JP2002068977A - Prophylactic and therapeutic agent for diabetes containing 2-mercaptocarboxylic acid derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new 2-mercaptocarboxylic acid derivative, and to provide a hypoglycemic and a hypolipidemic agents comprising the derivating. SOLUTION: The objective prophylactic or therapeutic agent for diabetes comprises a 2-mercaptocarboxylic acid drivative represented by formula (1) (wherein A is phenyl, or the like; X is a direct bond, or the like; W and Y are each independently an alkylene, or the like; and R is H, or the like), or a pharmacologically permissible ester thereof or a pharmacologically permissible salt thereof.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel 2-mercaptocarboxylic acid derivative, a pharmacologically acceptable ester thereof or a pharmacologically acceptable salt thereof, and thiazolidine-2 used as a synthetic intermediate thereof. , 4-dione derivatives.

[0002] The present invention also provides an excellent insulin resistance improving action, hypoglycemic action, lipid lowering action, anti-inflammatory action,
2-mercaptocarboxylic acid derivative or pharmaceutically acceptable ester thereof or pharmaceutically acceptable salt thereof having immunomodulatory action, lipid peroxide production inhibitory action, PPAR activating action, and synthetic intermediate thereof It relates to the thiazolidine-2,4-dione derivative used.

Further, the present invention relates to the above-mentioned 2-mercaptocarboxylic acid derivatives, pharmacologically acceptable esters thereof or pharmacologically acceptable salts thereof, and thiazolidine-2,4-use used as a synthetic intermediate thereof. Diabetes, hyperlipidemia, obesity, impaired glucose tolerance, fatty liver, diabetic complications (for example, retinopathy, nephropathy, neuropathy, coronary artery disease, etc.) and arteriosclerosis containing a dione derivative as an active ingredient. Disease, cardiovascular disease (eg, ischemic heart disease, etc.), atherosclerosis or cell damage caused by ischemic heart disease (eg, brain damage caused by stroke, etc.) A prophylactic and / or therapeutic agent (preferably diabetes or high) for an inflammatory disease (eg, osteoarthritis, pain, fever, rheumatoid arthritis, inflammatory bowel disease, autoimmune disease, pancreatitis, etc.). A prophylactic and / or therapeutic agent for lipemia).

Further, the present invention provides a prophylactic or therapeutic agent for the above-mentioned diseases containing the above-mentioned compound as an active ingredient, a composition for preventing or treating the above-mentioned diseases containing the above-mentioned compound as an active ingredient, and a method for preventing or treating the above-mentioned diseases. The present invention relates to a method of preventing or treating the above-mentioned diseases, wherein the compound is used for producing a medicament for treatment, or a pharmacologically effective amount of the compound is administered to a warm-blooded animal (preferably a human).

[0005]

2. Description of the Related Art Conventionally, biguanide compounds and sulfonylurea compounds have been used as therapeutic agents for diabetes. However, biguanide compounds are rarely used at present because they cause acidosis. In addition, sulfonylurea-based compounds have potent hypoglycemic effect, but often cause severe hypoglycemia, and thus require careful use. Therefore, a therapeutic agent for diabetes having few side effects has been desired.

[0006] The present inventors have focused on 2-mercaptocarboxylic acid derivatives to search for a remedy for diabetes that does not have such disadvantages, and have made intensive studies. For the 2-mercaptocarboxylic acid derivatives, for example, the following compounds and their pharmacological actions have been reported. (1) J. Biol. Chem., 260 (12), pp.7337-7342 (1985)
Describes that 2-mercaptopropionic acid exhibits a weak fatty acid oxidation inhibitory action. (2) According to Am. J. Physiol., 250, pp. 1003-1006 (1986), when mercaptoacetic acid was administered intraperitoneally to rats, there was no change in the blood glucose level of rats 1 hour after administration. It has been reported. (3) Eur. J. Clin. Pharmacol., 31, pp. 119-121 (19
86) states that 2-mercaptopropionic acid is a metabolite of thiola but has no noticeable effect. (4) Physiol. Behav., 57 (4), pp. 759-764 (1995), describes that intravenous administration of mercaptoacetic acid in rats increases blood glucose levels in rats 1 hour after administration. Have been. (5) J. Med. Chem., 39 (20), pp. 3897-3907 (1996) describes that α-alkylthioether carboxylic acids have a blood glucose lowering effect. (6) Japanese Patent Application Laid-Open No. 6-65024 discloses a method of using a thioether carboxylic acid derivative as a cosmetic composition for topical application to skin, hair, and nails, particularly to skin. (7) J. Org. Chem., 50 (19), pp.3676-3678 (1985),
And (8) Int. J. Cosmet. Sci., 15 (4), pp. 163-173 (199
3) also describes that thioether carboxylic acid was used as a skin active agent.

However, the literatures (1) to (8) do not describe the 2-mercaptocarboxylic acid derivative which is the compound of the present invention. There is no description in the literature of using the above compounds as hypoglycemic or lipid lowering agents.

[0008] (9) WO92 / 17435 describes that a thioether carboxylic acid derivative is useful as a therapeutic agent for diabetes, early diabetes, especially adult-onset diabetes. (10) JP-A-63-174948 discloses that thioether carboxylic acid derivatives are useful as therapeutic agents for diabetes, prediabetes, in particular, allogeneic diabetes and lipid metabolism disorders, and have a triglyceride and cholesterol level lowering action. There is a statement to the effect. (11) WO 98/28254 describes that thioether propionic acid derivatives have hypoglycemic and lipid lowering effects. (12) WO 96/19466 describes that thiolcarboxylic acid derivatives are useful as intermediates for synthesizing rhodanine derivatives and as therapeutic agents for inflammatory bowel disease. (13) JP-T 5-507920 discloses that thioether carboxylic acid derivatives are useful as hypoglycemic agents. (14) JP-T-Hei 7-505647 describes that alkylthiocarboxylic acids are useful as therapeutic agents for type II diabetes.

However, the references (9) to (14) disclose relatively short-chain carboxylic acid derivatives having 3 or less carbon atoms, such as 2-substituted propionic acid, and 2-arylthio or 2-alkylthiocarboxylic acid derivatives. There is no description of a relatively long-chain carboxylic acid derivative having a mercapto group at position 2 which is a compound of the present invention. In the production of the novel 2-mercaptocarboxylic acid derivative of the present invention, a method involving a thiazolidinedione compound as a synthetic intermediate is mainly employed.

The thiazolidinedione compound is, for example, (1
5) WO97 / 47612, (16) JP-A-8-104
688, (17) JP-A-9-100280, (18) JP-A-9-136877, (19) JP-A-10-18246
1, (20) JP-A-9-176163, (21) JP-A-9-25273, (22) JP-A-9-235284, (2)
3) JP-A-8-157473, (24) JP-A-8-208
648, (25) JP-A-7-173158, (26) JP-A-6-247945, (27) JP-A-7-30985
2, (28) JP-A-6-9629, (29) JP-A 5-2
13913, (30) JP-A-1-272574, (3)
1) JP-A-1-272573, (32) JP-A-64-13
088, (33) JP-A-63-230689, (34)
JP-A-64-56675, (35) JP-A-59-4847
1, (36) JP-A-58-118577, (37) JP-A-56-97277, (38) JP-A-55-64586,
(39) JP-A-55-22636, (40) WO98 /
42691.

[0011]

SUMMARY OF THE INVENTION The inventors of the present invention have conducted experiments for many years to search for compounds having various physiological activities, and as a result, have found that 2-mercaptocarboxylic acid derivatives having a novel structure or derivatives thereof. Pharmacologically acceptable esters or pharmacologically acceptable salts thereof, and thiazolidine-2,4-dione derivative used as a synthetic intermediate thereof have excellent insulin resistance improving effect, hypoglycemic effect, and lipid lowering. The present invention was found to have an action, an anti-inflammatory action, an immunoregulatory action, a lipid peroxide production inhibitory action, and a PPAR activating action, and completed the present invention.

Another object of the present invention is to provide the above-mentioned 2-mercaptocarboxylic acid derivative, a pharmaceutically acceptable ester thereof or a pharmaceutically acceptable salt thereof, and thiazolidine-2 used as a synthetic intermediate thereof. Diabetes, hyperlipidemia, obesity, impaired glucose tolerance, fatty liver, diabetic complications (eg, retinopathy, nephropathy, neuropathy, coronary artery disease, etc.) containing a 4-dione derivative as an active ingredient. Atherosclerosis, cardiovascular disease (eg, ischemic heart disease, etc.), cell damage caused by atherosclerosis or ischemic heart disease (eg, brain damage caused by stroke, etc.) And inflammatory diseases (eg, osteoarthritis, pain, fever, rheumatoid arthritis, inflammatory bowel disease, autoimmune disease, pancreatitis, etc.) and preventive agents for diabetes (particularly diabetes and hyperlipidemia) and the like. / Or cure It is to provide an agent.

[0013]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, the compound of the present invention represented by the following general formula (I) has excellent blood glucose lowering action and lipid lowering action. The present invention has been completed.

That is, the present invention provides a compound represented by the general formula (I)

[0015]

Embedded image Wherein A is a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents α described below) or a heteroaromatic group (having 1 to 3 substituents α which will be described later) May be shown).

X is a bond, an oxygen atom, a sulfur atom, or -N
Represents an H-group.

W and Y are each independently a bond or
Represents a C ₁ -C ₂₀ alkylene group.

However, the -WXY- group does not show a methylene group.

R represents a hydrogen atom, a C ₁ -C ₆ alkanoyl group, or a C ₇ -C ₁₁ arylaminocarbonyl group (the aryl may have 1 to 3 substituents β described later on the aryl). .

The substituent α is (i) a C ₁ -C ₂₀ alkyl group (which may have 1 to 3 substituents β described later), and (ii) C _2-.
A C ₂₀ unsaturated hydrocarbon group (which may have 1 to 3 substituents β described later), (iii) a C ₁ -C ₁₀ alkoxy group, (iv) a halogen atom, (v) a hydroxyl group, vi) a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents β described below), and (vii) a monocyclic heteroaromatic group (1 to 3 substituents β described later). (Viii) a C ₇ -C ₁₆ aralkyl group (which may have 1 to 3 substituents β described later on the aryl,
The alkyl may have one hydroxyl group as a substituent. ), (Ix) a C ₇ -C ₁₆ arylcarbonylalkyl group (which may have 1 to 3 substituents β described later on the aryl), and (x) a C ₆ -C ₁₀ aryloxy group (described later) Substituting β
May be provided. ), (Xi) a C ₄ -C ₁₂ cycloalkylalkyloxy group, (xii) a C ₇ -C ₁₆ aralkyloxy group (which may have 1 to 3 substituents β described later on the aryl, A hydroxyl group as a substituent
You may have one. ), (Xiii) C ₇ -C ₁₆ arylcarbonylalkyloxy group (substituted β
May be provided. ), (Xiv) a monocyclic heteroaromatic ring C ₁ -C ₆ alkyloxy group (the monocyclic heteroaromatic ring may have 1 to 3 substituents β described later, May have one hydroxyl group.),
(xv) a monocyclic heteroaromatic ring C ₁ -C ₆ carbonylalkyloxy group (substituent β described later on monocyclic heteroaromatic ring is 1 to 3
You may have one. _{), (Xvi) C 7 -C} 16 aryloxyalkyl group (which may have 1 to 3 of substituents β described later on the _{aryl.), (Xvii) C 8} -C 2 2 aralkyloxy group (Substituent β described later on aryl is 1 to 3
You may have one. ) Or (xviii) represents a C ₂ -C ₁₁ carboxyalkoxy group.

The substitution β is (i) a C ₁ -C ₆ alkyl group, (ii) C ₁
-C ₆ alkoxy group, (iii) C ₁ -C ₆ alkylthio group, (iv) halogen atom, (v) C ₁ -C ₄ alkylenedioxy group, (vi) nitro group, (vii) cyano group, (viii ) C ₁ -C ₆ alkanoyl group, (i
x) represents a carbamoyl group, (x) a C ₂ -C ₇ alkoxycarbonylamino group, or (xi) a phenyl group. Or a pharmacologically acceptable ester thereof, or a pharmacologically acceptable salt thereof.

Further, the present invention relates to 2-
The present invention relates to a mercaptocarboxylic acid derivative, a pharmacologically acceptable ester thereof, a pharmacologically acceptable salt thereof, a synthetic intermediate thereof, and a use thereof. In the specification of the present application, “aryl” refers to a monovalent group generated by removing one hydrogen atom bonded to a ring of an aromatic hydrocarbon.

The term "heteroaromatic ring" refers to a monocyclic or polycyclic aromatic heterocyclic group having 1 to 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur. Say.

The term "alkylene" refers to a divalent group formed by losing two hydrogen atoms from carbon atoms of a linear or branched aliphatic hydrocarbon.

"Alkanoyl group" refers to an aliphatic carboxylic acid
(Including formic acid) means a monovalent group generated by removing an OH group from the group.

"Arylaminocarbonyl" refers to a monovalent group in which a hydrogen atom on the nitrogen atom of carbamoyl (H ₂ NCO-) is substituted by the above-mentioned aryl.

The term "alkyl" refers to a monovalent group formed by the loss of one hydrogen atom from a linear or branched aliphatic hydrocarbon.

The term "unsaturated hydrocarbon group" refers to a hydrocarbon group containing a linear or branched carbon-carbon unsaturated bond (> C = C <, -C≡C-).

The "alkoxy group" refers to a monovalent group formed by losing a hydrogen atom of a hydroxyl group of a linear or branched alcohol.

"Monocyclic heteroaromatic group" refers to a 5- or 6-membered monocyclic aromatic group having 1 to 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur. Having a heterocyclic group.

"Aralkyl" refers to a monovalent group in which one hydrogen atom of the aforementioned alkyl group has been substituted with the aforementioned aryl group.

"Aralkylcarbonyl" refers to a monovalent group in which the terminal carbon of the alkyl portion of aralkyl is substituted by an oxo group.

"Aryloxy" refers to a monovalent group in which an oxygen atom is bonded to the above-mentioned aryl.

The term "cycloalkylalkyloxy" refers to a monovalent group in which one hydrogen atom of the above-mentioned alkyl group is substituted by a 3- to 6-membered cycloalkyl, and an oxygen atom is bonded to a terminal carbon of the alkyl portion.

The term "aralkyloxy" refers to a group in which an oxygen atom is bonded to the terminal carbon of the alkyl portion of the aralkyl.
A valence group.

"Arylcarbonylalkyloxy" is a monovalent group in which the carbon atom closest to the aryl portion of the alkyl portion of the aralkyl is substituted with an oxo group, and an oxygen atom is bonded to the terminal carbon of the alkyl portion. Say.

"Arylcarbonylalkyloxy" refers to a monovalent group in which the carbon atom closest to the aryl part of the alkyl part of aralkyloxy is substituted by an oxo group.

"Monocyclic heteroaromatic alkyloxy"
A monovalent group in which one hydrogen atom of the aforementioned alkyl group is substituted by the aforementioned monocyclic heteroaromatic ring, and an oxygen atom is further bonded to the terminal carbon of the alkyl portion.

The term "monocyclic heteroaromatic carbonylalkyloxy" refers to the monocyclic heteroaromatic ring alkyloxy having the closest carbon atom to the monocyclic heteroaromatic ring among the carbon atoms in the alkyl portion of the alkyloxy moiety substituted with an oxo group. Monovalent group.

"Aryloxyalkyl" refers to a monovalent group in which one hydrogen atom of the above-mentioned alkyl group is substituted by the above-mentioned aryloxy.

"Aralkyloxyalkyl" means a monovalent group in which one hydrogen atom of the above-mentioned alkyl has been substituted by the above-mentioned aralkyloxy.

“Carboxyalkoxy” refers to a monovalent group in which one hydrogen atom of the above-mentioned alkoxy has been replaced by carboxyl (—COOH).

The "alkylthio group" is a monovalent group formed by losing a sulfur atom of a thiol group of a linear or branched thiol.

The term "alkylenedioxy group" refers to a divalent group in which both ends of a linear or branched alkylene are substituted with oxygen atoms.

"Alkoxycarbonylamino" refers to a monovalent group in which the carbonyl carbon of carbonylamino (-CONH-) is substituted with alkoxy.

“C _m -C _n ” means that it has m to n carbon atoms. For example, “C ₁ -C ₆ carbonylalkyl” refers to carbonylalkyl having 1 to 6 carbon atoms, that is, carbonyl or carbonyl has 1 to 5 carbon atoms.
Refers to a group to which a linear or branched alkyl having a single bond is bonded. A is a C ₆ -C ₁₀ aryl group (substituted α
May be provided. ) Indicates `` C _6-
“C ₁₀ ” and “aryl” are as defined above,
“It may have 1 to 3 substitution α” means “substitution α
Or 1 to 3 identical or different substituents α. As the aryl moiety,
For example, phenyl or naphthyl can be mentioned, and phenyl is preferable.

A is a heteroaromatic group (substituent α described below is 1
It may have three to three. ), "Heteroaromatic ring" and "may have 1 to 3 substituents α" are the same as those described above. Examples of the heteroaromatic ring moiety include monocyclic heteroaromatic groups such as thienyl, furyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, pyridyl, pyridazinyl, pyrimidinyl, or pyrazinyl; or benzofuryl, isobenzofuryl, 2,3 -Such as dihydrobenzofuryl, chromenil, xanthenyl, phenoxathiinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, carbolinyl, acridinyl or condensinyl Heteroaromatic ring groups can be mentioned, preferably a monocyclic heteroaromatic group, and more preferably a monocyclic heteroaromatic ring having one or two heteroatoms. Group, most preferably thienyl, furyl, thiazolyl, pyridyl, or benzofuranyl.

When W and Y each independently represent a C ₁ -C ₂₀ alkylene group, “C ₁ -C ₂₀ ” and “alkylene” have the same meanings as described above. Examples of the C ₁ -C ₂₀ alkylene group include methylene, methylmethylene, ethylene, propylene, trimethylene, tetramethylene, methyltrimethylene, methylpropylene, dimethylethylene, pentamethylene, methyltetramethylene, dimethyltrimethylene, hexamethylene, Methylpentamethylene, dimethyltetramethylene, heptamethylene, methylhexamethylene, ethylpentamethylene, octamethylene, methylheptamethylene, ethylhexamethylene, methylpentamethylene, nonamethylene, methyloctamethylene, ethylheptamethylene, decamethylene, methylnonamethylene,
Ethyl octamethylene, diethylhexamethylene, undecamethylene, methyldecamethylene, ethylnonamethylene, dimethylnonamethylene, propyloctamethylene,
Dodecamethylene, methylundecamethylene, ethyldecamethylene, propylnonamethylene, diethyloctamethylene, tridecamethylene, methyldodecamethylene, ethylundecamethylene, propyldecamethylene, pentyloctamethylene, tetradecamethylene, methyltridecamethylene, Ethyl dodecamethylene, propylundecamethylene, butyldecamethylene, pentylnonamethylene,
Pentadecamethylene, methyltetradecamethylene, ethyltridecamethylene, propyldodecamethylene, pentyldecamethylene, hexadecamethylene, methylpentadecamethylene, ethyltetradecamethylene, propyltridecamethylene, butyldodecamethylene, heptadecamethylene, methyl Hexadecamethylene, ethylpentadecamethylene, propyltetradecamethylene, pentyldodecamethylene, octadecamethylene, methylheptadecamethylene, propylpentadecamethylene, nonadecamethylene, methyloctadecamethylene, ethylheptadecamethylene, eicosamethylene, methyl nonadecamethylene or there may be mentioned ethyl octadecamethylene, preferably a C ₁ -C ₁₅ alkylene group, more preferably a C ₁ -C ₁₀ alkylene group, It is preferably in a C ₁ -C ₈ alkylene group, and most preferably from C ₁ -C ₆ alkylene group. Further, among the linear alkylene group and the branched alkylene group, a linear alkylene group is preferable.

When R represents a C ₁ -C ₆ alkanoyl group, “C ₁
“-C ₆ ” and “alkanoyl group” have the same meaning as described above. Examples of the C ₁ -C ₆ alkanoyl group include formyl, acetyl, propionyl, butyryl, isobutyryl, s-butyryl, t-butyryl, and pentenoyl, and preferably a C ₂ -C ₅ alkanoyl group. And more preferably a C ₂ -C ₃ alkanoyl group, most preferably acetyl.

R is a C ₇ -C ₁₁ arylaminocarbonyl group
(The aryl may have 1 to 3 substituents β described later on the aryl.), “C ₇ -C ₁₁ ” and “arylaminocarbonyl” have the same meanings as described above, and “ Substitution β
"May have 1 to 3 substituent (s)" means that the compound does not have the substituent β or has 1 to 3 substituent (s) the same or different. The arylaminocarbonyl moiety includes, for example, phenylaminocarbonyl or naphthylaminocarbonyl, and is preferably phenylaminocarbonyl.

When the substituent α represents a C ₁ -C ₂₀ alkyl group (which may have 1 to 3 substituents β described later),
“C ₁ -C ₂₀ ”, “alkyl” and “may have 1 to 3 substituents β” are the same as those described above. C _1-
The C ₂₀ alkyl moieties, such as methyl, ethyl, propyl, isopropyl, butyl, s- butyl, t- butyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, or eicosyl can be exemplified, preferably a C ₁ -C ₁₀ alkyl groups, more preferably the
C ₁ -C ₆ alkyl group, more preferably a C ₁ -C ₄ alkyl group, and most preferably from C ₁ -C ₂ alkyl group.

When the substituent α represents a C ₂ -C ₂₀ unsaturated hydrocarbon group (which may have 1 to 3 substituents β described later), “C ₂ -C ₂₀ ”, The terms "saturated hydrocarbon group" and "may have 1 to 3 substituents β" are the same as those described above. Examples of the C ₂ -C ₂₀ unsaturated hydrocarbon moiety include, for example, ethenyl, ethynyl, propenyl, methylpropenyl, ethylpropenyl, propynyl, butenyl, methylbutenyl, ethylbutenyl, butynyl, pentenyl, methylpentenyl, pentynyl, hexenyl, isohexenyl, heptenyl , Octenyl, nonenyl, decenyl,
Undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, linolyl, linolenyl, nonadecenyl, or eicosenyl can be mentioned, preferably a C ₂ -C ₁₀ unsaturated hydrocarbon having one double bond. a group, further preferably a C ₂ -C ₆ unsaturated hydrocarbon group having one double bond, C ₂ having one double bond and optimally
-C _{4 is} an unsaturated hydrocarbon group.

When the substituted α represents a C ₁ -C ₁₀ alkoxy group, “C ₁ -C ₁₀ ” and “alkoxy group” have the same meanings as described above. As the C ₁ -C ₁₀ alkoxy group, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentoxy, isopentoxy, methylbutoxy, neopentoxy, hexyloxy, methylpentoxy, methyl dimethyl Butoxy, heptyloxy, octyloxy, nonyloxy, or decyloxy can be mentioned, preferably C ₁
-C ₈ alkoxy, more preferably C ₁ -C ₆ alkoxy, more preferably C ₁ -C ₄ alkoxy, and most preferably C ₁ -C ₂ alkoxy.

When the substituted α represents a halogen atom, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. And more preferably a fluorine atom or a chlorine atom, and most preferably a chlorine atom.

When the substituent α represents a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents β described later),
“C ₆ -C ₁₀ ”, “aryl” and “may have 1 to 3 substituents β” are the same as those described above. C _6-
The C ₁₀ aryl moiety can include, for example, phenyl or naphthyl, preferably phenyl.

When the substituent α represents a monocyclic heteroaromatic ring group (which may have 1 to 3 substituents β described later), “monocyclic heteroaromatic group” and “substituent "may have 1 to 3 β""is the same as the above. Examples of the monocyclic heteroaromatic ring moiety include, for example, thienyl, furyl, pyrrolyl, thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, furazanyl, pyrazolyl,
Oxopyrazolyl, triazolyl, triazolonyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl,
Examples thereof include pyrazinyl and triazinyl, preferably a monocyclic heteroaromatic group having one or two heteroatoms, and most preferably thienyl, furyl, pyrrolyl, oxazolyl, or pyridyl.

The substituent α is a C ₇ -C ₁₆ aralkyl group (the aryl may have 1 to 3 substituents β described later,
The alkyl may have one hydroxyl group as a substituent. ), “C ₇ -C ₁₆ ”, “aralkyl” and “may have 1 to 3 substituents β” are the same as those described above, and “a hydroxyl group is 1 as a substituent. "May have one hydroxyl group" means that it does not have a hydroxyl group or has one hydroxyl group as a substituent. As the aralkyl moiety, for example, benzyl, naphthylmethyl, phenethyl,
Naphthylethyl, phenylpropyl, naphthyl-propyl, phenylbutyl, naphthylbutyl, phenylpentyl, can be exemplified naphthylpentyl, phenyl hexyl, or naphthyl hexyl, preferably a phenylalkyl group having C ₁ -C ₆ alkyl, More preferably C ₁
A phenylalkyl group having -C ₂ alkyl.

When the substitution α is a C ₇ -C ₁₆ aralkylcarbonyl group
(It may have 1 to 3 substituents β described later on the aryl.) In the case of “C ₇ -C ₁₆ ”, “aralkylcarbonyl” and “1 to 3 substituents β May be used "has the same meaning as described above. Examples of the aralkylcarbonyl moiety include, for example, benzoyl, benzylcarbonyl, phenethylcarbonyl, 3-phenylpropylcarbonyl, 5-phenylpentylcarbonyl, naphthylcarbonyl, naphthylmethylcarbonyl, or 3-naphthylpropylcarbonyl, preferably Phenyl
A C ₁ -C ₆ alkylcarbonyl group, more preferably a phenyl C ₁ -C ₄ alkylcarbonyl group, most preferably benzoyl or benzylcarbonyl.

When the substituent α represents a C ₆ -C ₁₀ aryloxy group (which may have 1 to 3 substituents β described later), “C ₆ -C ₁₀ ”, “aryloxy” And "substitution β
And may have three or more "are the same as those described above. Examples of the C ₆ -C ₁₀ aryloxy moiety include phenoxy, or naphthyloxy,
Preferably it is phenoxy.

When the substituted α represents a C ₄ -C ₁₂ cycloalkylalkyloxy group, “C ₄ -C ₁₂ ” and “cycloalkylalkyloxy” have the same meanings as described above. The C ₄ -
The C ₁₂ cycloalkylalkyl group, for example, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexyl methoxy, cyclopropyl-ethoxy, cyclobutyl-ethoxy, cyclopentyl-ethoxy, cyclohexyl-ethoxy, cyclobutyl propoxy, cyclohexyl propoxy, cyclohexyl butoxy, or Cyclohexylhexyloxy can be mentioned, preferably a C ₅ -C ₁₂ cycloalkylalkyloxy group, more preferably a C ₆ -C ₁₀ cycloalkylalkyloxy group, and most preferably a C ₆ -C ₈ It is a cycloalkylalkyloxy group.

When the substituent α is a C ₇ -C ₁₆ aralkyloxy group (the aryl may have 1 to 3 substituents β to be described later, and the alkyl may have 1 hydroxyl group as a substituent on the alkyl. ), “C ₇ -C ₁₆ ”, “aralkyloxy”, “may have 1 to 3 substituents β”, and “C ₇ -C ₁₆ ” may have 1 to 3 substituents β. "May be the same as described above. Examples of the aralkyloxy moiety include, for example, benzyloxy, phenethyloxy, phenylpropoxy, phenylbutoxy, phenylpentoxy, phenylhexyloxy, naphthylmethoxy, naphthylethoxy, naphthylpropoxy, naphthylbutoxy, naphthylpentoxy, or naphthylhexyloxy. It is preferably a phenyl C ₁ -C ₆ alkyloxy group, more preferably a phenyl C ₁ -C ₄ alkyloxy group, most preferably a phenyl C ₁ -C ₂ alkyloxy group.

When the substituent α represents a C ₇ -C ₁₆ arylcarbonylalkyloxy group (which may have 1 to 3 substituents β described later on the aryl), “C ₇ -C ₁₆ ” , "Arylcarbonylalkyloxy" and "may have 1 to 3 substituents β" are as defined above. The arylcarbonylalkyloxy moiety can include, for example, benzoyloxy, phenacyloxy, 3-phenyl-3-oxopropoxy, or 4-phenyl-4-oxobutoxy, preferably phenyl C ₁ -C ₆
A carbonylalkyloxy group, more preferably a phenyl C ₁ -C ₄ carbonylalkyloxy group, most preferably benzoyloxy or phenacyloxy.

The substituent α is a monocyclic heteroaromatic ring C ₁ -C ₆ alkyloxy group (the monocyclic heteroaromatic ring may have 1 to 3 substituents β described later, May have one hydroxyl group as the substituent)), "monocyclic heteroaromatic alkyloxy", "C ₁ -C ₆ ", and 1
"It may have from 3 to 3" and "It may have one hydroxyl group as a substituent" have the same meaning as described above. As the monocyclic heteroaromatic ring C ₁ -C ₆ alkyloxy moiety, for example, pyridylmethoxy, pyridylethoxy,
Pyridylpropoxy, pyridylbutoxy, pyridylpentoxy, pyridylhexyloxy, pyrimidinylmethoxy, pyrimidinylethoxy, pyrimidinylpropoxy,
Pyrimidinyl butoxy, pyrimidinyl pentoxy, thienyl methoxy, thienyl ethoxy, thienyl propoxy, thienyl butoxy, thienyl pentoxy, furyl methoxy, furyl butoxy, thiazolyl methoxy, thiazolyl butoxy, oxazolyl methoxy, oxazolyl ethoxy, oxa Zolylbutoxy, isoxazolylmethoxy, isoxazolylethoxy, isoxazolylpropoxy, or isoxazolylbutoxy,
It is preferably a monocyclic heteroaromatic ring C ₁ -C ₆ alkyloxy group having one or two heteroatoms, and more preferably a monocyclic heteroaromatic ring C ₁ -C having one or two heteroatoms.
_{4 is} an alkyloxy group, more preferably a monocyclic heteroaromatic C ₁ -C ₂ alkyloxy group having one hetero atom, most preferably pyridylmethoxy, pyrimidinylmethoxy, thienylmethoxy, furylmethoxy, thia Zolylmethoxy, oxazolylmethoxy, pyridylethoxy, or thienylethoxy.

The substituent α has a monocyclic heteroaromatic ring C ₁ -C ₆ carbonylalkyloxy group (the monocyclic heteroaromatic ring may have 1 to 3 substituents β described later). When indicated, "monocyclic heteroaromatic carbonylalkyloxy", "C
₁ -C ₆ "and the term" may have 1 to 3 of substituents β "is synonymous with those described above. As the monocyclic heteroaromatic carbonylalkyloxy moiety, for example, pyridylcarbonyloxy, 2-pyridyl-2-oxoethoxy, 3-
Pyridyl-3-oxopropoxy, 4-pyridyl-4-oxobutoxy, 5-pyridyl-5-oxopentoxy, 6-pyridyl-
6-oxohexyloxy, pyrimidinylcarbonyloxy, 2-pyrimidinyl-2-oxoethoxy, 3-pyrimidinyl-3-oxopropoxy, 4-pyrimidinyl-4-oxobutoxy, 5-pyrimidinyl-5-oxopentoxy, thienylcarbonyloxy , 2-thienyl-2-oxoethoxy, 3-
Thienyl-3-oxopropoxy, 4-thienyl-4-oxobutoxy, 5-thienyl-5-oxopentoxy, furylcarbonyloxy, 4-furyl-4-oxobutoxy, thiazolylcarbonyloxy, 4-thiazolyl-4 -Oxobutoxy, oxazolylcarbonyloxy, 2-oxazolyl-2
-Oxoethoxy, 4-oxazolyl-4-oxobutoxy,
Isoxazolylcarbonyloxy, 2-isoxazolyl-2
-Oxoethoxy, 3-isoxazolyl-3-oxopropoxy, or 4-isoxazolyl-4-oxobutoxy, preferably a monocyclic heteroaromatic ring C ₁ -C ₆ having one or two heteroatoms. A carbonylalkyloxy group, more preferably a monocyclic heteroaromatic C ₁ -C ₄ carbonylalkyloxy group having one or two heteroatoms, more preferably a monocyclic heteroaromatic ring having one heteroatom A heteroaromatic ring C ₁ -C ₂ carbonylalkyloxy group, most preferably pyridylcarbonyloxy, 2-pyridyl-2-oxoethoxy, pyrimidinylcarbonyloxy, thienylcarbonyloxy, 2-thienyl-2-oxoethoxy, furylcarbonyl Oxy, thiazolylcarbonyloxy,
Or oxazolylcarbonyloxy.

When the substituent α represents a C ₇ -C ₁₆ aryloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), “C ₇ -C ₁₆ ”, “Aryloxyalkyl” and “may have 1 to 3 substituents β” are the same as those described above. As the C ₇ -C ₁₆ aryloxyalkyl moiety, for example, phenoxymethyl, naphthyloxymethyl, phenoxy-1-ethyl, phenoxy-2-ethyl, naphthyloxyethyl, phenoxybutyl, naphthyloxybutyl, phenoxyhexyl, or naphthyloxy Hexyl can be mentioned,
Preferably a phenoxy C ₁ -C ₆ alkyl group, more preferably a phenoxy C ₁ -C ₄ alkyl group, more preferably a phenoxy C ₁ -C ₂ alkyl group, most preferably phenoxymethyl, Or 1-phenoxyethyl.

When the substituent α represents a C ₈ -C ₂₂ aralkyloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), “C ₈ -C ₂₂ ”, “Aralkyloxyalkyl” and “may have 1 to 3 substituents β” are the same as those described above. As the C ₈ -C ₂₂ aralkyloxyalkyl moiety, for example, benzyloxymethyl, benzyloxyethyl, phenethyloxymethyl, phenethyloxyethyl, naphthylmethyloxymethyl, naphthylmethyloxyethyl, naphthylethyloxymethyl, naphthylethyloxyethyl, Benzyloxybutyl, naphthylmethyloxybutyl, benzyloxyhexyl, or naphthylmethyloxyhexyl can be mentioned, preferably a phenyl C ₁ -C ₆ alkyloxy C ₁ -C ₆ alkyl group, more preferably phenyl C
₁ -C is ₄ alkyloxy C ₁ -C ₄ alkyl group, a phenyl C ₁ -C ₂ more and more preferably has two independently a C ₁ -C ₂ alkyl alkyloxy C ₁ -C ₂ alkyl group And
More preferably, it is benzyloxymethyl or 1- (benzyloxy) ethyl, most preferably benzyloxymethyl.

When the substituted α represents a C ₂ -C ₁₁ carboxyalkoxy group, “C ₂ -C ₁₁ ” and “carboxyalkoxy” have the same meanings as described above. Examples of the C ₂ -C ₁₁ carboxyalkoxy group, for example carboxymethoxy, carboxyethoxy, carboxy propoxy, carboxymethyl butoxy, carboxy pentoxy, carboxymethyl hexyloxy, carboxymethyl heptyloxy, carboxymethyl octyloxy, carboxymethyl nonyl oxy, or carboxy decyloxy It is preferably a C ₂ -C ₅ carboxyalkoxy group, more preferably a C ₂ -C ₃ carboxyalkoxy group, and most preferably a carboxymethoxy group.

When the substituent β represents a C ₁ -C ₆ alkyl group,
“C ₁ -C ₆ ” and “alkyl” refer to C ₁ -C ₂₀ alkyl having 1 to 6 carbon atoms. Examples of the C ₁ -C ₆ alkyl group include the same groups as those having 1 to 6 carbon atoms of the alkyl group described in the definition of the substituent α, preferably a C ₁ -C ₄ alkyl group. And more preferably a C ₁ -C ₂ alkyl group.

When the substituent β represents a C ₁ -C ₆ alkoxy group, the above-mentioned C ₁ -C ₁₀ alkoxy has 1 to 6 carbon atoms. The C ₁ -C ₆ alkoxy group has a substituent α
The same groups as those having 1 to 6 carbon atoms in the alkyl group described in the definition can be mentioned, preferably a C ₁ -C ₄ alkoxy group, more preferably a C ₁ -C ₂ alkoxy group. is there.

When the substituent β represents a C ₁ -C ₆ alkylthio group, “C ₁ -C ₆ ” and “alkylthio group” have the same meanings as described above. Examples of the alkylthio group include methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, s-butylthio, t-
Butylthio, pentylthio, isopentylthio, methylbutylthio, neopentylthio, hexylthio, or dimethylbutylthio, and preferably C ₁ -C ₄
An alkylthio group, more preferably a C ₁ -C ₂ alkylthio group.

When the substituent β represents a halogen atom, examples of the halogen atom include the same atoms as the halogen atom described in the definition of the substituent α, preferably a fluorine atom, a chlorine atom or a bromine atom. And more preferably a fluorine atom or a chlorine atom, and most preferably a chlorine atom.

When the substituent β represents a C ₁ -C ₄ alkylenedioxy group, “C ₁ -C ₄ ” and “alkylenedioxy group” have the same meanings as described above. Examples of the C ₁ -C ₄ alkylenedioxy group include methylenedioxy, ethylidenedioxy, dimethylenedioxy, isopropylenedioxy, trimethylenedioxy, and tetramethylenedioxy, preferably C an ₁ -C ₂ alkylenedioxy group, more preferably a methylenedioxy.

When the substituent β represents a C ₁ -C ₆ alkanoyl group, “C ₁ -C ₆ ” and “alkanoyl group” have the same meanings as described above. Examples of the C ₁ -C ₆ alkanoyl group include the same groups as the alkanoyl groups described in the definition of R, preferably a C ₂ -C ₅ alkanoyl group, more preferably C ₂ -C ₃ An alkanoyl group, most preferably acetyl.

When the substituent β represents a C ₂ -C ₇ alkoxycarbonylamino group, “C ₁ -C ₆ ” and “alkoxy” have the same meanings as described above. Examples of the alkoxycarbonylamino group having the C ₁ -C ₆ alkoxy include methoxycarbonylamino, ethoxycarbonylamino, propoxycarbonylamino, isopropoxycarbonylamino, butoxycarbonylamino, isobutoxycarbonylamino, s-butoxycarbonylamino, t -Butoxycarbonylamino, pentoxycarbonylamino, isopentoxycarbonylamino, methylbutoxycarbonylamino, neopentoxycarbonylamino, hexyloxycarbonylamino, or dimethylbutoxycarbonylamino, preferably C ₂ -C ₅ alkoxycarbonylamino group, more preferably C ₂ -C ₃
It is an alkoxycarbonylamino group.

Therefore, when R represents a C ₇ -C ₁₁ arylaminocarbonyl group (which may have 1 to 3 substituents β on the aryl), the group having the substituent β includes: For example, methylphenylaminocarbonyl, dimethylphenylaminocarbonyl, ethylphenylaminocarbonyl, t-butylphenylaminocarbonyl, methoxyphenylaminocarbonyl, ethoxyphenylaminocarbonyl, methylthiophenylaminocarbonyl, ethylthiophenylaminocarbonyl, fluorophenylaminocarbonyl, difluoro Phenylaminocarbonyl, chlorophenylaminocarbonyl, dichlorophenylaminocarbonyl, bromophenylaminocarbonyl, methylenedioxyphenylaminocarbonyl, nitrophenylaminocarboni , Cyanophenylaminocarbonyl, acetylphenylaminocarbonyl, carbamoylphenylaminocarbonyl, t-butoxycarbamoylphenylaminocarbonyl, methylnaphthylaminocarbonyl, methoxynaphthylaminocarbonyl, methylthionaphthylaminocarbonyl, fluoronaphthylaminocarbonyl, chloronaphthylaminocarbonyl, methylene Dioxynaphthylaminocarbonyl, nitronaphthylaminocarbonyl, cyanonaphthylaminocarbonyl, acetylnaphthylaminocarbonyl, carbamoylnaphthylaminocarbonyl, or t-butoxycarbamoylnaphthylaminocarbonyl, preferably a phenylaminocarbonyl group (on aryl) May have 1 to 3 substituents β). It is suitably a phenylaminocarbonyl group (which may have one or two substituents β on the aryl), and most preferably a phenylaminocarbonyl group (which has one substituent β on the aryl). May be used.)

When the substituent α represents a C ₁ -C ₂₀ alkyl group (which may have 1 to 3 substituents β), the substituent β
As the group having, for example, methoxymethyl, methoxyethyl, methoxybutyl, methoxyoctyl, methoxyicosyl, methylthiomethyl, methylthiobutyl, fluoromethyl, fluorobutyl, fluorohexyl, chloromethyl, chlorobutyl, chlorohexyl, difluoromethyl, Trifluoromethyl, trifluoroethyl, nitromethyl, nitrobutyl, nitrohexyl,
Examples thereof include cyanomethyl, cyanobutyl, cyanohexyl, acetylmethyl, acetylbutyl, or acetylhexyl, preferably a C ₁ -C ₁₀ alkyl group (substituted β
May be provided. ), More preferably a C ₁ -C ₆ alkyl group (which may have 1 to 3 substituents β), and most preferably a C ₁ -C ₂ alkyl group (the substituent β 1 to 3).

When the substituted α represents a C ₂ -C ₂₀ unsaturated hydrocarbon group (which may have 1 to 3 substituted β), the group having the substituted β is, for example, methoxy Ethenyl, methoxybutenyl, methoxyoctenyl, methoxyeicocenyl, methylthiobutenyl, fluorobutenyl, fluorohexenyl, chlorobutenyl, chlorohexenyl, trifluoroethenyl, nitrobutenyl, nitrohexenyl, cyanobutenyl, cyanohexenyl, acetylbutenyl, Or acetylhexenyl, preferably a C ₂ -C ₁₀ unsaturated hydrocarbon group (which may have 1 to 3 substituents β), and more preferably 1 C ₂ -C ₁₀ unsaturated hydrocarbon group having double bond (the substituent β may have one.), and, C ₂ -C ₆ unsaturated with one double bond and optimally Hydrocarbon group (which may have one substituent minutes beta.) Is.

When the substituted α represents a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents β), the substituted β
Examples of the group having are, for example, methylphenyl, dimethylphenyl, ethylphenyl, t-butylphenyl, methoxyphenyl, ethoxyphenyl, methylthiophenyl, ethylthiophenyl, fluorophenyl, difluorophenyl, chlorophenyl, dichlorophenyl, bromophenyl, methylenediphenyl Oxyphenyl, nitrophenyl, cyanophenyl, acetylphenyl, carbamoylphenyl, t-butoxycarbamoylphenyl, methylnaphthyl, methoxynaphthyl, methylthionaphthyl, fluoronaphthyl, chloronaphthyl, methylenedioxynaphthyl, nitronaphthyl, cyanonaphthyl, acetylnaphthyl, carbamoyl naphthyl, or t- butoxy carbamoyl naphthyl can be mentioned, a suitably C ₆ -C ₁₀ aryl group (substituent beta 1 Properly it may have two.)
And more preferably a C ₆ -C ₁₀ aryl group (substituted β is 1
You may have one. ), And particularly preferably a phenyl group (which may have one substituent β).

When the substituted α is a monocyclic heteroaromatic group (substituted β
May be provided. )), As the group having a substituent β, for example, methylpyridyl, methoxypyridyl, methylthiopyridyl, fluoropyridyl, chloropyridyl, bromopyridyl, methylenedioxypyridyl, nitropyridyl, cyanopyridyl, acetylpyridyl, carbamoylpyridyl , Methylthienyl,
Methoxythienyl, methylthiothienyl, fluorothienyl, chlorothienyl, bromothienyl, methylenedioxythienyl, nitrothienyl, cyanothienyl, acetylthienyl, carbamoylthienyl, methylthiazolyl, methoxythiazolyl, methylthiothiazolyl, fluorothiazolyl, chlorothiazolyl , Bromothiazolyl, methylenedioxythiazolyl, nitrothiazolyl,
Cyanothiazolyl, acetylthiazolyl, carbamoylthiazolyl, phenylthiazolyl, methyloxazolyl, methoxyoxazolyl, methylthiooxazolyl,
Fluoroxazolyl, chlorooxazolyl, bromooxazolyl, methylenedioxyoxazolyl, nitrooxazolyl, cyanooxazolyl, acetyloxazolyl, or carbamoyloxazolyl, and preferably Is a monocyclic heteroaromatic group having one or two hetero atoms (which may have one to three substituents β), and more preferably one or two hetero atoms.
Monocyclic heteroaromatic group (substituted β is 1 or 2
You may have one. ), And most preferably a monocyclic heteroaromatic ring group having one or two heteroatoms (which may have one substituent β).

The substituent α may have 1 to 3 substituents β on the C ₇ -C ₁₆ aralkyl group (aryl, and may have one hydroxyl group as a substituent on alkyl. ), The substituent having a substituent β or a hydroxyl group includes, for example, methylbenzyl, methoxybenzyl, methylthiobenzyl, fluorobenzyl, chlorobenzyl, methylenedioxybenzyl, nitrobenzyl, cyanobenzyl, acetylbenzyl, carbamoylbenzyl, t-butoxycarbamoylbenzyl, methylnaphthylmethyl,
Methoxynaphthylmethyl, methylthionaphthylmethyl,
Fluoronaphthylmethyl, chloronaphthylmethyl, methylenedioxynaphthylmethyl, nitronaphthylmethyl,
Cyanonaphthylmethyl, acetylnaphthylmethyl, carbamoylnaphthylmethyl, t-butoxycarbamoylnaphthylmethyl, methyl-1-phenethyl, methyl-2-phenethyl, methylphenylbutyl, methoxyphenylbutyl,
Methylthiophenylbutyl, fluorophenylbutyl,
Chlorophenylbutyl, methylenedioxyphenylbutyl, nitrophenylbutyl, cyanophenylbutyl, acetylphenylbutyl, carbamoylphenylbutyl,
t-butoxycarbamoylphenylbutyl, phenyl (hydroxy) methyl, methylphenyl (hydroxy) methyl, methoxyphenyl (hydroxy) methyl, methylthiophenyl (hydroxy) methyl, fluorophenyl (hydroxy) methyl, chlorophenyl (hydroxy) methyl,
Methylenedioxyphenyl (hydroxy) methyl, nitrophenyl (hydroxy) methyl, cyanophenyl (hydroxy) methyl, acetylphenyl (hydroxy) methyl,
Carbamoylphenyl (hydroxy) methyl, t-butoxycarbamoylphenyl (hydroxy) methyl, naphthyl
(Hydroxy) methyl, methylnaphthyl (hydroxy) methyl, methoxynaphthyl (hydroxy) methyl, methylthionaphthyl (hydroxy) methyl, fluoronaphthyl (hydroxy) methyl, chloronaphthyl (hydroxy) methyl,
Methylenedioxynaphthyl (hydroxy) methyl, nitronaphthyl (hydroxy) methyl, cyanonaphthyl (hydroxy) methyl, acetylnaphthyl (hydroxy) methyl,
Carbamoylnaphthyl (hydroxy) methyl, t-butoxycarbamoylnaphthyl (hydroxy) methyl, phenyl
(Hydroxy) ethyl, methylphenyl (hydroxy) ethyl, methoxyphenyl (hydroxy) ethyl, methylthiophenyl (hydroxy) ethyl, fluorophenyl (hydroxy) ethyl, chlorophenyl (hydroxy) ethyl,
Methylenedioxyphenyl (hydroxy) ethyl, nitrophenyl (hydroxy) ethyl, cyanophenyl (hydroxy) ethyl, acetylphenyl (hydroxy) ethyl,
Carbamoylphenyl (hydroxy) ethyl or t-butoxycarbamoylphenyl (hydroxy) ethyl, preferably a C ₇ -C ₁₆ aralkyl group (even if it has one or two substituents β on the aryl) (Alternatively, the alkyl may have one hydroxyl group as a substituent.)
And more preferably a C ₇ -C ₁₆ aralkyl group (which may have one substituent β on the aryl and may have one hydroxyl group as a substituent on the alkyl). And more preferably a phenyl C ₁ -C ₆ alkyl group (which may have one substituent β on the phenyl or one hydroxyl group as a substituent on the alkyl). And most preferably a phenyl C ₁ -C ₄ alkyl group (which may have one substituent β on phenyl or one hydroxyl group as a substituent on alkyl). .

The substituted α is a C ₇ -C ₁₆ aralkylcarbonyl group
When (the aryl may have 1 to 3 substituents β on the aryl), the group having the substituent β includes:
For example, methylbenzoyl, methoxybenzoyl, methylthiobenzoyl, fluorobenzoyl, chlorobenzoyl, methylenedioxybenzoyl, nitrobenzoyl, cyanobenzoyl, acetylbenzoyl, carbamoylbenzoyl, t-butoxycarbamoylbenzoyl,
Methylbenzylcarbonyl, methoxybenzylcarbonyl, methylthiobenzylcarbonyl, fluorobenzylcarbonyl, chlorobenzylcarbonyl, methylenedioxybenzylcarbonyl, nitrobenzylcarbonyl,
Cyanobenzylcarbonyl, acetylbenzylcarbonyl, carbamoylbenzylcarbonyl, or t-butoxycarbamoylbenzylcarbonyl,
It is preferably a C ₇ -C ₁₆ aralkylcarbonyl group (which may have one or two substituents β on the aryl), and more preferably a C ₇ -C ₁₆ aralkylcarbonyl group (an aryl group on the aryl May have one substituent β)),
More preferably, it is a phenyl C ₁ -C ₆ alkylcarbonyl group (which may have one substituent β on phenyl),
Most preferably, it is a phenyl C ₁ -C ₄ alkylcarbonyl group (which may have one substituent β on phenyl).

When the substituent α represents a C ₆ -C ₁₀ aryloxy group (which may have 1 to 3 substituents β), the group having the substituent β includes, for example, methylphenoxy, Dimethylphenoxy, ethylphenoxy, t-butylphenoxy, methoxyphenoxy, ethoxyphenoxy, methylthiophenoxy, ethylthiophenoxy, fluorophenoxy, difluorophenoxy, chlorophenoxy, dichlorophenoxy, bromophenoxy, methylenedioxyphenoxy, nitrophenoxy, cyanophenoxy, Acetylphenoxy, carbamoylphenoxy, t-butoxycarbamoylphenoxy, methylnaphthyloxy, methoxynaphthyloxy, methylthionaphthyloxy, fluoronaphthyloxy, chloronaphthyloxy, methylenedioxyna Yloxy, nitro naphthyloxymethyl, cyano naphthyloxymethyl, there may be mentioned acetyl naphthyloxymethyl, carbamoyloxy naphthyloxymethyl, or t- butoxy carbamoyloxy naphthyloxymethyl, preferably a C ₆ -C ₁₀ aryloxy group (substituent β 1 or 2 And more preferably a C ₆ -C ₁₀ aryloxy group (which may have one substitution β), and most preferably a phenoxy group (substitution may have one β).

The substituent α is a C ₇ -C ₁₆ aralkyloxy group (the aryl may have 1 to 3 substituents β, or the alkyl may have 1 hydroxyl group as a substituent. ), The substituent having a substituent β or a hydroxyl group includes, for example, methylbenzyloxy, methoxybenzyloxy, methylthiobenzyloxy, 2-fluorobenzyloxy, 3-fluorobenzyloxy, 4-fluorobenzyloxy, chloro Benzyloxy, methylenedioxybenzyloxy, nitrobenzyloxy, cyanobenzyloxy, acetylbenzyloxy, carbamoylbenzyloxy, t-butoxycarbamoylbenzyloxy, methylnaphthylmethoxy, methoxynaphthylmethoxy, methylthionaphthylmethoxy, fluoronaphthylmethoxy, chloronaphthyl Methoxy, methylenedioxynaphthylmethoxy, nitronaphthylmethoxy, cyanonaphthylmethoxy, acetylnaphthylmethoxy, carbamoylnaphthylmethoxy, t-butoxycarbamoylnaphthylmethoxy, methylphenyl-1-ethoxy, methylphenyl-2-ethoxy, methylphenylbutoxy, methoxy Phenylbutoxy, methylthiophenylbutoxy, fluorophenylbutoxy, chlorophenylbutoxy, methylenedioxyphenylbutoxy, nitrophenylbutoxy, cyanophenylbutoxy, acetylphenylbutoxy, carbamoylphenylbutoxy, t-butoxycarbamoylphenylbutoxy, or phenyl (hydroxy)
Ethoxy may be mentioned, preferably a C ₇ -C ₁₆ aralkyloxy group (which may have one or two substituents β on the aryl, and one or more hydroxyl groups as the substituents on the alkyl.
You may have one. ), And more preferably a C ₇ -C ₁₆ aralkyloxy group (which may have one substituent β on the aryl or one hydroxyl group as a substituent on the alkyl. ), And more preferably a C ₇ -C ₁₄ aralkyloxy group (which may have one substituent β on the aryl, or one hydroxyl group as a substituent on the alkyl. ), And most preferably, a phenyl C ₁ -C ₄ alkyloxy group (the phenyl may have one substituent β, or the alkyl may have one hydroxyl group as a substituent. ).

When the substituent α represents a C ₇ -C ₁₆ arylcarbonylalkyloxy group (which may have 1 to 3 substituents β on the aryl), the group having the substituent β may be E.g., methylbenzoyloxy, methoxybenzoyloxy, methylthiobenzoyloxy, fluorobenzoyloxy, chlorobenzoyloxy, methylenedioxybenzoyloxy, nitrobenzoyloxy, cyanobenzoyloxy, acetylbenzoyloxy, carbamoylbenzoyloxy, tert-butoxycarbamoylbenzoyloxy , Methylnaphthylcarbonyloxy, methoxynaphthylcarbonyloxy, methylthionaphthylcarbonyloxy, fluoronaphthylcarbonyloxy, chloronaphthylcarbonyloxy, methylenedioxynaphthylcarbonyl Ruoxy, nitronaphthylcarbonyloxy, cyanonaphthylcarbonyloxy, acetylnaphthylcarbonyloxy, carbamoylnaphthylcarbonyloxy, t-butoxycarbamoylnaphthylcarbonyloxy, methylphenacyloxy, methoxyphenacyloxy, methylthiophenacyloxy, fluorophenacyloxy, Chlorophenacyloxy, methylenedioxyphenacyloxy, nitrophenacyloxy, cyanophenacyloxy, acetylphenacyloxy, carbamoylphenacyloxy, t-butoxycarbamoylphenacyloxy, 3-methylphenyl-3-oxopropoxy, 3-methoxyphenyl-3-oxopropoxy, 3-methylthiophenyl-3-oxopropoxy, 3-fluorophenyl-3-oxopropoxy, 3-chlorophenyl-3- Kisopuropokishi, 3-methylenedioxyphenyl -
3-oxopropoxy, 3-nitrophenyl-3-oxopropoxy, 3-cyanophenyl-3-oxopropoxy, 3-acetylphenyl-3-oxopropoxy, 3-carbamoylphenyl-3-oxopropoxy, or 3-t- Butoxycarbamoylphenyl-3-oxopropoxy can be mentioned. It is preferably a C ₇ -C ₁₆ arylcarbonylalkyloxy group (which may have one or two substituents β on the aryl), and more preferably a C ₇ -C ₁₆ arylcarbonylalkyloxy group (One substitution β on aryl
You may have one. ), More preferably a C ₇ -C ₁₄ arylcarbonylalkyloxy group (which may have one substituent β on the aryl), and most preferably phenyl C ₁ -C ₄ carbonylalkyl An oxy group (which may have one substituent β on phenyl).

