s); 1.14 (3H, t, J=7.0 Hz). Working Example 294 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-ethoxy
Tyl) carbamate (Compound No. D1.110) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.9 Hz); 7.91 (1H, dd, J = 6.9 & 1.0 Hz); 7.51
(1H, td, J = 7.6 & 1.4 Hz); 7.10 (1H, d, J = 8.6Hz);
6.92-6.83 (2H, m); 5.47 (2H, s); 4.00-3.70 (2H,
m); 3.63 (3H, s); 3.60-3.48 (2H, m); 3.44 (2H, q,
J = 7.0 Hz); 2.18 (3H, s); 1.14 (3H, t, J = 7.0 Hz).

【０５９８】[0598]

【実施例２９５】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−ビニルオキ
シエチル）カルバマート（化合物番号D1.112）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.88
(2H, m); 7.57-7.35 (2H,m); 7.07 (1H, d, J=8.1 Hz);
6.95-6.82 (2H, m); 6.50-6.37 (1H, m); 5.47(2H,
s); 4.20-3.92 (2H, m); 3.85-3.56 (4H, m); 3.64 (3
H, br.s); 2.17 (3H, s). Working Example 295 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-vinyloxy
Siethyl) carbamate (Compound No. D1.112) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-7.88
(2H, m); 7.57-7.35 (2H, m); 7.07 (1H, d, J = 8.1 Hz);
6.95-6.82 (2H, m); 6.50-6.37 (1H, m); 5.47 (2H, m
s); 4.20-3.92 (2H, m); 3.85-3.56 (4H, m); 3.64 (3
H, br.s); 2.17 (3H, s).

【０５９９】[0599]

【実施例２９６】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−プロポキシ
エチル）カルバマート（化合物番号D1.113）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
４（１Ｈ，ｄ，Ｊ＝７．７Ｈｚ）；７．９１
（１Ｈ，ｄ，Ｊ＝８．１Ｈｚ）；７．５５−
７．３７（１Ｈ，ｍ）；７．１０（１Ｈ，
ｄ，Ｊ＝８．４Ｈｚ）；６．８８−６．８２
（２Ｈ，ｍ）；５．４６（２Ｈ，ｓ）；３．９
３−３．７５（２Ｈ，ｍ）；３．６３−３．４９
（５Ｈ，ｍ）；３．３４（２Ｈ，ｔ，Ｊ＝
６．７Ｈｚ）；２．１８（３Ｈ，ｓ）；１．
７１−１．４８（２Ｈ，ｍ）；０．８７（３
Ｈ，ｔ，Ｊ＝７．５Ｈｚ）． Working Example 296 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-propoxy
Ethyl) carbamate (Compound No. D1.113) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
4. (1H, d, J = 7.7 Hz); 7.91
(1H, d, J = 8.1 Hz); 7.55-
7.37 (1H, m); 7.10 (1H,
d, J = 8.4 Hz); 6.88-6.82
(2H, m); 5.46 (2H, s); 3.9
3-3.75 (2H, m); 3.63-3.49
(5H, m); 3.34 (2H, t, J =
6.7 Hz); 2.18 (3H, s);
71-1.48 (2H, m); 0.87 (3
H, t, J = 7.5 Hz).

【０６００】[0600]

【実施例２９７】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−メチルチオ
エチル）カルバマート（化合物番号Ｄ１．１１４）融点：119 −120 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=8.8 Hz); 7.92 (1H,d, J=7.6 Hz); 7.57-7.35 (2
H, m); 7.07 (1H, d, J=8.7 Hz); 6.96-6.82 (2H,m);
5.47 (2H, s); 4.02-3.40 (2H, m); 3.63 (3H, s); 2.6
5 (2H, t, J=7.7 Hz); 2.17 (3H, s); 2.13 (3H, s). Working Example 297 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-methylthio
Ethyl) carbamate (Compound No. D1.114) Melting point: 119-120 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 8.8 Hz); 7.92 (1H, d, J = 7.6 Hz); 7.57-7.35 (2
H, m); 7.07 (1H, d, J = 8.7 Hz); 6.96-6.82 (2H, m);
5.47 (2H, s); 4.02-3.40 (2H, m); 3.63 (3H, s); 2.6
5 (2H, t, J = 7.7 Hz); 2.17 (3H, s); 2.13 (3H, s).

【０６０１】[0601]

【実施例２９８】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−エチルチオ
エチル）カルバマート（化合物番号D1.116）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.4 Hz); 7.92 (1H,d, J=7.6 Hz); 7.56-7.37 (2
H, m); 7.07 (1H, br.d, J=8.8 Hz); 6.95-6.82 (2H,
m); 5.47 (2H, s); 4.03-3.38 (2H, m); 3.63 (3H, s);
2.80-2.45 (4H, m); 2.19 (1H, s); 1.32-1.18 (3H,
m). Working Example 298: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-ethylthio
Ethyl) carbamate (Compound No. D1.116) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.4 Hz); 7.92 (1H, d, J = 7.6 Hz); 7.56-7.37 (2
H, m); 7.07 (1H, br.d, J = 8.8 Hz); 6.95-6.82 (2H,
m); 5.47 (2H, s); 4.03-3.38 (2H, m); 3.63 (3H, s);
2.80-2.45 (4H, m); 2.19 (1H, s); 1.32-1.18 (3H,
m).

【０６０２】[0602]

【実施例２９９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−［２−（テトラヒ
ドロピラン−２−イルオキシ）エチル］カルバマート
（化合物番号D1.119）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
４（１Ｈ，ｄ，Ｊ＝７．９Ｈｚ）；７．９１
（１Ｈ，ｄ，Ｊ＝７．３Ｈｚ）；７．５５−
７．３７（２Ｈ，ｍ）；７．１９−６．８０
（３Ｈ，ｍ）；５．４７（２Ｈ，ｓ）；４．
５５（１Ｈ，ｂｒ．ｓ）；４．１０−３．３９
（６Ｈ，ｍ）；３．６３（３Ｈ，ｓ）；２．
１８（３Ｈ，ｓ）；１．９０−１．３５（６
Ｈ，ｍ）． Working Example 299 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- [2- (tetrahi
Dropyran-2-yloxy) ethyl] carbamate
(Compound No. D1.119) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
4. (1H, d, J = 7.9 Hz); 7.91
(1H, d, J = 7.3 Hz); 7.55-
7.37 (2H, m); 7.19-6.80
(3H, m); 5.47 (2H, s);
55 (1H, br.s); 4.10-3.39
(6H, m); 3.63 (3H, s);
18 (3H, s); 1.90-1.35 (6
H, m).

【０６０３】[0603]

【実施例３００】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニルプロピ
オンアミド（化合物番号Ｄ２．４）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.89
(2H, m); 7.56-7.38 (2H,m); 6.99-6.91 (3H, m); 5.48
(2H, s); 3.71 (3H, s); 3.02-2.91 (2H, m); 2.09 (3
H, s); 1.19 (3H, t, J=7.2 Hz). Working Example 300 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylpropyl
Onamide (Compound No. D2.4) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-7.89
(2H, m); 7.56-7.38 (2H, m); 6.99-6.91 (3H, m); 5.48
(2H, s); 3.71 (3H, s); 3.02-2.91 (2H, m); 2.09 (3
H, s); 1.19 (3H, t, J = 7.2 Hz).

【０６０４】[0604]

【実施例３０１】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−メチルフェニル］−Ｎ−メトキシカルボニルプロ
ピオンアミド（化合物番号D2.5）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H,m); 7.40-7.36 (2H, m); 6.97
-6.93 (3H, m); 5.32 (2H, s); 3.71 (3H, s); 2.96 (2
H, qd, J=7.4 & 2.9 Hz); 2.08 (3H, s); 1.18 (3H, t,
J=7.4 Hz). Working Example 301 N- [4- (benzoxazol-2-ylmethoxy)
-2-methylphenyl] -N-methoxycarbonylpro
Pionamide (Compound No. D2.5) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H, m); 7.40-7.36 (2H, m); 6.97
-6.93 (3H, m); 5.32 (2H, s); 3.71 (3H, s); 2.96 (2
H, qd, J = 7.4 & 2.9 Hz); 2.08 (3H, s); 1.18 (3H, t,
J = 7.4 Hz).

【０６０５】[0605]

【実施例３０２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニルブチル
アミド（化合物番号D2.7）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.89
(2H, m); 7.56-7.41 (2H,m); 6.98-6.91 (3H, m); 5.48
(2H, s); 3.71 (3H, s); 2.97-2.89 (2H, m); 2.09 (3
H, s); 1.71 (2H, q, J=7.6 Hz); 0.99 (3H, t, J=7.2
Hz). Working Example 302 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylbutyl
Amide (Compound No. D2.7) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.89
(2H, m); 7.56-7.41 (2H, m); 6.98-6.91 (3H, m); 5.48
(2H, s); 3.71 (3H, s); 2.97-2.89 (2H, m); 2.09 (3
H, s); 1.71 (2H, q, J = 7.6 Hz); 0.99 (3H, t, J = 7.2
Hz).

【０６０６】[0606]

【実施例３０３】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−メチルフェニル］−Ｎ−メトキシカルボニルブチ
ルアミド（化合物番号D2.9）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H,m); 7.43-7.36 (2H, m); 6.99
-6.94 (3H, m); 5.32 (2H, s); 3.71 (3H, s); 2.93 (2
H, td, J=7.3 & 2.0 Hz); 2.09 (3H, s); 1.80-1.62 (2
H, m); 0.98 (3H,t, J=7.3 Hz). Working Example 303 N- [4- (Benzoxazol-2-ylmethoxy)
-2-methylphenyl] -N-methoxycarbonylbuty
Luamide (Compound No. D2.9) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H, m); 7.43-7.36 (2H, m); 6.99
-6.94 (3H, m); 5.32 (2H, s); 3.71 (3H, s); 2.93 (2
H, td, J = 7.3 & 2.0 Hz); 2.09 (3H, s); 1.80-1.62 (2
H, m); 0.98 (3H, t, J = 7.3 Hz).

【０６０７】[0607]

【実施例３０４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２−
メチルプロピオンアミド（化合物番号D2.10 ）融点：90−92℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.89
(2H, m); 7.56-7.38 (2H,m); 6.98-6.90 (3H, m); 5.48
(2H, s); 3.71 (3H, s); 2.09 (3H, s); 1.25 (3H, d,
J=2.0 Hz). Working Example 304 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2-
Methylpropionamide (Compound No. D2.10) Melting point: 90-92 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-7.89
(2H, m); 7.56-7.38 (2H, m); 6.98-6.90 (3H, m); 5.48
(2H, s); 3.71 (3H, s); 2.09 (3H, s); 1.25 (3H, d,
J = 2.0 Hz).

【０６０８】[0608]

【実施例３０５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニルペンタ
ンアミド（化合物番号D2.11 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.88
(2H, m); 7.56-7.36 (2H,m); 6.99-6.87 (3H, m); 5.45
(2H, s); 3.71 (3H, s); 2.95 (2H, td, J=7.4& 2.3 H
z); 2.09 (3H, s); 1.75-1.25 (4H, m); 0.93 (3H, t,
J=7.3 Hz). Working Example 305 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylpentane
Amide (compound number D2.11) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-7.88
(2H, m); 7.56-7.36 (2H, m); 6.99-6.87 (3H, m); 5.45
(2H, s); 3.71 (3H, s); 2.95 (2H, td, J = 7.4 & 2.3 H
z); 2.09 (3H, s); 1.75-1.25 (4H, m); 0.93 (3H, t,
J = 7.3 Hz).

【０６０９】[0609]

【実施例３０６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−３−
メチルブチルアミド（化合物番号D2.13 ）融点：78−80℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
６−７．９０（２Ｈ，ｍ）；７．５６−７．３８
（２Ｈ，ｍ）；６．９８−６．９１（３Ｈ，
ｍ）；５．４８（２Ｈ，ｓ）；３．７１（３
Ｈ，ｓ）；２．８４（２Ｈ，ｄ，Ｊ＝６．８
Ｈｚ）；２．３０−２．１５（１Ｈ，ｍ）；
２．１０（３Ｈ，ｓ）；０．９９（６Ｈ，
ｄ，Ｊ＝６．６Ｈｚ）． Working Example 306 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-3-
Methylbutyramide (Compound No. D2.13) Melting point: 78-80 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
6-7.90 (2H, m); 7.56-7.38.
(2H, m); 6.98-6.91 (3H,
m); 5.48 (2H, s); 3.71 (3
H, s); 2.84 (2H, d, J = 6.8)
Hz); 2.30-2.15 (1H, m);
2.10 (3H, s); 0.99 (6H, s)
d, J = 6.6 Hz).

【０６１０】[0610]

【実施例３０７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニルシクロ
ブタンカルボキサミド（化合物番号Ｄ２．１４）融点：76−78℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.89
(2H, m); 7.55-7.38 (2H,m); 6.98-6.91 (3H, m); 5.48
(2H, s); 4.10-3.91 (1H, m); 3.70 (3H, s); 2.46-2.
20 (4H, m); 2.08-1.80 (2H, m). Working Example 307 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylcyclo
Butanecarboxamide (Compound No. D2.14) Melting point: 76-78 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-7.89
(2H, m); 7.55-7.38 (2H, m); 6.98-6.91 (3H, m); 5.48
(2H, s); 4.10-3.91 (1H, m); 3.70 (3H, s); 2.46-2.
20 (4H, m); 2.08-1.80 (2H, m).

【０６１１】[0611]

【実施例３０８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニルシクロ
ペンタンカルボキサミド（化合物番号D2.15 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.89
(2H, m); 7.55-7.37 (2H,m); 6.98-6.90 (3H, m); 5.48
(2H, s); 3.85-3.68 (1H, m); 3.71 (3H, s); 2.10 (3
H, s); 1.97-1.53 (8H, m). Working Example 308 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylcyclo
Pentanecarboxamide (Compound No. D2.15) oil NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.06-7.89
(2H, m); 7.55-7.37 (2H, m); 6.98-6.90 (3H, m); 5.48
(2H, s); 3.85-3.68 (1H, m); 3.71 (3H, s); 2.10 (3
H, s); 1.97-1.53 (8H, m).

【０６１２】[0612]

【実施例３０９】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニルシクロ
ヘキサンカルボキサミド（化合物番号D2.17 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=8.1 Hz); 7.91 (1H,d, J=8.4 Hz); 7.55-7.37 (2
H, m); 6.96-6.89 (3H, m); 5.48 (2H, s); 3.71(3H,
s); 3.49-3.47 (1H, m); 2.08 (3H, s); 2.04-1.23 (10
H, m). Working Example 309 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylcyclo
Hexanecarboxamide (Compound No.D2.17) oil NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.04 (1H,
d, J = 8.1 Hz); 7.91 (1H, d, J = 8.4 Hz); 7.55-7.37 (2
H, m); 6.96-6.89 (3H, m); 5.48 (2H, s); 3.71 (3H,
s); 3.49-3.47 (1H, m); 2.08 (3H, s); 2.04-1.23 (10
H, m).

【０６１３】[0613]

【実施例３１０】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２−
メトキシアセトアミド（化合物番号D2.26 ）融点：70−73℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.90
(2H, m); 7.56-7.38 (2H,m); 7.08-6.89 (3H, m); 5.48
(2H, s); 3.72 (3H, s); 3.49 (2H, s); 2.10 (3H,
s). Working Example 310 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2-
Methoxyacetamide (Compound No. D2.26) Melting point: 70-73 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.90
(2H, m); 7.56-7.38 (2H, m); 7.08-6.89 (3H, m); 5.48
(2H, s); 3.72 (3H, s); 3.49 (2H, s); 2.10 (3H, s);
s).

【０６１４】[0614]

【実施例３１１】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−メチルフェニル］−Ｎ−メトキシカルボニル−２
−メトキシアセトアミド（化合物番号D2.28 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.80-7.75
(1H, m); 7.61-7.56 (1H,m); 7.41-7.36 (2H, m); 6.98
-6.94 (3H, m); 5.33 (2H, s); 4.71 (2H, s); 3.72 (3
H, s); 3.48 (3H, s); 2.09 (3H, s). Working Example 311 N- [4- (benzoxazol-2-ylmethoxy)
-2-methylphenyl] -N-methoxycarbonyl-2
-Methoxyacetamide (Compound No. D2.28) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.80-7.75
(1H, m); 7.61-7.56 (1H, m); 7.41-7.36 (2H, m); 6.98
-6.94 (3H, m); 5.33 (2H, s); 4.71 (2H, s); 3.72 (3
H, s); 3.48 (3H, s); 2.09 (3H, s).

【０６１５】[0615]

【実施例３１２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニルベンズ
アミド（化合物番号D2.42 ）融点：112 −114 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.90
(2H, m); 7.72-7.40 (2H,m); 7.12 (1H, d, J=8.6 Hz);
7.00-6.92 (2H, m); 5.49 (2H, s); 3.66 (3H,s); 2.2
7 (3H, s). Working Example 312 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylbenz
Amide (Compound No. D2.42) Melting point: 112-114 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.90
(2H, m); 7.72-7.40 (2H, m); 7.12 (1H, d, J = 8.6 Hz);
7.00-6.92 (2H, m); 5.49 (2H, s); 3.66 (3H, s); 2.2
7 (3H, s).

【０６１６】[0616]

【実施例３１３】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−メチルフェニル］−Ｎ−メトキシカルボニルベン
ズアミド（化合物番号D2.44 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
９−７．６７（３Ｈ，ｍ）；７．６０−７．３６
（６Ｈ，ｍ）；７．１２（１Ｈ，ｄ，Ｊ＝
８．３Ｈｚ）；６．９９−６．９２（２Ｈ，
ｓ）；５．３３（２Ｈ，ｓ）；３．６５（３
Ｈ，ｓ）；２．２７（３Ｈ，ｓ）．Example 313 N- [4- (benzoxazol-2-ylmethoxy)
-2-methylphenyl] -N-methoxycarbonylben
Dzamide (Compound No. D2.44) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
9-7.67 (3H, m); 7.60-7.36
(6H, m); 7.12 (1H, d, J =
8.3 Hz); 6.99-6.92 (2H,
5.33 (2H, s); 3.65 (3
H, s); 2.27 (3H, s).

【０６１７】[0617]

【実施例３１４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２，
４−ジフルオロベンズアミド（化合物番号Ｄ２．５２）融点：137 −139 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.90
(2H, m); 7.70-7.38 (3H,m); 7.11 (1H, d, J=8.4 Hz);
7.03-6.80 (4H, m); 5.50 (2H, s); 3.69 (3H,s); 2.2
3 (3H, s). Working Example 314 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2,
4-Difluorobenzamide (Compound No. D2.52) Melting point: 137-139 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.90
(2H, m); 7.70-7.38 (3H, m); 7.11 (1H, d, J = 8.4 Hz);
7.03-6.80 (4H, m); 5.50 (2H, s); 3.69 (3H, s); 2.2
3 (3H, s).

【０６１８】[0618]

【実施例３１５】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−２−
メトキシベンズアミド（化合物番号D2.54 ）融点：126 −128 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.90
(2H, m); 7.55-7.39 (3H,m); 7.16-6.89 (5H, m); 5.50
(2H, s); 3.88 (3H, s); 3.61 (3H, s); 2.27 (3H,
s).Example 315 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-2-
Methoxybenzamide (Compound No. D2.54) Melting point: 126-128 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.90
(2H, m); 7.55-7.39 (3H, m); 7.16-6.89 (5H, m); 5.50
(2H, s); 3.88 (3H, s); 3.61 (3H, s); 2.27 (3H, s)
s).

【０６１９】[0619]

【実施例３１６】Ｎ−［４−（ベンゾオキサゾール−２−イルメトキシ）
−２−メチルフェニル］−Ｎ−メトキシカルボニル−２
−メトキシベンズアミド（化合物番号D2.55 ）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.80-7.75
(1H, m); 7.58-7.36 (5H,m); 7.15-6.89 (5H, m); 5.34
(2H, s); 3.87 (3H, s); 3.60 (3H, s); 2.26 (3H,
s); 3.66 (2H, s); 2.41 (3H, s); 2.26 (3H, s).Example 316 N- [4- (benzoxazol-2-ylmethoxy)
-2-methylphenyl] -N-methoxycarbonyl-2
-Methoxybenzamide (Compound No. D2.55) amorphous NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.80-7.75
(1H, m); 7.58-7.36 (5H, m); 7.15-6.89 (5H, m); 5.34
(2H, s); 3.87 (3H, s); 3.60 (3H, s); 2.26 (3H,
s); 3.66 (2H, s); 2.41 (3H, s); 2.26 (3H, s).

【０６２０】[0620]

【実施例３１７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−４−
メチルベンズアミド（化合物番号D2.61 ）融点：132 −133 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.89
(2H, m); 7.61 (2H, dd,J=6.5 & 1.8 Hz); 7.55-7.41
(2H, m); 7.27-7.21 (2H, m); 7.11 (1H, d, J=8.5 H
z); 6.98-6.90 (2H, m); 5.48 (2H, s).Example 317 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-4-
Methylbenzamide (Compound No. D2.61) Melting point: 132-133 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-7.89
(2H, m); 7.61 (2H, dd, J = 6.5 & 1.8 Hz); 7.55-7.41
(2H, m); 7.27-7.21 (2H, m); 7.11 (1H, d, J = 8.5 H
z); 6.98-6.90 (2H, m); 5.48 (2H, s).

【０６２１】[0621]

【実施例３１８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−メトキシカルボニル−３−
クロロベンゾチオフェン−２−カルボキサミド（化合物
番号D2.72 ）融点：155 −157 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.3 Hz); 7.94-7.80(3H, m); 7.55-7.37 (4H, m);
7.22 (1H, d, J=8.5 Hz); 7.01-6.91 (2H, m);5.49 (2
H, s); 3.72 (3H, s); 2.30 (3H, s). Working Example 318 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonyl-3-
Chlorobenzothiophene-2-carboxamide (compound
No. D2.72) melting point: 155-157 ° C NMR spectrum (200MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.3 Hz); 7.94-7.80 (3H, m); 7.55-7.37 (4H, m);
7.22 (1H, d, J = 8.5 Hz); 7.01-6.91 (2H, m); 5.49 (2
H, s); 3.72 (3H, s); 2.30 (3H, s).

【０６２２】[0622]

【実施例３１９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−メトキシカルボニ
ルカルバマート（化合物番号D2.73 ）融点：163 −166 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.90
(2H, m); 7.52-7.41 (2H,m); 7.05 (1H, d, J=8.6 Hz);
6.95-6.88 (2H, m); 5.48 (2H, s); 3.76 (6H,s); 2.1
6 (3H, s). Working Example 319 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-methoxycarbonyl
Lecarbamate (Compound No. D2.73) Melting point: 163-166 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.90
(2H, m); 7.52-7.41 (2H, m); 7.05 (1H, d, J = 8.6 Hz);
6.95-6.88 (2H, m); 5.48 (2H, s); 3.76 (6H, s); 2.1
6 (3H, s).

【０６２３】[0623]

【実施例３２０】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−メトキシカルボ
ニルカルバマート（化合物番号D2.74 ）融点：141 −144 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．８
０−７．７５（１Ｈ，ｍ）；７．６０−７．５５
（１Ｈ，ｍ）；７．４１−７．３６（２Ｈ，
ｍ）；７．０４（１Ｈ，ｄ，Ｊ＝８．４Ｈ
ｚ）；６．９５−６．９０（２Ｈ，ｍ）；５．
３２（２Ｈ，ｓ）；３．７５（３Ｈ，ｓ）；
２．１５（３Ｈ，ｓ）． Working Example 320 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -2-methylphenyl] -N-methoxycarbo
Nilcarbamate (Compound No. D2.74) Melting point: 141-144 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.8
0-7.75 (1H, m); 7.60-7.55
(1H, m); 7.41-7.36 (2H,
m); 7.04 (1H, d, J = 8.4H
6.95-6.90 (2H, m);
32 (2H, s); 3.75 (3H, s);
2.15 (3H, s).

【０６２４】[0624]

【実施例３２１】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−エトキシカルボニ
ルカルバマート（化合物番号Ｄ２．７５）融点：84−86℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-8.02
(1H, m); 7.94-7.89 (1H,m); 7.52-7.42 (2H, m); 7.04
(1H, d, J=8.4 Hz); 6.95-6.87 (2H, m); 5.48(2H,
m); 4.24-4.20 (2H, m); 3.76 (3H, s); 2.16 (3H, s);
1.21 (3H, t, J=7.1 Hz). Working Example 321 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-ethoxycarboni
Lecarbamate (Compound No. D2.75) Melting point: 84-86 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-8.02
(1H, m); 7.94-7.89 (1H, m); 7.52-7.42 (2H, m); 7.04
(1H, d, J = 8.4 Hz); 6.95-6.87 (2H, m); 5.48 (2H,
m); 4.24-4.20 (2H, m); 3.76 (3H, s); 2.16 (3H, s);
1.21 (3H, t, J = 7.1 Hz).

【０６２５】[0625]

【実施例３２２】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−エトキシカルボ
ニルカルバマート（化合物番号D2.76 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.59-7.55 (1H,m); 7.40-7.35 (2H, m); 7.04
(1H, d, J=8.5 Hz); 6.95-6.87 (2H, m); 5.32(2H,
s); 4.21 (2H, qd, J=7.1 & 2.2 Hz); 3.75 (3H, s);
2.15 (3H, s); 1.20(3H, t, J=7.1 Hz). Working Example 322 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -2-methylphenyl] -N-ethoxycarbo
Nylcarbamate (Compound No. D2.76) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.59-7.55 (1H, m); 7.40-7.35 (2H, m); 7.04
(1H, d, J = 8.5 Hz); 6.95-6.87 (2H, m); 5.32 (2H,
s); 4.21 (2H, qd, J = 7.1 & 2.2 Hz); 3.75 (3H, s);
2.15 (3H, s); 1.20 (3H, t, J = 7.1 Hz).

