JPH11193272A - Medicine containing phenylalkylcarboxylic acid derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject medicine capable of developing excellent improving actions on insulin resistance, etc., useful for preventing and treating diabetic, hyperlipemia, etc., by including a new phenylalkylcarboxylic acid derivative. SOLUTION: This medicine comprises a phenylakylcarboxylic acid derivative of formula I (R<1> is H, 1-6C straight-chain or branched alkyl; R<2> is a 2-6C straight-chain or branched alkylene; R<3> is H, a 1-6C straight-chain or branched alkyl or the like; Z is a single bond or the like; W is a 1-6C straight-chain or branched alkyl, hydroxyl or the like; X is a 6-10C aryl which may contain a specific substituent component or the like; Y is a hydrogen atom, a sulfur atom or the like) as an active ingredient. For example, 2-ethoxy-3-[4-[2-[[1-[4[(2- pyridyl)phenyl]ethylidene]aminoxy]ethoxy]phenyl]propionic acid may be cited as the derivative of formula I and is obtained by reacting a compound of formula II (U is a hydroxyl group or the like) with a compound of formula III (W<1> is a protected amino group or the like) and removing the ester residue.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to an excellent insulin resistance improving action, an anti-inflammatory action, an immunomodulatory action, an aldose reductase inhibitory action, a 5-lipoxygenase inhibitory action,
The present invention relates to a medicament containing a phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof, which has a lipid peroxide production-suppressing action, a PPAR activating action, and an anti-osteoporosis action.

Further, the present invention provides a diabetic, hyperlipidemia, obesity, impaired glucose tolerance comprising the above phenylalkylcarboxylic acid derivative, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable ester thereof as an active ingredient. (Impaired glucose
tolerance: IGT), insulin resistant non-IGT (NGT), hypertension, fatty liver, diabetic complications (eg retinopathy, nephropathy, neuropathy, cataract, coronary artery disease, etc.), arteries Sclerosis, gestational diabetes (gestat
ional diabetes mellitus: GDM), polycystic ovary syndrome (PCOS), cardiovascular disease (eg, ischemic heart disease), atherosclerosis or cell damage caused by ischemic heart disease (eg, Diseases mainly due to insulin resistance, such as brain injury caused by stroke); osteoarthritis, pain, fever, rheumatoid arthritis, inflammatory bowel disease, acne, sunburn, psoriasis,
The present invention relates to a preventive and / or therapeutic agent for eczema, allergic disease, asthma, GI ulcer, cancer, cachexia, autoimmune disease, and inflammatory disease such as pancreatitis; osteoporosis; cataract and the like.

[0003]

2. Description of the Related Art Conventionally, as an agent for treating diabetes and hyperglycemia,
Insulin and sulfonylurea compounds such as tributamide and glipizide have been used. Recently, phenylalkylcarboxylic acid derivatives have been reported as drugs for treating insulin-independent diabetes. Examples of these compounds include: (1-1) 3- [4- [2- (5-methyl-2-phenyl-4-oxazolyl) ethoxy] phenyl] -2-
(Acetylthio) propionic acid and its ester, 2
-Methoxy-3- [4- [2- (5-methyl-2-phenyl-4-oxazolyl) ethoxy] phenyl] propionic acid, 3-[[4- (4-benzyloxyphenyl) ethoxy] phenyl] -2 -Methoxypropionic acid, 2-phenoxy-3- [4- (2-phenyl) ethoxyphenyl] propionic acid and the like are described in WO91 / 197.
International Publication No. 02 (= Special Publication No. 5-507920)
No.).

(1-2) 3- [4- [2- [N- (2
-Benzoxazolyl) -N-methylamino] ethoxy] phenyl] -2-((N-ethyl-N-phenyl)
Amino) propionic acid and its esters are WO
It is described in WO 94/29285.

(1-3) 3- [4- [2- [N- (2
-Benzoxazolyl) -N-methylamino] ethoxy] phenyl] -2-pyrrolepropionic acid and its esters are described in WO 94/29302.

(1-4) 3- [4- [2- [N- (2
-Benzoxazolyl) -N-methylamino] ethoxy] phenyl] -2- (propyl) propionic acid and its esters, 3- [4- [2- [N- (2-benzoxazolyl) -N- Methylamino] ethoxy] phenyl] -2- (3-phenylpropyl) propionic acid and its ester, 3- [4- [2- [N- (2-benzoxazolyl) -N-methylamino] ethoxy] phenyl 2- (3-methylbutyl) propionic acid and its esters are described in WO95 / 03288.

(1-5) 3- [4- [2- [N- (2
-Benzoxazolyl) -N-methylamino] ethoxy] phenyl] -2- (2,2,2-trifluoroethoxy) propionic acid and esters thereof
No. 6/04260.

[0008] More recently, many thiazolidine derivatives have been reported as drugs for treating insulin-independent diabetes. Examples of these compounds include (2-1) 5- [4-[(6-hydroxy-2,5,
7,8-tetramethylchroman-2-yl) methoxy]
Benzyl] -2,4-thiazolidinedione (generic name: troglitazone) has been disclosed in US Pat. No. 4,572,912, EP 1
39421A and JP-B-2-31079.

(2-2) 5-[[4- [2- (5-ethyl-pyridin-2-yl) ethoxy] phenyl] methyl] -2,4-thiazolidinedione (generic name: pioglitazone) is an EP 8203A, USP 428720
0, USP 4,340,605, USP 443,814
1, USP 4444779, USP 472561
0, JP-B-62-42903 and JP-B-5-669
No. 56.

(2-3) 5-[[3,4-dihydro-
2- (phenylmethyl) -2H-benzopyran-6-yl] methyl] -2,4-thiazolidinedione (generic name:
Englitazone) is described in US Pat. No. 4,703,052 and Japanese Patent Publication No. 5-86953.

(2-4) 5-[[4- [2- [N-methyl-N- (pyridin-2-yl) amino] ethoxy]
Phenyl] methyl] -2,4-thiazolidinedione (generic name: rosiglitazone) is disclosed in EP 306228A, U
SP 5002953, USP 5194443, USP
No. 5,232,925, US Pat. No. 5,260,445 and JP-A-1-131169.

[0012] The relationship between these compounds and various diseases is described in the following literature, for example, for thiazolidine compounds.

Diabetes., 32 (9) , 804-810 (1983); D. Effect of thiazolidine compounds on hyperglycemia.
iabetes., 37 (11) , 1549-1558 (1988); Prog. Cli
n. Biol. Res., 265 , 177-192 (1988); Metabolism.,
37 (3) , 276-280 (1988); Arzneim.-Forsch., 40
(1) , 37-42 (1990); Arzneim.-Forsch., 40 (2, Pt.
1) , 156-162 (1990); Arzneim.-Forsch., 40 (3) ,
263-267 (1990);

Diabetes., 40 (12) , 1669-1674 (1991) shows the effect of thiazolidine compounds on hyperlipidemia;
Am. J. Physiol., 267 (1, Pt 1) , E95-E101 (1994);
Diabetes., 43 (10) , 1203-1210 (1994);

The effects of thiazolidine compounds on impaired glucose tolerance and insulin resistance are described by Arzneim.-Forsch., 4
0 (2, Pt 1) , 156-162 (1990); Metabolism., 40 (1
0) , 1025-1030 (1991); Diabetes., 43 (2) , 204-21
1 (1994); N. Engl. J. Med., 331 (18) , 1226-1227 (19
94);

The effects of thiazolidine compounds on hypertension are shown in Metabolism., 42 (1) , 75-80 (1993);
mJPhysiol., 265 (4, Pt 2) , R726-R732 (1993); D
iabetes. 43 (2) , 204-211 (1994);

The effect of thiazolidine compounds on cachexia is described in Endocrinology., 135 (5) , 2279-2282 (1994);
Endocrinology., 136 (4) , 1474-1481 (1995);

The effect on nephropathy is "diabetes", 38
Volume Extra Issue, (1995) (The 38th Annual Meeting of the Diabetes Society of Japan Program / Abstract Collection: The 38th Annual Meeting of the Diabetes Association, 1995).

The effects of thiazolidine compounds on coronary artery disease are described in Am. J. Physiol., 265 (4, Pt 2) , R726-R73.
2 (1993); Hypertension., 24 (2) , 170-175 (1994);
And so on.

The effects of thiazolidine compounds on arteriosclerosis are described in Am. J. Physyol., 265 (4, Pt 2) , R726-R73.
2 (1993);

Furthermore, in recent years, a normal person having insulin resistance without glucose intolerance has a high risk of developing diabetes [insulin resistant non-glucose intolerance (insulin registrant).
antnon-IGT: NGT). ] N.Engl.J.Me
d., 331 (18) , 1226-1227 (1994); It is suggested that a drug that improves insulin resistance is useful as a preventive drug for the onset of diabetes in normal individuals as described above.

However, the compounds described above are different in that they do not have the feature of the compounds of the present invention that they have an oxime bond in the side chain.

A compound having an oxime bond in the side chain has been disclosed as a therapeutic agent for non-insulin-dependent diabetes having the same action as described above after the priority date of the present application. These compounds include, for example, (4-1) 5
-[4- [2-[(4-hydroxyindan-1-yl) iminooxy] ethoxy] benzyl] -2,4-thiazolidinedione, 5- [4- [2-[(2,3-dihydro-6- Phenylbenzofuran-3-yl) iminooxy] ethoxy] benzyl] -2,4-thiazolidinedione, 5- [4- [2-[(5-chloroindan-
1-yl) iminooxy] ethoxy] benzyl] -2,
4-thiazolidinedione, 5- [4- [2-[(5-
Methylindan-1-yl) iminooxy] ethoxy]
Benzyl] -2,4-thiazolidinedione, 5- [4-
[2-[(5,6-methylenedioxyindan-1-yl) iminooxy] ethoxy] benzyl] -2,4-thiazolidinedione, 5- [4- [2-[(5-phenylindan-1-yl) ) Aromatic oximino derivatives such as iminooxy] ethoxy] benzyl] -2,4-thiazolidinedione are disclosed in WO 96/38427 (publication date: 1996.12.05) and
48770 (publication date: 1997.02.18).

(4-2) 5- [4- [2-[[[1-
(4-biphenylyl) ethylidene] amino] oxy] ethoxy] benzyl] thiazolidine-2,4-dione,
5- [4- [2-[[[1- [4- (2-pyridyl) phenyl] ethylidene] amino] oxy] ethoxy] benzyl] thiazolidine-2,4-dione, 5- [4-
[2-[[[1- (2-phenyl-5-pyridyl) ethylidene] amino] oxy] ethoxy] benzyl] thiazolidine-2,4-dione, 5- [4- [2-[[[1
-(2-methoxy-5-pyridyl) ethylidene] amino] oxy] ethoxy] benzyl] thiazolidine-2,
Oxime derivatives such as 4-dione are described in EP 70809
No. 8A (publication date: Apr. 24, 1996) and JP-A-9-48779 (publication date: Feb. 18, 1997).

[0025]

DISCLOSURE OF THE INVENTION The present inventors have found that novel phenylalkylcarboxylic acid derivatives, pharmacologically acceptable salts thereof or pharmacologically acceptable esters thereof have strong activity and extremely high safety, and have improved insulin resistance. Action, anti-inflammatory action, immunomodulatory action, aldose reductase inhibitory action, 5
The present invention was found to have a lipoxygenase inhibitory action, a lipid peroxide production inhibitory action, a PPAR activating action, an anti-osteoporosis action and the like, and completed the present invention.

That is, the present invention provides a novel phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof, comprising diabetes, hyperlipidemia, obesity, impaired glucose tolerance, and insulin resistance. Non-glucose intolerance, hypertension, fatty liver, diabetic complications (eg retinopathy, nephropathy,
Neurosis, cataract, coronary artery disease, etc.), arteriosclerosis, gestational diabetes, polycystic ovary syndrome, cardiovascular disease (eg, ischemic heart disease, etc.), cells caused by atherosclerosis or ischemic heart disease. Diseases primarily due to insulin resistance, such as damage (eg, brain injury caused by stroke); osteoarthritis, pain, fever, rheumatoid arthritis, inflammatory bowel disease, acne, sunburn, psoriasis, eczema, allergy Sexual diseases, asthma, GI ulcers, cancer, cachexia, autoimmune diseases (eg, systemic lupus erythematosus, juvenile rheumatoid arthritis, Sjogren's syndrome, systemic scleroderma, mixed connective tissue disease, dermatomyositis, Hashimoto's disease, primary Myxedema, thyrotoxicosis, pernicious anemia, ulcerative colitis, autoimmune atrophic gastritis,
Idiopathic Addison's disease, male infertility, Goodpas
Ture syndrome, acute progressive glomerulonephritis, myasthenia gravis, polymyositis, pemphigus vulgaris, bullous pemphigoid, sympathetic ophthalmitis, multiple sclerosis, autoimmune hemolytic anemia, idiopathic platelets Decreased purpura, post-myocardial infarction syndrome, rheumatic fever,
Inflammatory diseases such as lupoid hepatitis, primary biliary cirrhosis, Behcet's disease, CREST syndrome), pancreatitis;
Provided is a preventive and / or therapeutic agent for osteoporosis; cataract and the like.

[0027]

The present invention provides a compound represented by the general formula (I):

[0028]

Embedded image

The present invention relates to a medicament containing a phenylalkylcarboxylic acid derivative having the formula, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof.

In the above formula, R ¹ is a hydrogen atom or a group having 1 carbon atom.
R ² represents a linear or branched alkyl group having 2 to 6 carbon atoms, R ² represents a linear or branched alkyl group having 2 to 6 carbon atoms, and R ³ represents (i)
A hydrogen atom, (ii) a linear or branched alkyl group having 1 to 6 carbon atoms, (iii) a linear or branched alkoxy group having 1 to 4 carbon atoms, iv) a linear or branched alkylthio group having 1 to 4 carbon atoms, (v) a halogen atom, (vi) a nitro group, (vii) the same or different alkyls each having 1 to 4 carbon atoms. A linear or branched dialkylamino group having the formula: (vii
i) 1 to 3 aryl groups having 6 to 10 carbon atoms which may have a substituent α described below, or
(Ix) an aralkyl group having 1 to 3 carbon atoms having 7 to 12 carbon atoms which may have a substituent α described later, wherein Z is a single bond or 1 to 6 carbon atoms;
A linear or branched alkylene group having 1 to 6 carbon atoms, W represents (i) a linear or branched alkyl group having 1 to 6 carbon atoms, (ii) a hydroxy group, (iii) A) a straight-chain or branched alkoxy group having 1 to 4 carbon atoms, (iv) a straight-chain or branched alkylthio group having 1 to 4 carbon atoms, (v) an amino group, (Vi) 1 to 4 carbon atoms
(Vii) a straight or branched dialkylamino group having the same or different alkyls each having 1 to 4 carbon atoms, (viii) ) 1 to 4 carbon atoms
N-alkyl-N having 1 to 3 aryl groups having 6 to 10 carbon atoms which may have a substituent α described below in the linear or branched alkyl and aryl moiety having An arylamino group, (ix)
1 to 3 aryl groups having 6 to 10 carbon atoms which may have a substituent α described below, and (x) 1 to 3 aryl groups having 1 to 3 substituents α described below in the aryl moiety An aryloxy group having 6 to 10 carbon atoms, (xi) an arylthio group having 6 to 10 carbon atoms which may have 1 to 3 substituents α described later in the aryl moiety, and (xii) An arylamino group having 1 to 3 carbon atoms and 6 to 10 carbon atoms optionally having a substituent α described below, (xii)
i) an aralkyl group having 7 to 12 carbon atoms which may have 1 to 3 substituents α described later in the aryl moiety, and (xiv) 1 to 3 substituents α described later in the aryl moiety. Optionally having 7 to 12 carbon atoms
(Xv) an aralkyloxy group having 7 to 12 carbon atoms which may have 1 to 3 substituents α described later in the aryl moiety,
(Xvi) an aralkylamino group having 7 to 12 carbon atoms optionally having 1 to 3 substituents α described below in the aryl moiety, (xvii) a 1-pyrrolyl group,
(Xviii) 1-pyrrolidinyl group, (xix) 1
-Imidazolyl group, (xx) piperidino group or
(Xxi) represents a morpholino group, and X represents 1 to 3 carbon atoms having 6 to 1 carbon atoms which may have a substituent α described below.
An aryl group having 0 or 1 to 3 containing 1 to 4 hetero atoms selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom which may have a substituent α described below. And a 5- or 10-membered heteroaromatic ring group having two or more rings, in which the substituent α is:
A straight-chain or branched alkyl group having 1 to 6 carbon atoms, (ii) a straight-chain or branched alkyl halide group having 1 to 4 carbon atoms, (iii) a hydroxy group, (iv) A) straight-chain or branched aliphatic acyloxy group having 1 to 4 carbon atoms,
(V) a linear or branched alkoxy group having 1 to 4 carbon atoms, (vi) a linear or branched alkylenedioxy group having 1 to 4 carbon atoms, (vii A) an aralkyloxy group having 7 to 12 carbon atoms; (viii) a linear or branched alkylthio group having 1 to 4 carbon atoms;
x) a linear or branched alkylsulfonyl group having 1 to 4 carbon atoms, (x) a halogen atom,
(Xi) a nitro group, (xii) a straight or branched dialkylamino group having the same or different alkyls each having 1 to 4 carbon atoms, (xiii) an aralkyl group having 7 to 12 carbon atoms , (Xiv)
An aryl group having 6 to 10 carbon atoms (the aryl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl having 1 to 4 carbons) Substituted by a halogenated alkyl, linear or branched alkoxy having 1 to 4 carbons, halogen or a linear or branched alkylenedioxy having 1 to 4 carbons. (Xv) an aryloxy group having 6 to 10 carbon atoms (where the aryl moiety is a linear or branched alkyl having 1 to 6 carbon atoms, and 1 to 4 carbon atoms) Linear or branched alkyl halide having 1 to 4 carbon atoms, linear or branched alkoxy having 1 to 4 carbon atoms, halogen or linear having 1 to 4 carbon atoms Or (xvi) an arylthio group having 6 to 10 carbon atoms (where the aryl portion is a straight-chain or branched alkylthio group having 1 to 6 carbon atoms). Branched alkyl, straight-chain or branched alkyl halide having 1 to 4 carbon atoms, 1 to 4 carbon atoms
May be substituted with a straight-chain or branched alkoxy having one or two carbon atoms, a halogen or a straight-chain or branched alkylenedioxy having 1 to 4 carbon atoms. (Xvii) an arylsulfonyl group having 6 to 10 carbon atoms (where the aryl moiety is a straight-chain or branched alkyl having 1 to 6 carbons, a straight-chain having 1 to 4 carbons) Or branched alkyl halides, straight or branched alkoxy having 1 to 4 carbon atoms, halogen or straight or branched alkyl having 1 to 4 carbon atoms (Xvi may be substituted with dioxy).
ii) an arylsulfonylamino group having 6 to 10 carbon atoms (the aryl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl having 1 to 4 carbons) Branched alkyl halide, straight or branched alkoxy having 1 to 4 carbon atoms, halogen or 1 to 4 carbon atoms
It may be substituted by a straight-chain or branched alkylenedioxy having two or more carbon atoms. The nitrogen atom of the amino moiety may be substituted with a linear or branched alkyl having 1 to 6 carbons. (Xix) one ring or two containing 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur
A 5- to 10-membered heteroaromatic ring group, (xx) an oxygen atom,
A monocyclic or bicyclic 5- to 10-membered heteroaromatic oxy group containing 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom and a sulfur atom, (xxi) consisting of an oxygen atom, a nitrogen atom and a sulfur atom A monocyclic or bicyclic 5- to 10-membered heteroaromatic thio group containing 1 to 4 heteroatoms selected from the group; (xxiii) a heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom A monocyclic or bicyclic 5- to 10-membered heteroaromatic ring sulfonyl group containing 1 to 4 or
(Xxiii) a monocyclic or bicyclic 5- to 10-membered heteroaromatic sulfonylamino group containing 1 to 4 heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom (the nitrogen atom of the amino moiety May be substituted with a linear or branched alkyl having 1 to 6 carbons), and Y is an oxygen atom, a sulfur atom or a group having the formula> NR ⁴ (formula Wherein R ⁴ is a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched aliphatic acyl group having 1 to 8 carbon atoms, or Represents an aromatic acyl group).

Here, when R ¹ , R ³ , W and R ⁴ represent a linear or branched alkyl group having 1 to 6 carbon atoms, the alkyl group may be, for example, methyl, ethyl, Propyl, isopropyl, butyl, isobutyl,
s-butyl, t-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-
Dimethylpropyl, 1-ethylpropyl, hexyl, 1
-Methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3 -Dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-
It may be ethylbutyl, 1,1,2-trimethylpropyl or 1,2,2-trimethylpropyl, preferably a linear or branched alkyl group having 1 to 4 carbon atoms, more preferably Is methyl, ethyl, propyl, isopropyl, butyl or isobutyl.
R ¹ , R ³ and R ⁴ are even more preferably straight-chain or branched alkyl having 1 to 3 carbon atoms, most preferably alkyl having 1 to 2 carbon atoms. . W is even more preferably propyl or butyl, most preferably butyl.

When R ² represents a linear or branched alkylene group having 2 to 6 carbon atoms, the alkylene group may be, for example, ethylene, methylethylene, ethylethylene, 1,1-dimethylethylene, 1,2-dimethylethylene, trimethylene, 1-methyltrimethylene, 1
-Ethyltrimethylene, 2-methyltrimethylene, 1,
It may be 1-dimethyltrimethylene, tetramethylene, pentamethylene or hexamethylene, preferably a linear or branched alkylene group having 2 to 5 carbon atoms, more preferably 2 carbon atoms. And a straight-chain or branched alkylene group having from 4 to 4.
More preferably it is ethylene, methylethylene or trimethylene, most preferably ethylene.

When Z represents a linear or branched alkylene group having 1 to 6 carbon atoms, the alkylene group may be, for example, methylene, ethylene, methylethylene,
Ethyl ethylene, 1,1-dimethylethylene, 1,2-
Dimethylethylene, trimethylene, 1-methyltrimethylene, 1-ethyltrimethylene, 2-methyltrimethylene, 1,1-dimethyltrimethylene, tetramethylene,
It may be pentamethylene or hexamethylene, preferably a linear or branched alkylene group having 1 to 4 carbon atoms (for example, methylene, ethylene, methylethylene, ethylethylene, trimethylene, 1-methyltrimethylene) Or 2-methyltrimethylene), more preferably an alkylene group having 1 or 2 carbon atoms, most preferably methylene.

When R ³ and W represent a linear or branched alkoxy group having 1 to 4 carbon atoms,
The alkoxy group is, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, s-butoxy, t-
R ³ is preferably an alkoxy group having 1 to 2 carbon atoms, most preferably methoxy, and W is preferably 1 to 3 carbon atoms.
And more preferably ethoxy.

When R ³ and W represent a linear or branched alkylthio group having 1 to 4 carbon atoms, the alkylthio group is, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, s
-Butylthio, t-butylthio or isobutylthio, R ³ is preferably an alkylthio group having 1 to 2 carbon atoms, most preferably methylthio, and W is preferably 1 to 3 carbon atoms. And most preferably methylthio.

When R ³ represents a halogen atom, the halogen atom may be a fluorine, chlorine, bromine or iodine atom, preferably a fluorine, chlorine or bromine atom, most preferably a fluorine atom. Atom or chlorine atom.

When W represents a linear or branched monoalkylamino group having 1 to 4 carbon atoms, the monoalkylamino group may be, for example, methylamino, ethylamino, propylamino, isopropylamino, It can be butylamino, s-butylamino, t-butylamino or isobutylamino, preferably having 1 to 3 carbon atoms.
A linear or branched monoalkylamino group having at least one, and most preferably ethylamino.

When R ³ and W are the same or different and each alkyl represents a linear or branched dialkylamino group having 1 to 4 carbon atoms, the dialkylamino group is, for example, dimethylamino, diethylamino ,
It can be dipropylamino, diisopropylamino, dibutylamino, N-methyl-N-ethylamino or N-ethyl-N-isopropylamino, preferably dimethylamino or diethylamino, most preferably diethylamino.

When R ³ and W represent 1 to 3 aryl groups having 6 to 10 carbon atoms which may have a substituent α described below, the unsubstituted aryl group is, for example, phenyl or naphthyl. Possible and preferably phenyl. A substituted aryl group is, for example, 2-methylphenyl,
3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-propylphenyl, 4-isopropylphenyl, 4-trifluorobutylphenyl, 4-hydroxyphenyl, 4-acetoxyphenyl, 4-methoxyphenyl, 3,4 -Methylenedioxyphenyl, 4-benzyloxyphenyl, 4-methylthiophenyl, 4-
Methylsulfonylphenyl, 4-fluorophenyl, 4
-Chlorophenyl, 4-nitrophenyl, 4-dimethylaminophenyl, 4-benzylphenyl, 4-biphenylyl, 4-phenoxyphenyl, 4-phenylthiophenyl, 4-phenylsulfonylphenyl, 4-phenylsulfonylaminophenyl, 4- ( 2- (2-pyridyl) phenyl, 4- (2-pyridyloxy) phenyl, 4- (2
-Pyridylthio) phenyl or 4- (2-pyridylsulfonylamino) phenyl, preferably 4-methylphenyl, 4-ethylphenyl, 4-isopropylphenyl, 4-methoxyphenyl, 4-methylthiophenyl or 4-chlorophenyl It is.

R ³ and W are 1 to 3
When an aralkyl group having 7 to 12 carbon atoms which may have a substituent α described below is used, the unsubstituted aralkyl group is a linear or branched aralkyl group having 1 to 4 carbon atoms. Is a group in which the above-mentioned aryl group is substituted for the alkyl group, for example, benzyl, phenethyl,
R ³ is preferably benzyl or phenethyl, optimally benzyl, and W is preferably benzyl, phenethyl, which can be 3-phenylpropyl, 4-phenylbutyl, 1-naphthylmethyl or 2-naphthylmethyl. , 3
-Phenylpropyl or 4-phenylbutyl,
Most preferably phenethyl or 3-phenylpropyl. A substituted aralkyl group is, for example, 4-methylbenzyl,
4-trifluoromethylbenzyl, 4-methoxybenzyl, 3,4-methylenedioxybenzyl, 4-methylthiobenzyl, 4-methylsulfonylbenzyl, 4-fluorobenzyl, 4-chlorobenzyl, 2- (4-methylphenyl) Ethyl, 2- (4-methoxyphenyl) ethyl, 3- (4-methylphenyl) propyl, 3- (4-
Methoxyphenyl) propyl, 4- (4-methylphenyl) butyl or 4- (4-methoxyphenyl) butyl, preferably 4-methylbenzyl or 2- (4
-Methylphenyl) ethyl.

W is a straight-chain or branched alkyl and aryl moiety having 1 to 4 carbon atoms, and 1 to 3 carbon atoms which may have a substituent α described below.
N-alkyl- having from 10 to 10 aryls
When indicating an N-arylamino group, the alkyl of the unsubstituted N-alkyl-N-arylamino group can be, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl or t-butyl; Preferably it is methyl, ethyl, propyl, isopropyl, butyl or isobutyl, most preferably methyl or ethyl. The aryl can be, for example, phenyl or naphthyl, preferably phenyl. Unsubstituted N-alkyl-
Specific examples of the N-arylamino group include, for example, N-methyl-
N-phenylamino, N-ethyl-N-phenylamino, N-propyl-N-phenylamino, N-isopropyl-N-phenylamino, N-butyl-N-phenylamino, N-isobutyl-N-phenylamino or N
-Methyl-N-naphthylamino, preferably N-
Methyl-N-phenylamino or N-ethyl-N-phenylamino, most preferably N-ethyl-N-phenylamino. Substituted N-alkyl-N-arylamino groups include, for example, N-methyl-N- (4-methylphenyl) amino, N-ethyl-N- (4-methylphenyl)
Amino, N-methyl-N- (4-methoxyphenyl) amino or N-ethyl-N- (4-methoxyphenyl)
It can be amino, N-methyl-N- (4-methylphenyl) amino or N-ethyl-N- (4-methylphenyl) amino.