The substituent α is a monocyclic heteroaromatic C ₁ -C ₆ alkyloxy group (substituent β is 1 to 3 on the monocyclic heteroaromatic ring)
And the alkyl may have one hydroxyl group as a substituent on the alkyl. )), As the group having a substituent β or a hydroxyl group, for example, methylpyridylmethoxy, phenylpyridylmethoxy, phenyl (methyl) pyridylmethoxy, 2-pyridyl-2-hydroxyethoxy, methylthienylmethoxy, phenyl Thienylmethoxy, phenyl (methyl) thienylmethoxy, 2-thienyl-2-hydroxyethoxy, methylthiazolylmethoxy, phenylthiazolylmethoxy, phenyl (methyl)
Thiazolylmethoxy, 2-thiazolyl-2-hydroxyethoxy, methyloxazolylmethoxy, phenyloxazolylmethoxy, phenyl (methyl) oxazolylethoxy, 2-oxazolyl-2-hydroxyethoxy, methylisoxazolylmethoxy Or dimethyl isoxazolyl methoxy, preferably a monocyclic heteroaromatic ring C ₁ -C ₆ alkyloxy group having one or two heteroatoms (substituted on the monocyclic heteroaromatic ring). may have 1 to 3 β, and may have one hydroxyl group as a substituent on the alkyl.), and more preferably a monocyclic heterocycle having 1 or 2 hetero atoms. Aromatic ring C ₁ -C ₆ alkyloxy group (monocyclic heteroaromatic ring may have one or two substituents β, and alkyl may have one hydroxyl group as a substituent on alkyl .)so Ri, monocyclic heteroaromatic ring C ₁ more preferably having 1 or 2 hetero atoms
A —C ₄ alkyloxy group (which may have one or two substituents β on a monocyclic heteroaromatic ring and one hydroxyl group as a substituent on alkyl). And more preferably a monocyclic heteroaromatic ring C ₁ -C ₂ alkyloxy group having one or two heteroatoms (which may have one or two substituents β on the monocyclic heteroaromatic ring. May have one hydroxyl group as a substituent on the alkyl)), and most preferably methylthienylmethoxy, 2-thienyl-2-
Hydroxyethoxy, phenylthiazolylmethoxy, or phenyl (methyl) oxazolylethoxy.

When the substituent α is a monocyclic heteroaromatic ring C ₁ -C ₆ carbonylalkyloxy group (substituted β on the monocyclic heteroaromatic ring)
May be provided. ), The group having a substituent β is, for example, methylpyridylcarbonyloxy, phenylpyridylcarbonyloxy, phenyl (methyl) pyridylcarbonyloxy, 2-
(Methylpyridyl) -2-oxoethoxy, methylthienylcarbonyloxy, phenylthienylcarbonyloxy, phenyl (methyl) thienylcarbonyloxy, 2-
(Methylthienyl) -2-oxoethoxy, methylthiazolylcarbonyloxy, phenylthiazolylcarbonyloxy, phenyl (methyl) thiazolylcarbonyloxy,
2- (methylthiazolyl) -2-oxoethoxy, methyloxazolylcarbonyloxy, phenyloxazolylcarbonyloxy, 2- [phenyl (methyl) oxazolyl] -2-
Oxoethoxy, 2-oxazolyl-2-oxoethoxy,
Methyl isoxazolyl carbonyloxy, or dimethyl isoxazolyl carbonyloxy,
Preferably, a monocyclic heteroaromatic C ₁ -C ₆ carbonylalkyloxy group having one or two heteroatoms (the monocyclic heteroaromatic ring may have 1 to 3 substituents β. ), More preferably a monocyclic heteroaromatic C ₁ -C ₆ carbonylalkyloxy group having one or two heteroatoms (having one or two substituents β on the monocyclic heteroaromatic ring) And more preferably a monocyclic heteroaromatic C ₁ -C ₄ carbonylalkyloxy group having 1 or 2 heteroatoms (substituted β is 1 on the monocyclic heteroaromatic ring). Or may have two.), And more preferably a monocyclic heteroaromatic ring C ₁ -C having one or two hetero atoms.
_{A 2-} carbonylalkyloxy group (which may have one or two substituents β on a monocyclic heteroaromatic ring);
Optimally, methylthienylcarbonyloxy, 2- (methylthienyl) -2-oxoethoxy, phenylthiazolylcarbonyloxy, or 2- [phenyl (methyl) oxazolyl]
2-oxoethoxy.

When the substituent α represents a C ₇ -C ₁₆ aryloxyalkyl group (which may have 1 to 3 substituents β on the aryl), the group having the substituent β includes:
For example, methylphenoxymethyl, dimethylphenoxymethyl, ethylphenoxymethyl, t-butylphenoxymethyl, methoxyphenoxymethyl, ethoxyphenoxymethyl, methylthiophenoxymethyl, ethylthiophenoxymethyl, fluorophenoxymethyl, difluorophenoxymethyl, chlorophenoxymethyl, dichloro Phenoxymethyl, bromophenoxymethyl, methylenedioxyphenoxymethyl, nitrophenoxymethyl, cyanophenoxymethyl, acetylphenoxymethyl, carbamoylphenoxymethyl, t-butoxycarbamoylphenoxymethyl, methylnaphthyloxymethyl, methoxynaphthyloxymethyl, methylthionaphthyloxymethyl , Fluoronaphthyloxymethyl, chloronaphthyloxymethyl , Methylenedioxynaphthyloxymethyl, nitronaphthyloxymethyl, cyanonaphthyloxymethyl, acetylnaphthyloxymethyl, carbamoylnaphthyloxymethyl, t-butoxycarbamoylnaphthyloxymethyl, methylphenoxybutyl,
Dimethylphenoxybutyl, ethylphenoxybutyl,
t-butylphenoxybutyl, methoxyphenoxybutyl, ethoxyphenoxybutyl, methylthiophenoxybutyl, ethylthiophenoxybutyl, fluorophenoxybutyl, difluorophenoxybutyl, chlorophenoxybutyl, dichlorophenoxybutyl, bromophenoxybutyl, methylenedioxyphenoxybutyl, nitro Phenoxybutyl, cyanophenoxybutyl, acetylphenoxybutyl, carbamoylphenoxybutyl, or t-butoxycarbamoylphenoxybutyl, preferably a C ₇ -C ₁₆ aryloxyalkyl group (substituted β on aryl is 1 or may have two.), and is further preferably a C ₇ -C ₁₆ aryloxyalkyl group (the substituent β on the aryl may have one.), further preferably C ₇ -C ₁₄ aryloxyalkyl group (which may have one substituent fraction β on the aryl.), And further preferably a phenoxy C ₁ -C ₄ alkyl group (substituent β on the phenyl And a phenoxy C ₁ -C ₂ alkyl group (which may have one substituent β on phenyl).

When the substituent α represents a C ₈ -C ₂₂ aralkyloxyalkyl group (which may have 1 to 3 substituents β on the aryl), the group having the substituent β includes: For example, methylbenzyloxymethyl, methylbenzyloxyethyl, methylnaphthylmethoxymethyl, methylbenzyloxybutyl, methylbenzyloxyhexyl, methylnaphthylmethoxyhexyl, methoxybenzyloxymethyl, methoxybenzyloxyethyl, methoxynaphthylmethoxymethyl, methoxybenzyloxybutyl , Methoxybenzyloxyhexyl, methoxynaphthylmethoxyhexyl, chlorobenzyloxymethyl, chlorobenzyloxyethyl, chloronaphthylmethoxymethyl, chlorobenzyloxybutyl, chlorobenzyloxyhexyl, or Lolo can be mentioned naphthyl methoxy hexyl, preferably a C ₈ -C ₂₂ aralkyloxy group (substituent β 1 or 2 on the aryl
You may have one. ), And more preferably a C ₈ -C ₂₂ aralkyloxyalkyl group (substituted β with 1
You may have one. ), And more preferably a C ₈ -C ₁₈ aralkyloxyalkyl group (substituted with 1
You may have one. ), And more preferably phenyl C
An ₁ -C ₄ alkyloxy C ₁ -C ₄ alkyl groups, most preferably phenyl C ₁ -C ₂ Rukiruokishi C ₁ -C ₂ alkyl group.

As described above, A is a C ₆ -C ₁₀ aryl group which may have 1 to 3 substituents α or 1 to 3 substituents α.
When a heteroaromatic group which may have one or more groups is shown, examples of the group include phenyl, methylphenyl, dimethylphenyl, ethylphenyl, butylphenyl, s-butylphenyl, t-butylphenyl, hexylphenyl, and propenylphenyl , (Methylpropenyl) phenyl, butenylphenyl, (methylbutenyl) phenyl, (trifluoromethyl) phenyl, (ditrifluoromethyl) phenyl, (pentafluoroethyl) phenyl, methoxyphenyl, dimethoxyphenyl, trimethoxyphenyl, ethoxyphenyl, Diethoxyphenyl, butoxyphenyl, hexyloxyphenyl, fluorophenyl, difluorophenyl, trifluorophenyl, chlorophenyl, dichlorophenyl, trichlorophenyl, bromophenyl, dibromophenyl, Phenyl, hydroxyphenyl, dihydroxyphenyl, biphenyl, pyridylphenyl, thienylphenyl, furylphenyl, pyrrolylphenyl, pyrimidylphenyl, benzylphenyl, (methylbenzyl) phenyl, (methoxybenzyl) phenyl, (fluorobenzyl) phenyl, ( (Chlorobenzyl) phenyl, phenethylphenyl, (methylphenethyl) phenyl, (methoxyphenethyl) phenyl, (fluorophenethyl) phenyl, (chlorophenethyl) phenyl, phenyl (hydroxy) methylphenyl, phenyl
(Hydroxy) ethylphenyl, (naphthylmethyl) phenyl, (naphthylethyl) phenyl, benzoylphenyl,
Phenoxyphenyl, (methylphenoxy) phenyl,
(Methoxyphenoxy) phenyl, (fluorophenoxy)
Phenyl, (chlorophenoxy) phenyl, (cyclopropylmethoxy) phenyl, (cyclopentylmethoxy) phenyl, (cyclohexylmethoxy) phenyl, benzyloxyphenyl, (methylbenzyloxy) phenyl,
(Methoxybenzyloxy) phenyl, (2-fluorobenzyloxy) phenyl, (3-fluorobenzyloxy) phenyl, (4-fluorobenzyloxy) phenyl, (chlorobenzyloxy) phenyl, (benzyloxy) (methyl) phenyl, 4-benzyloxy-2-fluorophenyl,
4-benzyloxy-3-fluorophenyl, 3-benzyloxy-2-fluorophenyl, 3-benzyloxy-4-fluorophenyl, 3-benzyloxy-5-fluorophenyl, 3
-Benzyloxy-6-fluorophenyl, (1-phenethyloxy) phenyl, (2-phenethyloxy) phenyl, (methyl-1-phenethyloxy) phenyl, (methyl-2-phenethyloxy) phenyl, (chlorophenethyloxy) Phenyl, (2-hydroxy-2-phenethyloxy) phenyl,
(Phenylpropyloxy) phenyl, (methylphenylpropyloxy) phenyl, (chlorophenylpropyloxy) phenyl, (phenacyloxy) phenyl, (3-phenyl-3-oxopropoxy) phenyl, (4-phenyl-4-
(Oxobutoxy) phenyl, [phenyl (hydroxy) ethoxy] phenyl, (pyridylmethoxy) phenyl, (pyridylethoxy) phenyl, (pyrimidylmethoxy) phenyl, (pyrimidylethoxy) phenyl, (thienylmethoxy) phenyl, (methyl (Thienylmethoxy) phenyl, (thienylethoxy) phenyl, (2-oxo-2-thienylethoxy) phenyl, [thienyl (hydroxy) ethoxy] phenyl, 4-thienylmethoxy-2-fluorophenyl, 4-thienylmethoxy-3-fluoro Phenyl, 3-thienylmethoxy-2-fluorophenyl, 3-thienylmethoxy-4-fluorophenyl, 3-thienylmethoxy-5-fluorophenyl, 3-thienylmethoxy-6-fluorophenyl, (furylmethoxy) phenyl, (furyl (Ethoxy) phenyl, (pyrrolylmethoxy) phenyl, (pyrrolylethoxy) phenyl , (Thiazolylmethoxy) phenyl, [(phenylthiazolyl) methoxy] phenyl, (dimethylthiazolylmethoxy) phenyl, (thiazolylethoxy) phenyl, (oxazolylmethoxy) phenyl, (dimethyloxazolyl) (Methoxy) phenyl, (oxazolylethoxy) phenyl, (phenyloxazolylethoxy) phenyl, [phenyl (methyl) oxazolylethoxy] phenyl, (dimethyloxazolylethoxy) phenyl, (isoxazolylmethoxy) phenyl , (Dimethylisoxazolylmethoxy) phenyl, (isoxazolylethoxy) phenyl, (dimethylisoxazolylethoxy) phenyl, (pyrimidinylmethoxy) phenyl, (2-oxo-2-thienylethoxy) phenyl, (phenoxy) (Methyl) phenyl, (methylphenoxymethyl) phenyl, (methoxyphenoxymethyl ) Phenyl, (chlorophenoxymethyl) phenyl, (phenoxyethyl) phenyl, (methylphenoxyethyl) phenyl, (chlorophenoxyethyl) phenyl, (phenoxypropyl) phenyl, (benzyloxymethyl) phenyl, (benzyloxyethyl) phenyl, (Phenethyloxymethyl) phenyl, (phenethyloxyethyl) phenyl, benzylcarbonylphenyl, (2-methylphenyl-2-oxoethoxy) phenyl, (2-methoxyphenyl-
(2-oxoethoxy) phenyl, (2-chlorophenyl-2-oxoethoxy) phenyl, phenethylcarbonylphenyl, (naphthylmethylcarbonyl) phenyl, (naphthylethylcarbonyl) phenyl, (benzyloxy) (methyl) phenyl, (benzyloxy) (Methoxy) phenyl,
(Benzyloxy) (fluoro) phenyl, (benzyloxy) (chloro) phenyl, (methyl) (thienylmethoxy) phenyl, (methoxy) (thienylmethoxy) phenyl, (chloro) (thienylmethoxy) phenyl, (methyl) (thia (Zolylmethoxy) phenyl, (methoxy) (thiazolylmethoxy) phenyl, (chloro) (thiazolylmethoxy) phenyl, (carboxylmethoxy) phenyl; naphthyl, methylnaphthyl, dimethylnaphthyl, ethylnaphthyl, butylnaphthyl, s- Butyl naphthyl, t-butyl naphthyl,
Hexylnaphthyl, propenylnaphthyl, methylpropenylnaphthyl, butenylnaphthyl, methylbutenylnaphthyl, (trifluoromethyl) naphthyl, di (trifluoromethyl) naphthyl, (pentafluoroethyl) naphthyl, methoxynaphthyl, dimethoxynaphthyl, trimethoxynaphthyl, ethoxy Naphthyl, diethoxynaphthyl, butoxynaphthyl, hexyloxynaphthyl, fluoronaphthyl, difluoronaphthyl, trifluoronaphthyl, chloronaphthyl, dichloronaphthyl, trichloronaphthyl, bromonaphthyl, dibromonaphthyl, iodonaphthyl, hydroxynaphthyl, dihydroxynaphthyl, phenylnaphthyl, Pyridylnaphthyl, thienylnaphthyl, furylnaphthyl, pyrrolylnaphthyl, pyrimidylnaphthyl, benzylnaphthyl , (Methylbenzyl) naphthyl, (methoxybenzyl) naphthyl, (fluorobenzyl) naphthyl, (chlorobenzyl) naphthyl, phenethyl Luna border Le, (methylphenethyl) naphthyl, (methoxyphenethyl) naphthyl, (fluorophenethyl) naphthyl,
(Chlorophenethyl) naphthyl, phenyl (hydroxy) methylnaphthyl, phenyl (hydroxy) ethylnaphthyl,
(Naphthylmethyl) naphthyl, (naphthylethyl) naphthyl, phenoxynaphthyl, (methylphenoxy) naphthyl, (methoxyphenoxy) naphthyl, (fluorophenoxy) naphthyl, (chlorophenoxy) naphthyl, (cyclopropylmethoxy) naphthyl, (cyclopentylmethoxy) Naphthyl, (cyclohexylmethoxy) naphthyl, benzyloxynaphthyl, (methoxybenzyloxy) naphthyl, (fluorobenzyloxy) naphthyl, (chlorobenzyloxy) naphthyl, (phenethyloxy) naphthyl, (methylphenethyloxy) naphthyl, (chlorophenethyloxy ) Naphthyl, (phenylpropyloxy) naphthyl, (methylphenylpropyloxy) naphthyl,
(Chlorophenylpropyloxy) naphthyl, (pyridylmethoxy) naphthyl, (pyridylethoxy) naphthyl, (pyrimidylmethoxy) naphthyl, (pyrimidylethoxy) naphthyl, (thienylmethoxy) naphthyl, (thienylethoxy) naphthyl, (furylmethoxy) ) Naphthyl, (furylethoxy) naphthyl, (pyrrolylmethoxy) naphthyl, (pyrrolylethoxy) naphthyl, (thiazolylmethoxy) naphthyl, (dimethylthiazolylmethoxy) naphthyl, (thiazolylethoxy) naphthyl, (oxa (Zolylmethoxy) naphthyl, (dimethyloxazolylmethoxy) naphthyl, (oxazolylethoxy) naphthyl, (dimethyloxazolylethoxy) naphthyl, (isoxazolylmethoxy) naphthyl, (dimethylisoxazolylmethoxy) naphthyl ,
(Isoxazolylethoxy) naphthyl, (dimethylisoxazolylethoxy) naphthyl, (phenoxymethyl)
Naphthyl, (methylphenoxymethyl) naphthyl, (methoxyphenoxymethyl) naphthyl, (chlorophenoxymethyl) naphthyl, (phenoxyethyl) naphthyl, (methylphenoxyethyl) naphthyl, (chlorophenoxyethyl) naphthyl, (phenoxypropyl) naphthyl, ( (Benzyloxymethyl) naphthyl, (benzyloxyethyl) naphthyl, (phenethyloxymethyl) naphthyl, (phenethyloxyethyl) naphthyl, benzylcarbonylnaphthyl, (methylbenzylcarbonyl) naphthyl, (methoxybenzylcarbonyl) naphthyl, (chlorobenzylcarbonyl) Naphthyl, phenethylcarbonyl naphthyl, (naphthylmethylcarbonyl) naphthyl, (naphthylethylcarbonyl) naphthyl, (benzyloxy) (methyl) naphthyl, (benzyloxy) (methoxy) naphthyl , (Benzyloxy) (fluoro) naphthyl, (benzyloxy) (chloro) naphthyl, (methyl) (thienylmethoxy) naphthyl,
(Methoxy) (thienylmethoxy) naphthyl, (chloro) (thienylmethoxy) naphthyl, (methyl) (thiazolylmethoxy) naphthyl, (methoxy) (thiazolylmethoxy) naphthyl, (chloro) (thiazolylmethoxy) naphthyl Pyridyl, methylpyridyl, methoxypyridyl, dimethoxypyridyl, propenylpyridyl, hexyloxypyridyl, fluoropyridyl, difluoropyridyl, chloropyridyl, dichloropyridyl, hydroxypyridyl, phenylpyridyl, thienylpyridyl, benzylpyridyl,
(Methylbenzyl) pyridyl, phenethylpyridyl, (cyclohexylmethoxy) pyridyl, benzyloxypyridyl, (chlorobenzyloxy) pyridyl, (chlorobenzyloxy) pyridyl, phenethyloxypyridyl, (pyridylmethoxy) pyridyl, (pyridylethoxy) pyridyl, ( (Thienylmethoxy) pyridyl, (thienylethoxy)
Pyridyl, (thienylpropoxy) pyridyl, (phenoxymethyl) pyridyl, (phenoxy-1-ethyl) pyridyl,
(Phenoxy-2-ethyl) pyridyl, (methylbenzyloxy) pyridyl; thienyl, methylthienyl, methoxythienyl, dimethoxythienyl, propenylthienyl, hexyloxythienyl, fluorothienyl, difluorothienyl, chlorothienyl, dichlorothienyl, hydroxythienyl, phenyl Thienyl, benzylthienyl,
(Methylbenzyl) thienyl, phenethylthienyl, (cyclohexylmethoxy) thienyl, benzyloxythienyl, (chlorobenzyloxy) thienyl, (chlorobenzyloxy) thienyl, phenethyloxythienyl, pyridylmethoxythienyl, (pyridylethoxy) thienyl, (thienylmethoxy) ) Thienyl, (thienylethoxy)
Thienyl, (thienylpropoxy) thienyl, (phenoxymethyl) thienyl, (phenoxyethyl) thienyl, (methylbenzyloxy) thienyl; benzothienyl, chlorobenzothienyl, fluorobenzothienyl, methylbenzothienyl, hydroxybenzothienyl, methoxybenzothienyl, Hexyloxythienyl, benzyloxybenzothienyl, (cyclohexylmethoxy) benzothienyl, (chlorobenzyloxy) benzothienyl, phenethylbenzothienyl, phenethyloxybenzothienyl, (phenylpropoxy) benzothienyl, (phenoxymethyl) benzothienyl, (phenoxyethyl ) Benzothienyl, (chlorobenzyloxy) benzothienyl,
(Methyltrimethoxy) benzothienyl, (methylbenzyl) benzothienyl, (methylbenzyloxy) benzothienyl, dichlorobenzothienyl, difluorobenzothienyl, dimethoxybenzothienyl, (benzyloxymethoxy) benzothienyl, (pyridylmethoxy) benzothienyl, (Pyridylethoxy) benzothienyl, (thienylmethoxy) benzothienyl, (thienylethyl) benzothienyl, (allyl) benzothienyl; quinolyl, chloroquinolyl, fluoroquinolyl, methylquinolyl, hydroxyquinolyl, methoxyquinolyl, hexyloxy,
Benzyloxyquinolyl, (cyclohexylmethoxy) quinolyl, (chlorobenzyloxy) quinolyl, phenethylquinolyl, phenethyloxyquinolyl, (phenylpropoxy) quinolyl, (phenoxymethyl) quinolyl, (phenoxyethyl) quinolyl, (chlorobenzyloxy) Quinolyl, (methyltrimethoxyquinolyl), (methylbenzyl) quinolyl, (methylbenzyloxy) quinolyl, dichloroquinolyl, difluoroquinolyl, dimethoxyquinolyl, (benzyloxymethoxy) quinolyl, (pyridylmethoxy) quinolyl, (pyridyl (Ethoxy) quinolyl, (thienylmethoxy) quinolyl, (thienylethyl) quinolyl,
Allylquinolyl; benzofuryl, chlorobenzofuryl,
Fluorobenzofuryl, methylbenzofuryl, hydroxybenzofuryl, methoxybenzofuryl, hexyloxybenzofuryl, benzyloxybenzofuryl, (cyclohexylmethoxy) benzofuryl, (chlorobenzyloxy) benzofuryl, phenethylbenzofuryl, phenethyloxybenzofuryl, (phenyl (Propoxy) benzofuryl, (phenoxymethyl) benzofuryl, (phenoxyethyl) benzofuryl, (chlorobenzyloxy) benzofuryl, (methyltrimethoxy) benzofuryl, (methylbenzyl) benzofuryl, (benzoyl) benzofuryl, (methylbenzyloxy) benzofuryl, dimethoxybenzo Furyl, (benzyloxymethoxy) benzofuryl, (pyridylmethoxy) benzofuryl, (pyridylethoxy) benzofuryl, (thienylmethoxy) Benzofuryl, (thienylethyl) benzofuryl, allylbenzofuryl; 2,3-dihydrobenzofuryl, chloro-2,3-dihydrobenzofuryl, fluoro-2,3-dihydrobenzofuryl, methyl-2,3-dihydrobenzofuryl, Hydroxy-2,3-dihydrobenzofuryl, methoxy-2,3-
Dihydrobenzofuryl, hexyloxy-2,3-dihydrobenzofuryl, benzyloxy-2,3-dihydrobenzofuryl, (cyclohexylmethoxy) -2,3-dihydrobenzofuryl, (chlorobenzyloxy) -2,3-dihydro Benzofuryl, phenethyl-2,3-dihydrobenzofuryl, phenethyloxy-2,3-dihydrobenzofuryl, (phenylpropoxy) -2,3-dihydrobenzofuryl, (phenoxymethyl) -2,3-dihydrobenzofuryl, (Phenoxyethyl) -2,3-dihydrobenzofuryl, (chlorobenzyloxy) -2,3-dihydrobenzofuryl, (methyltrimethoxy) -2,3-dihydrobenzofuryl, (methylbenzyl) -2,3- Dihydrobenzofuryl, (methylbenzyloxy) -2,3-dihydrobenzofuryl, dichloro-2,3-dihydrobenzofuryl Difluoro-2,3-dihydrobenzofuryl, dimethoxy-2,
3-dihydrobenzofuryl, (benzyloxymethoxy)-
2,3-dihydrobenzofuryl, (pyridylmethoxy)-
2,3-dihydrobenzofuryl, (pyridylethoxy)-
2,3-dihydrobenzofuryl, (thienylmethoxy)-
2,3-dihydrobenzofuryl, (thienylethyl) -2,
Examples thereof include 3-dihydrobenzofuryl and allyl-2,3-dihydrobenzofuryl.

The 2-mercaptocarboxylic acid derivative having the general formula (I) of the present invention has a carboxyl group in its basic structure and when the substituted α is a carboxyalkoxy group. This carboxyl group can be converted into a pharmacologically acceptable ester according to a conventional method.
The pharmacologically acceptable ester of the 2-mercaptocarboxylic acid derivative having the general formula (I) is not particularly limited as long as it is used medically and is pharmacologically acceptable.

The ester residue of the 2-mercaptocarboxylic acid derivative having the general formula (I) of the present invention includes, for example, a linear or branched alkyl group having 1 to 6 carbon atoms, An aralkyl group having 7 to 19,
A linear or branched alkyl group having 1 to 5 carbon atoms substituted by a linear or branched alkanoyloxy having 1 to 6 carbon atoms, 1 to 6 carbon atoms
Linear or branched alkyloxycarbonyloxy substituted with 1 to 5 carbon atoms, linear or branched alkyloxycarbonyloxy having 1 to 5 carbon atoms, cycloalkylcarbonyl having 5 to 7 carbon atoms A straight-chain or branched alkyl group having 1 to 5 carbon atoms substituted by oxy, a straight-chain having 1 to 5 carbon atoms substituted by cycloalkyloxycarbonyloxy having 5 to 7 carbon atoms Linear or branched alkyl group having 1 to 5 carbon atoms, substituted by arylcarbonyloxy having 6 to 10 carbon atoms, 6 to 10 carbon atoms A straight-chain or branched alkyl group having 1 to 5 carbon atoms, which is substituted by an aryloxycarbonyloxy group having 1 to 5 carbon atoms; Having a straight-chain or branched alkyl having 6 or 2-oxo-1,3-dioxolen -
A 4-ylmethyl group can be mentioned.

Here, a linear or branched alkyl group having 1 to 4 carbon atoms and a linear or branched alkyl group having 1 to 6 carbon atoms are, for example, methyl, Ethyl, propyl, isopropyl, butyl,
Isobutyl, s-butyl, t-butyl, pentyl, methylbutyl, dimethylpropyl, ethylpropyl, hexyl, methylpentyl, dimethylbutyl, ethylbutyl,
Or trimethylpropyl, preferably a linear or branched alkyl group having 1 to 4 carbon atoms, more preferably methyl, ethyl, propyl, isopropyl, butyl or isobutyl. Is methyl or ethyl.

An aralkyl group having 7 to 19 carbon atoms is, for example, benzyl, phenethyl, phenylpropyl,
Phenylbutyl, naphthylmethyl or dibenzyl, preferably benzyl.

The cycloalkyl group having 5 to 7 carbon atoms is, for example, cyclopentyl, cyclohexyl, cycloheptyl, preferably cyclohexyl.

The aryl group having 6 to 10 carbon atoms is, for example, phenyl or naphthyl, preferably phenyl.

Specific examples of suitable ester residues include methyl,
Ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, benzyl, acetoxymethyl, 1- (acetoxy) ethyl, propionyloxymethyl, propionyloxyethyl, butyryloxymethyl, butyryloxyethyl, isobutyryloxyethyl, Valeryloxymethyl, valeryloxyethyl, isovaleryloxymethyl, isovaleryloxyethyl, pivaloyloxymethyl, pivaloyloxyethyl, methoxycarbonyloxymethyl, methoxycarbonyloxyethyl, ethoxycarbonyloxymethyl, ethoxy Carbonyloxyethyl, propoxycarbonyloxymethyl, propoxycarbonyloxyethyl, isopropoxycarbonyloxymethyl, isopropoxycarbonyloxyethyl, butoxycarbonyl Oxymethyl, butoxycarbonyloxyethyl, isobutoxycarbonyloxymethyl, isobutoxycarbonyloxyethyl, t-butoxycarbonyloxymethyl, t-butoxycarbonyloxyethyl, cyclopentanecarbonyloxymethyl, cyclopentanecarbonyloxyethyl, cyclohexanecarbonyloxymethyl , Cyclohexanecarbonyloxyethyl, cyclopentyloxycarbonyloxymethyl, cyclopentyloxycarbonyloxyethyl, cyclohexyloxycarbonyloxymethyl, cyclohexyloxycarbonyloxyethyl, benzoyloxymethyl, benzoyloxyethyl, phenoxycarbonyloxymethyl, phenoxycarbonyloxyethyl or 5- Methyl-2-oxo-1,3-dioxole -4-Methyl and more preferably methyl or ethyl.

The carboxyl group of the 2-mercaptocarboxylic acid derivative having the general formula (I) can be converted into a metal salt according to a conventional method. Examples of such salts include alkali metal salts such as lithium, sodium and potassium; alkaline earth metal salts such as calcium, barium and magnesium; aluminum salts; Preferably, it is an alkali metal salt.

When the 2-mercaptocarboxylic acid derivative of the general formula (I) of the present invention has a base moiety such as a pyridyl group or a quinolyl group, it can be converted to a salt. Such salts include, for example, hydrohalides such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid; inorganic salts such as nitrates, perchlorates, sulfates and phosphates. Acid salts; lower alkanesulfonic acid salts such as methanesulfonic acid, trifluoromethanesulfonic acid and ethanesulfonic acid; arylsulfonic acid salts such as benzenesulfonic acid and p-toluenesulfonic acid; glutamic acid, aspartic acid and the like And salts of organic acids such as fumaric acid, succinic acid, citric acid, tartaric acid, oxalic acid and salts of carboxylic acids such as maleic acid.

The compounds of the present invention also include various isomers. For example, the 2-position carbon of the 2-mercaptocarboxylic acid derivative of the formula (I) is an asymmetric carbon, and an asymmetric carbon may be present on the substituent, so that an optically active substance is present. Further, those having a double bond on the carbon chain have geometrical isomerism. The present invention includes all of these isomers.

Furthermore, the present invention relates to a method for preparing a 2-mercaptocarboxylic acid derivative represented by the above general formula (I), a pharmacologically acceptable ester thereof, or a pharmacologically acceptable salt thereof, comprising a solvate (eg, hydrate) ) Is included in all cases.

Further, the present invention relates to
A 2-mercaptocarboxylic acid derivative of the general formula (I) or
Are their pharmaceutically acceptable esters or their pharmacology
Chemically acceptable compounds that form salts, so-called prodrugs
Are all included. A 2-method having the general formula (I)
In the rucaptocarboxylic acid derivative, preferably, (1) A is C₆-C_TenAryl group (1 or 2 substituted α
You may have. ) Or a heteroaromatic ring group (substituted α
Or it may have two. 2-mercap represented by)
Tricarboxylic acid derivatives or their pharmacologically acceptable
Steles or pharmacologically acceptable salts thereof. (2) A is C₆-C_TenAryl group (1 or 2 substituted α
You may have. ) Or one or two heteroatoms
Heteroaromatic group (having one or two substituents α)
May be. 2-mercaptocarboxylic acid derivative represented by)
Body or its pharmacologically acceptable esters or it
Pharmacologically acceptable salts thereof. (3) A is C₆-C_TenAryl group (1 or 2 substituted α
You may have. ) Or a complex having one heteroatom
Represented by an aromatic ring group (which may have one substituent α).
2-mercaptocarboxylic acid derivative or its pharmacology
Acceptable esters or their pharmacologically acceptable
Salt. (4) A is C₆-C_TenAryl group (having one substituent α
Is also good. ) Or a heteroaromatic group having one heteroatom (position
It may have one substitution α. 2-merca represented by)
Ptocarboxylic acid derivative or its pharmacologically acceptable
Esters or pharmacologically acceptable salts thereof. (5) A is C₆-C_TenAryl group (having one substituent α
Is also good. 2-mercaptocarboxylic acid derivative represented by
Or their pharmaceutically acceptable esters or their esters
Pharmacologically acceptable salts. (6) A is a heteroaromatic group having one heteroatom (substituted
It may have one α. 2-mercapto represented by)
Carboxylic acid derivative or its pharmacologically acceptable S
Ters or pharmacologically acceptable salts thereof. (7) 2- in which X is a bond, an oxygen atom or a sulfur atom
Mercaptocarboxylic acid derivative or its pharmacologically acceptable
Esters or pharmacologically acceptable salts thereof. (8) 2-mercapcapsule in which X is a bond or an oxygen atom
Tricarboxylic acid derivatives or their pharmacologically acceptable
Steles or pharmacologically acceptable salts thereof. (9) 2-mercaptocarboxylic acid derivative in which X is represented by a bond
Conductors or their pharmacologically acceptable esters or
Their pharmacologically acceptable salts. (10) 2-mercaptocarboxy where X is an oxygen atom
Acid derivatives or their pharmacologically acceptable esters or
Are their pharmacologically acceptable salts. (11) W and Y are each independently a bond or C₁-C
_FifteenAlkylene group (provided that -W-X-Y- group does not represent a methylene group)
No. 2-mercaptocarboxylic acid derivative represented by
Or their pharmacologically acceptable esters or their drugs
Physically acceptable salt. (12) W and Y are each independently a bond or C₁-C
_TenAlkylene group (provided that -W-X-Y- group does not represent a methylene group)
No. 2-mercaptocarboxylic acid derivative represented by
Or their pharmacologically acceptable esters or their drugs
Physically acceptable salt. (13) W and Y are each independently a bond or C₁-C₈
Alkylene group (provided that -W-X-Y- group does not represent a methylene group)
No. 2-mercaptocarboxylic acid derivative represented by
Or their pharmacologically acceptable esters or their drugs
Physically acceptable salt. (14) W and Y are each independently a bond or C₁-C₆
Alkylene group (provided that -W-X-Y- group does not represent a methylene group)
No. 2-mercaptocarboxylic acid derivative represented by
Or their pharmacologically acceptable esters or their drugs
Physically acceptable salt. (15) R is a hydrogen atom or C₁-C₆Represented by an alkanoyl group
2-mercaptocarboxylic acid derivative or its pharmacology
Pharmaceutically acceptable esters or their pharmacologically acceptable nature
Salt. (16) R is a hydrogen atom or C₁-C_FourRepresented by an alkanoyl group
2-mercaptocarboxylic acid derivative or its pharmacology
Pharmaceutically acceptable esters or their pharmacologically acceptable nature
Salt. (17) R is a hydrogen atom or C₁-C_TwoRepresented by an alkanoyl group
2-mercaptocarboxylic acid derivative or its pharmacology
Pharmaceutically acceptable esters or their pharmacologically acceptable nature
Salt. (18) 2-mercaptocarboxy wherein R is a hydrogen atom
Acid derivatives or their pharmacologically acceptable esters or
Are their pharmacologically acceptable salts. (19) The substitution α is (i) C₁-C_TenAlkyl group (substituted β
You may have 1 to 3 pieces. ), (Ii) C_Two-C_TenUnsaturated charcoal
A hydride group (which may have one substituent β), (iii) C
₁-C_TenAlkoxy group, (iv) halogen atom, (v) hydroxyl group, (v
I c₆-C_TenAryl group (having one or two substituents β
May be. ), (Vii) a monocyclic heteroaromatic group, (viii) C₇-C
₁₆An aralkyl group (substituted β with 1 or 2
Hydroxyl group as a substituent on the alkyl
May be provided. ), (Ix) C ₇-C₁₆Aralkirka
Rubonyl group (which may have one or two substituents β)
No. ), (X) C₆-C_TenAryloxy group (substituent β
Or two of them. ), (Xi) C₆-C₁₂Cycloal
A alkylalkyloxy group, (xii) C₇-C₁₆Aralkyloxy
Group (having one or two substituents β on the aryl
Having one hydroxyl group as a substituent on the alkyl
May be. ), (Xiii) C₇-C₁₆Arylcarbonyl al
A killoxy group (one or two substituents β on the aryl
You may have. ), (Xiv) monocyclic heteroaromatic ring C₁-C₆A
Alkyloxy group (substituted β on the monocyclic heteroaromatic ring
Or two of them may be substituted on the alkyl.
May have one hydroxyl group. ), (Xv) monocyclic hetero
Aromatic ring C₁-C₆Carbonylalkyloxy group (monocyclic heteroaromatic
May have one or two substituents β on the aromatic ring
No. ), (Xvi) C₇-C₁₆Aryloxyalkyl group (aryl
May have one substitution β on the ring. ), (Xvii) C₈-
C_{twenty two}Aralkyloxyalkyl group (substituted β on aryl
May be provided. ) Or (xviii) C_Two-C₉Carbo
2-mercaptocarboxylic acid represented by a xyalkoxy group
Derivatives or pharmacologically acceptable esters thereof or
Their pharmacologically acceptable salts. (20) The substitution α is (i) C₁-C_TenAlkyl group, (ii) C_Two-C_Ten
Unsaturated hydrocarbon group, (iii) C₁-C_TenAn alkoxy group, (iv)
(V) hydroxyl group, (vi) C₆-C_TenAryl group (substituted
It may have one β. ), (Vii) monocyclic heteroaromatic ring
Group, (viii) phenyl C₁-C_FourAlkyl group (substituted on phenyl
May have one or two parts β, on the alkyl
It may have one hydroxyl group as a substituent. ), (Ix)
Phenyl C₁-C_FourCarbonylalkyl group (substituted on phenyl
It may have one or two parts β. ), (X) Pheno
Xy group (having one or two substituents β on phenyl
May be. ), (Xi) C₆-C_TenCycloalkylalkylo
Xy group, (xii) phenyl C₁-C₆Alkyloxy group (phenyl
May have one or two substituents β on the
May have one hydroxyl group as a substituent on the alkyl.
No. ), (Xiii) phenyl C ₁-C₆Carbonylalkyloxy
Group (having one or two substituents β on phenyl
Is also good. ), (Xiv) a unit having one or two heteroatoms
Cyclic heteroaromatic ring C₁-C₆Alkyloxy group (monocyclic heteroaromatic
May have one or two substituents β on the ring,
May have one hydroxyl group as a substituent on the alkyl.
No. ), (Xv) monocyclic having one or two heteroatoms
Heteroaromatic ring C₁-C₆Carbonylalkyloxy group (monocyclic
May have one or two substituents β on the aromatic ring.
No. ), (Xvi) phenoxy C₁-C₆Alkyl group (on phenyl
May have one substitution β. ), (Xvii) phenyl C
₁-C₆Alkyloxy C₁-C₆Alkyl group (substituted on phenyl
May have one component β. ) Or (xviii) C_Two-C₇Mosquito
2-mercaptocarbo represented by ruboxoxyalkoxy group
Acid derivatives or pharmacologically acceptable esters thereof
Or their pharmacologically acceptable salts. (21) The substitution α is (i) C₁-C₆Alkyl group, (ii) C₁-C₈A
Alkoxy group, (iii) halogen atom, (iv) hydroxyl group, (v)
Nyl group (which may have one substituent β);
Nil C₁-C_FourAlkyl group (having one substituent β on phenyl
May be substituted with one hydroxyl group on the alkyl.
You may have. ), (Vii) phenyl C₁-C_FourCarbonyl
Alkyl group (even if there is one substituent β on phenyl
Good. ), (Viii) a phenoxy group (having one substituent β)
You may. ), (Ix) C₆-C_TenCycloalkylalkyloxy
Si group, (x) phenyl C₁-C₆Alkyloxy group (on phenyl
May have one or two substituents β,
May have one hydroxyl group as a substituent on the
No. ), (Xi) phenyl C₁-C₆Carbonylalkyloxy group
(Even if phenyl has one or two substituents β
Good. ), (Xii) a monocyclic ring having one or two heteroatoms
Formula heteroaromatic ring C₁-C_FourAlkyloxy group (monocyclic heteroaromatic ring
May have one or two substituents β on the
It may have one hydroxyl group as a substituent on the kill.
No. ), (Xiii) a monocyclic ring having one or two heteroatoms
Formula heteroaromatic carbonyl C₁-C_FourAlkyloxy group (monocyclic
Even if the heteroaromatic ring has one or two substituents β
Good. ), (Xiv) phenoxy C₁-C_FourAlkyl group, (xv)
Nil C₁-C_FourAlkyloxy C₁-C_FourAlkyl group, or (xvi) C
_Two-C_Five2-mercapto represented by a carboxyalkoxy group
Carboxylic acid derivative or its pharmacologically acceptable S
Ters or pharmacologically acceptable salts thereof. (22) The substitution α is (i) C₁-C_FourAlkyl group, (ii) C₁-C₆A
Alkoxy group, (iii) halogen atom, (iv) hydroxyl group, (v)
Nyl group, (vi) phenyl C₁-C_FourAlkyl group (placed on alkyl
It may have one hydroxyl group as a replacement. ), (Vii)
Henil C₁-C_FourCarbonylalkyl group, (viii) phenoxy
Group, (ix) C₆-C_TenCycloalkylalkyloxy group, (x)
Phenyl C₁-C_FourAlkyloxy group (substituted β on phenyl
May be substituted on the alkyl as water
It may have one acid group. ), (Xi) phenyl C₁-C_FourMosquito
Rubonylalkyloxy group (substituted β on phenyl
You may have one. ), (Xii) one or more heteroatoms
Monocyclic heteroaromatic ring C having two₁-C_FourAlkyloxy group (simple
Having one or two substituents β on the cyclic heteroaromatic ring
May have one hydroxyl group as a substituent on the alkyl
May be. ), (Xiii) 1 or 2 heteroatoms
Having a monocyclic heteroaromatic carbonyl C₁-C_FourAlkyloxy
Si group (one or two substituents β on a monocyclic heteroaromatic ring)
You may have. ), (Xiv) phenyl C₁-C_FourAlkylo
Kiss C₁-C_FourAlkyl group, or (xv) C_Two-C_FiveCarboxyalco
2-mercaptocarboxylic acid derivative represented by xy group
Or their pharmacologically acceptable esters or their drugs
Physically acceptable salt. (23) The substitution α is (i) C₁-C_TwoAlkyl group, (ii) C₁-C₆A
Lucoxy group, (iii) chlorine atom, (iv) hydroxyl group, (v) phenyl
C₁-C_FourAlkyl group (a hydroxyl group is substituted on the alkyl
You may have one. ), (Vi) phenyl C₁-C_FourCarbonyl
Alkyl group, (vii) phenyl C₁-C_FourAlkyloxy group (
Phenyl may have one substituent β on the
It may have one hydroxyl group as a substituent on it. ),
(viii) phenyl C₁-C_FourA carbonylalkyloxy group, or
Is (ix) a monocyclic heteroaromatic having one or two heteroatoms
Incense Ring C₁-C_FourAlkyloxy group (substituted on monocyclic heteroaromatic ring
May have one component β. 2-mercap represented by)
Tricarboxylic acid derivatives or their pharmacologically acceptable
Steles or pharmacologically acceptable salts thereof. (24) The substitution α is (i) phenyl group, (ii) phenyl C₁-C
_FourAlkyl group (having one hydroxyl group as a substituent on alkyl)
It may be. ), (Iii) phenyl C₁-C_FourCarbonyl
Alkyl group, (iv) phenoxy group, (v) C₆-C_TenCycloalkyl
Alkyloxy group, (vi) phenyl C₁-C_FourAlkyloxy
Si group (may have one substituent β on phenyl,
It may have one hydroxyl group as a substituent on alkyl.
No. ), (Vii) phenyl C₁-C_FourCarbonylalkyloxy
Group (may have one substituent β on phenyl),
(viii) monocyclic heteroaromatic having one or two heteroatoms
Incense Ring C₁-C_FourAlkyloxy group (substituted on monocyclic heteroaromatic ring
May have one or two parts β, on the alkyl
It may have one hydroxyl group as a substituent. ), (Ix)
Monocyclic heteroaromatic ring having one or two heteroatoms
Rubonil C₁-C_FourAlkyloxy group (on the monocyclic heteroaromatic ring
It may have one or two substituents β. ) Or
(x) phenyl C₁-C_FourAlkyloxy C₁-C_FourTable with alkyl group
2-mercaptocarboxylic acid derivative or its drug
Physically acceptable esters or their pharmacologically acceptable
Salt. (25) When the substituted α is (i) phenyl C₁-C_FourAlkyl group (Al
It may have one hydroxyl group as a substituent on the kill.
No. ), (Ii) phenyl C₁-C_FourA carbonylalkyl group, (ii
i) Phenyl C₁-C_FourAlkyloxy group (substituted on phenyl
may have one β as a substituent on the alkyl
It may have one hydroxyl group. ), (Iv) phenyl C₁-C_Four
One carbonylalkyloxy group or (v) heteroatom
Or a monocyclic heteroaromatic ring C having two₁-C_FourAlkylo
A xy group (having one substituent β on a monocyclic heteroaromatic ring)
You may. 2-mercaptocarboxylic acid derivative represented by
Or pharmacologically acceptable esters thereof or those thereof
Pharmacologically acceptable salts of (26) When the substituted α is (i) phenyl C₁-C_FourAlkyloxy
Group (which may have one substituent β on phenyl,
May have one hydroxyl group as a substituent on the alkyl.
No. ), (Ii) phenyl C₁-C_FourCarbonylalkyloxy
A group or (iii) a monocyclic ring having one or two heteroatoms
Formula heteroaromatic ring C₁-C_FourAlkyloxy group (monocyclic heteroaromatic ring
It may have one substitution β thereon. ) 2-
Mercaptocarboxylic acid derivative or its pharmacologically acceptable
Esters or pharmacologically acceptable salts thereof. (27) When the substituted α is (i) phenyl C₁-C_TwoAlkyloxy
Group (may have one substituent β on phenyl),
(ii) phenyl C₁-C_TwoA carbonylalkyloxy group, or
(iii) monocyclic heteroaromatic having one or two heteroatoms
Incense Ring C₁-C_TwoAlkyloxy group (substituted on monocyclic heteroaromatic ring
May have one component β. 2-mercap represented by)
Tricarboxylic acid derivatives or their pharmacologically acceptable
Steles or pharmacologically acceptable salts thereof. (28) When the substitution β is (i) C₁-C₆Alkyl group, (ii) C₁-C₆
Alkoxy group, (iii) C₁-C ₆Alkylthio group, (iv) halogen
Atom, (v) C₁-C_FourAlkylenedioxy group, (vi) nitro
Group, (vii) cyano group, (viii) C₁-C₆Alkanoyl group, or
(ix) 2-mercaptocarboxylic acid derivative represented by phenyl group
Conductors or their pharmacologically acceptable esters or
Their pharmacologically acceptable salts. (29) The substitution β is (i) C₁-C₆Alkyl group, (ii) C₁-C₆
Alkoxy group, (iii) halogen atom, (iv) nitro group, (v)
2-mercap represented by a cyano group or (vi) a phenyl group
Tricarboxylic acid derivatives or their pharmacologically acceptable
Steles or pharmacologically acceptable salts thereof. (30) When the substitution β is (i) C₁-C_FourAlkyl group, (ii) C₁-C_Four
An alkoxy group, (iii) a halogen atom, or (iv) phenyl
A 2-mercaptocarboxylic acid derivative represented by a group
Its pharmaceutically acceptable esters or their pharmacology
Above acceptable salts. (31) The substitution β is (i) C₁-C_TwoAlkyl group, (ii) C₁-C_Two
2-methyl represented by an alkoxy group or (iii) a halogen atom
Lucatocarboxylic acid derivative or its pharmacologically acceptable properties
Esters or pharmacologically acceptable salts thereof. Ma
In addition, 2-mercaptocarboxylic acid derivative having the general formula (I)
In the conductor, A is selected from (1) to (6), and (7)
Select X from (10) to (10) and select (11) to (14)
Select W and Y and select R from (15) to (18)
Then, α is selected from (19) to (27), and (28) to
Compounds selected by combining β from (31) are also suitable.
is there. For example, 2-mercapto having the general formula (I)
Among the carboxylic acid derivatives, the following compounds are also suitable. (32) A is C₆-C_TenAryl group (substituted α is 1 or
You may have two. ) Or one or more heteroatoms
A heteroaromatic group having two (having one or two substituents α)
It may be. X is a bond, an oxygen atom or
Represents a sulfur atom; W and Y are each independently a bond
Hand or C₁-C_TenAlkylene group (however, -W-X-Y- group is methylene
No group is shown. R represents a hydrogen atom or C₁-C_Four
Represents an alkanoyl group;₁-C_TenArchi
Group, (ii) C_Two-C_TenUnsaturated hydrocarbon group, (iii) C₁-C _TenAl
Coxy group, (iv) halogen atom, (v) hydroxyl group, (vi) C₆-C_Ten
Aryl group (which may have one substituent β), (vi
i) a monocyclic heteroaromatic group, (viii) phenyl C₁-C _FourAlkyl
Group (having one or two substituents β on phenyl
Having one hydroxyl group as a substituent on the alkyl
May be. ), (Ix) phenyl C₁-C_FourCarbonylalkyl
Group (having one or two substituents β on phenyl
Is also good. ), (X) phenoxy group (substituted β on phenyl
It may have one or two. ), (Xi) C₆-C_TenShiku
Loalkylalkyloxy group, (xii) phenyl C₁-C₆Al
A killoxy group (one or two substituents β on phenyl
May have a hydroxyl group as a substituent on the alkyl
You may have one. ), (Xiii) phenyl C₁-C₆Carbo
Nylalkyloxy group (substitute β on phenyl
Or two of them. ), (Xiv) one heteroatom
Or two monocyclic heteroaromatic rings C₁-C₆Alkyloxy
Si group (one or two substituents β on a monocyclic heteroaromatic ring)
May have a hydroxyl group as a substituent on the alkyl
You may have one. ), (Xv) one heteroatom
Is a monocyclic heteroaromatic ring C having two₁-C₆Carbonyl alkyl
A luoxy group (with one or more substituents β on the monocyclic heteroaromatic ring)
May have two. ), (Xvi) phenoxy C₁-C₆A
Alkyl group (may have one substituent β on phenyl
No. ), (Xvii) phenyl C₁-C₆Alkyloxy C₁-C₆Al
A kill group (may have one substituent β on phenyl
No. ) Or (xviii) C_Two-C₇Represents a carboxyalkoxy group
And the substitution β is (i) C₁-C₆Alkyl group, (ii) C₁-C₆Al
Coxy group, (iii) halogen atom, (iv) nitro group, (v) shea
2-mercaptoka represented by a phenyl group or (vi) a phenyl group
Rubonic acid derivatives or pharmaceutically acceptable esthetics
Or pharmacologically acceptable salts thereof. (33) A is C₆-C_TenAryl group (substituted α is 1 or
You may have two. ) Or having one heteroatom
Represents a heteroaromatic ring group (which may have one substituent α).
X represents a bond or an oxygen atom; W and Y represent
Each independently a bond or C₁-C₈Alkylene group (however,
The -W-X-Y- group does not show a methylene group. R) is water
And the substituent α is (i) C₁-C_FourAn alkyl group, (ii)
C₁-C₆Alkoxy group, (iii) halogen atom, (iv) hydroxyl group,
(v) phenyl group, (vi) phenyl C₁-C_FourAlkyl group (alkyl
May have one hydroxyl group as a substituent on the
No. ), (Vii) phenyl C₁-C_FourCarbonylalkyl group, (vi
ii) phenoxy group, (ix) C₆-C_TenCycloalkylalkyl
Oxy group, (x) phenyl C₁-C_FourAlkyloxy group (phenyl
May have one substituent β on the alkyl,
It may have one hydroxyl group as a substituent. ), (Xi)
Phenyl C₁-C_FourCarbonylalkyloxy group (on phenyl
May have one substitution β. ), (Xii) Heterogen
Monocyclic heteroaromatic ring C having 1 or 2 carbon atoms₁-C _FourAl
A killoxy group (a monocyclic heteroaromatic ring with a substituent β
Or two of them may be substituted as a substituent on the alkyl.
It may have one hydroxyl group. ), (Xiii) heteroatom
Monocyclic heteroaromatic ring carbonyl C having 1 or 2₁
-C_FourAlkyloxy group (substituted β on a monocyclic heteroaromatic ring
It may have one or two. ), (Xiv) phenyl C₁
-C_FourAlkyloxy C₁-C_FourAlkyl group, or (xv) C_Two-C_FiveMosquito
Represents a ruboxoxyalkoxy group; the substituent β is represented by (i) C₁-C_FourA
Alkyl group, (ii) C₁-C_FourAlkoxy group, (iii) halogen source
Or (iv) 2-mercaptocal represented by a phenyl group
Bonic acid derivatives or pharmacologically acceptable esters thereof
Or pharmacologically acceptable salts thereof. (34) A is C₆-C_TenAryl group (having one substituent α
May be. X represents a bond; W and Y
Are each independently a bond or C₁-C₆Alkylene group (however
However, the -W-X-Y- group does not show a methylene group. ); R
Represents a hydrogen atom; the substitution α is (i) phenyl C₁-C_FourAl
A killoxy group (having one substituent β on phenyl
Having one hydroxyl group as a substituent on the alkyl
May be. ), (Ii) phenyl C₁-C_FourCarbonylalkyl
Having one or two oxy groups or (iii) heteroatoms
Monocyclic heteroaromatic ring C₁-C_FourAlkyloxy group (monocyclic heterocyclic
The aromatic ring may have one substituent β. )
And the substitution β is (i) C₁-C_TwoAlkyl group, (ii) C₁-C_TwoAl
2-merca represented by a oxy group or (iii) a halogen atom
Ptocarboxylic acid derivative or its pharmacologically acceptable
Esters or pharmacologically acceptable salts thereof. Furthermore,
2-mercaptocarboxylic acid derivative having the general formula (I)
In the above, the following compounds are also suitable. (35) A has 1 to 3 substituents α described below.
An aryl group having 6 to 10 carbon atoms which may or may not be
An oxygen source optionally having 1 to 3 substituents α
A member selected from the group consisting of
X represents a heteroaromatic ring group having 1 to 3 telo atoms, and X is
Represents a bond, an oxygen atom, a sulfur atom, or an -NH- group;
And Y are each independently a bond or a linear or branched bond.
A branched alkylene group having 1 to 20 carbon atoms
However, the -W-X-Y- group does not show a methylene group.