【０６２６】[0626]

【実施例３２３】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−プロポキシカルボ
ニルカルバマート（化合物番号D2.77 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
７−８．０１（１Ｈ，ｍ）；７．９３−７．８８
（１Ｈ，ｍ）；７．５６−７．３８（２Ｈ，
ｍ）；７．０６−６．８５（３Ｈ，ｍ）；５．
４８（２Ｈ，ｓ）；４．１０（２Ｈ，ｔ，
Ｊ＝６．６Ｈｚ）；３．７６（３Ｈ，ｓ）；
２．１６（３Ｈ，ｓ）；１．６２−１．５０
（２Ｈ，ｍ）；０．７９（３Ｈ，ｔ，Ｊ＝
７．３Ｈｚ）． Working Example 323 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-propoxycarbo
Nylcarbamate (Compound No. D2.77) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
7-8.01 (1H, m); 7.93-7.88
(1H, m); 7.56-7.38 (2H,
7. m); 7.06-6.85 (3H, m);
48 (2H, s); 4.10 (2H, t,
J = 6.6 Hz); 3.76 (3H, s);
2.16 (3H, s); 1.62-1.50
(2H, m); 0.79 (3H, t, J =
7.3 Hz).

【０６２７】[0627]

【実施例３２４】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−プロポキシカル
ボニルカルバマート（化合物番号D2.78 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.59-7.55 (1H,m); 7.43-7.35 (2H, m); 7.04
(1H, d, J=8.3 Hz); 6.95-6.87 (2H, m); 5.32(2H,
s); 4.10 (2H, t, J=6.6 Hz); 3.75 (3H, s); 2.15 (3
H, s); 1.59-1.51 (2H, m); 0.78 (3H, t, J=7.4 Hz). Working Example 324 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxy) -2-methylphenyl] -N-propoxycal
Bonyl carbamate (Compound No. D2.78) oil NMR spectrum (200 MHz, CDCl ₃ ), δppm: 7.79-7.75
(1H, m); 7.59-7.55 (1H, m); 7.43-7.35 (2H, m); 7.04
(1H, d, J = 8.3 Hz); 6.95-6.87 (2H, m); 5.32 (2H,
s); 4.10 (2H, t, J = 6.6 Hz); 3.75 (3H, s); 2.15 (3
H, s); 1.59-1.51 (2H, m); 0.78 (3H, t, J = 7.4 Hz).

【０６２８】[0628]

【実施例３２５】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−イソプロポキシカ
ルボニルカルバマート（化合物番号D2.79 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H, d
d, J=8.1 & 0.7 Hz); 7.92 (1H, d, J=8.4 Hz); 7.55-
7.41 (2H, m); 7.03 (1H, d, J=8.6 Hz); 6.93-6.85 (2
H, m); 5, 48 (2H, s); 5.00 (1H, quintet, J=6.4 H
z); 3.75 (3H, s); 2.16 (3H, s); 1.20 (3H, s); 1.17
(3H, s). Working Example 325 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-isopropoxyca
Rubonyl carbamate (Compound No. D2.79) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H, d
d, J = 8.1 & 0.7 Hz); 7.92 (1H, d, J = 8.4 Hz); 7.55-
7.41 (2H, m); 7.03 (1H, d, J = 8.6 Hz); 6.93-6.85 (2
H, m); 5, 48 (2H, s); 5.00 (1H, quintet, J = 6.4 H
z); 3.75 (3H, s); 2.16 (3H, s); 1.20 (3H, s); 1.17
(3H, s).

【０６２９】[0629]

【実施例３２６】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−ブトキシカルボニ
ルカルバマート（化合物番号D2.80 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
４（１Ｈ，ｄ，Ｊ＝８．０Ｈｚ）；７．９１
（１Ｈ，ｄｄ，Ｊ＝７．７＆２．２Ｈｚ）；
７．５６−７．４２（２Ｈ，ｍ）；７．０５−
６．８５（３Ｈ，ｍ）；５．４８（２Ｈ，
ｓ）；３．７６（３Ｈ，ｓ）；２．１５（３
Ｈ，ｓ）；１．５６−１．４６（２Ｈ，ｍ）；
１．２７−１．２０（２Ｈ，ｍ）；０．８２
（３Ｈ，ｔ，Ｊ＝７．３Ｈｚ）． Working Example 326 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-butoxycarboni
Rucarbamate (Compound No. D2.80) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
4. (1H, d, J = 8.0 Hz); 7.91
(1H, dd, J = 7.7 & 2.2 Hz);
7.56-7.42 (2H, m); 7.05-
6.85 (3H, m); 5.48 (2H, m)
s); 3.76 (3H, s); 2.15 (3
H, s); 1.56-1.46 (2H, m);
1.27-1.20 (2H, m); 0.82
(3H, t, J = 7.3 Hz).

【０６３０】[0630]

【実施例３２７】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−ブトキシカルボ
ニルカルバマート（化合物番号Ｄ２．８１）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H,m); 7.43-7.36 (2H, m); 7.03
(1H, d, J=8.5 Hz); 6.96-6.87 (2H, m); 5.32(2H,
m); 4.14 (2H, t, J=6.6 Hz); 3.76 (3H, s); 2.15 (3
H, s); 1.60-1.46 (2H, m); 1.31-1.13 (2H, m); 0.83
(3H, t, J=7.2 Hz). Working Example 327 Methyl N- [4- (benzoxazol-2-ylmethy)
Toxi) -2-methylphenyl] -N-butoxycarbo
Nylcarbamate (Compound No. D2.81) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H, m); 7.43-7.36 (2H, m); 7.03
(1H, d, J = 8.5 Hz); 6.96-6.87 (2H, m); 5.32 (2H,
m); 4.14 (2H, t, J = 6.6 Hz); 3.76 (3H, s); 2.15 (3
H, s); 1.60-1.46 (2H, m); 1.31-1.13 (2H, m); 0.83
(3H, t, J = 7.2 Hz).

【０６３１】[0631]

【実施例３２８】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−イソブトキシカル
ボニルカルバマート（化合物番号D2.82 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H, d
d, J=7.3 & 1.3 Hz); 7.93-7.89 (1H, m); 7.52-7.41
(2H, m); 7.07-6.89 (3H, m); 5.48 (2H, s); 3.91 (2
H, d, J=6.4 Hz); 3.78 (3H, s); 2.16 (3H, s); 1.80-
1.70 (1H, m); 0.73(3H, s); 0.77 (3H, s).Example 328: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-isobutoxycal
Bonyl carbamate (Compound No. D2.82) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H, d
d, J = 7.3 & 1.3 Hz); 7.93-7.89 (1H, m); 7.52-7.41
(2H, m); 7.07-6.89 (3H, m); 5.48 (2H, s); 3.91 (2
H, d, J = 6.4 Hz); 3.78 (3H, s); 2.16 (3H, s); 1.80-
1.70 (1H, m); 0.73 (3H, s); 0.77 (3H, s).

【０６３２】[0632]

【実施例３２９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２，２，２−ト
リクロロエトキシカルボニル）カルバマート（化合物番
号D2.83 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
６−７．８８（２Ｈ，ｍ）；７．５５−７．３７
（２Ｈ，ｍ）；７．０８（１Ｈ，ｄ，Ｊ＝
８．６Ｈｚ）；６．９５−６．８６（２Ｈ，
ｍ）；５．４９（２Ｈ，ｓ）；４．７４（２
Ｈ，ｓ）；３．８０（３Ｈ，ｓ）；２．２０
（３Ｈ，ｓ）． Working Example 329 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2,2,2-to
Lichloroethoxycarbonyl) carbamate (Compound No.
No. D2.83) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
6-7.88 (2H, m); 7.55-7.37.
(2H, m); 7.08 (1H, d, J =
8.6 Hz); 6.95-6.86 (2H,
m); 5.49 (2H, s); 4.74 (2
H, s); 3.80 (3H, s); 2.20
(3H, s).

【０６３３】[0633]

【実施例３３０】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−（２，２，２−
トリクロロエトキシカルボニル）カルバマート（化合物
番号Ｄ．２．８４）融点：102 −105 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.59-7.55 (1H,m); 7.41-7.36 (2H, m); 7.09
(1H, d, J=8.4 Hz); 6.97-6.90 (2H, m); 5.33(2H,
s); 4.74 (2H, s); 3.80 (3H, s); 2.20 (3H, s). Working Example 330 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -2-methylphenyl] -N- (2,2,2-
Trichloroethoxycarbonyl) carbamate (compound
Number D. 2.84) Melting point: 102-105 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.59-7.55 (1H, m); 7.41-7.36 (2H, m); 7.09
(1H, d, J = 8.4 Hz); 6.97-6.90 (2H, m); 5.33 (2H,
s); 4.74 (2H, s); 3.80 (3H, s); 2.20 (3H, s).

【０６３４】[0634]

【実施例３３１】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−フェノキシカルボ
ニルカルバマート（化合物番号D2.85 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H, d
d, J=7.3 & 1.4 Hz); 7.93-7.89 (1H, m); 7.55-7.29
(5H, m); 7.25-6.96 (5H, m); 5.30 (2H.s); 3.81(3H,
s); 2.29 (3H, s). Working Example 331 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-phenoxycarbo
Nylcarbamate (Compound No. D2.85) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H, d
d, J = 7.3 & 1.4 Hz); 7.93-7.89 (1H, m); 7.55-7.29
(5H, m); 7.25-6.96 (5H, m); 5.30 (2H.s); 3.81 (3H,
s); 2.29 (3H, s).

【０６３５】[0635]

【実施例３３２】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−フルオロフェニル］カルバマート（化合物
番号C9.4）融点：124 −127 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=8.1 Hz); 7.96-7.81(2H, m); 7.55-7.38 (2H, m);
6.85-6.79 (2H, m); 6.64 (1H, br.s); 5.45 (2H, s);
3.78 (3H, s). Working Example 332 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-fluorophenyl] carbamate (compound
No. C9.4) Melting point: 124-127 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 8.1 Hz); 7.96-7.81 (2H, m); 7.55-7.38 (2H, m);
6.85-6.79 (2H, m); 6.64 (1H, br.s); 5.45 (2H, s);
3.78 (3H, s).

【０６３６】[0636]

【実施例３３３】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−３−フルオロフェニル］カルバマート（化合物
番号C9.23 ）融点：112 −115 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.0 Hz); 7.91 (1H,d, J=8.0 Hz); 7.55-7.35 (3
H, m); 7.03 (1H, t, J=8.6 Hz); 6.92 (1H, dd,J=8.6
& 2.3 Hz); 6.55 (1H, br.s); 5.51 (2H, s); 3.77 (3
H, s). Working Example 333 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -3-fluorophenyl] carbamate (compound
No. C9.23) Melting point: 112-115 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.0 Hz); 7.91 (1H, d, J = 8.0 Hz); 7.55-7.35 (3
H, m); 7.03 (1H, t, J = 8.6 Hz); 6.92 (1H, dd, J = 8.6
& 2.3 Hz); 6.55 (1H, br.s); 5.51 (2H, s); 3.77 (3
H, s).

【０６３７】[0637]

【実施例３３４】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−３−ニトロフェニル］カルバマート（化合物番
号C10.64）融点：198 −200 ℃ ＮＭＲスペクトル(200MHz, DMSO-d₆）, δppm: 9.80 (1
H, br.s); 8.16 (1H, d,J=2.6 Hz); 8.04-7.97 (2H,
m); 7.69 (1H, dd, J=9.0 & 2.6 Hz); 7.55-7.40(2H,
m); 7.35 (1H, d, J=9.0 Hz); 5.65 (2H, s); 3.73 (3
H, s). Working Example 334: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -3-nitrophenyl] carbamate (compound number
No. C10.64) Melting point: 198-200 ° C NMR spectrum (200 MHz, DMSO-d ₆ ), δ ppm: 9.80 (1
H, br.s); 8.16 (1H, d, J = 2.6 Hz); 8.04-7.97 (2H,
m); 7.69 (1H, dd, J = 9.0 & 2.6 Hz); 7.55-7.40 (2H,
m); 7.35 (1H, d, J = 9.0 Hz); 5.65 (2H, s); 3.73 (3
H, s).

【０６３８】[0638]

【実施例３３５】メチルＮ−［４−（４−メチルベンゾチアゾール−２
−イルメトキシ）フェニル］カルバマート（化合物番号
F1.3）融点：147 −150 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.75-7.70
(1H, m); 7.35-7.26 (4H,m); 7.00 (2H, dd, J=6.8 &
2.3 Hz); 6.47-6.46 (1H, br.m); 5.47 (2H, s);3.76
(3H, s); 2.76 (3H, s).Working Example 335 Methyl N- [4- (4-methylbenzothiazole-2)
-Ylmethoxy) phenyl] carbamate (compound number
F1.3) Melting point: 147-150 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.75-7.70
(1H, m); 7.35-7.26 (4H, m); 7.00 (2H, dd, J = 6.8 &
2.3 Hz); 6.47-6.46 (1H, br.m); 5.47 (2H, s); 3.76
(3H, s); 2.76 (3H, s).

【０６３９】[0639]

【実施例３３６】メチルＮ−［４−（４−メトキシベンゾチアゾール−
２−イルメトキシ）フェニル］カルバマート（化合物番
号F3.3）融点：117 −120 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．５
０−７．２０（４Ｈ，ｍ）；７．０１−６．９０
（３Ｈ，ｍ）；６．４６（１Ｈ，ｂｒ．ｓ）；
５．４７（２Ｈ，ｓ）；４．０７（３Ｈ，
ｓ）；３．７８（３Ｈ，ｓ）．Working Example 336 Methyl N- [4- (4-methoxybenzothiazole-)
2-ylmethoxy) phenyl] carbamate (compound number
No. F3.3) Melting point: 117-120 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.5
0-7.20 (4H, m); 7.01-6.90
(3H, m); 6.46 (1H, br.s);
5.47 (2H, s); 4.07 (3H,
s); 3.78 (3H, s).

【０６４０】[0640]

【実施例３３７】メチルＮ−［４−（６−メトキシベンゾチアゾール−
２−イルメトキシ）フェニル］カルバマート（化合物番
号Ｆ３．２２）融点：118 −120 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.90 (1H,
d, J=8.9 Hz); 7.33 (1H,d, J=2.7 Hz); 7.28-7.26 (3
H, m); 7.12-7.06 (1H, m); 6.99 (2H, dd, J=6.8& 2.3
Hz); 6.48-6.47 (1H, br.m); 5.41 (2H, s); 3.88 (3
H, s); 3.76 (3H,s).Working Example 337 Methyl N- [4- (6-methoxybenzothiazole-
2-ylmethoxy) phenyl] carbamate (compound number
No. F3.22) melting point: 118-120 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.90 (1H,
d, J = 8.9 Hz); 7.33 (1H, d, J = 2.7 Hz); 7.28-7.26 (3
H, m); 7.12-7.06 (1H, m); 6.99 (2H, dd, J = 6.8 & 2.3
Hz); 6.48-6.47 (1H, br.m); 5.41 (2H, s); 3.88 (3
H, s); 3.76 (3H, s).

【０６４１】[0641]

【実施例３３８】メチルＮ−［４−（７−メトキシベンゾチアゾール−
２−イルメトキシ）フェニル］カルバマート（化合物番
号F3.31 ）融点：174 −176 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.67-7.63
(1H, m); 7.44 (1H, t, J=8.1 Hz); 7.32-7.26 (3H,
m); 6.99 (2H, dd, J=6.8 & 2.3 Hz); 6.84 (1H, d,J=
7.3 Hz); 6.48-6.47 (1H, br.m); 5.45 (2H, s); 3.98
(3H, s); 3.76 (3H,s).Working Example 338 Methyl N- [4- (7-methoxybenzothiazole-
2-ylmethoxy) phenyl] carbamate (compound number
No. F3.31) Melting point: 174-176 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.67-7.63
(1H, m); 7.44 (1H, t, J = 8.1 Hz); 7.32-7.26 (3H,
m); 6.99 (2H, dd, J = 6.8 & 2.3 Hz); 6.84 (1H, d, J =
(7.3 Hz); 6.48-6.47 (1H, br.m); 5.45 (2H, s); 3.98
(3H, s); 3.76 (3H, s).

【０６４２】[0642]

【実施例３３９】メチルＮ−［４−（５−フルオロベンゾチアゾール−
２−イルメトキシ）フェニル］カルバマート（化合物番
号F4.12 ）融点：174 −176 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.82 (1H, d
d, J=8.8 & 5.0 Hz); 7.70 (1H, dd, J=9.6 & 2.7 Hz);
7.15 (4H, m); 7.18 (1H, td, J=8.8 & 2.7 Hz); 6.50
(1H, br.s); 5.45 (2H, s); 3.76 (3H, s).Working Example 339 Methyl N- [4- (5-fluorobenzothiazole-
2-ylmethoxy) phenyl] carbamate (compound number
No. F4.12) Melting point: 174-176 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.82 (1H, d
d, J = 8.8 & 5.0 Hz); 7.70 (1H, dd, J = 9.6 & 2.7 Hz);
7.15 (4H, m); 7.18 (1H, td, J = 8.8 & 2.7 Hz); 6.50
(1H, br.s); 5.45 (2H, s); 3.76 (3H, s).

【０６４３】[0643]

【実施例３４０】メチルＮ−［４−（５−フルオロベンゾオキサゾール
−２−イルメトキシ）フェニル］カルバマート（化合物
番号F4.14 ）融点：133 −134 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.53-7.41
(2H, m); 7.34-7.25 (3H,m); 7.16-7.05 (1H, m); 7.00
(2H, dd, J=6.8 & 2.3 Hz); 6.49-6.48 (1H, br.m);
5.28 (2H, s); 3.76 (3H, s).Working Example 340 Methyl N- [4- (5-fluorobenzoxazole)
-2-ylmethoxy) phenyl] carbamate (compound
No. F4.14) melting point: 133-134 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.53-7.41
(2H, m); 7.34-7.25 (3H, m); 7.16-7.05 (1H, m); 7.00
(2H, dd, J = 6.8 & 2.3 Hz); 6.49-6.48 (1H, br.m);
5.28 (2H, s); 3.76 (3H, s).

【０６４４】[0644]

【実施例３４１】メチルＮ−［４−（６−フルオロベンゾオキサゾール
−２−イルメトキシ）フェニル］カルバマート（化合物
番号F4.33 ）融点：120 −122 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.68 (1H, d
d, J=8.8 & 5.0 Hz); 7.34-7.26 (3H, m); 7.16-7.06
(1H, m); 7.01 (2H, dd, J=6.8 & 2.3 Hz); 6.49-6.48
(1H, br.m); 5.27 (2H, s); 3.76 (3H, s).Working Example 341 Methyl N- [4- (6-fluorobenzoxazole)
-2-ylmethoxy) phenyl] carbamate (compound
No. F4.33) melting point: 120-122 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.68 (1H, d
d, J = 8.8 & 5.0 Hz); 7.34-7.26 (3H, m); 7.16-7.06
(1H, m); 7.01 (2H, dd, J = 6.8 & 2.3 Hz); 6.49-6.48
(1H, br.m); 5.27 (2H, s); 3.76 (3H, s).

【０６４５】[0645]

【実施例３４２】メチルＮ−［４−（７−フルオロベンゾチアゾール−
２−イルメトキシ）フェニル］カルバマート（化合物番
号F4.41 ）融点：136 −139 ℃ ＮＭＲスペクトル(200Mz,CDCl₃),δppm: 7.83 (1H, d,
J=8.3 Hz); 7.51-7.41 (1H, m); 7.32 (2H, d, J=9.0 H
z); 7.12 (1H, t, J=8.3 Hz); 6.99 (2H, d, J=9.0 H
z); 6.54 (1H, br.s); 5.46 (2H, s); 3.76 (3H, s).Working Example 342 Methyl N- [4- (7-fluorobenzothiazole-
2-ylmethoxy) phenyl] carbamate (compound number
No. F4.41) Melting point: 136-139 ° C. NMR spectrum (200 Mz, CDCl ₃ ), δ ppm: 7.83 (1H, d,
J = 8.3 Hz); 7.51-7.41 (1H, m); 7.32 (2H, d, J = 9.0 H
z); 7.12 (1H, t, J = 8.3 Hz); 6.99 (2H, d, J = 9.0 H
z); 6.54 (1H, br.s); 5.46 (2H, s); 3.76 (3H, s).

【０６４６】[0646]

【実施例３４３】メチルＮ−［４−（７−フルオロベンゾオキサゾール
−２−イルメトキシ）フェニル］カルバマート（化合物
番号F4.43 ）融点：120 −123 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．５
５（１Ｈ，ｄｄ，Ｊ＝７．９＆１．０Ｈ
ｚ）；７．３５−７．２５（２Ｈ，ｍ）；７．
１８−７．０５（１Ｈ，ｍ）；７．０２（２
Ｈ，ｄｄ，Ｊ＝６．８＆２．３Ｈｚ）；
６．５０（１Ｈ，ｂｒ．ｓ）；５．３１（２Ｈ，
ｓ）；３．７６（３Ｈ，ｓ）．Working Example 343 Methyl N- [4- (7-fluorobenzoxazole)
-2-ylmethoxy) phenyl] carbamate (compound
No. F4.43) melting point: 120-123 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.5
5 (1H, dd, J = 7.9 & 1.0 H
z); 7.35-7.25 (2H, m);
18-7.05 (1H, m); 7.02 (2
H, dd, J = 6.8 & 2.3 Hz);
6.50 (1H, br.s); 5.31 (2H, br.s)
s); 3.76 (3H, s).

【０６４７】[0647]

【実施例３４４】メチルＮ−［４−（５−クロロベンゾチアゾール−２
−イルメトキシ）フェニル］カルバマート（化合物番号
Ｆ４．６１）融点：211 −213 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.01 (1H,
d, J=2.2 Hz); 7.81 (1H,d, J=8.3 Hz); 7.41-7.26 (3
H, m); 6.98 (2H, dd, J=6.8 & 2.3 Hz); 6.48-6.47 (1
H, br.m); 5.44 (2H, s); 3.76 (3H, s).Working Example 344 Methyl N- [4- (5-chlorobenzothiazole-2)
-Ylmethoxy) phenyl] carbamate (compound number
F4.61) Melting point: 211-213 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.01 (1H,
d, J = 2.2 Hz); 7.81 (1H, d, J = 8.3 Hz); 7.41-7.26 (3
H, m); 6.98 (2H, dd, J = 6.8 & 2.3 Hz); 6.48-6.47 (1
H, br.m); 5.44 (2H, s); 3.76 (3H, s).

【０６４８】[0648]

【実施例３４５】メチルＮ−［４−（６−クロロベンゾチアゾール−２
−イルメトキシ）フェニル］カルバマート（化合物番号
F4.71 ）融点 195−197 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.93 (1H,
d, J=4.5 Hz); 7.87 (1H,d, J=2.3 Hz); 7.59 (1H, dd,
J=8.8 & 2.2 Hz); 7.34-7.26 (2H, m); 6.98 (2H, dd,
J=6.8 & 2.3 Hz); 6.49-6.45 (1H, br.m); 5.44 (2H,
s); 3.76 (3H, s).Working Example 345: Methyl N- [4- (6-chlorobenzothiazole-2)
-Ylmethoxy) phenyl] carbamate (compound number
F4.71) Melting point 195-197 ° C NMR spectrum (200MHz, CDCl ₃ ), δppm: 7.93 (1H,
d, J = 4.5 Hz); 7.87 (1H, d, J = 2.3 Hz); 7.59 (1H, dd,
J = 8.8 & 2.2 Hz); 7.34-7.26 (2H, m); 6.98 (2H, dd,
J = 6.8 & 2.3 Hz); 6.49-6.45 (1H, br.m); 5.44 (2H,
s); 3.76 (3H, s).

【０６４９】[0649]

【実施例３４６】メチルＮ−［４−（７−クロロベンゾチアゾール−２
−イルメトキシ）フェニル］カルバマート（化合物番号
F4.81 ）融点：159 −162 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.92 (1H, d
d, J=7.4 & 1.8 Hz); 7.49-7.26 (4H, m); 7.00 (2H, d
d, J=6.8 & 2.3 Hz); 6.49-6.45 (1H, br.m); 5.45 (2
H, s); 3.76 (3H, s).Working Example 346 Methyl N- [4- (7-chlorobenzothiazole-2)
-Ylmethoxy) phenyl] carbamate (compound number
F4.81) Melting point: 159-162 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.92 (1H, d
d, J = 7.4 & 1.8 Hz); 7.49-7.26 (4H, m); 7.00 (2H, d
d, J = 6.8 & 2.3 Hz); 6.49-6.45 (1H, br.m); 5.45 (2
H, s); 3.76 (3H, s).

【０６５０】[0650]

【実施例３４７】メチルＮ−［４−（４−トリフルオロメチルベンゾチ
アゾール−２−イルメトキシ）フェニル］カルバマート
（化合物番号F5.3）融点：179 −180 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.10 (1H,
d, J=8.0 Hz); 7.80 (1H,d, J=8.0 Hz); 7.48 (1H, t,
J=8.0 Hz); 7.32 (2H, d, J=8.8 Hz); 6.99 (2H,d, J=
8.8 Hz); 6.48 (1H, br.s); 5.53 (2H, s); 3.77 (3H,
s).Working Example 347 Methyl N- [4- (4-trifluoromethylbenzothio)
Azol-2-ylmethoxy) phenyl] carbamate
(Compound No. F5.3) Melting point: 179-180 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.10 (1H,
d, J = 8.0 Hz); 7.80 (1H, d, J = 8.0 Hz); 7.48 (1H, t,
J = 8.0 Hz); 7.32 (2H, d, J = 8.8 Hz); 6.99 (2H, d, J =
8.8 Hz); 6.48 (1H, br.s); 5.53 (2H, s); 3.77 (3H,
s).