When W represents an aryloxy group having 1 to 3 carbon atoms and optionally having 6 to 10 carbon atoms which may have a substituent α described below, the unsubstituted aryloxy group is, for example, phenoxy or It may be naphthyloxy, preferably phenoxy. Substituted aryloxy groups include, for example, 4-methylphenoxy, 4-ethylphenoxy, 4-propylphenoxy, 4-isopropylphenoxy, 4-methoxyphenoxy, 4-ethoxyphenoxy, 4-methylthiophenoxy, 4-ethylthiophenoxy, It can be biphenylyloxy or 4-methylsulfonylphenoxy, preferably 4-methylphenoxy, 4-ethylphenoxy or 4-isopropylphenoxy.

When W represents an arylthio group having 1 to 3 carbon atoms and having 6 to 10 carbon atoms which may have a substituent α described later, the unsubstituted arylthio group is, for example, phenylthio or naphthylthio. Possible, preferably phenylthio. The substituted arylthio group is, for example, 4-methylphenylthio, 4-ethylphenylthio, 4-propylphenylthio, 4-isopropylphenylthio, 4-methoxyphenylthio, 4-ethoxyphenylthio, 4-methylthiophenylthio, 4-methylphenylphenyl, Ethylthiophenylthio, 4-biphenylylthio or 4
-Methylsulfonylphenylthio, preferably 4
-Methylphenylthio, 4-ethylphenylthio or 4-isopropylphenylthio.

When W represents an arylamino group having 1 to 3 carbon atoms and having 6 to 10 carbon atoms which may have a substituent α described later, the unsubstituted arylamino group is, for example, phenylamino Or naphthylamino, preferably phenylamino. Substituted arylamino groups include, for example, 4-methylphenylamino, 4-
Ethylphenylamino, 4-propylphenylamino,
4-isopropylphenylamino, 4-methoxyphenylamino, 4-ethoxyphenylamino, 4-methylthiophenylamino, 4-ethylthiophenylamino,
It can be -biphenylylamino or 4-methylsulfonylphenylamino, preferably 4-methylphenylamino, 4-ethylphenylamino or 4-isopropylphenylamino.

When W represents an aralkyloxy group having 1 to 3 carbon atoms and having 7 to 12 carbon atoms which may have a substituent α described later, the unsubstituted aralkyloxy group has 1 to 3 carbon atoms. And a straight- or branched-chain alkyloxy group having from 4 to 4 is substituted with the above-mentioned aryl group, for example, benzyloxy, phenethyloxy, 3-phenylpropyloxy,
It can be 4-phenylbutyloxy, 1-naphthylmethyloxy or 2-naphthylmethyloxy, preferably benzyloxy or phenethyloxy, most preferably benzyloxy. Substituted aralkyloxy groups include, for example, 4-methylbenzyloxy, 4-methoxybenzyloxy, 2- (4-methylphenyl) ethoxy,
(4-methoxyphenyl) ethoxy, 3- (4-methylphenyl) propoxy, 3- (4-methoxyphenyl)
It can be propoxy, 4- (4-methylphenyl) butoxy or 4- (4-methoxyphenyl) butoxy, preferably 4-methylbenzyloxy or 2- (4-methylphenyl) ethoxy.

When W represents an aralkylthio group having 1 to 3 carbon atoms and 7 to 12 carbon atoms which may have a substituent α described later, the unsubstituted aralkylthio group has 1 to 3 carbon atoms. And a straight or branched alkylthio group having from 4 to 4 aryl groups substituted with the above-mentioned aryl group, such as benzylthio, phenethylthio, 3-phenylpropylthio, 4-phenylbutylthio, -Naphthylmethylthio or 2-naphthylmethylthio, preferably benzylthio or phenethylthio, most preferably benzylthio. A substituted aralkylthio group is, for example, 4-methylbenzylthio,
4-methoxybenzylthio, 2- (4-methylphenyl) ethylthio, 2- (4-methoxyphenyl) ethylthio, 3- (4-methylphenyl) propylthio, 3-
It can be (4-methoxyphenyl) propylthio, 4- (4-methylphenyl) butylthio or 4- (4-methoxyphenyl) butylthio, preferably with 4-methylbenzylthio or 2- (4-methylphenyl) ethylthio. is there.

When W represents an aralkylamino group having 1 to 3 carbon atoms and 7 to 12 carbon atoms which may have a substituent α described later, the unsubstituted aralkylamino group has 1 to 3 carbon atoms. And a straight- or branched-chain alkylamino group having 4 to 4 substituents substituted with the above-mentioned aryl group, such as benzylamino, phenethylamino, 3-phenylpropylamino,
It can be 4-phenylbutylamino, 1-naphthylmethylamino or 2-naphthylmethylamino, preferably benzylamino or phenethylamino, most preferably benzylamino. Examples of the substituted aralkylamino group include 4-methylbenzylamino, 4-methoxybenzylamino, 2- (4-methylphenyl) ethylamino,
-(4-methoxyphenyl) ethylamino, 3- (4-
Methylphenyl) propylamino, 3- (4-methoxyphenyl) propylamino, 4- (4-methylphenyl) butylamino or 4- (4-methoxyphenyl)
It can be butylamino, preferably 4-methylbenzylamino or 2- (4-methylphenyl) ethylamino.

When R ⁴ represents a linear or branched aliphatic or aromatic acyl group having 1 to 8 carbon atoms, the acyl group may be, for example, formyl, acetyl, propionyl, butyryl, It may be pentanoyl, hexanoyl, heptanoyl or octanoyl, benzoyl or p-toluoyl, preferably a straight-chain or branched alkanoyl group having 1 to 8 carbon atoms, more preferably 2 to 2 carbon atoms. It is a straight or branched alkanoyl group having 5 groups, most preferably an acetyl group.

When X represents 1 to 3 aryl groups having 6 to 10 carbon atoms which may have a substituent α described below, the unsubstituted aryl group may be, for example, phenyl or naphthyl; Preferably it is phenyl. When X represents an aryl group substituted with 1 to 3 substituents α described below, the number of the substituents is preferably 1 or 2
And more preferably one.

X is a ring or a ring containing 1 to 4 heteroatoms selected from the group consisting of 1 to 3 oxygen atoms, nitrogen atoms and sulfur atoms optionally having a substituent α described below. When a bicyclic 5- to 10-membered heteroaromatic ring group is represented, the unsubstituted heteroaromatic ring group is a monocyclic or bicyclic ring system. When it comprises a two-ring system, at least one ring is at least a heterocyclic ring. In the case of a two-ring system, it is a condensed ring, and one ring is a heterocyclic ring and the other ring is a carbocyclic ring;
It may be a ring coheterocycle. Heterocycles are 5- or 6-membered rings which contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur. A carbocycle is an aryl group having 6 to 10 carbon atoms. A monocyclic ring is called a heteroaromatic monocyclic group, and a bicyclic ring is called a heteroaromatic fused ring group. In the case of a ring having four heteroatoms, preferably all four are nitrogen atoms,
In the case where the number of hetero atoms selected from the group consisting of an oxygen atom and a sulfur atom is zero, and in the case of a ring having three hetero atoms, preferably three, two or one is a nitrogen atom, Or two or more are hetero atoms selected from the group consisting of oxygen and sulfur atoms, and in the case of a ring having two hetero atoms, preferably two, one or zero is a nitrogen atom , 0, 1 or 2 are heteroatoms selected from the group consisting of oxygen and sulfur atoms. When X represents a heteroaromatic group substituted with 1 to 3 substituents α described below, the number of the substituents is preferably 1 or 2, and more preferably 1.

The unsubstituted heteroaromatic monocyclic group includes a pyrrolyl group such as 2-pyrrolyl and 3-pyrrolyl; 2-furyl,
Furyl groups such as 3-furyl; thienyl groups such as 2-thienyl and 3-thienyl; pyridyl groups such as 2-pyridyl, 3-pyridyl and 4-pyridyl; imidazolyls such as 2-imidazolyl and 4-imidazolyl Pyrazolyl groups such as 3-pyrazolyl and 4-pyrazolyl; 2-
Oxazolyl groups such as oxazolyl, 4-oxazolyl and 5-oxazolyl; isoxazolyl groups such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl; 2-thiazolyl, 4-thiazolyl, 5-
Thiazolyl groups such as thiazolyl; isothiazolyl groups such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl; 1,2,3-triazol-4-yl, 1,2,4-triazol-3-yl and the like Triazolyl group; thiadiazolyl group such as 1,3,4-thiadiazol-2-yl; oxadiazolyl group such as 1,3,4-oxadiazol-2-yl; tetrazolyl group such as 5-tetrazolyl; Pyridazinyl, 4
Pyridazinyl groups such as -pyridazinyl; pyrimidinyl groups such as 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl; pyrazinyl groups; 1,4-oxazine-2
Oxazinyl groups such as -yl, 1,4-oxazin-3-yl; thiazinyl groups such as 1,4-thiazin-2-yl, 1,4-thiazin-3-yl; An aromatic fused ring group is, for example, indol-2-yl,
Indole-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indole-
An indolyl group such as 7-yl; an indazolyl group such as indazol-2-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl;
Benzofuranyl groups such as benzofuran-2-yl, benzofuran-3-yl, benzofuran-4-yl, benzofuran-5-yl, benzofuran-6-yl, benzofuran-7-yl; benzothiophen-2-yl, benzothiophene -3-yl, benzothiophen-4-yl, benzothiophen-5-yl, benzothiophen-
Benzothiophenyl groups such as 6-yl, benzothiophen-7-yl; benzimidazol-2-yl, benzimidazol-4-yl, benzimidazole-5-yl
Benzoimidazolyl groups such as yl, benzimidazol-6-yl, benzimidazol-7-yl; benzoxazol-2-yl, benzoxazol-4-yl, benzoxazol-5-yl, benzoxazol-6-yl, benzo Benzoxazolyl groups such as oxazol-7-yl; benzothiazol-2-yl;
Benzothiazol-4-yl, benzothiazol-5
Benzothiazolyl groups such as yl, benzothiazol-6-yl, benzothiazol-7-yl; 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-
Quinolyl groups such as quinolyl, 7-quinolyl and 8-quinolyl; isoquinolyl groups such as 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl and 8-isoquinolyl;
Benzoxazinyl groups such as 1,4-benzoxazin-2-yl, 1,4-benzoxazin-3-yl;
Benzothiazinyl groups such as 1,4-benzothiazin-2-yl, 1,4-benzothiazin-3-yl; pyrrolo [2,3-b] pyrid-2-yl, pyrrolo [2,3-
b] pyrrolo [2,3-b] pyridyl groups such as pyridi-3-yl; furo [2,3-b] pyrid-2-yl, furo [2,3-b] pyrid-3-yl Na flow [2,3
-B] pyridyl group; thieno [2,3-b] pyridin-2-
Thieno [2,3-b] pyridyl groups such as yl, thieno [2,3-b] pyrid-3-yl; 1,8-naphthyridin-2-yl, 1,8-naphthyridin-3-yl, ,
5-naphthyridin-2-yl, 1,5-naphthyridin-
Naphthyridinyl groups such as 3-yl; imidazo [4,5
-B] pyrid-2-yl, imidazopyridyl groups such as imidazo [4,5-b] pyridin-5-yl; oxazolo [4,5-b] pyrid-2-yl, oxazolo [5,4
-B] an oxazolopyridyl group such as pyrid-2-yl; and thiazolo [4,5-b] pyrid-2-yl;
A thiazolopyridyl group such as thiazolo [4,5-c] pyrid-2-yl;

The heteroaromatic monocyclic group is preferably a 5- or 6-membered ring group having 1 to 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur.
Examples include the pyrrolyl group, furyl group, thienyl group, pyridyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, triazolyl group, thiadiazolyl group, oxadiazolyl group, pyridazinyl group, pyrimidinyl group and pyrazinyl group.
The fused heteroaromatic ring group is preferably a condensation of a benzene ring and a 5- or 6-membered heteroaromatic monocyclic ring having 1 to 3 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. A ring group, such as an indolyl group, a benzofuranyl group, a benzothiophenyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinolyl group, or an isoquinolyl group.

More preferably, they are imidazolyl, oxazolyl, pyridyl, indolyl, quinolyl or isoquinolyl, even more preferably pyridyl, indolyl, quinolyl or isoquinolyl. It is a pyridyl group, a quinolyl group or an isoquinolyl group, particularly a pyridyl group.

X is an aryl group having 6 to 10 carbon atoms or a 5 to 10 ring or 1 to 2 ring containing 1 to 4 hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur atoms. When a membered heteroaromatic ring group is represented, the aryl group and the heteroaromatic ring group may have 1 to 3 substituents α as described above.

Here, the substituent α is a linear or branched alkyl group having 1 to 6 carbon atoms,
A straight-chain or branched alkoxy group having 1 to 4 carbon atoms, a straight-chain or branched alkylthio group having 1 to 4 carbon atoms, a halogen atom or the same or different alkyl having 1 to 4 carbon atoms When a straight-chain or branched-chain dialkylamino group having from 4 to 4 is shown, these groups may be the same as those described for R ³ above.

When the substituted α represents a linear or branched halogenated alkyl group having 1 to 4 carbon atoms, the halogenated alkyl group is, for example, chloromethyl,
Bromomethyl, fluoromethyl, iodomethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl or trichloromethyl, preferably 1 to 3 Is a methyl having a fluorine atom,
Particularly preferred is trifluoromethyl.

When the substituted α represents a linear or branched aliphatic acyloxy group having 1 to 4 carbon atoms, the acyloxy group may be, for example, formyloxy, acetoxy, propionyloxy, butyryloxy, acroyl It can be oxy, methacryloyloxy or crotonoyloxy, preferably an alkanoyloxy group, more preferably an alkanoyloxy having 1-2 carbon atoms, most preferably acetoxy.

When the substituted α is a linear or branched alkylenedioxy group having 1 to 4 carbon atoms, the alkylenedioxy group is, for example, methylenedioxy, ethylenedioxy, trimethylene. Dioxy, tetramethylenedioxy or propylenedioxy,
Preferably it is methylenedioxy or ethylenedioxy, particularly preferably methylenedioxy.

When the substituted α represents an aralkyloxy group having 7 to 12 carbon atoms, the aralkyloxy group is an aralkyloxy group in which the aralkyl moiety is the same aralkyl as described for R ³ , for example, benzyl Oxy, phenethyloxy, 3-phenylpropoxy,
4-phenylbutoxy, 1-naphthylmethoxy or 2
-Naphthylmethoxy, preferably benzyloxy, phenethyloxy, 1-naphthylmethoxy or 2
-Naphthylmethoxy, more preferably benzyloxy.

When the substituted α represents a linear or branched alkylsulfonyl group having 1 to 4 carbon atoms, the alkylsulfonyl group is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, It can be butylsulphonyl, isobutylsulphonyl, sec-butylsulphonyl or t-butylsulphonyl, preferably methylsulphonyl, ethylsulphonyl or isopropylsulphonyl, particularly preferably alkylsulphonyl having 1 or 2 carbon atoms. When the substituent α represents an aralkyl group having 7 to 12 carbon atoms, the aralkyl group is an aralkyl group having the same meaning as described for R ³ , for example, benzyl, phenethyl, 3-phenylpropyl, 4-phenylbutyl , 1
-Naphthylmethyl or 2-naphthylmethyl;
Preferably it is benzyl, phenethyl, 1-naphthylmethyl or 2-naphthylmethyl, more preferably benzyl.

An aryl group in which the substituent α has 6 to 10 carbon atoms (the aryl group is a straight-chain or branched alkyl having 1 to 6 carbons, a straight chain having 1 to 4 carbons) Linear or branched alkyl halides, linear or branched alkoxy having 1 to 4 carbon atoms, halogen or linear or branched alkyl having 1 to 4 carbon atoms May be substituted with alkylenedioxy.), The alkyl, halogenated alkyl, alkoxy, halogen and alkylenedioxy in the substituted portion are the same as those described above for R ³ and X.
Has the same meaning as that described for the substitution.

The aryl group includes, for example, phenyl, 1-naphthyl, 2-naphthyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxyphenyl,
It can be ethoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 3-bromophenyl or 3,4-methylenedioxyphenyl, preferably phenyl, 4-methoxyphenyl or 3,4-methylenedioxyphenyl.

An aryloxy group having 6 to 10 carbon atoms in which the substituent α has 1 to 6 carbon atoms;
Straight or branched alkyl having 1 to 4 carbon atoms, straight or branched alkyl halide having 1 to 4 carbon atoms, straight or branched alkyl having 1 to 4 carbon atoms Alkoxy, halogen or a linear or branched alkylenedioxy having 1 to 4 carbon atoms. ), The alkyl, halogenated alkyl, alkoxy,
Halogen and alkylenedioxy are as defined above.

The aryloxy group includes, for example, phenoxy, 1-naphthoxy, 2-naphthoxy, 4-methylphenoxy, 4-trifluoromethylphenoxy, 4-methoxyphenoxy, 3-ethoxyphenoxy, 4-chlorophenoxy, 3-bromo It can be phenoxy or 3,4-methylenedioxyphenoxy, preferably phenoxy.

An arylthio group having 6 to 10 carbon atoms in which the substituent α is a straight-chain or branched alkyl having 1 to 6 carbons, a straight-chain or branched alkyl having 1 to 6 carbons; Linear or branched alkyl halides, linear or branched alkoxy having 1 to 4 carbon atoms, halogen or linear or branched alkyl having 1 to 4 carbon atoms (Optionally substituted with alkylenedioxy)), the substituted alkyl, halogenated alkyl, alkoxy, halogen and alkylenedioxy have the same meanings as described above.

The arylthio group includes, for example, phenylthio, 4-methylphenylthio, 4-trifluoromethylphenylthio, 4-methoxyphenylthio, 3-ethoxyphenylthio, 4-chlorophenylthio, 3-bromophenylthio, It can be 4-methylenedioxyphenylthio, 1-naphthylthio or 2-naphthylthio, preferably phenylthio.

An arylsulfonyl group in which the substituent α has 6 to 10 carbon atoms (the aryl moiety is a linear or branched alkyl having 1 to 6 carbon atoms, and has 1 to 4 carbon atoms) Straight-chain or branched alkyl halide, straight-chain or branched alkoxy having 1 to 4 carbon atoms, halogen or straight-chain or branched chain having 1 to 4 carbon atoms May be substituted with alkylenedioxy.)
The substituted alkyl, halogenated alkyl, alkoxy, halogen and alkylenedioxy have the same meaning as described above.

The arylsulfonyl group includes, for example, phenylsulfonyl, 4-methylphenylsulfonyl, 4-trifluoromethylphenylsulfonyl, 4-methoxyphenylsulfonyl, 3-ethoxyphenylsulfonyl,
It can be 4-chlorophenylsulfonyl, 3-bromophenylsulfonyl, 3,4-methylenedioxyphenylsulfonyl, 1-naphthylsulfonyl or 2-naphthylsulfonyl, preferably phenylsulfonyl.

The substituted α is an arylsulfonylamino group having 6 to 10 carbon atoms (the aryl moiety is a linear or branched alkyl having 1 to 6 carbon atoms; Straight or branched alkyl halides having 1 to 4 carbon atoms, straight or branched alkoxy, halogen or straight or branched chains having 1 to 4 carbon atoms The nitrogen atom of the amino moiety may be substituted by a linear or branched alkyl having 1 to 6 carbon atoms.)
Wherein the alkyl, halogenated alkyl, alkoxy, halogen and alkylenedioxy in the substituted portion have the same meaning as described above.

The arylsulfonylamino group includes, for example, phenylsulfonylamino, 4-methylphenylsulfonylamino, 4-trifluoromethylphenylsulfonylamino, 4-methoxyphenylsulfonylamino,
-Ethoxyphenylsulfonylamino, 4-chlorophenylsulfonylamino, 3-bromophenylsulfonylamino, 3,4-methylenedioxyphenylsulfonylamino, N-methylphenylsulfonylamino, 1-naphthylsulfonylamino, 2-naphthylsulfonylamino or N -Methylnaphthylsulfonylamino, preferably phenylsulfonylamino or N-methylphenylsulfonylamino.

The substitution α is 1 to 4 hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur.
When a monocyclic or bicyclic 5- to 10-membered heteroaromatic group is contained, the group may be, for example, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, imidazolyl, quinolyl, isoquinolyl, indolyl or pyridyl, It is preferably imidazolyl, quinolyl or pyridyl, particularly preferably pyridyl.

The substitution α is 1 to 4 hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur.
When a monocyclic or bicyclic 5- to 10-membered heteroaromatic oxy group is contained, the heteroaromatic oxy group may be, for example, furyloxy, thienyloxy, oxazolyloxy, isoxazolyloxy, thiazolyloxy, Imidazolyloxy, quinolyloxy, isoquinolyloxy, indolyloxy or pyridyloxy,
Preferably it is isoxazolyloxy or pyridyloxy, particularly preferably pyridyloxy.

The substitution α is 1 to 4 hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur.
When a monocyclic or bicyclic 5- to 10-membered heteroaromatic thio group is contained, the heteroaromatic thio group is, for example, furylthio, thienylthio, oxazolylthio, isoxazolylthio, thiazolylthio, imidazolylthio, quinolylthio, isoquinolylthio. , Indolylthio or pyridylthio, preferably isoxazolylthio or pyridylthio, particularly preferably pyridylthio.

The substitution α is 1 to 4 hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur.
When a monocyclic or bicyclic 5- to 10-membered heteroaromatic sulfonyl group is contained, the heteroaromatic sulfonyl group is, for example, furylsulfonyl, thienylsulfonyl, oxazolylsulfonyl, isoxazolylsulfonyl,
Thiazolylsulfonyl, imidazolylsulfonyl, quinolylsulfonyl, isoquinolylsulfonyl, indolylsulfonyl or pyridylsulfonyl, preferably imidazolylsulfonyl, isoxazolylsulfonyl or pyridylsulfonyl, particularly preferably pyridylsulfonyl It is.

The substitution α is 1 to 4 hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur.
A monocyclic or bicyclic 5- to 10-membered heteroaromatic sulfonylamino group containing at least one nitrogen atom in which the nitrogen atom is substituted by a linear or branched alkyl having 1 to 6 carbon atoms; The heteroaromatic ring sulfonylamino group may be, for example, furylsulfonylamino, thienylsulfonylamino, oxazolylsulfonylamino, isoxazolylsulfonylamino, thiazolylsulfonylamino, imidazolylsulfonylamino, N -Methylimidazolylsulfonylamino, quinolylsulfonylamino, isoquinolylsulfonylamino,
It can be indolylsulfonylamino, pyridylsulfonylamino or N-methylpyridylsulfonylamino, preferably imidazolylsulfonylamino, N-methylimidazolylsulfonylamino, pyridylsulfonylamino or N-methylpyridylsulfonylamino, particularly preferably Pyridylsulfonylamino or N-
Methylpyridylsulfonylamino.