R is a hydrogen atom, an alkanoyl group having 1 to 6 carbon atoms, or an arylaminocarbonyl having an aryl having 6 to 10 carbon atoms which may have 1 to 3 substituents β described later. Represents a group;
Is (i) a substituent β described later (however, excluding an alkyl group).
A linear or branched alkyl group having 1 to 20 carbon atoms which may have 1 to 3 carbon atoms, and (ii) 1 substituent β (excluding the alkyl group) described later. A straight-chain or branched-chain unsaturated hydrocarbon group having 2 to 20 carbon atoms and having 1 to 3 double bonds which may have 1 to 3 carbon atoms; A branched alkoxy group having 1 to 10 carbon atoms, (iv) a halogen atom, (v)
A hydroxyl group, (vi) an aryl group having 6 to 10 carbon atoms which may have 1 to 3 substituents β described later, (vii)
A 5- or 6-membered monocyclic heteroaromatic group having 1 to 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, (viii) having 1 to 3 substituents β described later An aralkyl group having an aryl having 6 to 10 carbon atoms and an alkyl having 1 to 6 carbon atoms, which may have one hydroxyl group as a substituent, (ix) an aryloxy group having 6 to 10 carbon atoms which may have 1 to 3 substituents β described later, (x) a cycloalkyl having 3 to 6 carbon atoms and a linear or branched A branched cycloalkylalkyloxy group having an alkyl having 1 to 6 carbon atoms, (xi) an aryl having 6 to 10 carbon atoms which may have 1 to 3 substituents β described later, and Straight or branched carbon number 1 Aralkyloxy group with an alkyl having 6 or optimum, a hetero atom selected from the group consisting of (xii) an oxygen atom, a nitrogen atom and a sulfur atom 1
A 5- or 6-membered monocyclic heteroaromatic ring having 1 to 3 carbon atoms and a monocyclic heteroaromatic alkyloxy group having a linear or branched alkyl having 1 to 6 carbon atoms, (xii
i) aryloxy having 6 to 10 carbon atoms which may have 1 to 3 substituents β described later and aryloxy having a linear or branched alkyl having 1 to 6 carbon atoms Alkyl group, (xiv) 1
Aryl having 6 to 10 carbon atoms which may have 1 to 3 carbon atoms and linear or branched carbon atoms having 1 to 6 carbon atoms
Arylalkyloxyalkyl groups each independently having two alkyl groups, or (xv) aryl having 6 to 10 carbon atoms which may have 1 to 3 substituent (s) β described later and linear Represents an arylalkylcarbonyl group having a linear or branched alkyl having 1 to 6 carbon atoms, wherein the substituent β is (i) a linear or branched carbon atom having 1 to 6 carbon atoms An alkyl group, (ii)
A linear or branched alkoxy group having 1 to 6 carbon atoms, (iii) a linear or branched carbon atom having 1 carbon atom
An alkylthio group having from 6 to 6, (iv) a halogen atom,
(v) an alkylenedioxy group having 1 to 4 carbon atoms,
(vi) nitro group, (vii) cyano group, (viii) 1 to 6 carbon atoms
Alkanoyl group, (ix) carbamoyl group, or
(x) a 2-mercaptocarboxylic acid derivative represented by a linear or branched alkoxycarbonylamino group having an alkoxy having 1 to 6 carbon atoms, a pharmaceutically acceptable salt thereof, or a pharmacology thereof Esters that are acceptable.

Specific examples of the 2-mercaptocarboxylic acid derivative having the general formula (I) of the present invention include the compounds shown in the following table. Table 1
In Table 16 to Table 16, abbreviations indicate the following groups. Ac: acetyl, Bfur: benzofuryl, Bimid: benzimidazolyl, Bn: benzyl, Boxa: benzoxazolyl, Bthi:
Benzothienyl, Bthiz: benzothiazolyl, Bz: benzoyl, cHe: cyclohexyl, dHBfur: dihydrobenzofuran, Et: ethyl, Fur: furyl, Ind: indolyl, Isox: isoxazolyl, Me: methyl, Np: naphthyl, Oxa: oxazolyl, Ph: Phenyl, Pym: pyrimidinyl, Pyr: pyridyl, Pyz: pyrazinyl, Quin: quinolyl, Thi: thienyl, Thiz: thiazolyl.

[0104]

Embedded image

[0105]

X represents a single bond. 例 示 Exemplified Compound A Substituent A on Ring A W-X-Y R number ─────────────────────────────── 1-1 4-Cl Ph (CH ₂ ) ₃ H 1-2 4-PhCH ₂ O Ph (CH ₂ ) ₃ H 1-3 4-Cl Ph (CH ₂ ) ₄ H 1-4 4-PhCH ₂ O Ph (CH ₂ ) ₄ H 1-5 H Ph ( CH ₂ ) ₅ H 1-6 2-Cl Ph (CH ₂ ) ₅ H 1-7 3-Cl Ph (CH ₂ ) ₅ H 1-8 4-Cl Ph (CH ₂ ) ₅ H 1-9 4-Br Ph (CH ₂ ) ₅ H 1-10 4-I Ph (CH ₂ ) ₅ H 1-11 4-F Ph (CH ₂ ) ₅ H 1-12 4-CH ₃ Ph (CH ₂ ) ₅ H 1-13 4-CF ₃ Ph (CH ₂ ) ₅ H 1-14 4-OH Ph (CH ₂ ) ₅ H 1-15 4-MeO Ph (CH ₂ ) ₅ H 1-16 4-Me (CH ₂ ) ₄ CH ₂ O Ph (CH ₂ ) ₅ H 1-17 4-cHexCH ₂ O Ph (CH ₂ ) ₅ H 1-18 4-Ph Ph (CH ₂ ) ₅ H 1-19 4-PhO Ph (CH ₂ ) ₅ H 1 -20 4-PhCH ₂ O Ph (CH ₂ ) ₅ H 1-21 4- (2-MeOBnO) Ph (CH ₂ ) ₅ H 1-22 4- (3-MeOBnO) Ph (CH ₂ ) ₅ H 1- 23 4- (4-MeOBnO) Ph (CH ₂ ) ₅ H 1-24 3-PhCH ₂ O Ph (CH ₂ ) ₅ H 1-25 2-PhCH ₂ O Ph (CH ₂ ) ₅ H 1-26 4- (4-ClPhC H ₂ O) Ph (CH ₂ ) ₅ H 1-27 4- (4-MePhCHMeO) Ph (CH ₂ ) ₅ H 1-28 4-PhCH ₂ CH ₂ O Ph (CH ₂ ) ₅ H 1-29 4- PhCH ₂ CH ₂ CH ₂ O Ph (CH ₂ ) ₅ H 1-30 4-PhOCH ₂ Ph (CH ₂ ) ₅ H 1-31 4-PhOCHMe Ph (CH ₂ ) ₅ H 1-32 4-PhCH ₂ OCH ₂ Ph (CH ₂ ) ₅ H 1-33 4-PhCH ₂ CH ₂ Ph (CH ₂ ) ₅ H 1-34 4-PhCH ₂ CHOH Ph (CH ₂ ) ₅ H 1-35 4-PhCH ₂ C = O Ph ( CH ₂ ) ₅ H 1-36 4-PhCH (Me) O Ph (CH ₂ ) ₅ H 1-37 4- (4-FPhCH ₂ O) Ph (CH ₂ ) ₅ H 1-38 3,4-F ₂ Ph (CH ₂ ) ₅ H 1-39 3,4- (CH ₃ O) ₂ Ph (CH ₂ ) ₅ H 1-40 4-PhCH ₂ O, 3-F Ph (CH ₂ ) ₅ H 1-41 4 -PhCH ₂ O, 3-MeO Ph (CH ₂ ) ₅ H 1-42 4-Cl Ph (CH ₂ ) ₆ H 1-43 4-Cl Ph (CH ₂ ) ₇ H 1-44 4- (2-PyrCH ₂ O) Ph (CH ₂ ) ₅ H 1-45 4- (3-PyrCH ₂ O) Ph (CH ₂ ) ₅ H 1-46 4- (4-PyrCH ₂ O) Ph (CH ₂ ) ₅ H 1- 47 4- (2-PymCH ₂ O) Ph (CH ₂ ) ₅ H 1-48 4- (4-PymCH ₂ O) Ph (CH ₂ ) ₅ H 1-49 4- (2-PyzCH ₂ O) Ph ( CH ₂ ) ₅ H 1-50 4- (2-ThiCH ₂ O) Ph (CH ₂ ) ₅ H 1-51 4- (3-ThiCH ₂ O) Ph (CH ₂ ) ₅ H 1-52 4- (2 -ThiCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-53 4- (3-ThiCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-54 4- (2-FurCH ₂ O) Ph (CH ₂ ) ₅ H 1-55 4- (2- FurCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-56 4- (3-FurCH ₂ O) Ph (CH ₂ ) ₅ H 1-57 4- (4-ThizCH ₂ O) Ph (CH ₂ ) ₅ H 1-58 4- (5-ThizCH ₂ O) Ph (CH ₂ ) ₅ H 1-59 4- (2-ThizCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-60 4- (4-ThizCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-61 4- (5-ThizCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-62 4- (2-OxaCH ₂ O) Ph (CH ₂ ) ₅ H 1-63 4- (4-OxaCH ₂ O) Ph (CH ₂ ) ₅ H 1-64 4- (5-OxaCH ₂ O) Ph (CH ₂ ) ₅ H 1-65 4- (5-Me- 2-Me-4-OxaCH ₂ O) Ph (CH ₂ ) ₅ H 1-66 4- (5-Me-2-Me-4-OxaCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-67 4 -(5-Me-2-Me-4-ThizCH ₂ O) Ph (CH ₂ ) ₅ H 1-68 4- (5-Me-2-Me-4-ThizCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-69 4- (3-Me-5-Me-4-IsoxCH ₂ O) Ph (CH ₂ ) ₅ H 1-70 4- (2-PyrCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-71 4- (3-PyrCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-72 4- (4-PyrCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-73 2-F, 4 -(PhCH ₂ O) Ph (CH ₂ ) ₅ H 1-74 2-F, 4- (2-ThiCH ₂ O) Ph (CH ₂ ) ₅ H 1-75 3-Cl-4- (2-ThizCH ₂ O) Ph (CH ₂ ) ₅ H 1-76 3-Me-4- (PhCH ₂ O) Ph (CH ₂ ) ₅ H 1-77 3-Me-4- (2-ThiCH ₂ O) Ph (CH ₂ ) ₅ H 1-78 3-Me-4- (2-ThizCH ₂ O) Ph (CH ₂ ) ₅ H 1-79 3-MeO-4- (2-Thi (CH ₂ O) Ph (CH ₂ ) ₅ H 1-80 3-MeO-4- (2-ThizCH ₂ O) Ph (CH ₂ ) ₅ H 1-81 4- (CH ₂ = CH-CH ₂ ) Ph ( CH ₂ ) ₅ H 1-82 4- (Me-CH = CH) Ph (CH ₂ ) ₅ H 1-83 4- [Me-C (Me) = CH-CH ₂ ] Ph (CH ₂ ) ₅ H 1 -84 4- [CH ₂ = CH-CH (Me)] Ph (CH ₂ ) ₅ H 1-85 4- (1-NpCH ₂ ) Ph (CH ₂ ) ₅ H 1-86 4- (2-NpCH ₂ ) Ph (CH ₂ ) ₅ H 1-87 4- (2-ThizCH ₂ O) Ph (CH ₂ ) ₅ H 1-88 4- (5-ThizCH ₂ O) Ph (CH ₂ ) ₅ H 1-89 4 -(2-MeOBnO) Ph (CH ₂ ) ₅ H 1-90 4- (3-MeOBnO) Ph (CH ₂ ) ₅ H 1-91 4- (4-MeOBnO) Ph (CH ₂ ) ₅ H 1-92 2- (BzCH ₂ O) Ph (CH ₂ ) ₅ H 1-93 3- (BzCH ₂ O) Ph (CH ₂ ) ₅ H 1-94 4- (BzCH ₂ O) Ph (CH ₂ ) ₅ H 1- 95 2- (2-OH-2-Ph-CH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-96 3- (2-OH-2-Ph-CH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-97 4- (2-OH-2-Ph-CH ₂ CH ₂ O) Ph (CH ₂ ) ₅ H 1-98 2-[(2-Thi) C = O-CH ₂ O] Ph ( CH ₂ ) ₅ H 1-99 3-[(2-Thi) C = O-CH ₂ O] Ph (CH ₂ ) ₅ H 1-100 4-[(2-Thi) C = O-CH ₂ O] Ph (CH ₂ ) ₅ H 1-101 2- [2-OH-2- (2-Thi) -CH ₂ CH ₂ O] Ph (CH ₂ ) ₅ H 1-102 3- [2-OH-2- (2-Thi) -CH ₂ CH ₂ O] Ph (CH ₂ ) ₅ H 1-103 4- [2-OH-2- (2-Thi) -CH ₂ CH ₂ O] Ph (CH ₂ ) ₅ H 1-104 4- [5- (2-Me) Th i-CH ₂ O] Ph (CH ₂ ) ₅ H 1-105 4- [2- (4- [2-Ph-5-Me] Oxa) -CH ₂ CH ₂ O] Ph (CH ₂ ) ₅ H 1 -106 4- [4- (2-Ph) Thiz-CH ₂ O] Ph (CH ₂ ) ₅ H 1-107 4- [2- (3-Me) Thi-CH ₂ O] Ph (CH ₂ ) ₅ H 1-108 2- (HOOC-CH ₂ O) Ph (CH ₂ ) ₅ H 1-109 3- (HOOC-CH ₂ O) Ph (CH ₂ ) ₅ H 1-110 4- (HOOC-CH ₂ O ) Ph (CH ₂ ) ₅ H 1-111 2-Bz Ph (CH ₂ ) ₅ H 1-112 3-Bz Ph (CH ₂ ) ₅ H 1-113 4-Bz Ph (CH ₂ ) ₅ H 1-114 4- (2-MeO-PhO) Ph (CH ₂ ) ₅ H 1-115 4- (3-MeO-PhO) Ph (CH ₂ ) ₅ H 1-116 4- (4-MeO-PhO) Ph (CH ₂ ) ₅ H 1-117 4-Cl Ph (CH ₂ ) ₃ Ac 1-118 4-PhCH ₂ O Ph (CH ₂ ) ₃ Ac 1-119 4-Cl Ph (CH ₂ ) ₄ Ac 1-120 4- PhCH ₂ O Ph (CH ₂ ) ₄ Ac 1-121 H Ph (CH ₂ ) ₅ Ac 1-122 4-Cl Ph (CH ₂ ) ₅ Ac 1-123 4-OH Ph (CH ₂ ) ₅ Ac 1-124 4-MeO Ph (CH ₂ ) ₅ Ac 1-125 4-Me (CH ₂ ) ₄ CH ₂ O Ph (CH ₂ ) ₅ Ac 1-126 4-cHexCH ₂ O Ph (CH ₂ ) ₅ Ac 1-127 4 -Ph Ph (CH ₂ ) ₅ Ac 1-128 4-PhO Ph (CH ₂ ) ₅ Ac 1-129 2-PhCH ₂ O Ph (CH ₂ ) ₅ Ac 1-130 4- (4-ClPhCH ₂ O) Ph (CH ₂ ) ₅ Ac 1-131 4- (4-MePhCHMeO) Ph (CH ₂ ) ₅ Ac 1-132 4-PhCH ₂ CH ₂ O Ph (CH ₂ ) ₅ Ac 1-133 4-PhCH ₂ CH ₂ CH ₂ O Ph (CH ₂ ) ₅ Ac 1-134 4-PhOCH ₂ Ph (CH ₂ ) ₅ Ac 1-135 4-PhCH ₂ OCH ₂ Ph (CH ₂ ) ₅ Ac 1-136 4-PhCH ₂ CH ₂ Ph (CH ₂ ) ₅ Ac 1-137 4-PhCH ₂ CHOH Ph (CH ₂ ) ₅ Ac 1-138 4-PhCH ₂ C = O Ph (CH ₂ ) ₅ Ac 1-139 4-Cl Ph (CH ₂ ) ₆ Ac 1- 140 4-Cl Ph (CH ₂ ) ₇ Ac 1-141 4- (4-PyrCH ₂ O) Ph (CH ₂ ) ₅ Ac 1-142 4- (2-ThiCH ₂ O) Ph (CH ₂ ) ₅ Ac 1 -143 4- (2-ThiCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ Ac 1-144 4- (2-FurCH ₂ O) Ph (CH ₂ ) ₅ Ac 1-145 4- (4-ThizCH ₂ O ) Ph (CH ₂ ) ₅ Ac 1-146 4- (2-PyrCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ Ac 1-147 4-Cl Ph (CH ₂ ) ₃ CONHPh 1-148 4-PhCH ₂ O Ph (CH ₂ ) ₃ CONHPh 1-149 4-Cl Ph (CH ₂ ) ₄ CONHPh 1-150 4-PhCH ₂ O Ph (CH ₂ ) ₄ CONHPh 1-151 H Ph (CH ₂ ) ₅ CONHPh 1-152 4 -Cl Ph (CH ₂ ) ₅ CONHPh 1-153 4-OH Ph (CH ₂ ) ₅ CONHPh 1-154 4-MeO Ph (CH ₂ ) ₅ CONHPh 1-155 4-Me (CH ₂ ) ₄ CH ₂ O Ph (CH ₂ ) ₅ CONHPh 1-156 4-cHexCH ₂ O Ph (CH ₂ ) ₅ CONHPh 1-157 4-Ph Ph (CH ₂ ) ₅ CONHPh 1-158 4-PhO Ph (CH ₂ ) ₅ CONHPh 1-159 2-PhCH ₂ O Ph (CH ₂ ) ₅ CONHPh 1-160 4- (4-ClPhCH ₂ O) Ph (CH ₂ ) ₅ CONHPh 1-161 4- (4-MePhCHMeO) Ph (CH ₂ ) ₅ CONHPh 1-162 4-PhCH ₂ CH ₂ O Ph (CH ₂ ) ₅ CONHPh 1-163 4-PhCH ₂ CH ₂ CH ₂ O Ph (CH ₂ ) ₅ CONHPh 1-164 4-PhOCH ₂ Ph (CH ₂ ) ₅ CONHPh 1-165 4-PhCH ₂ OCH ₂ Ph (CH ₂ ) ₅ CONHPh 1-166 4-PhCH ₂ CH ₂ Ph (CH ₂ ) ₅ CONHPh 1-167 4-PhCH ₂ CHOH Ph (CH ₂ ) ₅ CONHPh 1-168 4-PhCH ₂ C = O Ph (CH ₂ ) ₅ CONHPh 1-169 4-Cl Ph (CH ₂ ) ₆ CONHPh 1-170 4-Cl Ph (CH ₂ ) ₇ CONHPh 1-171 4- ( 4-PyrCH ₂ O) Ph (CH ₂ ) ₅ CONHPh 1-172 4- (2-ThiCH ₂ O) Ph (CH ₂ ) ₅ CONHPh 1-173 4- (2-ThiCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ CONHPh 1-174 4- (2-FurCH ₂ O) Ph (CH ₂ ) ₅ CONHPh 1-175 4- (4-ThizCH ₂ O) Ph (CH ₂ ) ₅ CONHPh 1-176 4- (2-PyrCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ CONHPh 1-177 4- (2-FPhCH ₂ O) Ph (CH ₂ ) ₅ H 1-178 4- (3-FPhCH ₂ O) Ph (CH ₂ ) ₅ H ───────────────────────────────

[0106]

Embedded image

[0107]

X represents a single bond. 例 示 Exemplified compound Substituent A on ring A W- X-Y R number ───────────────────────────── 2-1 6-Cl 2-Np (CH ₂ ) ₃ H 2 -2 6-PhCH ₂ O 2-Np (CH ₂ ) ₃ H 2-3 6-Cl 2-Np (CH ₂ ) ₄ H 2-4 6-PhCH ₂ O 2-Np (CH ₂ ) ₄ H 2- 5 H 2-Np (CH ₂ ) ₅ H 2-6 4-Cl 2-Np (CH ₂ ) ₅ H 2-7 6-Cl 2-Np (CH ₂ ) ₅ H 2-8 7-Cl 2-Np (CH ₂ ) ₅ H 2-9 6-Br 2-Np (CH ₂ ) ₅ H 2-10 6-I 2-Np (CH ₂ ) ₅ H 2-11 6-F 2-Np (CH ₂ ) ₅ H 2-12 6-CH ₃ 2-Np (CH ₂ ) ₅ H 2-13 6-CF ₃ 2-Np (CH ₂ ) ₅ H 2-14 6-OH 2-Np (CH ₂ ) ₅ H 2- 15 6-MeO 2-Np (CH ₂ ) ₅ H 2-16 6-Me (CH ₂ ) ₅ CH ₂ O 2-Np (CH ₂ ) ₅ H 2-17 6-cHexMeO 2-Np (CH ₂ ) ₅ H 2-18 6-Ph 2-Np (CH ₂ ) ₅ H 2-19 6-PhO 2-Np (CH ₂ ) ₅ H 2-20 6-PhCH ₂ O 2-Np (CH ₂ ) ₅ H 2- 21 4-PhCH ₂ O 2-Np (CH ₂ ) ₅ H 2-22 7-PhCH ₂ O 2-Np (CH ₂ ) ₅ H 2-23 8-PhCH ₂ O 2-Np (CH ₂ ) ₅ H 2 -24 6- (4-ClPhCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-25 6- (4-MeP hCHMeO) 2-Np (CH ₂ ) ₅ H 2-26 6-PhCH ₂ CH ₂ O 2-Np (CH ₂ ) ₅ H 2-27 6-PhCH ₂ CH ₂ CH ₂ O 2-Np (CH ₂ ) ₅ H 2-28 6-PhOCH ₂ 2-Np (CH ₂ ) ₅ H 2-29 6-PhOCHMe 2-Np (CH ₂ ) ₅ H 2-30 6-PhCH (Me) O 2-Np (CH ₂ ) ₅ H 2-31 6,7-Cl ₂ 2-Np (CH ₂ ) ₅ H 2-32 6,7-F ₂ 2-Np (CH ₂ ) ₅ H 2-33 6,7- (CH ₃ O) ₂ 2-Np (CH ₂ ) ₅ H 2-34 6-PhCH ₂ O-7-F 2-Np (CH ₂ ) ₅ H 2-35 6-PhCH ₂ O-7-CH ₃ O 2-Np (CH ₂ ) ₅ H 2-36 6-Cl 2-Np (CH ₂ ) ₆ H 2-37 6-Cl 2-Np (CH ₂ ) ₇ H 2-38 6- (2-PyrCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-39 6- (3-PyrCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-40 6- (4-PyrCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-41 6 -(2-ThiCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-42 6- (3-ThiCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-43 6- (2-FurCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-44 6- (3-FurCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-45 6- (2-ThizCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-46 6- (4-ThizCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-47 6- (5-ThizCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-48 6- (2 -ThizCH ₂ CH ₂ O) 2-Np (CH ₂ ) ₅ H 2-49 6- (4-ThizCH ₂ CH ₂ O) 2-Np (CH ₂ ) ₅ H 2-50 6- (5-ThizCH ₂ CH ₂ O) 2-Np (CH ₂ ) ₅ H 2-51 6- (2-OxaCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-52 6- (4-Ox aCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-53 6- (5-OxaCH ₂ O) 2-Np (CH ₂ ) ₅ H 2-54 6- (2-PyrCH ₂ CH ₂ O) 2- Np (CH ₂ ) ₅ H 2-55 6- (3-PyrCH ₂ CH ₂ O) 2-Np (CH ₂ ) ₅ H 2-56 6- (4-PyrCH ₂ CH ₂ O) 2-Np (CH ₂ ) ₅ H 2-57 6- (CH ₂ = CH-CH ₂ ) 2-Np (CH ₂ ) ₅ H 2-58 6- (Me-CH = CH) 2-Np (CH ₂ ) ₅ H 2-59 6- [Me-C (Me) = CH-CH ₂ ] 2-Np (CH ₂ ) ₅ H 2-60 6- [CH ₂ = CH-CH (Me)] 2-Np (CH ₂ ) ₅ H 2 -61 H 2-Np (CH ₂ ) ₅ Ac 2-62 6-CH ₃ 2-Np (CH ₂ ) ₅ Ac 2-63 6-CF ₃ 2-Np (CH ₂ ) ₅ Ac 2-64 6-PhCH ₂ O 2-Np (CH ₂ ) ₅ Ac 2-65 6-Cl 2-Np (CH ₂ ) ₅ Ac 2-66 6- (4-PyrCH ₂ O) 2-Np (CH ₂ ) ₅ Ac 2-67 H 2-Np (CH ₂ ) ₅ CONHPh 2-68 6-CH ₃ 2-Np (CH ₂ ) ₅ CONHPh 2-69 6-CF ₃ 2-Np (CH ₂ ) ₅ CONHPh 2-70 6-PhCH ₂ O 2-Np (CH ₂ ) ₅ CONHPh 2-71 6-Cl 2-Np (CH ₂ ) ₅ CONHPh 2-72 6- (4-PyrCH ₂ O) 2-Np (CH ₂ ) ₅ CONHPh ───── ────────────────────────

[0108]

Embedded image

[0109]

[Table 3] X represents a single bond ─────────────────────────── Exemplified compound Substituent on ring A A W-X- Y R number ─────────────────────────── 3-1 5-Cl 2-Pyr (CH ₂ ) ₅ H 3-2 H 2 -Pyr (CH ₂ ) ₅ H 3-3 H 3-Pyr (CH ₂ ) ₅ H 3-4 4-PhCH ₂ O 2-Pyr (CH ₂ ) ₅ H 3-5 5-PhCH ₂ O 2-Pyr ( CH ₂ ) ₅ H 3-6 4-Cl 2-Thi (CH ₂ ) ₅ H 3-7 5-Cl 2-Thi (CH ₂ ) ₅ H 3-8 4-PhCH ₂ O 2-Thi (CH ₂ ) ₅ H 3-9 5-PhCH ₂ O 2-Thi (CH ₂ ) ₅ H 3-10 H 2-Fur (CH ₂ ) ₅ H 3-11 H 3-Fur (CH ₂ ) ₅ H 3-12 H 3 -Pyr (CH ₂ ) ₅ Ac 3-13 5-Cl 2-Pyr (CH ₂ ) ₅ Ac 3-14 5-PhCH ₂ O 2-Pyr (CH ₂ ) ₅ Ac 3-15 5-Cl 2-Thi ( CH ₂ ) ₅ Ac 3-16 5-PhCH ₂ O 2-Thi (CH ₂ ) ₅ Ac 3-17 H 3-Fur (CH ₂ ) ₅ Ac 3-18 H 3-Pyr (CH ₂ ) ₅ CONHPh 3- 19 5-Cl 2-Pyr (CH ₂ ) ₅ CONHPh 3-20 5-PhCH ₂ O 2-Pyr (CH ₂ ) ₅ CONHPh 3-21 5-Cl 2-Thi (CH ₂ ) ₅ CONHPh 3-22 5- PhCH ₂ O 2-Thi (CH ₂ ) ₅ CONHPh 3-23 H 3-Fur (CH ₂ ) ₅ CONHPh ───────────── ──────────────

[0110]

Embedded image

[0111]

[Table 4] X represents a single bond ──────────────────────────────── Exemplified compound Substituent on ring A A W-X-Y R number ──────────────────────────────── 4-1 H 2-Bthi (CH ₂ ) ₅ H 4-2 H 3-Bthi (CH ₂ ) ₅ H 4-3 H 2-Quin (CH ₂ ) ₅ H 4-4 7-Cl 3-Quin (CH ₂ ) ₅ H 4-5 H 2- Bfur (CH ₂ ) ₅ H 4-6 6-Me 3-Bfur (CH ₂ ) ₅ H 4-7 5-PhCH ₂ O 2-Bthi (CH ₂ ) ₅ H 4-8 6-PhCH ₂ O 3-Bthi (CH ₂ ) ₅ H 4-9 6-PhCH ₂ O 2-Quin (CH ₂ ) ₅ H 4-10 7-PhCH ₂ O 3-Quin (CH ₂ ) ₅ H 4-11 5-PhCH ₂ O 2- Bfur (CH ₂ ) ₅ H 4-12 6-PhCH ₂ O 3-Bfur (CH ₂ ) ₅ H 4-13 H 2,3-dHBfur-5-yl (CH ₂ ) ₅ H 4-14 H 3-Bthi (CH ₂ ) ₅ Ac 4-15 H 2-Quin (CH ₂ ) ₅ Ac 4-16 H 2-Bfur (CH ₂ ) ₅ Ac 4-17 H 2,3-dHBfur-5-yl (CH ₂ ) ₅ Ac 4-18 H 3-Bthi (CH ₂ ) ₅ CONHPh 4-19 H 2-Quin (CH ₂ ) ₅ CONHPh 4-20 H 2-Bfur (CH ₂ ) ₅ CONHPh 4-21 H 2,3-dHBfur- 5-yl (CH ₂ ) ₅ CONHPh 4-22 2-Bz 5-Bfur (CH ₂ ) ₅ H ───────── ───────────────────────

[0112]

Embedded image

[0113]

Table 5 Example Compound on Ring A Substituent A W XY R Number ────────────────────────────── 5-1 4-Cl Ph-O (CH ₂ ) ₄ H 5-2 4- Br Ph-O (CH ₂ ) ₄ H 5-3 4-I Ph-O (CH ₂ ) ₄ H 5-4 4-F Ph-O (CH ₂ ) ₄ H 5-5 4-CH ₃ Ph-O (CH ₂ ) ₄ H 5-6 4-CF ₃ Ph-O (CH ₂ ) ₄ H 5-7 4-OH Ph-O (CH ₂ ) ₄ H 5-8 4-MeO Ph-O (CH ₂ ) ₄ H 5-9 4-Me (CH ₂ ) ₅ CH ₂ O Ph-O (CH ₂ ) ₄ H 5-10 4-cHexCH ₂ O Ph-O (CH ₂ ) ₄ H 5-11 4-Ph Ph- O (CH ₂ ) ₄ H 5-12 4-PhO Ph-O (CH ₂ ) ₄ H 5-13 4-PhCH ₂ O Ph-O (CH ₂ ) ₄ H 5-14 3-PhCH ₂ O Ph-O (CH ₂ ) ₄ H 5-15 2-PhCH ₂ O Ph-O (CH ₂ ) ₄ H 5-16 4- (4-ClPhCH ₂ O) Ph-O (CH ₂ ) ₄ H 5-17 4- ( 4-MePhCHMeO) Ph-O (CH ₂ ) ₄ H 5-18 4-PhCH ₂ CH ₂ O Ph-O (CH ₂ ) ₄ H 5-19 4-PhCH ₂ CH ₂ CH ₂ O Ph-O (CH ₂ ) ₄ H 5-20 4-PhOCH ₂ Ph-O (CH ₂ ) ₄ H 5-21 4-PhOCHMe Ph-O (CH ₂ ) ₄ H 5-22 4-PhCH (Me) O Ph-O (C H ₂ ) ₄ H 5-23 3,4-Cl ₂ Ph-O (CH ₂ ) ₄ H 5-24 3,4-F ₂ Ph-O (CH ₂ ) ₄ H 5-25 3,4- (CH ₃ O) ₂ Ph-O (CH ₂ ) ₄ H 5-26 4-PhCH ₂ O, 3-F Ph-O (CH ₂ ) ₄ H 5-27 4-PhCH ₂ O, 3-CH ₃ O Ph- O (CH ₂ ) ₄ H 5-28 4-Cl Ph-O (CH ₂ ) ₆ H 5-29 4-F Ph-O (CH ₂ ) ₆ H 5-30 4-I Ph-O (CH ₂ ) ₆ H 5-31 4-Ph Ph-O (CH ₂ ) ₆ H 5-32 4-Cl Ph CH ₂ O (CH ₂ ) ₄ H 5-33 H Ph CH ₂ O (CH ₂ ) ₅ H 5-34 4- (2-PyrCH ₂ O) Ph-O (CH ₂ ) ₄ H 5-35 4- (3-PyrCH ₂ O) Ph-O (CH ₂ ) ₄ H 5-36 4- (4-PyrCH ₂ O ) Ph-O (CH ₂ ) ₄ H 5-37 4- (2-ThiCH ₂ O) Ph-O (CH ₂ ) ₄ H 5-38 4- (3-ThiCH ₂ O) Ph-O (CH ₂ ) ₄ H 5-39 4- (2-FurCH ₂ O) Ph-O (CH ₂ ) ₄ H 5-40 4- (3-FurCH ₂ O) Ph-O (CH ₂ ) ₄ H 5-41 4- ( 2-ThizCH ₂ O) Ph-O (CH ₂ ) ₄ H 5-42 4- (4-ThizCH ₂ eO) Ph-O (CH ₂ ) ₄ H 5-43 4- (5-ThizCH ₂ O) Ph- O (CH ₂ ) ₄ H 5-44 4- (2-OxaCH ₂ eO) Ph-O (CH ₂ ) ₄ H 5-45 4- (4-OxaCH ₂ O) Ph-O (CH ₂ ) ₄ H 5 -46 4- (5-OxaCH ₂ O) Ph-O (CH ₂ ) ₄ H 5-47 4- (2-PyrCH ₂ CH ₂ O) Ph-O (CH ₂ ) ₄ H 5-48 4- (3 -PyrCH ₂ CH ₂ O) Ph-O (CH ₂ ) ₄ H 5-49 4- (4-Pyr CH ₂ CH ₂ O) Ph-O (CH ₂ ) ₄ H 5-50 4- (CH ₂ = CH-CH ₂ ) Ph-O (CH ₂ ) ₄ H 5-51 4- (Me-CH = CH) Ph-O (CH ₂ ) ₄ H 5-52 4- [Me-C (Me) = CH-CH ₂ ] Ph-O (CH ₂ ) ₄ H 5-53 4- [CH ₂ = CH-CH (Me )] Ph-O (CH ₂ ) ₄ H 5-54 4-Cl Ph-O (CH ₂ ) ₄ Ac 5-55 4-I Ph-O (CH ₂ ) ₄ Ac 5-56 4-Ph Ph-O (CH ₂ ) ₄ Ac 5-57 4-PhCH ₂ O Ph-O (CH ₂ ) ₄ Ac 5-58 4- (4-ClPhCH ₂ O) Ph-O (CH ₂ ) ₄ Ac 5-59 4-Cl Ph-O (CH ₂ ) ₆ Ac 5-60 4-F Ph-O (CH ₂ ) ₆ Ac 5-61 4-I Ph-O (CH ₂ ) ₆ Ac 5-62 4-Ph Ph-O (CH ₂ ) ₆ Ac 5-63 4-Cl Ph CH ₂ O (CH ₂ ) ₄ Ac 5-64 H Ph CH ₂ O (CH ₂ ) ₅ Ac 5-65 4-PhCH ₂ O, 2-Me Ph-O ( CH ₂ ) ₄ H 5-66 3- (2-ThiCH ₂ O) Ph-O (CH ₂ ) ₄ H 5-67 3-Me-4- (PhCH ₂ O) Ph-O (CH ₂ ) ₄ H ─ ──────────────────────────────

[0114]

Embedded image

[0115]

Table 6 Example Compound on Ring A Substituent A W XY R Number ────────────────────────────── 6-1 6-Cl 2-Np-O (CH ₂ ) ₄ H 6-2 4-Br 2-Np-O (CH ₂ ) ₄ H 6-3 7-I 2-Np-O (CH ₂ ) ₄ H 6-4 6-F 2-Np-O (CH ₂ ) ₄ H 6- 5 6-CH ₃ 2-Np-O (CH ₂ ) ₄ H 6-6 6-CF ₃ 2-Np-O (CH ₂ ) ₄ H 6-7 6-OH 2-Np-O (CH ₂ ) ₄ H 6-8 6-MeO 2-Np-O (CH ₂ ) ₄ H 6-9 6-Me (CH ₂ ) ₅ CH ₂ O 2-Np-O (CH ₂ ) ₄ H 6-10 6-cHexCH ₂ O 2-Np-O (CH ₂ ) ₄ H 6-11 6-Ph 2-Np-O (CH ₂ ) ₄ H 6-12 6-PhO 2-Np-O (CH ₂ ) ₄ H 6-13 6 -PhCH ₂ O 2-Np-O (CH ₂ ) ₄ H 6-14 7-PhCH ₂ O 2-Np-O (CH ₂ ) ₄ H 6-15 4-PhCH ₂ O 2-Np-O (CH ₂ ) ₄ H 6-16 6- (4-ClPhCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-17 6- (4-MePhCHMeO) 2-Np-O (CH ₂ ) ₄ H 6-18 6-PhCH ₂ CH ₂ O 2-Np-O (CH ₂ ) ₄ H 6-19 6-PhCH ₂ CH ₂ CH ₂ O 2-Np-O (CH ₂ ) ₄ H 6-20 6-PhOCH ₂ 2- Np-O (CH ₂ ) ₄ H 6-21 6-PhOCHMe 2-Np -O (CH ₂ ) ₄ H 6-22 6-PhCH (Me) O 2-Np-O (CH ₂ ) ₄ H 6-23 H 2-Np-O (CH ₂ ) ₄ H 6-24 6,7 -Cl ₂ 2-Np-O (CH ₂ ) ₄ H 6-25 6,7-F ₂ 2-Np-O (CH ₂ ) ₄ H 6-26 6,7- (CH ₃ O) ₂ 2-Np -O (CH ₂ ) ₄ H 6-27 6-PhCH ₂ O, 3-F 2-Np-O (CH ₂ ) ₄ H 6-28 6-PhCH ₂ O, 7-CH ₃ O 2-Np-O (CH ₂ ) ₄ H 6-29 6-Cl 2-Np-O (CH ₂ ) ₆ H 6-30 6-F 2-Np-O (CH ₂ ) ₆ H 6-31 H 1-Np-O ( CH ₂ ) ₆ H 6-32 6-Ph 2-Np-O (CH ₂ ) ₆ H 6-33 6-Cl 2-Np CH ₂ O (CH ₂ ) ₄ H 6-34 H 2-Np CH ₂ O (CH ₂ ) ₅ H 6-35 6- (2-PyrCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-36 6- (3-PyrCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-37 6- (4-PyrCH ₂ O) 2-Np -O (CH ₂ ) ₄ H 6-38 6- (2-ThiCH ₂ O) 2-Np -O (CH ₂ ) ₄ H 6- 39 6- (3-ThiCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-40 6- (2-FurCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-41 6- ( 3-FurCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-42 6- (2-ThizCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-43 6- (4-ThizCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-44 6- (5-ThizCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-45 6- (2-OxaCH ₂ O) 2- Np-O (CH ₂ ) ₄ H 6-46 6- (4-OxaCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-47 6- (5-OxaCH ₂ O) 2-Np-O (CH ₂ ) ₄ H 6-48 6- (2-PyrCH ₂ CH ₂ O) 2-Np -O (CH ₂ ) ₄ H 6-49 6- (3-PyrCH ₂ CH ₂ O) 2-Np -O (CH ₂ ) ₄ H 6-50 6- (4-PyrCH ₂ CH ₂ O) 2-Np -O (CH ₂ ) ₄ H 6-51 6- (CH ₂ = CH-CH ₂ ) 2-Np -O (CH ₂ ) ₄ H 6-52 6- (Me-CH = CH) 2-Np-O (CH ₂ ) ₄ H 6-53 6- [Me-C (Me) = CH-CH ₂ ] 2-Np -O (CH ₂ ) ₄ H 6-54 6- [CH ₂ = CH-CH (Me)] 2-Np-O (CH ₂ ) ₄ H 6-55 H 2-Np-O (CH ₂ ) ₄ Ac 6-56 H 1-Np-O (CH ₂ ) ₆ Ac ───────────────────────────────

[0116]

Embedded image

[0117]

Table 7 Example Compound on ring A Substituent A W XY R number ──────────────────── 7-1 H 2-Pyr-O (CH ₂ ) ₄ H 7-2 H 3-Pyr-O (CH ₂ ) ₄ H 7-3 H 4-Pyr-O (CH ₂ ) ₄ H 7-4 4-Cl 2-Thi-O (CH ₂ ) ₄ H 7-5 H 3-Thi-O (CH ₂ ) ₄ H 7-6 H 2-Pyr-O (CH ₂ ) ₄ Ac 7-7 H 2-Thi-O (CH ₂ ) ₄ Ac ─────────────────────── ───

[0118]

Embedded image

[0119]

[Table 8] ────────────────────────────────── Exemplified compound Substituent A on ring A A W X Y R number ────────────────────────────────── 8-1 H 2-Bthi-O (CH ₂ ) ₄ H 8-2 H 3-Bthi-O (CH ₂ ) ₄ H 8-3 H 2-Quin-O (CH ₂ ) ₄ H 8-4 4-Cl 3-Quin-O (CH ₂ ) ₄ H 8- 5 H 2-Bfur-O (CH ₂ ) ₄ H 8-6 4-Me 3-Bfur-O (CH ₂ ) ₄ H 8-7 H 2,3-dHBfur-5-yl-O (CH ₂ ) ₄ H 8-8 H 3-Bthi-O (CH ₂ ) ₄ Ac 8-9 H 2-Quin-O (CH ₂ ) ₄ Ac 8-10 H 2-Bfur-O (CH ₂ ) ₄ Ac 8-11 H 2,3-dHBfur-5-yl-O (CH ₂ ) ₄ Ac ─────────────────────────────────に お い て In the above table, (1) preferably exemplified compound numbers 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7,
1-8, 1-11, 1-13, 1-14, 1-15, 1-1
6, 1-17, 1-18, 1-19, 1-20, 1-21,
1-22, 1-24, 1-26, 1-27, 1-28, 1-2
9, 1-30, 1-31, 1-32, 1-33, 1-34,
1-35, 1-36, 1-37, 1-38, 1-40, 1-4
1, 1-42, 1-43, 1-44, 1-45, 1-46,
1-47, 1-48, 1-49, 1-50, 1-51, 1-5
2, 1-53, 1-54, 1-56, 1-57, 1-58,
1-59, 1-62, 1-63, 1-65, 1-67, 1-6
9, 1-70, 1-71, 1-73, 1-74, 1-76,
1-77, 1-78, 1-79, 1-80, 1-83, 1-8
7, 1-90, 1-94, 1-97, 1-99, 1-10
0, 1-102, 1-103, 1-104, 1-105, 1
-106, 1-107, 1-108, 1-110, 1-11
1, 1-112, 1-113, 1-114, 1-115, 2
-4, 2-5, 2-7, 2-11, 2-13, 2-20, 2-
21, 2-22, 2-23, 2-26, 2-28, 2-3
4,2-35,2-38,2-39,2-40,2-41,
2-42, 2-43, 2-44, 2-45, 2-46, 2.4
7, 2-51, 2-52, 2-53, 2-63, 2-64,
2-66, 2-70, 2-72, 3-1, 3-3,3-4,3
-5, 3-6, 3-7, 3-8, 3-9, 3-13, 3-1
4, 3-15, 3-16, 3-18, 3-19, 3-20,
3-21, 3-22, 4-1, 4-3, 4-4, 4-6, 4-
8, 4-9, 4-12, 4-13, 4-19, 4-20, 4-
21, 4-22, 5-1, 5-3, 5-6, 5-11, 5-1
2, 5-13, 5-14, 5-15, 5-16, 5-18,
5-20, 5-26, 5-27, 5-28, 5-29, 5-3
0, 5-31, 5-32, 5-33, 5-34, 5-35,
5-36, 5-37, 5-38, 5-39, 5-40, 5-4
1, 5-42, 5-43, 5-44, 5-45, 5-46,
5-47, 5-57, 5-59, 5-60, 5-61, 5-6
3,5-65,5-66,5-67,6-1,6-4,6-
5, 6-6, 6-12, 6-13, 6-14, 6-18, 6-
20, 6-23, 6-27, 6-28, 6-31, 6-3
3, 6-35, 6-36, 6-38, 6-39, 6-40,
6-42, 6-43, 6-44, 6-46, 7-1, 7-2,
Compounds of 7-3, 7-4, 7-5, 8-1, 8-3, 8-5, 8-7. (2) More preferably, the exemplified compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7,
1-8, 1-14, 1-15, 1-16, 1-17, 1-1
8, 1-19, 1-20, 1-24, 1-26, 1-27,
1-28, 1-29, 1-30, 1-31, 1-32, 1-3
3, 1-34, 1-35, 1-36, 1-37, 1-42,
1-43, 1-44, 1-45, 1-46, 1-48, 1-5
0, 1-51, 1-52, 1-54, 1-57, 1-69,
1-70, 1-73, 1-74, 1-87, 1-90, 1-9
4, 1-97, 1-100, 1-103, 1-104, 1-
105, 1-106, 1-107, 1-110, 1-11
3, 1-114, 2-5, 2-20, 2-413-3, 3-
7,4-3,4-13,4-22,5-1,5-3,5-1
1, 5-13, 5-14, 5-16, 5-28, 5-29,
5-30, 5-31, 5-32, 5-33, 5-65, 5-6
6, 5-67, 6-13, 6-23, 6-31. (3) Particularly preferred example compound numbers 1-1, 1-4, 1-5, 1-7, 1-8, 1-16, 1-2
0, 1-24, 1-26, 1-28, 1-30, 1-35,
1-37, 1-44, 1-45, 1-46, 1-50, 1-5
1, 1-52, 1-54, 1-57, 1-70, 1-73,
1-74, 1-87, 1-94, 1-99, 1-104, 1-
107, 2-20, 3-7, 4-3, 4-13, 4-19,
5-1, 5-13, 5-14, 5-66. (4) Optimally, 7- (4-benzyloxyphenyl) -2-mercaptoheptanoic acid (Exemplary Compound No. 1-20), 7- (5-chlorothien-2-yl) -2-mercaptoheptanoic acid, 2- Mercapto
-7- [4- (2-phenethyloxy) phenyl] heptanoic acid (Exemplary Compound No. 3-7), 6- (4-benzyloxyphenyl) -2-mercaptohexanoic acid (Exemplary Compound No. 1-4), 6 -(4-benzyloxyphenoxy) -2-mercaptohexanoic acid (exemplified compound No. 5-13), 2-mercapto-7- [4- (4-thiazolylmethoxy) phenyl] heptanoic acid (exemplified compound No. 1- 57) 2-Mercapto-7- [4- (2-thienylmethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1-50), 2-mercapto-7-
[4- (2-pyridylmethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1-44), 2-mercapto-7- [4-
(2-Pyridylethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1-70), 2-mercapto-7- [4- (3-thienylmethoxy) phenyl] heptanoic acid (Compound Reference No. 1-51), 2-mercapto -7- [4- (2-Thiazolylmethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1-
87) 2-mercapto-7- (4-phenacyloxyphenyl) heptanoic acid (Exemplary Compound No. 1-94), 6- (3
-Benzyloxyphenoxy) -2-mercaptohexanoic acid (Exemplary Compound No. 5-14), 2-mercapto-7- [4
-(5-Methyl-2-thienylmethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1-104), 7- [4- (4-
Fluorobenzyloxy) phenyl] -2-mercaptoheptanoic acid (Exemplary Compound No. 1-37), 2-mercapto-7- [2-fluoro-4- (phenylmethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1-73) , 2-
Mercapto-7- [2-fluoro-4- (2-thienylmethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1-
74).

[0120]

BEST MODE FOR CARRYING OUT THE INVENTION The compound represented by the general formula (I) of the present invention can be produced, for example, by the following production method.

Method A

[0122]

Embedded image In the above formula, A, W, X, and Y have the same meaning as described above.

Step A1 This step comprises the steps of preparing the corresponding thiazolidine-2,4-dione compound
By hydrolyzing (II) in the presence of a base under aqueous conditions, 2-mercaptocarboxylic acid (II) wherein R is a hydrogen atom among the 2-mercaptocarboxylic acid derivatives represented by formula (I)
This is a method for producing I).

The base used is, for example, a hydroxide of an alkali metal such as lithium, potassium or sodium; an alkali metal bicarbonate such as potassium hydrogen carbonate or sodium hydrogen carbonate; an alkali metal carbonate such as potassium carbonate or sodium carbonate. Salt; ammonia and the like.

The solvent used is not particularly limited as long as it does not affect the reaction. Examples thereof include water; alcohols such as methanol, ethanol and propanol; ethers such as diethyl ether, tetrahydrofuran and dioxane; dimethylformamide; Amides such as dimethylacetamide, hexamethylphosphoric triamide;
Sulfoxides such as dimethyl sulfoxide; or a mixed solvent of water and these organic solvents is preferably used.

The reaction is preferably carried out under ice cooling or under reflux with heating.

The reaction time varies depending on the reaction reagent, reaction temperature, reaction amount and the like, but is usually 0.5 to 10 hours.

The reaction is preferably carried out in a solvent of water and an alcohol for 1 hour to 6 hours under ice cooling or heating to reflux.

Method B

[0130]

Embedded image In the above formula, A, W, X, and Y have the same meaning as described above. R ′ represents the ester residue described above, and R ″
Is a case where R represents an alkanoyl group having 1 to 6 carbon atoms or an arylaminocarbonyl group having an aryl having 6 to 10 carbon atoms which may have 1 to 3 substituents β. These groups, or EtOC (=
And a protecting group for an SH group such as (S) or (H ₂ N) ₂ C. L represents a leaving group.

The "leaving group" for L is not particularly limited as long as it is a group capable of leaving in a nucleophilic substitution reaction. Examples of the group include a chlorine atom, a bromine atom and an iodine atom. Halogen atom; having 1 to 4 carbon atoms such as methanesulfonyloxy or ethanesulfonyloxy
Or an aryl moiety such as benzenesulfonyloxy or toluenesulfonyloxy having 6 to 10 carbon atoms which may have 1 to 3 alkyl having 1 to 3 carbon atoms. Arylsulfonyloxy group. It is preferably a halogen atom, more preferably a bromine atom or an iodine atom.

In the method B, a carboxylic acid ester (IV) having a substituent such as halogen at a corresponding site is reacted with a protected sulfur nucleophile (R ″ S ⁻ ) such as potassium thioacetate,
Obtained protected 2-mercapto-substituted ester derivative
In this method, (V) is hydrolyzed under aqueous conditions in the presence of a base to obtain a 2-mercaptocarboxylic acid derivative (VI) or (III).

[0133] Step B1 In this step, the compound (IV), R ''S ^- a step of reacting with the sulfur nucleophile represented by.

Compound (IV) has the general formula AWXY-CH ₂ -COOR '
, For example, N-bromosuccinic acid and reacting it according to a conventional method to introduce an L group.

The reaction solvent of the compound (IV) with the nucleophile is not particularly limited, but is preferably a polar solvent such as dimethylformamide.

The reaction temperature ranges from under ice-cooling to room temperature.

The reaction time is not particularly limited.
0.5 to several hours.

Step B2 In this step, the 2-mercaptocarboxylic acid derivative (VI) or (III) is hydrolyzed under aqueous conditions in the presence of a base to give the corresponding 2-mercaptocarboxylic acid derivative (V).
It is a method of manufacturing.

The reaction is carried out in the same manner as in the above-mentioned step A1.

Method C

[0141]

Embedded image In the above formula, A, W, X, Y, L and R 'have the same meanings as described above.

In the method C, the corresponding 1,3-dithiane-2-carboxylic acid ester represented by the general formula (VII) and the general formula AWX
The compound represented by the formula (VIII) is synthesized by reacting the compound represented by -YL, the protecting group of the obtained compound (VIII) is removed, and the obtained ketone derivative (having a ketone at the α-position) ) To synthesize a compound represented by the general formula (IX),
This is a method of producing a compound (III) by introducing a protected thiol group at the α-position of the obtained compound (IX), followed by hydrolysis. Step C1 In this step, the corresponding 1,3-dithiane-2-carboxylic acid ester represented by the general formula (VII) is converted to an alcoholate such as an alkali metal such as lithium, potassium or sodium; or lithium hydride, potassium hydride or hydrogen. This is a step of reacting an active derivative obtained by treating with an alkali metal hydride such as sodium fluoride with a compound represented by the general formula AWXYL to synthesize a compound represented by the general formula (VIII).

The solvent used for preparing the active derivative is as follows:
For example, solvents such as dimethylformamide, hexamethylphosphoric triamide, tetrahydrofuran, ethyl ether, dioxane, toluene, methanol, ethanol and the like.

The reaction temperature is from under ice-cooling to room temperature.

The reaction time varies depending on the compound to be used, the type of reagent, the reaction temperature, the reaction amount and the like, but is usually 0.5 to several hours.

The active derivative obtained by the above-mentioned production method and the general formula
The reaction with the compound represented by AWXYL is usually performed by adding the compound represented by the general formula AWXYL to a reaction mixture containing the active form.

As the reaction solvent used here, the solvent used for preparing the above active derivative can be used.

The reaction temperature is from under ice-cooling to room temperature.

The reaction time varies depending on the compound to be used, the type of reagent, the reaction temperature, the reaction amount and the like, but is usually 0.5 to several hours.

The leaving group represented by L is the same as the above-mentioned leaving group L, but is preferably an iodine atom. Step C2 In step C2, the protecting group of compound (VIII) obtained in step C1 is removed, and the obtained ketone derivative (having a ketone at the α-position) is reduced to obtain a compound represented by general formula (IX). It is a process.

The removal of the protecting group of compound (VIII) can be carried out in a solvent by
The reaction is performed by reacting with N-bromosuccinimide.

As the reaction solvent, a mixed solvent of water and a polar solvent such as acetonitrile and tetrahydrofuran is used.

The reaction temperature ranges from under ice-cooling to room temperature.

The reaction time is not particularly limited.
0.5 to several hours.

The ketone derivative obtained by the above reaction is usually subjected to a reduction treatment without isolation, to obtain a compound represented by the general formula (IX).

The reduction is carried out in a conventional manner using a reducing agent such as a metal hydride such as potassium borohydride or sodium borohydride in a solvent such as methanol or ethanol.

The reaction temperature is from under ice-cooling to room temperature.

The reaction time is not particularly limited.
0.5 to several hours. Step C3 This step is a step of introducing a protected thiol group at the α-position of compound (IX) obtained in the above-mentioned step C2, followed by hydrolysis.

The thiol group is introduced by first removing the hydroxyl group at the α-position of compound (IX) to compound (IX) using an activating agent, for example, a sulfonic acid halide such as mesyl chloride or tosyl chloride. It is carried out by introducing a group and then reacting with potassium thioacetate, sodium thioacetate and the like.

The reaction solvent is not particularly limited, but is preferably methylene chloride, toluene, dimethylformamide or the like.

The reaction temperature is from under ice-cooling to room temperature.

The reaction time is not particularly limited.
0.5 to several hours.

In the hydrolysis, the reaction product obtained by the above-mentioned production method is subjected to a conventional method, for example, in the presence of a base in water, methanol, tetrahydrofuran or the like or a mixed solvent thereof in the presence of a base, for example, hydroxide of alkali metal. , Bicarbonate and carbonate.

The reaction temperature is from under ice cooling to room temperature.

The reaction time is not particularly limited.
0.5 to several hours.

Further, by bringing a 2-mercaptocarboxylic acid derivative represented by the general formula (I) into contact with a hydroxide of the metal in an aqueous solvent, a salt thereof can be obtained. The 2-mercaptocarboxylic acid derivative represented by the general formula (I) of the present invention can be produced from a compound represented by the following general formula (II).

[0167]

Embedded image (Wherein, A, W, X, and Y have the same meanings as described above.) This compound group is useful as a starting material for the compound group represented by the general formula (I) of the present invention, and these compounds themselves Has a hypoglycemic effect, a hypolipidemic effect, etc., and is a prophylactic and / or therapeutic agent for diabetes, hyperlipidemia, etc.

As the compound represented by the general formula (II) used in the synthesis of the compound represented by the general formula (I) of the present invention, the following compounds can be exemplified.