【０６５１】[0651]

【実施例３４８】メチルＮ−［２−メチル−４−（４−メチルベンゾチ
アゾール−２−イルメトキシ）フェニル］カルバマート
（化合物番号G1.3）融点：153 −155 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.75-7.70
(1H, m); 7.60-7.51 (1H,br.m); 7.34-7.26 (2H, m);
6.92-6.85 (2H, m); 6.21-6.19 (1H, br.m); 5.47(2H,
s); 3.76 (3H, s); 2.76 (3H, s); 2.24 (3H, s). Working Example 348 Methyl N- [2-methyl-4- (4-methylbenzothi)
Azol-2-ylmethoxy) phenyl] carbamate
(Compound No. G1.3) Melting point: 153-155 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.75-7.70
(1H, m); 7.60-7.51 (1H, br.m); 7.34-7.26 (2H, m);
6.92-6.85 (2H, m); 6.21-6.19 (1H, br.m); 5.47 (2H, m
s); 3.76 (3H, s); 2.76 (3H, s); 2.24 (3H, s).

【０６５２】[0652]

【実施例３４９】メチルＮ−［２−メチル−４−（５−メチルベンゾチ
アゾール−２−イルメトキシ）フェニル］カルバマート
（化合物番号G1.8）融点：131 −133 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.82-7.74
(3H, m); 7.55-7.50 (1H,br.m); 6.89-6.87 (2H, m);
6.20-6.18 (1H, br.s); 5.44 (2H, s); 3.76 (3H,s);
2.51 (3H, s); 2.23 (3H, s). Working Example 349 Methyl N- [2-methyl-4- (5-methylbenzothi)
Azol-2-ylmethoxy) phenyl] carbamate
(Compound No. G1.8) Melting point: 131-133 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.82-7.74
(3H, m); 7.55-7.50 (1H, br.m); 6.89-6.87 (2H, m);
6.20-6.18 (1H, br.s); 5.44 (2H, s); 3.76 (3H, s);
2.51 (3H, s); 2.23 (3H, s).

【０６５３】[0653]

【実施例３５０】メチルＮ−［２−メチル−４−（６−メチルベンゾチ
アゾール−２−イルメトキシ）フェニル］カルバマート
（化合物番号G1.13 ）融点：153 −155 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．９
０（１Ｈ，ｄ，Ｊ＝８．３Ｈｚ）；７．６８
（１Ｈ，ｄ，Ｊ＝８．９Ｈｚ）；７．５５−
７．４９（１Ｈ，ｂｒ．ｍ）；７．３３−７．２
６（１Ｈ，ｍ）；６．９０−６．８７（２Ｈ，
ｍ）；６．１９（１Ｈ，ｂｒ．ｓ）；５．４
３（２Ｈ，ｓ）；３．７６（３Ｈ，ｓ）；
２．４９（３Ｈ，ｓ）；２．２３（３Ｈ，
ｓ）． Working Example 350 Methyl N- [2-methyl-4- (6-methylbenzothi)
Azol-2-ylmethoxy) phenyl] carbamate
(Compound No. G1.13) Melting point: 153-155 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.9
0 (1H, d, J = 8.3 Hz); 7.68
(1H, d, J = 8.9 Hz); 7.55-
7.49 (1H, br.m); 7.33-7.2
6 (1H, m); 6.90-6.87 (2H,
m); 6.19 (1H, br.s); 5.4
3.76 (3H, s);
2.49 (3H, s); 2.23 (3H,
s).

【０６５４】[0654]

【実施例３５１】メチルＮ−［４−（４−メトキシベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト（化合物番号Ｇ１．３０）融点：125 −126 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.50-7.24
(3H, m); 6.96-6.82 (3H,m); 6.28 (1H, br.s); 5.48
(2H, s); 4.07 (3H, s); 3.77 (3H, s); 2.23 (3H, s).Working Example 351 Methyl N- [4- (4-methoxybenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamer
(Compound No. G1.30) Melting point: 125-126 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.50-7.24
(3H, m); 6.96-6.82 (3H, m); 6.28 (1H, br.s); 5.48
(2H, s); 4.07 (3H, s); 3.77 (3H, s); 2.23 (3H, s).

【０６５５】[0655]

【実施例３５２】メチルＮ−［４−（５−メトキシベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト（化合物番号G1.34 ）融点：159 −161 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.73 (1H,
d, J=8.8 Hz); 7.57-7.50(1H, br.m); 7.51 (1H, d, J=
2.3 Hz); 7.05 (1H, dd, J=8.8 & 2.5 Hz); 6.89-6.86
(2H, m); 6.20 (1H, br.s); 5.43 (2H, s); 3.90 (3H,
s); 3.76 (3H, s); 2.24 (3H, s).Working Example 352 Methyl N- [4- (5-methoxybenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamer
(Compound No. G1.34) Melting point: 159-161 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.73 (1H,
d, J = 8.8 Hz); 7.57-7.50 (1H, br.m); 7.51 (1H, d, J =
2.3 Hz); 7.05 (1H, dd, J = 8.8 & 2.5 Hz); 6.89-6.86
(2H, m); 6.20 (1H, br.s); 5.43 (2H, s); 3.90 (3H,
s); 3.76 (3H, s); 2.24 (3H, s).

【０６５６】[0656]

【実施例３５３】メチルＮ−［４−（７−メトキシベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト（化合物番号G1.44 ）融点：150 −151 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.67-7.63
(1H, m); 7.53-7.45 (1H,br.m); 7.44 (1H, t, J=8.1 H
z); 6.90-6.82 (3H, m); 6.19 (1H, br.s); 5.44(2H,
s); 3.98 (3H, s); 3.76 (3H, s); 2.23 (3H, s).Working Example 353: Methyl N- [4- (7-methoxybenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamer
(Compound No. G1.44) Melting point: 150-151 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.67-7.63
(1H, m); 7.53-7.45 (1H, br.m); 7.44 (1H, t, J = 8.1 H
z); 6.90-6.82 (3H, m); 6.19 (1H, br.s); 5.44 (2H,
s); 3.98 (3H, s); 3.76 (3H, s); 2.23 (3H, s).

【０６５７】[0657]

【実施例３５４】メチルＮ−［４−（４−フルオロベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト（化合物番号G1.52 ）融点：165 −167 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.67 (1H,
d, J=7.9 Hz); 7.43-7.15(3H, m); 6.88-6.86 (2H, m);
6.23-6.18 (1H, br.m); 5.48 (2H, s); 3.76 (3H, s);
2.24 (3H, s).Working Example 354 Methyl N- [4- (4-fluorobenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamer
(Compound No. G1.52) Melting point: 165-167 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.67 (1H,
d, J = 7.9 Hz); 7.43-7.15 (3H, m); 6.88-6.86 (2H, m);
6.23-6.18 (1H, br.m); 5.48 (2H, s); 3.76 (3H, s);
2.24 (3H, s).

【０６５８】[0658]

【実施例３５５】メチルＮ−［４−（７−フルオロベンゾチアゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト（化合物番号G1.67 ）融点：121 −122 ℃ ＮＭＲスペクトル(200Mz,CDCl₃),δppm: 7.83 (1H, d,
J=8.4 Hz); 7.56-7.40 (2H, m); 7.12 (1H, t, J=8.4 H
z); 6.91-6.83 (2H, m); 6.23 (1H, br.s); 5.45(2H,
s); 3.76 (3H, s); 2.24 (3H, s).Working Example 355: Methyl N- [4- (7-fluorobenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamer
(Compound No. G1.67) Melting point: 121-122 ° C. NMR spectrum (200 Mz, CDCl ₃ ), δ ppm: 7.83 (1H, d,
J = 8.4 Hz); 7.56-7.40 (2H, m); 7.12 (1H, t, J = 8.4 H
z); 6.91-6.83 (2H, m); 6.23 (1H, br.s); 5.45 (2H,
s); 3.76 (3H, s); 2.24 (3H, s).

【０６５９】[0659]

【実施例３５６】メチルＮ−［４−（５−クロロベンゾチアゾール−２
−イルメトキシ）−２−メチルフェニル］カルバマート
（化合物番号G1.74 ）融点：179 −182 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.01 (1H,
d, J=1.9 Hz); 7.81 (1H,d, J=8.2 Hz); 7.59-7.50 (1
H, br.m); 7.41-7.36 (1H, m); 6.88-6.85 (2H, m); 6.
21-6.15 (1H, br.m); 5.44 (2H, s); 3.76 (3H, s); 2.
24 (3H, s).Working Example 356: Methyl N- [4- (5-chlorobenzothiazole-2)
-Ylmethoxy) -2-methylphenyl] carbamate
(Compound No. G1.74) Melting point: 179-182 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.01 (1H,
d, J = 1.9 Hz); 7.81 (1H, d, J = 8.2 Hz); 7.59-7.50 (1
H, br.m); 7.41-7.36 (1H, m); 6.88-6.85 (2H, m); 6.
21-6.15 (1H, br.m); 5.44 (2H, s); 3.76 (3H, s); 2.
24 (3H, s).

【０６６０】[0660]

【実施例３５７】メチルＮ−［４−（６−クロロベンゾチアゾール−２
−イルメトキシ）−２−メチルフェニル］カルバマート
（化合物番号G1.81 ）融点：150 −152 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．９
５−７．８７（２Ｈ，ｍ）；７．６０−７．５０
（１Ｈ，ｂｒ．ｍ）；７．４６（１Ｈ，ｄｄ，
Ｊ＝８．６＆２．０Ｈｚ）；６．８８−６．
８５（２Ｈ，ｍ）；６．２１−６．２０（１
Ｈ，ｂｒ．ｍ）；５．４３（２Ｈ，ｓ）；３．
７６（３Ｈ，ｓ）；２．２４（３Ｈ，ｓ）．Working Example 357 Methyl N- [4- (6-chlorobenzothiazole-2)
-Ylmethoxy) -2-methylphenyl] carbamate
(Compound No. G1.81) Melting point: 150-152 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.9
5-7.87 (2H, m); 7.60-7.50
(1H, br, m); 7.46 (1H, dd,
J = 8.6 & 2.0 Hz); 6.88-6.
85 (2H, m); 6.21-6.20 (1
H, br. m); 5.43 (2H, s);
76 (3H, s); 2.24 (3H, s).

【０６６１】[0661]

【実施例３５８】メチルＮ−［４−（７−クロロベンゾチアゾール−２
−イルメトキシ）−２−メチルフェニル］カルバマート
（化合物番号Ｇ１．８５）融点：135 −137 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.92 (1H, d
d, J=7.4 & 1.7 Hz); 7.60-7.49 (1H, br.m); 7.49-7.3
8 (2H, m); 6.89-6.86 (2H, m); 6.22-6.18 (1H,br.m);
5.44 (2H, s); 3.76 (3H, s); 2.24 (3H, s).Working Example 358 Methyl N- [4- (7-chlorobenzothiazole-2)
-Ylmethoxy) -2-methylphenyl] carbamate
(Compound No. G1.85) Melting point: 135-137 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.92 (1H, d
d, J = 7.4 & 1.7 Hz); 7.60-7.49 (1H, br.m); 7.49-7.3
8 (2H, m); 6.89-6.86 (2H, m); 6.22-6.18 (1H, br.m);
5.44 (2H, s); 3.76 (3H, s); 2.24 (3H, s).

【０６６２】[0662]

【実施例３５９】メチルＮ−［２−メチル−４−（４−トリフルオロメ
チルベンゾチアゾール−２−イルメトキシ）フェニル］
カルバマート（化合物番号G1.89 ）融点：180 −181 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.10 (1H,
d, J=8.0 Hz); 7.80 (1H,d, J=8.0 Hz); 7.57-7.49 (1
H, m); 7.48 (1H, t, J=8.0 Hz); 6.91-6.86 (2H,m);
6.21 (1H, br.s); 5.53 (2H, s); 3.76 (3H, s); 2.24
(3H, s).Working Example 359 Methyl N- [2-methyl-4- (4-trifluoromethane)
Tylbenzothiazol-2-ylmethoxy) phenyl]
Carbamate (Compound No. G1.89) Melting point: 180-181 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.10 (1H,
d, J = 8.0 Hz); 7.80 (1H, d, J = 8.0 Hz); 7.57-7.49 (1
H, m); 7.48 (1H, t, J = 8.0 Hz); 6.91-6.86 (2H, m);
6.21 (1H, br.s); 5.53 (2H, s); 3.76 (3H, s); 2.24
(3H, s).

【０６６３】[0663]

【実施例３６０】メチルＮ−［２−メチル−４−（５−トリフルオロメ
チルベンゾチアゾール−２−イルメトキシ）フェニル］
カルバマート（化合物番号G1.94 ）融点：173 −176 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.29 (1H,
s); 8.01 (1H, d, J=9.0Hz); 7.66-7.47 (2H, m); 6.86
(2H, m); 6.25 (1H, br.s); 5.47 (2H, s); 2.25 (3H,
s).Working Example 360 Methyl N- [2-methyl-4- (5-trifluoromethane)
Tylbenzothiazol-2-ylmethoxy) phenyl]
Carbamate (Compound No. G1.94) Melting point: 173-176 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.29 (1H,
s); 8.01 (1H, d, J = 9.0Hz); 7.66-7.47 (2H, m); 6.86
(2H, m); 6.25 (1H, br.s); 5.47 (2H, s); 2.25 (3H,
s).

【０６６４】[0664]

【実施例３６１】メチルＮ−［２−メチル−４−（６−トリフルオロメ
チルベンゾチアゾール−２−イルメトキシ）フェニル］
カルバマート（化合物番号G1.99 ）融点：165 −168 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.20-8.09
(2H, m); 7.77-7.71 (1H,m); 7.60-7.58 (1H, m); 6.91
-6.85 (2H, m); 6.22-6.20 (1H, br.m); 5.47 (2H, s);
3.76 (3H, s); 2.24 (3H, s).Working Example 361 Methyl N- [2-methyl-4- (6-trifluoromethyl)
Tylbenzothiazol-2-ylmethoxy) phenyl]
Carbamate (Compound No. G1.99) Melting point: 165 ° -168 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.20-8.09
(2H, m); 7.77-7.71 (1H, m); 7.60-7.58 (1H, m); 6.91
-6.85 (2H, m); 6.22-6.20 (1H, br.m); 5.47 (2H, s);
3.76 (3H, s); 2.24 (3H, s).

【０６６５】[0665]

【実施例３６２】メチルＮ−［４−（５−フルオロベンゾチアゾール−
２−イルメトキシ）−２−メトキシフェニル］カルバマ
ート（化合物番号G8.33 ）融点：159 −162 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.95 (1H, b
r.d); 7.82 (1H, dd, J=8.8 & 5.1 Hz); 7.71 (1H, dd,
J=9.5 & 2.5 Hz); 7.18 (1H, td, J=8.8 & 2.5Hz); 7.
01 (1H, br.s); 6.61 (1H, s); 6.59 (1H, dd, J=9.5 &
5.1 Hz); 5.45(2H, s); 3.76 (3H, s).Working Example 362 Methyl N- [4- (5-fluorobenzothiazole-
2-ylmethoxy) -2-methoxyphenyl] carbama
(Compound No. G8.33) Melting point: 159-162 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.95 (1H, b
rd); 7.82 (1H, dd, J = 8.8 & 5.1 Hz); 7.71 (1H, dd,
J = 9.5 & 2.5 Hz); 7.18 (1H, td, J = 8.8 &2.5Hz); 7.
01 (1H, br.s); 6.61 (1H, s); 6.59 (1H, dd, J = 9.5 &
5.1 Hz); 5.45 (2H, s); 3.76 (3H, s).

【０６６６】[0666]

【実施例３６３】エチルＮ−［４−（５−フルオロベンゾチアゾール−
２−イルメトキシ）−２−メトキシフェニル］カルバマ
ート（化合物番号G8.36 ）融点：157 −159 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.00 (1H, b
r.d, J=7.9 Hz); 7.82 (1H, dd, J=8.8 & 5.1 Hz); 7.7
1 (1H, dd, J=9.5 & 2.4 Hz); 7.18 (1H, td, J=8.8 &
2.5 Hz); 6.99 (1H, br.s); 6.62-6.56 (2H, m); 5.45
(2H, s); 4.21 (2H, q, J=7.2 Hz); 3.86 (3H, s); 1.3
1 (3H, t, J=7.2 Hz).Working Example 363 Ethyl N- [4- (5-fluorobenzothiazole-
2-ylmethoxy) -2-methoxyphenyl] carbama
(Compound No. G8.36) Melting point: 157-159 ° C NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.00 (1H, b
rd, J = 7.9 Hz); 7.82 (1H, dd, J = 8.8 & 5.1 Hz); 7.7
1 (1H, dd, J = 9.5 & 2.4 Hz); 7.18 (1H, td, J = 8.8 &
2.5 Hz); 6.99 (1H, br.s); 6.62-6.56 (2H, m); 5.45
(2H, s); 4.21 (2H, q, J = 7.2 Hz); 3.86 (3H, s); 1.3
1 (3H, t, J = 7.2 Hz).

【０６６７】[0667]

【実施例３６４】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−トリフルオロメチルフェニル］カルバマー
ト（化合物番号C10.4 ）融点：133 −135 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
７−７．８９（３Ｈ，ｍ）；７．５２−７．４２
（２Ｈ，ｍ）；７．２９−７．２０（２Ｈ，
ｍ）；６．８１（１Ｈ，ｂｒ．ｓ）；５．５０
（２Ｈ，ｓ）；３．７８（３Ｈ，ｓ）． Working Example 364 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-trifluoromethylphenyl] carbamer
(Compound No. C10.4) Melting point: 133-135 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
7-7.89 (3H, m); 7.52-7.42
(2H, m); 7.29-7.20 (2H, m)
m); 6.81 (1H, br.s); 5.50
(2H, s); 3.78 (3H, s).

【０６６８】[0668]

【実施例３６５】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−ニトロフェニル］カルバマート（化合物番
号Ｃ１０．４８）融点：184 −186 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 9.65 (1H, b
r.s); 8.51 (1H, d, J=9.2 Hz); 8.08-8.04 (1H, m);
7.94-7.85 (2H, m); 7.53-7.36 (3H, m); 5.52 (2H,
s); 3.82 (3H, s). Working Example 365 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-nitrophenyl] carbamate (compound number
No. C10.48) Melting point: 184-186 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 9.65 (1H, b
rs); 8.51 (1H, d, J = 9.2 Hz); 8.08-8.04 (1H, m);
7.94-7.85 (2H, m); 7.53-7.36 (3H, m); 5.52 (2H, m
s); 3.82 (3H, s).

【０６６９】[0669]

【実施例３６６】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）フェニル］カルバマート（化合物番号A1.6）融点：115 −118 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.78-7.74
(1H, m); 7.58-7.54 (1H,m); 7.42-7.29 (4H, m); 7.02
(2H, d, J=9.0 Hz); 6.54 (1H, br.s); 5.30 (2H, s);
3.75 (3H, s). Working Example 366 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) phenyl] carbamate (Compound No. A1.6) Melting point: 115-118 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.78-7.74
(1H, m); 7.58-7.54 (1H, m); 7.42-7.29 (4H, m); 7.02
(2H, d, J = 9.0 Hz); 6.54 (1H, br.s); 5.30 (2H, s);
3.75 (3H, s).

【０６７０】[0670]

【実施例３６７】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
チルチオ) フェニル］カルバマート（化合物番号A1.8）融点：94−95℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.69-7.62
(1H, m); 7.54-7.47 (1H,m); 7.44-7.24 (6H, m); 6.60
(1H, br.s); 4.23 (2H, s); 3.77 (3H, s).Working Example 367 Methyl N- [4- (benzoxazol-2-ylmeth)
Tylthio) phenyl] carbamate (Compound No. A1.8) Melting point: 94-95 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.69-7.62
(1H, m); 7.54-7.47 (1H, m); 7.44-7.24 (6H, m); 6.60
(1H, br.s); 4.23 (2H, s); 3.77 (3H, s).

【０６７１】[0671]

【実施例３６８】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−３−メチルフェニル］カルバマート（化合物番
号C1.55 ）融点：125 −126 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H, b
r.d, J=7.3 Hz); 7.91 (1H, br.d, J=7.4 Hz); 7.55-7.
36 (2H, m); 7.22 (1H, br.s); 7.17-7.11 (1H,m); 6.8
6 (1H, d, J=8.8 Hz); 6.44 (1H, br.s); 5.46 (2H,
s); 3.76 (3H, s);2.35 (3H, s). Working Example 368 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -3-methylphenyl] carbamate (compound number
No. C1.55) Melting point: 125-126 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H, b
rd, J = 7.3 Hz); 7.91 (1H, br.d, J = 7.4 Hz); 7.55-7.
36 (2H, m); 7.22 (1H, br.s); 7.17-7.11 (1H, m); 6.8
6 (1H, d, J = 8.8 Hz); 6.44 (1H, br.s); 5.46 (2H,
s); 3.76 (3H, s); 2.35 (3H, s).

【０６７２】[0672]

【実施例３６９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−エチルフェニル］カルバマート（化合物番
号C2.4）融点：140 −141 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H, d
d, J=8.7 & 1.5 Hz); 7.90 (1H, dd, J=8.2 & 2.1 Hz);
7.51-7.40 (3H, m); 6.92-6.86 (2H, m); 6.21(1H, b
r.s); 5.47 (2H, s); 3.75 (3H, s); 2.58 (2H, q, J=
7.4 Hz); 1.21 (3H, t, J=7.4 Hz). Working Example 369 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-ethylphenyl] carbamate (compound number
No. C2.4) Melting point: 140-141 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H, d
d, J = 8.7 & 1.5 Hz); 7.90 (1H, dd, J = 8.2 & 2.1 Hz);
7.51-7.40 (3H, m); 6.92-6.86 (2H, m); 6.21 (1H, b
rs); 5.47 (2H, s); 3.75 (3H, s); 2.58 (2H, q, J =
7.41); 1.21 (3H, t, J = 7.4 Hz).

【０６７３】[0673]

【実施例３７０】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−イソプロピルフェニル］カルバマート（化
合物番号C3.32 ）融点：113 −114 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.0 Hz); 7.91 (1H,d, J=8.0 Hz); 7.54-7.37 (3
H, m); 6.98 (1H, d, J=2.9 Hz); 6.86 (1H, dd,J=8.6
& 2.8 Hz); 6.23 (1H, br.s); 5.47 (2H, s); 3.78 (3
H, s); 3.05 (1H,heptet, J=6.9 Hz); 1.22 (6H, d, J=
6.9 Hz). Working Example 370 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-isopropylphenyl] carbamate
Compound No. C3.32) Melting point: 113-114 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.0 Hz); 7.91 (1H, d, J = 8.0 Hz); 7.54-7.37 (3
H, m); 6.98 (1H, d, J = 2.9 Hz); 6.86 (1H, dd, J = 8.6
& 2.8 Hz); 6.23 (1H, br.s); 5.47 (2H, s); 3.78 (3
H, s); 3.05 (1H, heptet, J = 6.9 Hz); 1.22 (6H, d, J =
6.9 Hz).

【０６７４】[0674]

【実施例３７１】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−ｔ−ブチルフェニル］カルバマート（化合
物番号C4.29 ）融点：162 −164 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
４（１Ｈ，ｄ，Ｊ＝７．７Ｈｚ）；７．９１
（１Ｈ，ｄ，Ｊ＝８．１Ｈｚ）；７．５４−
７．３４（３Ｈ，ｍ）；７．１０−７．０９
（１Ｈ，ｍ）；６．８９−６．８４（１Ｈ，
ｍ）；６．２９（１Ｈ，ｂｒ．ｓ）；５．４６
（２Ｈ，ｓ）；３．７５（３Ｈ，ｓ）；１．
３８（９Ｈ，ｓ）． Working Example 371 Methyl N- [4- (benzothiazol-2-ylmethoate)
[Xy] -2-t-butylphenyl] carbamate (compound
Product No. C4.29) Melting point: 162-164 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
4. (1H, d, J = 7.7 Hz); 7.91
(1H, d, J = 8.1 Hz); 7.54-
7.34 (3H, m); 7.10-7.09
(1H, m); 6.89-6.84 (1H, m)
m); 6.29 (1H, br.s); 5.46
(2H, s); 3.75 (3H, s);
38 (9H, s).

【０６７５】[0675]

【実施例３７２】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−クロロフェニル］カルバマート（化合物番
号Ｃ９．３９）融点：173.5 −174.5 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H, b
r.d, J=7.8 Hz); 7.91 (1H, d, J=7.7 Hz); 7.66-7.31
(3H, m); 7.09 (1H, d, J=2.9 Hz); 6.98 (1H, dd, J=
9.1 & 2.9 Hz); 6.92 (1H, br.s); 5.45 (2H, s); 3.79
(3H, s). Working Example 372 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-chlorophenyl] carbamate (compound number
No. C9.39) melting point: 173.5-174.5 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H, b
rd, J = 7.8 Hz); 7.91 (1H, d, J = 7.7 Hz); 7.66-7.31
(3H, m); 7.09 (1H, d, J = 2.9 Hz); 6.98 (1H, dd, J =
9.1 & 2.9 Hz); 6.92 (1H, br.s); 5.45 (2H, s); 3.79
(3H, s).