Accordingly, X is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms or 1 to 4 heteroatoms selected from the group consisting of substituted or unsubstituted oxygen, nitrogen and sulfur atoms. When a monocyclic or bicyclic 5- to 10-membered heteroaromatic ring group is contained, preferred examples thereof include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, an m-tolyl group and a p-tolyl group. ,
3-ethylphenyl group, 4-ethylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group,
3-t-butylphenyl group, 4-t-butylphenyl group, 4-chloromethylphenyl group, 4-bromomethylphenyl group, 4-fluoromethylphenyl group, 4-iodomethylphenyl group, 3-difluoromethylphenyl group ,
4-trifluoromethylphenyl group, 4-pentafluoroethylphenyl group, 4-trichloromethylphenyl group, 3-hydroxyphenyl group, 4-hydroxyphenyl group, 4-hydroxy-3, 5-dimethylphenyl group,
3-acetoxyphenyl group, 4-acetoxyphenyl group, 5-acetoxy-2-hydroxy-3,4,6-trimethylphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-ethoxyphenyl group, 4- Ethoxyphenyl group, 3-isopropoxyphenyl group, 4-
Isopropoxyphenyl group, 3,4-methylenedioxyphenyl group, benzyloxyphenyl group, phenethyloxyphenyl group, 1-naphthylmethoxyphenyl group, 3
-Methylthiophenyl group, 4-methylthiophenyl group,
3-ethylthiophenyl group, 4-ethylthiophenyl group, 3-isopropylthiophenyl group, 4-isopropylthiophenyl group, 3-methylsulfonylphenyl group,
4-methylsulfonylphenyl group, 3-ethylsulfonylphenyl group, 4-ethylsulfonylphenyl group, 3-
Isopropylsulfonylphenyl group, 4-isopropylsulfonylphenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 3-bromophenyl group, 4-bromophenyl group, 4-nitrophenyl group, 4-aminophenyl group, 3-methylamino Phenyl group, 4-ethylaminophenyl group, 3-propylaminophenyl group, 4-butylaminophenyl group, 3-dimethylaminophenyl group, 4
-Diethylaminophenyl group, 3-dipropylaminophenyl group, 4-dibutylaminophenyl group, 3-benzylphenyl group, 4-benzylphenyl group, 3-phenethylphenyl group, 4- (1-naphthylmethyl) phenyl group, -Biphenylyl group, 4-biphenylyl group, 3-
(4-methylphenyl) phenyl, 4- (4-methylphenyl) phenyl, 3- (4-ethylphenyl) phenyl, 3- (4-trifluoromethylphenyl) phenyl, 4- (4-triphenyl) A fluoromethylphenyl) phenyl group, a 3- (4-methoxyphenyl) phenyl group,
4- (4-methoxyphenyl) phenyl group, 3- (2,
4-dimethoxyphenyl) phenyl group, 4- (2,4-
Dimethoxyphenyl) phenyl group, 3- (2,5-dimethoxyphenyl) phenyl group, 4- (2,5-dimethoxyphenyl) phenyl group, 4- (3-chlorophenyl)
A phenyl group, a 4- (4-chlorophenyl) phenyl group,
4- (3-bromophenyl) phenyl group, 4- (4-bromophenyl) phenyl group, 3- (3,4-methylenedioxyphenyl) phenyl group, 4- (3,4-methylenedioxyphenyl) phenyl Group, 3-benzylphenyl group, 4-benzylphenyl group, 3-phenoxyphenyl group, 4-phenoxyphenyl group, 3-phenylthiophenyl group, 4-phenylthiophenyl group, 3-phenylsulfonylphenyl group, 4-phenyl Sulfonylphenyl group, 3- (phenylsulfonylamino) phenyl group, 4
-(Phenylsulfonylamino) phenyl group, 3- (N
-Methylphenylsulfonylamino) phenyl group, 4-
An (N-methylphenylsulfonylamino) phenyl group,
3- (imidazol-1-yl) phenyl group, 4- (imidazol-1-yl) phenyl group, 3- (1-methylimidazol-4-yl) phenyl group, 4- (1-methylimidazol-4-yl) ) Phenyl, 3- (2-furyl) phenyl, 4- (2-furyl) phenyl, 3
-(2-thienyl) phenyl group, 4- (2-thienyl)
Phenyl group, 3- (3-thienyl) phenyl group, 4-
(3-thienyl) phenyl group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 3- (3
-Pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 3- (4-pyridyl) phenyl group, 4- (4-pyridyl) phenyl group, 4- (imidazol-1-ylthio) phenyl group, 4- A (2-furylthio) phenyl group,
4- (2-thienylthio) phenyl group, 4- (2-pyridylthio) phenyl group, 4- (4-pyridylthio) phenyl group, 3- (2-pyridylsulfonyl) phenyl group,
4- (2-pyridylsulfonyl) phenyl group, 3- (3
-Pyridylsulfonyl) phenyl group, 4- (3-pyridylsulfonyl) phenyl group, 3- (2-pyridylsulfonylamino) phenyl group, 3- (N-methyl-2-pyridylsulfonylamino) phenyl group, 4- (2 -Pyridylsulfonylamino) phenyl group, 4- (N-methyl-
2-pyridylsulfonylamino) phenyl group, 3- (3
-Pyridylsulfonylamino) phenyl group, 3- (N-
A methyl-3-pyridylsulfonylamino) phenyl group,
4- (3-pyridylsulfonylamino) phenyl group, 4
-(N-methyl-3-pyridylsulfonylamino) phenyl group, 3- (oxazol-2-yl) phenyl group,
4- (oxazol-2-yl) phenyl group, 3- (oxazol-4-yl) phenyl group, 4- (oxazol-4-yl) phenyl group, 3- (oxazol-5
Yl) phenyl, 4- (oxazol-5-yl) phenyl, 3- (thiazol-2-yl) phenyl,
4- (thiazol-2-yl) phenyl group, 3- (thiazol-4-yl) phenyl group, 4- (thiazol-4)
-Yl) phenyl group, 3- (thiazol-5-yl) phenyl group, 4- (thiazol-5-yl) phenyl group,
1-methyl-2-pyrrolyl group, 1-phenyl-2-pyrrolyl group, 1-benzyl-2-pyrrolyl group, 5-methyl-
2-furyl group, 5-phenyl-2-furyl group, 5-methyl-2-thienyl group, 5-phenyl-2-thienyl group,
5-methyl-3-thienyl group, 5-phenyl-3-thienyl group, 1-methyl-3-pyrazolyl group, 1-phenyl-3-pyrazolyl group, 1-methyl-2-imidazolyl group, 1-phenyl-2 -Imidazolyl group, 1-methyl-
4-imidazolyl group, 1-phenyl-4-imidazolyl group, 1-methyl-2-phenyl-4-imidazolyl group,
1,5-dimethyl-2-phenyl-4-imidazolyl group, 1,4-dimethyl-2-phenyl-5-imidazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-
Methyl-4-oxazolyl group, 2-phenyl-4-oxazolyl group, 2-methyl-5-oxazolyl group, 2-phenyl-5-oxazolyl group, 4-methyl-2-phenyl-5-oxazolyl group, 5-methyl -2-phenyl-
4-oxazolyl group, 4-thiazolyl group, 5-thiazolyl group, 2-methyl-4-thiazolyl group, 2-phenyl-
4-thiazolyl group, 2-methyl-5-thiazolyl group, 2
-Phenyl-5-thiazolyl group, 4-methyl-2-phenyl-5-thiazolyl group, 5-methyl-2-phenyl-
4-thiazolyl group, 1-methyl-3-pyrazolyl group, 1
-Phenyl-3-pyrazolyl group, 3-methyl-5-isoxazolyl group, 3-phenyl-5-isoxazolyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 3-methyl-5-pyridyl group, 3-ethyl-5-pyridyl group, 3-phenyl-5-pyridyl group, 2-methyl-5-pyridyl group, 2-ethyl-5-pyridyl group, 2-
Phenyl-5-pyridyl group, 2-hydroxy-5-pyridyl group, 2-methoxy-5-pyridyl group, 2-ethoxy-5-pyridyl group, 2-isopropoxy-5-pyridyl group, 2-benzyloxy-5 -Pyridyl group, 2-methylthio-5-pyridyl group, 2-ethylthio-5-pyridyl group, 2-isopropylthio-5-pyridyl group, 2-methylsulfonyl-5-pyridyl group, 2-ethylsulfonyl-5-pyridyl Group, 2-isopropylsulfonyl-5-
Pyridyl group, 2-benzyl-5-pyridyl group, 2-phenoxy-5-pyridyl group, 2-phenylthio-5-pyridyl group, 2-phenylsulfonyl-5-pyridyl group, 2
-Phenylsulfonylamino-5-pyridyl group, 2-
(N-methylphenylsulfonylamino) -5-pyridyl group, 3-methyl-6-pyridyl group, 3-phenyl-6
-Pyridyl group, 2-methyl-6-pyridyl group, 2-phenyl-6-pyridyl group, 2-methyl-4-pyrimidinyl group, 2-phenyl-4-pyrimidinyl group, 2-methoxy-4-pyrimidinyl group, 2 -Ethoxy-4-pyrimidinyl group, 2-isopropoxy-4-pyrimidinyl group, 2-
Methylthio-4-pyrimidinyl group, 2-ethylthio-4
-Pyrimidinyl group, 2-isopropylthio-4-pyrimidinyl group, 2-phenylthio-4-pyrimidinyl group, 2
-Methylsulfonyl-4-pyrimidinyl group, 2-ethylsulfonyl-4-pyrimidinyl group, 2-isopropylsulfonyl-4-pyrimidinyl group, 2-phenylsulfonyl-4-pyrimidinyl group, 2-methyl-5-pyrimidinyl group, 2- Phenyl-5-pyrimidinyl group, 2-methoxy-5-pyrimidinyl group, 2-ethoxy-5-pyrimidinyl group, 2-isopropoxy-5-pyrimidinyl group, 2
-Methylthio-5-pyrimidinyl group, 2-ethylthio-
5-pyrimidinyl group, 2-isopropylthio-5-pyrimidinyl group, 2-phenylthio-5-pyrimidinyl group,
2-methylsulfonyl-5-pyrimidinyl group, 2-ethylsulfonyl-5-pyrimidinyl group, 2-isopropylsulfonyl-5-pyrimidinyl group, 2-phenylsulfonyl-5-pyrimidinyl group, 2-indolyl group, 3-indolyl group, 1-methyl-2-indolyl group, 1-methyl-3-indolyl group, 2-benzimidazolyl group, 1
-Methyl-2-benzimidazolyl group, 2-benzoxazolyl group, 2-benzthiazolyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl Or an 8-isoquinolyl group, preferably a phenyl group, 1-
Naphthyl group, 2-naphthyl group, m-tolyl group, p-tolyl group, 3-ethylphenyl group, 4-ethylphenyl group,
3-isopropylphenyl group, 4-isopropylphenyl group, 4-trifluoromethylphenyl group, 3-hydroxyphenyl group, 4-hydroxyphenyl group, 4-hydroxy-3, 5-dimethylphenyl group, 3-acetoxyphenyl group, 4-acetoxyphenyl group, 5-acetoxy-2-hydroxy-3,4,6-trimethylphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-ethoxyphenyl group, 4-ethoxyphenyl group, 3- Isopropoxyphenyl group, 4-isopropoxyphenyl group, 3,4-methylenedioxyphenyl group,
Benzyloxyphenyl group, 3-methylthiophenyl group, 4-methylthiophenyl group, 3-ethylthiophenyl group, 4-ethylthiophenyl group, 3-methylsulfonylphenyl group, 4-methylsulfonylphenyl group, 3-
Ethylsulfonylphenyl group, 4-ethylsulfonylphenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 3-benzylphenyl group, 4-benzylphenyl group, 3-biphenylyl group, 4-biphenylyl group, 3-
(4-methylphenyl) phenyl, 4- (4-methylphenyl) phenyl, 3- (4-ethylphenyl) phenyl, 3- (4-trifluoromethylphenyl) phenyl, 4- (4-triphenyl) A fluoromethylphenyl) phenyl group, a 3- (4-methoxyphenyl) phenyl group,
4- (4-methoxyphenyl) phenyl group, 3- (2,
4-dimethoxyphenyl) phenyl group, 4- (2,4-
Dimethoxyphenyl) phenyl group, 3- (2,5-dimethoxyphenyl) phenyl group, 4- (2,5-dimethoxyphenyl) phenyl group, 4- (3-chlorophenyl)
A phenyl group, a 4- (4-chlorophenyl) phenyl group,
3- (3,4-methylenedioxyphenyl) phenyl group, 4- (3,4-methylenedioxyphenyl) phenyl group, 3-phenoxyphenyl group, 4-phenoxyphenyl group, 3-phenylthiophenyl group, -Phenylthiophenyl group, 3-phenylsulfonylphenyl group, 4
-Phenylsulfonylphenyl group, 3- (phenylsulfonylamino) phenyl group, 4- (phenylsulfonylamino) phenyl group, 3- (N-methylphenylsulfonylamino) phenyl group, 4- (N-methylphenylsulfonylamino) phenyl Group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 3- (3
-Pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 3- (4-pyridyl) phenyl group, 4- (4-pyridyl) phenyl group, 4- (2-pyridyloxy) phenyl group, 4- ( 4-pyridyloxy) phenyl group, 4-
(2-pyridylthio) phenyl group, 4- (4-pyridylthio) phenyl group, 3- (2-pyridylsulfonyl) phenyl group, 4- (2-pyridylsulfonyl) phenyl group, 3- (3-pyridylsulfonyl) phenyl group , 4-
(3-pyridylsulfonyl) phenyl group, 3- (2-pyridylsulfonylamino) phenyl group, 3- (N-methyl-2-pyridylsulfonylamino) phenyl group, 4-
(2-pyridylsulfonylamino) phenyl group, 4-
(N-methyl-2-pyridylsulfonylamino) phenyl group, 3- (3-pyridylsulfonylamino) phenyl group, 3- (N-methyl-3-pyridylsulfonylamino) phenyl group, 4- (3-pyridylsulfonylamino) group ) Phenyl, 4- (N-methyl-3-pyridylsulfonylamino) phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-methyl-5-pyridyl, 3-ethyl-5- Pyridyl group, 3-phenyl-5-
Pyridyl group, 2-methyl-5-pyridyl group, 2-ethyl-5-pyridyl group, 2-phenyl-5-pyridyl group, 2
-Hydroxy-5-pyridyl group, 2-methoxy-5-pyridyl group, 2-ethoxy-5-pyridyl group, 2-isopropoxy-5-pyridyl group, 2-benzyloxy-5-
Pyridyl group, 2-methylthio-5-pyridyl group, 2-ethylthio-5-pyridyl group, 2-isopropylthio-5
-Pyridyl group, 2-methylsulfonyl-5-pyridyl group, 2-ethylsulfonyl-5-pyridyl group, 2-isopropylsulfonyl-5-pyridyl group, 2-benzyl-
5-pyridyl group, 2-phenoxy-5-pyridyl group, 2
-Phenylthio-5-pyridyl group, 2-phenylsulfonyl-5-pyridyl group, 2-phenylsulfonylamino-5-pyridyl group, 2- (N-methylphenylsulfonylamino) -5-pyridyl group, 3-methyl-6 -Pyridyl group, 3-phenyl-6-pyridyl group, 2-methyl-6
-A pyridyl group, a 2-phenyl-6-pyridyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group or an 8-isoquinolyl group; More preferably, phenyl, m-tolyl, p-tolyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 4-hydroxy-3, 5-dimethylphenyl, 3-acetoxyphenyl, 4-acetoxy Phenyl group, 5-acetoxy-2
-Hydroxy-3,4,6-trimethylphenyl group, 3
-Chlorophenyl group, 4-chlorophenyl group, 3-benzylphenyl group, 4-benzylphenyl group, 3-biphenylyl group, 4-biphenylyl group, 3-phenoxyphenyl group, 4-phenoxyphenyl group, 3-phenylthiophenyl group, 4-phenylthiophenyl group, 3-phenylsulfonylphenyl group, 4-phenylsulfonylphenyl group, 3- (phenylsulfonylamino) phenyl group,
4- (phenylsulfonylamino) phenyl group, 3-
An (N-methylphenylsulfonylamino) phenyl group,
4- (N-methylphenylsulfonylamino) phenyl group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 3- (3-pyridyl) phenyl group,
4- (3-pyridyl) phenyl group, 3- (4-pyridyl) phenyl group, 4- (4-pyridyl) phenyl group,
-(2-pyridyloxy) phenyl group, 4- (4-pyridyloxy) phenyl group, 4- (2-pyridylthio) phenyl group, 4- (4-pyridylthio) phenyl group, 3-
(2-pyridylsulfonyl) phenyl group, 4- (2-pyridylsulfonyl) phenyl group, 3- (3-pyridylsulfonyl) phenyl group, 4- (3-pyridylsulfonyl) phenyl group, 3- (2-pyridylsulfonylamino) ) Phenyl, 2-pyridyl, 3-pyridyl, 4
-Pyridyl group, 2-methoxy-5-pyridyl group, 2-ethoxy-5-pyridyl group, 2-isopropoxy-5-pyridyl group, 2-benzyloxy-5-pyridyl group, 2-
Methylthio-5-pyridyl group, 2-ethylthio-5-pyridyl group, 2-methylsulfonyl-5-pyridyl group, 2
-Ethylsulfonyl-5-pyridyl group, 2-benzyl-
5-pyridyl group, 2-phenyl-5-pyridyl group, 3-
Phenyl-5-pyridyl group, 2-phenyl-6-pyridyl group, 3-phenyl-6-pyridyl group, 2-phenoxy-5-pyridyl group, 2-phenylthio-5-pyridyl group, 2-phenylsulfonyl-5- Pyridyl group, 2-phenylsulfonylamino-5-pyridyl group or 2-
(N-methylphenylsulfonylamino) -5-pyridyl group.

When Y is a group having the formula> NR ⁴ , wherein R is
⁴ is a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms (having the same meaning as described for R ³ ) or a linear or branched alkyl group having 1 to 8 carbon atoms. It represents a branched aliphatic acyl group (including an alkanoyl group having 1 to 8 carbon atoms and an alkenoyl group having 3 to 8 carbon atoms) or an aromatic acyl group. ), Groups having the formula> NR ⁴ are, for example, imino, methylimino, ethylimino, propylimino, isopropylimino, butylimino, isobutylimino, s-butylimino, t-butylimino, pentylimino, 1-methylbutylimino , 2-methylbutylimino, 3-methylbutylimino, 1,1-dimethylpropylimino, 1,2-dimethylpropylimino, 2,2
-Dimethylpropylimino, 1-ethylpropylimino, hexylimino, 1-methylpentylimino, 2-
Methylpentylimino, 3-methylpentylimino, 4
-Methylpentylimino, 1,1-dimethylbutylimino, 1,2-dimethylbutylimino, 1,3-dimethylbutylimino, 2,2-dimethylbutylimino, 2,3
-Dimethylbutylimino, 3,3-dimethylbutylimino, 1-ethylbutylimino, 1,1,2-trimethylpropylimino, 1,2,2-trimethylpropylimino, acetylimino, propionylimino, butylylimino, pentanoylimino , Hexanoyl imino, heptanoyl imino, octanoyl imino, benzoyl imino or p-toluoyl imino, preferably a straight-chain or branched alkyl imino having an imino group, having 1 to 4 carbon atoms. Or an acetylimino group, most preferably an imino group, a methylimino group, an ethylimino group or an acetylimino group.

The phenylalkylcarboxylic acid having the general formula (I) of the present invention can be converted into an acid addition salt when it has a basic group according to a conventional method. Such salts are, for example, salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid; inorganic acids such as nitrates, perchlorates, sulfates, phosphates Salts; salts of lower alkanesulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and ethanesulfonic acid; salts of arylsulfonic acids such as benzenesulfonic acid and p-toluenesulfonic acid; amino acids such as glutamic acid and aspartic acid And salts of carboxylic acids such as acetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid and citric acid. Preferably, it is a salt of hydrohalic acid.

Further, since the compound having the general formula (I) has a carboxyl group, it can be converted into a metal salt according to a conventional method. Such salts include, for example, alkali metal salts such as lithium, sodium, potassium;
Alkaline earth metal salts such as calcium, barium and magnesium; aluminum salts; and the like. Preferably, it is an alkali metal salt.

The phenylalkylcarboxylic acid having the general formula (I) of the present invention can be converted into a pharmacologically acceptable ester according to a conventional method. The pharmacologically acceptable ester of the phenylalkyl carboxylic acid having the general formula (I) is more medically used than the phenylalkyl carboxylic acid having the general formula (I) and is pharmacologically acceptable. There is no particular limitation.

The ester of the phenylalkylcarboxylic acid having the general formula (I) of the present invention may be, for example, a linear or branched alkyl group having 1 to 6 carbon atoms, or a 7 to 19 carbon atoms. An aralkyl group having 1 to 5 carbon atoms, a linear or branched alkanoyloxy having 1 to 6 carbon atoms, a linear or branched alkyl group having 1 to 5 carbon atoms, A straight-chain or branched alkyloxycarbonyloxy having 6 carbon atoms substituted by a straight-chain or branched alkyl group having 1 to 5 carbon atoms, a cycloalkyl having 5 to 7 carbon atoms A carbonyloxy-substituted linear or branched alkyl group having 1 to 5 carbon atoms, a cycloalkyloxy carboxy having 5 to 7 carbon atoms Aryloxy is C 1 -C been substituted straight-chain or branched alkyl radical having five,
A straight-chain or branched alkyl group having 1 to 5 carbon atoms substituted by an arylcarbonyloxy having 6 to 10 carbon atoms, a carbon atom substituted by an aryloxycarbonyloxy having 6 to 10 carbon atoms Number 1
2-oxo-1, having a linear or branched alkyl group having from 5 to 5 and a linear or branched alkyl having 1 to 6 carbon atoms as a substituent at the 5-position; A 3-dioxolen-4-yl 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,
1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1
-Dimethylbutyl, 1,2-dimethylbutyl, 1,3-
Dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl or 1,2,2-trimethylpropyl Possible
Preferably it is a linear or branched alkyl group having 1 to 4 carbon atoms, more preferably methyl, ethyl, propyl, isopropyl, butyl or isobutyl, most preferably methyl or ethyl. is there.

An aralkyl group having 7 to 19 carbon atoms is, for example, benzyl, phenethyl, 3-phenylpropyl, 4-phenylbutyl, 1-naphthylmethyl, 2-
It can be naphthylmethyl or diphenylmethyl, preferably benzyl. Cycloalkyl groups having 5 to 7 carbon atoms are, for example, cyclopentyl, cyclohexyl, cycloheptyl, preferably cyclohexyl.

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

Specific examples of suitable ester residues include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, benzyl, acetoxymethyl,
-(Acetoxy) ethyl, propionyloxymethyl,
1- (propionyloxy) ethyl, butyryloxymethyl, 1- (butyryloxy) ethyl, isobutyryloxymethyl, 1- (isobutyryloxy) ethyl, valeryloxymethyl, 1- (valeryloxy) ethyl, isovale Ryloxymethyl, 1- (isovaleryloxy)
Ethyl, pivaloyloxymethyl, 1- (pivaloyloxy) ethyl, methoxycarbonyloxymethyl, 1-
(Methoxycarbonyloxy) ethyl, ethoxycarbonyloxymethyl, 1- (ethoxycarbonyloxy)
Ethyl, propoxycarbonyloxymethyl, 1- (propoxycarbonyloxy) ethyl, isopropoxycarbonyloxymethyl, 1- (isopropoxycarbonyloxy) ethyl, butoxycarbonyloxymethyl,
1- (butoxycarbonyloxy) ethyl, isobutoxycarbonyloxymethyl, 1- (isobutoxycarbonyloxy) ethyl, t-butoxycarbonyloxymethyl, 1- (t-butoxycarbonyloxy) ethyl,
Cyclopentanecarbonyloxymethyl, 1- (cyclopentanecarbonyloxy) ethyl, cyclohexanecarbonyloxymethyl, 1- (cyclohexanecarbonyloxy) ethyl, cyclopentyloxycarbonyloxymethyl, 1- (cyclopentyloxycarbonyloxy) ethyl, cyclohexyloxycarbonyloxy Methyl, 1- (cyclohexyloxycarbonyloxy) ethyl, benzoyloxymethyl, 1- (benzoyloxy) ethyl, phenoxycarbonyloxymethyl, 1- (phenoxycarbonyloxy) ethyl or 5-methyl-2-oxo-1,3- Dioxolen-4-
Ill.

The compound having the general formula (I) has various isomers. For example, there are optical isomers derived from the asymmetric carbon at the α-position of the carboxylic acid. In the general formula (I), stereoisomers based on these asymmetric carbon atoms, and equivalent and unequal mixtures of these isomers are all represented by a single formula. Therefore, in the present invention, all of these isomers and a mixture of these isomers are also included.

Further, in the phenylalkylcarboxylic acid having the general formula (I), a cis isomer and a trans isomer based on geometrical isomerism may be present in the oxime group. In the general formula (I), both isomers based on these and equal and unequal mixtures thereof are all represented by a single formula. Therefore, in the present invention, all of these isomers and a mixture of these isomers are also included.

Further, in the present invention, when the phenylalkylcarboxylic acid having the general formula (I) or a salt thereof forms a solvate (for example, a hydrate), these are all included.

Further, in the present invention, all so-called prodrugs such as compounds which are metabolized in the living body and converted into phenylalkylcarboxylic acid having the general formula (I) or a salt thereof, for example, amide derivatives are also included.

In the phenylalkylcarboxylic acid derivative having the general formula (I), preferably, (1) R ¹ is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. Certain compounds.

(2) Compounds wherein R ¹ is a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms.

(3) The compound wherein R ¹ is a hydrogen atom or an alkyl group having 1 or 2 carbon atoms.

(4) The compound wherein R ¹ is an alkyl group having 1 or 2 carbon atoms.

(5) A compound wherein R ² is a linear or branched alkylene group having 2 to 5 carbon atoms.

(6) The compound wherein R ² is a linear or branched alkylene group having 2 to 4 carbon atoms.

(7) The compound wherein R ² is an ethylene group, a trimethylene group or a methylethylene group.

(8) The compound wherein R ² is an ethylene group.

(9) R ³ represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a 1 to 2 carbon atom. Compounds having an alkylthio group or a halogen atom.

(10) Compounds wherein R ³ is a hydrogen atom.

(11) X is an aryl group having 1 to 3 carbon atoms which may have a substituent α described later and having 6 to 10 carbon atoms, or has 1 to 3 substituents α described later. A 5- to 10-membered (single or bicyclic) heteroaromatic ring group containing 1 to 4 heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom which may be Wherein the substituted α is (i) a linear or branched alkyl having 1 to 6 carbons, (ii) a linear or branched alkyl having 1 to 4 carbons Alkyl halides, (iii) hydroxy, (iv) straight-chain or branched alkanoyloxy having 1 to 4 carbon atoms, (v) straight-chain or branched chain having 1 to 4 carbon atoms Alkoxy, (vi) carbon number A straight-chain or branched alkylenedioxy having four, (vi
i) aralkyloxy having 7 to 12 carbon atoms,
(Viii) linear or branched alkylthio having 1 to 4 carbons, (ix) linear or branched alkylsulfonyl having 1 to 4 carbons, (x) fluorine atom (Xi) chlorine atom,
(Xiii) a bromine atom, (xiii) a carbon number of 7 to 1.
Aralkyl having two, (xiv) phenyl (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl having 1 to 4 carbons) Alkyl halide, 1 carbon atom
It may be substituted by straight-chain or branched alkoxy having 4 to 4 carbon atoms, halogen or straight-chain or branched alkylenedioxy having 1 to 4 carbon atoms. (Xv) phenoxy (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl halide having 1 to 4 carbons) May be substituted by linear or branched alkoxy having 1 to 4 carbons, halogen, or linear or branched alkylenedioxy having 1 to 4 carbons. ), (Xvi) phenylthio (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl halide having 1 to 4 carbons) Substituted with linear or branched alkoxy having 1 to 4 carbon atoms, halogen or linear or branched alkylenedioxy having 1 to 4 carbon atoms. (Xvii) phenylsulfonyl (wherein the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl having 1 to 4 carbons) Linear alkyl halides, linear or branched alkoxy having 1 to 4 carbon atoms,
It may be substituted by halogen or linear or branched alkylenedioxy having 1 to 4 carbon atoms. ), (Xviii) phenylsulfonylamino (where the phenyl moiety is a straight-chain or branched-chain alkyl having 1 to 6 carbons, a straight-chain or branched-chain halogen having 1 to 4 carbons) Alkyl, straight-chain or branched alkoxy having 1 to 4 carbons, halogen or straight-chain or branched alkylenedioxy having 1 to 4 carbons The nitrogen atom of the amino moiety may be substituted by a linear or branched alkyl having 1 to 6 carbons.), (Xix) furyl,
(Xx) thienyl, (xxi) oxazolyl, (xx
(ii) isoxazolyl, (xxiii) thiazolyl, (xxiv) pyridyl, (xxv) pyridyloxy, (xxvi) pyridylthio, (xxvii)
Pyridylsulfonyl, (xxviii) imidazolyl (the ring nitrogen atom may be substituted by linear or branched alkyl having 1 to 6 carbon atoms)
And (xxix) a compound selected from the group consisting of pyridylsulfonylamino (where the nitrogen atom of the amino moiety may be substituted by linear or branched alkyl having 1 to 6 carbon atoms). .

(12) X is 1 to 3 phenyl groups, naphthyl groups, imidazolyl groups, oxazolyl groups, pyridyl groups, indolyl groups, quinolyl groups or isoquinolyl groups which may have the substituent α described below. Wherein the substituted α is (i) a linear or branched alkyl having 1 to 6 carbons, (ii) a linear or branched alkyl having 1 to 4 carbons Alkyl halide, (iii) hydroxy, (iv) carbon number 1
Linear or branched alkanoyloxy having 1 to 4 carbon atoms, (v) linear or branched alkoxy having 1 to 4 carbon atoms, (vi) methylenedioxy, (vii) carbon Aralkyloxy having 7 to 12 carbon atoms, (viii) linear or branched alkylthio having 1 to 4 carbon atoms,
(Ix) a linear or branched alkylsulfonyl having 1 to 4 carbon atoms, (x) a fluorine atom,
(Xi) chlorine atom, (xii) bromine atom, (xii
i) an aralkyl having 7 to 12 carbon atoms, (x
iv) phenyl, wherein the phenyl moiety may be substituted with methyl, trifluoromethyl, methoxy, fluoro or methylenedioxy; (xv) phenoxy, wherein the phenyl moiety is methyl, trifluoromethyl, methoxy, fluoro or (Xvi) phenylthio (the phenyl moiety may be substituted with methyl, trifluoromethyl, methoxy, fluoro or methylenedioxy), (xvii) phenylsulfonyl (The phenyl moiety may be substituted with methyl, trifluoromethyl, methoxy, fluoro or methylenedioxy), (xviii) phenylsulfonylamino (where the phenyl moiety is methyl, trifluoromethyl, methoxy, fluoro or methylenedioxy) Dioxy The nitrogen atom of the amino moiety may have 1 to 6 carbon atoms.
May be substituted with a straight-chain or branched-chain alkyl. ), (Xix) ruffle, (xx)
Thienyl, (xxi) oxazolyl, (xxii)
Isoxazolyl, (xxiii) thiazolyl,
(Xxiv) pyridyl, (xxv) pyridyloxy,
(Xxvi) pyridylthio, (xxvii) pyridylsulfonyl, (xxviii) imidazolyl (the nitrogen atom of the ring may be substituted by linear or branched alkyl having 1 to 6 carbon atoms) and xxix) a compound selected from the group consisting of pyridylsulfonylamino (where the nitrogen atom of the amino moiety may be substituted by linear or branched alkyl having 1 to 6 carbon atoms).