[0169]

[Table 9] X represents a single bond. ────────────────────────── Exemplified compound Substituent A on ring A W-XY No.────────────────────────── 9-1 4-Cl Ph (CH ₂ ) ₃ 9-2 4-PhCH ₂ O Ph (CH ₂ ) ₃ 9-3 4-Cl Ph (CH ₂ ) ₄ 9-4 4-PhCH ₂ O Ph (CH ₂ ) ₄ 9-5 H Ph (CH ₂ ) ₅ 9-6 2-Cl Ph (CH ₂ ) ₅ 9-7 3-Cl Ph (CH ₂ ) ₅ 9-8 4-Cl Ph (CH ₂ ) ₅ 9-9 4-Br Ph (CH ₂ ) ₅ 9-10 4-I Ph (CH ₂ ) ₅ 9 -11 4-F Ph (CH ₂ ) ₅ 9 -12 4-CH ₃ Ph (CH ₂ ) ₅ 9 -13 4-CF ₃ Ph (CH ₂ ) ₅ 9 -14 4-OH Ph (CH ₂ ) ₅ 9 -15 4-MeO Ph (CH ₂ ) ₅ 9-16 4-Me (CH ₂ ) ₄ CH ₂ O Ph (CH ₂ ) ₅ 9-17 4-cHexCH ₂ O Ph (CH ₂ ) ₅ 9-18 4- Ph Ph (CH ₂ ) ₅ 9-19 4-PhO Ph (CH ₂ ) ₅ 9-20 4-PhCH ₂ O Ph (CH ₂ ) ₅ 9-21 4- (2-MeOBnO) Ph (CH ₂ ) ₅ 9 -22 4- (3-MeOBnO) Ph (CH ₂ ) ₅ 9-23 4- (4-MeOBnO) Ph (CH ₂ ) ₅ 9-24 3-PhCH ₂ O Ph (CH ₂ ) ₅ 9-25 2- _{PhCH 2 O Ph (CH 2)} 5 9-26 4- (4-ClPhCH 2 O) Ph (CH 2) 5 9-27 4- (4-MePhCHMeO) Ph (CH 2) 5 9-28 4-PhCH 2 CH ₂ O Ph (CH ₂ ) ₅ 9-29 4-PhCH ₂ CH ₂ CH ₂ O Ph (CH ₂ ) ₅ 9-30 4-PhOCH ₂ Ph (CH ₂ ) ₅ 9-31 4-PhOCHMe Ph (CH ₂ ) ₅ 9-32 4 -PhCH ₂ OCH ₂ Ph (CH ₂ ) ₅ 9-33 4-PhCH ₂ CH ₂ Ph (CH ₂ ) ₅ 9-34 4-PhCH ₂ CHOH Ph (CH ₂ ) ₅ 9-35 4-PhCH ₂ C = O Ph (CH ₂ ) ₅ 9-36 4-PhCH (Me) O Ph (CH ₂ ) ₅ 9-37 4- (4-FPhCH ₂ O) Ph (CH ₂ ) ₅ 9-38 3,4-F ₂ Ph (CH ₂ ) ₅ 9-39 3,4- (CH ₃ O) ₂ Ph (CH ₂ ) ₅ 9-40 4-PhCH ₂ O, 3-F Ph (CH ₂ ) ₅ 9-41 4-PhCH ₂ O _{, 3-CH 3 O Ph (} CH 2) 5 9-42 4-Cl Ph (CH 2) 6 9-43 4-Cl Ph (CH 2) 7 9-44 4- (2-PyrCH 2 O) Ph ( _{CH 2) 5 9-45 4- (3} -PyrCH 2 O) Ph (CH 2) 5 9-46 4- (4-PyrCH 2 O) Ph (CH 2) 5 9-47 4- (2-PymCH 2 O) Ph (CH ₂ ) ₅ 9-48 4- (4-PymCH ₂ O) Ph (CH ₂ ) ₅ 9-49 4- (2-PyzCH ₂ O) Ph (CH ₂ ) ₅ 9-50 4- ( 2-ThiCH ₂ O) Ph (CH ₂ ) ₅ 9-51 4- (3-ThiCH ₂ O) Ph (CH ₂ ) ₅ 9-52 4- (2-ThiCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ 9-53 4- (3-ThiCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ 9-54 4- (2-FurCH ₂ O) Ph (CH ₂ ) ₅ 9-55 4- (2-FurCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ 9-56 4- (3-FurCH ₂ O) Ph (CH ₂ ) ₅ 9-57 4- (4-ThizCH ₂ O) Ph (CH ₂ ) ₅ 9-58 4- ( 5-ThizCH ₂ O) Ph (CH ₂ ) ₅ 9-59 4- (2-ThizCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ 9-60 4- (4-ThizCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ 9-61 4- (5-ThizCH ₂ CH ₂ O ) Ph (CH ₂ ) ₅ 9-62 4- (2-OxaCH ₂ O) Ph (CH ₂ ) ₅ 9-63 4- (4-OxaCH ₂ O) Ph (CH ₂ ) ₅ 9-64 4- (5 _{-OxaCH 2 O) Ph (CH 2} ) 5 9-65 4- (5-Me-2-Me-4-OxaCH 2 O) Ph (CH 2) 5 9-66 4- (5-Me-2-Me -4-OxaCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ 9-67 4- (5-Me-2-Me-4-ThizCH ₂ O) Ph (CH ₂ ) ₅ 9-68 4- (5-Me -2-Me-4-ThizCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ 9-69 4- (3-Me-5-Me-4-IsoxCH ₂ O) Ph (CH ₂ ) ₅ 9-70 4- (2-PyrCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ 9-71 4- (3-PyrCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ 9-72 4- (4-PyrCH ₂ CH ₂ O) Ph (CH ₂ ) ₅ 9-73 2-F, 4- (PhCH ₂ O) Ph (CH ₂ ) ₅ 9-74 2-F, 4- (2-ThiCH ₂ O) Ph (CH ₂ ) ₅ 9-75 3-Cl, 4- (2-ThizCH ₂ O) Ph (CH ₂ ) ₅ 9-76 3-Me, 4- (PhCH ₂ O) Ph (CH ₂ ) ₅ 9-77 3-Me, 4- (2 -ThiCH ₂ O) Ph (CH ₂ ) ₅ 9-78 3-Me, 4- (2-ThizCH ₂ O) Ph (CH ₂ ) ₅ 9-79 3-MeO, 4- (2-ThiCH ₂ O) Ph _{(CH 2) 5 9-80 3-} MeO, 4- (2-ThizCH 2 O) Ph (CH 2) 5 9-81 4- (CH 2 = CH-CH 2) Ph (CH 2) 5 9-82 4- (Me-CH = CH) Ph (CH 2) 5 9-83 4- [Me-C (Me) = CH-CH 2] Ph (CH 2) 5 9-84 4- [CH 2 = C H-CH (Me)] Ph (CH 2) 5 9-85 4- (1-NpCH 2) Ph (CH 2) 5 9-86 4- (2-NpCH 2) Ph (CH 2) 5 9-87 3-MeO, 4- (2- ThizCH 2 O) Ph (CH 2) 5 9-88 BzCH 2 O Ph (CH 2) 5 9-89 Ph (OH) CHCH 2 O Ph (CH 2) 5 9-90 4 - [(2-Thi) C = OCH 2 O] Ph (CH 2) 5 9-91 4- [2- (5-Me-Thi) CH 2 O] Ph (CH 2) 5 9-92 4- [4- (5-Me-2 -Ph-Isox) CH 2 O] Ph (CH 2) 5 9-93 4- [4- (2-Ph) -ThizCH 2 O] Ph (CH 2) 5 9- 94 4- [2- (3-Me ) -ThiCH 2 O] Ph (CH 2) 5 9-95 4- (HO 2 CCH 2 O) Ph (CH 2) 5 9-96 4-Bz Ph (CH 2 ) ₅ 9-97 4- (2-MeO-PhO) Ph (CH ₂ ) ₅ 9-98 4-[(2-Thi) (OH) CHCH ₂ O] Ph (CH ₂ ) ₅ 9-99 4- ( 2-ThizCH ₂ O) Ph (CH ₂ ) ₅ 9-100 4- [2- (5-Me-2-Ph-4-Oxa) CH ₂ CH ₂ O] Ph (CH ₂ ) ₅ 9-101 4- (2-FPhCH ₂ O) Ph (CH ₂ ) ₅ 9-102 4- (3-FPhCH ₂ O) Ph (CH ₂ ) ₅ ─────────────────── ───────

[0170]

[Table 10] X represents a single bond. {Exemplified compound A Substituent on ring A A W-X-Y number} ─────────────────────── 10-1 6-Cl 2-Np (CH ₂ ) ₃ 10-2 6-PhCH ₂ O 2-Np (CH ₂ ) ₃ 10-3 6-Cl 2-Np (CH ₂ ) ₄ 10-4 6-PhCH ₂ O 2-Np (CH ₂ ) ₄ 10-5 H 2-Np (CH ₂ ) ₅ 10-6 4- Cl 2-Np (CH ₂ ) ₅ 10-7 6-Cl 2-Np (CH ₂ ) ₅ 10-8 7-Cl 2-Np (CH ₂ ) ₅ 10-9 6-Br 2-Np (CH ₂ ) ₅ 10-10 6-I 2-Np (CH ₂ ) ₅ 10-11 6-F 2-Np (CH ₂ ) ₅ 10-12 6-CH ₃ 2-Np (CH ₂ ) ₅ 10-13 6-CF ₃ 2-Np (CH ₂ ) ₅ 10-14 6-OH 2-Np (CH ₂ ) ₅ 10-15 6-MeO 2-Np (CH ₂ ) ₅ 10-16 6-Me (CH ₂ ) ₅ CH ₂ O 2-Np (CH ₂ ) ₅ 10-17 6-cHexMeO 2-Np (CH ₂ ) ₅ 10-18 6-Ph 2-Np (CH ₂ ) ₅ 10-19 6-PhO 2-Np (CH ₂ ) ₅ 10-20 6-PhCH ₂ O 2-Np (CH ₂ ) ₅ 10-21 4-PhCH ₂ O 2-Np (CH ₂ ) ₅ 10-22 7-PhCH ₂ O 2-Np (CH ₂ ) ₅ 10 -23 8-PhCH ₂ O 2-Np (CH ₂ ) ₅ 10-24 6- (4-ClPhCH ₂ O) 2-Np (CH ₂ ) ₅ 10-25 6- (4-MePhCHMeO) 2-Np (CH ₂ ) ₅ 10-26 6-PhCH ₂ CH ₂ O 2-Np (C H ₂ ) ₅ 10-27 6-PhCH ₂ CH ₂ CH ₂ O 2-Np (CH ₂ ) ₅ 10-28 6-PhOCH ₂ 2-Np (CH ₂ ) ₅ 10-29 6-PhOCHMe 2-Np (CH ₂ ) ₅ 10-30 6-PhCH (Me) O 2-Np (CH ₂ ) ₅ 10-31 6,7-Cl ₂ 2-Np (CH ₂ ) ₅ 10-32 6,7-F ₂ 2-Np (CH ₂ ) ₅ 10-33 6,7- (CH ₃ O) ₂ 2-Np (CH ₂ ) ₅ 10-34 6-PhCH ₂ O-7-F 2-Np (CH ₂ ) ₅ 10-35 6 -PhCH ₂ O-7-CH ₃ O 2-Np (CH ₂ ) ₅ 10-36 6-Cl 2-Np (CH ₂ ) ₆ 10-37 6-Cl 2-Np (CH ₂ ) ₇ 10-38 6 -(2-PyrCH ₂ O) 2-Np (CH ₂ ) ₅ 10-39 6- (3-PyrCH ₂ O) 2-Np (CH ₂ ) ₅ 10-40 6- (4-PyrCH ₂ O) 2- Np (CH ₂ ) ₅ 10-41 6- (2-ThiCH ₂ O) 2-Np (CH ₂ ) ₅ 10-42 6- (3-ThiCH ₂ O) 2-Np (CH ₂ ) ₅ 10-43 6 -(2-FurCH ₂ O) 2-Np (CH ₂ ) ₅ 10-44 6- (3-FurCH ₂ O) 2-Np (CH ₂ ) ₅ 10-45 6- (2-ThizCH ₂ O) 2- Np (CH ₂ ) ₅ 10-46 6- (4-ThizCH ₂ O) 2-Np (CH ₂ ) ₅ 10-47 6- (5-ThizCH ₂ O) 2-Np (CH ₂ ) ₅ 10-48 6 -(2-ThizCH ₂ CH ₂ O) 2-Np (CH ₂ ) ₅ 10-49 6- (4-ThizCH ₂ CH ₂ O) 2-Np (CH ₂ ) ₅ 10-50 6- (5-ThizCH ₂ (CH ₂ O) 2-Np (CH ₂ ) ₅ 10-51 6- (2-OxaCH ₂ O) 2-Np (CH ₂ ) ₅ 10-52 6- (4-OxaCH ₂ O) 2-Np (CH ₂ ) ₅ 10-53 6- (5-OxaCH ₂ O) 2-Np (CH ₂ ) ₅ 10-54 6- (2-PyrCH ₂ (CH ₂ O) 2-Np (CH ₂ ) ₅ 10-55 6- (3-PyrCH ₂ CH ₂ O) 2-Np (CH ₂ ) ₅ 10-56 6- (4-PyrCH ₂ CH ₂ O) 2- Np (CH ₂ ) ₅ 10-57 6- (CH ₂ = CH-CH ₂ ) 2-Np (CH ₂ ) ₅ 10-58 6- (Me-CH = CH) 2-Np (CH ₂ ) ₅ 10- 59 6- [Me-C (Me) = CH-CH ₂ ] 2-Np (CH ₂ ) ₅ 10-60 6- [CH ₂ = CH-CH (Me)] 2-Np (CH ₂ ) ₅ ── ──────────────────────

[0171]

[Table 11] X represents a single bond. {Exemplified Compound A Substituent on Ring A A W-X-Y Number} ───────────────────── 11-1 5-Cl 2-Pyr (CH ₂ ) ₅ 11-2 H 2-Pyr (CH ₂ ) ₅ 11-3 H 3-Pyr (CH ₂ ) ₅ 11-4 4-PhCH ₂ O 2-Pyr (CH ₂ ) ₅ 11-5 5-PhCH ₂ O 2-Pyr (CH ₂ ) ₅ 11-6 4-Cl 2-Thi (CH ₂ ) ₅ 11-7 5-Cl 2-Thi (CH ₂ ) ₅ 11-8 4-PhCH ₂ O 2-Thi (CH ₂ ) ₅ 11-9 5-PhCH ₂ O 2-Thi (CH ₂ ) ₅ 11-10 H 2-Fur (CH ₂ ) ₅ 11-11 H 3-Fur (CH ₂ ) ₅ 11-12 2-Bz 5-Bfur (CH ₂ ) ₅ ─────────── ────────────

[0172]

X represents a single bond. 例 示 Exemplified compound Substituent on ring A A W-X -Y number ──────────────────────────── 12-1 H 2-Bthi (CH ₂ ) ₅ 12-2 H 3-Bthi (CH ₂ ) ₅ 12-3 H 2-Quin (CH ₂ ) ₅ 12-4 7-Cl 3-Quin (CH ₂ ) ₅ 12-5 H 2-Bfur (CH ₂ ) ₅ 12-6 6-Me 3 -Bfur (CH ₂ ) ₅ 12-7 5-PhCH ₂ O 2-Bthi (CH ₂ ) ₅ 12-8 6-PhCH ₂ O 3-Bthi (CH ₂ ) ₅ 12-9 6-PhCH ₂ O 2-Quin (CH ₂ ) ₅ 12-10 7-PhCH ₂ O 3-Quin (CH ₂ ) ₅ 12-11 5-PhCH ₂ O 2-Bfur (CH ₂ ) ₅ 12-12 6-PhCH ₂ O 3-Bfur (CH ₂ ) ₅ 12-13 H 2,3-dHBfur-5-yl (CH ₂ ) ₅ ────────────────────────────

[0173]

[Table 13] {Exemplary Compounds Substituents on Ring A of AW XY Number} ───────────────────────── 13-1 4-Cl Ph-O (CH ₂ ) ₄ 13-2 4-Br Ph-O (CH ₂ ) ₄ 13-3 4-I Ph-O (CH ₂ ) ₄ 13-4 4-F Ph-O (CH ₂ ) ₄ 13-5 4-CH ₃ Ph-O (CH ₂ ) ₄ 13-6 4 -CF ₃ Ph-O (CH ₂ ) ₄ 13-7 4-OH Ph-O (CH ₂ ) ₄ 13-8 4-MeO Ph-O (CH ₂ ) ₄ 13-9 4-Me (CH ₂ ) _{5 CH 2 O PhO (CH 2)} 4 13-10 4-cHexCH 2 O PhO (CH 2) 4 13-11 4-Ph PhO (CH 2) 4 13-12 4-PhO PhO (CH ₂ ) ₄ 13-13 4-PhCH ₂ O Ph-O (CH ₂ ) ₄ 13-14 3-PhCH ₂ O Ph-O (CH ₂ ) ₄ 13-15 2-PhCH ₂ O Ph-O (CH ₂ ) ₄ 13-16 4- (4-ClPhCH ₂ O) Ph-O (CH ₂ ) ₄ 13-17 4- (4-MePhCHMeO) Ph-O (CH ₂ ) ₄ 13-18 4-PhCH ₂ CH ₂ O Ph-O (CH ₂ ) ₄ 13-19 4-PhCH ₂ CH ₂ CH ₂ O Ph-O (CH ₂ ) ₄ 13-20 4-PhOCH ₂ Ph-O (CH ₂ ) ₄ 13-21 4-PhOCHMe Ph-O (CH ₂ ) ₄ 13-22 4-PhCH (Me) O Ph-O (CH ₂ ) ₄ 13-23 3,4-Cl ₂ Ph-O (CH ₂ ) ₄ 13-24 3,4-F ₂ Ph-O (CH ₂ ) ₄ 13-25 3,4- (CH ₃ O) ₂ Ph-O (CH ₂ ) ₄ 13-26 4-PhCH ₂ O, 3-F Ph-O (CH ₂ ) ₄ 13-27 4-PhCH ₂ O, 3-CH ₃ O Ph-O (CH ₂ ) ₄ 13-28 4-Cl Ph-O (CH ₂ ) ₆ 13-29 4-F Ph - O (CH 2) 6 13-30 4-I Ph - O (CH 2) 6 13-31 4-Ph Ph - O (CH 2) 6 13-32 4-Cl Ph CH 2 O ( CH ₂ ) ₄ 13-33 H Ph CH ₂ O (CH ₂ ) ₅ 13-34 4- (2-PyrCH ₂ O) Ph-O (CH ₂ ) ₄ 13-35 4- (3-PyrCH ₂ O) Ph -O (CH ₂ ) ₄ 13-36 4- (4-PyrCH ₂ O) Ph-O (CH ₂ ) ₄ 13-37 4- (2-ThiCH ₂ O) Ph-O (CH ₂ ) ₄ 13-38 4- (3-ThiCH ₂ O) Ph-O (CH ₂ ) ₄ 13-39 4- (2-FurCH ₂ O) Ph-O (CH ₂ ) ₄ 13-40 4- (3-FurCH ₂ O) Ph -O (CH ₂ ) ₄ 13-41 4- (2-ThizCH ₂ O) Ph-O (CH ₂ ) ₄ 13-42 4- (4-ThizCH ₂ eO) Ph-O (CH ₂ ) ₄ 13-43 4- (5-ThizCH ₂ O) Ph-O (CH ₂ ) ₄ 13-44 4- (2-OxaCH ₂ O) Ph-O (CH ₂ ) ₄ 13-45 4- (4-OxaCH ₂ O) Ph -O (CH ₂ ) ₄ 13-46 4- (5-OxaCH ₂ O) Ph-O (CH ₂ ) ₄ 13-47 4- (2-PyrCH ₂ CH ₂ O) Ph-O (CH ₂ ) ₄ 13 -48 4- (3-PyrCH ₂ CH ₂ O) Ph-O (CH ₂ ) ₄ 13-49 4- (4-PyrCH ₂ CH ₂ O) Ph-O (CH ₂ ) ₄ 13-50 4- (CH ₂ = CH-CH ₂ ) Ph-O (CH ₂ ) ₄ 13-51 4- (Me-CH = CH) Ph-O (CH ₂ ) ₄ 13-52 4- [Me-C (Me) = CH-CH ₂ ] Ph-O (CH ₂ ) ₄ 13-53 4- [CH ₂ = CH-CH (Me)] Ph-O (CH ₂ ) ₄ 13-54 4-PhCH ₂ O, 2-Me Ph-O (CH ₂ ) ₄ 13-55 4- PhCH ₂ O, 3-Me Ph-O (CH ₂ ) ₄ 13-56 3- (2-ThiCH ₂ O) Ph-O (CH ₂ ) ₄ ─────────────── ──────────────

[0174]

[Table 14] {Exemplary Compounds Substituents on Ring A of AW XY Number} ─────────────────────── 14-1 6-Cl 2-Np-O (CH ₂ ) ₄ 14-2 4-Br 2-Np-O (CH ₂ ) ₄ 14-3 7-I 2-Np-O (CH ₂ ) ₄ 14-4 6-F 2-Np-O (CH ₂ ) ₄ 14-5 6-CH ₃ 2-Np-O ( (CH ₂ ) ₄ 14-6 6-CF ₃ 2-Np-O (CH ₂ ) ₄ 14-7 6-OH 2-Np-O (CH ₂ ) ₄ 14-8 6-MeO 2-Np-O (CH ₂ ) ₄ 14-9 6-Me (CH ₂ ) ₅ CH ₂ O 2-Np-O (CH ₂ ) ₄ 14-10 6-cHexCH ₂ O 2-Np-O (CH ₂ ) ₄ 14-11 6- Ph 2-Np-O (CH ₂ ) ₄ 14-12 6-PhO 2-Np-O (CH ₂ ) ₄ 14-13 6-PhCH ₂ O 2-Np-O (CH ₂ ) ₄ 14-14 7- PhCH ₂ O 2-Np-O (CH ₂ ) ₄ 14-15 4-PhCH ₂ O 2-Np-O (CH ₂ ) ₄ 14-16 6- (4-ClPhCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-17 6- (4-MePhCHMeO) 2-Np-O (CH ₂ ) ₄ 14-18 6-PhCH ₂ CH ₂ O 2-Np-O (CH ₂ ) ₄ 14-19 6-PhCH ₂ CH ₂ CH ₂ O 2-Np-O (CH ₂ ) ₄ 14-20 6-PhOCH ₂ 2-Np-O (CH ₂ ) ₄ 14-21 6-PhOCHMe 2-Np-O (CH ₂ ) ₄ 14- 22 6-PhCH (Me) O 2-Np- O (CH ₂ ) ₄ 14-23 H 2-Np-O (CH ₂ ) ₄ 14-24 6,7-Cl ₂ 2-Np-O (CH ₂ ) ₄ 14-25 6,7-F ₂ 2- Np-O (CH ₂ ) ₄ 14-26 6,7- (CH ₃ O) ₂ 2-Np-O (CH ₂ ) ₄ 14-27 6-PhCH ₂ O, 3-F 2-Np-O (CH ₂ ) ₄ 14-28 6-PhCH ₂ O, 7-CH ₃ O 2-Np-O (CH ₂ ) ₄ 14-29 6-Cl 2-Np-O (CH ₂ ) ₆ 14-30 6-F 2 -Np-O (CH ₂ ) ₆ 14-31 H 1-Np-O (CH ₂ ) ₆ 14-32 6-Ph 2-Np-O (CH ₂ ) ₆ 14-33 6-Cl 2-Np CH ₂ O (CH ₂ ) ₄ 14-34 H 2-Np CH ₂ O (CH ₂ ) ₅ 14-35 6- (2-PyrCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-36 6- (3 -PyrCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-37 6- (4-PyrCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-38 6- (2-ThiCH ₂ O) 2 -Np-O (CH ₂ ) ₄ 14-39 6- (3-ThiCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-40 6- (2-FurCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-41 6- (3-FurCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-42 6- (2-ThizCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-43 6- (4-ThizCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-44 6- (5-ThizCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-45 6- (2-OxaCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-46 6- (4-OxaCH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-47 6- (5-OxaCH ₂ O) 2-Np -O (CH ₂ ) ₄ 14-48 6- (2-PyrCH ₂ CH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-49 6- (3-PyrCH ₂ CH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-50 6- (4-PyrCH ₂ CH ₂ O) 2-Np-O (CH ₂ ) ₄ 14-51 6- (CH ₂ = CH-CH ₂ ) 2-Np -O (CH ₂ ) ₄ 14-52 6- (Me-CH = CH) 2-Np -O (CH ₂ ) ₄ 14-53 6- [Me-C (Me ) = CH-CH ₂ ] 2-Np-O (CH ₂ ) ₄ 14-54 6- [CH ₂ = CH-CH (Me)] 2-Np-O (CH ₂ ) ₄ ─────── ─────────────────────

[0175]

Table 15 Example Compounds on Ring A Substituents A W XY Numbers ─────────────── 15-1 H 1-Pyr-O (CH ₂ ) ₄ 15-2 H 2-Pyr-O (CH ₂ ) ₄ 15-3 H 3-Pyr -O (CH ₂ ) ₄ 15-4 4-Cl 1-Thi-O (CH ₂ ) ₄ 15-5 H 2-Thi-O (CH ₂ ) ₄ ───────────── ───────────

[0176]

[Table 16] Example Compound on ring A Substituent A W XY number ───────────────────────────── 16-1 H 2-Bthi-O (CH ₂ ) ₄ 16-2 H 3-Bthi -O (CH ₂ ) ₄ 16-3 H 2-Quin-O (CH ₂ ) ₄ 16-4 4-Cl 3-Quin-O (CH ₂ ) ₄ 16-5 H 2-Bfur-O (CH ₂ ) ₄ 16-6 4-Me 3-Bfur-O (CH ₂ ) ₄ 16-7 H 2,3-dHBfur-5-yl-O (CH ₂ ) ₄ ─────────────に お い て In the above table, (1) preferably exemplified compound numbers 9-1, 9-2, 9-3, 9-4, 9-5, 9 -6, 9-7,
9-8, 9-11, 9-13, 9-14, 9-15, 9-1
6, 9-17, 9-18, 9-19, 9-20, 9-21,
9-22, 9-24, 9-26, 9-27, 9-28, 9-2
9, 9-30, 9-31, 9-32, 9-33, 9-34,
9-35, 9-36, 9-37, 9-38, 9-40, 9-4
1, 9-42, 9-43, 9-44, 9-45, 9-46,
9-47, 9-48, 9-49, 9-50, 9-51, 9-5
2, 9-53, 9-54, 9-56, 9-57, 9-58,
9-59, 9-62, 9-63, 9-65, 9-67, 9-6
9, 9-70, 9-71, 9-73, 9-74, 9-76,
9-77, 9-78, 9-79, 9-80, 9-83, 9-8
7, 9-88, 9-89, 9-90, 9-91, 9-92,
9-93, 9-94, 9-95, 9-96, 9-97, 9-9
8, 9-99, 9-100, 10-4, 10-5, 10-
7, 10-11, 10-13, 10-20, 10-21, 1,
0-22, 10-23, 10-26, 10-28, 10-3
4,10-35,10-38,10-39,10-40,1
0-41, 10-42, 10-43, 10-44, 10-4
5, 10-46, 10-47, 10-51, 10-52, 1,
0-53, 10-63, 10-64, 10-66, 10-7
0, 10-72, 10-73, 10-76, 10-77, 1
0-78, 11-1, 11-3, 11-4, 11-5, 11-
6, 11-7, 11-8, 11-9, 11-12, 12-
1, 12-3, 12-4, 12-6, 12-8, 12-9,
12-12, 12-13, 13-1, 13-3, 13-6,
13-11, 13-12, 13-13, 13-14, 13-
15, 13-16, 13-18, 13-20, 13-26,
13-27, 13-28, 13-29, 13-30, 13-
31, 13-32, 13-33, 13-34, 13-35,
13-36, 13-37, 13-38, 13-39, 13-
40, 13-41, 13-42, 13-43, 13-44,
13-45, 13-46, 13-47, 13-54, 13-
55, 13-56, 14-1, 14-4, 14-5, 14-
6, 14-12, 14-13, 14-14, 14-18, 1
4-20, 14-23, 14-27, 14-28, 14-3
1, 14-33, 14-35, 14-36, 14-38, 1
4-39, 14-40, 14-42, 14-43, 14-4
4, 14-46, 15-1, 15-2, 15-3, 15-
4, 15-5, 16-1, 16-3, 16-5, 16-7. (2) More preferably, the exemplified compounds 9-1, 9-2, 9-3, 9-4, 9-5, 9-6, 9-7,
9-8, 9-14, 9-15, 9-16, 9-17, 9-1
8, 9-19, 9-20, 9-22, 9-24, 9-26,
9-27, 9-28, 9-29, 9-30, 9-31, 9-3
2, 9-33, 9-34, 9-35, 9-36, 9-37,
9-42, 9-43, 9-44, 9-45, 9-46, 9-4
8, 9-50, 9-51, 9-52, 9-54, 9-57,
9-69, 9-70, 9-73, 9-74, 9-88, 9-8
9, 9-90, 9-91, 9-93, 9-94, 9-95,
9-96, 9-97, 9-98, 9-99, 9-100, 1
0-5, 10-20, 10-41, 11-7, 11-12,
12-3, 12-13, 13-1, 13-3, 13-11,
13-13, 13-14, 13-16, 13-28, 13-
29, 13-30, 13-31, 13-32, 13-33,
13-54, 13-55, 13-56, 14-13, 14-
23, 14-31. (3) Particularly preferably, Exemplified Compound No. 9-4, 9-5, 9-7, 9-8, 9-16, 9-20, 9-
26, 9-28, 9-30, 9-35, 9-37, 9-4
4, 9-45, 9-46, 9-50, 9-51, 9-52,
9-54, 9-57, 9-70, 9-73, 9-74, 9-8
8, 9-91, 9-99, 10-20, 11-7, 12-
Compounds of 3, 12-13, 13-1, 13-13, 13-14. (4) Optimally, 5- [5- (4-benzyloxyphenyl) pentyl] thiazolidine-2,4-dione (Exemplary Compound No. 9-2
0) 5- [5- (5-chlorothien-2-yl) pentyl]
Thiazolidine-2,4-dione, 5- [5- [4- (2-phenethyloxy) phenyl] pentyl] thiazolidine-
2,4-dione (Exemplary Compound No. 11-7), 5- [4-
(4-benzyloxyphenyl) butyl] thiazolidine-
2,4-dione (Exemplary Compound No. 9-4), 5- [5- [4
-(4-thiazolylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione (Exemplary Compound No. 9-57),
5- [5- [4- (2-pyridylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione (Exemplary Compound No. 9
-44) 5- [5- [4- (2-pyridylethoxy) phenyl] pentyl] thiazolidine-2,4-dione (Exemplary Compound No. 9-70), 5- [5- [4- (2-thienyl) Ethoxy) phenyl] pentyl] thiazoline-2,4-dione (exemplified compound number 9-52), 5- [5- [4- (3-thienylmethoxy) phenyl] pentyl] thiazolidine-
2,4-dione (compound reference number 9-51), 5- [5-
[4- (2-thiazolylmethoxy) phenyl] pentyl]
Thiazolidine-2,4-dione (Exemplary Compound No. 9-9)
9) 5- [5- (4-phenacyloxyphenyl) pentyl] thiazolidine-2,4-dione (Exemplary Compound No. 9
-88), 5- [4- (3-benzyloxyphenoxy) butyl] thiazolidine-2,4-dione (Exemplary Compound No. 1
3-14) 5- [5- [4- (5-methyl-2-thienylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione (exemplified compound number 9-91), 5- [5- [4 − (4
-Fluorobenzyloxy) phenyl] pentyl] thiazolidine-2,4-dione (Exemplary Compound No. 9-3
7), 5- [5- [2-fluoro-4- (phenylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione (exemplified compound number 9-73), 5- [5- [2-fluoro-4 -(2-thienylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione (Exemplary Compound No. 9-74). The compound having the general formula (II) is
It can be synthesized by the following production method according to a conventional method. D method

[0177]

Embedded image In the above formula, A, W, and X have the same meanings as described above, and Y ′ represents a bond or a linear or branched alkylene group having 1 to 19 carbon atoms.

However, the -W-X-Y'- group does not show a bond.

Method D is a method in which the corresponding aldehyde derivative is condensed with a thiazolidine-2,4-dione derivative (X) to obtain a compound (XI) and then reduced to obtain a compound (XII). Step D1 Step D1 is a reaction between thiazolidine (X) and the above general formula AWX-Y'-C
This is a step of reacting with an aldehyde derivative represented by HO.

More specifically, thiazolidine (X) and a desired aldehyde derivative represented by the above general formula AWX-Y'-CHO are dissolved in an appropriate solvent, and heated under reflux using a Dean-Stark apparatus. The reaction is carried out while removing water.

The solvent is not particularly limited as long as it is inert, but is preferably benzene, toluene, or the like, which readily azeotropes with water.

When the reaction is carried out in the presence of piperidine acetate or the like, the reaction proceeds more easily.

The reaction time varies depending on the reaction amount and the like, but is usually 0.5 to 20 hours.

In Step D2, the compound (X) obtained in Step D1
This is a method of obtaining a thiazolidinedione compound (XII) by reducing the double bond of I) with a reducing agent in an appropriate solvent in the presence of a transition metal salt-organic coordination compound.

The solvent is not particularly limited as long as it is inert to the reaction. Examples thereof include water; alcohols such as methanol, ethanol and propanol; ethers such as diethyl ether, tetrahydrofuran and dioxane; dimethylformamide, dimethylacetamide and hexane. Amides such as methylphosphoric acid triamide; sulfoxides such as dimethyl sulfoxide; and a mixed solvent of water and these organic solvents are preferably used.

Examples of the transition metal salt include halides such as nickel, cobalt and copper. Preferably it is cobalt chloride.

The organic coordination compound may be any as long as it forms an organic coordination compound with a transition metal salt, and is preferably, for example, dimethylglyoxime, diethylglyoxime or diphenylglyoxime.

Examples of the metal borohydride include lithium borohydride, potassium borohydride, sodium borohydride and the like.

The reaction temperature for the above reduction is usually from under ice-cooling to room temperature.

The reaction time varies depending on the amount of compound (IV) used, the reaction temperature and the like and is not particularly limited, but is usually 0.5 to 20 hours. Method E

[0191]

Embedded image In the above formula, A, W, X, Y, and L have the same meanings as described above, and L preferably represents a halogen atom.

In the method E, thiazolidine-2,4-dione (X)
Of the 3 and 5 position protons of the
(XIII) is prepared, and a thiazolidine-2,4-dione derivative (II) is obtained by reacting a compound (XIII) with a corresponding active derivative represented by the general formula AWXYL, preferably a halide.

Step E1 In step E1, the synthesis of compound (XIII) from compound (X) is usually carried out by reacting with a base in a suitable solvent.

The base is LDA, n-butyllithium or the like, preferably LDA.

The solvent is not particularly limited as long as it is inert to the reaction, but is preferably an aprotic solvent, more preferably an ether such as ethyl ether, dioxane or tetrahydrofuran, or hexamethylphosphoramide. It is.

The reaction temperature is from ice cooling to room temperature.

Step E2 Compound (II) can be obtained by directly reacting the reaction product obtained in the above step E1 with an active derivative represented by the general formula AWXYL, preferably a halide. The reaction is carried out by adding the active derivative represented by the general formula AWXYL dropwise or all at once to a suspension of the reaction product obtained in the step E1 under ice-cooling.

After completion of the reaction, the target compound obtained in each of the above steps can be purified, if necessary, by a conventional method, for example, column chromatography, recrystallization, reprecipitation, or the like.

For example, the reaction solution is appropriately neutralized, then a solvent is added to the reaction solution for extraction, and the solvent is distilled off from the extract.
The obtained residue is purified by subjecting it to column chromatography using silica gel or the like, whereby a pure product of the target compound can be obtained.

Further, a certain amount of solvent is distilled off from the reaction solution,
By purifying by a recrystallization method, a salt of the target compound can be obtained.

In addition, in addition to those specifically described in the above-mentioned production methods, if necessary, a protective group may be introduced into a substituent or the like to proceed the reaction, and the protective group may be removed as needed. For example, when a carboxy group is present in the substitution α, the carboxy group is protected as an ester group to proceed the reaction, and the protective group is removed as appropriate. The 2-mercaptocarboxylic acid derivative of the present invention having the general formula (I) or a pharmaceutically acceptable ester thereof or a pharmaceutically acceptable salt thereof, and a thiazolidinedione compound having the general formula (II) are Is administered in various forms. The administration form is not particularly limited, and is determined according to various preparation forms, patient age, sex and other conditions, degree of disease, and the like. For example, tablets, pills, powders, granules, syrups, solutions, suspensions, emulsions, granules and capsules are orally administered. In the case of an injection, it is administered intravenously, alone or as a mixture with a normal replenisher such as glucose or amino acid, and, if necessary, intramuscularly, intradermally, subcutaneously or intraperitoneally. In the case of suppositories, they are administered rectally. Preferably it is oral administration. These various formulations
The excipient, binder, disintegrant, lubricant,
It can be formulated using known auxiliaries usually used in the field of known pharmaceutical preparations such as dissolving agents, flavoring and coating agents.

[0202] In the form of a tablet, carriers conventionally known in the art can be widely used, such as lactose, sucrose, sodium chloride, glucose, urea, starch, and the like.
Excipients such as calcium carbonate, kaolin, crystalline cellulose, and silicic acid; binding of water, ethanol, propanol, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethylcellulose, shellac, methylcellulose, potassium phosphate, polyvinylpyrrolidone, etc. Disintegrators such as dispersants, dried starch, sodium alginate, agar powder, laminaran powder, sodium bicarbonate, calcium carbonate, polyoxyethylene sorbitan fatty acid esters, sodium lauryl sulfate, stearic acid monoglyceride, starch, lactose; sucrose, stearin, cacao Disintegration inhibitors such as butter and hydrogenated oil; absorption promoters such as quaternary ammonium bases and sodium lauryl sulfate; humectants such as glycerin and starch; adsorbents such as starch, lactose, kaolin, bentonite and colloidal silicic acid ; Ltd. talc, stearates,
Lubricants such as boric acid powder and polyethylene glycol can be exemplified. Furthermore, tablets are tablets coated with normal skin as needed,
For example, sugar-coated tablets, gelatin-coated tablets, enteric-coated tablets, film-coated tablets or double tablets or multilayer tablets can be prepared.

In the case of molding into pills, carriers conventionally known in this field can be widely used as carriers, for example, excipients such as glucose, lactose, starch, cocoa butter, hydrogenated vegetable oil, kaolin, talc and the like; Examples thereof include a binder such as rubber powder, tragacanth powder, gelatin, and ethanol; and a disintegrant such as laminaran agar.

In the case of molding into the form of suppositories, those conventionally known in the art can be widely used as carriers, such as polyethylene glycol, cocoa butter, higher alcohols and the like.
Esters of higher alcohols, gelatin, semi-synthetic glycerides and the like can be mentioned.

When prepared as an injection, the liquid preparation and the suspension are preferably sterilized and isotonic with blood. When forming these liquid preparations, emulsions and suspensions, they may be diluted. All agents commonly used in this field can be used as the agent, for example, water, ethyl alcohol, propylene glycol, ethoxylated isostearyl alcohol, polyoxylated isostearyl alcohol,
Examples thereof include polyoxyethylene sorbitan fatty acid esters. In this case, a sufficient amount of salt, glucose, or glycerin to prepare an isotonic solution may be included in the pharmaceutical preparation, and ordinary solubilizing agents, buffers, soothing agents, and the like may be used. It may be added.

If necessary, coloring agents, preservatives, fragrances,
Flavoring agents, sweeteners and the like and other pharmaceuticals may be included.

The amount of the active ingredient compound contained in the above-mentioned pharmaceutical preparation is not particularly limited and may be appropriately selected in a wide range, but is usually from 1 to 70% by weight, preferably from 1 to 30% by weight in the whole composition. Is appropriate.

The dosage varies depending on symptoms, age, body weight, administration method, dosage form, etc., but is usually 0.001 mg (preferably 0.01 mg, more preferably 0.1 mg) per day for an adult per day. 2,000 mg (preferably 200 mg, more preferably 20 mg) can be administered once or several times as an upper limit.

[0209]

Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

[0210] In the examples, the term "column chromatography" means silica gel column chromatography unless otherwise specified. Example 1 7- (4-chlorophenyl) -2-mercap
Toheptanoic acid (Exemplified Compound No. 1-8) 1) 5- [5- (4-chlorophenyl) pentyl] thia
Zolidine-2,4 -dione (Exemplary Compound No. 9-8) A solution of 12 ml of diisopropylamine in 100 ml of tetrahydrofuran (THF) was cooled with ice-methanol, and 50 ml of 1.6 M n-butyllithium was added dropwise. After 10 minutes, thiazolidine-2,4-dione 4.5
g solution in 14 ml of HMPA was added dropwise. The reaction solution was returned to room temperature and stirred for 1 hour. Again, add the reaction solution to ice
After cooling with methanol, 5.5 g of 5- (4-chlorophenyl) pentyl iodide was added at once, and the reaction solution was returned to room temperature and stirred for 1 hour. Then, the reaction solution was acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was subjected to column chromatography and eluted with chloroform. The corresponding fraction was concentrated and dried to give 2.17 g of the title compound as a pale yellow candy (40% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.8-1.3 (6H, m), 2.3-1.8 (2H, m), 2.57 (2H, pst, J
= 7Hz), 4.25 (1H, dd, J = 5Hz, J = 8Hz), 7.10 (2H, psd, J = 9H
z), 7.23 (2H, psd, J = 9 Hz), 8.91 (1H, brs) 2) 7- (4-chlorophenyl) -2-mercaptohep
Obtained in Tan acid 1) 5- [5- (4-chlorophenyl) pentyl] thiazolidine-2,4-dione 2.1g was dissolved in ethanol 7.5ml, 10N-NaOH7.5ml
Was added and the mixture was heated and refluxed under a nitrogen atmosphere. 1.5 hours later,
The reaction was diluted with water and washed with ether. The aqueous layer was acidified with dilute hydrochloric acid, extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was subjected to column chromatography and eluted with chloroform. The corresponding fraction was concentrated to dryness to obtain 1.4 g of the title compound as a pale yellow candy (yield: 7).
1%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 2.1-1.2 (8H, m), 2.09 (1H, d, J = 9Hz), 2.57 (2H, ps
t, J = 7Hz), 3.30 (1H, dt, J = 7Hz, J = 9Hz), 7.10 (2H, psd, J = 9
Hz), 7.21 (2H, psd, J = 9 Hz), 8.80 (1H, brs) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
0,28.5,30.9,35.0,40.7,128.4,129.7,131.4,140.8,179.
1 Example 2 5- (4-chlorophenyl) -2-mercapto
Pentanoic acid (Exemplified Compound No. 1-1) 3- (4-chlorophenyl) iodide in the same manner as in Example 1.
From 3.9 g of propyl, 0.77 g of the title compound was obtained as a pale yellow candy (yield 23%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.5-2.1 (4H, m), 2.09 (1H, d, J = 9Hz), 2.61 (2H, m
m), 3.30 (1H, dt, J = 7Hz, J = 9Hz), 7.10 (2H, psd, J = 9Hz),
7.21 (2H, psd, J = 9 Hz), 8.39 (1H, brs) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 28.
7,34.5,34.6,40.7,128.6,129.8,131.8,139.9,178.6 Example 3 7- (4-benzyloxyphenyl) -2-
Mercaptoheptanoic acid (Exemplified Compound No. 1-20) 1) 5- [5- (4-benzyloxyphenyl) penty
Riden] thiazolidine- 2,4-dione 5- (4-benzyloxyphenyl) pentanal 1
8.0 g, 8.0 g of thiazolidine-2,4-dione and 0.5 g of piperidine acetate were added to 300 ml of toluene, and the mixture was heated and refluxed overnight using a Dean-Stark apparatus.
Then, the solvent was distilled off, and the residue was subjected to column chromatography and eluted with chloroform. The corresponding fraction was concentrated to dryness to give 12.5 g of the title compound as a yellow solid (yield 51%).

1H-NMR (89.55 MHz, δ ppm, CDC
_{l 3): 1.59 (4H,} m), 2.22 (2H, m), 2.57 (2H, pst, J = 7Hz),
6.89 (2H, psd, J = 9Hz), 7.01 (1H, t, J = 8Hz), 7.04 (2H, ps
d, J = 9Hz), 7.39 (5H, m) 2) 5- [5- (4-benzyloxyphenyl ) penty
Ru] thiazolidine-2,4 -dione (Exemplary Compound No. 9
-20) Cobalt chloride (CoCl ₂ ) hexahydrate in 50 ml of water
0.4 g, dimethylglyoxime 4.0 g and 1N-
15 drops of NaOH were added, and 5.5 g of sodium borohydride was further added at room temperature. To this solution, 12.5 g of 5- (5- (4-benzyloxyphenyl) pentylidene) thiazolidine-2,4-dione obtained in 1) was added to T solution.
A solution dissolved in 60 ml of HF and 30 ml of DMF was added dropwise under ice cooling. After completion of the dropwise addition, the reaction solution was returned to room temperature and stirred overnight. The reaction solution was acidified with diluted hydrochloric acid, and then extracted with ethyl acetate (× 3). The organic layer was washed with a saturated aqueous solution of sodium chloride (× 3) and dried over anhydrous sodium sulfate. Then, after the solvent was distilled off, the residue was subjected to column chromatography and eluted with 1% methanol / chloroform. The corresponding fraction was concentrated to dryness and washed with petroleum ether to give 9.5 g of the title compound as a colorless powder (yield 76%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-1.7 (6H, m), 1.7-2.3 (2H, m), 2.54 (2H, t, J = 7
Hz), 4.23 (1H, dd, J = 5Hz, J = 8Hz), 5.03 (2H, s), 6.92 (2H, p
sd, J = 9Hz), 7.04 (2H, psd, J = 9Hz), 7.37 (5H, m), 8.9 (1H,
brs) 3) 7- (4-benzyloxyphenyl) -2-merca
5- [5- (4-Benzyloxyphenyl) pentyl] thiazolidine-2,4-dione 8.5 obtained with putheptanoic acid 2)
g in ethanol (30 ml) and 10N-NaOH
30 ml was added, and the mixture was heated and refluxed under a nitrogen atmosphere. After 1.5 hours, the reaction was diluted with water and washed with ether. After acidifying the aqueous layer with diluted hydrochloric acid, the aqueous layer was extracted with ethyl acetate,
The organic layer was dried with anhydrous sodium sulfate. After evaporating the solvent, the residue was subjected to column chromatography and eluted with chloroform. The corresponding fractions are concentrated to dryness and washed with petroleum ether to give the title compound 6.35
g was obtained as a colorless powder (81% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.3-2.1 (8H, m), 2.08 (1H, d, J = 9Hz), 2.54 (2H, t,
J = 7Hz), 3.31 (1H, dt, J = 7Hz, J = 9Hz), 5.03 (2H, s), 6.91
(2H, psd, J = 9Hz), 7.04 (2H, psd, J = 9Hz), 7.3-7.5 (5H, m),
8.18 (1H, brs) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
0, 28.6, 31.3, 34.8, 35.1, 40.8, 70.2, 114.8, 127.
4, 127.8, 128.5, 129.2, 134.9, 137.4, 157.0, 178.8 Example 4 7- (4-benzyloxyphenyl) -2-
Mercaptoheptanoic acid (Exemplary Compound No. 1-20) 1) 2- [5- (4-benzyloxyphenyl) penty
-1,3-dithiane- 2-carboxylate ethyl ester
A suspension of 576 mg of oily sodium hydride (60%) in 20 ml of dimethylformamide was added dropwise with 5 ml of a tetrahydrofuran solution of 2.31 g of ethyl 1,3-dithiane-2-carboxylate under ice-cooling. After stirring at room temperature for 30 minutes, a solution of 4.8 g of 5- (4-benzyloxyphenyl) 1-iodopentane in dimethylformamide
5 ml was added dropwise, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and saturated saline in this order, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography. Hexane-ethyl acetate (20: 1)
Elution afforded 3.55 g of the title compound (67% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.31 (3H, t, J = 7 Hz), 1.05-1.82 (8H, m), 1.82-2.2
0 (2H, m), 2.35-2.70 (4H, m), 3.10-3.50 (2H, m), 4.24 (2
H, q, J = 7Hz, J = 14Hz), 5.03 (2H, s), 6.88 (2H, d, J = 9Hz),
7.09 (2H, d, J = 9Hz), 7.23-7.56 (5H, m) 2) 7- (4-benzyloxyphenyl) -2-hydro
Obtained in Kishiheputan acid Echirue ester 1) 2- [5- (4-benzyloxyphenyl) pentyl] -1,3-dithiane-2-carboxylic acid ethyl ester 2.41g was dissolved in acetonitrile 20 ml, under ice-cooling , A 7.7 g solution of N-bromosuccinimide (40 ml of acetonitrile-10 ml of water) was added dropwise,
The mixture was stirred at the same temperature for 30 minutes. 150 ml of hexane-methylene chloride (1: 1) was added to the reaction mixture, and the mixture was washed with 6% sodium bisulfite, saturated aqueous sodium hydrogen carbonate and saturated brine in this order, and the organic layer was dried over anhydrous sodium sulfate. The residue was subjected to column chromatography. Elution with chloroform gave ethyl 5- (4-benzyloxyphenyl) -2-oxoheptanoate.
88 g were obtained as an oil (98% yield). 1.78 g of this oily substance was dissolved in 30 ml of ethanol, 220 mg of sodium borohydride was added little by little under ice cooling, and the mixture was stirred for 30 minutes, and further stirred at room temperature for 1 hour. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography. Elution with chloroform provided 1.5 g of the title compound as an oil (84% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.29 (3H, t, J = 7 Hz), 1.05-1.90 (8H, m), 2.52 (2H,
t, J = 6Hz, J = 9Hz), 4.08-4.2 (1H, m), 4.24 (2H, q, J = 14Hz, J
= 7Hz), 5.11 (2H, s), 6.78-7.09 (2H, m), 7.20-7.56 (7H,
m) 3) 7- (4-benzyloxyphenyl) -2-merca
7- (4-Benzyloxyphenyl) -obtained by butoheptanoic acid 2)
1.5 g of 2-hydroxyheptanoic acid ethyl ester was dissolved in 20 ml of methylene chloride, and triethylamine 5
50 mg was added, and 530 mg of mesyl chloride was added dropwise under ice cooling. After stirring at room temperature for 1 hour, 5% citric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in 20 ml of dimethylformamide, 530 mg of potassium thioacetate was added under ice cooling, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in 10 ml of methanol and 10 ml of tetrahydrofuran, 4 ml of 4N sodium hydroxide was added, and the mixture was stirred at room temperature for 2 hours. Stirred. The reaction mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography. Elution with 1% methanol-chloroform afforded 1.1 g of the title compound (76% yield). Example 5 8- (4-chlorophenyl)
-2-mercaptooctanoic acid (Exemplary Compound No. 1-4
2) 1) 5- [6- (4-chlorophenyl) hexylidene] h
Azolidine-2,4-dione The title compound 1.45 from 1.7 g of 6- (4-chlorophenyl) hexanal in the same manner as 1) of Example 3).
g was obtained (yield 58%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.10-1.90 (6H, m), 2.05-2.40 (2H, m), 2.59 (2H, m
t, J = 7Hz), 7.03 (1H, t, J = 8Hz), 6.95-7.36 (4H, m) 2) 5- [6- (4-chlorophenyl) hexyl] thiazo
Lysine-2,4-dione (Exemplified Compound No. 9-42) 5- [6] obtained in 1) in the same manner as in 2) of Example 3
-(4-chlorophenyl) hexylidene) thiazolidine-
From 1.35 g of 2,4-dione, the title compound 0.8
6 g was obtained (63% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.10-1.80 (8H, m), 1.80-2.30 (2H, m), 2.58 (2H, m
t, J = 7Hz), 4.26 (1H, dd, J = 6Hz, J = 9Hz), 7.03-7.36 (4H,
m), 9.35 (1H, bs) 3) 8- (4-chlorophenyl) -2-mercaptoocta
In the same manner as down 3 acid Example 3), obtained in 2) 5- [6
-(4-chlorophenyl) hexyl] thiazolidine-2,
0.54 g of the title compound was obtained from 0.75 g of 4-dione (78% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.05-2.05 (8H, m), 2.08 (1H, d, J = 9Hz), 2.58 (2H, m
t, J = 8 Hz), 3.34 (1H, dt, J = 7 Hz, J = 9 Hz), 7.04-7.35 (4H, m) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
1, 28.8, 31.1, 35.1, 35.2, 40.8, 128.4, 129.7, 13
1.3, 141.0, 179.6 Example 6 6- (4-Chlorophenyl) -2-mercap
Tohexanoic acid (Exemplified Compound No. 1-3) 1) 5- [4- (4-chlorophenyl) butylidene] thia
Zolidine-2,4-dione In the same manner as in Example 3 1), 4- (4-chlorophenyl) butanal was obtained from 1.17 g of the title compound 0.68.
g was obtained (38% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.66-2.07 (2H, m), 2.07-2.41 (2H, m), 2.65 (2H, m
t, J = 7Hz), 6.95-7.33 (5H, m) 2) 5- [4- (4-chlorophenyl) butyl] thiazoly
Gin-2,4-dione (Exemplified Compound No. 9-3) As in 2) of Example 3, 5- [4-
(4-chlorophenyl) butylidene] thiazolidine-2,
0.64 g of the title compound was obtained from 1.23 g of 4-dione (52% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-1.79 (4H, m), 1.80-2.40 (2H, m), 2.60 (2H, m
t, J = 8Hz), 4.26 (1H, dd, J = 5Hz, J = 9Hz), 7.02-7.30 (4H, m) 3) 6- (4-chlorophenyl) -2-mercaptohex
Sannic acid 5- [4- (4-chlorophenyl) butyl] thiazolidine-2,4-dione in the same manner as in 3) of Example 3.
0.41 g of the title compound was obtained from 0.62 g (yield 73%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.24-2.03 (6H, m), 2.12 (1H, d, J = 9Hz), 2.61 (2H, m
t, J = 7Hz), 3.35 (1H, dt, J = 7Hz, J = 9Hz), 7.04-7.31 (4H,
m) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 26.
7, 30.7, 34.9, 40.6, 125.8, 128.4, 129.7, 131.5, 1
78.7 Example 7 7- (2-chlorophenyl) -2-mercap
Tohepu Tan acid (Compound No. 1-6) 1) 5- [5- (2-chlorophenyl) pentylidene]
Thiazolidine-2,4- dione 2.6 g of the title compound from 4.0 g of 5- (2-chlorophenyl) pentanal in the same manner as 1) of Example 3).
Was obtained (44% yield).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.66 (4H, m), 2.26 (2H, m), 2.26 (2H, m), 2.75 (2
H, pst, J = 7Hz), 7.04 (1H, t, J = 7Hz), 7.1-7.4 (4H, m), 9.0
4 (1H, brs) 2) 5- [5- (2-chlorophenyl) pentyl] thia
Zorijin 2,4 Geo emissions (Compound No. 9-6) In the same manner as in 2) of Example 3 5- [5- (2-chlorophenyl) pentylidene] The title than dione 2.5g 2.0 g of the compound was obtained (80% yield). 1H-NMR (89.55 MHz, δ ppm, CDCl
₃ ): 1.66 (4H, m), 2.26 (2H, m), 2.75 (2H, m), 7.04 (1H,
t, J = 7Hz), 7.1-7.4 (4H, m), 9.04 (1H, brs) 3) 7- (2-Chlorophenyl) -2-mercaptohep
Tanic acid 5- [5- (2-chlorophenyl) pentyl] thiazolidine-2,4-dione in the same manner as in 3) of Example 3
1.2 g of the title compound was obtained from 1.9 g (yield 7).
0%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-2.1 (8H, m), 2.09 (1H, d, J = 9Hz), 2.72 (2H, t,
J = 8Hz), 3.29 (1H, dt, J = 7Hz, J = 9Hz), 7.0-7.5 (4H, m), 8.
95 (1H, brs) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
0, 28.7, 29.4, 33.4, 35.1, 40.8, 126.7, 127.2, 12
9.4, 130.3, 133.9, 139.5, 179.3 Example 8 7- (3-chlorophenyl) -2-mercap
Toheptanoic acid (Exemplified Compound No. 1-7) 1) 5- [5- (3-chlorophenyl) pentylidene]
Thiazolidine-2,4- dione 2.3 g of the title compound from 4.0 g of 5- (3-chlorophenyl) pentanal in the same manner as in 1) of Example 3).
Was obtained as a yellow solid (yield 39%).