【０６７６】[0676]

【実施例３７３】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−クロロフェニル］カルバマート（化合物
番号C9.40 ）融点：120 −122 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05-7.99
(1H, m); 7.79-7.74 (1H,m); 7.59-7.55 (1H, m); 7.40
-7.36 (2H, m); 7.11 (1H, d, J=2.9 Hz); 7.00(1H, d
d, J=8.9 & 2.8 Hz); 6.92 (1H, br.s); 5.29 (2H, s);
3.79 (3H, s). Working Example 373 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -2-chlorophenyl] carbamate (compound
No. C9.40) Melting point: 120-122 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05-7.99
(1H, m); 7.79-7.74 (1H, m); 7.59-7.55 (1H, m); 7.40
-7.36 (2H, m); 7.11 (1H, d, J = 2.9 Hz); 7.00 (1H, d
d, J = 8.9 & 2.8 Hz); 6.92 (1H, br.s); 5.29 (2H, s);
3.79 (3H, s).

【０６７７】[0677]

【実施例３７４】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−３−ニトロフェニル］カルバマート（化合物
番号C10.66）融点：113 −115 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.96 (1H,
d, J=2.7 Hz); 7.79-7.72(1H, m); 7.59-7.55 (2H, m);
7.43-7.33 (2H, m); 7.28-7.24 (1H, m); 6.80(1H, b
r.s); 5.43 (2H, s); 3.78 (3H, s).Working Example 374 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -3-nitrophenyl] carbamate (compound
No. C10.66) Melting point: 113-115 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.96 (1H,
d, J = 2.7 Hz); 7.79-7.72 (1H, m); 7.59-7.55 (2H, m);
7.43-7.33 (2H, m); 7.28-7.24 (1H, m); 6.80 (1H, b
rs); 5.43 (2H, s); 3.78 (3H, s).

【０６７８】[0678]

【実施例３７５】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２，３−ジメチルフェニル］カルバマート（化
合物番号C11.4 ）融点：178 −180 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H, d
d, J=8.1 & 1.4 Hz); 7.91 (1H, dd, J=7.4 & 1.4 Hz);
7.55-7.36 (2H, m); 7.29-7.26 (1H, br.m); 6.82 (1
H, d, J=8.8 Hz); 6.21 (1H, br.s); 5.46 (2H, s); 3.
76 (3H, s); 2.37(3H, s); 2.20 (3H, s). Working Example 375 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2,3-dimethylphenyl] carbamate
Compound No. C11.4) Melting point: 178-180 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H, d
d, J = 8.1 & 1.4 Hz); 7.91 (1H, dd, J = 7.4 & 1.4 Hz);
7.55-7.36 (2H, m); 7.29-7.26 (1H, br.m); 6.82 (1
H, d, J = 8.8 Hz); 6.21 (1H, br.s); 5.46 (2H, s); 3.
76 (3H, s); 2.37 (3H, s); 2.20 (3H, s).

【０６７９】[0679]

【実施例３７６】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２，５−ジメチルフェニル］カルバマート（化
合物番号C11.20）融点：127 −128 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H, d
d, J=8.7 & 1.6 Hz); 7.91 (1H, dd, J=7.3 & 1.4 Hz);
7.55-7.37 (3H, m); 6.73 (1H, s); 6.17 (1H,br.s);
5.45 (2H, s); 3.76 (3H, s); 2.33 (3H, s); 2.20 (3
H, s). Working Example 376: Methyl N- [4- (benzothiazol-2-ylmethoate)
[Xy) -2,5-dimethylphenyl] carbamate
Compound No. C11.20) Melting point: 127-128 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H, d
d, J = 8.7 & 1.6 Hz); 7.91 (1H, dd, J = 7.3 & 1.4 Hz);
7.55-7.37 (3H, m); 6.73 (1H, s); 6.17 (1H, br.s);
5.45 (2H, s); 3.76 (3H, s); 2.33 (3H, s); 2.20 (3
H, s).

【０６８０】[0680]

【実施例３７７】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２，３，６−トリメチルフェニル］カルバマー
ト（化合物番号C11.79）融点：177 −179 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.2 Hz); 7.91 (1H,d, J=8.1 Hz); 7.51-7.41 (2
H, m); 6.69 (1H, s); 5.95 (1H, br.s); 5.45 (2H,
s); 3.76 (3H, s); 2.28 (3H, s); 2.23 (3H, s); 2.21
(3H, s). Working Example 377 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2,3,6-trimethylphenyl] carbamer
(Compound No. C11.79) Melting point: 177-179 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.2 Hz); 7.91 (1H, d, J = 8.1 Hz); 7.51-7.41 (2
H, m); 6.69 (1H, s); 5.95 (1H, br.s); 5.45 (2H,
s); 3.76 (3H, s); 2.28 (3H, s); 2.23 (3H, s); 2.21
(3H, s).

【０６８１】[0681]

【実施例３７８】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−３，５−ジメトキシフェニル］カルバマート
（化合物番号C12.47）融点：110 −113 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
２−７．９０（２Ｈ，ｍ）；７．５２−７．３８
（２Ｈ，ｍ）；６．７０（２Ｈ，ｓ）；６．
６０（１Ｈ，ｂｒ．ｓ）；５．３７（２Ｈ，
ｓ）；３．８２（６Ｈ，ｓ）；３．７７（３
Ｈ，ｓ）． Working Example 378 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -3,5-dimethoxyphenyl] carbamate
(Compound No. C12.47) Melting point: 110-113 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
2-7.90 (2H, m); 7.52-7.38
(2H, m); 6.70 (2H, s);
60 (1H, br.s); 5.37 (2H, br.s)
3.82 (6H, s); 3.77 (3
H, s).

【０６８２】[0682]

【実施例３７９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−５−クロロ−２−メチルフェニル］カルバマー
ト（化合物番号Ｃ１６．１２６）融点：138 −141 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=6.9 Hz); 7.92 (1H,dd, J=8.1 & 2.2 Hz); 7.81
(1H, br.s); 7.55-7.37 (2H, m); 6.86 (1H, s);6.22
(1H, br.s); 5.51 (2H, s); 3.78 (3H, s); 2.20 (3H,
s). Working Example 379 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -5-chloro-2-methylphenyl] carbamer
(Compound No. C16.126) Melting point: 138-141 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 6.9 Hz); 7.92 (1H, dd, J = 8.1 & 2.2 Hz); 7.81
(1H, br.s); 7.55-7.37 (2H, m); 6.86 (1H, s); 6.22
(1H, br.s); 5.51 (2H, s); 3.78 (3H, s); 2.20 (3H,
s).

【０６８３】[0683]

【実施例３８０】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−５−イソプロピル−２−メチルフェニル］カル
バマート（化合物番号C18.119 ）融点：115 −117 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.7 Hz); 7.92 (1H,dd, J=8.4 & 2.1 Hz); 7.55-
7.37 (3H, m); 6.75 (1H, s); 6.22 (1H, br.s);5.46
(2H, s); 3.77 (3H, s); 3.43 (1H, quintet, J=7.0 H
z); 2.21 (3H, s);1.29 (6H, d, J=6.9 Hz). Working Example 380: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -5-isopropyl-2-methylphenyl] cal
Bamate (Compound No. C18.119) Melting point: 115-117 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.7 Hz); 7.92 (1H, dd, J = 8.4 & 2.1 Hz); 7.55-
7.37 (3H, m); 6.75 (1H, s); 6.22 (1H, br.s); 5.46
(2H, s); 3.77 (3H, s); 3.43 (1H, quintet, J = 7.0 H
z); 2.21 (3H, s); 1.29 (6H, d, J = 6.9 Hz).

【０６８４】[0684]

【実施例３８１】メチルＮ−｛４−［１−( ベンゾチアゾール−２−イ
ル）エトキシ］フェニル｝カルバマート（化合物番号E
1.3）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.00 (1H,
d, J=6.7 Hz); 7.86 (1H,d, J=7.7 Hz); 7.53-7.20 (4
H, m); 6.98-6.90 (2H, m); 6.42 (1H, br.s); 5.69 (1
H, q, J=6.6 Hz); 3.74 (3H, s); 1.83 (3H, d, J=6.5
Hz).Working Example 381 Methyl N- {4- [1- (benzothiazol-2-i)
Le) ethoxy] phenyl} carbamate (Compound No. E
1.3) Amorphous NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.00 (1H,
d, J = 6.7 Hz); 7.86 (1H, d, J = 7.7 Hz); 7.53-7.20 (4
H, m); 6.98-6.90 (2H, m); 6.42 (1H, br.s); 5.69 (1
H, q, J = 6.6 Hz); 3.74 (3H, s); 1.83 (3H, d, J = 6.5
Hz).

【０６８５】[0685]

【実施例３８２】メチルＮ−｛４−［１−( ベンゾチアゾール−２−イ
ル）エトキシ］−２−メチルフェニル｝カルバマート
（化合物番号E1.17 ）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04-7.89
(2H, m); 7.52-7.32 (3H,m); 6.87-6.79 (2H, m); 6.16
(1H, br.s); 5.70 (1H, q, J=6.6 Hz); 3.74 (3H, s);
2.19 (3H, s); 1.82 (3H, d, J=6.5 Hz).Working Example 382 Methyl N- {4- [1- (benzothiazol-2-i)
Ru) ethoxy] -2-methylphenyl} carbamate
(Compound No. E1.17) Amorphous NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.04-7.89
(2H, m); 7.52-7.32 (3H, m); 6.87-6.79 (2H, m); 6.16
(1H, br.s); 5.70 (1H, q, J = 6.6 Hz); 3.74 (3H, s);
2.19 (3H, s); 1.82 (3H, d, J = 6.5 Hz).

【０６８６】[0686]

【実施例３８３】メチルＮ−［４−（４−メチルベンゾオキサゾール−
２−イルメトキシ）フェニル］カルバマート（化合物番
号F1.5）融点：95−96℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.40-7.13
(5H, m); 7.05-6.99 (2H,m); 6.50-6.49 (1H, br.m);
5.29 (2H, s); 3.75 (3H, s); 2.63 (3H, s).Working Example 383 Methyl N- [4- (4-methylbenzoxazole-
2-ylmethoxy) phenyl] carbamate (compound number
No. F1.5) Melting point: 95-96 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.40-7.13
(5H, m); 7.05-6.99 (2H, m); 6.50-6.49 (1H, br.m);
5.29 (2H, s); 3.75 (3H, s); 2.63 (3H, s).

【０６８７】[0687]

【実施例３８４】メチルＮ−［４−（５−メチルベンゾオキサゾール−
２−イルメトキシ）フェニル］カルバマート（化合物番
号F1.15 ）融点：105 −108 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.53-7.52
(1H, m); 7.42 (1H, d, J=8.4 Hz); 7.32-7.26 (2H,
m); 7.20-7.15 (1H, m); 7.03-6.99 (2H, m); 6.50-6.4
5 (1H, br.m); 5.30 (2H, s); 3.76 (3H, s); 2.47 (3
H, s).Working Example 384 Methyl N- [4- (5-methylbenzoxazole-
2-ylmethoxy) phenyl] carbamate (compound number
No. F1.15) Melting point: 105-108 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.53-7.52
(1H, m); 7.42 (1H, d, J = 8.4 Hz); 7.32-7.26 (2H,
m); 7.20-7.15 (1H, m); 7.03-6.99 (2H, m); 6.50-6.4
5 (1H, br.m); 5.30 (2H, s); 3.76 (3H, s); 2.47 (3
H, s).

【０６８８】[0688]

【実施例３８５】メチルＮ−［４−（６−メチルベンゾオキサゾール−
２−イルメトキシ）フェニル］カルバマート（化合物番
号F1.25 ）融点：102 −104 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．６
１（１Ｈ，ｄ，Ｊ＝８．４Ｈｚ）；７．３５
−７．２６（３Ｈ，ｍ）；７．１９−７．１５
（１Ｈ，ｍ）；７．０１（２Ｈ，ｄｄ，Ｊ＝
６．８＆２．２Ｈｚ）；６．４８−６．４７
（１Ｈ，ｂｒ．ｍ）；５．２７（２Ｈ，ｓ）；
３．７６（３Ｈ，ｓ）；２．４９（３Ｈ，
ｓ）．Working Example 385 Methyl N- [4- (6-methylbenzoxazole-
2-ylmethoxy) phenyl] carbamate (compound number
No. F1.25) Melting point: 102-104 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.6
1 (1H, d, J = 8.4 Hz); 7.35
-7.26 (3H, m); 7.19-7.15
(1H, m); 7.01 (2H, dd, J =
6.8 & 2.2 Hz); 6.48-6.47
(1H, br.m); 5.27 (2H, s);
3.76 (3H, s); 2.49 (3H, s)
s).

【０６８９】[0689]

【実施例３８６】メチルＮ−［４−（７−メチルベンゾチアゾール−２
−イルメトキシ）フェニル］カルバマート（化合物番号
Ｆ１．３３）融点：150 −151 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.57 (1H,
d, J=7.7 Hz); 7.33-7.14(4H, m); 7.03 (2H, dd, J=6.
8 & 2.3 Hz); 6.50 (1H, br.s); 5.29 (2H, s);3.76 (3
H, s); 2.54 (3H, s).Working Example 386 Methyl N- [4- (7-methylbenzothiazole-2)
-Ylmethoxy) phenyl] carbamate (compound number
F1.33) Melting point: 150-151 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.57 (1H,
d, J = 7.7 Hz); 7.33-7.14 (4H, m); 7.03 (2H, dd, J = 6.
8 & 2.3 Hz); 6.50 (1H, br.s); 5.29 (2H, s); 3.76 (3
H, s); 2.54 (3H, s).

【０６９０】[0690]

【実施例３８７】メチルＮ−［４−（５−ニトロベンゾオキサゾール−
２−イルメトキシ）フェニル］カルバマート（化合物番
号F1.69 ）融点：184 −187 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.66 (1H,
d, J=2.2 Hz); 8.36 (1H,dd, J=9.0 & 2.3 Hz); 7.68
(1H, d, J=9.3 Hz); 7.35-7.26 (2H, m); 7.03-6.99 (2
H, m); 6.51-5.48 (1H, br.m); 5.34 (2H, s); 3.76 (3
H, s).Working Example 387 Methyl N- [4- (5-nitrobenzoxazole-
2-ylmethoxy) phenyl] carbamate (compound number
No. F1.69) Melting point: 184-187 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.66 (1H,
d, J = 2.2 Hz); 8.36 (1H, dd, J = 9.0 & 2.3 Hz); 7.68
(1H, d, J = 9.3 Hz); 7.35-7.26 (2H, m); 7.03-6.99 (2
H, m); 6.51-5.48 (1H, br.m); 5.34 (2H, s); 3.76 (3
H, s).

【０６９１】[0691]

【実施例３８８】メチルＮ−［４−（５−メトキシベンゾオキサゾール
−２−イルメトキシ）フェニル］カルバマート（化合物
番号F3.14 ）融点：134 −137 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.43 (1H,
d, J=8.7 Hz); 7.32-7.22(3H, m); 7.03-6.94 (1H, br.
m); 6.49-6.30 (1H, br.m); 5.27 (2H, s); 3.86(3H,
s); 3.76 (3H, s).Working Example 388 Methyl N- [4- (5-methoxybenzoxazole)
-2-ylmethoxy) phenyl] carbamate (compound
No. F3.14) melting point: 134-137 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.43 (1H,
d, J = 8.7 Hz); 7.32-7.22 (3H, m); 7.03-6.94 (1H, br.
m); 6.49-6.30 (1H, br.m); 5.27 (2H, s); 3.86 (3H,
s); 3.76 (3H, s).

【０６９２】[0692]

【実施例３８９】メチルＮ−［４−（５−クロロベンゾオキサゾール−
２−イルメトキシ）フェニル］カルバマート（化合物番
号F4.63 ）融点：157 −160 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.74 (1H,
d, J=2.3 Hz); 7.48 (1H,d, J=8.8 Hz); 7.38-7.26 (3
H, m); 7.00 (2H, dd, J=6.9 &.2 Hz); 6.48 (1H,br.
s); 5.29 (2H, s); 3.76 (3H, s).Working Example 389 Methyl N- [4- (5-chlorobenzoxazole-
2-ylmethoxy) phenyl] carbamate (compound number
No. F4.63) melting point: 157-160 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.74 (1H,
d, J = 2.3 Hz); 7.48 (1H, d, J = 8.8 Hz); 7.38-7.26 (3
H, m); 7.00 (2H, dd, J = 6.9 & .2 Hz); 6.48 (1H, br.
s); 5.29 (2H, s); 3.76 (3H, s).

【０６９３】[0693]

【実施例３９０】メチルＮ−［４−（５−トリフルオロメチルベンゾオ
キサゾール−２−イルメトキシ）フェニル］カルバマー
ト（化合物番号F5.13 ）融点：145 −148 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
s); 7.67 (2H, d, J=1.2Hz); 7.34-7.28 (2H, m); 7.01
(2H, dd, J=6.9 & 1.3 Hz); 6.47 (1H, br.s);5.33 (2
H, s); 3.76 (3H, s).Working Example 390 Methyl N- [4- (5-trifluoromethylbenzoic acid)
Xazol-2-ylmethoxy) phenyl] carbamer
(Compound No. F5.13) Melting point: 145-148 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
s); 7.67 (2H, d, J = 1.2Hz); 7.34-7.28 (2H, m); 7.01
(2H, dd, J = 6.9 & 1.3 Hz); 6.47 (1H, br.s); 5.33 (2
H, s); 3.76 (3H, s).

【０６９４】[0694]

【実施例３９１】メチルＮ−［４−（５，７−ジメチルベンゾオキサゾ
ール−２−イルメトキシ）フェニル］カルバマート（化
合物番号F7.17 ）融点：157 −159 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.34-7.26
(3H, m); 7.04-6.98 (3H,m); 6.49 (1H, br.s); 5.26
(2H, s); 3.76 (3H, s); 2.48 (3H, s); 2.43 (3H, s). Working Example 391 Methyl N- [4- (5,7-dimethylbenzoxazo
2-ylmethoxy) phenyl] carbamate
Compound No. F7.17) Melting point: 157-159 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.34-7.26
(3H, m); 7.04-6.98 (3H, m); 6.49 (1H, br.s); 5.26
(2H, s); 3.76 (3H, s); 2.48 (3H, s); 2.43 (3H, s).

【０６９５】[0696]

【実施例３９２】メチルＮ−［４−（６，７−ジフルオロベンゾオキサ
ゾール−２−イルメトキシ）フェニル］カルバマート
（化合物番号F7.56 ）融点：145 −148 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：７．５
１−７．４２（１Ｈ，ｍ）；７．３４−７．２８
（２Ｈ，ｍ）；７．２４−７．１４（１Ｈ，
ｍ）；７．０１（２Ｈ，ｄｄ，Ｊ＝６．８＆
２．３Ｈｚ）；６．４９−６．４８（１Ｈ，
ｂｒ．ｍ）；５．２９（２Ｈ，ｓ）；３．７８
（３Ｈ，ｓ）．Working Example 392 Methyl N- [4- (6,7-difluorobenzoxa)
Sol-2-ylmethoxy) phenyl] carbamate
(Compound No. F7.56) Melting point: 145-148 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.5
1-7.42 (1H, m); 7.34-7.28
(2H, m); 7.24-7.14 (1H,
m); 7.01 (2H, dd, J = 6.8 &
2.3 Hz); 6.49-6.48 (1H,
br. m); 5.29 (2H, s); 3.78
(3H, s).

【０６９６】[0696]

【実施例３９３】メチルＮ−［４−（５，７−ジクロロベンゾオキサゾ
ール−２−イルメトキシ）フェニル］カルバマート（化
合物番号Ｆ７．６９）融点：135 −136 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.65 (1H,
d, J=1.8 Hz); 7.40 (1H,d, J=1.9 Hz); 7.34-7.26 (2
H, m); 7.10 (2H, dd, J=6.8 & 2.3 Hz); 6.50-6.49 (1
H, br.m); 5.30 (2H, s); 3.76 (3H, s). Working Example 393 Methyl N- [4- (5,7-dichlorobenzoxazo
2-ylmethoxy) phenyl] carbamate
Compound No. F7.69) Melting point: 135-136 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.65 (1H,
d, J = 1.8 Hz); 7.40 (1H, d, J = 1.9 Hz); 7.34-7.26 (2
H, m); 7.10 (2H, dd, J = 6.8 & 2.3 Hz); 6.50-6.49 (1
H, br.m); 5.30 (2H, s); 3.76 (3H, s).

【０６９７】[0697]

【実施例３９４】メチルＮ−［２−メチル−４−（４−メチルベンゾオ
キサゾール−２−イルメトキシ）フェニル］カルバマー
ト（化合物番号G1.5）融点：149 −151 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.60-7.45
(1H, br.m); 7.40-7.36 (1H, m); 7.29-7.22 (1H, m);
7.17-7.14 (1H, m); 6.93-6.89 (2H, m); 6.21-6.18 (1
H, br.m); 5.29 (2H, s); 3.76 (3H, s); 2.63 (3H,
s); 2.23 (3H, s). Working Example 394 Methyl N- [2-methyl-4- (4-methylbenzoic)
Xazol-2-ylmethoxy) phenyl] carbamer
(Compound No. G1.5) Melting point: 149-151 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.60-7.45
(1H, br.m); 7.40-7.36 (1H, m); 7.29-7.22 (1H, m);
7.17-7.14 (1H, m); 6.93-6.89 (2H, m); 6.21-6.18 (1
H, br.m); 5.29 (2H, s); 3.76 (3H, s); 2.63 (3H,
s); 2.23 (3H, s).

【０６９８】[0698]

【実施例３９５】メチルＮ−［２−メチル−４−（５−メチルベンゾオ
キサゾール−２−イルメトキシ）フェニル］カルバマー
ト（化合物番号G1.10 ）融点：164 −166 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.56-7.49
(1H, br.m); 7.53 (1H, d, J=0.8 Hz); 7.42 (1H, d, J
=8.4 Hz); 7.19-7.15 (1H, m); 6.92-6.87 (2H, m); 6.
20-6.18 (1H, br.m); 5.26 (2H, s); 3.76 (3H, s); 2.
47 (3H, s); 2.23(3H, s). Working Example 395 Methyl N- [2-methyl-4- (5-methylbenzoic)
Xazol-2-ylmethoxy) phenyl] carbamer
Doo (Compound No. G1.10) mp: 164 -166 ° C. NMR spectrum _{(200MHz, CDCl 3), δppm} : 7.56-7.49
(1H, br.m); 7.53 (1H, d, J = 0.8 Hz); 7.42 (1H, d, J
= 8.4 Hz); 7.19-7.15 (1H, m); 6.92-6.87 (2H, m); 6.
20-6.18 (1H, br.m); 5.26 (2H, s); 3.76 (3H, s); 2.
47 (3H, s); 2.23 (3H, s).

【０６９９】[0699]

【実施例３９６】メチルＮ−［２−メチル−４−（６−メチルベンゾオ
キサゾール−２−イルメトキシ）フェニル］カルバマー
ト（化合物番号G1.15 ）融点：139 −142 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.61 (1H,
d, J=8.2 Hz); 7.54-7.51(1H, br.m); 7.35 (1H, d, J=
0.7 Hz); 7.17 (1H, dd, J=8.0 & 1.3 Hz); 6.92-6.86
(3H, m); 6.21-6.18 (1H, br.m); 5.26 (2H, s); 3.76
(3H, s); 2.49 (3H, s); 2.23 (3H, s). Working Example 396 Methyl N- [2-methyl-4- (6-methylbenzoic)
Xazol-2-ylmethoxy) phenyl] carbamer
(Compound No. G1.15) Melting point: 139-142 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.61 (1H,
d, J = 8.2 Hz); 7.54-7.51 (1H, br.m); 7.35 (1H, d, J =
0.717); 7.17 (1H, dd, J = 8.0 & 1.3 Hz); 6.92-6.86
(3H, m); 6.21-6.18 (1H, br.m); 5.26 (2H, s); 3.76
(3H, s); 2.49 (3H, s); 2.23 (3H, s).

【０７００】[0700]

【実施例３９７】メチルＮ−［２−メチル−４−（７−メチルベンゾオ
キサゾール−２−イルメトキシ）フェニル］カルバマー
ト（化合物番号G1.20 ）融点：157 −159 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.59-7.53
(2H, m); 7.29-7.14 (2H,m); 6.94-6.89 (2H, m); 6.19
(1H, br.s); 5.29 (2H, s); 3.76 (3H, s); 2.54 (3H,
s); 2.24 (3H, s). Working Example 397 Methyl N- [2-methyl-4- (7-methylbenzoic acid)
Xazol-2-ylmethoxy) phenyl] carbamer
(Compound No. G1.20) Melting point: 157-159 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.59-7.53
(2H, m); 7.29-7.14 (2H, m); 6.94-6.89 (2H, m); 6.19
(1H, br.s); 5.29 (2H, s); 3.76 (3H, s); 2.54 (3H,
s); 2.24 (3H, s).

【０７０１】[0701]

【実施例３９８】メチルＮ−［４−（５−フルオロベンゾオキサゾール
−２−イルメトキシ）−２−メチルフェニル］カルバマ
ート（化合物番号G1.59 ）融点：182 −184 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.59-7.49
(1H, br.m); 7.53-7.41 (2H, m); 7.11 (1H, td, J=9.1
& 2.6 Hz); 6.89-6.87 (2H, m); 6.21 (1H, br.s); 5.
28 (2H, s); 3.76 (3H, s); 2.24 (3H, s).Working Example 398 Methyl N- [4- (5-fluorobenzoxazole)
-2-ylmethoxy) -2-methylphenyl] carbama
Melting point: 182-184 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.59-7.49
(1H, br.m); 7.53-7.41 (2H, m); 7.11 (1H, td, J = 9.1
& 2.6 Hz); 6.89-6.87 (2H, m); 6.21 (1H, br.s); 5.
28 (2H, s); 3.76 (3H, s); 2.24 (3H, s).