(13) X is 1 to 3 phenyl groups, naphthyl groups, imidazolyl groups, oxazolyl groups, pyridyl groups, indolyl groups, quinolyl groups or isoquinolyl groups which may have the substituent α described below. Wherein the substituted α is (i) a linear or branched alkyl having 1 to 6 carbons, (ii) a linear or branched alkyl having 1 to 4 carbons Alkyl halide, (iii) hydroxy, (iv) carbon number 1
A straight-chain or branched alkanoyloxy having 1 to 4 carbon atoms, (v) a straight-chain or branched alkoxy having 1 to 4 carbon atoms, (vi) methylenedioxy, (vii) benzyl Oxy, (vii
i) phenethyloxy, (ix) naphthylmethoxy,
(X) linear or branched alkylthio having 1 to 4 carbons, (xi) linear or branched alkylsulfonyl having 1 to 4 carbons,
(Xii) a fluorine atom, (xiii) a chlorine atom,
(Xiv) a bromine atom, (xv) benzyl, (xv
i) phenyl, wherein the phenyl moiety may be substituted by methyl, trifluoromethyl, methoxy, fluoro or methylenedioxy; (xvii) phenoxy, wherein the phenyl moiety is methyl, trifluoromethyl, methoxy, fluoro or (Xviii) phenylthio, (x
(xx) phenylsulfonyl, (xx) phenylsulfonylamino, (xxi) N-methylphenylsulfonylamino, (xxii) furyl, (xxiii) thienyl, (xxiv) oxazolyl, (xxv) isoxazolyl, (xxvi) thiazolyl, (xxvi)
i) pyridyl, (xxviii) pyridyloxy,
(Xxxix) pyridylthio, (xxx) pyridylsulfonyl, (xxxi) pyridylsulfonylamino,
(Xxxii) N-methylpyridylsulfonylamino and (xxxiii) imidazolyl (the ring nitrogen atom may be substituted by linear or branched alkyl having 1 to 6 carbon atoms). A compound selected from:

(14) X is one or two phenyl groups, naphthyl groups, pyridyl groups, indolyl groups, quinolyl groups or isoquinolyl groups which may have the substituent α described below, wherein the substituent α Is a linear or branched alkyl having 1 to 3 carbons, methyl having 1 to 3 fluorine atoms, hydroxy, alkanoyloxy having 1 to 2 carbons, 1 to 3 carbons Linear or branched alkoxy having 1 or 2 carbon atoms, methylenedioxy, benzyloxy, alkylthio having 1 or 2 carbon atoms, alkylsulfonyl having 1 or 2 carbon atoms, fluorine atom,
Chlorine atom, bromine atom, benzyl, phenyl, 4
-Methylphenyl, 4-trifluoromethylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 3,4-methylenedioxyphenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, furyl, Thienyl, oxazolyl, thiazolyl, imidazolyl, N-methylimidazolyl,
A compound selected from the group consisting of pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino.

(15) X is one phenyl group, naphthyl group, pyridyl group which may have one substituent α described below,
A quinolyl group or an isoquinolyl group, wherein the substituent α is methyl, ethyl, isopropyl, trifluoromethyl, hydroxy, acetoxy, methoxy, ethoxy, isopropoxy, methylenedioxy, benzyloxy, having 1 to 2 carbon atoms. Having alkylthio, alkylsulfonyl having 1 or 2 carbon atoms, a chlorine atom,
A compound selected from the group consisting of benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino .

(16) X is one phenyl group which may have a substituent α described below, wherein the substituent α is
Selected from the group consisting of methyl, hydroxy, acetoxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl, or X is one pyridyl group optionally having a substituent α described below, wherein the substituent α is
Methoxy, ethoxy, isopropoxy, benzyloxy, alkylthio having 1 to 2 carbons, alkylsulfonyl having 1 to 2 carbons, benzyl,
A compound selected from the group consisting of phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino and N-methylphenylsulfonylamino.

(17) X is one phenyl group which may have a substituent α described below, wherein the substituent α is
A compound selected from the group consisting of hydroxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, pyridyl, pyridyloxy and pyridylthio.

(18) Y is an oxygen atom, a sulfur atom or a group having the formula> NR ⁴ (wherein R ⁴ is a hydrogen atom, a straight-chain or branched-chain having 1 to 3 carbon atoms) An alkyl group or a linear or branched alkanoyl group having 2 to 5 carbon atoms).

(19) Compounds wherein Y is an oxygen atom.

(20) Compounds wherein Z is a single bond or a linear or branched alkylene group having 1 to 4 carbon atoms.

(21) Compounds wherein Z is a linear or branched alkylene group having 1 to 4 carbon atoms.

(22) The compound wherein Z is an alkylene group having 1 or 2 carbon atoms.

(23) The compound wherein Z is a methylene group.

(24) W is (i) a linear or branched alkyl group having 1 to 6 carbon atoms,
i) a linear or branched alkoxy group having 1 to 4 carbon atoms; (iii) a linear or branched alkylthio group having 1 to 4 carbon atoms;
(Iv) a linear or branched monoalkylamino group having 1 to 4 carbon atoms; (v) a linear or branched monoalkylamino group having the same or different and each alkyl having 1 to 4 carbon atoms. A dialkylamino group, (vi)
Straight-chain or branched alkyl and aryl having 1 to 4 carbon atoms, and 1 to 3 aryl having 6 to 10 carbon atoms which may have a substituent α described later. An N-alkyl-N-arylamino group, (vii) an aryloxy group having 1 to 3 carbon atoms and 6 to 10 carbon atoms which may have a substituent α described later, and (viii) an aryl moiety. Having 1 to 3 arylthio groups having 6 to 10 carbon atoms which may have a substituent α described below,
(Ix) an arylamino group having 6 to 10 carbon atoms which may have 1 to 3 substituents α described later in the aryl moiety, and (x) 1 to 3 substituents described later in the aryl moiety. an aralkyl group having 7 to 12 carbon atoms which may have α, (xi) 1-pyrrolyl group, (xii) 1-pyrrolidinyl group, (xiii)
1-imidazolyl group, (xiv) piperidino group or (xv) morpholino group, wherein the substitution α is
(I) a linear or branched alkyl having 1 to 6 carbons, (ii) a linear or branched alkyl halide having 1 to 4 carbons,
(Iii) hydroxy, (iv) linear or branched alkanoyloxy having 1 to 4 carbon atoms, (v) linear or branched alkoxy having 1 to 4 carbon atoms, (Vi) 1 to 4 carbon atoms
(Vii) aralkyloxy having 7 to 12 carbon atoms, (viii) straight or branched alkylene dioxy having 1 to 4 carbon atoms Alkylthio, (ix)
Linear or branched alkylsulfonyl having 1 to 4 carbon atoms, (x) a fluorine atom, (xi)
A chlorine atom, (xii) a bromine atom, (xiii) an aralkyl having 7 to 12 carbon atoms, (xiv) phenyl (the phenyl portion is a straight or branched alkyl having 1 to 6 carbon atoms, 1 to 4 carbon atoms
Linear or branched alkyl halide having 1 to 4 carbon atoms, linear or branched alkoxy having 1 to 4 carbon atoms, halogen or linear or branched alkyl having 1 to 4 carbon atoms. It may be substituted with a branched alkylenedioxy. (Xv) phenoxy (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl halide having 1 to 4 carbons) May be substituted by linear or branched alkoxy having 1 to 4 carbons, halogen, or linear or branched alkylenedioxy having 1 to 4 carbons. ), (Xvi) phenylthio (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl halide having 1 to 4 carbons) Linear or branched alkoxy having 1 to 4 carbon atoms,
It may be substituted by halogen or linear or branched alkylenedioxy having 1 to 4 carbon atoms. ), (Xvii) phenylsulfonyl (wherein the phenyl moiety is a straight-chain or branched alkyl having 1 to 6 carbons, a straight-chain or branched halogen having 1 to 4 carbons) Alkyl, linear or branched alkoxy having 1 to 4 carbon atoms, halogen, or linear or branched alkylenedioxy having 1 to 4 carbon atoms may be substituted. ), (Xviii) phenylsulfonylamino (where the phenyl moiety is a straight-chain or branched alkyl having 1 to 6 carbons, a straight-chain or branched alkyl having 1 to 4 carbons) Alkyl halide, straight-chain or branched alkoxy having 1 to 4 carbon atoms, halogen or straight-chain or branched chain having 1 to 4 carbon atoms (Xix) furyl; the nitrogen atom of the amino moiety may be substituted by linear or branched alkyl having 1 to 6 carbon atoms. (Xx) thienyl, (xxi) oxazolyl,
(Xxii) isoxazolyl, (xxiii) thiazolyl, (xxiv) pyridyl, (xxv) pyridyloxy, (xxvi) pyridylthio, (xxvi)
(xxviii) imidazolyl (the nitrogen atom of the ring may be substituted by linear or branched alkyl having 1 to 6 carbon atoms) and (xxix) pyridylsulfonylamino ( Wherein the nitrogen atom of the amino moiety may be substituted by linear or branched alkyl having 1 to 6 carbon atoms.)

(25) W is (i) a linear or branched alkyl group having 1 to 6 carbon atoms,
i) a linear or branched alkoxy group having 1 to 4 carbon atoms; (iii) a linear or branched alkylthio group having 1 to 4 carbon atoms;
(Iv) a linear or branched monoalkylamino group having 1 to 4 carbon atoms; (v) a linear or branched monoalkylamino group having the same or different and each alkyl having 1 to 4 carbon atoms. A dialkylamino group, (vi)
Straight-chain or branched alkyl and aryl having 1 to 4 carbon atoms, and 1 to 3 aryl having 6 to 10 carbon atoms which may have a substituent α described later. An N-alkyl-N-arylamino group, (vii) an aryloxy group having 1 to 3 carbon atoms and 6 to 10 carbon atoms which may have a substituent α described later, and (viii) an aryl moiety. Having 1 to 3 arylthio groups having 6 to 10 carbon atoms which may have a substituent α described below,
(Ix) an arylamino group having 6 to 10 carbon atoms which may have 1 to 3 substituents α described later in the aryl moiety, and (x) 1 to 3 substituents described later in the aryl moiety. an aralkyl group having 7 to 12 carbon atoms which may have α or (xi) a 1-pyrrolyl group, wherein the substituent α is hydroxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, pyridyl And a compound selected from the group consisting of pyridyloxy and pyridylthio.

(26) W is (i) a linear or branched alkyl group having 1 to 4 carbon atoms,
i) a linear or branched alkoxy group having 1 to 4 carbon atoms; (iii) a linear or branched alkylthio group having 1 to 4 carbon atoms;
(Iv) a linear or branched monoalkylamino group having 1 to 4 carbon atoms; (v) a linear or branched monoalkylamino group having the same or different and each alkyl having 1 to 4 carbon atoms. A dialkylamino group, (vi)
An N-alkyl-N-arylamino group having a linear or branched alkyl having 1 to 4 carbons and an aryl having 6 to 10 carbons, (v
(ii) phenoxy group, (viii) phenylthiothio group, (ix) phenylamino group, (x) aralkyl group having 7 to 10 carbon atoms, (xi) 1-pyrrolyl group, (xii) 1-pyrrolidinyl group or (Xi
ii) A compound which is a 1-imidazolyl group.

(27) W is (i) a propyl or butyl group, (ii) a linear or branched alkoxy group having 1 to 3 carbon atoms, (iii) having 1 to 3 carbon atoms. A linear or branched alkylthio group, (iv) a linear or branched monoalkylamino group having 1 to 3 carbon atoms, (v)
(Vi) N-phenyl-N-ethylamino group, (vii) phenoxy group, (vii
i) a phenylthio group, (ix) a phenylamino group,
(X) a compound which is a 3-phenylpropyl group, (xi) a 4-phenylbutyl group or (xii) a 1-pyrrolyl group.

(28) W is butyl, ethoxy, methylthio, ethylamino, diethylamino, N-
Compounds which are a phenyl-N-ethylamino group, a phenoxy group, a phenylthio group, a phenylamino group, a 3-phenylpropyl group or a 1-pyrrolyl group.

(29) Compounds wherein W is butyl, ethoxy, methylthio, ethylamino, phenoxy, phenylthio, phenylamino or 3-phenylpropyl.

[0119] In addition, (1) to select R ¹ from (4), (5) to select R ² from (8), (9) to (10) to select the R ³ from, (11) To X from (17) to Y from (18) to (19),
Compounds in which Z is selected from (20) to (23) and W is selected from (24) to (29) are also preferable.

For example, in the phenylalkylcarboxylic acid having the general formula (I), (30) R ¹ is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms; R ²
Is a linear or branched alkylene group having 2 to 5 carbon atoms; R ³ is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms,
An alkoxy group having 1 to 2 carbon atoms, an alkylthio group having 1 to 2 carbon atoms or a halogen atom; Z is a single bond or a linear or branched alkylene having 1 to 4 carbon atoms Is a group; W is
(I) a linear or branched alkyl group having 1 to 6 carbon atoms, (ii) a linear or branched alkoxy group having 1 to 4 carbon atoms, (ii)
i) a linear or branched alkylthio group having 1 to 4 carbon atoms; (iv) a linear or branched monoalkylamino group having 1 to 4 carbon atoms; The same or different, each alkyl is a straight-chain or branched dialkylamino group having 1 to 4 carbon atoms, (vi) a straight-chain or branched alkyl having 1 to 4 carbon atoms, and An N-alkyl-N-arylamino group having 1 to 3 aryls having 6 to 10 carbons which may have a substituent α described below, which is described later, and (vii)
An aryloxy group having 1 to 3 carbon atoms having 6 to 10 carbon atoms which may have a substituent α to be described later, and (viii) 1 to 3 substitutions to be described later which are present in the aryl portion. An arylthio group having 6 to 10 carbon atoms which may have a moiety α, (i
x) an arylamino group having 1 to 3 carbon atoms having 6 to 10 carbon atoms which may have a substituent α to be described later, and (x) an arylamino group having 1 to 3 carbon atoms to be described later. An aralkyl group having 7 to 12 carbon atoms which may have a substituent α, (xi)
1-pyrrolyl group, (xii) 1-pyrrolidinyl group,
(Xiii) a 1-imidazolyl group, (xiv) a piperidino group or (xv) a morpholino group; Aryl group having, or 1
A 5- to 10-membered ring (1 to 3) containing 1 to 4 hetero atoms selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom which may have a substituent α described later. A heterocyclic ring group consisting of a ring or a bicyclic ring), wherein the substituent α described below is: (i) a linear or branched alkyl having 1 to 6 carbon atoms, (ii) A linear or branched alkyl halide having 1 to 4 carbon atoms, (iii) hydroxy, (iv) a linear or branched alkanoyloxy having 1 to 4 carbon atoms, v) linear or branched alkoxy having 1 to 4 carbon atoms, (vi) linear or branched alkylenedioxy having 1 to 4 carbon atoms, (vii) carbon number Has 7 to 12 Aralkyloxy, (v
iii) linear or branched alkylthio having 1 to 4 carbons, (ix) linear or branched alkylsulfonyl having 1 to 4 carbons, (x) fluorine atom, (Xi) a chlorine atom, (xi
(xiii) aralkyl having 7 to 12 carbon atoms; (xiv) phenyl (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbon atoms; A straight-chain or branched alkyl halide having 4 carbon atoms, a straight-chain or branched alkoxy having 1 to 4 carbon atoms, a halogen or a straight-chain or branched alkyl having 1 to 4 carbon atoms or (Xv) phenoxy (where the phenyl moiety is a straight-chain or branched alkyl having 1 to 6 carbons, 1 to 6 carbons) Straight or branched alkyl halide having 4 carbon atoms, straight or branched alkoxy having 1 to 4 carbon atoms, halogen or 1 to 4 carbon atoms May be substituted by straight-chain or branched alkylenedioxy having.),
(Xvi) phenylthio, wherein the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons,
Straight or branched alkyl halide having 1 to 4 carbon atoms, straight or branched alkoxy having 1 to 4 carbon atoms, halogen or having 1 to 4 carbon atoms It may be substituted with a linear or branched alkylenedioxy. ), (Xv
ii) phenylsulfonyl (the phenyl moiety has 1 carbon atom)
Linear or branched alkyl having 1 to 4 carbon atoms, linear or branched alkyl halide having 1 to 4 carbon atoms, linear or branched alkyl having 1 to 4 carbon atoms, It may be substituted by a branched alkoxy, a halogen or a linear or branched alkylenedioxy having 1 to 4 carbon atoms. ),
(Xviii) phenylsulfonylamino (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl halide having 1 to 4 carbons) May be substituted by linear or branched alkoxy having 1 to 4 carbons, halogen, or linear or branched alkylenedioxy having 1 to 4 carbons. The nitrogen atom of the amino moiety may be substituted by a linear or branched alkyl having 1 to 6 carbon atoms.), (Xix) furyl, (xx) thienyl, (xxi) oxazolyl, (Xxii) isoxazolyl, (xxiii) thiazolyl, (xxi)
v) pyridyl, (xxv) pyridyloxy, (xx
vi) pyridylthio, (xxvii) pyridylsulfonyl, (xxviii) imidazolyl (the nitrogen atom of the ring may be substituted by linear or branched alkyl having 1 to 6 carbon atoms) and (xxi)
x) pyridylsulfonylamino, wherein the nitrogen atom of the amino moiety may be substituted by a straight-chain or branched alkyl having 1 to 6 carbon atoms. ; Y is an oxygen atom, in a sulfur atom or the formula> N-R ⁴ group having the formula (, R ⁴ is a hydrogen atom,
It represents a linear or branched alkyl group having 1 to 3 carbon atoms or a linear or branched alkanoyl group having 2 to 5 carbon atoms. ) Is a compound.

(31) R ¹ is a linear or branched alkyl group having 1 to 4 carbon atoms; R ² is a linear or branched alkyl group having 2 to 5 carbon atoms R ³ is a hydrogen atom; Z is a linear or branched alkylene group having 1 to 4 carbon atoms; W is (i) having 1 to 6 carbon atoms. A linear or branched alkyl group having (ii)
A straight-chain or branched alkoxy group having 1 to 4 carbon atoms, (iii) a straight-chain or branched alkylthio group having 1 to 4 carbon atoms, (i
v) a linear or branched monoalkylamino group having 1 to 4 carbon atoms; (v) a linear or branched alkyl group having the same or different and each alkyl having 1 to 4 carbon atoms. (Vi) a linear or branched alkyl and aryl moiety having 1 to 4 carbon atoms, which has 1 to 3 carbon atoms which may have a substituent α described later, which has 6 carbon atoms; An N-alkyl-N-arylamino group having an aryl having 1 to 10 aryl groups, and (vii) an aryl having 6 to 10 carbon atoms which may have 1 to 3 substituents α described below in the aryl portion. An oxy group, (viii) an arylthio group having 1 to 3 carbon atoms and 6 to 10 carbon atoms which may have a substituent α described later, and (i)
x) an arylamino group having 1 to 3 carbon atoms having 6 to 10 carbon atoms which may have 1 to 3 substituents α described later, and (x) 1 to 3 substituents α described later in the aryl moiety. 7 to 12 carbon atoms which may have
X is a phenyl group which may have one substituent α described later, wherein the substituent α is a hydroxy, chlorine atom, A compound selected from the group consisting of benzyl, phenyl, phenoxy, phenylthio, pyridyl, pyridyloxy and pyridylthio; Y is an oxygen atom;

(32) R ¹ is an alkyl group having 1 or 2 carbon atoms; R ² is an ethylene group; R ³ is a hydrogen atom; Z is a methylene group;
A propyl or butyl group, (ii) a linear or branched alkoxy group having 1 to 3 carbon atoms,
(Iii) a linear or branched alkylthio group having 1 to 3 carbon atoms, (iv) a linear or branched monoalkylamino group having 1 to 3 carbon atoms, (v ) A diethylamino group, (vi) N-
Phenyl-N-ethylamino group, (vii) phenoxy group, (viii) phenylthio group, (ix) phenylamino group, (x) 3-phenylpropyl group,
(Xi) 4-phenylbutyl group or (xii) 1-
A pyrrolyl group; X is a phenyl group optionally having one substituent α described below, wherein the substituent α is
Methyl, hydroxy, acetoxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl Or X is one pyridyl group optionally having a substituent α described below, wherein the substituent α is methoxy, ethoxy, isopropoxy, benzyloxy, having 1 to 2 carbon atoms Alkylthio, alkylsulfonyl having 1 or 2 carbon atoms,
Benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino and N-
A compound selected from the group consisting of methylphenylsulfonylamino; Y is an oxygen atom;

(33) R ¹ is an alkyl group having 1 or 2 carbon atoms; R ² is an ethylene group; R ³ is a hydrogen atom; Z is a methylene group;
A propyl or butyl group, (ii) a linear or branched alkoxy group having 1 to 3 carbon atoms,
(Iii) a linear or branched alkylthio group having 1 to 3 carbon atoms, (iv) a linear or branched monoalkylamino group having 1 to 3 carbon atoms, (v ) A diethylamino group, (vi) N-
Phenyl-N-ethylamino group, (vii) phenoxy group, (viii) phenylthio group, (ix) phenylamino group, (x) 3-phenylpropyl group,
(Xi) 4-phenylbutyl group or (xii) 1-
A pyrrolyl group; X is a phenyl group optionally having one substituent α described below, wherein the substituent α is
Hydroxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, pyridyl, pyridyloxy and
Y is selected from the group consisting of pyridylthio; Y
Is an oxygen atom; a compound.

(34) R ¹ is an alkyl group having 1 or 2 carbon atoms; R ² is an ethylene group; R ³ is a hydrogen atom; Z is a methylene group; W is a butyl group; Ethoxy, methylthio, ethylamino, diethylamino, N-phenyl-N-ethylamino, phenoxy, phenylthio, phenylamino, 3-
A phenylpropyl group or a 1-pyrrolyl group; X
Is a phenyl group which may have one substituent α described later, wherein the substituent α is a hydroxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio,
Pyridyl, pyridyloxy and pyridylthio; Y is an oxygen atom;
Compound.

(35) R ¹ is an alkyl group having 1 or 2 carbon atoms; R ² is an ethylene group; R ³ is a hydrogen atom; Z is a methylene group; W is a butyl group; Ethoxy, methylthio, ethylamino, phenoxy, phenylthio, phenylamino or
X is a phenyl group optionally having one substituent α described below, wherein the substituent α is a hydroxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, A compound selected from the group consisting of pyridyl, pyridyloxy and pyridylthio; Y is an oxygen atom;

Specific examples of the phenylalkylcarboxylic acid having the above general formula (I), its pharmaceutically acceptable salt or its pharmaceutically acceptable ester of the present invention include the following compounds. .

In Tables 1 to 68, abbreviations indicate the following groups.

Ac: acetyl, Bu: butyl, tBu:
t-butyl, Bimid: benzimidazolyl, Box
a: benzoxazolyl, Bthiz: benzothiazolyl, Bz: benzyl, Et: ethyl, Fur: furyl, Hex: hexyl, Imid: imidazolyl, In
d: indolyl, Isox: isoxazolyl, Md
O: methylenedioxy, Me: methyl, Mor: morpholino, Np: naphthyl, Oxa: oxazolyl, Pe
n: pentyl, Ph: phenyl, Pip: piperidinyl, Pr: propyl, iPr: isopropyl, Pym:
Pyrimidinyl, Pyr: pyridyl, Pyrd: pyrrolidinyl, Pyrr: pyrrolyl, Pyza: pyrazolyl, Q
uin: quinolyl, iQuin: isoquinolyl, Th
i: thienyl, Thiz: thiazolyl.

The compounds in Tables 1 to 55 and 66 to 68 have the following formula (Ia), and the compounds in Tables 56 to 65 have the following formula (Ib).

[0130]

Embedded image

[0131]