1 H-NMR (89.55 MHz, δ ppm, CDC
_{l 3): 1.62 (4H,} m), 2.22 (2H, m), 2.61 (2H, pst, J = 7Hz),
7.02 (1H, t, J = 7Hz), 7.0-7.3 (4H, m), 8.65 (1H, brs) 2) 5- [5- (3-chlorophenyl) pentyl] thia
Zorijin 2,4 Geo emissions (Compound No. 9-7) In the same manner as in 2) of Example 3, 1) obtained in 5- [5
-(3-chlorophenyl) pentylidene] thiazolidine-2,4-dione from 2.2 g, 1.6 g of the title compound
Was obtained as pale yellow candy (yield 73%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-1.8 (6H, m), 2.4-1.8 (2H, m), 2.58 (2H, t, J = 7
Hz), 4.26 (1H, dd, J = 5Hz, J = 8Hz), 7.0-7.3 (4H, m), 9.05 (1
H, brs) 3) 7- (3-chlorophenyl) -2-mercaptohe
Butanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
-(3-chlorophenyl) pentyl] thiazolidine-
From 1.5 g of 2,4-dione, 1.0 g of the title compound
Was obtained as a colorless candy (yield 73%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l_Three): 1.2-2.1 (8H, m), 2.09 (1H, d, J = 9Hz), 2.09 (1H, d,
J = 9Hz), 2.57 (2H, t, J = 7Hz), 3.28 (1H, dt, J = 7Hz, J = 9Hz),
 7.4-6.9 (4H, m), 8.7 (1H, brs) 13C-NMR (22.49 MHz, δ ppm, CDCl_Three): 27.
0, 28.6, 30.8, 35.4, 40.7, 125.9, 126.6, 128.5, 12
9.5, 134.1, 144.5, 177.9 Example 92-mercapto-7-phenylheptanoic acid
(Exemplary Compound No. 1-5) 1)5- (5-phenylpentylidene) thiazolidine-
2,4-dione In the same manner as in 1) of Example 3, 5-phenylpentaner
2.65 g of the title compound from 3.6 g of yellow solid
(46%).

1H-NMR (89.55 MHz, δ ppm, CDC
_{l 3): 1.64 (4H,} m), 2.24 (2H, m), 2.63 (2H, pst, J = 7Hz),
7.03 (1H, t, J = 7Hz), 7.1-7.4 (5H, m), 9.15 (1H, brs) 2) 5- (5-phenylpentyl) thiazolidine-2,
4-dione (Exemplified Compound No. 9-5) 5- (5) obtained in 1) in the same manner as in 2) of Example 3
(Phenylphenylidene) thiazolidine-2,4-dione (2.5 g) gave the title compound (2.2 g) as a pale yellow candy (yield 87%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.3-1.8 (6H, m), 1.8-2.4 (2H, m), 2.67 (2H, t, J = 8
Hz), 4.30 (1H, dd, J = 5Hz, J = 9Hz), 7.1-7.4 (5H, m), 8.86 (1
H, brs) 3) 2-Mercapto-7-phenylheptanoic acid In the same manner as in 3) of Example 3, from 2.0 g of 5- (5-phenylpentyl) thiazolidine-2,4-dione,
1.22 g of the title compound was obtained as a colorless candy (yield 67%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-2.1 (8H, m), 2.09 (1H, d, 9Hz), 2.61 (2H, t, J =
7Hz), 3.31 (1H, dt, J = 7Hz, J = 9Hz), 7.1-7.4 (5H, m), 8.21
(1H, brs) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
1, 28.7, 31.1, 35.1, 35.840.8, 125.7, 128.4, 142.
4, 178.9 Example 10 9- (4-chlorophenyl) -2-mercap
Tononanoic acid (Exemplified Compound No. 1-43) 1) 5- [7- (4-chlorophenyl) heptylidene] thio
Azolidine-2,4-dione In the same manner as 1) of Example 3, the title compound was obtained from 1.52 g of 7- (4-chlorophenyl) heptanal.
13 g were obtained (yield 52%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.10-1.90 (8H, m), 2.05-2.39 (2H, m), 2.59 (2H, m
t, J = 7Hz), 7.04 (1H, t, J = 8Hz), 6.95-7.38 (4H, m) 2) 5- [7- (4-chlorophenyl) heptyl] thiazo
In the same manner as lysine 2,4 Geo down 2 (Compound No. 9-43) Example 3), from 5- [7- (4-chlorophenyl) heptylidene] thiazolidine-2,4-dione 1.08g Thus, 0.68 g of the title compound was obtained (yield: 63%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.10-1.79 (10H, m), 1.79-2.40 (2H, m), 2.57 (2H, m
t, J = 7Hz), 4.26 (1H, dd, J = 6Hz, J = 9Hz), 7.03-7.36 (4H,
m) 3) 9- (4-chlorophenyl) -2-mercaptononane
Acid 5- (7- (4-chlorophenyl) heptyl] thiazolidine-2,4-dione in the same manner as in Example 3) 3).
From 0.65 g, 0.42 g of the title compound was obtained (yield: 70%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.05-2.10 (12H, m), 2.10 (1H, d, J = 9Hz), 2.58 (2
H, t, J = 8Hz), 3.34 (1H, dt, J = 7Hz, J = 9Hz), 7.04-7.36 (4H,
m) Example 11 7- (5-chlorothien-2-yl) -2-
Mercaptoheptanoic acid (Exemplified Compound No. 3-7) 1) 5- [5- (5-Chlorothien-2-yl) pentylyl
Den] thiazolidine-2,4-dione In the same manner as in Example 3 1), 1.84 g of the title compound was obtained from 3.10 g of 5- (5-chlorothien-2-yl) pentanal (yield: 40). %).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.39-1.94 (4H, m), 2.14-2.37 (2H, m), 2.76 (2H, m
t, J = 6Hz), 6.55 (1H, d, J = 4Hz), 6.72 (1H, d, J = 4Hz), 7.03
(1H, t, J = 8Hz ) 2) 5- [5- (5-chlorothien-2-yl) pliers
Ru] thiazolidine-2,4-dione (Exemplary Compound No. 1
1-7) In the same manner as in Example 3-2), 5- [5- (5-chlorothien-2-yl) pentylidene] thiazolidine-2,
1.27 g of the title compound was obtained from 1.8 g of 4-dione (yield 70%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-1.73 (6H, m), 1.78-2.35 (2H, m), 2.74 (2H, t,
J = 7Hz), 4.28 (1H, dd, J = 5Hz, J = 8Hz), 6.54 (1H, d, J = 4H
z), 6.72 (1H, d, J = 4Hz) 3) 7- (5-chlorothien-2-yl) -2-mercap
Toheptanoic acid In the same manner as in Example 3-3 ), 5- [5- (5-chlorothien-2-yl) pentyl] thiazolidine-2,4-
From 1.33 g of dione, 0.82 g of the title compound was obtained as an unemployed oil (yield 66%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.24-2.00 (8H, m), 2.13 (1H, d, J = 9Hz), 2.72 (2H,
t, J = 7Hz), 3.35 (1H, dt, J = 7Hz, J = 9Hz), 6.56 (1H, d, J = 4H
z), 6.71 (1 H, d, J = 4 Hz) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 26.
9, 28.3, 30.1, 31.1, 34.9, 40.7, 123.4, 125.6, 14
4.1, 179.2 Example 12 7- (4-Hydroxyphenyl) -2-me
Lcaptoheptanoic acid (Exemplary Compound No. 1-14) 1) 5- [5- (4-hydroxyphenyl) pentyluri
Den] thiazolidine-2,4 -dione In the same manner as in Example 3 1), the title compound was obtained from 3.5 g of 5- (4-hydroxyphenyl) pentanal.
5 g was obtained as a yellow solid (27% yield).

1H-NMR (89.55 MHz, δ ppm, CD ₃
OD): 1.57 (4H, m), 2.23 (2H, m), 2.53 (2H, pst, J = 7H
z), 6.71 (2H, psd, J = 8Hz), 6.92 (1H, t, J = 8Hz), 6.92 (1H,
t, J = 8Hz), 7.05 (2H, psd, J = 8Hz) 2) 5- [5- (4-hydroxyphenyl) pentyl]
Thiazolidine-2,4- dione (Exemplary Compound No. 9-1)
4) In the same manner as in 2) of Example 3, 5- [5- (4-hydroxyphenyl) pentyllidene] thiazolidine-2,4
From 1.4 g of -dione, 1.23 g of the title compound was obtained as colorless crystals (yield 86%).

1H-NMR (89.55 MHz, δ ppm, CD ₃
OD): 1.2-1.7 (6H, m), 1.7-2.3 (2H, m), 2.51 (2H, t, J =
7Hz), 4.39 (1H, dd, J = 5Hz, J = 8Hz), 6.70 (2H, psd, J = 9Hz),
6.95 (2H, psd, J = 9Hz) 3) 7- (4-hydroxyphenyl) -2-mercapto
Heptanoic acid In the same manner as in Example 3-3), 0.75 g of the title compound was obtained as a colorless solid from 1.1 g of 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4-dione. (75% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-2.1 (8H, m), 2.09 (1H, d, J = 9Hz), 2.52 (2H, t,
J = 7Hz), 3.37 (1H, dt, J = 7Hz, J = 9Hz), 5.65 (2H, brs), 6.7
6 (2H, psd, J = 9 Hz), 7.01 (2H, psd, J = 9 Hz) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
1, 28.6, 31.3, 34.8, 35.2, 40.8, 115.2, 129.4, 13
4.7, 153.5, 178.4 Example 13 2-mercapto-7- (4-methoxy
Nyl) heptanoic acid (Exemplary Compound No. 1-15) 1) 5- [5- (4-methoxyphenyl) pentylidene]
Thiazolidine-2,4-dione In the same manner as 1) of Example 3, the title compound was obtained from 2.1 g of 5- (4-methoxyphenyl) pentanal.
84 g was obtained (58% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.40-1.85 (4H, m), 2.06-2.40 (2H, m), 2.57 (2H, m
t, J = 7Hz), 3.78 (3H, s), 6.83 (2H, d, J = 9Hz), 6.88 (1H, t,
J = 8Hz), 7.10 (2H, d, J = 9Hz) 2) 5- [5- (4-methoxyphenyl) pentyl] thia
Zolidine-2,4-dione (Exemplary Compound No. 9-15) In the same manner as in Example 3-2 ), from 1.75 g of 5- [5- (4-methoxyphenyl) pentylidene] thiazolidine-2,4-dione 1.31 g of the title compound were obtained (yield 74%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-1.83 (6H, m), 1.83-2.40 (2H, m), 2.57 (2H, m
t, J = 7Hz), 3.78 (3H, s), 4.26 (1H, dd, J = 6Hz, J = 9Hz), 6.8
4 (2H, d, J = 9Hz), 7.10 (2H, d, J = 9Hz) 3) 2-mercapto-7- (4-methoxyphenyl) hep
Tanoic acid In the same manner as in 3) of Example 3, 0.76 g of the title compound was obtained as a white solid from 1.05 g of 5- [5- (4-methoxyphenyl) pentyl] thiazolidine-2,4-dione. (Yield 79%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.15-2.10 (8H, m), 2.10 (1H, d, J = 9Hz), 2.57 (2H, m
t, J = 8Hz), 3.32 (1H, dt, J = 7Hz, J = 9Hz), 3.78 (3H, s), 6.8
3 (2H, d, J = 9 Hz), 7.10 (2H, d, J = 9 Hz) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
0, 28.6, 31.3, 34.8, 35.1, 40.8, 55.3, 113.8, 129.
2, 134.6, 157.7, 179.2 Example 14 7- (4-hexyloxyphenyl) -2
-Mercaptoheptanoic acid (Exemplified Compound No. 1-16) 1) 5- [5- (4-hexyloxyphenyl) penty
Riden] thiazolidine- 2,4-dione 2.17 g of the title compound was obtained as a yellow solid from 3.5 g of 5- (4-hexyloxyphenyl) pentanal in the same manner as in 1) of Example 3 (yield). 45
%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 0.91 (3H, pst), 1.2-1.9 (12H, m), 2.25 (2H, m),
2.58 (2H, pst, J = 7Hz), 3.94 (2H, t, J = 6Hz), 6.86 (2H, psd,
J = 9Hz), 6.9-7.2 (3H, m), 8.87 (1H, brs) 2) 5- [5- (4-hexyloxyphenyl) penty
Ru] thiazolidine-2,4 -dione (Exemplary Compound No. 9
-16) In the same manner as in 2) of Example 3, 5- [5- (4-hexyloxyphenyl) pentylidene] thiazolidine-2,
From 2.1 g of 4-dione, 2.0 g of the title compound was obtained as a colorless powder (yield 94%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 0.90 (3H, pst, J = 7 Hz), 1.2-2.3 (8H, m), 2.54 (2H,
t, J = 7Hz), 3.92 (2H, t, J = 6Hz), 4.23 (1H, dd, J = 5,8Hz),
6.82 (2H, psd, J = 9Hz), 7.03 (2H, psd, J = 9Hz), 9.41 (1H, br
s) 3) 7- (4-hexyloxyphenyl) -2-merca
Butoheptanoic acid 5- [5- (4-hexyloxyphenyl) pentyl] thiazolidine-2,4-
From 1.9 g of dione, 1.4 g of the title compound was obtained as a colorless powder (yield 79%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 0.90 (3H, pst), 1.2-2.1 (16H, m), 2.08 (1H, d, J = 9
Hz), 2.53 (2H, t, J = 7Hz), 3.31 (1H, dt, J = 7Hz, J = 9Hz), 3.
92 (2H, t, J = 6Hz), 6.82 (2H, psd, J = 9Hz), 7.02 (2H, psd, J =
9 Hz), 8.32 (1H, brs) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 14.
0, 22.6, 25.8, 27.1, 28.6, 29.4, 31.3, 31.6, 34.9,
35.1, 40.9, 68.2, 114.5, 128.3, 129.2, 134.4, 157.
3, 179.0 Example 15 2-Mercapto-7- (4-phenoxyf
Enyl) heptanoic acid (Exemplary Compound No. 1-19) 1) 5- [5- (4-phenoxyphenyl) pentylide
Thiazolidine-2,4 -dione In the same manner as 1) in Example 3, 2.8 g of 5- (4-phenoxyphenyl) pentanal was used to prepare the title compound.
8 g was obtained as a yellow solid (46% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
_{l 3): 1.62 (4H,} m), 2.24 (2H, m), 2.61 (2H, pst, J = 7Hz),
6.9-7.4 (10H, m), 8.46 (1H, brs) 2) 5- [5- (4-phenoxyphenyl) pentyl]
Thiazolidine-2,4- dione (Exemplary Compound No. 9-1)
9) In the same manner as in 2) of Example 3, 5- [5- (4-phenoxyphenyl) pentylidene] thiazolidine-2,4-
From 1.5 g of dione, 1.2 g of the title compound was obtained as a colorless candy (80% yield).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-1.8 (6H, m), 1.9-2.3 (2H, m), 2.59 (2H, t, J = 5
Hz), 4.25 (1H, dd, J = 5Hz, J = 8Hz), 6.8-7.5 (9H, m) 3) 2-mercapto-7- (4-phenoxyphenyl)
Heptanoic acid In the same manner as in Example 3-3), 1.2 g of the title compound was obtained as a colorless candy from 1.5 g of 5- [5- (4-phenoxyphenyl) pentyl] thiazolidine-2,4-dione. (80% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.3-2.1 (8H, m), 2.11 (1H, d, J = 9Hz), 2.58 (2H, t,
J = 8Hz), 3.29 (1H, dt, J = 7Hz, J = 9Hz), 5.4 (1H, brs), 6.8-
7.5 (9H, m) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
3, 28.8, 31.4, 35.2, 35.5, 41.1, 118.6, 119.1, 12
3.0, 129.7, 129.8, 137.8, 155.2, 175.8 Example 16 7- (2,3-dihydrobenzofuran-5
-Yl) -2-mercaptoheptanoic acid (Exemplified Compound No. 4-13) 1) 5- [5- (2,3-dihydrobenzofuran-5-
Yl) pentylidene] thiazolidine-2,4-dione 1.26 g of the title compound was obtained from 2.22 g of 5- (2,3-dihydrobenzofuran-5-yl) pentanal in the same manner as in 1) of Example 3. (Yield 38
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.40-1.85 (4H, m), 2.10-2.41 (2H, m), 2.57 (2H, m
(t, J = 7Hz), 3.19 (2H, t, J = 9Hz), 4.56 (2H, t, J = 9Hz), 6.70
(1H, d, J = 8Hz), 6.86-7.11 (3H, m) 2) 5- [5- (2,3-dihydrobenzofuran-5-i
L) Pentyl] thiazolidine-2,4-dione (Exemplary Compound No. 12-13) The 5- [5] obtained in 1) in the same manner as in 2) of Example 3
From (1.20 g of-(2,3-dihydrobenzofuran-5-yl) pentylidene) thiazolidine-2,4-dione, 0.91 g of the title compound was obtained (yield: 75).
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.10-1.80 (6H, m), 1.80-2.40 (2H, m), 2.54 (2H, m
t, J = 7Hz), 3.18 (2H, t, J = 9Hz), 4.25 (1H, dd, J = 6Hz, J = 9H
z), 4.54 (2H, t, J = 9Hz), 6.69 (1H, d, J = 8Hz), 6.91 (1H, d,
J = 8Hz), 7.00 (1H, s) 3) 7- (2,3-dihydrobenzofuran-5-yl)-
2-mercaptoheptanoic acid In the same manner as in 3) of Example 3, the title compound 0 was obtained from 0.9 g of 5- [5- (2,3-dihydrobenzofuran-5-yl) pentyl] thiazolidine-2,4-dione. .69
g was obtained as a colorless oil (84% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.10-2.10 (8H, m), 2.10 (1H, d, J = 9Hz), 2.54 (2H, m
t, J = 8Hz), 3.06-3.46 (3H, m), 4.52 (2H, t, J = 9Hz), 6.68
(1H, d, J = 8 Hz), 6.90 (1H, d, J = 8 Hz), 6.99 (1H, s) Example 17 2-mercapto-7- [4- (2-phenene
Tyloxy) phenyl] heptanoic acid (Exemplary Compound No. 1
-28) 1) 5- [5- [4- (2-phenethyloxy) phenyl]
Le] pentylidene] In the same manner as Chia Zorijin 2,4-dione Example 3 1), 5- [4- (2-phenethyloxy) phenyl] pentanal 23.4g than the title compound 15.85g as a yellow solid (50% yield).

1 H-NMR (89.55 MHz, δ ppm, CDC
_{l 3): 1.61 (4H,} m), 2.25 (2H, m), 2.58 (2H, pst, J = 7Hz),
3.08 (2H, t, J = 7Hz), 4.15 (2H, t, J = 7Hz), 6.80 (2H, psd, J
= 9Hz), 6.9-7.2 (3H, m), 7.28 (5H, m), 8.32 (1H, brs) 2) 5- [5- [4- (2-phenethyloxy) phenyl)
Le] pentyl] thiazol Jin-2,4-dione (Compound No. 9-28) In the same manner as in 2) of Example 3, obtained in 1) 5- [5
From 10.85 g of-[4- (2-phenethyloxy) phenyl] pentylidene] thiazolidine-2,4-dione, 10.3 g of the title compound was obtained as a pale yellow solid (65% yield).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-1.7 (6H, m), 2.3-1.7 (2H, m), 2.54 (2H, t, J = 7
Hz), 3.08 (2H, t, J = 7Hz), 4.0-4.4 (3H, m), 6.83 (2H, psd,
J = 9Hz), 7.02 (2H, psd, J = 9Hz), 7.28 (5H, m), 8.25 (1H, br
s) 3) 2-mercapto-7- [4- (2-phenethyloxy )
C) Phenyl] heptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
5.8 g of the title compound was obtained from 9.0 g of-[4- (2-phenethyloxy) phenyl] pentyl] thiazolidine-2,4-dione (yield 69%). 1H-NMR (89.55 MHz, δ ppm, CDCl ₃ ): 1.2-
2.1 (8H, m), 2.07 (1H, d, J = 9Hz), 2.53 (2H, t, J = 7Hz), 3.0
7 (2H, t, J = 7Hz), 3.25 (1H, dt, J = 7Hz, J = 9Hz), 4.14 (2H, t,
J = 7Hz), 6.83 (2H, psd, J = 9Hz), 7.03 (2H, psd, J = 9Hz), 7.
27 (5H, m), 8.05 (1H, brs) 13C-NMR (22.49 MHz, δppm, CDCl ₃ ): 27.
1, 28.6, 31.3, 34.8, 35.2, 35.9, 40.7, 68.8, 114.
6, 126.5, 128.5, 129.0, 129.2, 134.7, 138.4, 157.
0, 178.4 Example 18 2-mercapto-7- (2-naphthyl)
Butanoic acid (exemplified compound No. 2-5) 1) 5- [5- (2-naphthyl) pentylidene] thiazo
Lysine-2,4-dione In the same manner as in 1) of Example 3, 2.8 g of the title compound was obtained from 2.46 g of 5- (2-naphthyl) pentanal (yield 78%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.30-1.95 (4H, m), 2.05-2.40 (2H, m), 2.78 (2H, m
(t, J = 7Hz), 7.00 (1H, t, J = 8Hz), 7.20-7.50 (3H, m), 7.60
(1H, brs), 7.65-7.90 (3H, m) 2) 5- [5- (2-naphthyl) pentyl] thiazolidi
In the same manner as down-2,4-dione 2 (Compound No. 10-5) Example 3), 1) obtained in 5- [5
-(2-naphthyl) pentylidene] thiazolidine-2,
From 2.8 g of 4-dione, 2.1 g of the title compound was obtained (yield: 75%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.25-2.25 (8H, m), 2.75 (2H, t, J = 7), 4.20 (1H, d
d, J = 4Hz, 8Hz), 7.20-7.55 (3H, m), 7.58 (1H, brs), 7.65-
7.90 (3H, m) 3) 2-Mercapto-7- (2-naphthyl) heptanoic acid In the same manner as in 3) of Example 3, 5- [5] obtained in 2).
-(2-naphthyl) pentyl] thiazolidine-2,4-
From 2.08 g of dione, 1.2 g of the title compound was obtained as a colorless solid (63% yield).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.25-2.05 (8H, m), 2.08 (1H, d, J = 9Hz), 2.76 (2H, m
t, J = 8Hz), 3.33 (1H, dt, J = 7Hz, J = 9Hz), 7.20-7.50 (3H,
m), 7.59 (1H, brs), 7.65-7.90 (3H, m), 7.80 (1H, brs) 13C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.0
4, 28.61, 30.88, 35.00, 35.87, 40.74, 124.99, 125.
81, 126.24, 127.33, 127.54, 127.76, 131.93, 133.5
5, 139.90, 179.12 Example 19 2-mercapto-7- [4- (3- phenyl
L-propoxy) phenyl] heptanoic acid (Exemplary Compound No. 1-29) 1) 5- [5- [4- (3-phenylpropoxy) phenyl
L] pentylidene} -thiazolidine-2,4-dione 2.25 g of the title compound was obtained from 2.96 g of 5- [4- (3-phenylpropoxy) phenyl] pentanal in the same manner as 1) of Example 3). (Yield 57
%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.38-1.87 (4H, m), 1.90-2.40 (4H, m), 2.57 (2H,
t, J = 7Hz), 2.82 (2H, t, J = 8Hz), 3.95 (2H, t, J = 6Hz), 6.81
(2H, d, J = 8Hz), 6.92-7.18 (3H, m), 7.23 (5H, s) 2) 5- [5- [4- (3-phenylpropoxy) fe
Nyl ] pentyl] -thiazolidine -2,4-dione (Exemplary Compound No. 9-29) The 5- [5] obtained in 1) in the same manner as in 2) of Example 3
From 2.2 g of-[4- (3-phenylpropoxy) phenyl] pentylidene] -thiazolidine-2,4-dione, 1.43 g of the title compound was obtained (yield: 65).
%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.10-1.85 (8H, m), 1.85-2.35 (4H, m), 2.56 (2H,
(t, J = 7Hz), 2.81 (2H, t, J = 8Hz), 3.94 (2H, t, J = 6Hz), 4.25
(1H, dd, J = 5Hz, J = 9Hz), 6.81 (2H, d, J = 8Hz), 7.08 (2H, d, J
= 8Hz), 7.23 (5H, s) 3) 2-mercapto-7- [4- (3-phenylpropo
) Phenyl] 3 hepta phosphate Example 3) and in the same manner, obtained in 2) 5- [5
-[4- (3-phenylpropoxy) phenyl] pentylidene] -thiazolidine-2,4-dione 1.33 g
Thus, 0.82 g of the title compound was obtained as a white solid (yield: 66%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.10-1.95 (8H, m), 1.95-2.22 (3H, m), 2.54 (2H,
t, J = 8Hz), 2.80 (2H, t, J = 8Hz), 3.30 (1H, dt, J = 7Hz, J = 9H
z), 3.92 (2H, t, J = 6 Hz), 6.68-7.40 (9H, m) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
0, 28.5, 30.9, 31.2, 32.2, 34.8, 35.1, 40.7, 67.0,
114.5, 125.8, 128.3, 128.4, 129.2, 134.5, 141.5,
157.1, 179.1 Example 20 2-mercapto-7- (4-biphenyli)
1) Heptanoic acid (Exemplified Compound No. 1-18) 1) 5- [5- (4-Biphenylyl) pentylidene] thio
Azolidine-2,4 1 di one Example 3) in analogy to 5- (4-biphenylyl) than pentanal 5.4 g, the title compound 3.2
g was obtained as a yellow solid (52% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.66 (4H, m), 2.26 (2H, m), 2.68 (2H, pst, J = 7Hz),
7.03 (1H, t, J = 8Hz), 7.1-7.7 (9H, m), 9.25 (1H, brs) 2) 5- [5- (4-biphenylyl) pentyl] thiazo
Lysine-2,4-dione (Exemplified Compound No. 9-18) 5- [5] obtained in 1) in the same manner as in 2) of Example 3
-(4-biphenylyl) pentylidene] thiazolidine-
From 3.8 g of 2,4-dione, 3.1 g of the title compound was obtained as a colorless solid (yield 82%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.8-1.8 (6H, m), 1.8-2.3 (2H, m), 2.65 (2H, t, J = 8
Hz), 4.24 (1H, dd, J = 4Hz, J = 8Hz), 7.1-7.6 (9H, m), 9.10 (1
H, brs) 3) 2-mercapto-7- (4-biphenylyl) hepta
In the same manner as down 3 acid Example 4), obtained in 2) 5- [5
-(4-biphenylyl) pentyl] thiazolidine-2,
From 3.0 g of 4-dione, 1.74 g of the title compound was obtained as a colorless solid (63% yield).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-2.0 (8H, m), 2.08 (1H, d, J = 9Hz), 2.64 (2H, t,
J = 8Hz), 3.31 (1H, dt, J = 8Hz, J = 9Hz), 7.2-7.6 (9H, m), 9.
18 (1H, brs) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
1, 28.7, 31.0, 35.1, 35.4, 40.8, 127.0, 128.7, 12
8.8, 138.7, 141.1, 141.6, 179.2 Example 21 6- (4-benzyloxyphenyl) -2
-Mercaptohexanoic acid (Exemplified Compound No. 1-4) 1) 5- [4- (4-benzyloxyphenyl) butyric
Den] thiazolidine -2 in the same manner as 4-1-dione Example 3), from 4- (4-benzyloxyphenyl) butanal 22.6 g, the title compound 18.5g as a yellow solid (yield: 58
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.84 (2H, q, J = 7 Hz), 2.17 (2H, pst, J = 7 Hz), 2.61
(2H, pst, J = 7Hz), 5.04 (2H, s), 6.8-7.2 (5H, m), 7.38 (5
H, m), 9.10 (1H, brs) 2) 5- [4- (4-benzyloxyphenyl) buty
Ru] thiazolidine-2,4 -dione (Exemplary Compound No. 9
-4) 5- [4] obtained in 1) in the same manner as in 2) of Example 3.
From (18.5 g of-(4-benzyloxyphenyl) butylidene] thiazolidine-2,4-dione, 12.0 g of the title compound was obtained as a colorless solid (yield: 65).
%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.3-2.3 (6H, m), 2.61 (2H, t, J = 7Hz), 4.23 (1H, d
d, J = 5Hz, J = 8Hz), 5.03 (2H, s), 6.90 (2H, psd, J = 9Hz), 7.
06 (2H, psd, J = 9Hz), 7.38 (5H, m), 8.90 (1H, brs) 3) 6- (4-benzyloxyphenyl) -2-merca
Ptohexanoic acid 5- [4] obtained in 2) in the same manner as in 3) of Example 3
-(4-benzyloxyphenyl) butyl] thiazolidine-2,4-dione from 9.0 g of the title compound.
2 g were obtained as a colorless powder (74% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.3-2.0 (6H, m), 2.08 (1H, d, J = 9Hz), 2.56 (2H, t,
J = 7Hz), 3.33 (1H, dt, J = 7Hz, J = 9Hz), 5.03 (2H, s), 6.88
(2H, psd, J = 9Hz), 7.08 (2H, psd, J = 9Hz), 7.38 (5H, m), 8.
75 (1H, brs) 13C- NMR (22.49MHz, δppm, CDCl 3): 26.
8, 30.9, 34.7, 35.0, 40.7, 70.2, 114.9, 127.4, 12
7.8, 128.5, 129.2, 134.5, 137.3, 157.1, 178.8 Example 22 7- (6-benzyloxy-2-naphthy
L) -2-Mercaptoheptanoic acid (Exemplary Compound No. 2-
20) 1) 5- [5- (6-benzyloxy-2-naphthyl)
Pentylidene] thiazol Jin-2,4-dione Example 3 1) and in the same manner, from 5- (6-benzyloxy-2-naphthyl) pentanal 4.4 g, the title compound 4.11g as a colorless solid (Yield 6
9%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.45-1.95 (4H, m), 2.10-2.40 (2H, m), 2.77 (2H, m
t, J = 7Hz), 5.17 (2H, s), 6.97 (1H, t, J = 7Hz), 7.10-7.80
(11H, m) 2) 5- [5- (6-benzyloxy-2-naphthyl)
Pentyl] thiazolidine -2,4-dione (Exemplary Compound No. 10-20) The 5- [5] obtained in 1) in the same manner as in 2) of Example 3
-(6-benzyloxy-2-naphthyl) pentylidene] thiazolidine-2,4-dione from 4.06 g,
3.97 g of the title compound were obtained as a colorless solid (yield 97%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.25-2.20 (8H, m), 2.73 (2H, t, J = 7Hz), 4.20 (1H,
dd, J = 4Hz, J = 9Hz), 5.16 (2H, s), 7.10-7.80 (11H, m) 3) 7- (6-benzyloxy-2-naphthyl) -2-
Mercaptoheptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
-(6-benzyloxy-2-naphthyl) pentyl] thiazolidine-2,4-dione (3.92 g) gave 1.4 g of the title compound as a colorless solid (yield 38).
%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.15-2.00 (8H, m), 2.07 (1H, d, J = 9Hz), 2.73 (2H, m
t, J = 7Hz), 3.32 (1H, dt, J = 7Hz, J = 9Hz), 5.15 (2H, s), 6.7
0 (1H, brs), 7.10-7.75 (11H, m) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
04, 28.61, 30.99, 35.06, 35.65, 40.69, 70.00, 107.
17, 118.93, 126.13, 126.68, 127.49, 127.76, 127.92,
128.52, 128.89, 129.17, 132.85, 136.97,137.73, 15
6.20, 178.85 Example 23 2-mercapto-7- [4- [1- (4-
Methylphenyl) ethoxy] phenyl] heptanoic acid (Exemplary Compound No. 1-27) 1) 5- [5- [4- [1- (4-methylphenyl) e
Toxy] phenyl] pentylidene] thiazolidine-2,
4-dione In the same manner as in Example 3 1), 5- [4- [1- (4-
Methylphenyl) ethoxy] phenyl] pentanal
From 4.2 g, 2.6 g of the title compound was obtained as a yellow candy (46% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.3-1.8 (4H, m), 1.60 (3H, d, J = 6Hz), 2.19 (2H, m
m), 2.31 (3H, s), 2.51 (2H, m), 5.23 (1H, q, J = 6Hz), 6.76
(2H, psd, J = 9 Hz), 6.9-7.3 (7H, m), 9.02 (1H, brs) 2) 5- [5- [4- [1- (4-methylphenyl) e
Toxy] phenyl] pentyl] thiazolidine-2,4-
Dione (Exemplified Compound No. 9-27) 5- [5] obtained in 1) in the same manner as in 2) of Example 3
-[4- [1- (4-methylphenyl) ethoxy] phenyl] pentylidene] thiazolidine-2,4-dione
From 2.6 g, 2.2 g of the title compound was obtained as a colorless candy (65% yield).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-1.7 (6H, m), 1.59 (3H, d, J = 6Hz), 1.7-2.2 (2
H, m), 2.31 (3H, s), 2.48 (2H, t, J = 7Hz), 4.22 (1H, dd, J = 4
Hz, J = 8Hz), 5.22 (1H, q, J = 6Hz), 6.79 (2H, psd, J = 9Hz), 6.
94 (2H, psd, J = 9Hz), 7.14 (2H, psd, J = 8Hz), 7.25 (2H, psd,
J = 8Hz), 8.52 (1H, brs) 3) 2-mercapto-7- [4- [1- (4-methylf
Enyl) ethoxy] phenyl] heptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
-[4- [1- (4-methylphenyl) ethoxy] phenyl] pentyl] thiazolidine-2,4-dione 2.2
From this g, 1.48 g of the title compound was obtained as a colorless candy (yield: 72%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-2.0 (8H, m), 1.59 (3H, d, J = 6Hz), 2.06 (1H, d,
J = 9Hz), 2.31 (3H, s), 2.48 (2H, pst, J = 8Hz), 3.30 (1H, d
t, J = 8,9Hz), 5.23 (1H, q, J = 6Hz), 6.79 (2H, psd, J = 8Hz),
6.94 (2H, psd, J = 8Hz), 7.13 (2H, psd, J = 8Hz), 7.22 (2H, ps
d, J = 8 Hz), 8.24 (1H, brs) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 21.
1, 24.4, 27.0, 28.6, 31.2, 34.8, 35.1, 40.8, 76.0,
115.9, 125.5, 129.1, 129.2, 134.5, 136.9, 140.5,
156.2, 179.0 Example 24 7- [4- (4-chlorobenzyloxy) phenyl
Enyl] -2-mercaptoheptanoic acid (Exemplary Compound No. 1-26) 1) 5- [5- [4- (4-chlorobenzyloxy ) phenyl]
L] pentylidene] thiazolidine-2,4-dione 3.05 g of 5- [4- (4-chlorobenzyloxy) phenyl] pentanal in the same manner as in 1) of Example 3).
As a result, 1.71 g of the title compound was obtained (yield: 42).
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.35-1.86 (4H, m), 2.06-2.37 (2H, m), 2.57 (2H, m
t, J = 7Hz), 5.00 (2H, s), 6.82-7.15 (4H, m), 7.35 (4H, s) 2) 5- [5- [4- (4-chlorobenzyloxy)
Nyl] pentyl] thiazolidine-2,4-dione (Exemplified Compound No. 9-26) In the same manner as in Example 3, 2),
From 1.70 g of 5- [5- [4- (4-chlorobenzyloxy) phenyl cpentylidene] thiazolidine-2,4-dione obtained in 1), the title compound 1.
46 g were obtained (85% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.15-1.88 (6H, m), 1.88-2.32 (2H, m), 2.55 (2H, m
t, J = 7Hz), 4.24 (1H, dd, J = 5Hz, J = 9Hz), 5.00 (2H, s), 6.8
6 (2H, d, J = 9Hz), 7.09 (2H, d, J = 9Hz), 7.35 (4H, s) 3) 7- [4- (4-chlorobenzyloxy) phenyl]
2-mercaptoheptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3.
-[4- (4-chlorobenzyloxy) phenyl] pentyl] thiazolidine-2,4-dione from 1.35 g,
0.94 g of the title compound was obtained as a white solid (74% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.15-2.00 (8H, m), 2.08 (1H, d, J = 9Hz), 2.55 (2H, m
t, J = 8Hz), 3.32 (1H, dt, J = 7Hz, J = 9Hz), 4.99 (2H, s), 6.8
6 (2H, d, J = 9Hz), 7.09 (2H, d, J = 9Hz), 7.34 (4H, s) Example 25 2-mercapto-7- [4- (phenoxy
Methyl) phenyl] heptanoic acid (Exemplary Compound No. 1-3
0) 1) 5- [5- [4- (phenoxymethyl) phenyl]
Pentylidene] thiazol Jin-2,4-dione Example 3 1) and in the same manner, from 5- [4- (phenoxymethyl) phenyl] pentanal 4.3 g, the title compound 3.46g as a yellow solid (Yield 5
5%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.63 (4H, m), 2.25 (2H, m), 2.64 (2H, pst, J = 7Hz),
5.03 (2H, s), 6.8-7.5 (10H, m), 9.01 (1H, brs) 2) 5- [5- [4- (phenoxymethyl) phenyl]
Pentyl] thiazolidine -2,4-dione (Exemplified Compound No. 9-30) The same procedure as in Example 3-2) was carried out to obtain 5- [5) obtained in 1).
From 3.2 g of-[4- (phenoxymethyl) phenyl] pentylidene] thiazolidine-2,4-dione, 2.5 g of the title compound was obtained as a colorless solid (yield: 7).
8%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-1.8 (6H, m), 1.8-2.3 (2H, m), 2.62 (2H, t, J = 8
Hz), 4.24 (1H, dd, J = 4Hz, J = 8Hz), 5.02 (2H, s), 6.8-7.5 (9
H, m), 8.71 (1H, brs) 3) 2-mercapto-7- [4- (phenoxymethyl)
Phenyl] heptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3.
From 2.0 g of-[4- (phenoxymethyl) phenyl] pentyl] thiazolidine-2,4-dione, 1.33 g of the title compound was obtained as a colorless powder (yield: 72).
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-2.0 (8H, m), 2.08 (1H, d, J = 9Hz), 2.61 (2H, t,
J = 8Hz), 3.36 (1H, dt, J = 7Hz, J = 9Hz), 5.02 (2H, s), 6.8-
7.5 (9H, m), 7.61 (1H, brs) 13C-NMR (22.49MHz, δppm, CDCl 3): 27.
1, 28.7, 31.0, 35.1, 35.5, 40.7, 70.0, 115.0, 120.
9, 127.7, 128.6, 129.4, 134.5, 142.3, 159.0, 178.6 Example 26 5- [4- (benzyloxy) phenyl]
-2-mercaptopentanoic acid (Exemplified Compound No. 1-2) 1) 5- [3- [4- (benzyloxy) phenyl] p
Ropiriden] thiazolidine down-2,4-dione Example 3 1) were used to give 3- [4- (benzyloxy) phenyl] than propanal 3.73 g, the title compound 2.5g as a yellow solid (Yield 48
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 2.52 (2H, pst, J = 7 Hz), 2.78 (2H, pst, J = 7 Hz), 5.0
3 (2H, s), 6.8-7.2 (5H, m), 7.37 (5H, m), 9.20 (1H, brs) 2) 5- [3- [4- (benzyloxy) phenyl] p
[Ropyl] thiazolidine- 2,4-dione (Exemplified Compound No. 9-2) 5- [3] obtained in 1) in the same manner as in 2) of Example 3
-[4- (benzyloxy) phenyl] propylidene]
From 2.4 g of thiazolidine-2,4-dione, 2.0 g of the title compound was obtained as a colorless solid (yield: 83).
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.5-2.3 (4H, m), 2.61 (2H, t, J = 7Hz), 4.26 (1H, d
d, J = 5Hz, J = 8Hz), 5.04 (2H, s), 6.90 (2H, psd, J = 9Hz), 7.
06 (2H, psd, J = 9Hz), 7.39 (5H, m), 8.82 (1H, brs) 3) 2-mercapto-5- [4- (benzyloxy) phenyl
Eniru] In the same manner as pentane 3 acid Example 3), obtained in 2) 5- [3
From 1.8 g of-[4- (benzyloxy) phenyl] propyl] thiazolidine-2,4-dione, 1.2 g of the title compound was obtained as a colorless powder (72%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.5-2.1 (4H, m), 2.08 (1H, d, J = 9Hz), 2.58 (2H, t,
J = 7Hz), 3.33 (1H, dt, J = 7Hz, J = 9Hz), 5.03 (2H, s), 7.05
(2H, psd, J = 9Hz ), 7.38 (5H, m), 8.75 (1H, brs) 13C-NMR (22.49MHz, δppm, CDCl 3): 29.
0, 34.4, 34.6, 40.7, 70.2, 114.9, 127.4, 127.9, 12
8.5, 129.2, 133.9, 137.2, 157.2, 178.8 Example 27 2-mercapto-7- [4- (1-phenene
Tyloxy) phenyl] heptanoic acid (Exemplary Compound No. 1
-36) 1) 5- [5- [4- (1-phenethyloxy) phenyl]
L] pentylidene] thiazolidine-2,4-dione From 3.5 g of 5- [4- (1-phenethyloxy) phenyl] pentanal in the same manner as in 1) of Example 3,
2.6 g of the title compound was obtained as a yellow candy (55% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.4-1.8 (4H, m), 1.61 (3H, d, J = 6Hz), 2.19 (2H, m
m), 2.54 (2H, pst, J = 7Hz), 5.25 (1H, q, J = 6Hz), 6.77 (2H,
psd, J = 9 Hz), 6.94 (3H, m), 7.33 (5H, m) 2) 5- [5- [4- (1-phenethyloxy) phenyi
L] pentyl] thiazolidine-2,4-dione (Exemplified Compound No. 9-36) The 5- [5] obtained in 1) in the same manner as in 2) of Example 3
-[4- (1-phenethyloxy) phenyl] pentylidene] thiazolidine-2,4-dione
1.8 g of the title compound was obtained as a colorless candy (yield 72%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-1.7 (6H, m), 1.61 (3H, d, J = 6Hz), 1.7-2.2 (2
H, m), 2.49 (2H, t, J = 7Hz), 4.22 (1H, dd, J = 4Hz, J = 8Hz),
5.22 (1H, q, J = 6Hz), 6.73 (2H, psd, J = 9Hz), 6.98 (2H, psd,
J = 9Hz), 7.33 (5H, m), 8.56 (1H, brs) 3) 2-mercapto-7- [4- (1-phenethyloxy )
C) Phenyl] heptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
From 1.7 g of-[4- (1-phenethyloxy) phenyl] pentyl] thiazolidine-2,4-dione, 1.1 g of the title compound was obtained as a pale yellow candy (yield 70%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-2.0 (8H, m), 1.59 (3H, d, J = 6Hz), 2.06 (1H, d,
J = 9Hz), 2.48 (2H, pst, J = 8Hz), 3.30 (1H, dt, J = 8Hz, J = 9H
z), 5.25 (1H, q, J = 6Hz), 6.78 (2H, psd, J = 9Hz), 6.98 (2H,
psd, J = 9Hz), 7.33 (5H, m), 7.83 (1H, brs) 13C-NMR (22.49MHz, δppm, CDCl 3): 24.
4, 27.0, 28.6, 31.2, 34.8, 35.1, 40.7, 76.1, 115.
8, 125.5, 127.3, 128.5, 129.1, 134.5, 143.5, 156.
1,178.6 Example 28 7- (4-Cyclohexylmethoxyphenyl)
L) -2-Mercaptoheptanoic acid (Exemplary Compound No. 1-
17) 1) 5- [5- (4-cyclohexylmethoxyphenyl )
Le) pentylidene] thiazole-2,4-dione Example 3 1) and in the same manner, from 5- (4-cyclohexyl-methoxyphenyl) pentanal 6.2 g, the title compound 5.8g was obtained (yield: 69%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 0.8-2.30 (17H, m), 2.54 (2H, t, J = 7Hz), 3.72 (2H,
d, J = 6Hz), 6.86 (2H, d, J = 9Hz), 7.06 (2H, d, J = 9Hz) 2) 5- [5- (4-cyclohexylmethoxyphenyl)
Pentyl] thiazolidine-2,4 (Exemplary Compound No. 9-
17) 5- [5] obtained in 1) in the same manner as in 2) of Example 3
From 4- (cyclohexylmethoxyphenyl) pentylidene] thiazolidine-2,4-dione (5.8 g), 4.87 g of the title compound was obtained as a colorless solid (yield 84%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 0.80-2.30 (19H, m), 2.54 (2H, t, J = 7Hz), 3.72 (2
H, d, J = 6Hz), 4.25 (1H, dd, J = 4Hz, J = 9Hz), 6.80 (2H, d, J = 9
Hz), 7.06 (2H, d, J = 9 Hz) 3) 7- (4-cyclohexylmethoxyphenyl) -2-
Mercaptoheptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
-(4-cyclohexylmethoxyphenyl) pentyl]
From 2.2 g of thiazolidine-2,4-dione, 1.2 g of the title compound was obtained as a colorless solid (yield: 58).
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 0.8-2.05 (19H, m), 2.08 (1H, d, J = 9Hz), 2.53 (2H,
t, J = 7Hz), 3.32 (1H, dt, J = 7Hz, J = 9Hz), 3.72 (2H, d, J = 6H
z), 6.80 (2H, d, J = 9Hz), 7.06 (2H, d, J = 9Hz), 8.65 (1H, br
s) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 25.8
4, 26.60, 27.09, 28.55, 29.96, 31.37, 34.84, 35.1
1, 37.76, 40.80, 73.58, 114.37, 129.17, 134.26, 15
7.45, 179.28 Example 29 6- (4-chlorophenoxy) -2-mer
Captohexanoic acid (Exemplary Compound No. 5-1) 1) 5- [4- (4-chlorophenoxy) butylidene]
Thiazolidine-2,4- dione The title compound 4.3 was obtained from 4.0 g of 4- (4-chlorophenoxy) butanal in the same manner as 1) of Example 3).
g was obtained (67% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.70-2.20 (2H, m), 2.25-2.60 (2H, m), 3.95 (2H, m
t, J = 6Hz), 6.80 (2H, d, J = 9Hz), 7.23 (2H, d, J = 9Hz), 7.06
(1H, t, J = 8Hz) 2) 5- [4- (4-chlorophenoxy) butyl] thia
Zorijin 2,4 Geo emissions (Compound No. 13-1) In the same manner as in 2) of Example 3, obtained in 1) 5- [4
-(4-chlorophenoxy) butylidene] thiazolidine-2,4-dione from 4.2 g to 2.0 g of the title compound
Was obtained (47% of yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.40-2.30 (6H, m), 3.90 (2H, t, J = 6Hz), 4.28 (1H,
dd, J = 4Hz, J = 9Hz), 6.77 (2H, d, J = 9Hz), 7.20 (2H, d, J = 9H
z) 3) 6- (4-Chlorophenoxy) -2-mercaptohe
Xanic acid 5- [4] obtained in 2) in the same manner as in 3) of Example 3
-(4-chlorophenoxy)] butyl] thiazolidine-
From 2.0 g of 2,4-dione, 0.85 g of the title compound
Was obtained as a colorless solid (46% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.45-2.10 (6H, m), 2.12 (1H, d, J = 9Hz), 3.40 (1H, m
dt, J = 7Hz, J = 9Hz), 3.90 (2H, t, J = 6Hz), 5.20 (1H, brs),
6.80 (1H, d, J = 9 Hz), 7.23 (1 H, d, J = 9 Hz) Example 30 6- (4 -Iodophenoxy ) -2-mer
Captohexanoic acid (Exemplified Compound No. 5-3) 1) 5- [4- (4-Iodophenoxy) butylidene]
Thiazolidine-2,4- dione The title compound 4.8 was obtained from 4- (4-iodophenoxy) butanal 7.0 g in the same manner as in Example 3 1).
g was obtained (51% yield). 2) 5- [4- (4-iodophenoxy) butyl] thia
Zorijin 2,4 Geo emissions (Compound No. 13-3) In the same manner as in 2) of Example 3, obtained in 1) 5- [4
-(4-Iodophenoxy) butylidene] thiazolidine-2,4-dione from 4.8 g, 3.0 g of the title compound
Was obtained (yield 62%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.50-2.40 (6H, m), 3.92 (2H, t, J = 6Hz), 4.30 (1H,
dd, J = 4Hz, J = 9Hz), 6.65 (2H, d, J = 9Hz), 7.55 (2H, d, J = 9H
z), 9.25 (1H, brs) 3) 6- (4-Iodophenoxy) -2-mercaptohe
Xanic acid 5- [4] obtained in 2) in the same manner as in 3) of Example 3
-(4-Iodophenoxy) butyl] thiazolidine-
From 2.8 g of 2,4-dione, 1.8 g of the title compound
Was obtained as a colorless solid (yield 69%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.45-2.10 (6H, m), 2.12 (1H, d, J = 9Hz), 3.35 (1H, m
dt, J = 7Hz, J = 9Hz), 3.90 (2H, t, J = 6Hz), 6.65 (1H, d, J = 9H
z), 7.54 (1H, d, J = 9 Hz) Example 31 2-mercapto-6- (4 -phenylphene)
Nonoxy) hexanoic acid (Exemplary Compound No. 5-11) 1) 5- [4- (4-phenylphenoxy) butylide
Thiazolidine-2,4 -dione The title compound 3.3 was obtained from 4.5 g of 4- (4-phenylphenoxy) butanal in the same manner as in 1) of Example 3).
g was obtained (yield 52%). 2) 5- [4- (4-phenylphenoxy) butyl] thio
Azolidine-2,4-one (Compound No. 13-1
1) 5- [4] obtained in 1) in the same manner as in 2) of Example 3
-(4-phenylphenoxy) butylidene] thiazolidine-2,4-dione from 3.3 g of the title compound.
0 g was obtained (60% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.45-2.45 (6H, m), 3.96 (2H, t, J = 6Hz), 4.31 (1H,
dd, J = 4Hz, J = 9Hz), 6.75-7.40 (9H, m) 3) 2-mercapto-6- (4-phenylphenoxy)
Hexanoic acid 5- [4] obtained in 2) in the same manner as in 3) of Example 3
-(4-phenylphenoxy) butyl] thiazolidine-
From 2.0 g of 2,4-dione, 1.5 g of the title compound was obtained as a white solid (yield 81%).

1 H-NMR (89.55 MHz, δ ppm, CDC
_{l 3): 1.40-2.10 (6H,} m), 2.14 (1H, d, J = 9Hz), 3.40 (1H,
dt, J = 7Hz, J = 9Hz), 3.95 (2H, t, J = 6Hz), 6.75-7.40 (9H,
m), 8.50 (1H, brS) Example 32 6- (4-Benzyloxyphenoxy)-
2-mercaptohexanoic acid (Exemplified Compound No. 5-13) 1) 5- [4- (4-benzyloxyphenoxy) butyi
Riden] thiazolidine- 2,4-dione 2.1 g of the title compound was obtained from 2.3 g of 4- (4-benzyloxyphenoxy) butanal in the same manner as 1) of Example 3 (yield 67%). .

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.70-2.55 (4H, m), 3.92 (2H, t, J = 5Hz), 5.00 (2H,
s), 6.70-7.05 (4H, m), 7.08 (1H, t, J = 8Hz), 7.25-7.50 (5
H, m) 2) 5- [4- (4-benzyloxyphenoxy) buty
Ru] thiazolidine-2,4 -dione (Exemplary Compound No. 1
3-13) 5- [4] obtained in 1) in the same manner as in 2) of Example 3
From (2.1 g of-(4-benzyloxyphenoxy) butylidene] thiazolidine-2,4-dione, 1.6 g of the title compound was obtained as a colorless solid (yield 75%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.45-2.40 (6H, m), 3.92 (2H, t, J = 6Hz), 4.28 (1H, m
(dd, J = 4Hz, J = 9Hz), 5.00 (2H, s), 6.70-7.05 (4H, m), 7.25-
7.50 (5H, m) 3) 6- (4-benzyloxyphenoxy) -2-mer
Captohexanoic acid 5- [4] obtained in 2) in the same manner as in 3) of Example 3
-(4-benzyloxyphenoxy) butyl] thiazolidine-2,4-dione from 1.5 g of the title compound
1.1 g were obtained as a colorless solid (79% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.45-2.10 (6H, m), 2.12 (1H, d, J = 9Hz), 3.36 (1H,
dt, J = 7Hz, J = 9Hz), 3.90 (2H, t, J = 6Hz), 5.00 (2H, s), 6.7
0-7.05 (4H, m), 7.25-7.50 (5H, m), 8.00 (1H, brs) 13C-NMR (22.49MHz, δppm, CDCl 3): 23.9
5, 28.82, 34.84, 40.74, 68.11, 70.76, 115.46, 115.
89, 127.49, 127.87, 128.52, 137.30, 153.01, 153.2
8,178.80 Example 33 6- [4- (4-Chlorobenzyloxy)
Phenoxy] -2-mercaptohexanoic acid (Exemplary Compound No. 5-16) 1) 5- [4- [4- (4-chlorobenzyloxy ) phenyl ]
[Enoxy] butylidene] thiazolidine-2,4-dione In the same manner as 1) of Example 3, 3.0 g of the title compound was obtained from 4.5 g of 4- [4- (4-chlorobenzyloxy) phenoxy] butanal. (50% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
_{l 3 -CD 3 OD (1:} 1)): 1.80-2.20 (2H, m), 2.25-
2.60 (2H, m), 3.94 (2H, t, J = 6Hz), 5.00 (2H, s), 6.87 (4H,
s), 7.03 (1H, t, J = 8 Hz), 7.37 (4H, s) 2) 5- [4- [4- (4-chlorobenzyloxy)
Phenoxy] butyl] thia Zorijin-2,4-dione (Compound No. 13-16) in the same manner as in 2) of Example 3, obtained in 1) 5- [4
From 3.0 g of-[4- (4-chlorobenzyloxy) phenoxy] butylidene] thiazolidine-2,4-dione, 2.5 g of the title compound was obtained (83% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ -CD ₃ OD): 1.45-2.30 (6H, m), 3.94 (2H, t, J = 6H
z), 4.35 (1H, dd, J = 4Hz, J = 9Hz), 5.00 (2H, s), 6.87 (4H,
s), 7.37 (4H, s) 3) 6- [4- (4-chlorobenzyloxy) phenoxy
Shi] -2-3 Merukaputohe hexanoic acid Example 3) and in the same manner, obtained in 2) 5- [4
-[4- (4-chlorobenzyloxy) phenoxy] butyl] thiazolidine-2,4-dione
1.40 g of the title compound were obtained as a slightly yellow solid (yield 60%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.45-2.20 (6H, m), 3.20-3.40 (1H, m), 3.92 (2H, m
t, J = 6Hz), 4.98 (2H, s), 6.85 (4H, s), 7.36 (4H, s) Example 34 2-mercapto-6- (2-naphthyloxy
B) Hexanoic acid (Exemplified Compound No. 6-23) 1) 5- [4- (2-Naphthyloxy) butylidene] thio
Azolidine-2,4 1 di one Example 3) and in the same manner, from 4- (2-naphthyloxy) butanal 5.1 g, the title compound 2.9g
Was obtained (yield 39%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.35-2.20 (4H, m), 4.07 (2H, t, J = 6Hz), 7.00-7.5
0 (5H, m), 7.55-7.90 (3H, m) 2) 5- [4- (2-naphthyloxy) butyl] thiazo
Lysine-2,4-dione (Exemplified Compound No. 14-23) 5- [4] obtained in 1) in the same manner as in Example 3-2)
-(2-naphthyloxy) butylidene] thiazolidine-
From 2.9 g of 2,4-dione, 1.6 g of the title compound was obtained (55% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.35-2.40 (6H, m), 4.07 (2H, t, J = 6Hz), 4.27 (1H,
dd, J = 4Hz, J = 9Hz), 7.00-7.50 (4H, m), 7.55-7.85 (3H, m) 3) 2-mercapto-6- (2-naphthyloxy) hex
Sannic acid 5- [4] obtained in 2) in the same manner as in 3) of Example 3
-(2-naphthyloxy) butyl] thiazolidine-2,
From 1.6 g of 4-dione, 1.2 g of the title compound was obtained as a white solid (yield 81%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.35-2.15 (6H, m), 2.14 (1H, d, J = 9Hz), 3.38 (1H,
dt, J = 7Hz, J = 9Hz), 4.07 (2H, t, J = 6Hz), 7.00-7.50 (4H,
m), 7.55-7.85 (3H, m) Example 35 8- (4-chlorophenoxy) -2-mer
Captooctanoic acid (Exemplified Compound No. 5-28) 1) 5- [6- (4-chlorophenoxy) hexylide
Thiazolidine-2,4 -dione The title compound 1.8 was obtained from 2.4 g of 6- (4-chlorophenoxy) hexanal in the same manner as 1) of Example 3).
g was obtained (yield 52%).