【０７０２】[0702]

【実施例３９９】メチルＮ−［４−（６−フルオロベンゾオキサゾール
−２−イルメトキシ）−２−メチルフェニル］カルバマ
ート（化合物番号G1.64 ）融点：138 −140 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.68 (1H, d
d, J=8.8 & 5.0 Hz); 7.59-7.50 (1H, br.m); 7.31-7.2
6 (1H, m); 7.11 (1H, td, J=9.2 & 2.5 Hz); 6.91-6.8
7 (2H, m); 6.23-6.19 (1H, br.m); 5.27 (2H, s); 3.7
6 (3H, s); 2.23(3H, s).Working Example 399 Methyl N- [4- (6-fluorobenzoxazole)
-2-ylmethoxy) -2-methylphenyl] carbama
(Compound No. G1.64) Melting point: 138-140 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.68 (1H, d
d, J = 8.8 & 5.0 Hz); 7.59-7.50 (1H, br.m); 7.31-7.2
6 (1H, m); 7.11 (1H, td, J = 9.2 & 2.5 Hz); 6.91-6.8
7 (2H, m); 6.23-6.19 (1H, br.m); 5.27 (2H, s); 3.7
6 (3H, s); 2.23 (3H, s).

【０７０３】[0703]

【実施例４００】メチルＮ−［４−（７−フルオロベンゾオキサゾール
−２−イルメトキシ）−２−メチルフェニル］カルバマ
ート（化合物番号G1.69 ）融点：138 −141 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.58-7.53
(2H, m); 7.35-7.25 (1H,m); 6.93-6.88 (2H, m); 6.21
-6.20 (1H, br.m); 5.31 (2H, s); 3.76 (3H, s); 2.24
(3H, s).Working Example 400 Methyl N- [4- (7-fluorobenzoxazole)
-2-ylmethoxy) -2-methylphenyl] carbama
(Compound No. G1.69) Melting point: 138-141 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.58-7.53
(2H, m); 7.35-7.25 (1H, m); 6.93-6.88 (2H, m); 6.21
-6.20 (1H, br.m); 5.31 (2H, s); 3.76 (3H, s); 2.24
(3H, s).

【０７０４】[0704]

【実施例４０１】メチルＮ−［４−（５−クロロベンゾオキサゾール−
２−イルメトキシ）−２−メチルフェニル］カルバマー
ト（化合物番号G1.77 ）融点：156 −158 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.74 (1H,
d, J=2.1 Hz); 7.58-7.50(1H, br.m); 7.48 (1H, d, J=
8.8 Hz); 7.35 (1H, dd, J=8.7 & 2.0 Hz); 6.89-6.87
(2H, m); 6.21 (1H, br.s); 5.28 (2H, s); 3.76 (3H,
s); 2.23 (3H, s).Working Example 401 Methyl N- [4- (5-chlorobenzoxazole-
2-ylmethoxy) -2-methylphenyl] carbamer
(Compound No. G1.77) Melting point: 156-158 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.74 (1H,
d, J = 2.1 Hz); 7.58-7.50 (1H, br.m); 7.48 (1H, d, J =
8.8 Hz); 7.35 (1H, dd, J = 8.7 & 2.0 Hz); 6.89-6.87
(2H, m); 6.21 (1H, br.s); 5.28 (2H, s); 3.76 (3H,
s); 2.23 (3H, s).

【０７０５】[0705]

【実施例４０２】メチルＮ−［２−メチル−４−（５−トリフルオロメ
チルベンゾオキサゾール−２−イルメトキシ）フェニ
ル］カルバマート（化合物番号G1.96 ）融点：141 −143 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
s); 7.67 (2H, d, J=1.1Hz); 7.60-7.50 (2H, br.m);
6.91-6.87 (2H, m);H, s); 2.24 (3H, s).Working Example 402 Methyl N- [2-methyl-4- (5-trifluoromethod)
Tylbenzoxazol-2-ylmethoxy) phenyi
] Carbamate (compound number G1.96) melting point: 141-143 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
s); 7.67 (2H, d, J = 1.1Hz); 7.60-7.50 (2H, br.m);
6.91-6.87 (2H, m); H, s); 2.24 (3H, s).

【０７０６】[0706]

【実施例４０３】メチルＮ−［４−（５，７−ジメチルベンゾオキサゾ
ール−２−イルメトキシ）−２−メチルフェニル］カル
バマート（化合物番号G2.14 ）融点：154 −155 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.58-7.50
(1H, br.m); 7.35 (1H, s); 6.98 (1H, s); 6.91-6.89
(2H, m); 6.20 (1H, br.s); 5.26 (2H, s); 3.76(3H,
s); 2.48 (3H, s); 2.43 (3H, s); 2.23 (3H, s). Working Example 403: Methyl N- [4- (5,7-dimethylbenzoxazo
2-ylmethoxy) -2-methylphenyl] cal
Bamate (Compound No. G2.14) Melting point: 154-155 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.58-7.50
(1H, br.m); 7.35 (1H, s); 6.98 (1H, s); 6.91-6.89
(2H, m); 6.20 (1H, br.s); 5.26 (2H, s); 3.76 (3H,
s); 2.48 (3H, s); 2.43 (3H, s); 2.23 (3H, s).

【０７０７】[0707]

【実施例４０４】メチルＮ−［４−（６，７−ジフルオロベンゾオキサ
ゾール−２−イルメトキシ）−２−メチルフェニル］カ
ルバマート（化合物番号G2.50 ）融点：124 −125 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.59-7.43
(2H, m); 7.24-7.14 (1H,m); 6.92-6.87 (2H, m); 6.20
-6.19 (1H, br.m); 5.29 (2H, s); 3.76 (3H, s); 2.24
(3H, s). Working Example 404 Methyl N- [4- (6,7-difluorobenzoxa)
Zol-2-ylmethoxy) -2-methylphenyl] ca
Rubamate (Compound No. G2.50) Melting point: 124-125 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.59-7.43
(2H, m); 7.24-7.14 (1H, m); 6.92-6.87 (2H, m); 6.20
-6.19 (1H, br.m); 5.29 (2H, s); 3.76 (3H, s); 2.24
(3H, s).

【０７０８】[0708]

【実施例４０５】メチルＮ−［４−（５，７−ジクロロベンゾオキサゾ
ール−２−イルメトキシ）−２−メチルフェニル］カル
バマート（化合物番号G2.62 ）融点：130 −132 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.65 (1H,
d, J=1.9 Hz); 7.59-7.50(1H, br.m); 7.40 (1H, d, J=
1.9 Hz); 6.91-6.90 (1H, br.m); 5.29 (2H, s);3.76
(3H, s); 2.24 (3H, s). Working Example 405: Methyl N- [4- (5,7-dichlorobenzoxazo
2-ylmethoxy) -2-methylphenyl] cal
Bamate (Compound No. G2.62) Melting point: 130-132 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.65 (1H,
d, J = 1.9 Hz); 7.59-7.50 (1H, br.m); 7.40 (1H, d, J =
1.9 Hz); 6.91-6.90 (1H, br.m); 5.29 (2H, s); 3.76
(3H, s); 2.24 (3H, s).

【０７０９】[0709]

【実施例４０６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−（２−ヒドロキシエチル）
アセトアミド（化合物番号D1.105）融点：97−99℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-8.03
(1H, m); 7.93-7.89 (1H,m); 7.56-7.38 (2H, m); 7.11
(1H, d, J=8.6 Hz); 6.98 (1H, d, J=2.6 Hz);6.91 (1
H, dd, J=8.6 & 2.8 Hz); 5.49 (2H, s); 4.28-4.10 (1
H, m); 3.82-3.74 (2H, m); 3.38-3.27 (2H, m); 2.24
(3H, s); 1.79 (3H, s). Working Example 406 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- (2-hydroxyethyl)
Acetamide (Compound No. D1.105) Melting point: 97-99 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-8.03
(1H, m); 7.93-7.89 (1H, m); 7.56-7.38 (2H, m); 7.11
(1H, d, J = 8.6 Hz); 6.98 (1H, d, J = 2.6 Hz); 6.91 (1
H, dd, J = 8.6 & 2.8 Hz); 5.49 (2H, s); 4.28-4.10 (1
H, m); 3.82-3.74 (2H, m); 3.38-3.27 (2H, m); 2.24
(3H, s); 1.79 (3H, s).

【０７１０】[0710]

【実施例４０７】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−ヒドロキシメチ
ルカルバマート（化合物番号D1.49 ）融点：132 −133 ℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.74
(1H, m); 7.59-7.54 (1H,m); 7.43-7.32 (2H, m); 7.14
(1H, d, J=8.3 Hz); 6.96-6.86 (2H, m); 5.31(2H,
s); 5.15 (1H, dd, J=10.5 & 7.4 Hz); 4.78 (1H, dd,
J=10.4 & 8.5 Hz);3.67 (3H, br.s); 3.42 (1H, t, J=
7.9 Hz); 2.21 (3H, s). Working Example 407 Methyl N- [4- (benzoxazol-2-ylmethine)
Toxy) -2-methylphenyl] -N-hydroxymethyl
Lecarbamate (Compound No. D1.49) Melting point: 132-133 ° C NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.74
(1H, m); 7.59-7.54 (1H, m); 7.43-7.32 (2H, m); 7.14
(1H, d, J = 8.3 Hz); 6.96-6.86 (2H, m); 5.31 (2H,
s); 5.15 (1H, dd, J = 10.5 & 7.4 Hz); 4.78 (1H, dd,
J = 10.4 & 8.5 Hz); 3.67 (3H, br.s); 3.42 (1H, t, J =
7.9 Hz); 2.21 (3H, s).

【０７１１】[0711]

【実施例４０８】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−メトキシメチルカ
ルバマート（化合物番号D1.51 ）融点：76−78℃ ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.88
(2H, m); 7.55-7.37 (2H,m); 7.10 (1H, d, J=9.0 Hz);
6.93 (1H, d, J=2.6 Hz); 6.87 (1H, dd, J=8.6& 3.0
Hz); 5.47 (2H, s); 5.20-5.15 (1H, m); 4.64 (1H, d,
J=10.0 Hz); 2.20 (3H, s); 3.81-3.65 (3H, m); 3.44
(3H, s); 2.19 (3H, s). Working Example 408: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-methoxymethylca
Rubamate (Compound No. D1.51) Melting point: 76-78 ° C. NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-7.88
(2H, m); 7.55-7.37 (2H, m); 7.10 (1H, d, J = 9.0 Hz);
6.93 (1H, d, J = 2.6 Hz); 6.87 (1H, dd, J = 8.6 & 3.0
Hz); 5.47 (2H, s); 5.20-5.15 (1H, m); 4.64 (1H, d,
J = 10.0 Hz); 2.20 (3H, s); 3.81-3.65 (3H, m); 3.44
(3H, s); 2.19 (3H, s).

【０７１２】[0712]

【実施例４０９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−エトキシメチルカ
ルバマート（化合物番号D1.55 ）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
４（１Ｈ，ｄ，Ｊ＝８．８Ｈｚ）；７．９２
（１Ｈ，ｄ，Ｊ＝７．６Ｈｚ）；７．５６−７．
３５（２Ｈ，ｍ）；７．０９（１Ｈ，ｂｒ．
ｄ，Ｊ＝８．４Ｈｚ）；６．９５−６．８２
（２Ｈ，ｍ）；５．４７（２Ｈ，ｓ）；５．
２２（１Ｈ，ｂｒ．ｄ，Ｊ＝９．９Ｈｚ）；
４．７０（１Ｈ，ｄ，Ｊ＝１０．４Ｈｚ）；
３．８８−３．５０（５Ｈ，ｂｒ．ｓ）；２．１
９（３Ｈ，ｓ）；１．２１（３Ｈ，ｔ，Ｊ
＝７．０Ｈｚ）． Working Example 409 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-ethoxymethylca
Rubamate (Compound No. D1.55) amorphous NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
4. (1H, d, J = 8.8 Hz); 7.92
(1H, d, J = 7.6 Hz); 7.56-7.
35 (2H, m); 7.09 (1H, br.
d, J = 8.4 Hz); 6.95-6.82
(2H, m); 5.47 (2H, s);
22 (1H, br.d, J = 9.9 Hz);
4.70 (1H, d, J = 10.4 Hz);
3.88-3.50 (5H, br.s); 2.1
9 (3H, s); 1.21 (3H, t, J
= 7.0 Hz).

【０７１３】[0713]

【実施例４１０】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−イソブチルオキシ
メチルカルバマート（化合物番号Ｄ１．５６）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.89
(2H, m); 7.55-7.37 (2H,m); 7.10 (1H, d, J=8.6 Hz);
6.93 (1H, d, J=3.0 Hz); 6.86 (1H, dd, J=8.4& 3.0
Hz); 5.47 (2H, s); 4.96 (2H, AB q, J=10.2Hz, Dn=10
8.5）; 3.85-3.65 (3H, m); 3.41-3.30 (2H, m); 2.05
(3H, s); 1.92-1.80 (1H, m); 0.91 (6H,d, J=6.6 Hz). Working Example 410 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-isobutyloxy
Methyl carbamate (Compound No. D1.56) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-7.89
(2H, m); 7.55-7.37 (2H, m); 7.10 (1H, d, J = 8.6 Hz);
6.93 (1H, d, J = 3.0 Hz); 6.86 (1H, dd, J = 8.4 & 3.0
Hz); 5.47 (2H, s); 4.96 (2H, AB q, J = 10.2Hz, Dn = 10
8.5); 3.85-3.65 (3H, m); 3.41-3.30 (2H, m); 2.05
(3H, s); 1.92-1.80 (1H, m); 0.91 (6H, d, J = 6.6 Hz).

【０７１４】[0714]

【実施例４１１】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−ブテニルオ
キシメチル）カルバマート（化合物番号D1.60 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.0 Hz); 7.91 (1H,d, J=7.2 Hz); 7.55-7.37 (2
H, m); 7.10 (1H, br.d, J=8.7 Hz); 6.95-6.82 (2H,
m); 5.85-5.42 (2H, m); 5.47 (2H, s); 5.30-5.05 (1
H, m); 4.70 (1H, d,J=10.4 Hz); 4.15-3.95 (2H, m);
3.82-3.66 (3H, m); 2.18 (3H, s); 1.75-1.65 (3H,
m). Working Example 411 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-butenylo
Xymethyl) carbamate (Compound No. D1.60) oil NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.03 (1H,
d, J = 8.0 Hz); 7.91 (1H, d, J = 7.2 Hz); 7.55-7.37 (2
H, m); 7.10 (1H, br.d, J = 8.7 Hz); 6.95-6.82 (2H,
m); 5.85-5.42 (2H, m); 5.47 (2H, s); 5.30-5.05 (1
H, m); 4.70 (1H, d, J = 10.4 Hz); 4.15-3.95 (2H, m);
3.82-3.66 (3H, m); 2.18 (3H, s); 1.75-1.65 (3H,
m).

【０７１５】[0715]

【実施例４１２】メチルＮ−アセトキシメチル−Ｎ−［４−（ベンゾチ
アゾール−２−イルメトキシ）−２−メチルフェニル］
カルバマート（化合物番号D1.68 ）油状物ＮＭＲスペクトル(200Mz,CDCl₃),δppm: 8.04 (1H, dd,
J=7.2 & 1.3 Hz); 7.91(1H, dd, J=7.2 & 1.3 Hz); 7.
51 (1H, td, J=7.2 & 1.3 Hz); 7.43 (1H, td,J=7.2 &
1.3 Hz); 7.09 (1H, d, J=8.7 Hz); 6.93 (1H, d, J=3.
0 Hz); 6.86 (1H, dd, J=8.7 & 3.0 Hz); 5.71 (1H, d,
J=10.0 Hz); 5.47 (2H, s); 5.38 (1H,d, J=10.3 Hz);
3.83-3.69 (3H, m); 2.20 (3H, s); 2.06 (3H, s). Working Example 412 Methyl N-acetoxymethyl-N- [4- (benzothi
Azol-2-ylmethoxy) -2-methylphenyl]
Carbamate (Compound No. D1.68) oil NMR spectrum (200 Mz, CDCl ₃ ), δ ppm: 8.04 (1H, dd,
J = 7.2 & 1.3 Hz); 7.91 (1H, dd, J = 7.2 & 1.3 Hz); 7.91
51 (1H, td, J = 7.2 & 1.3 Hz); 7.43 (1H, td, J = 7.2 &
1.309); 7.09 (1H, d, J = 8.7 Hz); 6.93 (1H, d, J = 3.
0 Hz); 6.86 (1H, dd, J = 8.7 & 3.0 Hz); 5.71 (1H, d,
J = 10.0 Hz); 5.47 (2H, s); 5.38 (1H, d, J = 10.3 Hz);
3.83-3.69 (3H, m); 2.20 (3H, s); 2.06 (3H, s).

【０７１６】[0716]

【実施例４１３】メチルＮ−アセトキシメチル−Ｎ−［４−（ベンゾオ
キサゾール−２−イルメトキシ）−２−メチルフェニ
ル］カルバマート（化合物番号D1.69 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.80-7.75
(1H, m); 7.60-7.55 (1H,m); 7.43-7.36 (2H, m); 7.12
-7.07 (1H, m); 6.96-6.87 (2H, m); 5.71 (1H,d, J=1
0.9 Hz); 5.41-5.35 (1H, m); 5.31 (2H, s); 3.69 (3
H, s); 2.20 (3H,s); 2.06 (3H, s). Working Example 413 Methyl N-acetoxymethyl-N- [4- (benzoo
Xazol-2-ylmethoxy) -2-methylpheni
Le] carbamate (Compound No. D1.69) oil NMR spectrum _{(200MHz, CDCl 3), δppm} : 7.80-7.75
(1H, m); 7.60-7.55 (1H, m); 7.43-7.36 (2H, m); 7.12
-7.07 (1H, m); 6.96-6.87 (2H, m); 5.71 (1H, d, J = 1
0.941); 5.41-5.35 (1H, m); 5.31 (2H, s); 3.69 (3
H, s); 2.20 (3H, s); 2.06 (3H, s).

【０７１７】[0717]

【実施例４１４】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−プロピオニルオ
キシメチルカルバマート（化合物番号D1.71 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H,m); 7.43-7.35 (2H, m); 7.09
(1H, br.d, J=8.7 Hz); 6.95-6.86 (2H, m); 5.71 (1
H, d , J=10.3 Hz); 5.40 (1H, d, J=9.9 Hz); 5.31 (2
H, s); 3.68 (3H,br.s); 2.34 (2H, q, J=7.5 Hz); 2.2
0 (3H, s); 1.10 (3H, t, J=7.5 Hz). Working Example 414: Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -2-methylphenyl] -N-propionylo
Xymethyl carbamate (Compound No. D1.71) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H, m); 7.43-7.35 (2H, m); 7.09
(1H, br.d, J = 8.7 Hz); 6.95-6.86 (2H, m); 5.71 (1
H, d, J = 10.3 Hz); 5.40 (1H, d, J = 9.9 Hz); 5.31 (2
H, s); 3.68 (3H, br.s); 2.34 (2H, q, J = 7.5 Hz); 2.2
0 (3H, s); 1.10 (3H, t, J = 7.5 Hz).

【０７１８】[0718]

【実施例４１５】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−ブチリルオキシメ
チルカルバマート（化合物番号D1.72 ）油状物ＮＭＲスペクトル(200Mz,CDCl₃),δppm: 8.04 (1H, dd,
J=7.9 & 1.0 Hz); 7.91(1H, dd, J=7.9 & 1.0 Hz); 7.
51 (1H, td, J=7.9 & 1.0 Hz); 7.41 (1H, td,J=7.9 &
1.0 Hz); 7.09 (1H, d, J=8.3 Hz); 6.93 (1H, d, J=3.
0 Hz); 6.86 (1H, dd, J=8.3 & 3.0 Hz); 5.72 (1H, d,
J=10.3 Hz); 5.47 (2H, s); 5.40 (1H,d, J=10.3 Hz);
3.78-3.69 (3H, m); 2.28 (2H, t, J=7.3 Hz); 2.21
(3H, s);1.73-1.54 (2H, m); 0.91 (3H, t, J=7.3 Hz). Working Example 415 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-butyryloxime
Tilcarbamate (Compound No. D1.72) oil NMR spectrum (200 Mz, CDCl ₃ ), δ ppm: 8.04 (1H, dd,
J = 7.9 & 1.0 Hz); 7.91 (1H, dd, J = 7.9 & 1.0 Hz); 7.91
51 (1H, td, J = 7.9 & 1.0 Hz); 7.41 (1H, td, J = 7.9 &
1.009); 7.09 (1H, d, J = 8.3 Hz); 6.93 (1H, d, J = 3.
0 Hz); 6.86 (1H, dd, J = 8.3 & 3.0 Hz); 5.72 (1H, d,
J = 10.3 Hz); 5.47 (2H, s); 5.40 (1H, d, J = 10.3 Hz);
3.78-3.69 (3H, m); 2.28 (2H, t, J = 7.3 Hz); 2.21
(3H, s); 1.73-1.54 (2H, m); 0.91 (3H, t, J = 7.3 Hz).

【０７１９】[0719]

【実施例４１６】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−イソブチリルオキ
シメチルカルバマート（化合物番号D1.74 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.89
(2H, m); 7.56-7.37 (2H,m); 7.09 (1H, d, J=8.6 Hz);
6.93 (1H, d, J=2.8 Hz); 6.86 (1H, dd, J=8.8& 3.2
Hz); 5.55 (2H, AB q, J=10.2 Hz, Dn=63.0）; 5.47 (2
H, s); 3.90-3.65 (3H, m); 2.61-2.49 (1H, m); 2.21
(3H, s); 1.38 (3H, d, J=7.0 Hz). Working Example 416 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-isobutyryloxy
Cimethyl carbamate (Compound No. D1.74) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.89
(2H, m); 7.56-7.37 (2H, m); 7.09 (1H, d, J = 8.6 Hz);
6.93 (1H, d, J = 2.8 Hz); 6.86 (1H, dd, J = 8.8 & 3.2
Hz); 5.55 (2H, AB q, J = 10.2 Hz, Dn = 63.0); 5.47 (2
H, s); 3.90-3.65 (3H, m); 2.61-2.49 (1H, m); 2.21
(3H, s); 1.38 (3H, d, J = 7.0 Hz).

【０７２０】[0720]

【実施例４１７】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−ペンタノイルオキ
シメチルカルバマート（化合物番号D1.76 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H, J
=8.1 Hz); 7.92 (1H, d,J=7.6 Hz); 7.55-7.41 (2H,
m); 7.09 (1H, d, J=8.5 Hz); 6.93-6.83 (2H, m); 5.5
6 (2H, AB q, J=10.2Hz, Dn=62.7 ）; 5.47 (2H, s);
3.72-3.66 (3H, m);2.13 (2H, t, J=7.2 Hz); 2.21 (3
H, s); 1.62-1.50 (2H, m). Working Example 417: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-pentanoyloxy
Cimethyl carbamate (Compound No. D1.76) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H, J
= 8.1 Hz); 7.92 (1H, d, J = 7.6 Hz); 7.55-7.41 (2H,
m); 7.09 (1H, d, J = 8.5 Hz); 6.93-6.83 (2H, m); 5.5
6 (2H, AB q, J = 10.2Hz, Dn = 62.7); 5.47 (2H, s);
3.72-3.66 (3H, m); 2.13 (2H, t, J = 7.2 Hz); 2.21 (3
H, s); 1.62-1.50 (2H, m).

【０７２１】[0721]

【実施例４１８】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（ピバロイルオキ
シメチル）カルバマート（化合物番号D1.78 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
４（１Ｈ，ｄ，Ｊ＝７．７Ｈｚ）；７．９２
（１Ｈ，ｄ，Ｊ＝７．０Ｈｚ）；７．３６−
７．５６（２Ｈ，ｍ）；７．０９（１Ｈ，
ｄ，Ｊ＝８．７Ｈｚ）；６．８１−６．９５
（２Ｈ，ｍ）；５．７１（１Ｈ，ｄ，Ｊ＝１
０．６Ｈｚ）；５．４７（２Ｈ，ｓ）；５．
３８（１Ｈ，ｄ，Ｊ＝１０．６Ｈｚ）；３．
７０（３Ｈ，ｂｒ．ｓ）；２．２１（３Ｈ，
ｓ）；１．１８（９Ｈ，ｓ）． Working Example 418 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (pivaloyloxy
Cimethyl) carbamate (Compound No. D1.78) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
4. (1H, d, J = 7.7 Hz); 7.92
(1H, d, J = 7.0 Hz); 7.36−
7.56 (2H, m); 7.09 (1H,
d, J = 8.7 Hz); 6.81-6.95
(2H, m); 5.71 (1H, d, J = 1
5.47 (2H, s);
38 (1H, d, J = 10.6 Hz);
70 (3H, br.s); 2.21 (3H, br.s)
s); 1.18 (9H, s).