[Table 1] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 1-1 H (CH ₂ ) ₂ H CH ₂ OEt Ph O 1-2 H (CH ₂ ) ₂ H CH ₂ OEt 1-Np O 1-3 H (CH ₂ ) ₂ H CH ₂ OEt 2-Np O 1-4 H (CH ₂ ) ₂ H CH ₂ OEt 4-Me-Ph O 1-5 H (CH ₂ ) ₂ H CH ₂ OEt 4-Et-Ph O 1-6 H (CH ₂ ) ₂ H CH ₂ OEt 3-iPr-Ph O 1-7 H ( CH ₂ ) ₂ H CH ₂ OEt 4-iPr-Ph O 1-8 H (CH ₂ ) ₂ H CH ₂ OEt 3-tBu-Ph O 1-9 H (CH ₂ ) ₂ H CH ₂ OEt 4-tBu- Ph O 1-10 H (CH ₂ ) ₂ H CH ₂ OEt 3-Cl-Ph O 1-11 H (CH ₂ ) ₂ H CH ₂ OEt 4-Cl-Ph O 1-12 H (CH ₂ ) ₂ H CH ₂ OEt 3-Br-Ph O 1-13 H (CH ₂ ) ₂ H CH ₂ OEt 4-Br-Ph O 1-14 H (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-Ph O 1-15 H (CH ₂ ) ₂ H CH ₂ OEt 4-Ph-Ph O 1-16 H (CH ₂ ) ₂ H CH ₂ OEt 3-Bz-Ph O 1-17 H (CH ₂ ) ₂ H CH ₂ OEt 4- Bz-Ph O 1-18 H (CH ₂ ) ₂ H CH ₂ OEt 3-PhO-Ph O 1-19 H (CH ₂ ) ₂ H CH ₂ OEt 4-PhO-Ph O 1-20 H (CH ₂ ) ₂ H CH ₂ OEt 3-PhS-Ph O 1- 21 H (CH ₂ ) ₂ H CH ₂ OEt 4-PhS-Ph O 1-22 H ( CH ₂ ) ₂ H CH ₂ OEt 3-PhSO ₂ -Ph O 1-23 H (CH ₂ ) ₂ H CH ₂ OEt 4-PhSO ₂ -Ph O 1-24 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Imid-1) -Ph O 1-25 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Imid-1) -Ph O 1- 26 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Imid-4 ) -Ph O 1- 27 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Imid-4) -Ph O 1- 28 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Fur-2) -Ph O 1- 29 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Fur-2) -Ph O 1-30 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Thi-2) -Ph O 1- 31 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Thi-2) -Ph O 1- 32 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Thi-3) -Ph O 1-33 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Thi-3) -Ph O 1- 34 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-2) -Ph O 1- 35 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-2) -Ph O 1-36 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-3) -Ph O 1- 37 H (CH ₂ ) ₂ H CH ₂ OEt 4- ( Pyr-3) -Ph O 1- 38 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-4) -Ph O 1- 39 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-4) -Ph O 1- 40 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa-2) -Ph O 1-41 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-2) -Ph O 1 -42 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa-4) -Ph O 1- 43 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-4) -Ph O 1-44 H (CH ₂ ) ₂ H CH ₂ OEt 3 -(Oxa-5) -Ph O 1- 45 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-5) -Ph O 1- 46 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz- 2) -Ph O 1- 47 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-2) -Ph O 1- 48 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-4) -Ph O 1- 49 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-4) -Ph O 1-50 H (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-5) -Ph O 1-51 H (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-5) -Ph O 1- 52 H (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Pyrr O 1-53 H (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-2-Pyrr O 1- 54 H (CH ₂ ) ₂ H CH ₂ OEt 1-Bz-2-Pyrr O 1- 55 H (CH ₂ ) ₂ H CH ₂ OEt 5-Me- 2-Fur O 1-56 H (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-2-Fur O 1-57 H (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Thi O 1-58 H (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-2-Thi O 1- 59 H (CH ₂ ) ₂ H CH ₂ OEt 5-Me-3-Thi O 1-60 H (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-3-Thi O 1- 61 H (CH ₂ ) ₂ H CH ₂ OEt 1-Me-3-Pyza O 1- 62 H (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-3-Pyza O 1- 63 H (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Imid O 1- 64 H (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-2-Imid O 1- 65 H (CH ₂ ) ₂ H C H ₂ OEt 1-Me-4-Imid O 1- 66 H (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-4-Imid O 1- 67 H (CH ₂ ) ₂ H CH ₂ OEt 4-Oxa O 1 -68 H (CH ₂ ) ₂ H CH ₂ OEt 5-Oxa O 1-69 H (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Oxa O 1-70 H (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Oxa O 1- 71 H (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Oxa O 1- 72 H (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Oxa O 1- 73 H (CH ₂ ) ₂ H CH ₂ OEt 4-Me-2-Ph-5-Oxa O 1- 74 H (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Ph-4-Oxa O 1- 75 H (CH ₂ ) ₂ H CH ₂ OEt 4-Thiz O 1- 76 H (CH ₂ ) ₂ H CH ₂ OEt 5-Thiz O 1-77 H (CH ₂ ) ₂ H CH ₂ OEt 2-Me -4-Thiz O 1- 78 H (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Thiz O 1- 79 H (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Thiz O 1- 80 H (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Thiz O 1- 81 H (CH ₂ ) ₂ H CH ₂ OEt 4-Me-2-Ph-5-Thiz O 1-82 H (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Ph-4-Thiz O 1- 83 H (CH ₂ ) ₂ H CH ₂ OEt 1-Me-4-Pyza O 1- 84 H (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-4-Pyza O 1- 85 H (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Isox O 1- 86 H (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4- Isox O 1-87 H (CH ₂ ) ₂ H CH ₂ OEt 2-Pyr O 1-88 H (CH ₂ ) ₂ H CH ₂ OEt 3-Pyr O 1-89 H ( CH ₂ ) ₂ H CH ₂ OEt 4-Pyr O 1- 90 H (CH ₂ ) ₂ H CH ₂ OEt 3-Me-5-Pyr O 1- 91 H (CH ₂ ) ₂ H CH ₂ OEt 3-Et- 5-Pyr O 1- 92 H (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-5-Pyr O 1- 93 H (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Pyr O 1- 94 H (CH ₂ ) ₂ H CH ₂ OEt 2-Et-5-Pyr O 1- 95 H (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Pyr O 1- 96 H (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-5-Pyr O 1-97 H (CH ₂ ) ₂ H CH ₂ OEt 2-EtO-5-Pyr O 1-98 H (CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-5-Pyr O 1- 99 H (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-5-Pyr O 1-100 H (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-5-Pyr O 1-101 H (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS-5-Pyr O 1-102 H (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pyr O 1-103 H (CH ₂ ) ₂ H CH ₂ OEt 2 -EtSO ₂ -5-Pyr O 1-104 H (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pyr O 1-105 H (CH ₂ ) ₂ H CH ₂ OEt 2-Bz-5-Pyr O 1-106 H (CH ₂ ) ₂ H CH ₂ OEt 2-PhO-5-Pyr O 1-107 H (CH ₂ ) ₂ H CH ₂ OEt 2-PhS-5-Pyr O 1-108 H (CH ₂ ) ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pyr O 1-109 H (CH ₂ ) ₂ H CH ₂ OEt 3-Me-6-Pyr O 1-110 H (CH ₂ ) ₂ H CH ₂ OEt 3 -Ph-6-Pyr O 1-111 H (CH ₂ ) ₂ H CH ₂ OEt 2-Me-6-Pyr O 1-112 H (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-6-Pyr O 1-113 H (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Pym O 1-114 H (CH ₂ ) ₂ H CH ₂ OEt 2-Ph- 4-Pym O 1-115 H (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-4-Pym O 1-116 H (CH ₂ ) ₂ H CH ₂ OEt 2-EtO-4-Pym O 1-117 H (CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-4-Pym O 1-118 H (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-4-Pym O 1-119 H (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-4-Pym O 1-120 H (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS-4-Pym O 1-121 H (CH ₂ ) ₂ H CH ₂ OEt 6-MeS-4-Pym O 1-122 H (CH ₂ ) ₂ H CH ₂ OEt 6-EtS-4-Pym O 1-123 H (CH ₂ ) ₂ H CH ₂ OEt 6-iPrS-4-Pym O 1-124 H (CH ₂ ) ₂ H CH ₂ OEt 2-PhS-4-Pym O 1-125 H (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -4-Pym O 1-126 H (CH ₂ ) ₂ H CH ₂ OEt 2 -EtSO ₂ -4-Pym O 1-127 H (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -4-Pym O 1-128 H (CH ₂ ) ₂ H CH ₂ OEt 2-PhSO ₂ -4- Pym O 1-129 H (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Pym O 1-130 H (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Pym O 1-131 H (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-5-Pym O 1-132 H (CH ₂ ) ₂ H CH ₂ OEt 2-EtO-5-Pym O 1-133 H (CH ₂ ) ₂ H CH ₂ OEt 2 -iPrO-5-Pym O 1-134 H (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-5-Pym O 1-135 H (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-5-Pym O 1-136 H (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS-5-Pym O 1-137 H (CH ₂ ) ₂ H CH ₂ OEt 2 -PhS-5-Pym O 1-138 H (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pym O 1-139 H (CH ₂ ) ₂ H CH ₂ OEt 2-EtSO ₂ -5-Pym O 1-140 H (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pym O 1-141 H (CH ₂ ) ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pym O 1-142 H ( CH ₂ ) ₂ H CH ₂ OEt 2-Ind O 1-143 H (CH ₂ ) ₂ H CH ₂ OEt 3-Ind O 1-144 H (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Ind O 1-145 H (CH ₂ ) ₂ H CH ₂ OEt 1-Me-3-Ind O 1-146 H (CH ₂ ) ₂ H CH ₂ OEt 2-Bimid O 1-147 H (CH ₂ ) ₂ H CH ₂ OEt 2-Boxa O 1-148 H (CH ₂ ) ₂ H CH ₂ OEt 2-Bthiz O 1-149 H (CH ₂ ) ₂ H CH ₂ OEt 2-Quin O 1-150 H (CH ₂ ) ₂ H CH ₂ OEt 3-Quin O 1-151 H (CH ₂ ) ₂ H CH ₂ OEt 4-Quin O 1-152 H (CH ₂ ) ₂ H CH ₂ OEt 1-iQuin O 1-153 H (CH ₂ ) ₂ H CH ₂ OEt 3-iQuin O 1-154 H (CH ₂ ) ₂ H CH ₂ OEt 4-iQuin O 1-155 H (CH ₂ ) ₂ H CH ₂ OEt 3-MeO-Ph O 1-156 H (CH ₂ ) ₂ H CH ₂ OEt 4-MeO-Ph O 1-157 H (CH ₂ ) ₂ H CH ₂ OEt 3-EtO-Ph O 1-158 H (CH ₂ ) ₂ H CH ₂ OEt 4-EtO-Ph O 1-159 H (CH ₂ ) ₂ H CH ₂ OEt 3-iPrO-Ph O 1-160 H (CH ₂ ) ₂ H CH ₂ OEt 4-iPrO-Ph O 1-161 H (CH ₂ ) ₂ H CH ₂ OEt 3-MeS-Ph O 1-162 H (CH ₂ ) ₂ H CH ₂ OEt 4-MeS-Ph O 1-163 H (CH ₂ ) ₂ H CH ₂ OEt 3-EtS-Ph O 1-164 H (CH ₂ ) ₂ H CH ₂ OEt 4-EtS-Ph O 1-165 H (CH ₂ ) ₂ H CH ₂ OEt 3-iPrS-Ph O 1-166 H (CH ₂ ) ₂ H CH ₂ OEt 4-iPrS-Ph O 1-167 H (CH ₂ ) ₂ H CH ₂ OEt 3-MeSO ₂ -Ph O 1-168 H (CH ₂ ) ₂ H CH ₂ OEt 4-MeSO ₂ -Ph O 1-169 H (CH ₂ ) ₂ H CH ₂ OEt 3-EtSO ₂ -Ph O 1 -170 H (CH ₂ ) ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 1-171 H (CH ₂ ) ₂ H CH ₂ OEt 3-iPrSO ₂ -Ph O 1-172 H (CH ₂ ) ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 1-173 H (CH ₂ ) ₂ H CH ₂ OEt 3- (1-Me-Imid-4) -Ph O 1-174 H (CH ₂ ) ₂ H CH ₂ OEt 4 -(1-Me-Imid-4) -Ph O 1-175 H (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Ph-4-Imid O 1-176 H (CH ₂ ) ₂ H CH ₂ OEt 1,4-di-Me-2-Ph-5-Imid O 1-177 H (CH ₂ ) ₂ H CH ₂ OEt 1,5-di-Me-2-Ph-4-Imid O 1-178 H (CH ₂ ) ₂ H CH ₂ OEt 3,4-MdO-Ph O 1-179 H (CH ₂ ) ₂ H CH ₂ OEt 4- (4-MeO-Ph) -Ph O 1-180 H (CH ₂ ) ₂ H CH ₂ OEt 4- (3,4-MdO-Ph) -Ph O 1-181 H (CH ₂ ) ₂ H CH ₂ OEt 4- [PhSO ₂ N (Me)]- Ph O 1-182 H (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ N (Me)]-Ph O 1-183 H (CH ₂ ) ₂ H CH ₂ OEt 4- (PhSO ₂ NH) -Ph O 1-184 H (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ NH] -Ph O 1-185 H (CH ₂ ) ₂ H CH ₂ OEt 4- [ (Pyr-2) SO ₂ ] -Ph O 1-186 H (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ ] -Ph O 1-187 H (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ N (Me)]-Ph O 1-188 H (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ NH] -Ph O 1-189 H (CH ₂ ) ₂ H CH ₂ OEt 4- (4-Me-Ph) -Ph O 1-190 H (CH ₂ ) ₂ H CH ₂ OEt 4- (4-F-Ph) -Ph O 1-191 H (CH ₂ ) ₂ H CH ₂ OEt 4- (4-CF ₃ -Ph) -Ph O 1-192 H (CH ₂ ) ₂ H CH ₂ OEt 2- [4-Me-PhSO ₂ N (Me)] -5-Pyr O 1-193 H (CH ₂ ) ₂ H CH ₂ OEt 2-HO-5-Pyr O 1-194 H (CH ₂ ) ₂ H CH ₂ OEt 2-BzO-5-Pyr O 1-195 H (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-4) SO ₂ ] -Ph O 1-196 H (CH ₂ ) ₂ H CH ₂ OEt 4- (2,4-di-MeO-Ph) -Ph O 1-197 H (CH ₂ ) ₂ H CH ₂ OEt 4- (2,5-di-MeO-Ph) -Ph O 1-198 H (CH ₂ ) ₂ H CH ₂ OEt 3-HO-Ph O 1-199 H (CH ₂ ) ₂ H CH ₂ OEt 4-HO-Ph O 1-200 H (CH ₂ ) ₂ H CH ₂ OEt 5-AcO-2-HO-3,4,6-tri-Me -Ph O 1-201 H (CH ₂ ) ₂ H CH ₂ OEt 4-HO-3,5-di-Me-Ph O 1-2 02 H (CH ₂ ) ₂ H CH ₂ OEt 3-AcO-Ph O 1-203 H (CH ₂ ) ₂ H CH ₂ OEt 4-AcO-Ph O ────────────── ────────────────────.

[0132]

[Table 2] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 2-1 Me (CH ₂ ) ₂ H CH ₂ OEt Ph O 2-2 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Np O 2-3 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Np O 2- 4 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Me-Ph O 2- 5 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Et-Ph O 2- 6 Me (CH ₂ ) ₂ H CH ₂ OEt 3-iPr-Ph O 2- 7 Me ( CH ₂ ) ₂ H CH ₂ OEt 4-iPr-Ph O 2- 8 Me (CH ₂ ) ₂ H CH ₂ OEt 3-tBu-Ph O 2- 9 Me (CH ₂ ) ₂ H CH ₂ OEt 4-tBu- Ph O 2- 10 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Cl-Ph O 2- 11 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Cl-Ph O 2- 12 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Br-Ph O 2-13 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Br-Ph O 2-14 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-Ph O 2-15 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Ph-Ph O 2- 16 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Bz-Ph O 2- 17 Me (CH ₂ ) ₂ H CH ₂ OEt 4- Bz-Ph O 2- 18 Me (CH ₂ ) ₂ H CH ₂ OEt 3-PhO-Ph O 2- 19 Me (CH ₂ ) ₂ H CH ₂ OEt 4-PhO-Ph O 2- 20 Me (CH ₂ ) ₂ H CH ₂ OEt 3-PhS-Ph O 2- 21 Me (CH ₂ ) ₂ H CH ₂ OEt 4- PhS-Ph O 2- 22 Me (CH ₂ ) ₂ H CH ₂ OEt 3-PhSO ₂ -Ph O 2- 23 Me (CH ₂ ) ₂ H CH ₂ OEt 4-PhSO ₂ -Ph O 2- 24 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Imid-1) -Ph O 2- 25 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Imid-1) -Ph O 2-26 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Imid-4) -Ph O 2-27 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Imid-4) -Ph O 2-28 Me (CH ₂ ) ₂ H CH ₂ OEt 3 -(Fur-2) -Ph O 2- 29 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Fur-2) -Ph O 2- 30 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Thi- 2) -Ph O 2- 31 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Thi-2) -Ph O 2- 32 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Thi-3) -Ph O 2- 33 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Thi-3) -Ph O 2- 34 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-2) -Ph O 2- 35 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-2) -Ph O 2-36 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-3) -Ph O 2-37 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-3) -Ph O 2-38 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-4) -Ph O 2-39 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-4) -Ph O 2- 40 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa-2) -Ph O 2- 41 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-2) -Ph O 2- 42 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa-4) -Ph O 2-43 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-4) -Ph O 2-44 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa-5) -Ph O 2-45 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-5 ) -Ph O 2-46 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-2) -Ph O 2-47 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-2) -Ph O 2-48 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-4) -Ph O 2-49 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-4) -Ph O 2- 50 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-5) -Ph O 2- 51 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-5) -Ph O 2-52 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Pyrr O 2-53 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-2-Pyrr O 2-54 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Bz -2-Pyrr O 2-55 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Fur O 2-56 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-2-Fur O 2- 57 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Thi O 2-58 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-2-Thi O 2-59 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Me-3-Thi O 2- 60 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-3-Thi O 2- 61 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Me-3- Pyza O 2- 62 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-3-Pyza O 2- 63 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Imid O 2 -64 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-2-Imid O 2- 65 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Me-4-Imid O 2- 66 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-4-Imid O 2-67 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Oxa O 2-68 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Oxa O 2-69 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Oxa O 2-70 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Oxa O 2- 71 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Oxa O 2-72 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Oxa O 2-73 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Me-2-Ph -5-Oxa O 2- 74 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Ph-4-Oxa O 2- 75 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Thiz O 2- 76 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Thiz O 2-77 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Thiz O 2- 78 Me (CH ₂ ) ₂ H CH ₂ OEt 2- Ph-4-Thiz O 2- 79 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Thiz O 2- 80 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Thiz O 2- 81 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Me-2-Ph-5-Thiz O 2- 82 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Ph-4-Thiz O 2- 83 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Me-4-Pyza O 2- 84 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-4-Pyza O 2- 85 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Isox O 2- 86 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Isox O 2-87 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Pyr O 2-88 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Pyr O 2-89 Me (CH ₂ ) ₂ H CH ₂ OEt 4- Pyr O 2- 90 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Me-5-Pyr O 2- 91 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Et-5-Pyr O 2- 92 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-5-Pyr O 2- 93 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Pyr O 2- 94 Me (CH ₂ ) ₂ H CH ₂ OEt 2 -Et-5-Pyr O 2- 95 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Pyr O 2- 96 Me (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-5-Pyr O 2 -97 Me (CH ₂ ) ₂ H CH ₂ OEt 2-EtO-5-Pyr O 2- 98 Me (CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-5-Pyr O 2- 99 Me (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-5-Pyr O 2-100 Me (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-5-Pyr O 2-101 Me (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS- 5-Pyr O 2-102 Me (CH 2) 2 H CH 2 OEt 2-MeSO 2 -5-Pyr O 2-103 Me (CH 2) 2 H CH 2 OEt 2-EtSO 2 -5-Pyr O 2- 104 Me (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pyr O 2-105 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Bz-5-Pyr O 2-106 Me (CH ₂ ) ₂ H CH ₂ OEt 2-PhO-5-Pyr O 2-107 Me (CH ₂ ) ₂ H CH ₂ OEt 2-PhS-5-Pyr O 2-108 Me (CH ₂ ) ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pyr O 2-109 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Me- 6-Pyr O 2-110 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-6-Pyr O 2-111 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Me-6-Pyr O 2-112 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-6-Pyr O 2-113 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Pym O 2-114 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Pym O 2-115 Me (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-4-Pym O 2-116 Me (CH ₂ ) ₂ H CH ₂ OEt 2-EtO-4-Pym O 2-117 Me (CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-4-Pym O 2-118 Me (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-4-Pym O 2-119 Me (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-4-Pym O 2-120 Me (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS-4-Pym O 2-121 Me (CH ₂ ) ₂ H CH ₂ OEt 6- MeS-4-Pym O 2-122 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtS-4-Pym O 2-123 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrS-4-Pym O 2- 124 Me (CH ₂ ) ₂ H CH ₂ OEt 2-PhS-4-Pym O 2-125 Me (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -4-Pym O 2-126 Me (CH ₂ ) ₂ H CH ₂ OEt 2-EtSO ₂ -4-Pym O 2-127 Me (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -4-Pym O 2-128 Me (CH ₂ ) ₂ H CH ₂ OEt 2- PhSO ₂ -4-Pym O 2-129 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Pym O 2-130 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Pym O 2 -131 Me (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-5-Pym O 2-132 Me (C H ₂ ) ₂ H CH ₂ OEt 2-EtO-5-Pym O 2-133 Me (CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-5-Pym O 2-134 Me (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-5-Pym O 2-135 Me (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-5-Pym O 2-136 Me (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS-5-Pym O 2-137 Me (CH ₂ ) ₂ H CH ₂ OEt 2-PhS-5-Pym O 2-138 Me (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pym O 2-139 Me (CH ₂ ) ₂ H CH ₂ OEt 2-EtSO ₂ -5-Pym O 2-140 Me (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pym O 2-141 Me (CH ₂ ) ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pym O 2-142 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Ind O 2-143 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ind O 2-144 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Ind O 2-145 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Me-3-Ind O 2-146 Me (CH ₂ ) ₂ H CH ₂ OEt 2- Bimid O 2-147 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Boxa O 2-148 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Bthiz O 2-149 Me (CH ₂ ) ₂ H CH ₂ OEt 2 -Quin O 2-150 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Quin O 2-151 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Quin O 2-152 Me (CH ₂ ) ₂ H CH ₂ OEt 1-iQuin O 2-153 Me (CH ₂ ) ₂ H CH ₂ OEt 3-iQuin O 2-154 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iQuin O 2-155 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Me O-Ph O 2-156 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeO-Ph O 2-157 Me (CH ₂ ) ₂ H CH ₂ OEt 3-EtO-Ph O 2-158 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtO-Ph O 2-159 Me (CH ₂ ) ₂ H CH ₂ OEt 3-iPrO-Ph O 2-160 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrO-Ph O 2 -161 Me (CH ₂ ) ₂ H CH ₂ OEt 3-MeS-Ph O 2-162 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeS-Ph O 2-163 Me (CH ₂ ) ₂ H CH ₂ OEt 3-EtS-Ph O 2-164 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtS-Ph O 2-165 Me (CH ₂ ) ₂ H CH ₂ OEt 3-iPrS-Ph O 2-166 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrS-Ph O 2-167 Me (CH ₂ ) ₂ H CH ₂ OEt 3-MeSO ₂ -Ph O 2-168 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeSO ₂ -Ph O 2-169 Me (CH ₂ ) ₂ H CH ₂ OEt 3-EtSO ₂ -Ph O 2-170 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 2-171 Me (CH ₂ ) ₂ H CH ₂ OEt 3-iPrSO ₂ -Ph O 2-172 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 2-173 Me (CH ₂ ) ₂ H CH ₂ OEt 3- (1 -Me-Imid-4) -Ph O 2-174 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (1-Me-Imid-4) -Ph O 2-175 Me (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Ph-4-Imid O 2-176 Me (CH ₂ ) ₂ H CH ₂ OEt 1,4-di-Me-2-Ph-5-Imid O 2-177 Me (CH ₂ ) ₂ H CH ₂ OEt 1,5-di-Me-2-Ph-4-Imid O 2-178 M e (CH ₂ ) ₂ H CH ₂ OEt 3,4-MdO-Ph O 2-179 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (4-MeO-Ph) -Ph O 2-180 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (3,4-MdO-Ph) -Ph O 2-181 Me (CH ₂ ) ₂ H CH ₂ OEt 4- [PhSO ₂ N (Me)]-Ph O 2-182 Me (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ N (Me)]-Ph O 2-183 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (PhSO ₂ NH) -Ph O 2-184 Me (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ NH] -Ph O 2-185 Me (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ ] -Ph O 2-186 Me (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ ] -Ph O 2-187 Me (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr -2) SO ₂ N (Me)]-Ph O 2-188 Me (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ NH] -Ph O 2-189 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (4-Me-Ph) -Ph O 2-190 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (4-F-Ph) -Ph O 2-191 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (4-CF ₃ -Ph) -Ph O 2-192 Me (CH ₂ ) ₂ H CH ₂ OEt 2- [4-Me-PhSO ₂ N (Me)]-5-Pyr O 2 -193 Me (CH ₂ ) ₂ H CH ₂ OEt 2-HO-5-Pyr O 2-194 Me (CH ₂ ) ₂ H CH ₂ OEt 2-BzO-5-Pyr O 2-195 Me (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-4) SO ₂ ] -Ph O 2-196 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (2,4-di-MeO-Ph) -Ph O 2-197 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (2,5-di-MeO- Ph) -Ph O 2-198 Me (CH ₂ ) ₂ H CH ₂ OEt 3-HO-Ph O 2-199 Me (CH ₂ ) ₂ H CH ₂ OEt 4-HO-Ph O 2-200 Me (CH ₂ ) ₂ H CH ₂ OEt 5-AcO-2-HO-3,4,6-tri-Me-Ph O 2-201 Me (CH ₂ ) ₂ H CH ₂ OEt 4-HO-3,5-di-Me -Ph O 2-202 Me (CH ₂ ) ₂ H CH ₂ OEt 3-AcO-Ph O 2-203 Me (CH ₂ ) ₂ H CH ₂ OEt 4-AcO-Ph O ───────── ─────────────────────────.

[0133]