1 H-NMR (89.55 MHz, δ ppm, CDC
_{l 3): 1.40-2.00 (6H,} m), 2.05-2.10 (2H, m), 3.94 (2H,
t, J = 6Hz), 6.80 (2H, d, J = 9Hz), 7.06 (1H, t, J = 8Hz), 7.24
(2H, d, J = 9Hz) 2) 5- [6- (4-chlorophenoxy) hexyl] thio
Azolidine-2,4-one (Compound No. 13-2
8) 5- [6] obtained in 1) in the same manner as in 2) of Example 3.
-(4-chlorophenoxy) hexylidene] thiazolidine-2,4-dione from 1.7 g of the title compound 1.
45 g were obtained (85% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.25-2.45 (10H, m), 3.94 (2H, t, J = 6Hz), 4.43 (1
H, dd, J = 4Hz, J = 9Hz), 6.86 (2H, d, J = 9Hz), 7.24 (2H, d, J = 9
Hz) 3) 8- (4-chlorophenoxy) -2-mercapto
Kutanoic acid 5- [6] obtained in 2) in the same manner as in 3) of Example 3
-(4-chlorophenoxy) hexyl] thiazolidine-
From 1.45 g of 2,4-dione, 0.62 of the title compound was obtained.
g was obtained as a white solid (46% yield).

1H-NMR (89.55 MHz, δ ppm, CD ₃
OD): 1.25-2.00 (10H, m), 3.20-3.45 (1H, m), 3.93 (2
H, t, J = 6Hz), 6.86 (2H, d, J = 9Hz), 7.24 (2H, d, J = 9Hz) Example 36 8- (4 -Iodophenoxy ) -2-mel
Captooctanoic acid (Exemplified Compound No. 5-30) 1) 5- [6- (4-Iodophenoxy) hexylide
Thiazolidine-2,4 -dione The title compound was obtained from 5.25 g of 6- (4-iodophenoxy) hexanal in the same manner as 1) of Example 3).
55 g were obtained (yield 32%). 2) 5- [6- (4-iodophenoxy) hexyl] thio
Azolidine-2,4-one (Compound No. 13-3
0) 5- [6] obtained in 1) in the same manner as in 2) of Example 3.
-(4-Iodophenoxy) hexylidene] thiazolidine-2,4-dione from 2.55 g of the title compound
2.5 g were obtained as a colorless solid (75% yield). 3) 8- (4-iodophenoxy) -2-mercapto
Kutanoic acid 5- [6] obtained in 2) in the same manner as in 3) of Example 3
-(4-Iodophenoxy) hexyl] thiazolidine-
From 2.5 g of 2,4-dione, 1.9 g of the title compound was obtained as a colorless solid (yield 81%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.30-2.00 (10H, m), 2.14 (1H, d, J = 9Hz), 3.36 (1
H, dt, J = 9Hz, J = 7Hz), 3.90 (2H, t, J = 6Hz), 6.65 (2H, d, J = 9
Hz), 7.55 (2H, d, J = 9 Hz), 7.70 (1H, brs) Example 37 8- (4-Fluorophenoxy) -2-me
Lcaptooctanoic acid (Exemplified Compound No. 5-29) 1) 5- [6- (4-Fluorophenoxy) hexylide
Down] thiazolidine -2, 4-dione in the same manner as in Example 3 1) 6- (4-fluorophenoxy) hexanal 10.2g than, the title compound
5.23 g were obtained (36% yield). 2) 5- [6- (4-fluorophenoxy) hexyl]
Thiazolidine-2,4- dione (Exemplary Compound No. 13-
29) 5- [6) obtained in 1) in the same manner as in 2) of Example 3.
-(4-Fluorophenoxy) hexylidene] thiazolidine-2,4-dione From 5.23 g, the title compound
2.2 g were obtained (46% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.25-2.45 (10H, m), 3.90 (2H, t, J = 6Hz), 4.25 (1
H, dd, J = 4Hz, 9Hz), 6.65-7.10 (4H, m) 3) 8- (4-Fluorophenoxy) -2-mercapto
Octanoic acid 5- [6] obtained in 2) in the same manner as in 3) of Example 3.
-(4-Fluorophenoxy) hexyl] thiazolidine-2,4-dione from 2.2 g, 1.6 g of the title compound
Was obtained as a colorless solid (yield 79%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.25-2.00 (10H, m), 2.14 (1H, d, J = 9Hz), 3.36 (1
H, dt, J = 7Hz, J = 9Hz), 3.90 (2H, t, J = 6Hz), 6.65-7.10 (4
H, m), 8.00 (1H, brs) Example 38 2-mercapto-8- (1-naphthyloxy
B ) Octanoic acid (Exemplified Compound No. 6-31) 1) 5- [6- (1-Naphthyloxy) hexylidene]
Thiazolidine-2,4- dione The title compound 5.2 was obtained from 5.1 g of 6- (1-naphthyloxy) hexanal in the same manner as 1) of Example 3).
g was obtained (yield 72%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.50-2.40 (8H, m), 4.14 (2H, t, J = 6Hz), 6.80 (1H,
(dd, J = 3.6Hz), 7.08 (1H, t, J = 8Hz), 7.30-7.60 (4H, m), 7.
75-7.85 (1H, m), 8.20-8.35 (1H, m) 2) 5- [6- (1-naphthyloxy) hexyl] thia
Zorijin 2,4 Geo emissions (Compound No. 14-3
1) 5- [6) obtained in 1) in the same manner as in 2) of Example 3.
-(1-naphthyloxy) hexylidene) thiazolidine-
From 5.2 g of 2,4-dione, 4.0 g of the title compound was obtained (76% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.35-2.30 (10H, m), 4.13 (2H, t, J = 6Hz), 4.25 (1
H, dd, J = 4Hz, 9Hz), 6.80 (1H, dd, J = 3Hz, J = 6Hz), 7.30-7.6
0 (4H, m), 7.75-7.85 (1H, m), 8.20-8.35 (1H, m) 3) 2-Mercapto-8- (1-naphthyloxy ) oct
Tanic acid 5- [6] obtained in 2) in the same manner as in 3) of Example 3
-(1-naphthyloxy) hexyl] thiazolidine-
From 4.0 g of 2,4-dione, 1.9 g of the title compound
Was obtained (51% yield).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.25-2.10 (10H, m), 2.10 (1H, d, J = 9Hz), 3.35 (1H
H, dt, J = 7Hz, J = 9Hz), 4.11 (2H, t, J = 6Hz), 6.79 (1H, dd, J =
3Hz, 6Hz), 7.25-7.60 (4H, m), 7.70-7.85 (1H, m), 8.15-8.40
(1H, m) Example 39 2-mercapto-8- (4-phenylphene)
Noxy) octanoic acid (Exemplified Compound No. 5-31) 1) 5- [6- (4-phenylphenoxy) hexylide
Thiazolidine-2,4 -dione The title compound was obtained from 6.9 g of 6- (4-phenylphenoxy) hexanal in the same manner as 1) of Example 3).
7 g were obtained (37% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.45-2.00 (6H, m), 2.05-2.45 (2H, m), 4.00 (2H, m
t, J = 6Hz), 6.95 (2H, t, J = 6Hz), 7.06 (1H, t, J = 8Hz), 7.20
-7.65 (7H, m) 2) 5- [6- (4-phenylphenoxy) hexyl]
Thiazolidine-2,4- dione (Exemplary Compound No. 13-
31) 5- [6] obtained in 1) in the same manner as in 2) of Example 3.
-(4-phenylphenoxy) hexylidene] thiazolidine-2,4-dione from 3.5 g of the title compound
3.3 g were obtained (94% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.25-2.30 (10H, m), 3.97 (2H, t, J = 6Hz), 4.24 (1
H, dd, J = 4Hz, J = 9Hz), 6.95 (2H, d, J = 9Hz), 7.20-7.65 (7H,
m) 3) 2-mercapto-8- (4-phenylphenoxy)
Octanoic acid 5- [6] obtained in 2) in the same manner as in 3) of Example 3.
-(4-phenylphenoxy) hexyl] thiazolidine-2,4-dione from 3.3 g, 1.7 g of the title compound
Was obtained (55% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.25-2.10 (10H, m), 2.1 (1H, d, J = 9Hz), 3.35 (1H, m
dt, J = 7Hz, J = 9Hz), 3.97 (2H, t, J = 6Hz), 6.95 (2H, d, J = 9H
z), 7.15-7.65 (7H, m) Example 40 6- (4-chlorobenzyloxy) -2-
Mercaptohexanoic acid (Exemplary Compound No. 5-32) 1) 5- [4- (4-Chlorobenzyloxy) butylide
Thiazolidine-2,4 -dione The title compound was obtained from 7.0 g of 4- (4-chlorobenzyloxy) butanal in the same manner as 1) of Example 3).
0 g was obtained (yield 39%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.65-2.10 (2H, m), 2.20-2.53 (2H, m), 3.50 (2H, m
t, J = 6Hz), 4.45 (2H, s), 7.05 (2H, t, J = 7Hz), 7.15-7.40
(4H, m), 9.05 (1H, brs) 2) 5- [4- (4-chlorobenzyloxy) butyl]
Thiazolidine-2,4- dione (Exemplary Compound No. 13-
32) 5- [4] obtained in 1) in the same manner as in 2) of Example 3
-(4-chlorobenzyloxy) butylidene] thiazolidine-2,4-dione from 4.0 g of the title compound
2.1 g were obtained as a colorless oil (yield 52%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.30-2.25 (6H, m), 3.47 (2H, t, J = 6Hz), 4.24 (1H,
dd, J = 4Hz, J = 9Hz), 4.43 (2H, s), 7.15-7.45 (4H, m) 3) 6- (4-chlorobenzyloxy) -2-mercap
Toxanoic acid 5- [4] obtained in 2) in the same manner as in 3) of Example 3.
-(4-chlorobenzyloxy) butyl] thiazolidine-2,4-dione from 1.60 g.
8 g were obtained as a colorless oil (54% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
_{l 3): 1.40-2.25 (6H,} m), 2.12 (1H, d, J = 9Hz), 3.35 (1H,
dt, J = 9Hz, J = 7Hz), 3.46 (2H, t, J = 6Hz), 4.45 (2H, s), 7.1
5-7.40 (4H, m), 8.22 (1H, brs) Example 41 7- (benzyloxy) -2-mercapto
Heptanoic acid (Exemplified Compound No. 5-33) 1) 5- [5- (benzyloxy) pentylidene] thia
Zorijin 2,4 1 geo emissions Example 3) in analogy to 5- (benzyloxy)
From 4.0 g of pentanal, 3.5 g of the title compound was obtained (58% yield).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.35 (8H, m), 3.47 (2H, t, J = 6Hz), 4.24 (1H,
dd, J = 4Hz, J = 9Hz), 4.50 (2H, s), 7.15-7.40 (5H, m) 2) 5- [5- (benzyloxy) pentyl] thiazoli
Gin-2,4-dione (Exemplified Compound No. 13-33) 5- [5] obtained in 1) in the same manner as in 2) of Example 3
-(Benzyloxy) pentylidene] thiazolidine-
From 3.28 g of 2,4-dione, 1.9 g of the title compound
Was obtained (yield 58%). 3) 7- (benzyloxy) -2-mercaptoheptane
Acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
-(Benzyloxy) pentyl] thiazolidine-2,4
From 1.8 g of -dione, 1.0 g of the title compound was obtained (yield: 61%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.25 (8H, m), 2.12 (1H, d, J = 9Hz), 3.35 (1H,
dt, J = 7Hz, J = 9Hz), 3.46 (2H, t, J = 6Hz), 4.50 (2H, s), 6.0
0 (1H, brs), 7.15-7.40 (5H, m) Example 42 2-mercapto-7- (3-pyridyl)
Butanoic acid (Exemplified Compound No. 3-3) 1) 2-acetylthio-7- (3-pyridyl) heptane
Acid methyl ester ( Methyl ester of Exemplified Compound No. 3-18) A solution of 2.5 g of 7- (3-pyridyl) heptanoic acid, 3.1 ml of thionyl chloride and 4 drops of DMF was slowly heated to reflux until hydrochloric acid gas was not generated. . Further at room temperature, N
After 2.4 g of BS, 6 ml of carbon tetrachloride and 2 drops of concentrated HBr were added, and the mixture was refluxed slowly for 2 hours, the reaction solution was concentrated under reduced pressure, methanol was slowly added under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. The residue obtained by distilling off the solvent was neutralized with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and 2-bromo-7- (3-pyridyl) heptanoic acid methyl ester (3.6 g) and potassium thioacetate (1.44 g) in D were obtained.
After stirring a solution of 5 ml of MF at room temperature for 2 hours, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. After washing with aqueous sodium bicarbonate and water, it was dried over anhydrous sodium sulfate. The residue obtained by evaporating the solvent was subjected to column chromatography to give 1.76 g of the title compound as a colorless oil from a stream of 20% ethyl acetate / n-hexane (yield 49%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.00 (8H, m), 2.35 (3H, s), 2.62 (2H, t, J = 7H
z), 3.73 (3H, s), 4.19 (1H, t, J = 7Hz), 7.20 (1H, dd, J = 5Hz, J =
8 Hz), 7.50 (1H, dt, J = 2 Hz, J = 8 Hz), 8.45-8.50 (2H, m) 2) 2 -acetylthio obtained with 2 -mercapto-7- (3-pyridyl) heptanoic acid 1) 1.7 g of methyl 7- (3-pyridyl) heptanoate and NaOH
A solution of 0.7 g of 4 ml of methanol and 4 ml of water was refluxed for 2 hours under a nitrogen atmosphere. The solvent is distilled off and 10% H
After neutralization with Cl, the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was analyzed by column chromatography from a 2% methanol-chloroform stream to give 1.2 g of the title compound.
Was obtained (yield 87%).

1H-NMR (89.55 MHz, δ ppm, CDC
_{l 3): 1.25-2.10 (8H,} m), 2.65 (2H, t, J = 7Hz), 3.37 (1
H, t, J = 7Hz), 7.31 (1H, dd, J = 5Hz, J = 8Hz), 7.65 (1H, dt, J =
2Hz, J = 8Hz), 8.35-8.55 (2H, m), 9.72 (1H, brs) 13C-NMR (22.49MHz, δppm, CDCl 3): 27.
04, 28.44, 30.61, 32.73, 35.65, 41.61, 123.97, 13
7.89, 138.86, 144.88, 147.53, 176.47 Example 43 7- (4-benzyloxyphenyl) -2
-Mercaptoheptanoic acid ethyl ester ( Ethyl ester of Exemplified Compound No. 1-20) 1-g of 7- (4-benzyloxyphenyl) -2-mercaptoheptanoic acid is dissolved in 20 ml of ethanol, and 1 drop of concentrated sulfuric acid is added. The mixture was heated under reflux for 2 hours. The reaction solution was concentrated under reduced pressure, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give the title compound.
06 g was obtained as an oil (yield 98%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.2-2.1 (8H, m), 1.27 (3H, t, J = 7Hz), 2.02 (1H, d,
J = 9Hz), 2.54 (2H, t, J = 7Hz), 3.29 (1H, dt, J = 7Hz, J = 9Hz),
4.19 (2H, q, J = 7Hz), 5.03 (2H, s), 6.89 (2H, psd, J = 9Hz),
6.99 (2H, psd, J = 9 Hz), 7.2-7.5 (5H, m) Example 44 2-mercapto-7- [4- (4-thiazo
Rirumetokishi) phenyl-] heptanoic acid (Compound No. 1-57) 1) 5- [5- [4- (4-thiazolylmethoxy) Fe
Nyl] pentyl] thiazolidine-2,4-dione (Exemplary Compound No. 9-57) 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4-dione A solution of 2.0 g of 2.0 g of DMF in 100 ml of 60% NaH 5
After adding 73 mg and stirring at room temperature for 1 hour, 1.4 g of 4-bromomethylthiazole was added, and the mixture was stirred at 50 ° C for 1 hour. The reaction solution was poured into ice water, acidified with 10% aqueous HCl and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off. When the residue was subjected to column chromatography, 2.06 g of the title compound was obtained from a stream of 0.5% methanol / chloroform (yield: 76%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ -CD ₃ OD): 1.20-2.30 (8H, m), 2.57 (2H, t, J = 7H
z), 4.23 (1H, dd, J = 4,9Hz), 5.24 (2H, d, J = 1Hz), 6.90 (2
H, d, J = 9Hz), 7.11 (2H, d, J = 9Hz), 7.43 (1H, dd, J = 1,2Hz),
8.88 (1H, d, J = 2Hz) 2) 2-mercapto-7- [4- (4-thiazolylmetho
Carboxymethyl) In the same manner as phenyl] 3 hepta phosphate Example 3), obtained in 1) 5- [5
1.9 g of-[4- (4-thiazolylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione and NaO
12 g of 50% ethanol water of 2.0 g of H was heated to reflux for 2 hours in a nitrogen stream. Neutralized with concentrated HCl and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off. When the residue was subjected to column chromatography, 1.4 g of the title compound was obtained as a colorless solid from a stream of chloroform (yield 79).
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.15-2.05 (8H, m), 2.08 (1H, d, J = 9Hz), 2.54 (2H, m
t, J = 7Hz), 3.34 (1H, dt, J = 7,9Hz), 5.25 (2H, d, J = 1Hz),
6.88 (2H, d, J = 9Hz), 7.08 (2H, d, J = 9Hz), 7.40 (1H, dd, J =
1,2 Hz), 8.65 (1H, brs), 8.89 (1H, d, J = 2 Hz) 13C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
09, 28.55, 31.21, 34.84, 35.22, 40.85, 66.10, 114.
76, 116.00, 129.28, 135.29, 153.55, 156.48, 177.77 Example 45 2-mercapto-7- [4- (2-thienyl
Rumethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1
-50) 1) 5- [5- [4- (2-thienylmethoxy) phenyl)
Le] pentylidene] In the same manner as Chia Zorijin 2,4-dione Example 3 1), from 5- [4- (2-thienyl) phenyl] pentanal 4.0 g,
1.92 g of the title compound was obtained (36% yield). 1 H-NMR (89.55 MHz, δ ppm, CDCl ₃ ): 1.10
-1.85 (6H, m), 2.00-2.40 (2H, m), 2.40-2.70 (2H, m), 5.20 (2
H, s), 6.89 (2H, d, J = 9Hz), 7.10 (2H, d, J = 9Hz), 6.90-7.15 (2
H, m), 7.32 (1H, dd, J = 1,5Hz) 2) 5- [5- [4- (2 -thienylmethoxy) phene
Nyl] pentyl] thiazolidine-2,4-dione (Exemplary Compound No. 9-50) The 5- [5] obtained in 1) in the same manner as in 2) of Example 3
From 1.74 g of-[4- (2-thienylmethoxy) phenyl] pentylidene] thiazolidine-2,4-dione, 1.12 g of the title compound was obtained (yield: 64).
%).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.20-2.30 (8H, m), 2.55 (2H, t, J = 7Hz), 4.26 (1H,
(dd, J = 4,9Hz), 5.20 (2H, d, J = 1Hz), 6.89 (2H, d, J = 9Hz), 6.90
-7.15 (2H, m), 7.10 (2H, d, J = 9Hz), 7.32 (1H, dd, J = 1,5Hz),
8.50 (1H, brs) 3) 2-mercapto-7- [4- (2-thienylmethoxy)
C) Phenyl] heptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
-[4- (2-thienylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione from 1.73 g,
1.3 g of the title compound was obtained as a colorless solid (yield 80.5%).

1 H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.20-2.05 (8H, m), 2.08 (1H, d, J = 9 Hz), 2.54 (2
H, t, J = 7Hz), 3.34 (1H, dt, J = 7,9Hz), 5.18 (2H, d, J = 1Hz),
6.80-7.15 (2H, m), 6.88 (2H, d, J = 9Hz), 7.08 (2H, d, J = 9H
z), 7.30 (1H, dd , J = 1,5Hz), 8.15 (1H, brs) 13C-NMR (22.49MHz, δppm, CDCl 3): 27.
04, 28.55, 31.26, 34.84, 35.06, 40.74, 65.18, 114.
92, 126.03, 126.62, 126.73, 129.28, 135.24, 139.57,
156.48, 179.07 Example 46 2-mercapto-7- [4- (2-pyridyl
Rumethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1
-44) 1) 5- [5- [4- (2-pyridylmethoxy) phenyl]
Le] pentyl] thiazol Jin-2,4-dione (Compound No. 9-44) In the same manner as 1) of Example 44, 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4 By reacting 2.3 g of dione with 1.3 g of 2-picolyl chloride hydrochloride, 1.29 g of the title compound was obtained as a yellow solid (yield 43%).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.18-1.76 (6H, m), 1.76-2.28 (2H, m), 2.54 (2
H, t, J = 7Hz), 4.23 (1H, dd, J = 4Hz, J = 8Hz), 5.22 (2H, s),
6.90 (2H, psd, J = 9Hz), 7.0-7.35 (2H, m), 7.56 (1H, psd, J =
8Hz), 7.66 (1H, m), 8.60 (1H, m) 2) 2-Mercapto-7- [4- (2-pyridylmethoxy)
C) Phenyl] heptanoic acid 5- [5] obtained in 1) in the same manner as in 3) of Example 3
From 0.7 g of-[4- (2-pyridylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione, 0.97 g of the title compound was obtained as a colorless solid (yield: 8).
8%).

1H-NMR (89.55 MHz, δ ppm, CD3
OD): 1.18-1.96 (8H, m), 2.55 (2H, t, J = 7Hz), 3.37 (1
H, t, J = 7Hz), 5.13 (2H, s), 6.91 (2H, psd, J = 9Hz), 7.10 (2H
H, psd, J = 9Hz), 7.36 (1H, m), 7.57 (1H, psd, J = 8Hz), 7.86
(1H, m), 8.52 (1H, m) Example 47 2-mercapto-7- [4- (3-pyridyl
Rumethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1
-45) 1) 5- [5- [4- (3-pyridylmethoxy) phenyl]
Le] pentyl] thiazol Jin-2,4-dione (Compound No. 9-45) In the same manner as 1) of Example 44, 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4 From 2.5 g of dione and 1.7 g of 3-picolyl chloride hydrochloride, 1.71 g of the title compound was obtained as a colorless solid (yield: 52%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.18-1.76 (6H, m), 1.76-2.28 (2H, m), 2.55 (2H, m
t, J = 7Hz), 4.23 (1H, dd, J = 4Hz, J = 8Hz), 5.06 (2H, s), 6.8
9 (2H, psd, J = 9Hz), 7.07 (2H, psd, J = 9Hz), 7.40 (1H, dd, J =
5Hz, J = 8Hz), 7.81 (1H, dt, J = 8Hz, J = 2Hz), 8.59 (1H, dd, J =
2Hz, J = 5Hz), 8.70 (1H, d, J = 2Hz) 2) 2-mercapto-7- [4- (3-pyridylmethoxy)
C) Phenyl] heptanoic acid 5- [5] obtained in 1) in the same manner as in 3) of Example 3
From 1.6 g of-[4- (3-pyridylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione, 1.1 g of the title compound was obtained as a colorless solid (yield: 8).
0%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.15-2.20 (8H, m), 2.55 (2H, t, J = 7Hz), 3.36 (1H,
t, J = 7Hz), 5.07 (2H, s), 6.89 (2H, psd, J = 9Hz), 7.07 (2H, s
psd, J = 9Hz), 7.40 (1H, dd, J = 5Hz, J = 8Hz), 7.87 (1H, dt, J =
8Hz, J = 2Hz), 8.59 (1H, dd, J = 2Hz, J = 5Hz), 8.70 (1H, d, J = 2
Hz) Example 48 2-mercapto-7- [4- (4-pyridyl)
Rumethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1
-46) 1) 5- [5- [4- (4-pyridylmethoxy) phenyl)
Le] pentyl] thiazol Jin-2,4-dione (Compound No. 9-46) In the same manner as 1) of Example 44, 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4 By reacting 1.8 g of dione with 1.2 g of 4-picolyl chloride hydrochloride, 1.31 g of the title compound was obtained as a colorless solid (yield: 52%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.23-1.78 (6H, m), 1.78-2.28 (2H, m), 2.55 (2H, m
t, J = 7Hz), 4.22 (1H, dd, J = 4Hz, J = 8Hz), 5.10 (2H, s), 6.8
7 (2H, psd, J = 9Hz), 7.08 (2, psd, J = 9Hz), 7.43 (2H, psd, J =
6Hz), 8.56 (2H, psd, J = 6Hz) 2) 2-mercapto-7- [4- (4-pyridylmethodine)
C) Phenyl] heptanoic acid 5- [5] obtained in 1) in the same manner as in 3) of Example 3
From 1.2 g of-[4- (4-pyridylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione, 0.9 g of the title compound was obtained as a colorless solid (yield: 8).
0%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.18-2.16 (8H, m), 2.55 (2H, t, J = 7Hz), 3.36 (1H, m
t, J = 7Hz), 5.09 (2H, s), 6.86 (2H, psd, J = 9Hz), 7.04 (2, p
sd, J = 9 Hz), 7.44 (2H, psd, J = 6 Hz), 8.63 (2H, psd, J = 6 Hz) Example 49 2-mercapto-7- [4- (2-pyridyl)
Ruethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1
-70) 1) 5- [5- [4- (2-pyridylethoxy) pheni
Le] pentylidene] 1-thia Zorijin 2,4-dione Example 3) in analogy to 5- [4- (from 2-pyridyl) phenyl] pentanal 5.0 g, the title compound 2.6g as a yellow solid Obtained (yield 3
9%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.41-1.87 (4H, m), 2.23 (2H, m), 2.55 (2H, t, J = 7H
z), 3.29 (2H, t, J = 7Hz), 4.33 (2H, t, J = 7Hz), 6.83 (2H, ps
d, J = 9Hz), 6.85-7.38 (5H, m), 7.62 (1H, m), 8.57 (1H, m) 2) 5- [5- [4- (2-pyridylethoxy) pheni
Le] pentyl] thiazol Jin-2,4-dione (Compound No. 9-70) In the same manner as in 2) of Example 3, obtained in 1) 5- [5
-[4- (2-pyridylethoxy) phenyl] pentylidene] thiazolidine-2,4-dione
2.2 g of the title compound were obtained as a colorless oil (yield: 8).
8%).

1H-NMR (89.55 MHz, δ ppm, CDC
_{l 3 -CD 3 OD): 1.18-1.74} (6H, m), 1.74-2.23 (2H,
m), 2.53 (2H, t, J = 7), 3.28 (2H, t, J = 7), 4.29 (3H, m), 6.
79 (2H, psd, J = 9), 7.02 (2H, psd, J = 9), 7.11-7.35 (2H, m),
7.66 (1H, m), 8.59 (1H, m) 3) 2-mercapto-7- [4- (2-pyridyleth
) Phenyl] 3 hepta phosphate Example 3) and in the same manner, obtained in 2) 5- [5
From 2.0 g of-[4- (2-pyridylethoxy) phenyl] pentyl] thiazolidine-2,4-dione, 1.4 g of the title compound was obtained as a colorless oil (yield 75%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.18-2.16 (8H, m), 2.50 (2H, t, J = 7Hz), 3.30 (3H,
m), 4.29 (2H, t, J = 7Hz), 6.79 (2H, psd, J = 9Hz), 7.02 (2H,
psd, J = 9Hz), 7.11-7.42 (2H, m), 7.71 (1H, m), 8.62 (1H,
m) Example 50 2-mercapto-7- [4- (2-thienyl
Ruethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1
-52) 1) 5- [5- [4- (2-thienylethoxy) phenyl)
Le] pentylidene] thiazoline-2,4-dione Example 3 1) and in the same manner, from 5- [4- (2-thienyl) phenyl] pentanal 4.7 g,
3.7 g of the title compound were obtained as a yellow solid (yield 58%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.30-1.75 (4H, m), 2.02-2.40 (2H, m), 2.40-2.80
(2H, m), 3.29 (2H, t, J = 7Hz), 4.16 (2H, t, J = 7Hz), 6.7-7.
31 (8H, m) 2) 5- [5- [4- (2-thienylethoxy) phenyl
Le] pentyl] thiazol down-2,4-dione (Compound No. 9-52) In the same manner as in 2) of Example 3, obtained in 1) 5- [5
From 2.5 g of-[4- (2-thienylethoxy) phenyl] pentylidene] thiazoline-2,4-dione, 1.8 g of the title compound was obtained as a slightly yellow syrup (yield: 72%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-1.70 (6H, m), 1.75-2.28 (2H, m), 2.54 (2H, m
(t, J = 7Hz), 3.29 (2H, t, J = 7Hz), 4.17 (3H, m), 6.70-7.21
(7H, m) 3) 2-mercapto-7- [4- (2-thienylethoxy)
C) Phenyl] heptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
From 1.4 g of-[4- (2-thienylethoxy) phenyl] pentyl] thiazoline-2,4-dione, 1.0 g of the title compound was obtained as a slightly yellow syrup (yield 77%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.18-2.05 (8H, m), 2.07 (1H, d, J = 9Hz), 2.54 (2H, m
t, J = 7Hz), 3.37 (3H, m), 4.17 (2H, t, J = 7Hz), 6.75-7.28
(7H, m) Example 51 2-mercapto-7- [4- (1-pheno
[Xyethyl) phenyl] heptanoic acid (Exemplary Compound No. 1
-31) 1) 5- [5- [4- (1-phenoxyethyl) phenyi
Le] pentylidene] thiazoline-2,4-dione Example 3 1) and in the same manner, from 5- [4- (1-phenoxyethyl) phenyl] pentanal 2.71 g, the title compound 2.82g was obtained (Yield 77
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.30 (6H, m), 1.60 (3H, d, J = 7Hz), 2.57 (2H, m
t, J = 7Hz), 5.28 (1H, q, J = 7Hz), 5.28 (1H, q, J = 7Hz), 6.70
-7.40 (10H, m) 2) 5- [5- [4- (1-phenoxyethyl ) phenyi
Le] pentylidene] thiazoline-2,4-dione (Compound No. 9-31) In the same manner as in 2) of Example 3, obtained in 2) 5- [5
-[4- (1-phenoxyethyl) phenyl] pentylidene] thiazoline-2,4-dione From 2.82 g,
1.82 g of the title compound were obtained (64% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.30 (8H, m), 1.60 (3H, d, J = 7Hz), 2.57 (2H, m
t, J = 7Hz), 4.23 (1H, dd, J = 4Hz, J = 9Hz), 5.28 (1H, q, J = 7H
z), 6.70-7.00 (3H, m), 700-7.40 (6H, m) 3) 2-mercapto-7- [4- (1-phenoxyethyl
L) phenyl] heptanoic acid In the same manner as in 3) of Example 3, 5- [5] obtained in 2)
From 1.5 g of-[4- (1-phenoxyethyl) phenyl] pentyl] thiazoline-2,4-dione, 1.0 g of the title compound was obtained as a colorless solid (yield: 59).
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.05 (8H, m), 1.61 (3H, d, J = 7Hz), 2.07 (1H,
d, J = 9Hz), 2.57 (2H, t, J = 7Hz), 3.34 (1H, dt, J = 7Hz, J = 9H
z), 5.28 (1H, q, J = 7Hz), 6.70-7.00 (3H, m), 7.00-7.40 (6
H, m) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 24.3
3, 27.04, 28.66, 30.99, 35.06, 35.43, 40.69, 75.8
0, 115.95, 120.55, 125 Example 52 2-mercapto-7- (2-quinolyl)
Butanoic acid (Exemplified Compound No. 4-3) 1) 2-acetylthio-7- (2-quinolyl) heptane
Acid methyl ester ( methyl ester of Exemplified Compound No. 4-19) 7- (2-quinolyl) in the same manner as in Example 42-1)
From 3.59 g of heptanoic acid, 1.5 g of the title compound was obtained as a colorless oil (yield: 32%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.30-2.05 (8H, m), 2.34 (3H, s), 2.97 (2H, t,
J = 8Hz), 3.71 (3H, s), 4.19 (1H, t, J = 7Hz), 7.27 (1H,
d, J = 8Hz), 7.35-7.85 (3H, m), 8.03 (1H, d, J = 8Hz),
8.06 (1H, d, J = 8 Hz) 2) 2-Mercapto-7- (2-quinolyl) heptanoic acid In the same manner as in Example 42-2), 2-acetylthio-7- (2) obtained in 1) was obtained. From 0.9 g of -quinolyl) heptanoic acid methyl ester, 0.96 g of the title compound was obtained as a slightly yellow oil (yield: 76%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.30-2.15 (8H, m), 3.06 (2H, t, J = 8Hz), 3.42
(1H, t, J = 7Hz), 7.35 (1H, d, J = 8Hz), 7.40-7.90 (3H,
m), 8.18 (1H, d, J = 8Hz), 8.28 (1H, d, J = 8Hz), 9.05 (1
H, brs) 13 C-NMR (22.49 MHz, CDCl ₃ ): 27.09, 28.93,
29.96, 35.87, 37.49, 41.77, 121.69, 126.40, 126.84,
127.49, 130.41, 138.11, 145.91, 162.60, 176.35 Example 53 2-mercapto-7- [4- (3-thienyl
Rumethoxy) phenyl] heptanoic acid (Compound Reference No. 1
-51) 1) 5- [5- [4- (3-thienylmethoxy) phenyl]
L] pentyl] thiazolidine-2,4-dione (Compound Reference No. 9-51) In the same manner as in Example 44-1), 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4-dione 2.0 g and 3-chloromethylthiophene 1.05
By reacting g, 1.57 g of the title compound was obtained as a slightly yellow solid (yield 58%).

1H-NMR (89.55 MHz, δ ppm, CDC
_{l 3 -CD 3 OD): 1.20-2.30} (8H, m), 2.55 (2H, t, J = 7H
z), 4.26 (1H, dd, J = 4Hz, 9Hz), 5.04 (2H, s), 6.89 (2H, d, J
= 9Hz), 7.10 (2H, d, J = 9Hz), 7.05-7.40 (3H, m), 8.50 (1H,
brs) 2) 2-mercapto-7- [4- (3-thienylmethoxy)
C) Phenyl] heptanoic acid 5- [5] obtained in 1) in the same manner as in 3) of Example 3
-[4- (3-thienylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione from 1.57 g,
1.05 g of the title compound was obtained as a colorless solid (yield 77%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.05 (8H, m), 2.08 (1H, d, J = 9Hz), 2.55 (2H,
t, J = 7Hz), 3.34 (1H, dt, J = 7Hz, 9Hz), 5.04 (2H, s), 6.87
(2H, d, J = 9Hz), 7.08 (2H, d, J = 9Hz), 7.10-7.40 (3H, m),
7.80 (1H, brs) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.0
4, 28.55, 31.26, 34.84, 35.06, 40.74, 65.78, 114.7
0, 122.93, 126.13,127.00, 129.22, 134.96, 138.21,
156.80, 178.95 Example 54 7- (4-Benzyloxymethylphenyi)
) -2-mercaptoheptanoic acid (Compound Reference No. 1-
32) 1) 5- [5- (4-benzyloxymethylphenyl)
Pentylidene] thiazol Jin-2,4-dione Example 3 1) and in the same manner, from 4-benzyloxy-methylphenyl pentanal 3.36 g, the title compound 1.88g was obtained (41% yield). 2) 5- [5- (4-benzyloxymethylphenyl)
Pentyl] thiazolidine -2,4-dione (Compound Reference No. 9-32) The 5- [5] obtained in 2) in the same manner as in 2) of Example 3
-(4-benzyloxymethylphenyl) pentylidene] thiazolidine-2,4-dione from 1.85 g,
1.34 g of the title compound were obtained (yield 72%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.15-2.25 (8H, m), 2.61 (2H, t, J = 7Hz), 4.22 (1H, m
dd, J = 9Hz, 5Hz), 4.51 (2H, s), 4.56 (2H, s), 7.14 (2H, d, J
= 9Hz), 7.31 (2H, d, J = 9Hz), 7.34 (5H, s) 3) 7- (4-benzyloxymethylphenyl) -2-
Mercaptoheptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
From (1.32 g of-(4-benzyloxymethylphenyl) pentyl] thiazolidine-2,4-dione, 0.92 g of the title compound was obtained (yield: 75%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.05 (8H, m), 2.09 (1H, d, J = 9Hz), 2.60 (2H, m
t, J = 8Hz), 3.32H, dt, J = 9Hz, J = 7Hz), 4.52 (2H, s), 4.55
(2H, s), 7.13 (2H, d, J = 8Hz), 7.28 (2H, d, J = 8Hz), 7.33 (5
H, s) Example 55 7- [4- (2-furylmethoxy) phenyl
2-mercaptoheptanoic acid (Compound Reference No. 1-
54) 1) 5- [5- [4- (2-furylmethoxy) phenyl)
Le] pentylidene] thiazole-2,4-dione 1) In the same manner as in 1) of Example 3, 2- (from furanyl methoxyphenyl) pentanal 3.7 g, the title compound 1.74g was obtained (yield Rate 34%). 2) 5- [5- [4- (2-furylmethoxy) phenyl)
Le] pentyl] thiazolidine down-2,4-dione (Compound Docket No. 9-54) In the same manner as in 2) of Example 3, 1) obtained in 5- [5
0.8 g of the title compound was obtained from 1.72 g of-(2-furanylmethoxyphenyl) pentylidene] thiazolidine-2,4-dione (46% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-1.88 (6H, m), 1.88-2.35 (2H, m), 2.56 (2H, m
t, J = 7Hz), 4.28 (1H, dd, J = 8Hz, 5Hz), 4.99 (2H, s), 6.40
(1H, m), 6.89 (2H, d, J = 9Hz), 7.10 (2H, d, J = 9Hz), 7.45 (1
H, m) 3) 7- [4- (2-furanylmethoxy) phenyl]-
2-mercaptoheptanoic acid In the same manner as in 3) of Example 3, 5- [5] obtained in 2)
-[4- (2-furanylmethoxy) phenyl] pentyl] -2,4-thiazolidinedione from 1.78 g,
0.5 g of the title compound was obtained (73% yield).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.15-2.10 (8H, m), 2.08 (1H, d, J = 9Hz), 2.56 (2H, m
t, J = 7Hz), 3.33 (1H, dt, J = 9Hz, J = 7Hz), 4.97 (2H, s), 6.4
0 (2H, m), 6.89 (2H, d, J = 9Hz), 7.10 (2H, d, J = 9Hz), 7.45
(1H, m) Example 56 7- [4- (2-phenethyl) phenyl]
-2-mercaptoheptanoic acid (Compound Reference No. 1-3
3) 1) 5- [5- [4- (2-phenethyl) phenyl] pe
Nchiriden] In the same manner as thiazolidine down-2,4-dione Example 3 1), 5- [4- (2-phenethyl) phenyl] pentanal 2.7g than title compound 2.51g was obtained (yield: 68%). 2) 5- [5- [4- (2-phenethyl) phenyl] pe
[Nthyl] thiazolidine- 2,4-dione (Compound Reference No. 9-33) 5- [5] obtained in 1) in the same manner as in 2) of Example 3.
-[4- (2-phenethyl) phenyl] pentylidene]
1.46 g of the title compound was obtained from 2.4 g of thiazolidine-2,4-dione (yield: 61%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.35 (8H, m), 2.58 (2H, t, J = 7Hz), 2.89 (4H,
s), 4.24 (1H, dd, J = 9Hz, J = 5Hz), 7.00-7.32 (9H, m) 3) 7- [4- (2-phenethyl) phenyl] -2-me
Rucaptoheptanoic acid In the same manner as in 3) of Example 3, 5- [5-
The title compound was obtained from [4- (2-phenethyl) phenyl] pentyl] thiazolidine-2,4-dione.

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.15-2.02 (8H, m), 2.08 (1H, d, J = 9Hz), 2.58 (2H, m
t, J = 8Hz), 2.89 (4H, s), 3.32 (1H, dt, J = 9Hz, J = 7Hz), 7.0
4-7.35 (9H, m) 13C- NMR (22.49MHz, δppm, CDCl 3): 27.
0, 28.6, 31.1, 35.0, 35.3, 37.5, 37.9, 40.7, 125.
8, 128.3, 139.1, 139.9, 141.9, 179.3 Example 57 7- [4- (1-Hydroxy-2- phenene)
Tyl) phenyl] -2-mercaptoheptanoic acid (Exemplary Compound No. 1-34) 1) 5- [5- [4- [1- (t-butyldimethylsilyl)
L) oxy-2-phenethyl] phenyl] pentyl] thia
Zolidine-2,4-dione 5- [4- [1- (t-butyldimethylsilyl) oxy-
From 6.0 g of 2-phenethyl] phenyl] pentanal, 5- [5- [4- [1] was obtained in the same manner as 1) of Example 3.
-(T-butyldimethylsilyl) oxy-2-phenethyl] phenyl] pentylidene] thiazolidine-2,4-
6.31 g of dione was obtained (84% yield). From 5.83 g of this compound, 4.8 g of the title compound was obtained in the same manner as in 2) of Example 3 (yield: 82%). 2) 5- [5- [4- (1-hydroxy-2-phenene)
Tyl) phenyl] pentyl] thiazolidine-2,4-di
ON (Exemplified Compound No. 9-34) 1M tetrabutylammonium fluoride (TBAF) THF solution was added to 2.5 g of the compound obtained in the above 1) for 20 g.
ml was added and stirred at room temperature for 24 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, the residue was subjected to column chromatography, and the residue was eluted with hexane-ethyl acetate (5: 1). 1.52 g of the title compound was obtained (yield 79%).

1H-NMR (89.55 MHz, δ ppm, CDC
_{l 3): 1.20-2.35 (8H,} m), 2.61 (2H, t, J = 7Hz), 3.01 (2H
d, J = 7Hz), 4.22 (1H, dd, J = 9Hz, J = 5Hz), 4.88 (1H, t, J = 7H
z), 7.08-7.36 (9H, m) 3) 7- [4- (1-hydroxy-2-phenethyl) phenyl
5- [5- [4- (1-Hydroxy-2) obtained by phenyl] -2-mercaptoheptanoic acid 2).
-Phenethyl) phenyl] pentyl] thiazolidine-
0.85 g of the title compound was obtained from 1.2 g of 2,4-dione in the same manner as in 3) of Example 3 (yield: 76%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.00 (8H, m), 2.07 (1H, d, J = 9Hz), 2.60 (2H, m
t, J = 8Hz), 3.02 (2H, d, J = 7Hz), 3.30 (1H, dt, J = 9Hz, J = 7H
z), 4.86 (1H, t, J = 7 Hz), 5.15 (2H, bs), 7.08-7.40 (9H, m) Example 58 7- (4-phenylacetylphenyl)-
2-mercaptoheptanoic acid (Compound Reference No. 1-35) 1) 5- [5- (4-phenylacetylphenyl) pen
[Tyl] thiazolidine-2,4-dione (Exemplified Compound No. 9-35) 5- [5- [4- (1-hydroxy-2-phenethyl) phenyl] pentyl] thiazolidine obtained in Example 57-2) 0.8 g of 2,4-dione in methylene chloride
The resultant was dissolved in 10 ml, 0.6 g of PCC was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was filtered through celite, the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography to obtain 0.49 g of the title compound from a portion eluted with hexane-ethyl acetate (5: 1). (Yield 62
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.35 (8H, m), 2.67 (2H, t, J = 8Hz), 4.24 (1H,
(dd, J = 9Hz, J = 5Hz), 4.28 (2H, s), 7.23 (2H, d, J = 9Hz), 7.29
(5H, s), 7.95 (2H, d, J = 9Hz) 2) 7- (4-phenylacetylphenyl) -2-merca
Peptoheptanoic acid 5- [5- (4-phenylacetylphenyl) pentyl] thiazolidine-2,4-dione obtained in 1) above
From 0.46 g, 0.28 g of the title compound was obtained in the same manner as in 3) of Example 3 (yield: 65%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.00 (8H, m), 2.08 (1H, d, J = 9Hz), 2.65 (2H, m
t, J = 8Hz), 3.30 (1H, dt, J = 9Hz, J = 7Hz), 4.26 (2H, s), 7.2
3 (2H, d, J = 9 Hz), 7.29 (5H, s), 7.93 (2H, d, J = 9 Hz) Example 59 7- [4- (3,5-dimethyl-4-iso)
Oxazolylmethoxy) phenyl] -2-mercaptohe
Heptanoic acid (Compound No. 1-69) 1) 5- [5- [4- (3,5-dimethyl-4-Isoo
Xazolylmethoxy) phenyl] pentyl] thiazolidi
Down-2,4-dione (Compound No. 9-69) In the same manner as 1) of Example 44 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4-dione 2.0g and 4 By reacting 1.15 g of -chloromethyl-3,5-dimethylisoxazole.
2.46 g of the title compound were obtained as a slightly yellow oil (88% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.30 (8H, m), 2.28 (3H, s), 2.39 (3H, s), 2.
57 (2H, t, J = 7Hz), 4.26 (1H, dd, J = 5Hz, 8Hz), 4.76 (2H, s),
6.85 (2H, d, J = 9Hz), 7.10 (2H, d, J = 9Hz), 8.55 (1H, brs) 2) 7- [4- (3,5-dimethyl-4-isoxazo
Rylmethoxy) phenyl ] -2-mercaptoheptanoic acid 5- [5-
From 2.32 g of [4- (3,5-dimethyl-4-isoxazolylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione, 0.92 g of the title compound was obtained as a colorless oil (yield). 42%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.05 (8H, m), 2.08 (1H, d, J = 9Hz), 2.28 (3H,
s), 2.39 (3H, s), 2.57 (2H, t, J = 7Hz), 3.34 (1H, dt, J = 7H
z, 9Hz), 4.76 (2H, s), 6.85 (2H, d, J = 9Hz), 7.10 (2H, d, J =
9Hz), 7.65 (1H, brs) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 10.0
8, 11.11, 27.04, 28.55, 31.26, 34.84, 35.11, 40.7
4, 59.65, 110.47, 114.86, 129.38, 135.56, 156.41,
159.78, 167.42, 178.20 Example 60 2-mercapto-7- [4- (2-thiazo
Rylmethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1-87) 1) 5- [5- [4- (2-thiazolylmethoxy ) phenyl
Sulfonyl] pentyl] thiazole-2,4-dione (Compound No. 9-99) In the same manner as 1) of Example 44, 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4 From 2-g of dione and 1.1 g of 2-thiazolylmethylmethanesulfonate, 5- [5- [4- (2-thiazolylmethoxy) phenyl] pentyl] thiazolidine-2,4-
1.4 g of dione were obtained as a yellow solid (yield 65
%).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.23-1.78 (6H, m), 1.78-2.28 (2H, m), 2.55 (2
H, t, J = 7Hz), 4.25 (1H, dd, J = 5Hz, J = 8Hz), 5.37 (2H, s),
6.90 (2H, d, J = 9Hz), 7.08 (2H, d, J = 9Hz), 7.36 (1H, d, J = 3H
z), 7.80 (1H, d, J = 3 Hz) 2) 2-mercapto-7- [4- (2-thiazolylmetho
Carboxymethyl) In the same manner as phenyl] 3 hepta phosphate Example 3), obtained in 1) 5- [5
-[4- (2-thiazolylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione
0.89 g of mercapto-7- [4- (2-thiazolylmethoxy) phenyl] heptanoic acid was obtained as a yellow solid (yield 73%).

1H-NMR (89.55 MHz, δ ppm, CDC
l_Three): 1.23-1.98 (8H, m), 2.09 (1H, d, J = 9Hz), 2.55 (2H, m
t, J = 7Hz), 3.38 (1H, dt, J = 7Hz, J = 9Hz), 5.37 (2H, s), 6.9
0 (2H, d, J = 9Hz), 7.08 (2H, d, J = 9Hz), 7.36 (1H, d, J = 3Hz),
7.80 (1H, d, J = 3 Hz) 13 C-NMR (22.49 MHz, δ ppm, CDCl_Three): 27.
20, 28.64, 31.31, 34.91, 35.31, 40.99, 67.20, 114.
69, 119.71, 129.23, 135.66, 141.86, 155.67, 167.89,
 177.47 Example 612-mercapto-7- [4- (3-methoxy
Cibenzyloxy) phenyl] heptanoic acid (Illustrative compounds
No. 1-90) 1)5- [5- [4- (3-methoxybenzyloxy)
Phenyl] pentyl] h Azolidine-2,4-dione
(Exemplified Compound No. 9-22) In the same manner as in Example 44-1), 5- [5- (4-hydrido)
Roxyphenyl) pentyl] thiazolidine-2,4-di
1.5 g of ON and 3-methoxybenzyl mesylate
By reacting 1.28 g, 5- [5- [4-
(3-methoxybenzyloxy) phenyl] pentyl]
1.54 g of thiazolidine-2,4-dione was a slightly yellow solid
It was obtained as a product (yield 72%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.30 (8H, m), 2.55 (2H, t, J = 7Hz), 3.81
(3H, s), 4.26 (1H, dd, J = 4Hz, J = 9Hz), 5.00 (3H, s),
6.85 (2H, d, J = 9Hz), 7.10 (2H, d, J = 9Hz), 6.80-7.40
(4H, m), 8.60 (1H, brs) 2) 2-mercapto-7- [4- (3-methoxybenzyl )
Yloxy) In the same manner as phenyl] 3 of heptane acid Example 3), obtained in 1) 5- [5
0.84 g of 2-mercapto-7- [4- (3-methoxybenzyloxy) phenyl] heptanoic acid was obtained from 1.54 g of-[4- (3-methoxybenzyloxy) phenyl] pentyl] thiazolidine-2,4-dione. Obtained as a colorless oil (58% yield).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.20-2.05 (8H, m), 2.08 (1H, d, J = 9Hz), 2.5
4 (2H, t, J = 7Hz), 3.34 (1H, dt, J = 7Hz, J = 9Hz), 3.81
(3H, s), 5.00 (2H, s), 6.85 (2H, d, J = 9Hz), 7.10 (2H,
d, J = 9 Hz), 6.80-7.40 (4H, m) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.0
4, 28.55, 31.26, 34.84, 35.06, 40.69, 55.21, 70.0
0, 112.86, 113.46, 114.76, 119.63, 129.22, 129.55,
134.86, 138.86, 156.91, 159.83, 178.80 Example 62 6- (6-Benzyloxy-2-naphthyl
Oxy) -2-mercaptohexanoic acid (Exemplary Compound No. 6-13) 1) 5- [4- (6-benzyloxy-2-naphthylthio)
Carboxymethyl) butylidene] In the same manner as Chia Zorijin 2,4-dione Example 3 1), 4- (6-benzyloxy-2-naphthyloxy) flatweed - 5 from Le 2.0g
-[4- (6-benzyloxy-2-naphthyloxy)
[Butylidene] thiazolidine-2,4-dione 1.01
g was obtained (yield 39%). 1H-NMR (89.55 MHz, δ ppm, CDCl ₃ ): 1.50-
2.25 (4H, m), 4.10 (2H, t, J = 6Hz), 5.16 (2H, s), 6.90-7.7
5 (12H, m) 2) 5- [4- (6-benzyloxy-2-naphthylthio)
Carboxymethyl) butyl] thiazol Jin-2,4-dione (Compound No. 14-13) in the same manner as in 2) of Example 3, obtained in 1) 5- [4
-(6-benzyloxy-2-naphthyloxy) butylidene] thiazolidine-2,4-dione From 1.01 g, 5- [4- (6-benzyloxy-2-naphthyloxy) butyl] thiazolidine-2,4- Zeon 0.8
g was obtained as a colorless solid (79% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.50-2.30 (6H, m), 4.10 (2H, t, J = 6Hz), 4.25 (1H,
dd, J = 4Hz, J = 9Hz), 5.16 (2H, s), 7.05-7.75 (11H, m) 3) 6- (6-benzyloxy-2-naphthyloxy)
In the same manner as 2-3-mercapto hexane acid Example 3), obtained in 2) 5- [4
-(6-benzyloxy-2-naphthyloxy) butyl] thiazolidine-2,4-dione
0.22 g of (6-benzyloxy-2-naphthyloxy) -2-mercaptohexanoic acid was obtained as a colorless solid (33% yield).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.30-2.00 (6H, m), 2.14 (1H, d, J = 9Hz), 3.38 (1
H, dt, J = 7Hz, J = 9Hz), 4.10 (2H, t, J = 6Hz), 5.16 (2H, s), 6.
90-7.60 (11H, m) Example 63 2-mercapto-7- (4-phenacylthio)
( Xyphenyl) heptanoic acid (Exemplary Compound No. 1-94) 1) 5- [5- (4-phenacyloxyphenyl) pen
Chill] thiazolidine -2 4- dione (Compound No. 9-88) In the same manner as 1) of Example 44, 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4-dione 2. By reacting 0 g with 1.57 g of phenacyl bromide, 5- [5- (4-phenacyloxyphenyl) pentyl] thiazolidine-2,4-dione.
77 g were obtained as a pale yellow oil (62% yield).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.20-2.30 (8H, m), 2.55 (2H, t, J = 7Hz), 4.26 (1
(H, dd, J = 4Hz, J = 9Hz), 5.25 (2H, s), 6.85 (2H, d, J = 9Hz), 7.
10 (2H, d, J = 9Hz), 7.40-7.75 (3H, m), 7.90-8.10 (2H, m),
8.60 (1H, brs) 2) 2-mercapto-7- (4-phenacyloxyphene )
Nyl) heptanoic acid 5- [5] obtained in 1) in the same manner as in 3) of Example 3
0.83 g of 2-mercapto-7- [4- (3-methoxybenzyloxy) phenyl] heptanoic acid was obtained as a colorless oil from 1.77 g of-(4-phenacyloxyphenyl) pentyl] thiazolidine-2,4-dione. Obtained (yield 50%).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.20-2.05 (8H, m), 2.08 (1H, d, J = 9 Hz), 2.54 (2
H, t, J = 7Hz), 3.34 (1H, dt, J = 7Hz, J = 9Hz), 5.24 (2H, s),
6.85 (2H, d, J = 9Hz), 7.10 (2H, d, J = 9Hz), 7.40-7.75 (3H,
m), 7.90-8.10 (2H, m ) 13C-NMR (22.49MHz, δppm, CDCl 3): 27.
04, 28.50, 31.15, 34.84, 35.06, 40.69, 71.09, 114.
70, 128.14, 128.79,129.33, 133.77, 134.69, 135.61,
156.15, 178.58, 194.84 Example 64 2-mercapto-7- [4- (4-pyrimido
Dinylmethoxy) phenyl] heptanoic acid (Exemplary Compound No. 1-48) 1) 5- [5- [4- (4-Pyrimidinylmethoxy ) phenyl]
Eniru] pentyl] thia Zorijin-2,4-dione (Compound No. 9-48) In the same manner as 1) of Example 44, 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4 1.3 g of dione and 0.6 g of 4-chloromethylpyrimidine
To give 5- [5- [4- (4-pyrimidinylmethoxy) phenyl] pentyl] thiazolidine-
1.19 g of 2,4-dione was obtained as a colorless solid (yield 69%).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.20-2.30 (8H, m), 2.57 (2H, t, J = 7Hz), 4.26 (1
H, dd, J = 4Hz, J = 9Hz), 5.16 (2H, s), 6.88 (2H, d, J = 9Hz), 7.
12 (2H, d, J = 9Hz), 7.65 (1H, dd, J = 1Hz, J = 5Hz), 8.75 (1H,
d, J = 5Hz), 9.16 (1H, d, J = 1Hz) 2) 2-mercapto-7- [4- (4-pyrimidinylmethyl
Butoxy) phenyl] heptene 3 Tan acid Example 3) and in the same manner, resulting in 1) 5- [5
0.39 g of 2-mercapto-7- [4- (4-pyrimidinylmethoxy) phenyl] heptanoic acid was obtained from 0.67 g of-[4- (4-pyrimidinylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione as a colorless solid. (62% yield).