【０７２２】[0722]

【実施例４１９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−シクロペンチルカ
ルボニルオキシメチルカルバマート（化合物番号Ｄ１．
７９）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=8.0 Hz); 7.91 (1H,d, J=7.7 Hz); 7.55-7.37 (2
H, m); 7.09 (1H, br.d, J=8.5 Hz); 6.94-6.83 (2H,
m); 5.71 (1H, d, J=10.0 Hz); 5.47 (2H, s); 5.40 (1
H, br.d, J=10.1 Hz); 3.69 (3H, br.s); 2.74 (1H, qu
intet, J=7.9 Hz); 2.21 (3H, s); 1.95-1.53 (8H, m). Working Example 419 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-cyclopentylca
Rubonyloxymethyl carbamate (Compound No. D1.
79) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 8.0 Hz); 7.91 (1H, d, J = 7.7 Hz); 7.55-7.37 (2
H, m); 7.09 (1H, br.d, J = 8.5 Hz); 6.94-6.83 (2H,
m); 5.71 (1H, d, J = 10.0 Hz); 5.47 (2H, s); 5.40 (1
H, br.d, J = 10.1 Hz); 3.69 (3H, br.s); 2.74 (1H, qu
intet, J = 7.9 Hz); 2.21 (3H, s); 1.95-1.53 (8H, m).

【０７２３】[0723]

【実施例４２０】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−シクロヘキシルカ
ルボニルオキシメチルカルバマート（化合物番号D1.80
）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.5 Hz); 7.92 (1H,d, J=7.6 Hz); 7.37-7.57 (2
H, m); 7.08 (1H, d, J=8.5 Hz); 6.81-6.95 (2H,m);
5.71 (1H, d, J=10.2 Hz); 5.47 (2H, s); 5.37 (1H,
d, J=10.2 Hz); 3.31 (1H, m); 2.21 (3H, s); 1.10-1.
95 (10H, m). Working Example 420 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-cyclohexylca
Rubonyloxymethyl carbamate (Compound No. D1.80
) Oil NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.04 (1H,
d, J = 7.5 Hz); 7.92 (1H, d, J = 7.6 Hz); 7.37-7.57 (2
H, m); 7.08 (1H, d, J = 8.5 Hz); 6.81-6.95 (2H, m);
5.71 (1H, d, J = 10.2 Hz); 5.47 (2H, s); 5.37 (1H,
d, J = 10.2 Hz); 3.31 (1H, m); 2.21 (3H, s); 1.10-1.
95 (10H, m).

【０７２４】[0724]

【実施例４２１】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−メトキシアセトキ
シメチルカルバマート（化合物番号D1.81 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.3 Hz); 7.91 (1H,dd, J=7.4 & 1.5 Hz); 7.55-
7.41 (2H, m); 7.08 (1H, d, J=8.5 Hz); 6.94-6.84 (2
H, m); 5.64 (2H, AB q, J=10.3 Hz, Dn=64.5）; 5.47
(2H, s); 4.04 (2H, s); 3.69 (3H, s); 3.41 (3H, s);
2.20 (3H, s). Working Example 421 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-methoxyacetoxy
Cimethyl carbamate (Compound No. D1.81) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.3 Hz); 7.91 (1H, dd, J = 7.4 & 1.5 Hz); 7.55-
7.41 (2H, m); 7.08 (1H, d, J = 8.5 Hz); 6.94-6.84 (2
H, m); 5.64 (2H, AB q, J = 10.3 Hz, Dn = 64.5); 5.47
(2H, s); 4.04 (2H, s); 3.69 (3H, s); 3.41 (3H, s);
2.20 (3H, s).

【０７２５】[0725]

【実施例４２２】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−メトキシアセト
キシメチルカルバマート（化合物番号D1.82 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H,m); 7.43-7.35 (2H, m); 7.11
-7.06 (1H, m); 6.94-6.86 (2H, m); 5.80 (1H,d , J=1
0.5 Hz); 5.55-5.49 (1H, m); 5.31 (2H, s); 4.06 (2
H, s); 3.76 (3H,br.s); 3.41 (3H, s); 2.20 (3H, s). Working Example 422 Methyl N- [4- (benzoxazol-2-ylmeth)
Toxy) -2-methylphenyl] -N-methoxyaceto
Xymethylcarbamate (Compound No. D1.82) oil NMR spectrum (200 MHz, CDCl ₃ ), δppm: 7.79-7.75
(1H, m); 7.60-7.55 (1H, m); 7.43-7.35 (2H, m); 7.11
-7.06 (1H, m); 6.94-6.86 (2H, m); 5.80 (1H, d, J = 1
0.55 Hz); 5.55-5.49 (1H, m); 5.31 (2H, s); 4.06 (2
H, s); 3.76 (3H, br.s); 3.41 (3H, s); 2.20 (3H, s).

【０７２６】[0726]

【実施例４２３】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（３−メトキシプ
ロピオニルオキシメチル）カルバマート（化合物番号D
1.83 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.9 Hz); 7.92 (1H,dd, J=6.9 & 0.9 Hz); 7.55-
7.37 (2H, m); 7.10 (1H, d, J=8.4 Hz); 6.93-6.83 (3
H, m); 5.58 (2H, AB q, J=10.5 Hz, Dn=64.3）; 3.69
(3H, br.s); 3.63(2H, t, J=6.4 Hz); 3.31 (3H, s);
2.59 (2H, t, J=6.4 Hz); 2.20 (3H, s). Working Example 423: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (3-methoxy)
Lopionyloxymethyl) carbamate (Compound No. D
1.83) Oil NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.04 (1H,
d, J = 7.9 Hz); 7.92 (1H, dd, J = 6.9 & 0.9 Hz); 7.55-
7.37 (2H, m); 7.10 (1H, d, J = 8.4 Hz); 6.93-6.83 (3
H, m); 5.58 (2H, AB q, J = 10.5 Hz, Dn = 64.3); 3.69
(3H, br.s); 3.63 (2H, t, J = 6.4 Hz); 3.31 (3H, s);
2.59 (2H, t, J = 6.4 Hz); 2.20 (3H, s).

【０７２７】[0727]

【実施例４２４】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（３−エトキシプ
ロピオニルオキシメチル）カルバマート（化合物番号D
1.85 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.7 Hz); 7.91 (1H,d, J=7.3 Hz); 7.35-7.55 (2
H, m); 7.10 (1H, d, J=8.5 Hz); 6.80-6.94 (2H,m);
5.74 (1H, d, J=10.3 Hz); 5.46 (2H, s); 5.44 (1H,
d, J=10.3 Hz); 3.56-3.85 (5H, m); 3.46 (2H, q, J=
7.0 Hz); 2.59 (3H, t, J=7.0 Hz); 2.20 (3H, s). Working Example 424 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (3-ethoxyp
Lopionyloxymethyl) carbamate (Compound No. D
1.85) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.7 Hz); 7.91 (1H, d, J = 7.3 Hz); 7.35-7.55 (2
H, m); 7.10 (1H, d, J = 8.5 Hz); 6.80-6.94 (2H, m);
5.74 (1H, d, J = 10.3 Hz); 5.46 (2H, s); 5.44 (1H,
d, J = 10.3 Hz); 3.56-3.85 (5H, m); 3.46 (2H, q, J =
7.0 Hz); 2.59 (3H, t, J = 7.0 Hz); 2.20 (3H, s).

【０７２８】[0728]

【実施例４２５】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（３−メチル−３
−ブテノイルオキシメチル）カルバマート（化合物番号
D1.87 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.02 (1H,
d, J=7.7 Hz); 7.88 (1H,dd, J=7.5 & 1.0 Hz); 7.53-
7.38 (2H, m); 7.08 (1H, br.d, J=8.5 Hz); 6.92-6.82
(2H, m); 5.72 (1H, d, J=10.3 Hz); 5.45 (2H, s);
5.41 (1H, br.d, J=10.3 Hz); 4.88 (1H, br.s); 4.82
(1H, br.s); 3.67 (3H, br.s); 3.03 (2H, s); 2.19 (3
H, s); 1.74 (3H, s). Working Example 425 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (3-methyl-3
-Butenoyloxymethyl) carbamate (compound number
D1.87) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.02 (1H,
d, J = 7.7 Hz); 7.88 (1H, dd, J = 7.5 & 1.0 Hz); 7.53-
7.38 (2H, m); 7.08 (1H, br.d, J = 8.5 Hz); 6.92-6.82
(2H, m); 5.72 (1H, d, J = 10.3 Hz); 5.45 (2H, s);
5.41 (1H, br.d, J = 10.3 Hz); 4.88 (1H, br.s); 4.82
(1H, br.s); 3.67 (3H, br.s); 3.03 (2H, s); 2.19 (3
H, s); 1.74 (3H, s).

【０７２９】[0729]

【実施例４２６】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−クロロアセチルオ
キシメチルカルバマート（化合物番号D1.88 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.9 Hz); 7.90 (1H,d, J=7.7 Hz); 7.55-7.37 (2
H, m); 7.10 (1H, d, J=8.5 Hz); 6.94-6.84 (2H,m);
5.82 (1H, d, J=10.1 Hz); 5.48 (1H, d, J=10.1 Hz);
5.47 (2H, s); 4.06 (2H, s); 3.70 (3H, br.s); 2.21
(3H, s). Working Example 426 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-chloroacetyl
Xymethylcarbamate (Compound No. D1.88) Oil NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.04 (1H,
d, J = 7.9 Hz); 7.90 (1H, d, J = 7.7 Hz); 7.55-7.37 (2
H, m); 7.10 (1H, d, J = 8.5 Hz); 6.94-6.84 (2H, m);
5.82 (1H, d, J = 10.1 Hz); 5.48 (1H, d, J = 10.1 Hz);
5.47 (2H, s); 4.06 (2H, s); 3.70 (3H, br.s); 2.21
(3H, s).

【０７３０】[0730]

【実施例４２７】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−ベンゾイルオキシ
メチルカルバマート（化合物番号D1.90 ）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05-8.01
(3H, m); 7.93-7.88 (1H,m); 7.62-7.37 (5H, m); 7.19
-7.13 (1H, m); 6.94 (2H, d, J=3.1 Hz); 6.87(1H, d
d, J=8.6 & 3.1 Hz); 5.98 (1H, d, J=10.7 Hz); 5.70-
5.63 (1H, m); 5.47 (2H, s); 3.83-3.72 (3H, m); 2.2
6 (3H, s). Working Example 427 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-benzoyloxy
Methyl carbamate (Compound No. D1.90) amorphous NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.05-8.01
(3H, m); 7.93-7.88 (1H, m); 7.62-7.37 (5H, m); 7.19
-7.13 (1H, m); 6.94 (2H, d, J = 3.1 Hz); 6.87 (1H, d
d, J = 8.6 & 3.1 Hz); 5.98 (1H, d, J = 10.7 Hz); 5.70-
5.63 (1H, m); 5.47 (2H, s); 3.83-3.72 (3H, m); 2.2
6 (3H, s).

【０７３１】[0731]

【実施例４２８】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−ベンゾイルオキ
シメチルカルバマート（化合物番号D1.91 ）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.12-8.01
(2H, m); 7.79-7.74 (1H,m); 7.61-7.52 (2H, m); 7.48
-7.35 (4H, m); 7.18-7.13 (1H, m); 6.97-6.87(2H,
m); 6.00-5.95 (1H, m); 5.18-5.63 (1H, m); 5.31 (2
H, s); 3.72 (3H, br.s); 2.25 (3H, s). Working Example 428: Methyl N- [4- (benzoxazol-2-ylmethine)
Toxi) -2-methylphenyl] -N-benzoyloxy
Simethylcarbamate (Compound No. D1.91) amorphous NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.12-8.01
(2H, m); 7.79-7.74 (1H, m); 7.61-7.52 (2H, m); 7.48
-7.35 (4H, m); 7.18-7.13 (1H, m); 6.97-6.87 (2H,
m); 6.00-5.95 (1H, m); 5.18-5.63 (1H, m); 5.31 (2
H, s); 3.72 (3H, br.s); 2.25 (3H, s).

【０７３２】[0732]

【実施例４２９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（４−クロロベン
ゾイルオキシメチル）カルバマート（化合物番号D1.92
）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.86-8.08
(4H, m); 7.34-7.56 (4H,m); 7.13 (1H, d, J=8.7 Hz);
6.83-6.97 (2H, m); 5.97 (1H, d, J=10.3 Hz);5.65
(1H, d, J=10.3 Hz); 5.47 (2H, s); 3.70 (3H, br.s);
2.24 (3H, s). Working Example 429 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (4-chloroben
Zoyloxymethyl) carbamate (Compound No. D1.92)
) Oil NMR spectrum (200MHz, CDCl ₃ ), δppm: 7.86-8.08
(4H, m); 7.34-7.56 (4H, m); 7.13 (1H, d, J = 8.7 Hz);
6.83-6.97 (2H, m); 5.97 (1H, d, J = 10.3 Hz); 5.65
(1H, d, J = 10.3 Hz); 5.47 (2H, s); 3.70 (3H, br.s);
2.24 (3H, s).

【０７３３】[0733]

【実施例４３０】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（４−メチルベン
ゾイルオキシメチル）カルバマート（化合物番号D1.93
）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05-7.88
(2H, m); 6.94-6.83 (5H,m); 5.81 (2H, AB q, J=10.6
Hz, Dn=60.7 ）；５．４６（２Ｈ，ｓ）；３．
８８−３．７０（３Ｈ，ｍ）；２．４１（３Ｈ，
ｓ）；２．２５（３Ｈ，ｓ）． Working Example 430 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (4-methylben
Zoyloxymethyl) carbamate (Compound No. D1.93)
) Oil NMR spectrum (200MHz, CDCl ₃ ), δppm: 8.05-7.88
(2H, m); 6.94-6.83 (5H, m); 5.81 (2H, AB q, J = 10.6
Hz, Dn = 60.7); 5.46 (2H, s);
88-3.70 (3H, m); 2.41 (3H,
s); 2.25 (3H, s).

【０７３４】[0734]

【実施例４３１】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（４−メトキシベ
ンゾイルオキシメチル）カルバマート（化合物番号Ｄ
１．９４）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.06-7.88
(4H, m); 7.55-7.37 (2H,m); 7.14 (1H, d, J=8.9 Hz);
6.93-6.83 (4H, m); 5.79 (2H, AB q, J=10.3 Hz, Dn=
60.8); 5.46 (2H, s); 3.86 (3H, s); 3.72 (3H, br.
s); 2.24 (3H, s). Working Example 431: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (4-methoxy
Nzoyloxymethyl) carbamate (Compound No. D
1.94) Amorphous NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.06-7.88
(4H, m); 7.55-7.37 (2H, m); 7.14 (1H, d, J = 8.9 Hz);
6.93-6.83 (4H, m); 5.79 (2H, AB q, J = 10.3 Hz, Dn =
60.8); 5.46 (2H, s); 3.86 (3H, s); 3.72 (3H, br.
s); 2.24 (3H, s).

【０７３５】[0735]

【実施例４３２】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（フェニルアセト
キシメチル）カルバマート（化合物番号D1.95 ）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=7.3 Hz); 7.92 (1H,d, J=7.4 Hz); 7.35-7.55 (2
H, m); 7.18-7.33 (5H, m); 6.70-6.91 (3H, m);5.76
(1H, d, J=10.0 Hz); 5.45 (2H, s); 5.38 (1H, d, J=1
0.0 Hz); 3.68 (3H, br.s); 3.63 (2H, s); 2.11 (3H,
s). Working Example 432 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (phenylacetoacetate
Xymethyl) carbamate (Compound No. D1.95) oil NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.05 (1H,
d, J = 7.3 Hz); 7.92 (1H, d, J = 7.4 Hz); 7.35-7.55 (2
H, m); 7.18-7.33 (5H, m); 6.70-6.91 (3H, m); 5.76
(1H, d, J = 10.0 Hz); 5.45 (2H, s); 5.38 (1H, d, J = 1
0.0 Hz); 3.68 (3H, br.s); 3.63 (2H, s); 2.11 (3H, br.s)
s).

【０７３６】[0736]

【実施例４３３】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−テノイルオ
キシメチル）カルバマート（化合物番号D1.97 ）ガム状ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
３（１Ｈ，ｄ，Ｊ＝７．６Ｈｚ）；７．９１
（１Ｈ，ｄ，Ｊ＝７．０Ｈｚ）；７．８０
（１Ｈ，ｍ）；７．３６−７．５９（３Ｈ，
ｍ）；７．０６−７．１９（２Ｈ，ｍ）；６．
８２−６．８９（２Ｈ，ｍ）；５．９２（１
Ｈ，ｄ，Ｊ＝１０．２Ｈｚ）；５．６５（１
Ｈ，ｄ，Ｊ＝１０．２Ｈｚ）；５．４７（２
Ｈ，ｓ）；３．７１（３Ｈ，ｂｒ．ｓ）；
２．２５（３Ｈ，ｓ）． Working Example 433 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-thenoylo
(Xymethyl) carbamate (Compound No. D1.97) gum-like NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
3. (1H, d, J = 7.6 Hz); 7.91
(1H, d, J = 7.0 Hz); 7.80
(1H, m); 7.36-7.59 (3H,
5. m); 7.06-7.19 (2H, m);
82-6.89 (2H, m); 5.92 (1
H, d, J = 10.2 Hz); 5.65 (1
H, d, J = 10.2 Hz); 5.47 (2
H, s); 3.71 (3H, br.s);
2.25 (3H, s).

【０７３７】[0737]

【実施例４３４】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−（２−テノイル
オキシメチル）カルバマート（化合物番号Ｄ１．９８）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.82-7.75
(2H, m); 7.59-7.54 (2H,m); 7.40-7.35 (2H, m); 7.17
-7.08 (2H, m); 6.96-6.87 (2H, m); 5.94-5.89(1H,
m); 5.67-5.62 (1H, m); 5.31 (2H, s); 3.71 (3H, br.
s); 2.25 (3H, s).Working Example 434 Methyl N- [4- (benzoxazol-2-ylmethy !
Toxy) -2-methylphenyl] -N- (2-thenoyl
(Oxymethyl) carbamate (Compound No. D1.98) amorphous NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.82-7.75
(2H, m); 7.59-7.54 (2H, m); 7.40-7.35 (2H, m); 7.17
-7.08 (2H, m); 6.96-6.87 (2H, m); 5.94-5.89 (1H,
m); 5.67-5.62 (1H, m); 5.31 (2H, s); 3.71 (3H, br.
s); 2.25 (3H, s).

【０７３８】[0738]

【実施例４３５】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−フロイルオ
キシメチル）カルバマート（化合物番号D1.99 ）ガム状ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.3 Hz); 7.90 (1H,d, J=7.3 Hz); 7.34-7.69 (3
H, m); 7.08-7.21 (2H, m); 6.83-6.95 (2H, m);6.50
(1H, m); 5.91 (1H, d, J=10.3 Hz); 5.66 (1H, d, J=1
0.3 Hz); 5.46 (2H, s); 3.71 (3H, br.s); 2.24 (3H,
s). Working Example 435 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-fluoroyl)
(Ximethyl) carbamate (Compound No. D1.99) gum-like NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.03 (1H,
d, J = 7.3 Hz); 7.90 (1H, d, J = 7.3 Hz); 7.34-7.69 (3
H, m); 7.08-7.21 (2H, m); 6.83-6.95 (2H, m); 6.50
(1H, m); 5.91 (1H, d, J = 10.3 Hz); 5.66 (1H, d, J = 1
0.346); 5.46 (2H, s); 3.71 (3H, br.s); 2.24 (3H, s.)
s).

【０７３９】[0739]

【実施例４３６】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（ニコチノイルオ
キシメチル）カルバマート（化合物番号D1.100）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：９．２
１（１Ｈ，ｍ）；８．７９（１Ｈ，ｄｄ，
Ｊ＝２．０＆４．７Ｈｚ）；８．２８（１Ｈ，
ｄｔ，Ｊｄ＝８．１Ｈｚ，Ｊｔ＝１．５Ｈ
ｚ）；８．０３（１Ｈ，ｄ，Ｊ＝８．０Ｈ
ｚ）；７．９０（１Ｈ，ｄ，Ｊ＝８．７Ｈ
ｚ）；７．３７−７．５６（３Ｈ，ｍ）；７．
１５（１Ｈ，ｄ，Ｊ＝８．４Ｈｚ）；６．８
１−６．９６（２Ｈ，ｍ）；６．０２（１Ｈ，
ｄ，Ｊ＝１０．３Ｈｚ）；５．６７（１Ｈ，
ｄ，Ｊ＝１０．３Ｈｚ）；５．４７（２Ｈ，
ｓ）；３．７２（３Ｈ，ｂｒ．ｓ）；２．２
５（３Ｈ，ｓ）． Working Example 436 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (nicotinoylo)
(Xmethyl) carbamate (Compound No. D1.100) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 9.2
1 (1H, m); 8.79 (1H, dd,
J = 2.0 & 4.7 Hz); 8.28 (1H,
dt, Jd = 8.1 Hz, Jt = 1.5 H
z); 8.03 (1H, d, J = 8.0 H)
z); 7.90 (1H, d, J = 8.7 H)
z); 7.37-7.56 (3H, m);
15 (1H, d, J = 8.4 Hz); 6.8
1-6.96 (2H, m); 6.02 (1H,
d, J = 10.3 Hz); 5.67 (1H,
d, J = 10.3 Hz); 5.47 (2H,
3.72 (3H, br.s); 2.2
5 (3H, s).

【０７４０】[0740]

【実施例４３７】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−クロロニコ
チノイルオキシメチル）カルバマート（化合物番号Ｄ
１．１０１）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.53 (1H, d
d, J=1.9 & 4.8 Hz); 8.16 (1H, dd, J=1.9 & 7.8 Hz);
8.03 (1H, d, J=7.7 Hz); 7.90 (1H, d, J=7.0Hz); 7.
29-7.55 (3H, m); 7.17 (1H, d, J=8.8 Hz); 6.83-6.94
(2H, m); 6.04(1H, d, J=10.3 Hz); 5.60 (1H, d, J=1
0.3 Hz); 5.47 (2H, s); 3.72 (3H, br.s); 2.04 (3H,
s). Working Example 437 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-chloronico
Tinoyloxymethyl) carbamate (Compound No. D
1.101) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.53 (1H, d
d, J = 1.9 & 4.8 Hz); 8.16 (1H, dd, J = 1.9 & 7.8 Hz);
8.03 (1H, d, J = 7.7 Hz); 7.90 (1H, d, J = 7.0Hz); 7.
29-7.55 (3H, m); 7.17 (1H, d, J = 8.8 Hz); 6.83-6.94
(2H, m); 6.04 (1H, d, J = 10.3 Hz); 5.60 (1H, d, J = 1
0.3 Hz); 5.47 (2H, s); 3.72 (3H, br.s); 2.04 (3H, s.)
s).

【０７４１】[0741]

【実施例４３８】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−ピラジンカ
ルボニルオキシメチル）カルバマート（化合物番号D1.1
02）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 9.27 (1H,
d, J=1.4 Hz); 8.72 (2H,m); 8.02 (1H, d, J=7.3 Hz);
7.90 (1H, d, J=7.7 Hz); 7.35-7.54 (2H, m);7.19 (1
H, d, J=8.5 Hz); 6.82-6.96 (2H, m); 6.08 (1H, d, J
=10.3 Hz); 5.74(1H, d, J=10.3 Hz); 5.46 (2H, s);
3.72 (3H, br.s); 2.26 (3H, s). Working Example 438 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-pyrazinka
Rubonyloxymethyl) carbamate (Compound No. D1.1
02) Oily substance NMR spectrum (200MHz, CDCl ₃ ), δppm: 9.27 (1H,
d, J = 1.4 Hz); 8.72 (2H, m); 8.02 (1H, d, J = 7.3 Hz);
7.90 (1H, d, J = 7.7 Hz); 7.35-7.54 (2H, m); 7.19 (1
H, d, J = 8.5 Hz); 6.82-6.96 (2H, m); 6.08 (1H, d, J
= 10.3 Hz); 5.74 (1H, d, J = 10.3 Hz); 5.46 (2H, s);
3.72 (3H, br.s); 2.26 (3H, s).

【０７４２】[0742]

【実施例４３９】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−メトキシカルボニ
ルオキシメチルカルバマート（化合物番号D1.103）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=8.0 Hz); 7.90 (1H,d, J=7.0 Hz); 7.54-7.37 (2
H, m); 7.14-7.08 (1H, m); 6.94-6.84 (2H, m);5.79
(1H, br.d, J=9.8 Hz); 5.47 (2H, s); 5.38 (1H, d, J
=9.8 Hz); 3.75 (3H, s); 3.67 (3H, br.s); 2.20 (3H,
s). Working Example 439 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-methoxycarbonyl
Ruoxymethyl carbamate (Compound No. D1.103) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 8.0 Hz); 7.90 (1H, d, J = 7.0 Hz); 7.54-7.37 (2
H, m); 7.14-7.08 (1H, m); 6.94-6.84 (2H, m); 5.79
(1H, br.d, J = 9.8 Hz); 5.47 (2H, s); 5.38 (1H, d, J
= 9.8 Hz); 3.75 (3H, s); 3.67 (3H, br.s); 2.20 (3H, s.)
s).

【０７４３】[0734]

【実施例４４０】メチルＮ−［４−（ベンゾオキサゾール−２−イルメ
トキシ）−２−メチルフェニル］−Ｎ−メトキシカルボ
ノイルオキシメチルカルバマート（化合物番号D1.104）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 7.79-7.75
(1H, m); 7.60-7.54 (1H,m); 7.43-7.33 (2H, m); 7.12
-7.07 (1H, m); 6.95-6.85 (2H, m); 5.82-5.75(1H,
m); 5.42-5.35 (1H, m); 5.31 (2H, s); 3.75 (6H, br.
s); 2.20 (3H, s). Working Example 440 Methyl N- [4- (benzoxazol-2-ylmethy)
Toxi) -2-methylphenyl] -N-methoxycarbo
Noyloxymethyl carbamate (Compound No. D1.104) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 7.79-7.75
(1H, m); 7.60-7.54 (1H, m); 7.43-7.33 (2H, m); 7.12
-7.07 (1H, m); 6.95-6.85 (2H, m); 5.82-5.75 (1H, m
m); 5.42-5.35 (1H, m); 5.31 (2H, s); 3.75 (6H, br.
s); 2.20 (3H, s).