[Table 3] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 3-1 Et (CH ₂ ) ₂ H CH ₂ OEt Ph O 3- 2 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Np O 3- 3 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Np O 3- 4 Et (CH ₂ ) ₂ H CH ₂ OEt 4-Me-Ph O 3-5 Et (CH ₂ ) ₂ H CH ₂ OEt 4-Et-Ph O 3-6 Et (CH ₂ ) ₂ H CH ₂ OEt 3-iPr-Ph O 3-7 Et ( CH ₂ ) ₂ H CH ₂ OEt 4-iPr-Ph O 3-8 Et (CH ₂ ) ₂ H CH ₂ OEt 3-tBu-Ph O 3-9 Et (CH ₂ ) ₂ H CH ₂ OEt 4-tBu- Ph O 3-10 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Cl-Ph O 3-11 Et (CH ₂ ) ₂ H CH ₂ OEt 4-Cl-Ph O 3-12 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Br-Ph O 3-13 Et (CH ₂ ) ₂ H CH ₂ OEt 4-Br-Ph O 3-14 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-Ph O 3-15 Et (CH ₂ ) ₂ H CH ₂ OEt 4-Ph-Ph O 3-16 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Bz-Ph O 3-17 Et (CH ₂ ) ₂ H CH ₂ OEt 4- Bz-Ph O 3--18 Et (CH ₂ ) ₂ H CH ₂ OEt 3-PhO-Ph O 3-19 _{Et (CH 2) 2 H CH} 2 OEt 4-PhO-Ph O 3- 20 Et (CH 2) 2 H CH 2 OEt 3-PhS-Ph O 3- 21 Et (CH 2) 2 H CH 2 OEt 4- PhS-Ph O 3-22 Et (CH ₂ ) ₂ H CH ₂ OEt 3-PhSO ₂ -Ph O 3-23 Et (CH ₂ ) ₂ H CH ₂ OEt 4-PhSO ₂ -Ph O 3-24 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Imid-1) -Ph O 3-25 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Imid-1) -Ph O 3-26 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Imid-4) -Ph O 3-27 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Imid-4) -Ph O 3-28 Et (CH ₂ ) ₂ H CH ₂ OEt 3 -(Fur-2) -Ph O 3- 29 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Fur-2) -Ph O 3-30 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Thi- 2) -Ph O 3-31 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Thi-2) -Ph O 3-32 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Thi-3) -Ph O 3-33 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Thi-3) -Ph O 3-34 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-2) -Ph O 3-35 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-2) -Ph O 3-36 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-3) -Ph O 3-37 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-3) -Ph O 3-38 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-4) -Ph O 3-39 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-4) -Ph O 3-40 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa-2) -Ph O 3-41 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-2) -Ph O 3-42 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa-4) -Ph O 3-43 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-4) -Ph O 3-44 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa-5) -Ph O 3-45 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-5 ) -Ph O 3-46 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-2) -Ph O 3-47 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-2) -Ph O 3-48 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-4) -Ph O 3-49 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-4) -Ph O 3- 50 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-5) -Ph O 3-51 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-5) -Ph O 3-52 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Pyrr O 3-53 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-2-Pyrr O 3-54 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Bz -2-Pyrr O 3-55 Et (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Fur O 3-56 Et (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-2-Fur O 3- 57 Et (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Thi O 3-58 Et (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-2-Thi O 3-59 Et (CH ₂ ) ₂ H CH ₂ OEt 5-Me-3-Thi O 3- 60 Et (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-3-Thi O 3- 61 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Me-3- Pyza O 3-62 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-3-Pyza O 3-63 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Imid O 3 -64 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-2-Imid O 3-65 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Me-4-Imid O 3- 66 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-4-Imid O 3-67 Et (CH ₂ ) ₂ H CH ₂ OEt 4-Oxa O 3-68 Et (CH ₂ ) ₂ H CH ₂ OEt 5-Oxa O 3-69 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Oxa O 3-70 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Oxa O 3-71 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Oxa O 3-72 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Oxa O 3-73 Et (CH ₂ ) ₂ H CH ₂ OEt 4-Me-2-Ph -5-Oxa O 3- 74 Et (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Ph-4-Oxa O 3- 75 Et (CH ₂ ) ₂ H CH ₂ OEt 4-Thiz O 3- 76 Et (CH ₂ ) ₂ H CH ₂ OEt 5-Thiz O 3-77 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Thiz O 3-78 Et (CH ₂ ) ₂ H CH ₂ OEt 2- Ph-4-Thiz O 3- 79 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Thiz O 3-80 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Thiz O 3- 81 Et (CH ₂ ) ₂ H CH ₂ OEt 4-Me-2-Ph-5-Thiz O 3- 82 Et (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Ph-4-Thiz O 3- 83 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Me-4-Pyza O 3- 84 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-4-Pyza O 3-85 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Isox O 3-86 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Isox O 3-87 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Pyr O 3-88 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Pyr O 3-89 Et (CH ₂ ) ₂ H CH ₂ OEt 4- Pyr O 3-90 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Me-5-Pyr O 3-91 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Et-5-Pyr O 3-92 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-5-Pyr O 3-93 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Pyr O 3-94 Et (CH ₂ ) ₂ H CH ₂ OEt 2 -Et-5-Pyr O 3- 95 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Pyr O 3- 96 Et (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-5-Pyr O 3 -97 Et (CH ₂ ) ₂ H CH ₂ OEt 2-EtO-5-Pyr O 3-98 Et (CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-5-Pyr O 3- 99 Et (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-5-Pyr O 3-100 Et (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-5-Pyr O 3-101 Et (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS- 5-Pyr O 3-102 Et (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pyr O 3-103 Et (CH ₂ ) ₂ H CH ₂ OEt 2-EtSO ₂ -5-Pyr O 3- 104 Et (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pyr O 3-105 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Bz-5-Pyr O 3-106 Et (CH ₂ ) ₂ H CH ₂ OEt 2-PhO-5-Pyr O 3-107 Et (CH ₂ ) ₂ H CH ₂ OEt 2-PhS-5-Pyr O 3-108 Et (CH ₂ ) ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pyr O 3-109 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Me- 6-Pyr O 3-110 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-6-Pyr O 3-111 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Me-6-Pyr O 3-112 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-6-Pyr O 3-113 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Pym O 3-114 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Pym O 3-115 Et (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-4-Pym O 3-116 Et (CH ₂ ) ₂ H CH ₂ OEt 2-EtO-4-Pym O 3-117 Et (CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-4-Pym O 3-118 Et (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-4-Pym O 3-119 Et (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-4-Pym O 3-120 Et (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS-4-Pym O 3-121 Et (CH ₂ ) ₂ H CH ₂ OEt 6- MeS-4-Pym O 3-122 Et (CH ₂ ) ₂ H CH ₂ OEt 6-EtS-4-Pym O 3-123 Et (CH ₂ ) ₂ H CH ₂ OEt 6-iPrS-4-Pym O 3- 124 Et (CH ₂ ) ₂ H CH ₂ OEt 2-PhS-4-Pym O 3-125 Et (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -4-Pym O 3-126 Et (CH ₂ ) ₂ H CH ₂ OEt 2-EtSO ₂ -4-Pym O 3-127 Et (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -4-Pym O 3-128 Et (CH ₂ ) ₂ H CH ₂ OEt 2- PhSO ₂ -4-Pym O 3-129 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Pym O 3-130 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Pym O 3 -131 Et (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-5-Pym O 3-132 Et (C H ₂ ) ₂ H CH ₂ OEt 2-EtO-5-Pym O 3-133 Et (CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-5-Pym O 3-134 Et (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-5-Pym O 3-135 Et (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-5-Pym O 3-136 Et (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS-5-Pym O 3-137 Et (CH ₂ ) ₂ H CH ₂ OEt 2-PhS-5-Pym O 3-138 Et (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pym O 3-139 Et (CH ₂ ) ₂ H CH ₂ OEt 2-EtSO ₂ -5-Pym O 3-140 Et (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pym O 3-141 Et (CH ₂ ) ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pym O 3-142 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Ind O 3-143 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Ind O 3-144 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Ind O 3-145 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Me-3-Ind O 3-146 Et (CH ₂ ) ₂ H CH ₂ OEt 2- Bimid O 3-147 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Boxa O 3-148 Et (CH ₂ ) ₂ H CH ₂ OEt 2-Bthiz O 3-149 Et (CH ₂ ) ₂ H CH ₂ OEt 2 -Quin O 3-150 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Quin O 3-151 Et (CH ₂ ) ₂ H CH ₂ OEt 4-Quin O 3-152 Et (CH ₂ ) ₂ H CH ₂ OEt 1-iQuin O 3-153 Et (CH ₂ ) ₂ H CH ₂ OEt 3-iQuin O 3-154 Et (CH ₂ ) ₂ H CH ₂ OEt 4-iQuin O 3-155 Et (CH ₂ ) ₂ H CH ₂ OEt 3-Me O-Ph O 3-156 Et (CH ₂ ) ₂ H CH ₂ OEt 4-MeO-Ph O 3-157 Et (CH ₂ ) ₂ H CH ₂ OEt 3-EtO-Ph O 3-158 Et (CH ₂ ) ₂ H CH ₂ OEt 4-EtO-Ph O 3-159 Et (CH ₂ ) ₂ H CH ₂ OEt 3-iPrO-Ph O 3-160 Et (CH ₂ ) ₂ H CH ₂ OEt 4-iPrO-Ph O 3 -161 Et (CH ₂ ) ₂ H CH ₂ OEt 3-MeS-Ph O 3-162 Et (CH ₂ ) ₂ H CH ₂ OEt 4-MeS-Ph O 3-163 Et (CH ₂ ) ₂ H CH ₂ OEt 3-EtS-Ph O 3-164 Et (CH ₂ ) ₂ H CH ₂ OEt 4-EtS-Ph O 3-165 Et (CH ₂ ) ₂ H CH ₂ OEt 3-iPrS-Ph O 3-166 Et (CH ₂ ) ₂ H CH ₂ OEt 4-iPrS-Ph O 3-167 Et (CH ₂ ) ₂ H CH ₂ OEt 3-MeSO ₂ -Ph O 3-168 Et (CH ₂ ) ₂ H CH ₂ OEt 4-MeSO ₂ -Ph O 3-169 Et (CH ₂ ) ₂ H CH ₂ OEt 3-EtSO ₂ -Ph O 3-170 Et (CH ₂ ) ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 3-171 Et (CH ₂ ) ₂ H CH ₂ OEt 3-iPrSO ₂ -Ph O 3-172 Et (CH ₂ ) ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 3-173 Et (CH ₂ ) ₂ H CH ₂ OEt 3- (1 -Me-Imid-4) -Ph O 3-174 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (1-Me-Imid-4) -Ph O 3-175 Et (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Ph-4-Imid O 3-176 Et (CH ₂ ) ₂ H CH ₂ OEt 1,4-di-Me-2-Ph-5-Imid O 3-177 Et (CH ₂ ) ₂ H CH ₂ OEt 1,5-di-Me-2-Ph-4-Imid O 3-178 E t (CH ₂ ) ₂ H CH ₂ OEt 3,4-MdO-Ph O 3-179 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (4-MeO-Ph) -Ph O 3-180 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (3,4-MdO-Ph) -Ph O 3-181 Et (CH ₂ ) ₂ H CH ₂ OEt 4- [PhSO ₂ N (Me)]-Ph
O 3-182 Et (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ N (Me)]-Ph O 3-183 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (PhSO ₂ NH) -Ph O 3-184 Et (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ NH] -Ph O 3-185 Et (CH ₂ ) ₂ H CH ₂ OEt 4-[( Pyr-2) SO ₂ ] -Ph O 3-186 Et (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ ] -Ph O 3-187 Et (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ N (Me)]-Ph O 3-188 Et (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ NH] -Ph O 3-189 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (4-Me-Ph) -Ph O 3-190 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (4-F-Ph) -Ph O 3-191 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (4-CF ₃ -Ph) -Ph O 3-192 Et (CH ₂ ) ₂ H CH ₂ OEt 2- [4-Me-PhSO ₂ N (Me)]- 5-Pyr O 3-193 Et (CH ₂ ) ₂ H CH ₂ OEt 2-HO-5-Pyr O 3-194 Et (CH ₂ ) ₂ H CH ₂ OEt 2-BzO-5-Pyr O 3-195 Et (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-4) SO ₂ ] -Ph O 3-196 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (2,4-di-MeO-Ph)- Ph O 3-197 Et (CH ₂ ) ₂ H CH ₂ OEt 4- (2,5-di-MeO-Ph) -Ph O 3-198 Et (CH ₂ ) ₂ H CH ₂ OEt 3-HO-Ph O 3-199 Et (CH ₂ ) ₂ H CH ₂ OEt 4-HO-Ph O 3-200 Et (CH ₂ ) ₂ H CH ₂ OEt 5-AcO-2-HO-3,4,6-tri-Me- Ph O 3-201 Et (CH ₂ ) ₂ H CH ₂ OEt 4-HO-3 , 5-di-Me-Ph O 3-202 Et (CH ₂ ) ₂ H CH ₂ OEt 3-AcO-Ph O 3-203 Et (CH ₂ ) ₂ H CH ₂ OEt 4-AcO-Ph O ─── ───────────────────────────────.

[0134]

[Table 4] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 4- 1 iPr (CH ₂ ) ₂ H CH ₂ OEt Ph O 4- 2 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Np O 4- 3 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Np O 4- 4 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Me-Ph O 4- 5 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Et-Ph O 4- 6 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-iPr-Ph O 4- 7 iPr ( CH ₂ ) ₂ H CH ₂ OEt 4-iPr-Ph O 4- 8 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-tBu-Ph O 4- 9 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-tBu- Ph O 4- 10 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Cl-Ph O 4- 11 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Cl-Ph O 4- 12 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Br-Ph O 4- 13 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Br-Ph O 4- 14 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-Ph O 4- 15 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Ph-Ph O 4- 16 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Bz-Ph O 4- 17 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- Bz-Ph O 4- 18 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-PhO-Ph O 4- 19 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-PhO-Ph O 4--20 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-PhS-Ph O 4- 21 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-PhS-Ph O 4- 22 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-PhSO ₂ -Ph O 4- 23 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-PhSO ₂ -Ph O 4- 24 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Imid-1) -Ph O 4- 25 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Imid-1) -Ph O 4 -26 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Imid-4) -Ph O 4-27 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Imid-4) -Ph O 4-28 iPr ( CH ₂ ) ₂ H CH ₂ OEt 3- (Fur-2) -Ph O 4-29 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Fur-2) -Ph O 4- 30 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Thi-2) -Ph O 4-31 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Thi-2) -Ph O 4-32 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Thi-3) -Ph O 4-33 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Thi-3) -Ph O 4- 34 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr -2) -Ph O 4-35 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-2) -Ph O 4-36 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-3)- Ph O 4- 37 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-3) -Ph O 4- 38 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Pyr-4) -Ph O 4- 39 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-4) -Ph O 4-40 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa-2) -Ph O 4-41 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-2) -Ph O 4-42 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa -4) -Ph O 4-43 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-4) -Ph O 4-44 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Oxa-5)- Ph O 4- 45 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Oxa-5) -Ph O 4- 46 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-2) -Ph O 4- 47 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-2) -Ph O 4-48 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-4) -Ph O 4-49 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-4) -Ph O 4- 50 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (Thiz-5) -Ph O 4-51 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (Thiz-5) -Ph O 4-52 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Pyrr O 4-53 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Ph -2-Pyrr O 4-54 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Bz-2-Pyrr O 4-55 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Fur O 4-56 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-2-Fur O 4-57 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-Me-2-Thi
O 4-58 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-2-Thi O 4-59 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-Me-3-Thi O 4- 60 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-3-Thi O 4-61 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Me-3-Pyza O 4-62 iPr (CH ₂ ) ₂ H CH ₂ OEt 1- Ph-3-Pyza O 4- 63 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Imid O 4- 64 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-2-Imid O 4- 65 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Me-4-Imid O 4-66 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-4-Imid O 4-67 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Oxa O 4-68 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-Oxa O 4-69 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Oxa O 4-70 iPr ( CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Oxa O 4-71 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Oxa O 4-72 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Oxa O 4-73 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Me-2-Ph-5-Oxa O 4-74 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-Me- 2-Ph-4-Oxa O 4-75 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Thiz O 4- 76 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-Thiz O 4-77 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Thiz O 4-78 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Thiz O 4-79 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Me -5-Thiz O 4-80 iPr (CH ₂ ) ₂ H CH ₂ OE t 2-Ph-5-Thiz O 4-81 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Me-2-Ph-5-Thiz O 4-82 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-Me -2-Ph-4-Thiz O 4-83 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Me-4-Pyza O 4-84 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Ph-4-Pyza O 4-85 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Isox O 4-86 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4-Isox O 4-87 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Pyr O 4-88 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Pyr O 4-89 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Pyr O 4-90 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Me-5-Pyr O 4-91 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Et-5-Pyr O 4-92 iPr (CH ₂ ) ₂ H CH ₂ OEt 3 -Ph-5-Pyr O 4-93 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Me-5-Pyr O 4-94 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Et-5-Pyr O 4 -95 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Pyr O 4- 96 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-5-Pyr O 4- 97 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-EtO-5-Pyr O 4-98 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-5-Pyr O 4-99 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-MeS- 5-Pyr O 4-100 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-5-Pyr O 4-101 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS-5-Pyr O 4-102 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pyr O 4- 103 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-EtSO ₂ -5-Pyr O 4-104 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pyr O 4-105 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Bz-5-Pyr O 4-106 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-PhO-5-Pyr O 4-107 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-PhS -5-Pyr O 4-108 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pyr O 4-109 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Me-6-Pyr O 4- 110 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-6-Pyr O 4-111 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Me-6-Pyr O 4-112 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-6-Pyr O 4-113 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Me-4-Pym O 4-114 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-4 -Pym O 4-115 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-4-Pym O 4-116 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-EtO-4-Pym O 4-117 iPr ( CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-4-Pym O 4-118 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-4-Pym O 4-119 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-4-Pym O 4-120 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS-4-Pym O 4-121 iPr (CH ₂ ) ₂ H CH ₂ OEt 6-MeS-4-Pym O 4-122 iPr (CH ₂ ) ₂ H CH ₂ OEt 6-EtS-4-Pym O 4-123 iPr (CH ₂ ) ₂ H CH ₂ OEt 6-iPrS-4-Pym O 4-124 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-PhS-4-Pym O 4-1 25 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -4-Pym O 4-126 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-EtSO ₂ -4-Pym O 4-127 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -4-Pym O 4-128 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-PhSO ₂ -4-Pym O 4-129 iPr (CH ₂ ) ₂ H CH ₂ OEt 2 -Me-5-Pym O 4-130 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Ph-5-Pym O 4-131 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-MeO-5-Pym O 4 -132 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-EtO-5-Pym O 4-133 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-iPrO-5-Pym O 4-134 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-MeS-5-Pym O 4-135 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-EtS-5-Pym O 4-136 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-iPrS- 5-Pym O 4-137 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-PhS-5-Pym O 4-138 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pym O 4-139 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-EtSO ₂ -5-Pym O 4-140 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pym O 4-141 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pym O 4-142 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Ind O 4-143 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Ind O 4-144 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Ind O 4-145 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Me-3-Ind O 4-146 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Bimid O 4-147 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Boxa O 4-148 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-Bthiz O 4-149 iPr (CH ₂ ) ₂ H CH ₂ OEt 2- Quin O 4-150 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-Quin O 4-151 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-Quin O 4-152 iPr (CH ₂ ) ₂ H CH ₂ OEt 1 -iQuin O 4-153 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-iQuin O 4-154 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-iQuin O 4-155 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-MeO-Ph O 4-156 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-MeO-Ph O 4-157 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-EtO-Ph O 4-158 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-EtO-Ph O 4-159 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-iPrO-Ph O 4-160 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-iPrO-Ph O 4-161 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-MeS-Ph O 4-162 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-MeS-Ph O 4-163 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-EtS-Ph O 4-164 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-EtS-Ph O 4-165 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-iPrS-Ph O 4-166 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-iPrS-Ph O 4-167 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-MeSO ₂ -Ph O 4-168 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- MeSO ₂ -Ph O 4-169 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-EtSO ₂ -Ph O 4-170 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 4-171 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-iPrSO ₂ -Ph O 4-172 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 4- 173 iPr (CH ₂ ) ₂ H CH ₂ OEt 3- (1-Me-Imid-4) -Ph
O 4-174 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (1-Me-Imid-4) -Ph O 4-175 iPr (CH ₂ ) ₂ H CH ₂ OEt 1-Me-2-Ph-4 -Imid O 4-176 iPr (CH ₂ ) ₂ H CH ₂ OEt 1,4-di-Me-2-Ph-5-Imid O 4-177 iPr (CH ₂ ) ₂ H CH ₂ OEt 1,5-di -Me-2-Ph-4-Imid O 4-178 iPr (CH ₂ ) ₂ H CH ₂ OEt 3,4-MdO-Ph O 4-179 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (4- MeO-Ph) -Ph O 4-180 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (3,4-MdO-Ph) -Ph O 4-181 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- [ PhSO ₂ N (Me)]-Ph O 4-182 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ N (Me)]-Ph O 4-183 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (PhSO ₂ NH) -Ph O 4-184 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ NH] -Ph O 4-185 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ ] -Ph O 4-186 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ ] -Ph O 4-187 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ N (Me)]-Ph O 4-188 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ NH] -Ph O 4-189 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (4-Me-Ph) -Ph O 4-190 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (4-F- Ph) -Ph O 4-191 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (4-CF ₃ -Ph) -Ph O 4-192 iPr (CH ₂ ) ₂ H CH ₂ OEt 2- [4-Me -PhSO ₂ N (Me)]-5-Pyr O 4-193 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-HO-5-Pyr O 4-194 iPr (CH ₂ ) ₂ H CH ₂ OEt 2-BzO-5-Pyr O 4-195 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-[(Pyr-4) SO ₂ ] -Ph O 4-196 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (2,4-di-MeO-Ph) -Ph O 4- 197 iPr (CH ₂ ) ₂ H CH ₂ OEt 4- (2,5-di-MeO-Ph) -Ph O 4-198 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-HO-Ph O 4-199 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-HO-Ph O 4-200 iPr (CH ₂ ) ₂ H CH ₂ OEt 5-AcO-2-HO-3,4,6-tri-Me-Ph O 4- 201 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-HO-3,5-di-Me-Ph O 4-202 iPr (CH ₂ ) ₂ H CH ₂ OEt 3-AcO-Ph O 4-203 iPr (CH ₂ ) ₂ H CH ₂ OEt 4-AcO-Ph O _II .

[0135]

[Table 5] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 5- 1 H (CH ₂ ) ₂ H CH ₂ OMe Ph O 5- 2 H (CH ₂ ) ₂ H CH ₂ OMe 1-Np O 5- 3 H (CH ₂ ) ₂ H CH ₂ OMe 2-Np O 5- 4 H (CH ₂ ) ₂ H CH ₂ OMe 4-Me-Ph O 5- 5 H (CH ₂ ) ₂ H CH ₂ OMe 4-Et-Ph O 5- 6 H (CH ₂ ) ₂ H CH ₂ OMe 3-iPr-Ph O 5- 7 H ( CH ₂ ) ₂ H CH ₂ OMe 4-iPr-Ph O 5--8 H (CH ₂ ) ₂ H CH ₂ OMe 3-tBu-Ph O 5- 9 H (CH ₂ ) ₂ H CH ₂ OMe 4-tBu- Ph O 5- 10 H (CH ₂ ) ₂ H CH ₂ OMe 3-Cl-Ph O 5- 11 H (CH ₂ ) ₂ H CH ₂ OMe 4-Cl-Ph O 5- 12 H (CH ₂ ) ₂ H CH ₂ OMe 3-Br-Ph O 5- 13 H (CH ₂ ) ₂ H CH ₂ OMe 4-Br-Ph O 5- 14 H (CH ₂ ) ₂ H CH ₂ OMe 3-Ph-Ph O 5- 15 H (CH ₂ ) ₂ H CH ₂ OMe 4-Ph-Ph O 5- 16 H (CH ₂ ) ₂ H CH ₂ OMe 3-Bz-Ph O 5- 17 H (CH ₂ ) ₂ H CH ₂ OMe 4- Bz-Ph O 5- 18 H (CH ₂ ) ₂ H CH ₂ OMe 3-PhO-Ph O 5- 19 H (CH ₂ ) ₂ H CH ₂ OMe 4-PhO-Ph O 5- 20 H (CH ₂ ) ₂ H CH ₂ OMe 3-PhS-Ph O 5- 21 H (CH ₂ ) ₂ H CH ₂ OMe 4-PhS-Ph O 5--22 H ( CH ₂ ) ₂ H CH ₂ OMe 3-PhSO ₂ -Ph O 5- 23 H (CH ₂ ) ₂ H CH ₂ OMe 4-PhSO ₂ -Ph O 5- 24 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Imid-1) -Ph O 5- 25 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Imid-1) -Ph O 5-26 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Imid-4 ) -Ph O 5-27 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Imid-4) -Ph O 5-28 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Fur-2) -Ph O 5- 29 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Fur-2) -Ph O 5- 30 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Thi-2) -Ph O 5- 31 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Thi-2) -Ph O 5-32 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Thi-3) -Ph O 5-33 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Thi-3) -Ph O 5-34 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Pyr-2) -Ph O 5-35 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Pyr-2) -Ph O 5-36 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Pyr-3) -Ph O 5-37 H (CH ₂ ) ₂ H CH ₂ OMe 4- ( Pyr-3) -Ph O 5-38 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Pyr-4) -Ph O 5-39 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Pyr-4) -Ph O 5- 40 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Oxa-2) -Ph O 5- 41 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Oxa-2) -Ph O 5 -42 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Oxa-4) -Ph O 5-43 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Oxa-4) -Ph O 5-44 H (CH ₂ ) ₂ H CH ₂ OMe 3 -(Oxa-5) -Ph O 5-45 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Oxa-5) -Ph O 5-46 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Thiz- 2) -Ph O 5-47 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Thiz-2) -Ph O 5-48 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Thiz-4) -Ph O 5-49 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Thiz-4) -Ph O 5- 50 H (CH ₂ ) ₂ H CH ₂ OMe 3- (Thiz-5) -Ph O 5-51 H (CH ₂ ) ₂ H CH ₂ OMe 4- (Thiz-5) -Ph O 5-52 H (CH ₂ ) ₂ H CH ₂ OMe 1-Me-2-Pyrr O 5-53 H (CH ₂ ) ₂ H CH ₂ OMe 1-Ph-2-Pyrr O 5-54 H (CH ₂ ) ₂ H CH ₂ OMe 1-Bz-2-Pyrr O 5-55 H (CH ₂ ) ₂ H CH ₂ OMe 5-Me- 2-Fur O 5-56 H (CH ₂ ) ₂ H CH ₂ OMe 5-Ph-2-Fur O 5-57 H (CH ₂ ) ₂ H CH ₂ OMe 5-Me-2-Thi O 5-58 H (CH ₂ ) ₂ H CH ₂ OMe 5-Ph-2-Thi O 5-59 H (CH ₂ ) ₂ H CH ₂ OMe 5-Me-3-Thi O 5- 60 H (CH ₂ ) ₂ H CH ₂ OMe 5-Ph-3-Thi O 5-61 H (CH ₂ ) ₂ H CH ₂ OMe 1-Me-3-Pyza O 5-62 H (CH ₂ ) ₂ H CH ₂ OMe 1-Ph-3-Pyza O 5-63 H (CH ₂ ) ₂ H CH ₂ OMe 1-Me-2-Imid O 5-64 H (CH ₂ ) ₂ H CH ₂ OMe 1-Ph-2-Imid O 5-65 H (CH ₂ ) ₂ H C H ₂ OMe 1-Me-4-Imid O 5-66 H (CH ₂ ) ₂ H CH ₂ OMe 1-Ph-4-Imid O 5-67 H (CH ₂ ) ₂ H CH ₂ OMe 4-Oxa O 5 -68 H (CH ₂ ) ₂ H CH ₂ OMe 5-Oxa O 5-69 H (CH ₂ ) ₂ H CH ₂ OMe 2-Me-4-Oxa O 5-70 H (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-4-Oxa O 5-71 H (CH ₂ ) ₂ H CH ₂ OMe 2-Me-5-Oxa O 5-72 H (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-5-Oxa O 5- 73 H (CH ₂ ) ₂ H CH ₂ OMe 4-Me-2-Ph-5-Oxa O 5- 74 H (CH ₂ ) ₂ H CH ₂ OMe 5-Me-2-Ph-4-Oxa O 5-75 H (CH ₂ ) ₂ H CH ₂ OMe 4-Thiz O 5-76 H (CH ₂ ) ₂ H CH ₂ OMe 5-Thiz O 5-77 H (CH ₂ ) ₂ H CH ₂ OMe 2-Me -4-Thiz O 5-78 H (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-4-Thiz O 5-79 H (CH ₂ ) ₂ H CH ₂ OMe 2-Me-5-Thiz O 5-80 H (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-5-Thiz O 5-81 H (CH ₂ ) ₂ H CH ₂ OMe 4-Me-2-Ph-5-Thiz O 5-82 H (CH ₂ ) ₂ H CH ₂ OMe 5-Me-2-Ph-4-Thiz O 5-83 H (CH ₂ ) ₂ H CH ₂ OMe 1-Me-4-Pyza O 5-84 H (CH ₂ ) ₂ H CH ₂ OMe 1-Ph-4-Pyza O 5-85 H (CH ₂ ) ₂ H CH ₂ OMe 2-Me-4-Isox O 5-86 H (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-4- Isox O 5-87 H (CH ₂ ) ₂ H CH ₂ OMe 2-Pyr O 5-88 H (CH ₂ ) ₂ H CH ₂ OMe 3-Pyr O 5-89 H ( CH ₂ ) ₂ H CH ₂ OMe 4-Pyr O 5-90 H (CH ₂ ) ₂ H CH ₂ OMe 3-Me-5-Pyr O 5-91 H (CH ₂ ) ₂ H CH ₂ OMe 3-Et- 5-Pyr O 5-92 H (CH ₂ ) ₂ H CH ₂ OMe 3-Ph-5-Pyr O 5-93 H (CH ₂ ) ₂ H CH ₂ OMe 2-Me-5-Pyr O 5- 94 H (CH ₂ ) ₂ H CH ₂ OMe 2-Et-5-Pyr O 5-95 H (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-5-Pyr O 5-96 H (CH ₂ ) ₂ H CH ₂ OMe 2-MeO-5-Pyr O 5-97 H (CH ₂ ) ₂ H CH ₂ OMe 2-EtO-5-Pyr O 5-98 H (CH ₂ ) ₂ H CH ₂ OMe 2-iPrO-5-Pyr O 5- 99 H (CH ₂ ) ₂ H CH ₂ OMe 2-MeS-5-Pyr O 5-100 H (CH ₂ ) ₂ H CH ₂ OMe 2-EtS-5-Pyr O 5-101 H (CH ₂ ) ₂ H CH ₂ OMe 2-iPrS-5-Pyr O 5-102 H (CH ₂ ) ₂ H CH ₂ OMe 2-MeSO ₂ -5-Pyr O 5-103 H (CH ₂ ) ₂ H CH ₂ OMe 2 -EtSO ₂ -5-Pyr O 5-104 H (CH ₂ ) ₂ H CH ₂ OMe 2-iPrSO ₂ -5-Pyr O 5-105 H (CH ₂ ) ₂ H CH ₂ OMe 2-Bz-5-Pyr O 5-106 H (CH ₂ ) ₂ H CH ₂ OMe 2-PhO-5-Pyr O 5-107 H (CH ₂ ) ₂ H CH ₂ OMe 2-PhS-5-Pyr O 5-108 H (CH ₂ ) ₂ H CH ₂ OMe 2-PhSO ₂ -5-Pyr O 5-109 H (CH ₂ ) ₂ H CH ₂ OMe 3-Me-6-Pyr O 5-110 H (CH ₂ ) ₂ H CH ₂ OMe 3 -Ph-6-Pyr O 5-111 H (CH ₂ ) ₂ H CH ₂ OMe 2-Me-6-Pyr O 5-112 H (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-6-Pyr O 5-113 H (CH ₂ ) ₂ H CH ₂ OMe 2-Me-4-Pym O 5-114 H (CH ₂ ) ₂ H CH ₂ OMe 2-Ph- 4-Pym O 5-115 H (CH ₂ ) ₂ H CH ₂ OMe 2-MeO-4-Pym O 5-116 H (CH ₂ ) ₂ H CH ₂ OMe 2-EtO-4-Pym O 5-117 H (CH ₂ ) ₂ H CH ₂ OMe 2-iPrO-4-Pym O 5-118 H (CH ₂ ) ₂ H CH ₂ OMe 2-MeS-4-Pym O 5-119 H (CH ₂ ) ₂ H CH ₂ OMe 2-EtS-4-Pym O 5-120 H (CH ₂ ) ₂ H CH ₂ OMe 2-iPrS-4-Pym O 5-121 H (CH ₂ ) ₂ H CH ₂ OMe 6-MeS-4-Pym O 5-122 H (CH ₂ ) ₂ H CH ₂ OMe 6-EtS-4-Pym O 5-123 H (CH ₂ ) ₂ H CH ₂ OMe 6-iPrS-4-Pym O 5-124 H (CH ₂ ) ₂ H CH ₂ OMe 2-PhS-4-Pym O 5-125 H (CH ₂ ) ₂ H CH ₂ OMe 2-MeSO ₂ -4-Pym O 5-126 H (CH ₂ ) ₂ H CH ₂ OMe 2 -EtSO ₂ -4-Pym O 5-127 H (CH ₂ ) ₂ H CH ₂ OMe 2-iPrSO ₂ -4-Pym O 5-128 H (CH ₂ ) ₂ H CH ₂ OMe 2-PhSO ₂ -4- Pym O 5-129 H (CH ₂ ) ₂ H CH ₂ OMe 2-Me-5-Pym O 5-130 H (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-5-Pym O 5-131 H (CH ₂ ) ₂ H CH ₂ OMe 2-MeO-5-Pym O 5-132 H (CH ₂ ) ₂ H CH ₂ OMe 2-EtO-5-Pym O 5-133 H (CH ₂ ) ₂ H CH ₂ OMe 2 -iPrO-5-Pym O 5-134 H (CH ₂ ) ₂ H CH ₂ OMe 2-MeS-5-Pym O 5-135 H (CH ₂ ) ₂ H CH ₂ OMe 2-EtS-5-Pym O 5-136 H (CH ₂ ) ₂ H CH ₂ OMe 2-iPrS-5-Pym O 5-137 H (CH ₂ ) ₂ H CH ₂ OMe 2 -PhS-5-Pym O 5-138 H (CH ₂ ) ₂ H CH ₂ OMe 2-MeSO ₂ -5-Pym O 5-139 H (CH ₂ ) ₂ H CH ₂ OMe 2-EtSO ₂ -5-Pym O 5-140 H (CH ₂ ) ₂ H CH ₂ OMe 2-iPrSO ₂ -5-Pym O 5-141 H (CH ₂ ) ₂ H CH ₂ OMe 2-PhSO ₂ -5-Pym O 5-142 H ( CH ₂ ) ₂ H CH ₂ OMe 2-Ind O 5-143 H (CH ₂ ) ₂ H CH ₂ OMe 3-Ind O 5-144 H (CH ₂ ) ₂ H CH ₂ OMe 1-Me-2-Ind O 5-145 H (CH ₂ ) ₂ H CH ₂ OMe 1-Me-3-Ind O 5-146 H (CH ₂ ) ₂ H CH ₂ OMe 2-Bimid O 5-147 H (CH ₂ ) ₂ H CH ₂ OMe 2-Boxa O 5-148 H (CH ₂ ) ₂ H CH ₂ OMe 2-Bthiz O 5-149 H (CH ₂ ) ₂ H CH ₂ OMe 2-Quin O 5-150 H (CH ₂ ) ₂ H CH ₂ OMe 3-Quin O 5-151 H (CH ₂ ) ₂ H CH ₂ OMe 4-Quin O 5-152 H (CH ₂ ) ₂ H CH ₂ OMe 1-iQuin O 5-153 H (CH ₂ ) ₂ H CH ₂ OMe 3-iQuin O 5-154 H (CH ₂ ) ₂ H CH ₂ OMe 4-iQuin O 5-155 H (CH ₂ ) ₂ H CH ₂ OMe 3-MeO-Ph O 5-156 H (CH ₂ ) ₂ H CH ₂ OMe 4-MeO-Ph O 5-157 H (CH ₂ ) ₂ H CH ₂ OMe 3-EtO-Ph O 5-158 H (CH ₂ ) ₂ H CH ₂ OMe 4-EtO-Ph O 5-159 H (CH ₂ ) ₂ H CH ₂ OMe 3-iPrO-Ph O 5-160 H (CH ₂ ) ₂ H CH ₂ OMe 4-iPrO-Ph O 5-161 H (CH ₂ ) ₂ H CH ₂ OMe 3-MeS-Ph O 5-162 H (CH ₂ ) ₂ H CH ₂ OMe 4-MeS-Ph O 5-163 H (CH ₂ ) ₂ H CH ₂ OMe 3-EtS-Ph O 5-164 H (CH ₂ ) ₂ H CH ₂ OMe 4-EtS-Ph O 5-165 H (CH ₂ ) ₂ H CH ₂ OMe 3-iPrS-Ph O 5-166 H (CH ₂ ) ₂ H CH ₂ OMe 4-iPrS-Ph O 5-167 H (CH ₂ ) ₂ H CH ₂ OMe 3-MeSO ₂ -Ph O 5-168 H (CH ₂ ) ₂ H CH ₂ OMe 4-MeSO ₂ -Ph O 5-169 H (CH ₂ ) ₂ H CH ₂ OMe 3-EtSO ₂ -Ph O 5 -170 H (CH ₂ ) ₂ H CH ₂ OMe 4-EtSO ₂ -Ph O 5-171 H (CH ₂ ) ₂ H CH ₂ OMe 3-iPrSO ₂ -Ph O 5-172 H (CH ₂ ) ₂ H CH ₂ OMe 4-iPrSO ₂ -Ph O 5-173 H (CH ₂ ) ₂ H CH ₂ OMe 3- (1-Me-Imid-4) -Ph O 5-174 H (CH ₂ ) ₂ H CH ₂ OMe 4 -(1-Me-Imid-4) -Ph O 5-175 H (CH ₂ ) ₂ H CH ₂ OMe 1-Me-2-Ph-4-Imid O 5-176 H (CH ₂ ) ₂ H CH ₂ OMe 1,4-di-Me-2-Ph-5-Imid O 5-177 H (CH ₂ ) ₂ H CH ₂ OMe 1,5-di-Me-2-Ph-4-Imid O 5-178 H (CH ₂ ) ₂ H CH ₂ OMe 3,4-MdO-Ph O 5-179 H (CH ₂ ) ₂ H CH ₂ OMe 4- (4-MeO-Ph) -Ph O 5-180 H (CH ₂ ) ₂ H CH ₂ OMe 4- (3,4-MdO-Ph) -Ph O 5-181 H (CH ₂ ) ₂ H CH ₂ OMe 4- [PhSO ₂ N (Me)]- Ph O 5-182 H (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-3) SO ₂ N (Me)]-Ph O 5-183 H (CH ₂ ) ₂ H CH ₂ OMe 4- (PhSO ₂ NH) -Ph O 5-184 H (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-3) SO ₂ NH] -Ph O 5-185 H (CH ₂ ) ₂ H CH ₂ OMe 4- [ (Pyr-2) SO ₂ ] -Ph O 5-186 H (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-3) SO ₂ ] -Ph O 5-187 H (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-2) SO ₂ N (Me)]-Ph O 5-188 H (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-2) SO ₂ NH] -Ph O 5-189 H (CH ₂ ) ₂ H CH ₂ OMe 4- (4-Me-Ph) -Ph O 5-190 H (CH ₂ ) ₂ H CH ₂ OMe 4- (4-F-Ph) -Ph O 5-191 H (CH ₂ ) ₂ H CH ₂ OMe 4- (4-CF ₃ -Ph) -Ph O 5-192 H (CH ₂ ) ₂ H CH ₂ OMe 2- [4-Me-PhSO ₂ N (Me)] -5-Pyr O 5-193 H (CH ₂ ) ₂ H CH ₂ OMe 2-HO-5-Pyr O 5-194 H (CH ₂ ) ₂ H CH ₂ OMe 2-BzO-5-Pyr O 5-195 H (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-4) SO ₂ ] -Ph O 5-196 H (CH ₂ ) ₂ H CH ₂ OMe 4- (2,4-di-MeO-Ph) -Ph O 5-197 H (CH ₂ ) ₂ H CH ₂ OMe 4- (2,5-di-MeO-Ph) -Ph O 5-198 H (CH ₂ ) ₂ H CH ₂ OMe 3-HO-Ph O 5-199 H (CH ₂ ) ₂ H CH ₂ OMe 4-HO-Ph O 5-200 H (CH ₂ ) ₂ H CH ₂ OMe 5-AcO-2-HO-3,4,6-tri-Me -Ph O 5-201 H (CH ₂ ) ₂ H CH ₂ OMe 4-HO-3,5-di-Me-Ph O 5-2 02 H (CH ₂ ) ₂ H CH ₂ OMe 3-AcO-Ph O 5-203 H (CH ₂ ) ₂ H CH ₂ OMe 4-AcO-Ph O 203 ────────────────────.