1H-NMR (89.55 MHz, δ ppm, CD
Cl_Three-CD_ThreeOD): 1.20-2.05 (8H, m), 2.56 (2H, t, J = 7
Hz), 3.30 (1H, t, J = 7Hz), 5.16 (2H, s), 6.88 (2H, d, J = 9H
z), 7.12 (2H, d, J = 9Hz), 7.65 (1H, dd, J = 1Hz, J = 5Hz), 8.7
5 (1H, d, J = 5Hz), 9.16 (1H, d, J = 1Hz) 13C-NMR (22.49MHz, δppm, CDCl_Three-CD_Three
OD): 27.14, 28.66, 31.37, 34.89, 35.49, 41.02,
69.30, 114.65, 118.60, 129.60, 135.99, 155.93, 157.
50, 158.04, 166.98, 175.76 Example 652-mercapto-7- [4- (2-hydro
[Xy-2-phenethyloxy) phenyl] heptanoic acid
(Exemplified Compound No. 1-97) 2-mercapto-7- (4-f) obtained in Example 63-2)
Enacyloxyphenyl) heptanoic acid 60 mg
Dissolved in 5 ml of ethanol, and cooled under ice-cooling.
7 mg was added little by little, and the mixture was stirred for 30 minutes. reaction
After evaporating the solvent of the liquid, dilute hydrochloric acid was added and extracted with ethyl acetate.
The organic layer was dried with anhydrous sodium sulfate. Evaporate the solvent
After that, the residue is subjected to silica gel column chromatography.
From the flow of 1% methanol-chloroform.
LUCAPTO-7- [4- (2-hydroxy-2-phenethyl)
[Roxy) phenyl] heptanoic acid 56mg colorless oil
(93% yield).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.20-2.05 (8H, m), 2.06 (1H, d, J = 9 Hz), 2.54 (2
H, t, J = 7Hz), 3.30 (1H, dt, J = 7Hz, J = 9Hz), 3.85-4.15 (2H,
m), 5.10 (1H, dd, J = 4Hz, J = 8Hz), 6.85 (2H, d, J = 9Hz), 7.1
0 (2H, d, J = 9Hz), 7.20-7.50 (5H, m) 13C-NMR (22.49MHz, δppm, CDCl 3): 27.
04, 28.50, 31.21, 34.78, 35.06, 40.69, 72.60, 73.4
1, 114.54, 126.24,128.08, 128.46, 129.28, 135.24,
139.62, 156.48, 178.80 Example 66 6- (3-benzyloxyphenoxy)-
2-mercaptohexanoic acid (Exemplified Compound No. 5-14) 1) 5- [4- (3-benzyloxyphenoxy) butyi
Riden] thiazolidine- 2,4-dione In the same manner as in Example 3 1), 2.5-g of 4- (3-benzyloxyphenoxy) butanal is used to give 5- [4-
2.0 g of (3-benzyloxyphenoxy) butylidene] thiazolidine-2,4-dione were obtained (yield 5).
9%).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.40-2.55 (4H, m), 3.95 (2H, t, J = 6Hz), 5.05 (2
H, s), 6.40-6.60 (3H, m), 6.95-7.50 (7H, m) 2) 5- [4- (3-benzyloxyphenoxy) buty
Ru] thiazolidine-2,4 -dione (Exemplary Compound No. 1
3-14) 5- [4] obtained in 1) in the same manner as in 2) of Example 3
-(3-benzyloxyphenoxy) butylidene] thiazolidine-2,4-dione from 2.0 g of 5- [4-
1.1 g of (3-benzyloxyphenoxy) butyl] thiazolidine-2,4-dione were obtained as a colorless solid (yield 55%).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.40-2.05 (6H, m), 3.95 (2H, t, J = 6Hz), 4.30 (1
(H, dd, J = 4Hz, J = 9Hz), 5.05 (2H, s), 6.40-6.60 (3H, m), 7.0
5-7.50 (6H, m), 8.35 (1H, brs) 3) 6- (3-benzyloxyphenoxy) -2-mer
Captohexanoic acid 5- [4] obtained in 2) in the same manner as in 3) of Example 3
-(3-benzyloxyphenoxy) butyl] thiazolidine-2,4-dione from 0.8 g of 6- (3-benzyloxyphenoxy) -2-mercaptohexanoic acid
0.45 g was obtained as a colorless solid (60% yield).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.45-2.05 (6H, m), 2.15 (1H, d, J = 9 Hz), 3.34 (1
H, dt, J = 7Hz, J = 9Hz), 3.95 (2H, t, J = 6Hz), 5.05 (2H, s),
6.40-6.70 (3H, m), 7.05-7.55 (6H, m) Example 67 6- (4-benzyloxy-2-methylf)
Enoxy) -2-mercaptohexanoic acid (Exemplified Compound No. 5-65) 1) 5- [4- (4-benzyloxy-2-methylphen)
Phenoxy) butylidene] 1 Ji azolidine-2,4-dione Example 3) in analogy to 4- (4-benzyloxy-2-methylphenoxy) flatweed - than Le 1.9 g 5-[4- (4 -Benzyloxy-2-methylphenoxy) butylidene] thiazolidine-2,4-dione
8 g were obtained (yield 70%).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.70-2.55 (4H, m), 2.20 (3H, s), 3.95 (2H, t, J =
6Hz), 5.00 (2H, s), 6.60-6.90 (3H, m), 7.11 (1H, t, J = 8H
z), 7.20-7.55 (5H, m), 8.95 (1H, brs) 2) 5- [4- (4-benzyloxy-2-methylphen)
Phenoxy) butyl] thiazole-2,4-dione (Compound No. 13-54) in the same manner as in 2) of Example 3, obtained in 1) 5- [4
-(4-benzyloxy-2-methylphenoxy) butylidene] thiazolidine-2,4-dione From 1.8 g, 5- [4- (4-benzyloxy-2-methylphenoxy) butyl] thiazolidine-2,4- Zeon 0.
94 g was obtained (52% yield).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.45-2.25 (6H, m), 2.20 (3H, s), 3.95 (2H, t, J =
6Hz), 4.26 (1H, dd, J = 4Hz, J = 9Hz), 5.00 (2H, s), 6.60-6.9
0 (3H, m), 7.20-7.55 (5H, m), 8.55 (1H, brs) 3) 6- (4-benzyloxy-2-methylphenoxy )
) -2-3 Merukaputoheki San acid Example 3) and in the same manner, obtained in 2) 5- [4
-(4-benzyloxy-2-methylphenoxy) butyl] thiazolidine-2,4-dione from 0.94 g to 6
-(4-benzyloxy-2-methylphenoxy) -2
-0.51 g of mercaptohexanoic acid was obtained (yield 58%).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.45-2.05 (6H, m), 2.09 (1H, d, J = 9Hz), 2.20 (3
H, s), 3.36 (1H, dt, J = 7Hz, J = 9Hz), 3.93 (2H, t, J = 6Hz), 5.
00 (2H, s), 6.60-6.85 (3H, m), 7.20-7.55 (5H, m) Example 68 6- (4-benzyloxy-3-methylf)
Enoxy) -2-mercaptohexanoic acid (Exemplified Compound No. 5-67) 1) 5- [4- (4-benzyloxy-3-methylphen)
Phenoxy) butylidene] 1 Ji azolidine-2,4-dione Example 3) in analogy to 4- (4-benzyloxy-3-methylphenoxy) flatweed - than Le 1.0 g 5-[4- (4 -Benzyloxy-3-methylphenoxy) butylidene] thiazolidine-2,4-dione
92 g were obtained (80% yield).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.70-2.60 (4H, m), 2.24 (3H, s), 3.95 (2H, t, J =
6Hz), 5.03 (2H, s), 6.60-6.90 (3H, m), 7.10 (1H, t, J = 8H
z), 7.20-7.55 (5H, m), 9.30 (1H, brs) 2) 5- [4- (4-benzyloxy-3-methylphen)
Phenoxy) butyl] thiazole-2,4-dione (Compound No. 13-55) in the same manner as in 2) of Example 3, obtained in 1) 5- [4
From 0.8 g of-(4-benzyloxy-3-methylphenoxy) butylidene] thiazolidine-2,4-dione, 5- [4- (4-benzyloxy-3-methylphenoxy) butyl] thiazolidine-2,4- Zeon 0.
5 g was obtained (62% yield).

1H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.45-2.25 (6H, m), 2.24 (3H, s), 3.95 (2H, t, J =
6Hz), 4.27 (1H, dd, J = 4Hz, J = 9Hz), 5.03 (2H, s), 6.60-6.9
0 (3H, m), 7.20-7.55 (5H, m), 8.90 (1H, brs) 3) 6- (4-benzyloxy-3-methylphenoxy )
) -2-3 Merukaputoheki San acid Example 3) and in the same manner, obtained in 2) 5- [4
-(4-benzyloxy-3-methylphenoxy) butyl] thiazolidine-2,4-dione
(4-benzyloxy-3-methylphenoxy) -2-
0.24 g of mercaptohexanoic acid was obtained as a colorless solid (yield 51%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.45-2.05 (6H, m), 2.09 (1H, d, J = 9Hz), 2.24 (3H,
s), 3.36 (1H, dt, J = 7Hz, J = 9Hz), 3.94 (2H, t, J = 6Hz), 5.03
(2H, s), 6.60-6.85 (3H, m), 7.20-7.55 (5H, m) Example 69 2-mercapto-7- [4- [2- (2-
Thienyl) -2-oxoethoxy] phenyl] heptane
Acid (Exemplified Compound No. 1-100) 1) 5- [5- [4- [2- (2-thienyl) -2-o]
[Xoethoxy] phenyl ] pentyl] thiazolidine-
2,4-dione (exemplary compound number 9-90) In the same manner as in Example 44-1), 2.0 g of 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4-dione and 2- ( Bromoacetyl) thiophene
By reacting 1.6 g, 5- [5- [4-
[2- (2-thienyl) -2-oxoethoxy] phenyl] pentyl] thiazolidine-2,4-dione 1.4
6 g was obtained as a colorless solid (51% yield).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.30 (8H, m), 2.53 (2H, t, J = 7Hz), 4.23 (1H,
dd, J = 4Hz, J = 8Hz), 5.07 (2H, s), 6.85 (2H, d, J = 9Hz), 7.10
(2H, d, J = 9Hz), 7.14 (1H, dd, J = 4Hz, J = 5Hz), 7.69 (1H, dd,
J = 1Hz, J = 5Hz), 7.95 (1H, dd, J = 1Hz, J = 4Hz), 9.29 (1H, br
s) 2) 2-mercapto-7- [4- [2- (2-thienyl
L) -2-Oxoethoxy ] phenyl] heptanoic acid 5- [5-] obtained in 1) in the same manner as in 3) of Example 3
[4- [2- (2-thienyl) -2-oxoethoxy]
Phenyl] pentyl] thiazolidine-2,4-dione
From 1.38 g, 2-mercapto-7- [4- [2-
0.62 g of (2-thienyl) -2-oxoethoxy] phenyl] heptanoic acid was obtained as a slightly yellow solid (yield 48%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.05 (8H, m), 2.08 (1H, d, J = 9Hz), 2.54 (2H, m
t, J = 7Hz), 3.34 (1H, dt, J = 7Hz, J = 9Hz), 5.06 (2H, s), 6.8
5 (2H, d, J = 9Hz), 7.10 (2H, d, J = 9Hz), 7.14 (1H, dd, J = 4Hz,
J = 5Hz), 7.69 (1H, dd, J = 1Hz, J = 5Hz), 7.95 (1H, dd, J = 1Hz,
J = 4 Hz) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 27.
04, 28.55, 31.21, 34.84, 35.06, 40.74, 71.74, 114.
65, 128.19, 129.44, 133.23, 134.59, 135.83, 140.65,
156.04, 178.85, 188.60 Example 70 2-mercapto-7- [4- [2-hydro
[Xy-2- (2-thienyl) ethoxy] phenyl] hept
Tannic acid (Exemplified Compound No. 1-103) 2- (Oxidone) obtained in Example 69-2) in the same manner as in Example 65.
Mercapto-7- [4- [2- (2-thienyl) -2-
Oxoethoxy] phenyl] heptanoic acid 70 mg to 2-mercapto-7- [4- [2-hydroxy-2-
(2-thienyl) ethoxy] phenyl] heptanoic acid 4
8 mg was obtained as a colorless oil (yield 68%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.20-2.05 (8H, m), 2.07 (1H, d, J = 9Hz), 2.54 (2H,
t, J = 7Hz), 3.30 (1H, dt, J = 7Hz, J = 9Hz), 4.00-4.20 (2H,
m), 5.35 (1H, dd, J = 4Hz, J = 7Hz), 6.85 (2H, d, J = 9Hz), 7.1
0 (2H, d, J = 9Hz), 7.00-7.20 (2H, m), 7.28 (1H, dd, J = 1Hz, J
= 5 Hz) 13 C-NMR (22.49 MHz, δ ppm, CDCl ₃ ): 26.9
8, 28.50, 31.21, 34.78, 35.00, 40.69, 68.86, 72.9
8, 114.59, 124.67,125.16, 126.73, 129.33, 135.40,
142.93, 156.31, 178.90 Example 71 2-mercapto-7- [4- (5-methyl
-2- thienylmethoxy ) phenyl] heptanoic acid (Exemplary Compound No. 1-104) 1) 5- [5- [4- (5-methyl-2-thienylmethol)
) Phenyl] pentyl] thiazolidine-2,4-
On (exemplified compound number 9-91) In the same manner as in Example 44-1), 1.5 g of 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4-dione and 2-chloromethyl-5 -Methylthiophene was reacted with 1.2 g to give 5- [5- [4
1.15 g of-(5-methyl-2-thienylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione was obtained as a pale yellow oil (yield 55%).

1 H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.25-1.80 (6H, m), 1.80-2.30 (2H, m), 2.46 (3H, m
s), 2.55 (2H, t, J = 7Hz), 4.26 (1H, dd, J = 4Hz, J = 9Hz), 5.0
9 (2H, s), 6.60-6.66 (1H, m), 6.82-6.93 (3H, m), 7.10 (2
H, d, J = 9Hz), 8.96 (1H, brs) 2) 2-mercapto-7- [4- (5-methyl-2 -thio)
Phenylmethoxy) 3 of the phenyl] heptanoic acid Example 3) and in the same manner, resulting in 1) 5- [5
-[4- (5-methyl-2-thienylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione 1.13
g to give 2-mercapto-7- [4- (5-methyl-2-
Thienylmethoxy) phenyl] heptanoic acid 0.69 g
Was obtained as a pale yellow solid (65% yield).

1 H-NMR (89.55 MHz, δ ppm, CD
Cl ₃ ): 1.20-1.95 (8H, m), 2.08 (1H, d, J = 9 Hz), 2.46 (3
H, s), 2.54 (2H, t, J = 7Hz), 3.34 (1H, dt, J = 7Hz, J = 9Hz),
5.09 (2H, s), 6.60-6.67 (1H, m), 6.82-6.98 (3H, m), 7.10
(2H, d, J = 9 Hz) Example 72 2-mercapto-7- [3- (2 -thienyl
Rumethoxy) phenyl] heptanoic acid (Exemplary Compound No. 5
-66) 1) 5- [5- [3- (2-thienylmethoxy) phenyl]
Le] pentyl] thiazol Jin-2,4-dione (Compound No. 13-56) in the same manner as in 1) of Example 44 5- [5- (3-hydroxyphenyl) pentyl] thiazolidine-2,4-dione 1.15 g and 2-chloromethylthiophene 0.6 g
To give 5- [5- [3- (2-thienylmethoxy) phenyl] pentyl] thiazolidine-
0.7 g of 2,4-dione was obtained as a slightly yellow solid (yield 45%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.70 (6H, m), 1.85-1.95 (1H, m), 2.10-2.20
(1H, m), 2.59 (2H, t, J = 8Hz), 4.26 (1H, dd, J = 4Hz, J = 9Hz),
5.21 (2H, s), 7.00 (1H, dd, J = 3Hz, J = 5Hz), 7.10 (1H, dd, J
= 1Hz, J = 3Hz), 7.32 (1H, dd, J = 1Hz, J = 5Hz), 7.99 (1H, brs) 2) 2-mercapto-7- [3- (2-thienylmethoxy)
C) Phenyl] heptanoic acid 5- [5-] obtained in 1) in the same manner as in 3) of Example 3.
[3- (2-thienylmethoxy) phenyl] pentyl]
From 0.2 g of thiazolidine-2,4-dione, 0.125 g of 2-mercapto-7- [3- (2-thienylmethoxy) phenyl] heptanoic acid was obtained as a slightly yellow solid (yield 67%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.25-1.55 (4H, m), 1.55-1.80 (3H, m), 1.85-2.00
(1H, m), 2.08 (1H, d, J = 9Hz), 2.56 (2H, t, J = 8Hz), 3.30
(1H, dt, J = 7Hz, J = 9Hz), 5.18 (2H, s), 6.70-6.85 (3H, m),
6.98 (1H, dd, J = 3Hz, J = 5Hz), 7.08 (1H, dd, J = 1Hz, J = 3Hz),
7.29 (1H, dd, J = 1 Hz, J = 5 Hz), 7.18 (1 H, t, J = 8 Hz) 13 C-NMR (100 MHz, δ ppm, CDCl ₃ ): 27.03,
28.56, 30.89, 34.97, 35.73, 40.74, 64.82, 111.87,
115.18, 121.31,126.00, 126.62, 129.11, 139.25, 14
3.99, 158.15, 179.43 Example 73 2-mercapto-7- [4- [2- (5-
Methyl-2-phenyl-4-oxazolyl) ethoxy]
Phenyl] heptanoic acid (Exemplary Compound No. 1-105) 1) 5- [5- [4- [2- (5-methyl-2- phenyl )
4- Oxazolyl ) ethoxy] phenyl] pentyl
[Den] thiazolidine-2,4-dione 5- [4- [2- (5-
Methyl-2-phenyl-4-oxazolyl) ethoxy]
From 5.0 g of phenyl] pentanal, 5- [5- [4
4.0 g of-[2- (5-methyl-2-phenyl-4-oxazolyl) ethoxy] phenyl] pentylidene] thiazolidine-2,4-dione was obtained as a yellow solid (yield 63%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.32-1.60 (4H, m), 2.22 (2H, m), 2.37 (3H, s), 2.
51 (2H, t, J = 7Hz), 2.97 (2H, t, J = 7Hz), 4.23 (1H, t, J = 7H
z), 6.82 (2H, d, J = 9Hz), 7.00-7.08 (3H, m), 7.39-7.44 (3
H, m), 7.95-7.99 (2H, m) 2) 5- [5- [4- [2- (5-methyl-2-phenyl
4-Oxazolyl) ethoxy] phenyl] pent
Ru] thiazolidine-2,4-dione (Exemplary Compound No. 9
-100) 5- [5] obtained in 1) in the same manner as in 2) of Example 3.
From 4.0 g of-[4- [2- (5-methyl-2-phenyl-4-oxazolyl) ethoxy] phenyl] pentylidene] thiazolidine-2,4-dione, 5- [5-
3.0 g of [4- [2- (5-methyl-2-phenyl-4-oxazolyl) ethoxy] phenyl] pentyl] thiazolidine-2,4-dione was obtained as a colorless solid (yield 74%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.32-1.60 (6H, m), 1.87 (1H, m), 2.12 (1H, m), 2.
37 (3H, s), 2.51 (2H, t, J = 7Hz), 2.97 (2H, t, J = 7Hz), 4.20
-4.25 (3H, m), 6.82 (2H, d, J = 9Hz), 7.05 (2H, d, J = 9Hz),
7.39-7.44 (3H, m), 7.95-7.99 (2H, m) 3) 2-mercapto-7- [4- [2- (5-methyl-
2-phenyl-4-Oki Sazoriru) ethoxy] phenylene
5-heptanoic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3.
-[4- [2- (5-methyl-2-phenyl-4-oxazolyl) ethoxy] phenyl] pentyl] thiazolidine-2,4-dione from 2.5 g of 2-mercapto-7
1.6 g of-[4- [2- (5-methyl-2-phenyl-4-oxazolyl) ethoxy] phenyl] heptanoic acid
Was obtained as a colorless solid (67% yield).

1H-NMR (400 MHz, δ ppm, CDC
l_Three): 1.22-1.51 (4H, m), 1.53-1.61 (2H, m), 1.72 (1H,
m), 1.92 (1H, m), 2.08 (1H, d, J = 9Hz), 2.37 (3H, s), 2.52
(2H, t, J = 7Hz), 2.98 (2H, t, J = 7Hz), 3.31 (1H, dt, J = 7Hz, J
= 9Hz), 4.21 (2H, t, J = 7Hz), 6.81 (2H, d, J = 9Hz), 7.04 (2H
H, d, J = 9Hz), 7.39-7.44 (3H, m), 7.95-7.99 (2H, m) 13C-NMR (100 MHz, δ ppm, CDCl_Three): 10.41,
26.30, 27.23, 28.65, 31.40, 34.93, 35.35, 40.91, 6
6.72, 114.31, 125.90, 127.23, 128.56, 129.07, 129.
84, 132.38, 134.51, 145.02, 156.56, 159.37, 177.17 Example 742-mercapto-7- [4- (2-phenyl
Ru-4-thiazolylmethoxy) phenyl] heptanoic acid
(Exemplified Compound No. 1-106) 1)5- [5- [4- (2-phenyl-4-thiazolyl)
Methoxy) phenyl] pe Alkylidene] thiazolidine-
2,4-dione In the same manner as in 1 of Example 3, 5- [4- (2-phenyl)
Ru-4-thiazolylmethoxy) phenyl] pentanal
 From 3.9 g, 5- [5- [4- (2-phenyl-4-
Thiazolylmethoxy) phenyl] pentylidene] thiazo
3.0 g of lysine-2,4-dione were obtained as a yellow solid.
(Yield 59%).

1 H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.32-1.65 (4H, m), 2.22 (2H, m), 2.56 (2H, t, J = 7H
z), 5.25 (2H, d, J = 1Hz), 6.94 (2H, d, J = 9Hz), 7.00-7.08
(3H, m), 7.31 (1H, d, J = 1Hz), 7.41-7.48 (3H, m), 8.01-7.
91 (2H, m) 2) 5- [5- [4- (2-phenyl-4-thiazolyl)
Methoxy) phenyl] pentyl] thiazolidine-2,4
- In the same manner as dione 2 (Compound No. 9-93) Example 3), 5- [5- [4- (2-
Phenyl-4-thiazolylmethoxy) phenyl] pentylidene] thiazolidine-2,4-dione from 3.0 g of 5- [5- [4- (2-phenyl-4-thiazolylmethoxy) phenyl] pentyl] thiazolidine- 2.1 g of 2,4-dione were obtained as a colorless solid (yield 69).
%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.32-1.65 (6H, m), 1.89 (1H, m), 2.12 (1H, m), 2.
56 (2H, t, J = 7Hz), 4.24 (1H, dd, J = 5Hz, J = 9Hz), 5.25 (2H,
d, J = 1Hz), 6.94 (2H, d, J = 9Hz), 7.08 (2H, d, J = 9Hz), 7.31
(1H, d, J = 1Hz), 7.41-7.48 (3H, m), 7.91-8.01 (2H, m) 3) 2-mercapto-7- [4- (2-phenyl-4-
In the same manner as thiazolylmethoxy) off Eniru] 3 heptanoic acid Example 3), obtained in 2) 5- [5
-[4- (2-phenyl-4-thiazolylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione
2.0 g of 2-mercapto-7- [4- (2-phenyl-4-thiazolylmethoxy) phenyl] heptanoic acid
1.4 g were obtained as a colorless solid (yield 75%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.22-1.51 (4H, m), 1.53-1.61 (2H, m), 1.73 (1H,
m), 1.92 (1H, m), 2.08 (1H, d, J = 9Hz), 2.55 (2H, t, J = 7H
z), 3.31 (1H, dt, J = 7Hz, J = 9Hz), 5.25 (2H, d, J = 1Hz), 6.9
3 (2H, d, J = 9Hz), 7.08 (2H, d, J = 9Hz), 7.31 (1H, d, J = 1Hz),
7.41-7.48 (3H, m), 7.91-8.00 (2H, m) 13C-NMR (100MHz, δppm, CDCl 3): 27.20,
28.66, 31.37, 34.95, 35.22, 40.82, 66.43, 114.54,
115.74, 126.49,128.82, 129.16, 130.03, 133.19, 13
4.98, 153.48, 156.32, 168.53, 178.04 Example 75 7- (3-benzyloxyphenyl) -2
-Mercaptoheptanoic acid (Exemplary Compound No. 1-24) 1) 5- [5- (3-benzyloxyphenyl) penty
Riden] thiazolidine- 2,4-dione In the same manner as in Example 3 1), 5- [3-benzyloxyphenyl) pentanal was obtained from 3.95 g of 5- [5-
4.96 g of (3-benzyloxyphenyl) pentylidene] thiazolidine-2,4-dione were obtained (yield 92%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.50-1.70 (4H, m), 2.21 (2H, q, J = 7Hz), 2.60 (2H,
t, J = 8Hz), 5.05 (2H, s), 6.75-6.85 (3H, m), 7.01 (1H, t, J
= 8Hz), 7.20 (1H, t, J = 8Hz), 7.25-7.45 (5H, m) 2) 5- [5- (3-benzyloxyphenyl ) penty
Ru] thiazolidine-2,4-dione (Exemplary Compound No. 9
-24) 5- [5] obtained in 1) in the same manner as in 2) of Example 3.
-(3-benzyloxyphenyl) pentylidene] thiazolidine-2,4-dione from 4.96 g, 5- [5
2.8 g of-(3-benzyloxyphenyl) pentyl] thiazolidine-2,4-dione was obtained as a colorless oil (yield 56%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.70 (6H, m), 1.85-1.95 (1H, m), 2.10-2.20
(1H, m), 2.58 (2H, t, J = 8Hz), 4.25 (1H, dd, J = 4Hz, J = 9Hz),
5.05 (2H, s), 6.75-6.85 (3H, m), 7.19 (1H, t, J = 8Hz), 7.
25-7.45 (5H, m), 8.32 (1H, brs) 3) 7- (3-benzyloxyphenyl) -2-merca
Putheptanic acid 5- [5] obtained in 2) in the same manner as in 3) of Example 3
-(3-benzyloxyphenyl) pentyl] thiazolidine-2,4-dione 7- (3-benzyloxyphenyl) -2-mercaptoheptanoic acid from 2.07 g
1.3 g were obtained as a colorless oil (yield 67%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.55 (4H, m), 1.55-1.80 (3H, m), 1.85-2.00
(1H, m), 2.08 (1H, d, J = 9Hz), 2.58 (2H, t, J = 8Hz), 3.33
(1H, dt, J = 7Hz, J = 9Hz), 5.05 (2H, s), 6.75-6.85 (3H, m),
7.19 (1H, t, J = 8Hz), 7.25-7.45 (5H, m) 13C-NMR (100MHz, δppm, CDCl ₃ ): 27.02,
28.54, 30.88, 34.96, 35.72, 40.70, 69.80, 111.71,
115.01, 120.96,127.33, 127.72, 128.37, 129.07, 13
6.97, 143.95, 158.62, 179.20 Example 76 2-mercapto-7- [6- (2-thienyl
L-methoxy) -2-naphthyl] heptanoic acid (Exemplary Compound No. 2-41) 1) 5- [5- [6- (2- thienylmethoxy) -2-]
Naphthyl] pentylidene ] thiazolidine-2,4-di
In the same manner as 1) of emissions Example 3 5- [6- (2-thienyl) -2- naphthyl] pentanal 3.58
g to give 5- [5- [6- (2-thienylmethoxy) -2]
3.72 g of [-naphthyl] pentylidene] thiazolidine-2,4-dione were obtained (yield 80%).

1H-NMR (89.55 MHz, δ ppm, CDC
l_Three): 1.40-1.95 (4H, m), 2.23 (2H, q, J = 8Hz), 2.76 (2H, m
t, J = 7Hz), 5.32 (2H, s), 6.90-7.80 (10H, m), 8.90 (1H, br
s) 2)5- [5- [6- (2-thienylmethoxy) -2-
Naphthyl] pentyl] Azolidine-2,4-dione
(Exemplified Compound No. 10-41) 5- [5] obtained in 1) in the same manner as in 2) of Example 3
-[6- (2-thienylmethoxy) -2-naphthyl] pe
[N.tylidene] thiazolidine-2,4-dione 3.67 g
From 5- [5- [6- (2-thienylmethoxy) -2
-Naphthyl] pentyl] thiazolidine-2,4-dione
 2.62 g were obtained as a colorless solid (yield 71
%).

1 H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.35-1.65 (4H, m), 1.65-1.75 (2H, m), 1.85-1.95
(1H, m), 2.10-2.20 (1H, m), 2.74 (2H, t, J = 8Hz), 4.26 (1
H, dd, J = 4Hz, J = 9Hz), 5.33 (2H, s), 7.02 (1H, dd, J = 4Hz, J =
5Hz), 7.10-7.35 (4H, m), 7.53 (1H, s), 7.67 (2H, t, J = 9H
z), 8.10 (1H, brs) 3) 2-mercapto-7- [6- (2-thienylmethoxy)
) -2-naphthyl] 3 of heptane acid Example 3) and in the same manner, obtained in 2) 5- [5
-[6- (2-thienylmethoxy) -2-naphthyl] pentyl] thiazolidine-2,4-dione 2-mercapto-7- [6- (2-thienylmethoxy) -2-naphthyl] heptanoic acid from 1.65 g 1.18 g were obtained as a colorless solid (76% yield).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.60 (4H, m), 1.65-1.80 (3H, m), 1.85-2.00
(1H, m), 2.09 (1H, d, J = 9Hz), 2.73 (2H, t, J = 8Hz), 3.34 (1
H, dt, J = 7Hz, J = 9Hz), 5.32 (2H, s), 7.02 (1H, dd, J = 4Hz, J =
5Hz), 7.10-7.35 (4H, m), 7.53 (1H, s), 7.67 (2H, t, J = 9H
z) 13 C-NMR (100 MHz, δ ppm, CDCl ₃ ): 27.14,
28.67, 31.11, 35.10, 35.72, 40.72, 65.00, 107.20,
118.92, 126.13, 126.18, 126.70, 126.74, 126.85, 12
7.79, 128.91, 129.24, 132.66, 137.81, 139.10, 155.
65, 178.73 Example 77 7- (2-benzoylbenzofuran-5-
Yl) -2-mercaptoheptanoic acid (Exemplary Compound No. 4
-22) 1) 5- [5- [2-[[1- (tert-butyldimethyl)
Tylsilyl) oxy-1 -phenyl] methyl] benzof
Lan-5-yl] pentyl] thiazolidine-2,4-di
In the same manner as on the first lithium hexamethyldisilazide in place of lithium diisopropylamide uses examples 1) iodide 5- [2 - [[1-(tert-butyldimethylsilyl) oxy-1-phenyl ] Methyl] benzofuran-5-yl] pentyl from 6.9 g of 5- [5-
[2-[[1- (tert-Butyldimethylsilyl) oxy-1-phenyl] methyl] benzofuran-5-yl] pentyl] thiazolidine-2,4-dione 4.9
g were obtained as pale yellow candy (yield 73%).

1H-NMR (400 MHz, δ ppm, CDC
_{l 3): 0.06 (3H,} s), 0.08 (3H, s), 0.92 (9H, s), 1.34-1.
58 (4H, m), 1.64 (2H, m), 1.90 (1H, m), 2.13 (1H, m), 2.66
(2H, t, J = 8Hz), 4.24 (1H, dd, J = 4Hz, J = 9Hz), 5.86 (1H, s),
6.45 (1H, d, J = 2Hz), 7.04 (1H, dd, J = 2Hz, J = 8Hz), 7.25-7.
41 (5H, m), 7.46 (2H, m), 8.28 (1H, brs) 2) 5- [5- [2-[(1-hydroxy-1-phenyl
) Methyl] Benzofura down-5-yl] pentyl] Chia
Zolidine-2,4-dione 5- [5- [2-[[1- (tert-butyldimethylsilyl) oxy-1-phenyl] methyl] benzofuran-5
-Yl] pentyl] thiazolidine-2,4-dione
4.9 g and 1 M tetrabutylammonium fluoride-TH
20 ml of the F solution was stirred at room temperature for 1 hour. The residue obtained by distilling off the solvent was subjected to silica gel column chromatography, and 5- [5-
[2-[(1-hydroxy-1-phenyl) methyl] benzofuran-5-yl] pentyl] thiazolidine-2,
3.8 g of 4-dione was obtained as a colorless candy (yield quantitative).

1 H-NMR (400 MHz, δ ppm, CDC
_{l 3): 1.36-1.56 (4H,} m), 1.64 (2H, m), 1.86 (1H, m), 2.
11 (1H, m), 2.66 (2H, t, J = 8Hz), 4.21 (1H, dd, J = 4Hz, J = 9H
z), 5.92 (1H, s), 6.66 (1H, d, J = 2Hz), 7.04 (1H, dd, J = 2H
z, J = 8Hz), 7.27-7.47 (5H, m), 7.48 (2H, m), 8.73 (1H, br
s) 3) 5- [5- (2-benzoylbenzofuran-5-i
Le) pentyl] thiazol Jin-2,4-dione (Compound No. 11-12) 5- [5- [2 - [(1-hydroxy-1-phenyl)
Methyl] benzofuran-5-yl] pentyl] thiazolidine-2,4-dione 2.5 g, pyridinium chlorochromate 2.6 g and sodium acetate 1.0 g
Was stirred at room temperature for 1 hour. Ether was added to the reaction solution, and the mixture was filtered through silica gel. The filtrate was evaporated, and the resulting residue was subjected to silica gel column chromatography. The mixture was eluted with chloroform, and 5- [5- (2-benzoylbenzofuran-5-yl) pentyl] thiazolidine-2,
0.75 g of 4-dione was obtained as a pale yellow candy (30% yield).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.36-1.68 (6H, m), 1.92 (1H, m), 2.16 (1H, m), 2.
73 (2H, t, J = 8Hz), 4.27 (1H, dd, J = 4Hz, J = 9Hz), 7.31 (1H, d
d, J = 2Hz, J = 9Hz), 7.46-7.55 (5H, m), 7.64 (1H, t, J = 8Hz),
8.04 (2H, d, J = 8Hz), 8.47 (1H, brs) 4) 7- (2-benzoylbenzofuran-5-yl)-
2-mercaptoheptanoic acid 5- [5] obtained in 3) in the same manner as in 3) of Example 3.
-(2-benzoylbenzofuran-5-yl) pentyl] thiazolidine-2,4-dione from 0.75 g,
7- (2-benzoylbenzofuran-5-yl) -2-
0.39 g of mercaptoheptanoic acid was obtained as a pale yellow candy (57% yield).

1 H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.34-1.54 (4H, m), 1.63-1.79 (3H, m), 1.93 (1H,
m), 2.11 (1H, d, J = 9Hz), 2.72 (2H, t, J = 8Hz), 3.34 (1H, d
t, J = 7Hz, J = 9Hz), 7.32 (1H, d, J = 9Hz), 7.47-7.55 (5H, m),
7.63 (1H, m), 8.04 (2H, d, J = 8 Hz) 13C-NMR (100 MHz, δ ppm, CDCl ₃ ): 27.00,
28.46, 31.43, 34.99, 35.51, 40.65, 112.07, 116.46,
122.04, 126.92, 128.35, 129.27, 129.29, 132.69, 1
37.08, 138.16, 152.15, 154.53, 178.58, 184.27 Example 78 2-mercapto-7- [4- (3-methyl
-2- thienylmethoxy ) phenyl] heptanoic acid (Exemplary Compound No. 1-107) 1) 5- [5- [4- (3-methyl-2-thienylmethol)
) Phenyl] pentyl] thiazolidine -2 in the same manner as dione (1 Compound No. 9-94) Example 44), 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4 By reacting 1.5 g of dione with 1.2 g of 2-chloromethyl-3-methylthiophene, 5- [5- [4
1.11 g of-(3-methyl-2-thienylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione was obtained as a slightly yellow oil (yield 53%).

1 H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.80 (6H, m), 1.86-1.98 (1H, m), 2.10-2.24
(1H, m), 2.26 (3H, s), 2.55 (2H, t, J = 7Hz), 4.25 (1H, dd, J
= 4Hz, J = 9Hz), 5.10 (2H, s), 6.85 (1H, d, J = 5Hz), 6.90 (2
(H, d, J = 9Hz), 7.08 (2H, d, J = 9Hz), 7.23 (1H, d, J = 5Hz), 8.
55 (1H, brs) 2) 2-mercapto-7- [4- (3-methyl-2- thio)
Phenylmethoxy) 3 of the phenyl] heptanoic acid Example 3) and in the same manner, resulting in 1) 5- [5
-[4- (3-methyl-2-thienylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione 1.10
g to give 2-mercapto-7- [4- (3-methyl-2-
Thienylmethoxy) phenyl] heptanoic acid 0.70 g
Was obtained as a pale yellow solid (68% yield).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.68 (6H, m), 1.68-1.80 (1H, m), 1.88-2.00
(1H, m), 2.09 (1H, d, J = 9Hz), 2.26 (3H, s), 2.55 (2H, t, J =
7Hz), 3.34 (1H, dt, J = 7Hz, J = 9Hz), 5.09 (2H, s), 6.85 (1
H, d, J = 5Hz), 6.90 (2H, d, J = 9Hz), 7.08 (2H, d, J = 9Hz), 7.
23 (1H, d, J = 5 Hz) Example 79 7- (4-carboxymethoxyphenyl)
-2-mercaptoheptanoic acid (Exemplary Compound No. 1-11
0) 1) 5- [5- (4-methoxycarbonylmethoxyphene )
Yl) pentyl] thiazole-2,4-dione (Compound No. 9-95) In the same manner as 1) of Example 44, 5- [5- (4-hydroxyphenyl) pentyl] thiazolidine-2,4 By reacting 1.5 g of dione and 1.10 g of methyl bromoacetate, 5- [5- (4-methoxycarbonylmethoxyphenyl) pentyl] thiazolidine-2,4-
0.96 g of dione was obtained as a pale yellow oil (yield 51%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.80 (6H, m), 1.88-2.00 (1H, m), 2.12-2.25
(1H, m), 2.55 (2H, t, J = 7Hz), 3.81 (3H, s), 4.27 (1H, dd, J
= 4Hz, J = 9Hz), 4.62 (2H, s), 6.82 (1H, d, J = 8Hz), 7.08 (2
H, d, J = 8Hz), 8.56 (1H, brs) 2) 7- (4-carboxymethoxyphenyl) -2-me
5- [5] obtained in 1) in the same manner as in Example 3-3 ).
-(4-methoxycarbonylmethoxyphenyl) pentyl] thiazolidine-2,4-dione 7 from 0.96 g
0.61 g of-(4-carboxymethoxyphenyl) -2-mercaptoheptanoic acid was obtained as a colorless solid (yield 71%).

1H-NMR (400 MHz, δ ppm, CD ₃ O
D): 1.25-1.73 (7H, m), 1.80-1.93 (1H, m), 1.88-2.00
(1H, m), 2.53 (2H, t, J = 7Hz), 4.61 (2H, s), 6.83 (1H, d, J =
8 Hz), 7.08 (2H, d, J = 8 Hz) Example 80 7- (4-benzoylphenyl) -2-me
Lcaptoheptanoic acid (Exemplified Compound No. 1-113) 1) 5- [5- [4- (1-methoxymethoxy-1-f)
Enylmethyl) phenyl ] pentylidene] thiazolidine
-2,4-dione In the same manner as in 1) of Example 3, 4.6 g of 5- [4- (1-methoxymethoxy-1-phenylmethyl) phenyl] pentanal was used to obtain 5- [5- [4- (1 -Methoxymethoxy-1-phenylmethyl) phenyl] pentylidene] thiazolidine-2,4-dione (3.56 g) was obtained as a slightly yellow oil (yield 59%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.55-1.70 (4H, m), 2.22 (2H, q, J = 8Hz), 2.60 (2H,
t, J = 8Hz), 3.41 (3H, s), 4.68 (2H, s), 5.71 (1H, s), 7.00
(1H, t, J = 8Hz), 7.11 (2H, d, J = 8Hz), 7.20-7.40 (7H, m) 2) 5- [5- [4- (2-methoxyphenoxy ) fe
In the same manner as sulfonyl] 2 pentyl] thiazole-2,4-dione Example 3), obtained in 1) 5- [5
-[4- (1-Methoxymethoxy-1-phenylmethyl) phenyl] pentylidene] thiazolidine-2,4-
From 3.56 g of dione, 2.65 g of 5- [5- [4- (1-methoxymethoxy-1-phenylmethyl) phenyl] pentyl] thiazolidine-2,4-dione was obtained as a slightly yellow oily substance. Rate 74%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.70 (6H, m), 1.85-1.95 (1H, m), 2.05-2.15
(1H, m), 2.58 (2H, t, J = 8Hz), 3.41 (3H, s), 4.24 (1H, dd, J
= 4Hz, J = 9Hz), 4.68 (2H, s), 5.71 (1H, s), 7.11 (2H, d, J = 8
Hz), 7.20-7.40 (7H, m), 8.07 (1H, brs) 3) 5- [5- (4-benzoylphenyl) pentyl]
Thiazolidine-2,4-dione (Exemplary Compound No. 9-9)
6) To 1.31 g of 5- [5- [4- (1-methoxymethoxy-1-phenylmethyl) phenyl] pentyl] thiazolidine-2,4-dione obtained in 2), 20 ml of acetic acid and 48% hydrogen bromide were added. Add 30 ml of acid, and add
Heated for hours. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained 5-
[5- [4- (1-hydroxy-1-phenylmethyl)
[Phenyl] pentyl] thiazolidine-2,4-dione was immediately oxidized in the same manner as in Example 58-1) to give 5- [5-
(4-benzoylphenyl) pentyl] thiazolidine-
0.77 g of 2,4-dione was obtained as a colorless oil (yield 66%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.70 (6H, m), 1.85-1.95 (1H, m), 2.10-2.20
(1H, m), 2.70 (2H, t, J = 8Hz), 4.27 (1H, dd, J = 4Hz, J = 9Hz),
7.27 (2H, d, J = 8Hz), 7.48 (2H, t, J = 8Hz), 7.58 (1H, t, J = 8
Hz), 7.74 (2H, d, J = 8Hz), 7.79 (2H, d, J = 8Hz), 8.27 (1H, b
rs) 4) 7- (4-benzoylphenyl) -2-mercapto
Heptanoic acid Equivalent to 3) of Example 3, 5- [5] obtained in 3)
From (-(4-benzoylphenyl) pentyl] thiazolidine-2,4-dione (0.77), 0.33 g of 7- (4-benzoylphenyl) -2-mercaptoheptanoic acid was obtained as a colorless oil (yield: 46%). ).

1 H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.55 (4H, m), 1.60-1.80 (3H, m), 1.90-2.00
(1H, m), 2.11 (1H, d, J = 9Hz), 2.69 (2H, t, J = 8Hz), 3.34 (1
H, dt, J = 7Hz, J = 9Hz), 7.27 (2H, d, J = 8Hz), 7.48 (2H, t, J = 8
Hz), 7.58 (1H, t, J = 8Hz), 7.74 (2H, d, J = 8Hz), 7.79 (2H,
d, J = 8 Hz) 13 C-NMR (100 MHz, δ ppm, CDCl ₃ ): 27.09,
28.65, 30.81, 35.09, 35.85, 40.67, 128.15, 128.25,
129.90, 130.31, 132.14, 135.11, 137.78, 147.61, 1
78.02, 196.48 Example 81 2-mercapto-7- [4- (2- methoxy
[ Cifenoxy ) phenyl] heptanoic acid (Exemplary Compound No. 1-114) 1) 5- [5- [4- (2-methoxyphenoxy ) fe
In the same manner as sulfonyl] pentylidene] 1 Ji azolidine-2,4-dione Example 3), 5- [4- (from 2-methoxyphenoxy) phenyl] pentanal 1.45 g 5- [5- [4- ( 2-methoxyphenoxy) phenyl] pentylidene] thiazolidine-2,4-dione
1.31 g were obtained as a colorless oil (yield 67).
%).

1H-NMR (89.55 MHz, δ ppm, CDC
l ₃ ): 1.45-1.75 (4H, m), 2.24 (2H, q, J = 7 Hz), 2.59 (2
H, t, J = 8Hz), 3.85 (3H, s), 6.87 (2H, d, J = 8Hz), 7.10 (2H,
d, J = 8Hz), 6.80-7.15 (5H, m) 2) 5- [5- [4- (2-methoxyphenoxy ) fe
In the same manner as sulfonyl] pentyl] thiazole-2,4-dione 2 (Compound No. 9-97) Example 3), obtained in 1) 5- [5
-[4- (2-Methoxyphenoxy) phenyl] pentylidene] thiazolidine-2,4-dione From 1.31 g of 5- [5- [4- (2-methoxyphenoxy) phenyl] pentyl] thiazolidine-2,4- Zeon 0.
9 g was obtained as a pale yellow oil (yield 68%).

1 H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.70 (6H, m), 1.85-1.95 (1H, m), 2.10-2.20
(1H, m), 2.57 (2H, t, J = 8Hz), 3.85 (3H, s), 4.26 (1H, dd, J
= 4Hz, J = 9Hz), 6.87 (2H, d, J = 8Hz), 7.09 (2H, d, J = 8Hz),
6.85-7.15 (4H, m), 8.18 (1H, brs) 3) 2-mercapto-7- [4- (2-methoxypheno
) Phenyl] 3 hepta phosphate Example 3) and in the same manner, obtained in 2) 5- [5
-[4- (2-methoxyphenoxy) phenyl] pentyl] thiazolidine-2,4-dione
0.455 g of mercapto-7- [4- (2-methoxyphenoxy) phenyl] heptanoic acid was obtained as a pale yellow oil (yield 54%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.55 (4H, m), 1.55-1.80 (3H, m), 1.85-2.00
(1H, m), 2.09 (1H, d, J = 9Hz), 2.56 (2H, t, J = 8Hz), 3.33 (1
H, dt, J = 7Hz, J = 9Hz), 3.85 (3H, s), 6.87 (2H, d, J = 8Hz),
7.09 (2H, d, J = 8 Hz), 6.85-7.15 (4H, m) 13C-NMR (100 MHz, δ ppm, CDCl ₃ ): 27.12,
28.62, 31.25, 35.00, 35.13, 40.67, 56.02, 112.70,
117.32, 120.45,120.99, 124.30, 129.24, 136.57, 14
5.50, 151.14, 155.63, 178.20 Example 82 7- [4- (4-Fluorobenzyloxy)
C ) Phenyl] -2-mercaptoheptanoic acid (Exemplary Compound No. 1-37) 1) 5- [5- [4- (4-fluorobenzyloxy)
Phenyl] pentylidene ] thiazolidine-2,4-di
In the same manner as in 1) of Example 3, 6.7 g of 5- [4- (4-fluorobenzyloxy) phenyl] pentanal was used to obtain 5- [5- [4- (4-fluorobenzyloxy)
[Phenyl] pentylidene] thiazolidine-2,4-dione (6.08 g) was obtained as a slightly yellow solid (yield 67).
%).

1 H-NMR (400 MHz, δ ppm, CDC
l_Three): 1.50-1.70 (4H, m), 2.23 (2H, dt, J = 7Hz, J = 8Hz),
2.58 (2H, t, J = 7Hz), 5.00 (2H, s), 6.89 (2H, d, J = 9Hz), 7.0
2 (1H, t, J = 8Hz), 7.07 (2H, t, J = 9Hz), 7.08 (2H, d, J = 9Hz),
7.40 (2H, dd, J = 5Hz, J = 9Hz), 8.28 (1H, brs) 2)5- [5- [4- (4-fluorobenzyloxy)
Phenyl] pentyl] h Azolidine-2,4-dione
(Exemplified Compound No. 9-37) 5- [5] obtained in 1) in the same manner as in 2) of Example 3
-[4- (4-fluorobenzyloxy) phenyl] pe
[Nylidene] thiazolidine-2,4-dione 6.08 g
From 5- [5- [4- (4-fluorobenzyloxy)
C) phenyl] pentyl] thiazolidine-2,4-di
4.0 g was obtained as a colorless solid (yield 65).
%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.70 (6H, m), 1.85-1.95 (1H, m), 2.10-2.20
(1H, m), 2.55 (2H, t, J = 8Hz), 4.26 (1H, dd, J = 4Hz, J = 9Hz),
5.00 (2H, s), 6.88 (2H, d, J = 9Hz), 7.07 (2H, t, J = 9Hz), 7.
08 (2H, d, J = 9Hz), 7.40 (2H, dd, J = 6Hz, J = 9Hz), 8.09 (1H, b
rs) 3) 7- [4- (4-fluorobenzyloxy) phenyi
Le] -2 Merukaputohe heptanoic 3 acid Example 3) and in the same manner, obtained in 2) 5- [5
From -2.1 g of-[4- (4-fluorobenzyloxy) phenyl] pentyl] thiazolidine-2,4-dione, 1.56 g of 7- [4- (4-fluorobenzyloxy) phenyl] -2-mercaptoheptanoic acid Was obtained as a colorless solid (yield 79%).

1 H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.65 (6H, m), 1.65-1.80 (1H, m), 1.85-2.00
(1H, m), 2.09 (1H, d, J = 9Hz), 2.55 (2H, t, J = 8Hz), 3.33 (1
H, dt, J = 7Hz, J = 9Hz), 4.99 (2H, s), 6.88 (2H, d, J = 8Hz),
7.06 (2H, t, J = 9Hz), 7.08 (2H, d, J = 8Hz), 7.40 (2H, dd, J = 5
Hz, J = 9 Hz) 13 C-NMR (100 MHz, δ ppm, CDCl ₃ ): 27.12,
28.60, 31.36, 34.88, 35.13, 40.66, 69.39, 114.59,
115.39 (d, J _FC = 21.6Hz), 129.22, 129.24 (d, J _FC = 8.3Hz),
132.87 (d, J _FC = 3.3Hz), 134.94, 156.62,162.33 (d, J _FC =
246 Hz), 178.15 Example 83 2-mercapto-7- [2-fluoro-4
-(Benzyloxy) phenyl] heptanoic acid (Exemplary Compound No. 1-73) 1) 5- [5- [2-fluoro-4- (benzyloxy)
) Phenyl] Penchiride emissions] thiazolidine-2,4
Dione In the same manner as in Example 3 1), 5- [2-fluoro-4
-(Benzyloxy) phenyl] pentanal 3.4
From 3 g, 3.16 g of the title compound was obtained as a yellow oil (yield: 68%).

1H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.50-1.70 (4H, m), 2.20-2.30 (2H, m), 2.59 (2H,
t, J = 7Hz), 5.03 (2H, s), 6.66-6.73 (2H, m), 6.94-7.12 (2
H, m), 7.31-7.45 (5H, m), 8.32 (1H, brs) 2) 5- [5- [2-fluoro-4- (benzyloxy)
C) phenyl] pentyl] thiazolidine-2,4 -di
Down (Compound No. 9-73) In the same manner as in 2) of Example 3, obtained in 1) 5- [5
-[2-Fluoro-4- (benzyloxy) phenyl]
Pentylidene] thiazolidine-2,4-dione 3.1 g
As a result, 2.10 g of the title compound was obtained as a slightly yellow oil (yield 67%).

1H-NMR (400 MHz, δ ppm, CDCl ₃ ): 1.3
4-1.70 (6H, m), 1.86-1.98 (1H, m), 2.10-2.23 (1H, m), 2.
56 (2H, t, J = 7Hz), 4.26 (1H, dd, J = 4Hz, J = 9Hz), 5.03 (2H,
s), 6.62-6.73 (2H, m), 7.04 (1H, t, J = 8Hz), 7.30-7.44 (5
H, m), 8.11 (1H, brs) 3) 2-mercapto-7- [2-fluoro-4- (benzene
Jiruokishi) In the same manner as phenyl] 3 heptanoic acid Example 3), obtained in 2) 5- [5
-[2-Fluoro-4- (benzyloxy) phenyl]
[Pentyl] thiazolidine-2,4-dione (1.1 g) gave the title compound (0.76 g) as a colorless solid (yield 74%).

1H-NMR (400 MHz, δ ppm, CDCl ₃ ):
1.30-1.62 (6H, m), 1.69-1.79 (1H, m), 1.89-1.99 (1H, m),
2.09 (1H, d, J = 9Hz), 2.56 (2H, t, J = 7Hz), 3.33 (1H, dt, J =
7Hz, J = 9Hz), 5.02 (2H, s), 6.63-6.74 (2H, m), 7.04 (1H,
t, J = 8 Hz), 7.30-7.48 (5H, m) Example 84 2-mercapto-7- [2-fluoro-4
-(2 -Thienylmethoxy ) phenyl] heptanoic acid (Exemplary Compound No. 1-74) 1) 5- [5- [2-Fluoro-4- (2-thienylmeth)
Butoxy) phenyl] Pen Chiriden] thiazolidine -2,
4-dione 5- [2-fluoro-4] in the same manner as in Example 3 1).
-(2-thienylmethoxy) phenyl] pentanal
From 1.64 g, 1.39 g of the title compound was obtained as a yellow oil (yield: 63%).

1H-NMR (400 MHz, δ ppm, CDCl ₃ ):
1.50-1.70 (4H, m), 2.21-2.29 (2H, m), 2.59 (2H, t, J = 7H
z), 5.18 (2H, s), 6.66-6.73 (2H, m), 7.00-7.14 (4H, m),
7.33 (1H, psd, J = 1 Hz), 8.30 (1H, brs) 2) 5- [5- [2-fluoro-4- (2-thienylmeth)
Butoxy) phenyl] Pen chill] thiazolidine-2,4
In the same manner as dione 2 (Compound No. 9-74) Example 3), obtained in 1) 5- [5
-[2-Fluoro-4- (2-thienylmethoxy) phenyl] pentylidene] thiazolidine-2,4-dione
From 1.39 g, 0.87 g of the title compound was obtained as a pale yellow oil (yield: 62%).