【０７４４】[0744]

【実施例４４１】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−フェノキシ
エチル）カルバマート（化合物番号D1.117）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.6 Hz); 7.91 (1H,d, J=7.5 Hz); 7.55-7.36 (2
H, m); 7.28-7.20 (2H, m); 7.11 (1H, d, J=8.6Hz);
6.96-6.80 (5H, m); 5.47 (2H, s); 4.17-4.07 (3H,
m); 3.84-3.71 (1H,m); 3.64 (3H, br.s); 2.18 (3H,
s). Working Example 441: Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-phenoxy
Ethyl) carbamate (Compound No. D1.117) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.6 Hz); 7.91 (1H, d, J = 7.5 Hz); 7.55-7.36 (2
H, m); 7.28-7.20 (2H, m); 7.11 (1H, d, J = 8.6Hz);
6.96-6.80 (5H, m); 5.47 (2H, s); 4.17-4.07 (3H,
m); 3.84-3.71 (1H, m); 3.64 (3H, br.s); 2.18 (3H,
s).

【０７４５】[0745]

【実施例４４２】Ｎ−（２−アセチルオキシエチル）−Ｎ−［４−（ベン
ゾチアゾール−２−イルメトキシ）−２−メチルフェニ
ル］アセトアミド（化合物番号D1.122）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
７−８．０３（１Ｈ，ｍ）；７．９４−７．９０
（１Ｈ，ｍ）；７．５６−７．３９（２Ｈ，
ｍ）；７．１０（１Ｈ，ｄ，Ｊ＝８．４Ｈ
ｚ）；６．９７（１Ｈ，ｄ，Ｊ＝３．２Ｈ
ｚ）；６．９０（１Ｈ，ｄｄ，Ｊ＝８．８＆
２．８Ｈｚ）；５．４９（２Ｈ，ｓ）；４．
３６−４．１８（３Ｈ，ｍ）；３．４２−３．３
３（１Ｈ，ｍ）；２．２０（３Ｈ，ｓ）；
１．９５（３Ｈ，ｓ）；１．７６（３Ｈ，
ｓ）．Working Example 442 N- (2-acetyloxyethyl) -N- [4- (ben
Zothiazol-2-ylmethoxy) -2-methylpheni
Acetamide (Compound No. D1.122) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
7-8.03 (1H, m); 7.94-7.90
(1H, m); 7.56-7.39 (2H,
m); 7.10 (1H, d, J = 8.4H
z); 6.97 (1H, d, J = 3.2H)
z); 6.90 (1H, dd, J = 8.8 &
2.8 Hz); 5.49 (2H, s);
36-4.18 (3H, m); 3.42-3.3
3. (1H, m); 2.20 (3H, s);
1.95 (3H, s); 1.76 (3H,
s).

【０７４６】[0746]

【実施例４４３】メチルＮ−（２−アセトキシエチル）−Ｎ−［４−
（ベンゾチアゾール−２−イルメトキシ）−２−メチル
フェニル］カルバマート（化合物番号Ｄ１．１２３）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=7.5 Hz); 7.91 (1H,d, J=7.4 Hz); 7.58-7.37 (2
H, m); 7.12-6.80 (3H, m); 5.47 (2H, s); 4.25-4.12
(2H, br.m); 4.07-3.52 (2H, m); 3.64 (3H, s); 2.18
(3H, br.s); 1.96(3H, s).Working Example 443 Methyl N- (2-acetoxyethyl) -N- [4-
(Benzothiazol-2-ylmethoxy) -2-methyl
Phenyl] carbamate (Compound No. D1.123) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 7.5 Hz); 7.91 (1H, d, J = 7.4 Hz); 7.58-7.37 (2
H, m); 7.12-6.80 (3H, m); 5.47 (2H, s); 4.25-4.12
(2H, br.m); 4.07-3.52 (2H, m); 3.64 (3H, s); 2.18
(3H, br.s); 1.96 (3H, s).

【０７４７】[0747]

【実施例４４４】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−（２−プロピオニルオキシ
エチル）アセトアミド（化合物番号D1.125）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-8.03
(1H, m); 7.94-7.89 (1H,m); 7.56-7.38 (2H, m); 7.10
(1H, d, J=8.6 Hz); 6.97 (1H, d, J=3.0 Hz);6.89 (1
H, dd, J=8.4 & 3.0 Hz); 5.49 (2H, s); 4.37-4.20 (3
H, m); 3.42-3.33 (1H, m); 2.28-2.17 (5H, m); 1.76
(3H, s); 1.05 (3H, t, J=7.6 Hz).Example 444 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- (2-propionyloxy
Ethyl) acetamide (Compound No. D1.125) oil NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.07-8.03
(1H, m); 7.94-7.89 (1H, m); 7.56-7.38 (2H, m); 7.10
(1H, d, J = 8.6 Hz); 6.97 (1H, d, J = 3.0 Hz); 6.89 (1
H, dd, J = 8.4 & 3.0 Hz); 5.49 (2H, s); 4.37-4.20 (3
H, m); 3.42-3.33 (1H, m); 2.28-2.17 (5H, m); 1.76
(3H, s); 1.05 (3H, t, J = 7.6 Hz).

【０７４８】[0748]

【実施例４４５】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−プロピオニ
ルオキシエチル）カルバマート（化合物番号D1.126）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
４（１Ｈ，ｄ，Ｊ＝７．２Ｈｚ）；７．９１
（１Ｈ，ｄ，Ｊ＝６．８Ｈｚ）；７．５５−
７．３８（２Ｈ，ｍ）；７．０７（１Ｈ，
ｄ，Ｊ＝８．８Ｈｚ）；６．９４−６．８１
（２Ｈ，ｍ）；５．４７（２Ｈ，ｓ）；４．２
６−４．１２（２Ｈ，ｍ）；４．１０−３．８８
（１Ｈ，ｍ）；３．８０−３．５０（１Ｈ，
ｍ）；３．６３（１Ｈ，ｓ）；２．２４（２
Ｈ，ｑ，Ｊ＝７．７Ｈｚ）；２．１８（３
Ｈ，ｓ）；１．０６（３Ｈ，ｔ，Ｊ＝７．５
Ｈｚ）． Working Example 445 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-propioni
Loxyethyl) carbamate (Compound No. D1.126) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
4. (1H, d, J = 7.2 Hz); 7.91
(1H, d, J = 6.8 Hz); 7.55-
7.38 (2H, m); 7.07 (1H,
d, J = 8.8 Hz); 6.94-6.81
(2H, m); 5.47 (2H, s); 4.2
6-4.12 (2H, m); 4.10-3.88
(1H, m); 3.80-3.50 (1H, m)
m); 3.63 (1H, s); 2.24 (2
H, q, J = 7.7 Hz); 2.18 (3
H, s); 1.06 (3H, t, J = 7.5)
Hz).

【０７４９】[0749]

【実施例４４６】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−（２−シクロブチルカルボ
ニルオキシエチル）アセトアミド（化合物番号Ｄ１．１
２８）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.89
(2H, m); 7.53-7.42 (2H,m); 7.10 (1H, d, J=8.6 Hz);
7.09 (1H, d, J=8.4 Hz); 6.97-6.87 (2H, m);5.49 (2
H, s); 4.38-4.20 (3H, m); 3.41-2.98 (2H, m); 2.32-
1.76 (12H, m).Working Example 446 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- (2-cyclobutylcarbo
Nyloxyethyl) acetamide (Compound No. D1.1)
28) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.89
(2H, m); 7.53-7.42 (2H, m); 7.10 (1H, d, J = 8.6 Hz);
7.09 (1H, d, J = 8.4 Hz); 6.97-6.87 (2H, m); 5.49 (2
H, s); 4.38-4.20 (3H, m); 3.41-2.98 (2H, m); 2.32-
1.76 (12H, m).

【０７５０】[0750]

【実施例４４７】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−（２−クロロアセトキシエ
チル）アセトアミド（化合物番号D1.129）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.05 (1H,
d, J=7.4 Hz); 7.91 (1H,d, J=7.7 Hz); 7.52-7.42 (2
H, m); 7.14-6.89 (3H, m); 5.50 (2H, s); 4.38-4.31
(3H, m); 3.96 (3H, s); 3.38-3.24 (1H, m); 2.20 (3
H, s); 1.76 (3H, s).Working Example 447 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- (2-chloroacetoxy
Tyl) acetamide (Compound No. D1.129) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.05 (1H,
d, J = 7.4 Hz); 7.91 (1H, d, J = 7.7 Hz); 7.52-7.42 (2
H, m); 7.14-6.89 (3H, m); 5.50 (2H, s); 4.38-4.31
(3H, m); 3.96 (3H, s); 3.38-3.24 (1H, m); 2.20 (3
H, s); 1.76 (3H, s).

【０７５１】[0751]

【実施例４４８】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−［２−（２−メトキシアセ
トキシ) エチル］アセトアミド（化合物番号D1.130）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
５（１Ｈ，ｄ，Ｊ＝８．０Ｈｚ）；７．９２
（１Ｈ，ｄ，Ｊ＝７．３Ｈｚ）；７．５６−
７．３８（２Ｈ，ｍ）；７．１２（１Ｈ，
ｄ，Ｊ＝８．６Ｈｚ）；６．９６−６．８７
（２Ｈ，ｍ）；５．４９（２Ｈ，ｓ）；４．４
０−４．３０（３Ｈ，ｍ）；３．９４（２Ｈ，
ｓ）；３．３８（３Ｈ，ｓ）；３．４４−
３．３１（１Ｈ，ｍ）；２．２０（３Ｈ，
ｓ）；１．７６（３Ｈ，ｓ）．Working Example 448 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- [2- (2-methoxyace
Toxy) ethyl] acetamide (Compound No. D1.130) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
5 (1H, d, J = 8.0 Hz); 7.92
(1H, d, J = 7.3 Hz); 7.56-
7.38 (2H, m); 7.12 (1H, m)
d, J = 8.6 Hz); 6.96-6.87
(2H, m); 5.49 (2H, s); 4.4
0-4.30 (3H, m); 3.94 (2H, m)
3.38 (3H, s); 3.44-
3.31 (1H, m); 2.20 (3H,
s); 1.76 (3H, s).

【０７５２】[0752]

【実施例４４９】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−（２−ベンゾイルオキシエ
チル）アセトアミド（化合物番号Ｄ１．１３１）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.07-7.88
(4H, m); 7.57-7.33 (5H,m); 7.09 (1H, d, J=8.6 Hz);
6.95 (1H, d, J=3.0 Hz); 6.82 (1H, dd, J=8.8& 3.0
Hz); 5.45 (2H, s); 4.48-4.41 (3H, m); 3.61-3.54 (1
H, m); 2.22 (3H, s); 1.78 (3H, s).Working Example 449 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- (2-benzoyloxy
Tyl) acetamide (Compound No. D1.131) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.07-7.88
(4H, m); 7.57-7.33 (5H, m); 7.09 (1H, d, J = 8.6 Hz);
6.95 (1H, d, J = 3.0 Hz); 6.82 (1H, dd, J = 8.8 & 3.0
Hz); 5.45 (2H, s); 4.48-4.41 (3H, m); 3.61-3.54 (1
H, m); 2.22 (3H, s); 1.78 (3H, s).

【０７５３】[0753]

【実施例４５０】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−（２−ベンゾイル
オキシエチル）カルバマート（化合物番号D1.132）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04 (1H,
d, J=8.2 Hz); 7.93-7.90(3H, m); 7.55-7.34 (5H, m);
7.08 (1H, d, J=8.8 Hz); 6.90 (1H, d, J=2.6Hz); 6.
81 (1H, dd, J=8.8 & 2.6 Hz); 5.44 (2H, s); 4.48-4.
43 (2H, m); 4.21-4.05 (1H, m); 3.84-3.76 (1H, m);
3.65 (3H, s); 2.18 (3H, s). Working Example 450 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- (2-benzoyl
Oxyethyl) carbamate (Compound No. D1.132) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.04 (1H,
d, J = 8.2 Hz); 7.93-7.90 (3H, m); 7.55-7.34 (5H, m);
7.08 (1H, d, J = 8.8 Hz); 6.90 (1H, d, J = 2.6 Hz); 6.
81 (1H, dd, J = 8.8 & 2.6 Hz); 5.44 (2H, s); 4.48-4.
43 (2H, m); 4.21-4.05 (1H, m); 3.84-3.76 (1H, m);
3.65 (3H, s); 2.18 (3H, s).

【０７５４】[0754]

【実施例４５１】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−［２−（２−フロイルオキ
シ) エチル］アセトアミド（化合物番号D1.135）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
７−８．０３（１Ｈ，ｍ）；７．９４−７．８９
（１Ｈ，ｍ）；７．５７−７．３９（１Ｈ，
ｍ）；７．１４（１Ｈ，ｄ，Ｊ＝８．６Ｈ
ｚ）；７．０６（１Ｈ，ｄ，Ｊ＝３．０Ｈ
ｚ）；６．９５（１Ｈ，ｄ，Ｊ＝３．０Ｈ
ｚ）；６．８４（１Ｈ，ｄｄ，Ｊ＝８．４＆
２．６Ｈｚ）；６．４３（１Ｈ，ｄｄ，Ｊ
＝３．６＆１．８Ｈｚ）；５．４７（２Ｈ，
ｓ）；４．５０−４．３７（３Ｈ，ｍ）；
３．５７−３．４３（１Ｈ，ｍ）；１．７７
（３Ｈ，ｓ）；２．２１（３Ｈ，ｓ）．Working Example 451 N- [4- (Benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- [2- (2-furoyloxy)
E) Ethyl] acetamide (Compound No. D1.135) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
7-8.03 (1H, m); 7.94-7.89
(1H, m); 7.57-7.39 (1H,
m); 7.14 (1H, d, J = 8.6H
z); 7.06 (1H, d, J = 3.0 H)
z); 6.95 (1H, d, J = 3.0H)
z); 6.84 (1H, dd, J = 8.4 &
6.43 (1H, dd, J)
= 3.6 & 1.8 Hz); 5.47 (2H,
s); 4.50-4.37 (3H, m);
3.57-3.43 (1H, m); 1.77
(3H, s); 2.21 (3H, s).

【０７５５】[0755]

【実施例４５２】Ｎ−［４−（ベンゾチアゾール−２−イルメトキシ）−
２−メチルフェニル］−Ｎ−（２−イソニコチノイルオ
キシエチル）アセトアミド（化合物番号Ｄ１．１３６油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.75 (2H, d
d, J=4.4 & 1.1 Hz); 8.05 (1H, d, J=8.1 Hz); 7.92
(1H, d, J=8.3 Hz); 7.74 (2H, dd, J=4.4 & 1.1Hz);
7.56-7.38 (2H, m); 7.07 (1H, d, J=8.5 Hz); 6.97 (1
H, d, J=2.9 Hz);6.85 (1H, dd, J=8.5 & 2.9 Hz); 5.4
7 (2H, s); 4.52-4.43 (3H, m); 3.59-3.49 (1H, m);
2.22 (3H, s); 1.78 (3H, s).Working Example 452 N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N- (2-isonicotinoylo
Xyethyl) acetamide (Compound No. D1.136 oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.75 (2H, d
d, J = 4.4 & 1.1 Hz); 8.05 (1H, d, J = 8.1 Hz); 7.92
(1H, d, J = 8.3 Hz); 7.74 (2H, dd, J = 4.4 &1.1Hz);
7.56-7.38 (2H, m); 7.07 (1H, d, J = 8.5 Hz); 6.97 (1
H, d, J = 2.9 Hz); 6.85 (1H, dd, J = 8.5 & 2.9 Hz); 5.4
7 (2H, s); 4.52-4.43 (3H, m); 3.59-3.49 (1H, m);
2.22 (3H, s); 1.78 (3H, s).

【０７５６】[0756]

【実施例４５３】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−フェナシルカルバ
マート（化合物番号D1.37 ）アモルファスＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.04-7.87
(4H, m); 7.57-7.38 (6H,m); 6.92-6.83 (2H, m); 5.45
(2H, s); 4.93 (2H, AB q, J=17.8 Hz, Dn=184.1 ）;
3.69 (3H, s); 2.29 (3H, s). Working Example 453 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N-phenacylcarba
Mart (Compound No. D1.37) amorphous NMR spectrum (200 MHz, CDCl ₃ ), δppm: 8.04-7.87
(4H, m); 7.57-7.38 (6H, m); 6.92-6.83 (2H, m); 5.45
(2H, s); 4.93 (2H, AB q, J = 17.8 Hz, Dn = 184.1);
3.69 (3H, s); 2.29 (3H, s).

【０７５７】[0757]

【実施例４５４】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−［１−( エトキシ
カルボニル）エチル］カルバマート（化合物番号D1.46
）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δｐｐｍ：８．０
４（１Ｈ，ｄ，Ｊ＝７．７Ｈｚ）；７．９１
（１Ｈ，ｄ，Ｊ＝８．０Ｈｚ）；７．５６−
７．３５（２Ｈ，ｍ）；６．９５−６．８２
（２Ｈ，ｍ）；５．４７（２Ｈ，ｓ）；４．
３１−４．１５（３Ｈ，ｍ）；３．７５−３．６
４（３Ｈ，ｍ）；２．１９（３Ｈ，ｂｒ．
ｓ）；１．３１（３Ｈ，ｔ，Ｊ＝７．１Ｈ
ｚ）；１．１４（３Ｈ，ｄ，Ｊ＝７．６Ｈ
ｚ）． Working Example 454 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- [1- (ethoxy
Carbonyl) ethyl] carbamate (Compound No. D1.46
) Oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.0
4. (1H, d, J = 7.7 Hz); 7.91
(1H, d, J = 8.0 Hz); 7.56-
7.35 (2H, m); 6.95-6.82
(2H, m); 5.47 (2H, s);
31-4.15 (3H, m); 3.75-3.6
4 (3H, m); 2.19 (3H, br.
1.31 (3H, t, J = 7.1 H)
z); 1.14 (3H, d, J = 7.6H)
z).

【０７５８】[0758]

【実施例４５５】メチルＮ−［４−（ベンゾチアゾール−２−イルメト
キシ）−２−メチルフェニル］−Ｎ−［４−クロロフェ
ニルチオメチル）カルバマート（化合物番号D1.65）油状物ＮＭＲスペクトル(200MHz,CDCl₃), δppm: 8.03 (1H,
d, J=7.4 Hz); 7.88 (1H,d, J=8.1 Hz); 7.52-7.38 (2
H, m); 7.22 (2H, d, J=8.6 Hz); 7.14 (2H, d, J=8.6
Hz); 7.02 (1H, br.d, J=8.4 Hz); 6.87-6.79 (2H, m);
5.43 (2H, s); 5.28 (1H, d, J=15.3 Hz); 4.88 (1H,
br.d, J=15.3 Hz); 3.61 (3H, s); 2.13 (3H, br.s). Working Example 455 Methyl N- [4- (benzothiazol-2-ylmethoate)
Xy) -2-methylphenyl] -N- [4-chlorophen
Nylthiomethyl) carbamate (Compound No. D1.65) oil NMR spectrum (200 MHz, CDCl ₃ ), δ ppm: 8.03 (1H,
d, J = 7.4 Hz); 7.88 (1H, d, J = 8.1 Hz); 7.52-7.38 (2
H, m); 7.22 (2H, d, J = 8.6 Hz); 7.14 (2H, d, J = 8.6
Hz); 7.02 (1H, br.d, J = 8.4 Hz); 6.87-6.79 (2H, m);
5.43 (2H, s); 5.28 (1H, d, J = 15.3 Hz); 4.88 (1H,
br.d, J = 15.3 Hz); 3.61 (3H, s); 2.13 (3H, br.s).

【０７５９】[0759]

【製剤例】下記製剤例において、「％」とあるのは、重
量％を示す。[Formulation Examples] In the following formulation examples, "%" indicates% by weight.

【０７６０】[0760]

【製剤例１】（水和剤）前記実施例１の化合物（Ａ１．１番）２５部、ドデシル
ベンゼンスルホン酸ナトリウム塩２．５部、リグニンス
ルホン酸カルシウム塩２．５部及び珪藻土７０部を、よ
く混合し、エアーミルで粉砕して、Ａ１．１番の化合物
を２５％含有する水和剤を得た。Formulation Example 1 (Wettable powder) 25 parts of the compound of Example 1 (No. A1.1), 2.5 parts of sodium dodecylbenzenesulfonate, 2.5 parts of calcium ligninsulfonate and 70 parts of diatomaceous earth The mixture was mixed well and pulverized with an air mill to obtain a wettable powder containing 25% of the compound No. A1.1.

【０７６１】[0761]

【製剤例２】（乳剤）前記実施例１１の化合物（Ａ１．５番）３０部、ドデシ
ルベンゼンスルホン酸カルシウム塩２．６８部、ポリオ
キシエチレンステアリルエーテル４．９２部及びポリオ
キシエチレンノニルフェニルエーテルリン酸カルシウム
塩０．４部をキシレン６２部に溶解し、よく混合して、
Ａ１．５番の化合物を３０％含有する乳剤を得た。Formulation Example 2 (Emulsion) 30 parts of the compound of Example 11 (# A1.5), 2.68 parts of calcium salt of dodecylbenzenesulfonic acid, 4.92 parts of polyoxyethylene stearyl ether and polyoxyethylene nonylphenyl ether Dissolve 0.4 part of calcium phosphate salt in 62 parts of xylene, mix well,
An emulsion containing 30% of the compound No. A1.5 was obtained.

【０７６２】[0762]

【製剤例３】（粒剤）前記実施例２１の化合物（Ｃ１．５番）５部、ホワイト
カーボン（合成シリカ）１部、リグニンスルホン酸カル
シウム塩５部、ベントナイト２０部及びクレー（炭酸カ
ルシウム）６９部を、混合し、エアーミルで粉砕した。
粉砕物をニーダーに入れ、水１８部を加えてよく練り合
せた後、開孔径０．７ｍｍのスクリーンより押し出し造
粒した。造粒湿品を、７０℃に設定した送風乾燥機中で
乾燥し、直径１．００ｍｍ〜０．３０ｍｍ区分に整粒し
て、粒剤を得た。Formulation Example 3 (Granules) 5 parts of the compound of Example 21 (No. C1.5), 1 part of white carbon (synthetic silica), 5 parts of calcium ligninsulfonate, 20 parts of bentonite, and clay (calcium carbonate) 69 parts were mixed and pulverized with an air mill.
The pulverized product was put in a kneader, and 18 parts of water was added thereto and kneaded well, and then extruded through a screen having an opening diameter of 0.7 mm to perform granulation. The granulated wet product was dried in a blow dryer set at 70 ° C., and sized to 1.00 mm to 0.30 mm diameter to obtain granules.

【０７６３】[0763]

【製剤例４】（水和顆粒）前記実施例２９の化合物（Ｃ１．１番）８０部、ポリア
クリル酸重合物ナトリウム塩１．２５部、水３．７５
部、ドデシルベンゼンスルホン酸ナトリウム塩３部、デ
キストリン７部及び酸化チタン５部を、エアーミルを用
いて粉砕・混合した。次いで、回転ミキサー又は流動床
ミキサー中に加え、水を噴霧して顆粒化させた。大部分
が１．００ｍｍ〜０．１５ｍｍになったら顆粒を取り出
し、送風乾燥機で乾燥後、篩にかけた。オーバーサイズ
の物質をジェットミルで粉砕し、１．００〜０．１５ｍ
ｍの顆粒を得た。Formulation Example 4 (Hydrated granules) 80 parts of the compound of Example 29 (No. C1.1), 1.25 parts of sodium salt of polyacrylic acid polymer, and 3.75 of water
Parts, 3 parts of sodium dodecylbenzenesulfonate, 7 parts of dextrin and 5 parts of titanium oxide were pulverized and mixed using an air mill. It was then added into a rotary or fluid bed mixer and sprayed with water to granulate. When most of the granules reached 1.00 mm to 0.15 mm, the granules were taken out, dried with a blast drier, and sieved. Pulverize the oversized material with a jet mill, 1.00-0.15m
m of granules were obtained.

【０７６４】[0764]

【製剤例５】（水性懸濁液）前記実施例１０５の化合物（Ｇ１．５５番）２５部、ナ
トリウムジオクチルスルホサクシネート０．７部、リグ
ニンスルホン酸カルシウム塩１０部、水４４．１５部及
びプロピレングリコール１０．１５部を固形粒子が５ミ
クロン以下の直径に減少されるまで、ボールミル、サン
ドミル又はローラーミル中で一緒に混合・粉砕した。こ
の粉砕スラリー９０部に、０．０５％（Ｗ／Ｗ）キサン
タンガム水溶液１０部を加えて混合し、水性懸濁液を得
た。Formulation Example 5 (Aqueous suspension) 25 parts of the compound of Example 105 (No. G1.55), 0.7 parts of sodium dioctyl sulfosuccinate, 10 parts of calcium ligninsulfonate, 44.15 parts of water, 10.15 parts of propylene glycol were mixed and milled together in a ball mill, sand mill or roller mill until the solid particles were reduced to a diameter of 5 microns or less. To 90 parts of this ground slurry, 10 parts of a 0.05% (W / W) xanthan gum aqueous solution was added and mixed to obtain an aqueous suspension.

【０７６５】[0765]

【発明の効果】本発明の化合物は、殺草作用を有してお
り、水田、畑地、果樹園、牧草地、芝生地、森林又は非
農耕地の除草剤として使用することができる。The compound of the present invention has a herbicidal action and can be used as a herbicide for paddy fields, uplands, orchards, pastures, turf, forests or non-agricultural lands.