[0136]

[Table 6] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 6-1 Me (CH ₂ ) ₂ H CH ₂ OMe Ph O 6- 2 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Np O 6- 3 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Np O 6- 4 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Me-Ph O 6- 5 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Et-Ph O 6- 6 Me (CH ₂ ) ₂ H CH ₂ OMe 3-iPr-Ph O 6- 7 Me ( CH ₂ ) ₂ H CH ₂ OMe 4-iPr-Ph O 6- 8 Me (CH ₂ ) ₂ H CH ₂ OMe 3-tBu-Ph O 6- 9 Me (CH ₂ ) ₂ H CH ₂ OMe 4-tBu- Ph O 6- 10 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Cl-Ph O 6- 11 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Cl-Ph O 6- 12 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Br-Ph O 6-13 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Br-Ph O 6-14 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Ph-Ph O 6-15 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Ph-Ph O 6-16 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Bz-Ph O 6-17 Me (CH ₂ ) ₂ H CH ₂ OMe 4- Bz-Ph O 6-18 Me (CH ₂ ) ₂ H CH ₂ OMe 3-PhO-Ph O 6-19 Me (CH ₂ ) ₂ H CH ₂ OMe 4-PhO-Ph O 6-20 Me (CH ₂ ) ₂ H CH ₂ OMe 3-PhS-Ph O 6- 21 Me (CH ₂ ) ₂ H CH ₂ OMe 4- PhS-Ph O 6- 22 Me (CH ₂ ) ₂ H CH ₂ OMe 3-PhSO ₂ -Ph O 6- 23 Me (CH ₂ ) ₂ H CH ₂ OMe 4-PhSO ₂ -Ph O 6- 24 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Imid-1) -Ph O 6-25 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Imid-1) -Ph O 6- 26 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Imid-4) -Ph O 6- 27 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Imid-4) -Ph O 6- 28 Me (CH ₂ ) ₂ H CH ₂ OMe 3 -(Fur-2) -Ph O 6- 29 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Fur-2) -Ph O 6-30 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Thi- 2) -Ph O 6- 31 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Thi-2) -Ph O 6- 32 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Thi-3) -Ph O 6- 33 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Thi-3) -Ph O 6- 34 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Pyr-2) -Ph O 6- 35 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Pyr-2) -Ph O 6- 36 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Pyr-3) -Ph O 6- 37 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Pyr-3) -Ph O 6- 38 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Pyr-4) -Ph O 6- 39 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Pyr-4) -Ph O 6-40 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Oxa-2) -Ph O 6- 41 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Oxa-2) -Ph O 6- 42 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Oxa-4) -Ph O 6- 43 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Oxa-4) -Ph O 6- 44 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Oxa-5) -Ph O 6- 45 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Oxa-5 ) -Ph O 6- 46 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Thiz-2) -Ph O 6- 47 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Thiz-2) -Ph O 6- 48 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Thiz-4) -Ph O 6- 49 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Thiz-4) -Ph O 6-50 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (Thiz-5) -Ph O 6-51 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Thiz-5) -Ph O 6-52 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Me-2-Pyrr O 6- 53 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Ph-2-Pyrr O 6- 54 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Bz -2-Pyrr O 6- 55 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Me-2-Fur O 6- 56 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Ph-2-Fur O 6- 57 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Me-2-Thi O 6- 58 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Ph-2-Thi O 6- 59 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Me-3-Thi O 6-60 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Ph-3-Thi O 6- 61 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Me-3- Pyza O 6- 62 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Ph-3-Pyza O 6- 63 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Me-2-Imid O 6 -64 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Ph-2-Imid O 6-65 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Me-4-Imid O 6-66 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Ph-4-Imid O 6- 67 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Oxa O 6- 68 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Oxa O 6- 69 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Me-4-Oxa O 6- 70 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-4-Oxa O 6- 71 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Me-5-Oxa O 6- 72 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-5-Oxa O 6- 73 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Me-2-Ph -5-Oxa O 6- 74 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Me-2-Ph-4-Oxa O 6- 75 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Thiz O 6- 76 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Thiz O 6- 77 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Me-4-Thiz O 6- 78 Me (CH ₂ ) ₂ H CH ₂ OMe 2- Ph-4-Thiz O 6- 79 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Me-5-Thiz O 6- 80 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-5-Thiz O 6- 81 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Me-2-Ph-5-Thiz O 6- 82 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Me-2-Ph-4-Thiz O 6- 83 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Me-4-Pyza O 6- 84 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Ph-4-Pyza O 6- 85 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Me-4-Isox O 6- 86 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-4-Isox O 6- 87 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Pyr O 6- 88 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Pyr O 6- 89 Me (CH ₂ ) ₂ H CH ₂ OMe 4- Pyr O 6- 90 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Me-5-Pyr O 6- 91 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Et-5-Pyr O 6- 92 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Ph-5-Pyr O 6- 93 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Me-5-Pyr O 6- 94 Me (CH ₂ ) ₂ H CH ₂ OMe 2 -Et-5-Pyr O 6- 95 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-5-Pyr O 6- 96 Me (CH ₂ ) ₂ H CH ₂ OMe 2-MeO-5-Pyr O 6 -97 Me (CH ₂ ) ₂ H CH ₂ OMe 2-EtO-5-Pyr O 6- 98 Me (CH ₂ ) ₂ H CH ₂ OMe 2-iPrO-5-Pyr O 6- 99 Me (CH ₂ ) ₂ H CH ₂ OMe 2-MeS-5-Pyr O 6-100 Me (CH ₂ ) ₂ H CH ₂ OMe 2-EtS-5-Pyr O 6-101 Me (CH ₂ ) ₂ H CH ₂ OMe 2-iPrS- 5-Pyr O 6-102 Me (CH ₂ ) ₂ H CH ₂ OMe 2-MeSO ₂ -5-Pyr O 6-103 Me (CH ₂ ) ₂ H CH ₂ OMe 2-EtSO ₂ -5-Pyr O 6- 104 Me (CH ₂ ) ₂ H CH ₂ OMe 2-iPrSO ₂ -5-Pyr O 6-105 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Bz-5-Pyr O 6-106 Me (CH ₂ ) ₂ H CH ₂ OMe 2-PhO-5-Pyr O 6-107 Me (CH ₂ ) ₂ H CH ₂ OMe 2-PhS-5-Pyr O 6-108 Me (CH ₂ ) ₂ H CH ₂ OMe 2-PhSO ₂ -5-Pyr O 6-109 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Me- 6-Pyr O 6-110 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Ph-6-Pyr O 6-111 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Me-6-Pyr O 6-112 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-6-Pyr O 6-113 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Me-4-Pym O 6-114 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-4-Pym O 6-115 Me (CH ₂ ) ₂ H CH ₂ OMe 2-MeO-4-Pym O 6-116 Me (CH ₂ ) ₂ H CH ₂ OMe 2-EtO-4-Pym O 6-117 Me (CH ₂ ) ₂ H CH ₂ OMe 2-iPrO-4-Pym O 6-118 Me (CH ₂ ) ₂ H CH ₂ OMe 2-MeS-4-Pym O 6-119 Me (CH ₂ ) ₂ H CH ₂ OMe 2-EtS-4-Pym O 6-120 Me (CH ₂ ) ₂ H CH ₂ OMe 2-iPrS-4-Pym O 6-121 Me (CH ₂ ) ₂ H CH ₂ OMe 6- MeS-4-Pym O 6-122 Me (CH ₂ ) ₂ H CH ₂ OMe 6-EtS-4-Pym O 6-123 Me (CH ₂ ) ₂ H CH ₂ OMe 6-iPrS-4-Pym O 6- 124 Me (CH ₂ ) ₂ H CH ₂ OMe 2-PhS-4-Pym O 6-125 Me (CH ₂ ) ₂ H CH ₂ OMe 2-MeSO ₂ -4-Pym O 6-126 Me (CH ₂ ) ₂ H CH ₂ OMe 2-EtSO ₂ -4-Pym O 6-127 Me (CH ₂ ) ₂ H CH ₂ OMe 2-iPrSO ₂ -4-Pym O 6-128 Me (CH ₂ ) ₂ H CH ₂ OMe 2- PhSO ₂ -4-Pym O 6-129 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Me-5-Pym O 6-130 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Ph-5-Pym O 6 -131 Me (CH ₂ ) ₂ H CH ₂ OMe 2-MeO-5-Pym O 6 -132 Me (C H ₂ ) ₂ H CH ₂ OMe 2-EtO-5-Pym O 6-133 Me (CH ₂ ) ₂ H CH ₂ OMe 2-iPrO-5-Pym O 6-134 Me (CH ₂ ) ₂ H CH ₂ OMe 2-MeS-5-Pym O 6-135 Me (CH ₂ ) ₂ H CH ₂ OMe 2-EtS-5-Pym O 6-136 Me (CH ₂ ) ₂ H CH ₂ OMe 2-iPrS-5-Pym O 6-137 Me (CH ₂ ) ₂ H CH ₂ OMe 2-PhS-5-Pym O 6-138 Me (CH ₂ ) ₂ H CH ₂ OMe 2-MeSO ₂ -5-Pym O 6-139 Me (CH ₂ ) ₂ H CH ₂ OMe 2-EtSO ₂ -5-Pym O 6-140 Me (CH ₂ ) ₂ H CH ₂ OMe 2-iPrSO ₂ -5-Pym O 6-141 Me (CH ₂ ) ₂ H CH ₂ OMe 2-PhSO ₂ -5-Pym O 6-142 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Ind O 6-143 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Ind O 6-144 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Me-2-Ind O 6-145 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Me-3-Ind O 6-146 Me (CH ₂ ) ₂ H CH ₂ OMe 2- Bimid O 6-147 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Boxa O 6-148 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Bthiz O 6-149 Me (CH ₂ ) ₂ H CH ₂ OMe 2 -Quin O 6-150 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Quin O 6-151 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Quin O 6-152 Me (CH ₂ ) ₂ H CH ₂ OMe 1-iQuin O 6-153 Me (CH ₂ ) ₂ H CH ₂ OMe 3-iQuin O 6-154 Me (CH ₂ ) ₂ H CH ₂ OMe 4-iQuin O 6-155 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Me O-Ph O 6-156 Me (CH ₂ ) ₂ H CH ₂ OMe 4-MeO-Ph O 6-157 Me (CH ₂ ) ₂ H CH ₂ OMe 3-EtO-Ph O 6-158 Me (CH ₂ ) ₂ H CH ₂ OMe 4-EtO-Ph O 6-159 Me (CH ₂ ) ₂ H CH ₂ OMe 3-iPrO-Ph O 6-160 Me (CH ₂ ) ₂ H CH ₂ OMe 4-iPrO-Ph O 6 -161 Me (CH ₂ ) ₂ H CH ₂ OMe 3-MeS-Ph O 6 -162 Me (CH ₂ ) ₂ H CH ₂ OMe 4-MeS-Ph O 6-163 Me (CH ₂ ) ₂ H CH ₂ OMe 3-EtS-Ph O 6-164 Me (CH ₂ ) ₂ H CH ₂ OMe 4-EtS-Ph O 6-165 Me (CH ₂ ) ₂ H CH ₂ OMe 3-iPrS-Ph O 6-166 Me (CH ₂ ) ₂ H CH ₂ OMe 4-iPrS-Ph O 6-167 Me (CH ₂ ) ₂ H CH ₂ OMe 3-MeSO ₂ -Ph O 6-168 Me (CH ₂ ) ₂ H CH ₂ OMe 4-MeSO ₂ -Ph O 6-169 Me (CH ₂ ) ₂ H CH ₂ OMe 3-EtSO ₂ -Ph O 6-170 Me (CH ₂ ) ₂ H CH ₂ OMe 4-EtSO ₂ -Ph O 6-171 Me (CH ₂ ) ₂ H CH ₂ OMe 3-iPrSO ₂ -Ph O 6-172 Me (CH ₂ ) ₂ H CH ₂ OMe 4-iPrSO ₂ -Ph O 6-173 Me (CH ₂ ) ₂ H CH ₂ OMe 3- (1 -Me-Imid-4) -Ph O 6-174 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (1-Me-Imid-4) -Ph O 6-175 Me (CH ₂ ) ₂ H CH ₂ OMe 1-Me-2-Ph-4-Imid O 6-176 Me (CH ₂ ) ₂ H CH ₂ OMe 1,4-di-Me-2-Ph-5-Imid O 6-177 Me (CH ₂ ) ₂ H CH ₂ OMe 1,5-di-Me-2-Ph-4-Imid O 6-178 M e (CH ₂ ) ₂ H CH ₂ OMe 3,4-MdO-Ph O 6-179 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (4-MeO-Ph) -Ph O 6-180 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (3,4-MdO-Ph) -Ph O 6-181 Me (CH ₂ ) ₂ H CH ₂ OMe 4- [PhSO ₂ N (Me)]-Ph O 6-182 Me (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-3) SO ₂ N (Me)]-Ph O 6-183 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (PhSO ₂ NH) -Ph O 6-184 Me (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-3) SO ₂ NH] -Ph O 6-185 Me (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-2) SO ₂ ] -Ph O 6-186 Me (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-3) SO ₂ ] -Ph O 6-187 Me (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr -2) SO ₂ N (Me)]-Ph O 6-188 Me (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-2) SO ₂ NH] -Ph O 6-189 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (4-Me-Ph) -Ph O 6-190 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (4-F-Ph) -Ph O 6-191 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (4-CF ₃ -Ph) -Ph O 6 -192 Me (CH ₂ ) ₂ H CH ₂ OMe 2- [4-Me-PhSO ₂ N (Me)]-5-Pyr O 6 -193 Me (CH ₂ ) ₂ H CH ₂ OMe 2-HO-5-Pyr O 6 -194 Me (CH ₂ ) ₂ H CH ₂ OMe 2-BzO-5-Pyr O 6-195 Me (CH ₂ ) ₂ H CH ₂ OMe 4-[(Pyr-4) SO ₂ ] -Ph O 6-196 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (2,4-di-MeO-Ph) -Ph O 6-197 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (2,5-di-MeO- Ph) -Ph O 6-198 Me (CH ₂ ) ₂ H CH ₂ OMe 3-HO-Ph O 6-199 Me (CH ₂ ) ₂ H CH ₂ OMe 4-HO-Ph O 6-200 Me (CH ₂ ) ₂ H CH ₂ OMe 5-AcO-2-HO-3,4,6-tri-Me-Ph O 6-201 Me (CH ₂ ) ₂ H CH ₂ OMe 4-HO-3,5-di-Me -Ph O 6-202 Me (CH ₂ ) ₂ H CH ₂ OMe 3-AcO-Ph O 6-203 Me (CH ₂ ) ₂ H CH ₂ OMe 4-AcO-Ph O ───────── ─────────────────────────.

[0137]