1H-NMR (400 MHz, δ ppm, CDCl ₃ ):
1.31-1.68 (6H, m), 1.87-1.97 (1H, m), 2.11-2.21 (1H, m),
2.57 (2H, t, J = 7Hz), 4.25 (1H, dd, J = 4Hz, J = 9Hz), 5.18 (2
H, s), 6.64-6.72 (2H, m), 6.97-7.12 (3H, m), 7.34 (1H, ps
d, J = 1 Hz) 3) 2-mercapto-7- [2-fluoro-4- (2-
In the same manner as thienyl methoxy)-phenyl] 3 heptanoic acid Example 3), obtained in 2) 5- [5
-[2-Fluoro-4- (2-thienylmethoxy) phenyl] pentyl] thiazolidine-2,4-dione
From 85 g, 0.57 g of the title compound was obtained as a colorless solid (yield 72%).

1H-NMR (400 MHz, δ ppm, CDCl_Three):
1.32-1.67 (6H, m), 1.69-1.79 (1H, m), 1.88-1.98 (1H, m),
 2.09 (1H, d, J = 9Hz), 2.56 (2H, t, J = 7Hz), 3.33 (1H, dt, J
= 7Hz, J = 9Hz), 5.17 (2H, s), 6.64-6.70 (2H, m), 7.00-7.1
2 (3H, m), 7.34 (1H, psd, J = 1Hz)7- [4- (2-fluorobenzyloxy)
C) phenyl] -2-mercaptoheptanoic acid(Example compound
Object number 1-177) 1)5- [5- [4- (2-fluorobenzyloxy)
Phenyl] pentyl] h Azolidine-2,4-dione
(Exemplified Compound No. 9-101) In the same manner as in Example 44-1), 5- [5- (4-hydrido)
Roxyphenyl) pentyl] thiazolidine-2,4-di
ON 1.18 g and 2-fluorobenzyl chloride 0.7 g
To give 5- [5- [4- (2-fur
Orobenzyloxy) phenyl] pentyl] thiazolidi
1.2 g of 2,2,4-dione were obtained as a colorless solid.
(73% yield).

1 H-NMR (400 MHz, δ ppm, C
DCl ₃ ): 1.30-1.70 (6H, m), 1.85-1.95 (1H, m), 2.10-
2.20 (1H, m), 2.55 (2H, t, J = 8Hz), 4.26 (1H, dd, J = 4Hz, J =
9Hz), 5.11 (2H, s), 6.91 (2H, d, J = 8Hz), 7.05-7.15 (1H,
m), 7.08 (2H, d, J = 8Hz), 7.16 (1H, t, J = 7Hz), 7.25-7.35
(1H, m), 7.51 (1H, t, J = 7Hz), 8.09 (1H, brs) 2) 7- [4- (2 -Fluorobenzyloxy) phenyl
Le] -2 Merukaputohe heptanoic 3 acid Example 3) and in the same manner, resulting in 1) 5- [5
-[4- (2-Fluorobenzyloxy) phenyl] pentyl] thiazolidine-2,4-dione 7- [4- (2-fluorobenzyloxy) phenyl] from 1.2 g
0.67 g of -2-mercaptoheptanoic acid was obtained as a colorless solid (yield 60%).

1H-NMR (400 MHz, δ ppm, CDC
l_Three): 1.30-1.65 (6H, m), 1.65-1.80 (1H, m), 1.85-2.00 (1
H, m), 2.09 (1H, d, J = 9Hz), 2.55 (2H, t, J = 8Hz), 3.33 (1H, d
t, J = 7Hz, J = 9Hz), 5.11 (2H, s), 6.90 (2H, d, J = 8Hz), 7.05-
7.15 (1H, m), 7.08 (2H, d, J = 8Hz), 7.15 (1H, t, J = 7Hz), 7.25-
7.35 (1H, m), 7.51 (1H, t, J = 7Hz) 13C-NMR (100MHz, δppm, CDCl_Three): 27.11,
28.60, 31.35, 34.88, 35.10, 40.73, 63.72 (d, J_FC= 5.0
Hz), 114.58, 115.23 (d, J_FC= 21.6Hz), 124.15 (d, J_FC= 4.
1Hz), 124.30 (d, J_FC= 14.9Hz), 129.22, 129.48 (d, J_FC=
8.3Hz), 129.60 (d, J_FC= 4.1Hz), 134.99, 156.56, 160.2
9 (d, J_FC= 246Hz), 178.81 Example 867- [4- (3-fluorobenzyloxy)
C) phenyl] -2-mercaptoheptanoic acid(Example compound
(Article number 1-178) 1)5- [5- [4- (3-fluorobenzyloxy)
Phenyl] pentyl] h Azolidine-2,4-dione
(Exemplified Compound No. 9-102) In the same manner as in Example 44-1), 5- [5- (4-hydrido)
Roxyphenyl) pentyl] thiazolidine-2,4-di
1.84 g of ON and 1.1 g of 3-fluorobenzyl chloride
To give 5- [5- [4- (3-fluoro
Robenzyloxy) phenyl] pentyl] thiazolidine
1.6 g of -2,4-dione was obtained as a colorless solid.
(63% yield).

1 H-NMR (400 MHz, δ ppm, CDC
l ₃ ): 1.30-1.70 (6H, m), 1.85-1.95 (1H, m), 2.10-2.20
(1H, m), 2.55 (2H, t, J = 8Hz), 4.26 (1H, dd, J = 4Hz, J = 9H
z), 5.04 (2H, s), 6.88 (2H, d, J = 8Hz), 7.00 (1H, dt, J = 2H
z, J = 8Hz), 7.08 (2H, d, J = 8Hz), 7.13-7.20 (2H, m), 7.34
(1H, dt, J = 6Hz, J = 8Hz), 8.25 (1H, brs) 2) 7- [4- (3-fluorobenzyloxy) phenyl
Le] -2 Merukaputohe heptanoic 3 acid Example 3) and in the same manner, resulting in 1) 5- [5
1.1 g of 7- [4- (3-fluorobenzyloxy) phenyl] -2-mercaptoheptanoic acid was obtained from 1.42 g of-[4- (3-fluorobenzyloxy) phenyl] pentyl] thiazolidine-2,4-dione. Obtained as a colorless solid (83% yield).

1H-NMR (400 MHz, δ ppm, CDC
l_Three): 1.30-1.65 (6H, m), 1.65-1.80 (1H, m), 1.85-2.00
(1H, m), 2.09 (1H, d, J = 9Hz), 2.55 (2H, t, J = 8Hz), 3.33 (1
H, dt, J = 7Hz, J = 9Hz), 5.03 (2H, s), 6.88 (2H, d, J = 8Hz),
7.00 (1H, dt, J = 2Hz, J = 8Hz), 7.08 (2H, d, J = 8Hz), 7.13-7.
20 (2H, m), 7.34 (1H, dt, J = 6Hz, J = 8Hz) 13C-NMR (100MHz, δppm, CDCl_Three): 27.12,
28.60, 31.34, 34.87, 35.13, 40.66, 69.24 (d, J_FC= 1.7
Hz), 114.14 (d, J _FC= 22.4Hz), 114.60, 114.64 (d, J_FC= 2
1.6Hz), 122.62 (d, J_FC= 2.5Hz), 129.24, 129.99 (d, J_FC=
8.3Hz), 135.04, 139.79 (d, J_FC= 7.5Hz), 156.51, 162.8
6 (d, J_FC= 246Hz), 178.12Test example (blood glucose lowering effect) The blood glucose lowering effect in mice was tested by the following methods.

(1) Test method using ddy male mice Ddy male mice (5 to 6 weeks old) fasted for 24 hours were used. The test compound was added to distilled water together with an equimolar amount of sodium bicarbonate, and for those that did not dissolve, 1% Tween 80 was added as a suspending agent and administered orally or intravenously at a dose of 0.5 mmol / 10 ml / kg. Measurement of blood sugar level was performed 0.5, 1 and 2 hours after administration of the compound, blood was collected from 5 to 6 animals at each time point, and the blood sugar level was measured using an automatic analyzer (Hitachi Automatic Analyzer 7070, Hitachi, Ltd.). It measured using.

Table 17 shows the results of the blood glucose lowering effect test of the compound represented by the general formula (I) of the present invention.

[0429]

[Table 17] ──────────────────────────────────── Mouse blood sugar level (mg / dl) ── ──────────────── Example Administration method Suspension 0hr 0.5hr 1hr No.0.5mmol / kg ────────────────── ───────────────── 1 po. − 118.2 ± 8.9 85.0 ± 7.4 97.5 ± 5.9 2 po.− 118.6 ± 7.6 93.2 ± 7.2 105.0 ± 6.1 3 po.tween 80 122.0 ± 7.6 92.0 ± 4.3 109.0 ± 6.0 8 po.− 119.2 ± 1.1 93.0 ± 8.5 109.2 ± 6.9 9 po.− 117.3 ± 7.6 92.3 ± 5.7 107.7 ± 7.0 9 iv.− 119.0 ± 8.9 51.8 ± 8.7 72.8 ± 9.7 12 iv.− 119.0 ± 10.3 72.0 ± 8.0 87.7 ± 5.8 14 po.tween 80 121.3 ± 8.7 90.0 ± 5.2 100.7 ± 3.7 17 po.tween 80 117.0 ± 8.9 87.5 ± 6.7 100.5 ± 8.0 21 po.tween 80 117.2 ± 8.4 93.2 ± 5.5 106.3 ± 9.2 ─────────────────────────────────── po .: Oral administration, iv .: Intravenous administration Clear from the results Such, the compounds of the present invention has excellent hypoglycemic effect. (2) Spontaneous diabetes
Test method using mouse (kk-Ay) Male spontaneously diabetic mice (kk-Ay) (9 to 10 weeks old) were used. The test compound is added to distilled water together with an equimolar amount of sodium bicarbonate, and if it does not dissolve, add 1% Tween 80 as a suspending agent, or add it to distilled water without adding sodium bicarbonate and use it as a suspending agent. 0.5
% CMC, and a dose of 50 μmol / 10 ml / kg (however, in the case of the compound of Example No. 78, 20 μmol / 10 mM
l / kg. ) For 2 to 4 weeks. To measure the blood glucose level, cut the tail (about 1 mm) of the tail of a mouse, drop 2 to 3 drops of blood on a test paper for measuring glucose in blood (Tidex, MS), and use a blood glucose meter (Tide, (Manufactured by Ames).

The results of the test for the hypoglycemic effect of the compound of the present invention represented by the general formula (I) are shown in Table 18.

[0431]

[Table 18] {KK-Ay mouse blood glucose level (mg / dl)} ───────────── Example Suspension Dosage mg / kg Before administration 1st week 2nd week No. ────────────────── ──────────────── 1 − 13.6 486.7 355.0 317.2 3 tween 80 17.2 468.3 323.4 247.5 11 13.9 431.0 321.7 226.0 17 − 17.9 447.3 346.2 265.8 21 − 16.5 465.0 330.7 272.0 22 − 19.7 464.0 348.7 282.7 32 tween 80 17.3 474.0 330.7 272.0 44 tween 80 17.6 473.3 298.3 279.3 45 tween 80 17.5 504.0 312.7 249.3 46 tween 80 17.3 454.0 271.7 252.0 49 tween 80 18.0 456.0 303.3 277.7 53 tween 80 17.5 455.7 262.3 236.0 60 tween 80 17.6 473.7 342.0 243.3 63 tween 80 18.6 449.7 245.7 223.0 66 tween 80 17.3 465.3 287.3 229.3 69 tween 80 18.9 468.0 420.0 285.0 71 tween 80 18.2 524.0 297.3 269.7 72 tween 80 17.5 487.3 345.3 287.3 75 tween 80 17.2 488.0 367.0 299.3 78 CMC 7.3 496.3 441.7 391.0 よ う As evident from the results in Table 18. In addition, the compounds of the present invention have an excellent blood glucose lowering effect.

The thiazolidine compound represented by the general formula (II) was also subjected to a blood glucose lowering effect test in the same manner as described above.

As a result, the thiazolidine compound represented by the general formula (II) also showed an excellent blood glucose lowering effect. Formulation Example A drug containing the compound of the present invention as an active ingredient can be produced, for example, by the following method.

Formulation Example 1 Powder A powder is obtained by mixing 5 g of 7- (4-chlorobenzyloxyphenyl) -2-mercaptoheptanoic acid (Example 1), 895 g of lactose and 100 g of corn starch with a blender.

Formulation Example 2 Granules 7- (4-chlorobenzyloxyphenyl) -2-mercaptoheptanoic acid (Example 1) 5 g, lactose 865 g and low-substituted hydroxypropylcellulose 100 g were mixed, and then 300 g of a 10% aqueous solution of hydroxypropylcellulose was added. Knead. This is granulated using an extrusion granulator and dried to obtain a granule.

Formulation Example 3 Capsule 7- (4-Chlorobenzyloxyphenyl) -2-mercaptoheptanoic acid (Example 1) 5 g, lactose 115 g, corn starch 58 g and magnesium stearate 2 g were mixed using a V-type mixer, and then No. 3 A capsule is obtained by filling each capsule with 180 mg.

[0437]

Industrial Applicability The 2-mercaptocarboxylic acid derivative having the above general formula (I), the pharmaceutically acceptable ester thereof or the pharmaceutically acceptable salt thereof according to the present invention has an excellent insulin resistance improving property. Action, hypoglycemic action, anti-inflammatory action, immunomodulatory action, lipid peroxide production inhibitory action, PPA
It has an R-activating effect, and has diabetes, hyperlipidemia, obesity, impaired glucose tolerance, fatty liver, diabetic complications (eg, retinopathy, nephropathy, neuropathy, coronary artery disease, etc.), arteriosclerosis. Disease, cardiovascular disease (eg, ischemic heart disease, etc.), atherosclerosis or cell damage caused by ischemic heart disease (eg, brain damage caused by stroke, etc.) And preventive agents for inflammatory diseases (eg, osteoarthritis, pain, fever, rheumatoid arthritis, inflammatory bowel disease, autoimmune diseases, pancreatitis, etc.) (particularly diabetes and hyperlipidemia) and / or Useful as a therapeutic.

Further, the present invention provides a thiazolidinedione derivative compound which is useful as a synthetic intermediate for the above-mentioned novel derivative, has the above-mentioned effects, and is useful as a prophylactic and / or therapeutic agent for the above-mentioned diseases.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A61K 31/42 A61K 31/42 4C056 31/426 31/426 4C086 31/4406 31/4406 4C206 31/4458 31 / 4458 31/4465 31/4465 31/47 31/47 31/505 31/505 A61P 3/06 A61P 3/06 3/10 3/10 5/50 5/50 // C07D 213/30 C07D 213/30 213/32 213/32 215/12 215/12 239/26 239/26 261/08 261/08 277/24 277/24 307/42 307/42 307/79 307/79 333/16 333/16 (72 Inventor: Tetsuji Nuzawa, 55, Kamiichi-cho, Kamiichi-cho, Toyama Prefecture, Fuji Chemical Industry Co., Ltd. (72) Inventor: Tomokazu Sugawara, 55: Yokoho-no-ji Temple, Kamiichi-cho, Nakashinkawa-gun, Toyama Prefecture, Fuji Chemical Co., Ltd. 72) Inventor Kouei Moriguchi 55 Yokohoonji, Kamiichi-cho, Nakashinagawa-gun, Toyama Prefecture Inside Fuji Chemical Industry Co., Ltd. Fuji Takeshi 55-Family Yokohoonji, Kamiichi-cho, Nakashinkawa-gun, Toyama Prefecture F-term (in reference) 4C023 BA01 4C031 BA08 4C033 AD03 AD20 4C037 HA08 PA05 4C055 AA01 BA01 CA01 CA02 CA21 CB01 DA01 DA16 DB09 4C056 AA01 AB AE03 FA08 4C086 AA01 AA02 AA04 BA03 BA06 BB02 BC17 BC28 BC82 MA01 MA04 NA14 ZC35 4C206 AA01 AA02 AA04 JA23 MA01 MA04 NA14 ZC35

Claims (30)

[Claims] 1. A compound of the general formula (I) Wherein A is a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents α described below) or a heteroaromatic group (having 1 to 3 substituents α which will be described later) May be shown). X represents a bond, an oxygen atom, a sulfur atom, or an -NH- group. W and Y
Each independently represents a bond or a C ₁ -C ₂₀ alkylene group. However, the -WXY- group does not show a methylene group. R represents a hydrogen atom, a C ₁ -C ₆ alkanoyl group, or a C ₇ -C ₁₁ arylaminocarbonyl group (which may have 1 to 3 substituents β described later on the aryl). The substitution component α is
(i) a C ₁ -C ₂₀ alkyl group (which may have 1 to 3 substituents β described below), and (ii) a C ₂ -C ₂₀ unsaturated hydrocarbon group (a substituent β (1 to 3 may be provided.), (Iii)
C ₁ -C ₁₀ alkoxy group, (iv) halogen atom, (v) hydroxyl group,
(vi) a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents β described below), and (vii) a monocyclic heteroaromatic group (1 to 3 substituents β described later). (Vii)
i) C ₇ -C ₁₆ aralkyl group (substituted β
And may have one hydroxyl group as a substituent on the alkyl. ), (Ix) C ₇ -C ₁₆ aralkylcarbonyl group (substituted β
May be provided. ), (X) a C ₆ -C ₁₀ aryloxy group (which may have 1 to 3 substituents β described later), (xi) a C ₄ -C ₁₂ cycloalkylalkyloxy group, (xii) A C ₇ -C ₁₆ aralkyloxy group (the aryl may have 1 to 3 substituents β described later on the aryl, and the alkyl may have 1 hydroxyl group as a substituent on the alkyl);
(xiii) a C ₇ -C ₁₆ arylcarbonylalkyloxy group (which may have 1 to 3 substituents β described later on the aryl), (xiv) a monocyclic heteroaromatic ring C ₁ -C ₆ Alkyloxy group (substituent β described later on monocyclic heteroaromatic ring is 1 to 3
And the alkyl may have one hydroxyl group as a substituent on the alkyl. ), (Xv) monocyclic heteroaromatic ring C _1-
A C ₆ carbonylalkyloxy group (which may have 1 to 3 substituents β described later on the monocyclic heteroaromatic ring),
(xvi) a C ₇ -C ₁₆ aryloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), (xv
ii) a C ₈ -C ₂₂ aralkyloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), or (xviii) a C ₂ -C ₁₁ carboxyalkoxy group. The substituent β is (i) a C ₁ -C ₆ alkyl group, (ii) a C ₁ -C ₆ alkoxy group, (iii) a C ₁ -C ₆ alkylthio group, (iv) a halogen atom,
(v) C ₁ -C ₄ alkylenedioxy group, (vi) a nitro group, (vii)
Cyano group, (viii) C ₁ -C ₆ alkanoyl group, (ix) carbamoyl group, (x) C ₂ -C ₇ alkoxycarbonylamino group, or
(xi) represents a phenyl group. Or a pharmacologically acceptable ester thereof, or a pharmacologically acceptable salt thereof, for preventing or treating diabetes. 2. The method according to claim 1, wherein A is a C ₆ -C ₁₀ aryl group (which may have one or two substituents α) or a heteroaromatic ring group having one or two heteroatoms ( (Which may have one or two substituents α)) or a pharmacologically acceptable ester thereof or a pharmacologically acceptable salt thereof. An agent for preventing or treating diabetes. 3. The method according to claim 1, wherein A is a C ₆ -C ₁₀ aryl group (which may have one or two substituents α) or a heteroaromatic ring group having one heteroatom (substituents). (It may have one α.)
-An agent for preventing or treating diabetes, comprising a mercaptocarboxylic acid derivative or a pharmaceutically acceptable ester thereof or a pharmaceutically acceptable salt thereof. 4. The method according to claim 1, wherein A is a C ₆ -C ₁₀ aryl group (which may have one substituent α) or a heteroaromatic ring group having one hetero atom (wherein A 2-mercaptocarboxylic acid derivative or a pharmacologically acceptable ester thereof, or a pharmacologically acceptable salt thereof,
An agent for preventing or treating diabetes. 5. The 2-mercaptocarboxylic acid derivative according to claim 1, wherein A is a C ₆ -C ₁₀ aryl group (which may have one substituent α) or a pharmacologically acceptable derivative thereof. An agent for preventing or treating diabetes, comprising an ester or a pharmacologically acceptable salt thereof. 6. One of the first to fifth aspects.
In the item, X is a bond, or a 2-mercaptocarboxylic acid derivative represented by an oxygen atom, a pharmacologically acceptable ester thereof or a pharmacologically acceptable salt thereof, or a preventive agent for diabetes or Therapeutic agent. 7. One of the first to fifth aspects selected from the above.
In the above item, a prophylactic or therapeutic agent for diabetes, comprising a 2-mercaptocarboxylic acid derivative in which X is a bond, or a pharmaceutically acceptable ester thereof, or a pharmaceutically acceptable salt thereof. 8. One of the first to fifth aspects selected from the above.
In the above item, a preventive or therapeutic agent for diabetes, comprising a 2-mercaptocarboxylic acid derivative in which X is represented by an oxygen atom, a pharmaceutically acceptable ester thereof, or a pharmaceutically acceptable salt thereof. 9. Any one selected from claims 1 to 8
In the above item, W and Y are each independently a bond or a C ₁ -C ₁₀ alkylene group (provided that the -WXY- group does not represent a methylene group), or a 2-mercaptocarboxylic acid derivative or a drug thereof. An agent for preventing or treating diabetes, comprising a physiologically acceptable ester or a pharmacologically acceptable salt thereof. 10. The method according to claim 1, wherein W and Y are each independently a bond or a C ₁ -C ₈ alkylene group (provided that -WXY- group is a methylene group; A prophylactic or therapeutic agent for diabetes comprising a 2-mercaptocarboxylic acid derivative represented by the following formula: or a pharmacologically acceptable ester thereof or a pharmacologically acceptable salt thereof. 11. The method according to claim 1, wherein W and Y each independently represent a bond or a C ₁ -C ₆ alkylene group (provided that -WXY- is a methylene group. A prophylactic or therapeutic agent for diabetes comprising a 2-mercaptocarboxylic acid derivative represented by the following formula: or a pharmacologically acceptable ester thereof or a pharmacologically acceptable salt thereof. 12. The compound according to claim 1, wherein R is a hydrogen atom or a C ₁ -C ₄ alkanoyl group.
An agent for preventing or treating diabetes, comprising a mercaptocarboxylic acid derivative, a pharmaceutically acceptable ester thereof, or a pharmaceutically acceptable salt thereof. 13. A 2-mercaptocarboxylic acid derivative wherein R is a hydrogen atom, a pharmacologically acceptable ester thereof, or a pharmacologically acceptable ester thereof according to any one of claims 1 to 11. An agent for preventing or treating diabetes, comprising an acceptable salt. 14. A method selected from claims 1 to 13.
In the above item 1, the substitution α is (i) C₁-C_TenAlkyl group, (ii) C_Two-C_TenUnsaturated
Hydrocarbon group, (iii) C₁-C _TenAlkoxy group, (iv) halogen
Atom, (v) hydroxyl group, (vi) C₆-C_TenAryl group (substituted β is 1
You may have one. ), (Vii) a monocyclic heteroaromatic group, (v
iii) phenyl C₁-C _FourAlkyl group (substituted β on phenyl
May have 1 or 2 substituents on the alkyl
May have one hydroxyl group. ), (Ix) Pheni
Le C₁-C_FourCarbonylalkyl group (substituted β on phenyl
It may have one or two. ), (X) phenoxy group
(Even if phenyl has one or two substituents β
Good. ), (Xi) C₆-C_TenCycloalkylalkyloxy
Group, (xii) phenyl C₁-C₆Alkyloxy group (on phenyl
May have one or two substituents β,
May have one hydroxyl group as a substituent on the
No. ), (Xiii) phenyl C₁-C₆Carbonylalkyloxy
Group (having one or two substituents β on phenyl
Is also good. ), (Xiv) a unit having one or two heteroatoms
Cyclic heteroaromatic ring C₁-C₆Alkyloxy group (monocyclic heteroaromatic
May have one or two substituents β on the ring,
May have one hydroxyl group as a substituent on the alkyl.
No. ), (Xv) monocyclic having one or two heteroatoms
Heteroaromatic ring C₁-C₆Carbonylalkyloxy group (monocyclic
May have one or two substituents β on the aromatic ring.
No. ), (Xvi) phenoxy C₁-C₆Alkyl group (on phenyl
May have one substitution β. ), (Xvii) phenyl C
₁-C₆Alkyloxy C₁-C₆Alkyl group (substituted on phenyl
May have one component β. ) Or (xviii) C_Two-C₇Mosquito
2-mercaptocarbo represented by ruboxoxyalkoxy group
Acid derivatives or pharmacologically acceptable esters thereof
Or diabetes containing a pharmacologically acceptable salt thereof.
Prophylactic or therapeutic agents. 15. The method according to claim 1, wherein the substituent α is (i) a C ₁ -C ₆ alkyl group, (ii) a C ₁ -C ₈ alkoxy group, (iii) Halogen atom, (iv) hydroxyl group, (v) phenyl group
(May have one substituent β), (vi) phenyl C ₁
-C ₄ alkyl group (may have one substituent β on phenyl, and may have one hydroxyl group as substituent on alkyl), (vii) phenyl C ₁ -C ₄ Carbonylalkyl group (may have one substituent β on phenyl), (viii) phenoxy group (may have one substituent β), (ix) C ₆ -C ₁₀ cycloalkylalkyloxy group, (x) phenyl C ₁ -C ₆ alkyloxy group (may have one or two substituents β on phenyl, and one hydroxyl group as a substituent on alkyl May be.),
(xi) a phenyl C ₁ -C ₆ carbonylalkyloxy group (which may have one or two substituents β on the phenyl); (xii) a monocyclic heteroaromatic having one or two heteroatoms A ring C ₁ -C ₄ alkyloxy group (the monocyclic heteroaromatic ring may have one or two substituents β, and the alkyl may have one hydroxyl group as a substituent. ), (Xiii) a monocyclic heteroaromatic ring carbonyl C ₁ -C ₄ alkyloxy group having one or two heteroatoms (even if one or two substituents β are present on the monocyclic heteroaromatic ring) (Xiv) phenoxy C ₁ -C ₄ alkyl group, (xv) phenyl C ₁ -C ₄ alkyloxy C ₁ -C ₄ alkyl group, or (xvi) C
Containing ₂ -C ₅ carboxyalkoxy 2-mercapto carboxylic acid derivative or its pharmacologically acceptable esters or acceptable salt thereof pharmacologically represented by group,
An agent for preventing or treating diabetes. 16. Any one selected from claims 1 to 13
In the above item 1, the substitution α is (i) C₁-C_FourAlkyl group, (ii) C₁-C₆Alkoki
(Iii) halogen atom, (iv) hydroxyl group, (v) phenyl
Group, (vi) phenyl C₁-C_FourAlkyl group (substituted on alkyl
May have one hydroxyl group. ), (Vii) Pheni
Le C₁-C_FourCarbonylalkyl group, (viii) phenoxy group,
(ix) C₆-C_TenCycloalkylalkyloxy group, (x)
Nil C₁-C_FourAlkyloxy group (substituted β on phenyl
Hydroxyl group as a substituent on the alkyl
May be provided. ), (Xi) phenyl C₁-C_FourCarbo
Nylalkyloxy group (has one substituent β on phenyl
It may be. ), (Xii) 1 or 2 heteroatoms
Having a monocyclic heteroaromatic ring C₁-C _FourAlkyloxy group (monocyclic
Even if the heteroaromatic ring has one or two substituents β
Often has one hydroxyl group as a substituent on alkyl
You may. ), (Xiii) having one or two heteroatoms
Monocyclic heteroaromatic carbonyl C₁-C_FourAlkyloxy group
(Having one or two substituents β on a monocyclic heteroaromatic ring)
May be. ), (Xiv) phenyl C₁-C_FourAlkyloxy C
₁-C_FourAlkyl group, or (xv) C_Two-C_FiveCarboxyalkoxy
A 2-mercaptocarboxylic acid derivative represented by a group
Its pharmaceutically acceptable esters or their pharmacology
A prophylactic or therapeutic agent for diabetes, comprising a pharmaceutically acceptable salt
Agent. 17. The method according to claim 1, wherein the substitution α is (i) a C ₁ -C ₂ alkyl group, (ii) a C ₁ -C ₆ alkoxy group, (iii) Chlorine atom, (iv) hydroxyl group, (v) phenyl C ₁ -C ₄
An alkyl group (which may have one hydroxyl group as a substituent on the alkyl), (vi) a phenyl C ₁ -C ₄ carbonylalkyl group, and (vii) a phenyl C ₁ -C ₄ alkyloxy group (on the phenyl May have one substituent β, and the alkyl may have one hydroxyl group as a substituent.), (Vii
i) a phenyl C ₁ -C ₄ carbonylalkyloxy group, or (i
x) a monocyclic heteroaromatic ring having one or two heteroatoms
C ₁ -C ₄ alkyloxy group (substituted β on a monocyclic heteroaromatic ring
May be provided. Or a pharmacologically acceptable ester thereof, or a pharmacologically acceptable salt thereof, for preventing or treating diabetes. 18. The method according to claim 1, wherein the substituent α is (i) a phenyl C ₁ -C ₄ alkyloxy group (having one substituent β on phenyl). And may have one hydroxyl group as a substituent on the alkyl.), (I
i) a phenyl C ₁ -C ₄ carbonylalkyloxy group, or (ii)
i) monocyclic heteroaromatic ring having one or two heteroatoms
C ₁ -C ₄ alkyloxy group (substituted β on a monocyclic heteroaromatic ring
May be provided. Or a pharmacologically acceptable ester thereof, or a pharmacologically acceptable salt thereof, for preventing or treating diabetes. 19. The method according to claim 1, wherein the substituent β is (i) a C ₁ -C ₆ alkyl group, (ii) a C ₁ -C ₆ alkoxy group, (iii) 2-mercaptocarboxylic acid derivative represented by a halogen atom, (iv) nitro group, (v) cyano group, or (vi) phenyl group or a pharmaceutically acceptable ester thereof, or a pharmaceutically acceptable ester thereof A preventive or therapeutic agent for diabetes containing a salt. 20. The method according to any one of claims 1 to 18, wherein the substituent β is (i) a C ₁ -C ₄ alkyl group, (ii) a C ₁ -C ₄ alkoxy group, (iii) A preventive or therapeutic agent for diabetes comprising a halogen atom or (iv) a 2-mercaptocarboxylic acid derivative represented by a phenyl group, a pharmaceutically acceptable ester thereof, or a pharmaceutically acceptable salt thereof. . 21. The method according to any one of claims 1 to 18, wherein the substituent β is (i) a C ₁ -C ₂ alkyl group, (ii) a C ₁ -C ₂ alkoxy group, or (iii) ) Containing a 2-mercaptocarboxylic acid derivative represented by a halogen atom, a pharmaceutically acceptable ester thereof, or a pharmaceutically acceptable salt thereof,
An agent for preventing or treating diabetes. 22. The method according to claim 1, wherein A is C₆-C_TenAryl group (has one or two substituents α)
It may be. ) Or one or two heteroatoms
A heteroaromatic group (having one or two substituents α)
You may. X is a bond, an oxygen atom or a sulfur
An atom; W and Y each independently represent a bond or
C₁-C_TenAlkylene group (however, -W-X-Y- group represents a methylene group
Not. R represents a hydrogen atom or C₁-C_FourArca
A substituted group α is represented by (i) C₁-C_TenAlkyl group,
(ii) C_Two-C_TenUnsaturated hydrocarbon group, (iii) C₁-C _TenAlkoxy
Group, (iv) halogen atom, (v) hydroxyl group, (vi) C₆-C_TenAlly
Group (may have one substituent β), (vii) a monocyclic ring
Formula heteroaromatic group, (viii) phenyl C₁-C _FourAlkyl group (Fe
May have one or two substituents β on the nil,
It may have one hydroxyl group as a substituent on alkyl.
No. ), (Ix) phenyl C₁-C_FourCarbonylalkyl group (Fe
May have one or two substituents β on the phenyl.
No. ), (X) phenoxy group (substitute β
Or it may have two. ), (Xi) C₆-C_TenCycloa
Alkylalkyloxy group, (xii) phenyl C₁-C₆Alkyl
An oxy group (having one or two substituents β on phenyl
May be substituted with one hydroxyl group on the alkyl.
You may have. ), (Xiii) phenyl C₁-C ₆Carboni
Alkyloxy group (substitute β on phenyl
May have two. ), (Xiv) one heteroatom
Or two monocyclic heteroaromatic rings C₁-C₆Alkyloxy
Group (having one or two substituents β on a monocyclic heteroaromatic ring)
And a hydroxyl group may be substituted on the alkyl by one.
You may have one. ), (Xv) one or more heteroatoms
Monocyclic heteroaromatic ring C having two₁-C₆Carbonylalkyl
An oxy group (substituted β on the monocyclic heteroaromatic ring is 1 or
You may have two. ), (Xvi) phenoxy C₁-C₆Al
A kill group (may have one substituent β on phenyl
No. ), (Xvii) phenyl C₁-C₆Alkyloxy C₁-C₆Al
A kill group (may have one substituent β on phenyl
No. ) Or (xviii) C_Two-C₇Represents a carboxyalkoxy group
And the substitution β is (i) C₁-C₆Alkyl group, (ii) C₁-C₆Al
Coxy group, (iii) halogen atom, (iv) nitro group, (v) shea
2-mercaptoka represented by a phenyl group or (vi) a phenyl group
Rubonic acid derivatives or pharmaceutically acceptable esthetics
Containing sugars or pharmacologically acceptable salts thereof.
An agent for preventing or treating urine. 23. The method according to claim 1, wherein A is C₆-C_TenAryl group (has one or two substituents α)
It may be. ) Or heteroaryl having one heteroatom
An aromatic ring group (which may have one substituent α); X
Represents a bond or an oxygen atom; W and Y represent
Independent bond or C₁-C₈Alkylene group (however, -W-X-Y
The group does not represent a methylene group. R is a hydrogen atom
And the substitution α is (i) C₁-C_FourAlkyl group, (ii) C₁-C₆
Alkoxy group, (iii) halogen atom, (iv) hydroxyl group, (v)
Phenyl group, (vi) phenyl C₁-C_FourAn alkyl group (on the alkyl
It may have one hydroxyl group as a substituent. ), (Vii)
 Phenyl C₁-C_FourCarbonylalkyl group, (viii) phenoxy
Group, (ix) C₆-C_TenCycloalkylalkyloxy group,
(x) phenyl C₁-C_FourAlkyloxy group (substituted on phenyl
May have one moiety β, which is substituted on the alkyl.
May have one hydroxyl group. ), (Xi) phenyl C₁-
C_FourCarbonylalkyloxy group (substituted β on phenyl
May be provided. ), (Xii) one heteroatom
Or two monocyclic heteroaromatic rings C₁-C _FourAlkyloxy
Group (having one or two substituents β on a monocyclic heteroaromatic ring)
And a hydroxyl group may be substituted on the alkyl by one.
You may have one. ), (Xiii) one heteroatom
Is two monocyclic heteroaromatic carbonyl C₁-C_FourArchi
A luoxy group (with one or more substituents β on the monocyclic heteroaromatic ring)
May have two. ), (Xiv) phenyl C₁-C_FourAl
Killoxy C₁-C_FourAlkyl group, or (xv) C_Two-C_FiveCarboxy
Represents an alkoxy group; the substituent β is represented by (i) C₁-C_FourAlkyl
Group, (ii) C₁-C_FourAn alkoxy group, (iii) a halogen atom, or
(iv) 2-mercaptocarboxylic acid derivative represented by phenyl group
Conductors or their pharmacologically acceptable esters or
Prevent diabetes, containing these pharmacologically acceptable salts
Agent or therapeutic agent. 24. The method according to claim 1, wherein A represents a C ₆ -C ₁₀ aryl group (which may have one substituent α); X represents a bond; Each independently a bond or a C ₁ -C ₆ alkylene group (provided that -WX
The -Y- group does not show a methylene group. R represents a hydrogen atom; and the substituent α is (i) a phenyl C ₁ -C ₄ alkyloxy group (which may have one substituent β on phenyl;
The alkyl may have one hydroxyl group as a substituent. ), (Ii) a phenyl C ₁ -C ₄ carbonylalkyloxy group, or (iii) a monocyclic heteroaromatic ring C ₁ -C ₄ alkyloxy group having one or two heteroatoms (on a monocyclic heteroaromatic ring May have one substituent β)); the substituent β is (i) a C ₁ -C ₂ alkyl group, (ii) a C ₁ -C ₂ alkoxy group, or (iii) halogen An agent for preventing or treating diabetes, comprising a 2-mercaptocarboxylic acid derivative represented by an atom, a pharmacologically acceptable ester thereof, or a pharmacologically acceptable salt thereof. 25. The method according to claim 1, wherein A is an aryl group having 6 to 10 carbon atoms which may have 1 to 3 substituents α described below or 1 to 3 substituents α described later. A heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom,
X represents a bond, an oxygen atom, a sulfur atom, or a —NH— group, and W and Y each independently represent a bond or a linear or branched chain Represents an alkylene group having 1 to 20 carbon atoms, provided that -WXY- does not represent a methylene group. R represents a hydrogen atom, an alkanoyl group having 1 to 6 carbon atoms, or a carbon atom having 6 to 6 carbon atoms which may have 1 to 3 substituents β described later.
Represents an arylaminocarbonyl group having an aryl having from 1 to 10; and the substituent α is (i) a straight chain which may have 1 to 3 substituents β (excluding an alkyl group) described later. A branched or branched alkyl group having 1 to 20 carbon atoms, (i
i) a straight or branched chain having 2 to 20 carbon atoms which may have 1 to 3 substituents β (excluding an alkyl group) to be described later and having 1 to 3 carbon atoms; Unsaturated hydrocarbon group having a double bond, (iii) linear or branched alkoxy group having 1 to 10 carbon atoms, (iv) halogen atom, (v) hydroxyl group, (vi) An aryl group having 6 to 10 carbon atoms which may have 1 to 3 substituents β, and (vii) 1 to 3 hetero atoms selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. A 5- or 6-membered monocyclic heteroaromatic group, (viii) an aryl having 6 to 10 carbon atoms which may have 1 to 3 substituents β described later, and one hydroxyl group as a substituent. An aralkyl group having a linear or branched alkyl having 1 to 6 carbon atoms which may be substituted, (ix A) an aryloxy group having 6 to 10 carbon atoms which may have 1 to 3 substituents β described later, (x) a cycloalkyl having 3 to 6 carbon atoms, and a linear or branched chain A cycloalkylalkyloxy group having an alkyl having 1 to 6 carbon atoms, (xi) an aryl having 6 to 10 carbon atoms optionally having 1 to 3 substituents β described later, and a straight chain An aralkyloxy group having an alkyl having 1 to 6 carbon atoms in a branched or branched chain, (xii) 5 or 5 having 1 to 3 hetero atoms selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom A 6-membered monocyclic heteroaromatic ring and a linear or branched monocyclic heteroaromatic alkyloxy group having an alkyl having 1 to 6 carbon atoms; Number of carbon atoms that three may have An aryloxyalkyl group having an aryl having 6 to 10 and an alkyl having a linear or branched alkyl having 1 to 6 carbon atoms, and (xiv) having 1 to 3 substituents β described later. 6 to 1 carbon atoms
An aryl having 0 and a linear or branched alkyl having 1 to 6 carbon atoms are each independently 2
Aralkyloxyalkyl group, or (xv) aryl having 6 to 10 carbon atoms which may have 1 to 3 substituents β to be described later, and linear or branched C1 to Represents an arylalkylcarbonyl group having an alkyl having 6; and the substituent β is (i) a linear or branched alkyl group having 1 to 6 carbon atoms; (ii) a linear or branched alkyl group. A branched alkoxy group having 1 to 6 carbon atoms, (iii) a linear or branched alkylthio group having 1 to 6 carbon atoms, (iv) a halogen atom, and (v) a carbon atom having 1 carbon atom. Alkylenedioxy group having from 4 to 4, (vi) nitro group, (vii)
Alkoxycarbonylamino having a cyano group, (viii) an alkanoyl group having 1 to 6 carbon atoms, (ix) a carbamoyl group, or (x) a linear or branched alkoxy having 1 to 6 carbon atoms A preventive or therapeutic agent for diabetes comprising a 2-mercaptocarboxylic acid derivative represented by the formula: or a pharmacologically acceptable ester thereof or a pharmacologically acceptable salt thereof. 26. A compound of the general formula (I) Wherein A is a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents α described below) or a heteroaromatic group (having 1 to 3 substituents α which will be described later) May be shown). X represents a bond, an oxygen atom, a sulfur atom, or an -NH- group. W and Y
Each independently represents a bond or a C ₁ -C ₂₀ alkylene group. However, the -WXY- group does not show a methylene group. R represents a hydrogen atom, a C ₁ -C ₆ alkanoyl group, or a C ₇ -C ₁₁ arylaminocarbonyl group (which may have 1 to 3 substituents β described later on the aryl). The substitution component α is
(i) a C ₁ -C ₂₀ alkyl group (which may have 1 to 3 substituents β described below), and (ii) a C ₂ -C ₂₀ unsaturated hydrocarbon group (a substituent β (1 to 3 may be provided.), (Iii)
C ₁ -C ₁₀ alkoxy group, (iv) halogen atom, (v) hydroxyl group,
(vi) a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents β described below), and (vii) a monocyclic heteroaromatic group (1 to 3 substituents β described later). (Vii)
i) C ₇ -C ₁₆ aralkyl group (substituted β
And may have one hydroxyl group as a substituent on the alkyl. ), (Ix) C ₇ -C ₁₆ aralkylcarbonyl group (substituted β
May be provided. ), (X) a C ₆ -C ₁₀ aryloxy group (which may have 1 to 3 substituents β described later), (xi) a C ₄ -C ₁₂ cycloalkylalkyloxy group, (xii) A C ₇ -C ₁₆ aralkyloxy group (the aryl may have 1 to 3 substituents β described later on the aryl, and the alkyl may have 1 hydroxyl group as a substituent on the alkyl);
(xiii) a C ₇ -C ₁₆ arylcarbonylalkyloxy group (which may have 1 to 3 substituents β described later on the aryl), (xiv) a monocyclic heteroaromatic ring C ₁ -C ₆ Alkyloxy group (substituent β described later on monocyclic heteroaromatic ring is 1 to 3
And the alkyl may have one hydroxyl group as a substituent on the alkyl. ), (Xv) monocyclic heteroaromatic ring C _1-
A C ₆ carbonylalkyloxy group (which may have 1 to 3 substituents β described later on the monocyclic heteroaromatic ring),
(xvi) a C ₇ -C ₁₆ aryloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), (xv
ii) a C ₈ -C ₂₂ aralkyloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), or (xviii) a C ₂ -C ₁₁ carboxyalkoxy group. The substituent β is (i) a C ₁ -C ₆ alkyl group, (ii) a C ₁ -C ₆ alkoxy group, (iii) a C ₁ -C ₆ alkylthio group, (iv) a halogen atom,
(v) C ₁ -C ₄ alkylenedioxy group, (vi) a nitro group, (vii)
Cyano group, (viii) C ₁ -C ₆ alkanoyl group, (ix) carbamoyl group, (x) C ₂ -C ₇ alkoxycarbonylamino group, or
(xi) represents a phenyl group. Or a pharmacologically acceptable ester thereof, or a pharmacologically acceptable salt thereof, comprising a prophylactic or therapeutic agent for hyperlipidemia. 27. A compound of the general formula (I) Wherein A is a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents α described below) or a heteroaromatic group (having 1 to 3 substituents α which will be described later) May be shown). X represents a bond, an oxygen atom, a sulfur atom, or an -NH- group. W and Y
Each independently represents a bond or a C ₁ -C ₂₀ alkylene group. However, the -WXY- group does not show a methylene group. R represents a hydrogen atom, a C ₁ -C ₆ alkanoyl group, or a C ₇ -C ₁₁ arylaminocarbonyl group (which may have 1 to 3 substituents β described later on the aryl). The substitution component α is
(i) a C ₁ -C ₂₀ alkyl group (which may have 1 to 3 substituents β described below), and (ii) a C ₂ -C ₂₀ unsaturated hydrocarbon group (a substituent β (1 to 3 may be provided.), (Iii)
C ₁ -C ₁₀ alkoxy group, (iv) halogen atom, (v) hydroxyl group,
(vi) a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents β described below), and (vii) a monocyclic heteroaromatic group (1 to 3 substituents β described later). (Vii)
i) C ₇ -C ₁₆ aralkyl group (substituted β
And may have one hydroxyl group as a substituent on the alkyl. ), (Ix) C ₇ -C ₁₆ aralkylcarbonyl group (substituted β
May be provided. ), (X) a C ₆ -C ₁₀ aryloxy group (which may have 1 to 3 substituents β described later), (xi) a C ₄ -C ₁₂ cycloalkylalkyloxy group, (xii) A C ₇ -C ₁₆ aralkyloxy group (the aryl may have 1 to 3 substituents β described later on the aryl, and the alkyl may have 1 hydroxyl group as a substituent on the alkyl);
(xiii) a C ₇ -C ₁₆ arylcarbonylalkyloxy group (which may have 1 to 3 substituents β described later on the aryl), (xiv) a monocyclic heteroaromatic ring C ₁ -C ₆ Alkyloxy group (substituent β described later on monocyclic heteroaromatic ring is 1 to 3
And the alkyl may have one hydroxyl group as a substituent on the alkyl. ), (Xv) monocyclic heteroaromatic ring C _1-
A C ₆ carbonylalkyloxy group (which may have 1 to 3 substituents β described later on the monocyclic heteroaromatic ring),
(xvi) a C ₇ -C ₁₆ aryloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), (xv
ii) a C ₈ -C ₂₂ aralkyloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), or (xviii) a C ₂ -C ₁₁ carboxyalkoxy group. The substituent β is (i) a C ₁ -C ₆ alkyl group, (ii) a C ₁ -C ₆ alkoxy group, (iii) a C ₁ -C ₆ alkylthio group, (iv) a halogen atom,
(v) C ₁ -C ₄ alkylenedioxy group, (vi) a nitro group, (vii)
Cyano group, (viii) C ₁ -C ₆ alkanoyl group, (ix) carbamoyl group, (x) C ₂ -C ₇ alkoxycarbonylamino group, or
(xi) represents a phenyl group. And a pharmacologically acceptable ester thereof or a pharmacologically acceptable salt thereof. 28. The compound of the general formula (I) Wherein A is a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents α described below) or a heteroaromatic group (having 1 to 3 substituents α which will be described later) May be shown). X represents a bond, an oxygen atom, a sulfur atom, or an -NH- group. W and Y
Each independently represents a bond or a C ₁ -C ₂₀ alkylene group. However, the -WXY- group does not show a methylene group. R represents a hydrogen atom, a C ₁ -C ₆ alkanoyl group, or a C ₇ -C ₁₁ arylaminocarbonyl group (which may have 1 to 3 substituents β described later on the aryl). The substitution component α is
(i) a C ₁ -C ₂₀ alkyl group (which may have 1 to 3 substituents β described below), and (ii) a C ₂ -C ₂₀ unsaturated hydrocarbon group (a substituent β (1 to 3 may be provided.), (Iii)
C ₁ -C ₁₀ alkoxy group, (iv) halogen atom, (v) hydroxyl group,
(vi) a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents β described below), and (vii) a monocyclic heteroaromatic group (1 to 3 substituents β described later). (Vii)
i) C ₇ -C ₁₆ aralkyl group (substituted β
And may have one hydroxyl group as a substituent on the alkyl. ), (Ix) C ₇ -C ₁₆ aralkylcarbonyl group (substituted β
May be provided. ), (X) a C ₆ -C ₁₀ aryloxy group (which may have 1 to 3 substituents β described later), (xi) a C ₄ -C ₁₂ cycloalkylalkyloxy group, (xii) A C ₇ -C ₁₆ aralkyloxy group (the aryl may have 1 to 3 substituents β described later on the aryl, and the alkyl may have 1 hydroxyl group as a substituent on the alkyl);
(xiii) a C ₇ -C ₁₆ arylcarbonylalkyloxy group (which may have 1 to 3 substituents β described later on the aryl), (xiv) a monocyclic heteroaromatic ring C ₁ -C ₆ Alkyloxy group (substituent β described later on monocyclic heteroaromatic ring is 1 to 3
And the alkyl may have one hydroxyl group as a substituent on the alkyl. ), (Xv) monocyclic heteroaromatic ring C _1-
A C ₆ carbonylalkyloxy group (which may have 1 to 3 substituents β described later on the monocyclic heteroaromatic ring),
(xvi) a C ₇ -C ₁₆ aryloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), (xv
ii) a C ₈ -C ₂₂ aralkyloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), or (xviii) a C ₂ -C ₁₁ carboxyalkoxy group. The substituent β is (i) a C ₁ -C ₆ alkyl group, (ii) a C ₁ -C ₆ alkoxy group, (iii) a C ₁ -C ₆ alkylthio group, (iv) a halogen atom,
(v) C ₁ -C ₄ alkylenedioxy group, (vi) a nitro group, (vii)
Cyano group, (viii) C ₁ -C ₆ alkanoyl group, (ix) carbamoyl group, (x) C ₂ -C ₇ alkoxycarbonylamino group, or
(xi) represents a phenyl group. A hypoglycemic agent comprising a 2-mercaptocarboxylic acid derivative represented by the formula (I) or a pharmaceutically acceptable ester thereof or a pharmaceutically acceptable salt thereof. 29. A compound of the formula (I) for producing a medicament for preventing or treating diabetes. Wherein A is a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents α described below) or a heteroaromatic group (having 1 to 3 substituents α which will be described later) May be shown). X represents a bond, an oxygen atom, a sulfur atom, or an -NH- group. W and Y
Each independently represents a bond or a C ₁ -C ₂₀ alkylene group. However, the -WXY- group does not show a methylene group. R represents a hydrogen atom, a C ₁ -C ₆ alkanoyl group, or a C ₇ -C ₁₁ arylaminocarbonyl group (which may have 1 to 3 substituents β described later on the aryl). The substitution component α is
(i) a C ₁ -C ₂₀ alkyl group (which may have 1 to 3 substituents β described below), and (ii) a C ₂ -C ₂₀ unsaturated hydrocarbon group (a substituent β (1 to 3 may be provided.), (Iii)
C ₁ -C ₁₀ alkoxy group, (iv) halogen atom, (v) hydroxyl group,
(vi) a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents β described below), and (vii) a monocyclic heteroaromatic group (1 to 3 substituents β described later). (Vii)
i) C ₇ -C ₁₆ aralkyl group (substituted β
And may have one hydroxyl group as a substituent on the alkyl. ), (Ix) C ₇ -C ₁₆ aralkylcarbonyl group (substituted β
May be provided. ), (X) a C ₆ -C ₁₀ aryloxy group (which may have 1 to 3 substituents β described later), (xi) a C ₄ -C ₁₂ cycloalkylalkyloxy group, (xii) A C ₇ -C ₁₆ aralkyloxy group (the aryl may have 1 to 3 substituents β described later on the aryl, and the alkyl may have 1 hydroxyl group as a substituent on the alkyl);
(xiii) a C ₇ -C ₁₆ arylcarbonylalkyloxy group (which may have 1 to 3 substituents β described later on the aryl), (xiv) a monocyclic heteroaromatic ring C ₁ -C ₆ Alkyloxy group (substituent β described later on monocyclic heteroaromatic ring is 1 to 3
And the alkyl may have one hydroxyl group as a substituent on the alkyl. ), (Xv) monocyclic heteroaromatic ring C _1-
A C ₆ carbonylalkyloxy group (which may have 1 to 3 substituents β described later on the monocyclic heteroaromatic ring),
(xvi) a C ₇ -C ₁₆ aryloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), (xv
ii) a C ₈ -C ₂₂ aralkyloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), or (xviii) a C ₂ -C ₁₁ carboxyalkoxy group. The substituent β is (i) a C ₁ -C ₆ alkyl group, (ii) a C ₁ -C ₆ alkoxy group, (iii) a C ₁ -C ₆ alkylthio group, (iv) a halogen atom,
(v) C ₁ -C ₄ alkylenedioxy group, (vi) a nitro group, (vii)
Cyano group, (viii) C ₁ -C ₆ alkanoyl group, (ix) carbamoyl group, (x) C ₂ -C ₇ alkoxycarbonylamino group, or
(xi) represents a phenyl group. Use of a 2-mercaptocarboxylic acid derivative or a pharmaceutically acceptable ester thereof or a pharmaceutically acceptable salt thereof represented by the formula: (30) A compound of the formula (I) Wherein A is a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents α described below) or a heteroaromatic group (having 1 to 3 substituents α which will be described later) May be shown). X represents a bond, an oxygen atom, a sulfur atom, or an -NH- group. W and Y
Each independently represents a bond or a C ₁ -C ₂₀ alkylene group. However, the -WXY- group does not show a methylene group. R represents a hydrogen atom, a C ₁ -C ₆ alkanoyl group, or a C ₇ -C ₁₁ arylaminocarbonyl group (which may have 1 to 3 substituents β described later on the aryl). The substitution component α is
(i) a C ₁ -C ₂₀ alkyl group (which may have 1 to 3 substituents β described below), and (ii) a C ₂ -C ₂₀ unsaturated hydrocarbon group (a substituent β (1 to 3 may be provided.), (Iii)
C ₁ -C ₁₀ alkoxy group, (iv) halogen atom, (v) hydroxyl group,
(vi) a C ₆ -C ₁₀ aryl group (which may have 1 to 3 substituents β described below), and (vii) a monocyclic heteroaromatic group (1 to 3 substituents β described later). (Vii)
i) C ₇ -C ₁₆ aralkyl group (substituted β
And may have one hydroxyl group as a substituent on the alkyl. ), (Ix) C ₇ -C ₁₆ aralkylcarbonyl group (substituted β
May be provided. ), (X) a C ₆ -C ₁₀ aryloxy group (which may have 1 to 3 substituents β described later), (xi) a C ₄ -C ₁₂ cycloalkylalkyloxy group, (xii) A C ₇ -C ₁₆ aralkyloxy group (the aryl may have 1 to 3 substituents β described later on the aryl, and the alkyl may have 1 hydroxyl group as a substituent on the alkyl);
(xiii) a C ₇ -C ₁₆ arylcarbonylalkyloxy group (which may have 1 to 3 substituents β described later on the aryl), (xiv) a monocyclic heteroaromatic ring C ₁ -C ₆ Alkyloxy group (substituent β described later on monocyclic heteroaromatic ring is 1 to 3
And the alkyl may have one hydroxyl group as a substituent on the alkyl. ), (Xv) monocyclic heteroaromatic ring C _1-
A C ₆ carbonylalkyloxy group (which may have 1 to 3 substituents β described later on the monocyclic heteroaromatic ring),
(xvi) a C ₇ -C ₁₆ aryloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), (xv
ii) a C ₈ -C ₂₂ aralkyloxyalkyl group (which may have 1 to 3 substituents β described later on the aryl), or (xviii) a C ₂ -C ₁₁ carboxyalkoxy group. The substituent β is (i) a C ₁ -C ₆ alkyl group, (ii) a C ₁ -C ₆ alkoxy group, (iii) a C ₁ -C ₆ alkylthio group, (iv) a halogen atom,
(v) C ₁ -C ₄ alkylenedioxy group, (vi) a nitro group, (vii)
Cyano group, (viii) C ₁ -C ₆ alkanoyl group, (ix) carbamoyl group, (x) C ₂ -C ₇ alkoxycarbonylamino group, or
(xi) represents a phenyl group. A method for preventing or treating diabetes, comprising administering to a human a pharmacologically effective amount of a 2-mercaptocarboxylic acid derivative or a pharmacologically acceptable ester thereof or a pharmacologically acceptable salt thereof represented by the formula: .