【０７６６】本発明の化合物は、畑作の茎葉処理及び土
壌処理において問題となる種々の雑草に対して、除草活
性を示す。The compounds of the present invention exhibit herbicidal activity against various weeds which are problematic in foliar treatment and soil treatment of upland crops.

【０７６７】又、本発明の化合物は、水田において問題
となる種々の雑草、例えば、タイヌビエのようなイネ科
雑草；コナギ、アゼナ、キカシグサ、ミゾハコベ、のよ
うな広葉雑草；タマガヤツリ、ホタルイ、マツバイ、ミ
ズガヤツリのようなカヤツリグサ科雑草に対して除草活
性を示し、かつ、イネに対しては問題となる薬害を示さ
ない。The compound of the present invention can be used for various weeds which are problematic in paddy fields, for example, grass weeds such as Rubiea; broadleaf weeds such as oak, azaena, stag beetle, mizohacobe; It shows herbicidal activity against Cyperaceae weeds such as Cyperus serrata and does not show any problematic phytotoxicity against rice.

【０７６８】特に、水田において、雑草の発芽前又は発
芽後に湛水土壌処理することにより、水田の強雑草であ
るタイヌビエ、ヒメタイヌビエ、ケイヌビエ等のイネ科
雑草を強力に防除することができる。一方、水稲に対し
ては、選択性が大きく、移植水稲は薬害を受けることが
ないため、処理適用幅が大きいという利点がある。In particular, by treating the paddy field with flooded soil before or after germination of the weeds, it is possible to strongly control grass weeds, such as the strong weeds of the paddy field, such as the rice breeder, the royal barnyardgrass, and the canine fly. On the other hand, there is an advantage in that the selectivity to rice is high, and transplanted rice is not harmed by transplantation.

【０７６９】更に、畑地、水田のみならず、果樹園、桑
畑、非農耕地においても使用することができる。Further, it can be used not only in fields and paddy fields, but also in orchards, mulberry fields, and non-agricultural lands.

【０７７０】本発明の化合物の処理方法としては、通常
製剤化して、雑草の発芽前又は出芽後約１ヶ月以内に土
壌処理、茎葉処理又は湛水処理する。土壌処理には、土
壌表面処理、土壌混和処理等があり、茎葉処理には、植
物体の上方からの処理のほか、作物に付着しないように
雑草に限って処理する極部処理等があり、湛水処理に
は、粒剤やフロアブル剤の散布や水面への潅注処理等が
ある。As a method for treating the compound of the present invention, it is generally formulated into a formulation and subjected to soil treatment, foliage treatment or flooding before weed emergence or within about one month after emergence. Soil treatment includes soil surface treatment, soil admixture treatment, and the like, and foliage treatment includes, in addition to treatment from above the plant, extreme treatment that treats only weeds so that they do not adhere to crops. The flooding treatment includes spraying of granules and flowables and irrigation treatment on the water surface.

【０７７１】次に、生物試験例を挙げて、具体的にその
効果を示す。Next, the effects will be specifically described with reference to biological test examples.

【０７７２】[0772]

[Test example]

【０７７３】[0773]

【試験例１】水田雑草発芽前処理１００ｃｍ² ポットに水田土壌を充填し、休眠覚醒した
タイヌビエの種子を表層１ｃｍに混和した。また、２葉
期の水稲の苗を移植して湛水状態とし、温室で生育させ
た。３日後に、製剤例１に準じて調製した水和剤を用い
て所定の薬量を湛水土壌処理し、２１日後に次に示す判
定基準に従って調査を行なった。その結果を表９に示し
た。Test Example 1 Paddy field weed pre-emergence treatment A 100 cm ² pot was filled with paddy field soil, and the seeds of a sleepy and awakened foxtail were mixed with 1 cm of the surface layer. In addition, seedlings of paddy rice at the 2 leaf stage were transplanted into a flooded state and grown in a greenhouse. Three days later, the soil was treated with a prescribed amount of a flooded soil using a wettable powder prepared according to Formulation Example 1, and 21 days later, an investigation was performed according to the following criteria. Table 9 shows the results.

【０７７４】（判定基準）０：生育抑制率０〜１０％１：生育抑制率１１〜３０％２：生育抑制率３１〜５０％３：生育抑制率５１〜７０％４：生育抑制率７１〜９０％５：生育抑制率９１〜１００％(Judgment criteria) 0: Growth inhibition rate 0-10% 1: Growth inhibition rate 11-30% 2: Growth inhibition rate 31-50% 3: Growth inhibition rate 51-70% 4: Growth inhibition rate 71-71 90% 5: Growth inhibition rate 91-100%

【０７７５】[0775]

【表９】 [Table 9]

【０７７６】[0776]

【試験例２】タイヌビエ２．５葉期処理試験例１と同じ方法で、タイヌビエの２．５葉期に、製
剤例１に準じて調製した水和剤を用いて所定の薬量を湛
水処理し、２１日後に調査を行なった。その結果を表１
０に示した（判定基準は試験例１と同じ）。[Test Example 2] Treatment with 2.5-leaf stage of T. brasiliensis In the same manner as in Test Example 1, flooded with a predetermined amount of water using the wettable powder prepared according to Formulation Example 1 in the 2.5-leaf stage of T. brasiliensis. The treatment was performed and a survey was performed 21 days later. Table 1 shows the results.
0 (the criteria were the same as in Test Example 1).

【０７７７】[0777]

【表１０】 ─────────────────────────────── 化合物番号薬量（ｇ／ａ）タイヌビエ２．５葉期処理タイヌビエ水稲 ─────────────────────────────── A1.1 10 5 0 5 5 0 A1.5 10 5 0 5 5 0 A1.6 10 5 0 5 5 0 A1.9 10 5 0 5 4 0 C1.1 10 5 0 5 5 0 C1.5 10 5 0 5 5 0 C1.6 10 5 0 5 5 0 C2.1 10 5 0 5 4 0 C8.1 10 5 0 5 4 0 C9.3 10 5 0 5 5 0 C9.4 10 5 0 5 5 0 C9.6 10 5 0 5 4 0 C9.23 10 5 0 5 4 0 C9.39 10 5 0 5 5 0 C9.40 10 5 0 5 5 0 C9.55 10 5 0 5 4 0 C9.56 10 4 0 5 4 0 C11.1 10 5 0 5 4 0 D1.47 10 5 0 5 5 0 D1.68 10 5 0 5 5 0 D1.70 10 5 0 5 5 0 D1.72 10 5 0 5 5 0 D1.76 10 5 0 5 5 0 D1.81 10 5 0 5 5 0 D1.90 10 5 0 5 4 0 D2.11 10 5 0 5 4 0 D2.20 10 5 0 5 5 0 D2.26 10 5 0 5 5 0 D2.40 10 5 0 5 5 0 E1.18 10 5 0 5 4 0 F1.1 10 5 0 5 5 0 F1.21 10 5 0 5 4 0 F3.20 10 5 0 5 5 0 F3.22 10 5 0 5 5 0 F4.11 10 5 0 5 4 0 F4.12 10 5 0 5 5 0 F4.14 10 5 0 5 5 0 F4.30 10 5 0 5 5 0 F4.33 10 5 0 5 5 0 F4.43 10 5 0 5 4 0 F4.63 10 5 0 5 4 0 F7.56 10 5 0 5 5 0 G1.3 10 5 0 5 5 0 G1.6 10 5 0 5 4 0 G1.8 10 5 0 5 5 0 G1.34 10 5 0 5 5 0 G1.39 10 5 0 5 5 0 G1.50 10 5 0 5 5 0 G1.52 10 5 0 5 5 0 G1.55 10 5 0 5 5 0 G1.57 10 5 0 5 5 0 G1.59 10 5 0 5 5 0 G1.60 10 5 0 5 5 0 G1.62 10 5 0 5 5 0 G1.63 10 5 0 5 5 0 G1.64 10 5 0 5 5 0 G1.69 10 5 0 5 5 0 G2.5 10 5 0 5 4 0 G2.42 10 5 0 5 5 0 G5.33 10 5 0 5 5 0 G5.38 10 5 0 5 5 0 G6.31 10 5 0 5 5 0 H4.91 10 5 0 5 4 0 ──────────────────────────────────── 比較化合物Ａ 10 0 0 比較化合物Ａ 5 0 0 比較化合物Ｂ 10 2 0 比較化合物Ｂ 5 1 0 ──────────────────────────────────── 上記表中、比較化合物Ａは、米国特許４４２３２３７
に、化合物番号１番として記載されており、また、比較
化合物Ｂは、特開昭５８−５２２８０号公報に、化合物
番号３番として記載されている、それぞれ下記式で表さ
れる化合物である。TABLE 10 ─────────────────────────────── Compound No. drug content (g / a) barnyardgrass 2.5 leaf stage Treated rice millet paddy rice ─────────────────────────────── A1.1 10 5 0 5 5 0 A1.5 10 5 0 5 5 0 A1.6 10 5 0 5 5 0 A1.9 10 5 0 5 4 0 C1.1 10 5 0 5 5 0 C1.5 10 5 0 5 5 0 C1.6 10 5 0 5 5 0 C2.1 10 5 0 5 4 0 C8.1 10 5 0 5 4 0 C9.3 10 5 0 5 5 0 C9.4 10 5 0 5 5 0 C9.6 10 5 0 5 4 0 C9.23 10 5 0 5 4 0 C9.39 10 5 0 5 5 0 C9.40 10 5 0 5 5 0 C9.55 10 5 0 5 4 0 C9.56 10 4 0 5 4 0 C11.1 10 5 0 5 4 0 D1.47 10 5 0 5 5 0 D1.68 10 5 0 5 5 0 D1.70 10 5 0 5 5 0 D1.72 10 5 0 5 5 0 D1.76 10 5 0 5 5 0 D1.81 10 5 0 5 5 0 D1.90 10 5 0 5 4 0 D2.11 10 5 0 5 4 0 D2.20 10 5 0 5 5 0 D2.26 10 5 0 5 5 0 D2.40 10 5 0 5 5 0 E1.18 10 5 0 5 4 0 F1.1 10 5 0 5 5 0 F1.21 10 5 0 5 4 0 F3.20 10 5 0 5 5 0 F3.22 10 5 0 5 5 0 F4.11 10 5 0 5 4 0 F4 .12 10 5 0 5 5 0 F4.14 10 5 0 5 5 0 F4.30 10 5 0 5 5 0 F4.33 10 5 0 5 5 0 F4.43 10 5 0 5 4 0 F4.63 10 5 0 5 4 0 F7.56 10 5 0 5 5 0 G1.3 10 5 0 5 5 0 G1 .6 10 5 0 5 4 0 G1.8 10 5 0 5 5 0 G1.34 10 5 0 5 5 0 G1.39 10 5 0 5 5 0 G1.50 10 5 0 5 5 0 G1.52 10 5 0 5 5 0 G1.55 10 5 0 5 5 0 G1.57 10 5 0 5 5 0 G1.59 10 5 0 5 5 0 G1.60 10 5 0 5 5 0 G1.62 10 5 0 5 5 0 G1. 63 10 5 0 5 5 0 G1.64 10 5 0 5 5 0 G1.69 10 5 0 5 5 0 G2.5 10 5 0 5 4 0 G2.42 10 5 0 5 5 0 G5.33 10 5 0 5 5 0 G5.38 10 5 0 5 5 0 G6.31 10 5 0 5 5 0 H4.91 10 5 0 5 4 0 ───────────────────── ─────────────── Comparative compound A 100 000 Comparative compound A 500 比較 Comparative compound B 102 Comparative compound B 510 ─────────── 、 In the above table, Comparative Compound A is described in US Pat. No. 4,423,237.
And Compound No. 1 and Comparative Compound B is a compound represented by the following formula and described as Compound No. 3 in JP-A-58-52280.

【０７７８】[0778]

【化１５】 Embedded image

───────────────────────────────────────────────────── フロントページの続き (72)発明者佐藤一雄滋賀県野洲郡野洲町野洲1041 三共株式会社内 (72)発明者本間豊邦滋賀県野洲郡野洲町野洲1041 三共株式会社内 (72)発明者門谷淳二滋賀県野洲郡野洲町野洲1041 三共株式会社内 (72)発明者小井清滋賀県野洲郡野洲町野洲1041 三共株式会社内 (72)発明者伊藤充滋賀県野洲郡野洲町野洲1041 三共株式会社内 ──────────────────────────────────────────────────続き Continuing on the front page (72) Inventor Kazuo Sato 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture In-house (72) Inventor Toyokuni Homma 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture Sankyo Co., Ltd. (72) Inventor Junji Kadoya 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture In-house (72) Inventor Kiyoshi Koi 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture In-house (72) Inventor Mitsuru Ito 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture Sankyo Stock Association

Claims

[Claims]

1. A compound represented by the following general formula (I):[Wherein, R¹ Is a C1-C6 alkyl group (the alkyl group is a C1-C6
Substituted by an alkoxy group or 1 to 4 halogen atoms
C3 to C6 cycloalkyl group, C1 to C6 alkoxy group (the alkoxy group is 1 to
May be substituted by four halogen atoms) or C1
To C6 alkylthio group (the alkylthio group is 1 to
Which may be substituted by four halogen atoms),
R^Two Is a hydrogen atom, a C1-C6 alkyl group (the alkyl group is a hydroxyl group or
C3 to C6 cycloalkyl group, C2 to C6 alkenyl group (the alkenyl group may be 1 to 4
A C2 to C6 alkynyl group (the alkynyl group may be substituted with 1 to 4 halogen atoms).
May be substituted by four halogen atoms) or a formula-
YR⁷ R represents a group represented by^Three Is a C1-C6 alkyl group (the alkyl group is a C1-C6
Substituted by an alkoxy group or 1 to 4 halogen atoms
C3 to C6 cycloalkyl group, C1 to C6 alkoxy group (the alkoxy group is 1 to
A C2 to C6 alkenyl group (the alkenyl group may be substituted with 1 to 4 halogen atoms).
A C2 to C6 alkynyl group (the alkynyl group may be substituted with 1 to 4 halogen atoms).
May be substituted by 4 halogen atoms), a halogen atom, a nitro group or a formula -COR⁸ R represents a group represented by^Four Passing
And R^Five Is the same or different and represents a hydrogen atom or a C1-C6 alkyl group;⁶ Is a C1-C6 alkyl group (the alkyl group is a C1-C6
Substituted by an alkoxy group or 1 to 4 halogen atoms
C3 to C6 cycloalkyl group, C1 to C6 alkoxy group (the alkoxy group is 1 to
A C2 to C6 alkenyl group (the alkenyl group may be substituted with 1 to 4 halogen atoms).
A C2 to C6 alkynyl group (the alkynyl group may be substituted with 1 to 4 halogen atoms).
May be substituted by 4 halogen atoms), a halogen atom, a nitro group or a formula -COR⁸ R represents a group represented by⁷
Is a C1-C6 alkyl group (the alkyl group is a C1-C6
Alkoxy group, C1-C6 alkylthio group or 1-4
C3 to C6 cycloalkyl groups, C2 to C6 alkenyl groups (the alkenyl groups may be 1 to 3
A C2 to C6 alkynyl group (the alkynyl group may be substituted with 1 to 4 halogen atoms).
A C6 to C14 aryl group (the aryl group may be substituted with 1 to 3
C1 to C6 alkyl groups, 1 to 3 C1 to C6
Substituted by a alkoxy group or 1 to 4 halogen atoms
C7-C11 aralkyl groups (the aralkyl groups may be
May be substituted by up to four halogen atoms) or
At least one oxygen, sulfur or nitrogen atom
A heterocyclic group having 4 to 10 ring atoms (the heterocyclic group is
The groups are 1 to 3 C1 to C6 alkyl groups, 1 to 3
C1 to C6 alkoxy group or 1 to 4 halogen atoms
And may be fused with a benzene ring
), R⁸ Is a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group or a C1-C6 alkoxy
A represents an oxygen atom or a sulfur atom, X represents an oxygen atom or a sulfur atom, and Y represents a formula -CO-, a formula-
COO-, formula -CH_Two O-, formula -CH_Two S-, formula -CH
_Two CH_Two O-, formula -CH_Two CH_Two S-, formula -CH_Two CO
-, Formula -CH_Two COO-, formula -CH (CH_Three ) COO
-, Formula -CH_Two CH_Two CO-, formula -CH_Two OCO-, formula
-CH_Two OCOO- or formula -CH_Two CH_Two Table with OCO-
Q represents an oxygen atom or a sulfur atom, m represents 0, 1, 2, 3 or 4 (where m is 2, 3 or 4
In the case of, each R^Three Can be the same or different
N) represents 0, 1, 2, 3 or 4 (where n is 2, 3 or 4)
In the case of, each R⁶ Can be the same or different
No). Aniline derivatives and herbicides represented by
Those salts that are acceptable.

Wherein R ¹ is, C1 -C6 alkyl group (the alkyl group, C1 -C6
An alkoxy group or 1 to 4 halogen atoms may be substituted), a C3 to C6 cycloalkyl group or a C1 to C6 alkoxy group (the alkoxy group may be substituted by 1 to 4 halogen atoms) The compound of claim 1, wherein

3. R ¹ is a C1-C6 alkyl group (the alkyl group is a C1-C6 alkyl group).
The compound according to claim 1, which is an alkoxy group, which may be substituted by 1 to 4 halogen atoms) or a C1 to C6 alkoxy group.

Wherein R ¹ is, C1 to C3 alkyl group (the alkyl group, C1 to C3
May be substituted by an alkoxy group) or C1-C3
The compound according to claim 1, which is an alkoxy group.

(5) R ¹ is a methyl group or a methoxy group,
A compound according to claim 1.

6. The compound according to claim 1, wherein R ¹ is a methoxy group.

7. R ² is a hydrogen atom, C1 -C6 alkyl group (the alkyl group may be substituted by hydroxyl or 1 to 4 halogen atoms), C3 -C6 cycloalkyl group or the formula -YR 7. The compound according to claim 1, which is a group represented by ⁷ .

Is 8. R ^2, a hydrogen atom, C1 -C6 alkyl group (the alkyl group may be substituted by a hydroxyl group) or a group represented by the formula -YR ^7, in claim 1 to 6 A compound as described.

9. A compound according to claim 9, wherein R ² is a hydrogen atom, a C1-C3 alkyl group substituted by a hydroxyl group, or a compound of the formula
Is a group represented by YR ^7, The compound according to claim 1 to 6.

10. The compound according to claim 1, wherein R ² is a hydrogen atom, a hydroxymethyl group or a group represented by the formula —YR ⁷ .

11. The compound according to claim 1, wherein R ² is a hydrogen atom.

12. Y is a group represented by the formula -CO-, the formula -COO-, the formula-
CH ₂ O-, wherein -CH _₂ CH ₂ O-, wherein -CH ₂ CO
-, formula -CH ₂ COO-, formula -CH ₂ CH ₂ CO-, wherein -CH ₂ OCO-, wherein -CH ₂ -OCOO- or formula -CH ₂
_2. A group represented by CH ₂ OCO—.
The compound according to 0.

13. Y is a group represented by the formula -CO-, the formula -COO-, the formula-
CH ₂ O-, wherein -CH _₂ CH ₂ O-, wherein -CH ₂ OCO
- or a group represented by formula -CH ₂ -OCOO-, compounds of claim 1 to 10.

14. Y is a group represented by the formula -CO-, the formula -COO-, the formula-
CH ₂ O-, wherein -CH ₂ OCO- or formula -CH ₂ OCO
The compound according to any one of claims 1 to 10, which is a group represented by O-.

15. The method according to claim 1, wherein Y is a group represented by the formula —CO—, —COO— or —CH ₂ OCO—.
The compound according to 0.

16. R ⁷ is a C1 to C6 alkyl group (the alkyl group may be substituted by a C1 to C6 alkoxy group or 1 to 4 halogen atoms), a C3 to C6 cycloalkyl group, a C2 to C6 alkyl group. A C6 alkenyl group (the alkenyl group may be substituted with 1 to 4 halogen atoms), a C2 to C6 alkynyl group (the alkynyl group may be substituted with 1 to 4 halogen atoms), C6-C14 aryl group (the aryl group is 1 to 3
C1 to C6 alkyl groups, 1 to 3 C1 to C6 alkoxy groups or 1 to 4 halogen atoms), C7 to C11 aralkyl groups (the aralkyl groups may be 1 to 4 A heterocyclic group containing at least one oxygen atom, sulfur atom or nitrogen atom and having 4 to 10 ring atoms (the heterocyclic group may be a C1-C6 alkyl group, a C1 The compound according to any one of claims 1 to 10 or 12 to 15, which may be substituted with a C6 alkoxy group or 1 to 4 halogen atoms, or may be condensed with a benzene ring.

17. The method according to claim 1, wherein R ⁷ is a C1 to C6 alkyl group (the alkyl group may be substituted by a C1 to C6 alkoxy group or 1 to 4 halogen atoms). Item 16. The compound according to any one of Items 12 to 15.

18. The method according to claim 1, wherein R ⁷ is a C1 to C3 alkyl group (the alkyl group may be substituted by 1 to 4 halogen atoms). Compound.

(19) the compound according to the above (1) to (10) or (12) to (15), wherein R ⁷ is an ethyl group or a 2,2,2-trichloroethyl group;

20. R ³ is a C1 to C6 alkyl group (the alkyl group is a C1 to C6
An alkoxy group or a substituted with 1 to 4 halogen atoms), a C3-C6 cycloalkyl group a C1-C6 alkoxy group (the alkoxy group may be substituted with 1 to 4 halogen atoms), halogen atom, a group represented by the nitro group, or the formula -COR ^8, a compound of claim 1 to 19.

21. When R ³ is a C1-C6 alkyl group (the alkyl group is a C1-C6
An alkoxy group or a C1 to C6 alkoxy group (the alkoxy group may be substituted with 1 to 4 halogen atoms) or a halogen atom. Item 20. The compound according to any one of Items 1 to 19.

22. The compound according to claim 1, wherein R ³ is a C1-C3 alkyl group, a C1-C3 alkoxy group or a halogen atom.

23. The compound according to claim 1, wherein R ³ is a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom or a chlorine atom.

24. The compound according to claim 1, wherein R ³ is a methyl group.

25. The compound according to claim 1, wherein R ⁴ and R ⁵ are the same or different and each is a hydrogen atom or a methyl group.

(26) R ⁴ is a hydrogen atom or a methyl group;
25. The compound according to claim 1, wherein ⁵ is a hydrogen atom.

27. The compound according to claim 1, wherein R ⁴ and R ⁵ are a hydrogen atom.

28. A method wherein R ⁶ is a C1-C6 alkyl group (the alkyl group is a C1-C6
An alkoxy group or may be substituted by 1 to 4 halogen atoms), a C3-C6 cycloalkyl group, a C1-C6 alkoxy group (the alkoxy group may be substituted by 1 to 4 halogen atoms) , a group represented by halogen atom or formula -COR ^8, a compound of claim 1 to 27.

29. R ⁶ is, C1 -C6 alkyl group (the alkyl group may be substituted by 1 to 4 halogen atoms), C1 -C6 alkoxy group (said alkoxy group is 1 to 4 28) or a halogen atom.

30. The compound according to claim 1, wherein R ⁶ is a C1-C3 alkyl group, a C1-C3 alkoxy group or a halogen atom.

31. The compound according to claim 1, wherein R ⁶ is a methoxy group, a fluorine atom or a chlorine atom.

32. R ⁶ is a fluorine atom or a chlorine atom,
28. The compound according to claim 1.

33. R ⁸ is a C1-C3 alkyl group or C1
The compound according to claim 1, wherein the compound is a C 3 alkoxy group.

34. The compound according to any one of claims 1 to 20 or 25 to 28, wherein R ⁸ is a C1-C3 alkoxy group.

35. The compound according to any one of claims 1 to 20 or 25 to 28, wherein R ⁸ is a methoxy group.

36. The method according to claim 1, wherein A is an oxygen atom.
5. The compound according to 5.

37. The method according to claim 1, wherein X is an oxygen atom.
7. The compound according to 6.

38. The method according to claim 1, wherein Q is a sulfur atom.
8. The compound according to 7.

39. The compound according to claim 1, wherein m is 0, 1, 2, or 3.

40. The method according to claim 1, wherein m is 0 or 1.
9. The compound according to 8.

41. The compound according to any one of claims 1 to 27 or 33 to 38, wherein m is 0.

42. The compound according to claim 1, wherein n is 0, 1, 2, or 3.

43. The compound according to claim 1, wherein n is 0, 1 or 2.

44. The method according to claim 1, wherein n is 0 or 1.
2. The compound according to 1.

45. The compound according to claim 1, wherein n is 1.

46. N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] acetamide, N- [4- (benzoxazol-2-ylmethoxy)
-2-methylphenyl] acetamide, methyl N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] carbamate, methyl N- [4- (benzoxazol-2-ylmethoxy) -2-methylphenyl] Carbamate, methyl N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] -N-hydroxymethylcarbamate, methyl N- [4- (benzothiazol-2-ylmethoxy) -2-methylphenyl] -N-propionyloxymethyl carbamate, N- [4- (benzothiazol-2-ylmethoxy)-
2-methylphenyl] -N-methoxycarbonylpropionamide, methyl N- [4- (6-methoxybenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamate, methyl N- [4- (5-fluorobenzothiazole-
2-ylmethoxy) -2-methylphenyl] carbamate, methyl N- [4- (6-fluorobenzothiazole-
The compound according to claim 1, which is selected from 2-ylmethoxy) -2-methylphenyl] carbamate.