[Table 7] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 7-1 H (CH ₂ ) ₃ H CH ₂ OEt Ph O 7- 2 H (CH ₂ ) ₃ H CH ₂ OEt 1-Np O 7- 3 H (CH ₂ ) ₃ H CH ₂ OEt 2-Np O 7- 4 H (CH ₂ ) ₃ H CH ₂ OEt 4-Me-Ph O 7-5 H (CH ₂ ) ₃ H CH ₂ OEt 4-Et-Ph O 7-6 H (CH ₂ ) ₃ H CH ₂ OEt 3-iPr-Ph O 7-7 H ( CH ₂ ) ₃ H CH ₂ OEt 4-iPr-Ph O 7- 8 H (CH ₂ ) ₃ H CH ₂ OEt 3-tBu-Ph O 7- 9 H (CH ₂ ) ₃ H CH ₂ OEt 4-tBu- Ph O 7-10 H (CH ₂ ) ₃ H CH ₂ OEt 3-Cl-Ph O 7-11 H (CH ₂ ) ₃ H CH ₂ OEt 4-Cl-Ph O 7-12 H (CH ₂ ) ₃ H CH ₂ OEt 3-Br-Ph O 7-13 H (CH ₂ ) ₃ H CH ₂ OEt 4-Br-Ph O 7- 14 H (CH ₂ ) ₃ H CH ₂ OEt 3-Ph-Ph O 7-15 H (CH ₂ ) ₃ H CH ₂ OEt 4-Ph-Ph O 7-16 H (CH ₂ ) ₃ H CH ₂ OEt 3-Bz-Ph O 7-17 H (CH ₂ ) ₃ H CH ₂ OEt 4- Bz-Ph O 7-18 H (CH ₂ ) ₃ H CH ₂ OEt 3-PhO-Ph O 7-19 H (CH ₂ ) ₃ H CH ₂ OEt 4-PhO-Ph O 7-20 H (CH ₂ ) ₃ H CH ₂ OEt 3-PhS-Ph O 7- 21 H (CH ₂ ) ₃ H CH ₂ OEt 4-PhS-Ph O 7-22 H ( CH ₂ ) ₃ H CH ₂ OEt 3-PhSO ₂ -Ph O 7-23 H (CH ₂ ) ₃ H CH ₂ OEt 4-PhSO ₂ -Ph O 7- 24 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Imid-1) -Ph O 7-25 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Imid-1) -Ph O 7- 26 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Imid-4 ) -Ph O 7- 27 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Imid-4) -Ph O 7- 28 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Fur-2) -Ph O 7- 29 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Fur-2) -Ph O 7-30 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Thi-2) -Ph O 7- 31 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Thi-2) -Ph O 7- 32 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Thi-3) -Ph O 7- 33 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Thi-3) -Ph O 7- 34 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Pyr-2) -Ph O 7- 35 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Pyr-2) -Ph O 7- 36 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Pyr-3) -Ph O 7- 37 H (CH ₂ ) ₃ H CH ₂ OEt 4- ( Pyr-3) -Ph O 7- 38 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Pyr-4) -Ph O 7- 39 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Pyr-4) -Ph O 7-40 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Oxa-2) -Ph O 7-41 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Oxa-2) -Ph O 7 -42 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Oxa-4) -Ph O 7- 43 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Oxa-4) -Ph O 7- 44 H (CH ₂ ) ₃ H CH ₂ OEt 3 -(Oxa-5) -Ph O 7- 45 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Oxa-5) -Ph O 7- 46 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Thiz- 2) -Ph O 7- 47 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Thiz-2) -Ph O 7- 48 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Thiz-4) -Ph O 7- 49 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Thiz-4) -Ph O 7-50 H (CH ₂ ) ₃ H CH ₂ OEt 3- (Thiz-5) -Ph O 7- 51 H (CH ₂ ) ₃ H CH ₂ OEt 4- (Thiz-5) -Ph O 7- 52 H (CH ₂ ) ₃ H CH ₂ OEt 1-Me-2-Pyrr O 7- 53 H (CH ₂ ) ₃ H CH ₂ OEt 1-Ph-2-Pyrr O 7- 54 H (CH ₂ ) ₃ H CH ₂ OEt 1-Bz-2-Pyrr O 7- 55 H (CH ₂ ) ₃ H CH ₂ OEt 5-Me- 2-Fur O 7- 56 H (CH ₂ ) ₃ H CH ₂ OEt 5-Ph-2-Fur O 7- 57 H (CH ₂ ) ₃ H CH ₂ OEt 5-Me-2-Thi O 7- 58 H (CH ₂ ) ₃ H CH ₂ OEt 5-Ph-2-Thi O 7- 59 H (CH ₂ ) ₃ H CH ₂ OEt 5-Me-3-Thi O 7-60 H (CH ₂ ) ₃ H CH ₂ OEt 5-Ph-3-Thi O 7- 61 H (CH ₂ ) ₃ H CH ₂ OEt 1-Me-3-Pyza O 7- 62 H (CH ₂ ) ₃ H CH ₂ OEt 1-Ph-3-Pyza O 7- 63 H (CH ₂ ) ₃ H CH ₂ OEt 1-Me-2-Imid O 7- 64 H (CH ₂ ) ₃ H CH ₂ OEt 1-Ph-2-Imid O 7- 65 H (CH ₂ ) ₃ H C H ₂ OEt 1-Me-4-Imid O 7- 66 H (CH ₂ ) ₃ H CH ₂ OEt 1-Ph-4-Imid O 7- 67 H (CH ₂ ) ₃ H CH ₂ OEt 4-Oxa O 7 -68 H (CH ₂ ) ₃ H CH ₂ OEt 5-Oxa O 7- 69 H (CH ₂ ) ₃ H CH ₂ OEt 2-Me-4-Oxa O 7- 70 H (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-4-Oxa O 7- 71 H (CH ₂ ) ₃ H CH ₂ OEt 2-Me-5-Oxa O 7- 72 H (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-5-Oxa O 7- 73 H (CH ₂ ) ₃ H CH ₂ OEt 4-Me-2-Ph-5-Oxa O 7- 74 H (CH ₂ ) ₃ H CH ₂ OEt 5-Me-2-Ph-4-Oxa O 7- 75 H (CH ₂ ) ₃ H CH ₂ OEt 4-Thiz O 7- 76 H (CH ₂ ) ₃ H CH ₂ OEt 5-Thiz O 7- 77 H (CH ₂ ) ₃ H CH ₂ OEt 2-Me -4-Thiz O 7- 78 H (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-4-Thiz O 7- 79 H (CH ₂ ) ₃ H CH ₂ OEt 2-Me-5-Thiz O 7- 80 H (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-5-Thiz O 7- 81 H (CH ₂ ) ₃ H CH ₂ OEt 4-Me-2-Ph-5-Thiz O 7- 82 H (CH ₂ ) ₃ H CH ₂ OEt 5-Me-2-Ph-4-Thiz O 7- 83 H (CH ₂ ) ₃ H CH ₂ OEt 1-Me-4-Pyza O 7- 84 H (CH ₂ ) ₃ H CH ₂ OEt 1-Ph-4-Pyza O 7- 85 H (CH ₂ ) ₃ H CH ₂ OEt 2-Me-4-Isox O 7- 86 H (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-4- Isox O 7- 87 H (CH ₂ ) ₃ H CH ₂ OEt 2-Pyr O 7- 88 H (CH ₂ ) ₃ H CH ₂ OEt 3-Pyr O 7- 89 H ( CH ₂ ) ₃ H CH ₂ OEt 4-Pyr O 7- 90 H (CH ₂ ) ₃ H CH ₂ OEt 3-Me-5-Pyr O 7- 91 H (CH ₂ ) ₃ H CH ₂ OEt 3-Et- 5-Pyr O 7- 92 H (CH ₂ ) ₃ H CH ₂ OEt 3-Ph-5-Pyr O 7- 93 H (CH ₂ ) ₃ H CH ₂ OEt 2-Me-5-Pyr O 7- 94 H (CH ₂ ) ₃ H CH ₂ OEt 2-Et-5-Pyr O 7- 95 H (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-5-Pyr O 7- 96 H (CH ₂ ) ₃ H CH ₂ OEt 2-MeO-5-Pyr O 7- 97 H (CH ₂ ) ₃ H CH ₂ OEt 2-EtO-5-Pyr O 7- 98 H (CH ₂ ) ₃ H CH ₂ OEt 2-iPrO-5-Pyr O 7- 99 H (CH ₂ ) ₃ H CH ₂ OEt 2-MeS-5-Pyr O 7-100 H (CH ₂ ) ₃ H CH ₂ OEt 2-EtS-5-Pyr O 7-101 H (CH ₂ ) ₃ H CH ₂ OEt 2-iPrS-5-Pyr O 7-102 H (CH ₂ ) ₃ H CH ₂ OEt 2-MeSO ₂ -5-Pyr O 7-103 H (CH ₂ ) ₃ H CH ₂ OEt 2 -EtSO ₂ -5-Pyr O 7-104 H (CH ₂ ) ₃ H CH ₂ OEt 2-iPrSO ₂ -5-Pyr O 7-105 H (CH ₂ ) ₃ H CH ₂ OEt 2-Bz-5-Pyr O 7-106 H (CH ₂ ) ₃ H CH ₂ OEt 2-PhO-5-Pyr O 7-107 H (CH ₂ ) ₃ H CH ₂ OEt 2-PhS-5-Pyr O 7-108 H (CH ₂ ) ₃ H CH ₂ OEt 2-PhSO ₂ -5-Pyr O 7-109 H (CH ₂ ) ₃ H CH ₂ OEt 3-Me-6-Pyr O 7-110 H (CH ₂ ) ₃ H CH ₂ OEt 3 -Ph-6-Pyr O 7-111 H (CH ₂ ) ₃ H CH ₂ OEt 2-Me-6-Pyr O 7-112 H (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-6-Pyr O 7-113 H (CH ₂ ) ₃ H CH ₂ OEt 2-Me-4-Pym O 7-114 H (CH ₂ ) ₃ H CH ₂ OEt 2-Ph- 4-Pym O 7-115 H (CH ₂ ) ₃ H CH ₂ OEt 2-MeO-4-Pym O 7-116 H (CH ₂ ) ₃ H CH ₂ OEt 2-EtO-4-Pym O 7-117 H (CH ₂ ) ₃ H CH ₂ OEt 2-iPrO-4-Pym O 7-118 H (CH ₂ ) ₃ H CH ₂ OEt 2-MeS-4-Pym O 7-119 H (CH ₂ ) ₃ H CH ₂ OEt 2-EtS-4-Pym O 7-120 H (CH ₂ ) ₃ H CH ₂ OEt 2-iPrS-4-Pym O 7-121 H (CH ₂ ) ₃ H CH ₂ OEt 6-MeS-4-Pym O 7-122 H (CH ₂ ) ₃ H CH ₂ OEt 6-EtS-4-Pym O 7-123 H (CH ₂ ) ₃ H CH ₂ OEt 6-iPrS-4-Pym O 7-124 H (CH ₂ ) ₃ H CH ₂ OEt 2-PhS-4-Pym O 7-125 H (CH ₂ ) ₃ H CH ₂ OEt 2-MeSO ₂ -4-Pym O 7-126 H (CH ₂ ) ₃ H CH ₂ OEt 2 -EtSO ₂ -4-Pym O 7-127 H (CH ₂ ) ₃ H CH ₂ OEt 2-iPrSO ₂ -4-Pym O 7-128 H (CH ₂ ) ₃ H CH ₂ OEt 2-PhSO ₂ -4- Pym O 7-129 H (CH ₂ ) ₃ H CH ₂ OEt 2-Me-5-Pym O 7-130 H (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-5-Pym O 7-131 H (CH ₂ ) ₃ H CH ₂ OEt 2-MeO-5-Pym O 7-132 H (CH ₂ ) ₃ H CH ₂ OEt 2-EtO-5-Pym O 7-133 H (CH ₂ ) ₃ H CH ₂ OEt 2 -iPrO-5-Pym O 7-134 H (CH ₂ ) ₃ H CH ₂ OEt 2-MeS-5-Pym O 7-135 H (CH ₂ ) ₃ H CH ₂ OEt 2-EtS-5-Pym O 7-136 H (CH ₂ ) ₃ H CH ₂ OEt 2-iPrS-5-Pym O 7-137 H (CH ₂ ) ₃ H CH ₂ OEt 2 -PhS-5-Pym O 7-138 H (CH ₂ ) ₃ H CH ₂ OEt 2-MeSO ₂ -5-Pym O 7-139 H (CH ₂ ) ₃ H CH ₂ OEt 2-EtSO ₂ -5-Pym O 7-140 H (CH ₂ ) ₃ H CH ₂ OEt 2-iPrSO ₂ -5-Pym O 7-141 H (CH ₂ ) ₃ H CH ₂ OEt 2-PhSO ₂ -5-Pym O 7-142 H ( CH ₂ ) ₃ H CH ₂ OEt 2-Ind O 7-143 H (CH ₂ ) ₃ H CH ₂ OEt 3-Ind O 7-144 H (CH ₂ ) ₃ H CH ₂ OEt 1-Me-2-Ind O 7-145 H (CH ₂ ) ₃ H CH ₂ OEt 1-Me-3-Ind O 7-146 H (CH ₂ ) ₃ H CH ₂ OEt 2-Bimid O 7-147 H (CH ₂ ) ₃ H CH ₂ OEt 2-Boxa O 7-148 H (CH ₂ ) ₃ H CH ₂ OEt 2-Bthiz O 7-149 H (CH ₂ ) ₃ H CH ₂ OEt 2-Quin
O 7-150 H (CH ₂ ) ₃ H CH ₂ OEt 3-Quin O 7-151 H (CH ₂ ) ₃ H CH ₂ OEt 4-Quin O 7-152 H (CH ₂ ) ₃ H CH ₂ OEt 1- iQuin O 7-153 H (CH ₂ ) ₃ H CH ₂ OEt 3-iQuin O 7-154 H (CH ₂ ) ₃ H CH ₂ OEt 4-iQuin O 7-155 H (CH ₂ ) ₃ H CH ₂ OEt 3 -MeO-Ph O 7-156 H (CH ₂ ) ₃ H CH ₂ OEt 4-MeO-Ph O 7-157 H (CH ₂ ) ₃ H CH ₂ OEt 3-EtO-Ph O 7-158 H (CH ₂ ) ₃ H CH ₂ OEt 4-EtO-Ph O 7-159 H (CH ₂ ) ₃ H CH ₂ OEt 3-iPrO-Ph O 7-160 H (CH ₂ ) ₃ H CH ₂ OEt 4-iPrO-Ph O 7-161 H (CH ₂ ) ₃ H CH ₂ OEt 3-MeS-Ph O 7-162 H (CH ₂ ) ₃ H CH ₂ OEt 4-MeS-Ph O 7-163 H (CH ₂ ) ₃ H CH ₂ OEt 3-EtS-Ph O 7-164 H (CH ₂ ) ₃ H CH ₂ OEt 4-EtS-Ph O 7-165 H (CH ₂ ) ₃ H CH ₂ OEt 3-iPrS-Ph O 7-166 H ( CH ₂ ) ₃ H CH ₂ OEt 4-iPrS-Ph O 7-167 H (CH ₂ ) ₃ H CH ₂ OEt 3-MeSO ₂ -Ph O 7-168 H (CH ₂ ) ₃ H CH ₂ OEt 4-MeSO ₂ -Ph O 7-169 H (CH ₂ ) ₃ H CH ₂ OEt 3-EtSO ₂ -Ph O 7-170 H (CH ₂ ) ₃ H CH ₂ OEt 4-EtSO ₂ -Ph O 7-171 H (CH ₂ ) ₃ H CH ₂ OEt 3-iPrSO ₂ -Ph O 7-172 H (CH ₂ ) ₃ H CH ₂ OEt 4-iPrSO ₂ -Ph O 7-173 H (CH ₂ ) ₃ H CH ₂ OEt 3- ( 1-Me-Imid-4) -Ph O 7-174 H (CH ₂ ) ₃ H CH ₂ OEt 4- (1-Me-Imid-4) -Ph O 7-175 H (CH ₂ ) ₃ H CH ₂ OEt 1-Me-2-Ph-4-Imid O 7 -176 H (CH ₂ ) ₃ H CH ₂ OEt 1,4-di-Me-2-Ph-5-Imid O 7-177 H (CH ₂ ) ₃ H CH ₂ OEt 1,5-di-Me-2 -Ph-4-Imid O 7-178 H (CH ₂ ) ₃ H CH ₂ OEt 3,4-MdO-Ph O 7-179 H (CH ₂ ) ₃ H CH ₂ OEt 4- (4-MeO-Ph) -Ph O 7-180 H (CH ₂ ) ₃ H CH ₂ OEt 4- (3,4-MdO-Ph) -Ph O 7-181 H (CH ₂ ) ₃ H CH ₂ OEt 4- [PhSO ₂ N ( Me)]-Ph O 7-182 H (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-3) SO ₂ N (Me)]-Ph O 7-183 H (CH ₂ ) ₃ H CH ₂ OEt 4- (PhSO ₂ NH) -Ph O 7-184 H (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-3) SO ₂ NH] -Ph O 7-185 H (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-2) SO ₂ ] -Ph O 7-186 H (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-3) SO ₂ ] -Ph O 7-187 H (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-2) SO ₂ N (Me)]-Ph O 7-188 H (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-2) SO ₂ NH] -Ph O 7-189 H (CH ₂ ) ₃ H CH ₂ OEt 4- (4-Me-Ph) -Ph O 7-190 H (CH ₂ ) ₃ H CH ₂ OEt 4- (4-F-Ph) -Ph O 7-191 H (CH ₂ ) ₃ H CH ₂ OEt 4- (4-CF ₃ -Ph) -Ph O 7-192 H (CH ₂ ) ₃ H CH ₂ OEt 2- [4-Me-PhSO ₂ N (Me)]-5-Pyr O 7-193 H (CH ₂ ) ₃ H CH ₂ OEt 2-HO-5-Pyr O 7-1 94 H (CH ₂ ) ₃ H CH ₂ OEt 2-BzO-5-Pyr O 7-195 H (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-4) SO ₂ ] -Ph O 7-196 H (CH ₂ ) ₃ H CH ₂ OEt 4- (2,4-di-MeO-Ph) -Ph O 7-197 H (CH ₂ ) ₃ H CH ₂ OEt 4- (2,5-di-MeO-Ph ) -Ph O 7-198 H (CH ₂ ) ₃ H CH ₂ OEt 3-HO-Ph O 7-199 H (CH ₂ ) ₃ H CH ₂ OEt 4-HO-Ph O 7-200 H (CH ₂ ) ₃ H CH ₂ OEt 5-AcO-2-HO-3,4,6-tri-Me-Ph O 7-201 H (CH ₂ ) ₃ H CH ₂ OEt 4-HO-3,5-di-Me- Ph O 7-202 H (CH ₂ ) ₃ H CH ₂ OEt 3-AcO-Ph O 7-203 H (CH ₂ ) ₃ H CH ₂ OEt 4-AcO-Ph O ────────── ────────────────────────.

[0138]

[Table 8] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 8- 1 Me (CH ₂ ) ₃ H CH ₂ OEt Ph O 8- 2 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Np O 8- 3 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Np O 8- 4 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Me-Ph O 8- 5 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Et-Ph O 8-6 Me (CH ₂ ) ₃ H CH ₂ OEt 3-iPr-Ph O 8- 7 Me ( CH ₂ ) ₃ H CH ₂ OEt 4-iPr-Ph O 8- 8 Me (CH ₂ ) ₃ H CH ₂ OEt 3-tBu-Ph O 8- 9 Me (CH ₂ ) ₃ H CH ₂ OEt 4-tBu- Ph O 8- 10 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Cl-Ph O 8- 11 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Cl-Ph O 8- 12 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Br-Ph O 8- 13 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Br-Ph O 8- 14 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Ph-Ph O 8- 15 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Ph-Ph O 8- 16 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Bz-Ph O 8- 17 Me (CH ₂ ) ₃ H CH ₂ OEt 4- Bz-Ph O 8--18 Me (CH ₂ ) ₃ H CH ₂ OEt 3-PhO-Ph O 8--19 Me (CH ₂ ) ₃ H CH ₂ OEt 4-PhO-Ph O 8-20 Me (CH ₂ ) ₃ H CH ₂ OEt 3-PhS-Ph O 8- 21 Me (CH ₂ ) ₃ H CH ₂ OEt 4- PhS-Ph O 8- 22 Me (CH ₂ ) ₃ H CH ₂ OEt 3-PhSO ₂ -Ph O 8- 23 Me (CH ₂ ) ₃ H CH ₂ OEt 4-PhSO ₂ -Ph O 8- 24 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Imid-1) -Ph O 8-25 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Imid-1) -Ph O 8- 26 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Imid-4) -Ph O 8-27 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Imid-4) -Ph O 8-28 Me (CH ₂ ) ₃ H CH ₂ OEt 3 -(Fur-2) -Ph O 8-29 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Fur-2) -Ph O 8--30 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Thi- 2) -Ph O 8- 31 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Thi-2) -Ph O 8- 32 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Thi-3) -Ph O 8-33 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Thi-3) -Ph O 8-34 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Pyr-2) -Ph O 8- 35 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Pyr-2) -Ph O 8-36 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Pyr-3) -Ph O 8-37 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Pyr-3) -Ph O 8-38 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Pyr-4) -Ph O 8-39 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Pyr-4) -Ph O 8-40 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Oxa-2) -Ph O 8- 41 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Oxa-2) -Ph O 8-42 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Oxa-4) -Ph O 8-43 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Oxa-4) -Ph O 8-44 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Oxa-5) -Ph O 8-45 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Oxa-5 ) -Ph O 8-46 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Thiz-2) -Ph O 8-47 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Thiz-2) -Ph O 8- 48 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Thiz-4) -Ph O 8- 49 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Thiz-4) -Ph O 8- 50 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (Thiz-5) -Ph O 8-51 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Thiz-5) -Ph O 8-52 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Me-2-Pyrr O 8-53 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Ph-2-Pyrr O 8-54 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Bz -2-Pyrr O 8-55 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Me-2-Fur O 8-56 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Ph-2-Fur O 8-57 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Me-2-Thi O 8-58 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Ph-2-Thi O 8-59 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Me-3-Thi O 8- 60 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Ph-3-Thi O 8-61 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Me-3- Pyza O 8-62 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Ph-3-Pyza O 8- 63 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Me-2-Imid O 8 -64 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Ph-2-Imid O 8-65 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Me-4-Imid O 8- 66 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Ph-4-Imid O 8-67 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Oxa O 8-68 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Oxa O 8-69 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Me-4-Oxa O 8-70 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-4-Oxa O 8-71 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Me-5-Oxa O 8-72 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-5-Oxa O 8-73 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Me-2-Ph -5-Oxa O 8-74 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Me-2-Ph-4-Oxa O 8-75 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Thiz O 8- 76 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Thiz O 8-77 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Me-4-Thiz O 8-78 Me (CH ₂ ) ₃ H CH ₂ OEt 2- Ph-4-Thiz O 8- 79 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Me-5-Thiz O 8- 80 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-5-Thiz O 8- 81 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Me-2-Ph-5-Thiz O 8- 82 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Me-2-Ph-4-Thiz O 8- 83 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Me-4-Pyza O 8- 84 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Ph-4-Pyza O 8- 85 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Me-4-Isox O 8-86 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-4-Isox O 8-87 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Pyr O 8-88 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Pyr O 8-89 Me (CH ₂ ) ₃ H CH ₂ OEt 4- Pyr O 8-90 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Me-5-Pyr O 8-91 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Et-5-Pyr O 8- 92 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Ph-5-Pyr O 8-93 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Me-5-Pyr O 8-94 Me (CH ₂ ) ₃ H CH ₂ OEt 2 -Et-5-Pyr O 8- 95 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-5-Pyr O 8- 96 Me (CH ₂ ) ₃ H CH ₂ OEt 2-MeO-5-Pyr O 8 -97 Me (CH ₂ ) ₃ H CH ₂ OEt 2-EtO-5-Pyr O 8- 98 Me (CH ₂ ) ₃ H CH ₂ OEt 2-iPrO-5-Pyr O 8- 99 Me (CH ₂ ) ₃ H CH ₂ OEt 2-MeS-5-Pyr O 8-100 Me (CH ₂ ) ₃ H CH ₂ OEt 2-EtS-5-Pyr O 8-101 Me (CH ₂ ) ₃ H CH ₂ OEt 2-iPrS- 5-Pyr O 8-102 Me (CH ₂ ) ₃ H CH ₂ OEt 2-MeSO ₂ -5-Pyr O 8-103 Me (CH ₂ ) ₃ H CH ₂ OEt 2-EtSO ₂ -5-Pyr O 8- 104 Me (CH ₂ ) ₃ H CH ₂ OEt 2-iPrSO ₂ -5-Pyr O 8-105 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Bz-5-Pyr O 8-106 Me (CH ₂ ) ₃ H CH ₂ OEt 2-PhO-5-Pyr O 8-107 Me (CH ₂ ) ₃ H CH ₂ OEt 2-PhS-5-Pyr O 8-108 Me (CH ₂ ) ₃ H CH ₂ OEt 2-PhSO ₂ -5-Pyr O 8-109 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Me- 6-Pyr O 8-110 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Ph-6-Pyr O 8-111 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Me-6-Pyr O 8-112 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-6-Pyr O 8-113 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Me-4-Pym O 8-114 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-4-Pym O 8-115 Me (CH ₂ ) ₃ H CH ₂ OEt 2-MeO-4-Pym O 8-116 Me (CH ₂ ) ₃ H CH ₂ OEt 2-EtO-4-Pym O 8-117 Me (CH ₂ ) ₃ H CH ₂ OEt 2-iPrO-4-Pym O 8-118 Me (CH ₂ ) ₃ H CH ₂ OEt 2-MeS-4-Pym O 8-119 Me (CH ₂ ) ₃ H CH ₂ OEt 2-EtS-4-Pym O 8-120 Me (CH ₂ ) ₃ H CH ₂ OEt 2-iPrS-4-Pym O 8-121 Me (CH ₂ ) ₃ H CH ₂ OEt 6- MeS-4-Pym O 8-122 Me (CH ₂ ) ₃ H CH ₂ OEt 6-EtS-4-Pym O 8-123 Me (CH ₂ ) ₃ H CH ₂ OEt 6-iPrS-4-Pym O 8- 124 Me (CH ₂ ) ₃ H CH ₂ OEt 2-PhS-4-Pym O 8-125 Me (CH ₂ ) ₃ H CH ₂ OEt 2-MeSO ₂ -4-Pym O 8-126 Me (CH ₂ ) ₃ H CH ₂ OEt 2-EtSO ₂ -4-Pym O 8-127 Me (CH ₂ ) ₃ H CH ₂ OEt 2-iPrSO ₂ -4-Pym O 8-128 Me (CH ₂ ) ₃ H CH ₂ OEt 2- PhSO ₂ -4-Pym O 8-129 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Me-5-Pym O 8-130 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Ph-5-Pym O 8 -131 Me (CH ₂ ) ₃ H CH ₂ OEt 2-MeO-5-Pym O 8-132 Me (C H ₂ ) ₃ H CH ₂ OEt 2-EtO-5-Pym O 8-133 Me (CH ₂ ) ₃ H CH ₂ OEt 2-iPrO-5-Pym O 8-134 Me (CH ₂ ) ₃ H CH ₂ OEt 2-MeS-5-Pym O 8-135 Me (CH ₂ ) ₃ H CH ₂ OEt 2-EtS-5-Pym O 8-136 Me (CH ₂ ) ₃ H CH ₂ OEt 2-iPrS-5-Pym O 8-137 Me (CH ₂ ) ₃ H CH ₂ OEt 2-PhS-5-Pym O 8-138 Me (CH ₂ ) ₃ H CH ₂ OEt 2-MeSO ₂ -5-Pym O 8-139 Me (CH ₂ ) ₃ H CH ₂ OEt 2-EtSO ₂ -5-Pym O 8-140 Me (CH ₂ ) ₃ H CH ₂ OEt 2-iPrSO ₂ -5-Pym O 8-141 Me (CH ₂ ) ₃ H CH ₂ OEt 2-PhSO ₂ -5-Pym O 8-142 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Ind O 8-143 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Ind O 8-144 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Me-2-Ind O 8-145 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Me-3-Ind O 8-146 Me (CH ₂ ) ₃ H CH ₂ OEt 2- Bimid O 8-147 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Boxa O 8-148 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Bthiz O 8-149 Me (CH ₂ ) ₃ H CH ₂ OEt 2 -Quin O 8-150 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Quin O 8-151 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Quin O 8-152 Me (CH ₂ ) ₃ H CH ₂ OEt 1-iQuin O 8-153 Me (CH ₂ ) ₃ H CH ₂ OEt 3-iQuin O 8-154 Me (CH ₂ ) ₃ H CH ₂ OEt 4-iQuin O 8-155 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Me O-Ph O 8-156 Me (CH ₂ ) ₃ H CH ₂ OEt 4-MeO-Ph O 8-157 Me (CH ₂ ) ₃ H CH ₂ OEt 3-EtO-Ph O 8-158 Me (CH ₂ ) ₃ H CH ₂ OEt 4-EtO-Ph O 8-159 Me (CH ₂ ) ₃ H CH ₂ OEt 3-iPrO-Ph O 8-160 Me (CH ₂ ) ₃ H CH ₂ OEt 4-iPrO-Ph O 8 -161 Me (CH ₂ ) ₃ H CH ₂ OEt 3-MeS-Ph O 8-162 Me (CH ₂ ) ₃ H CH ₂ OEt 4-MeS-Ph O 8-163 Me (CH ₂ ) ₃ H CH ₂ OEt 3-EtS-Ph O 8-164 Me (CH ₂ ) ₃ H CH ₂ OEt 4-EtS-Ph O 8-165 Me (CH ₂ ) ₃ H CH ₂ OEt 3-iPrS-Ph O 8-166 Me (CH ₂ ) ₃ H CH ₂ OEt 4-iPrS-Ph O 8-167 Me (CH ₂ ) ₃ H CH ₂ OEt 3-MeSO ₂ -Ph O 8-168 Me (CH ₂ ) ₃ H CH ₂ OEt 4-MeSO ₂ -Ph O 8-169 Me (CH ₂ ) ₃ H CH ₂ OEt 3-EtSO ₂ -Ph O 8-170 Me (CH ₂ ) ₃ H CH ₂ OEt 4-EtSO ₂ -Ph O 8-171 Me (CH ₂ ) ₃ H CH ₂ OEt 3-iPrSO ₂ -Ph O 8-172 Me (CH ₂ ) ₃ H CH ₂ OEt 4-iPrSO ₂ -Ph O 8-173 Me (CH ₂ ) ₃ H CH ₂ OEt 3- (1 -Me-Imid-4) -Ph O 8-174 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (1-Me-Imid-4) -Ph O 8-175 Me (CH ₂ ) ₃ H CH ₂ OEt 1-Me-2-Ph-4-Imid O 8-176 Me (CH ₂ ) ₃ H CH ₂ OEt 1,4-di-Me-2-Ph-5-Imid O 8-177 Me (CH ₂ ) ₃ H CH ₂ OEt 1,5-di-Me-2-Ph-4-Imid O 8-178 M e (CH ₂ ) ₃ H CH ₂ OEt 3,4-MdO-Ph O 8-179 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (4-MeO-Ph) -Ph O 8-180 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (3,4-MdO-Ph) -Ph O 8-181 Me (CH ₂ ) ₃ H CH ₂ OEt 4- [PhSO ₂ N (Me)]-Ph O 8-182 Me (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-3) SO ₂ N (Me)]-Ph O 8-183 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (PhSO ₂ NH) -Ph O 8-184 Me (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-3) SO ₂ NH] -Ph O 8-185 Me (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-2) SO ₂ ] -Ph O 8-186 Me (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-3) SO ₂ ] -Ph O 8-187 Me (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr -2) SO ₂ N (Me)]-Ph O 8-188 Me (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-2) SO ₂ NH] -Ph O 8-189 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (4-Me-Ph) -Ph O 8-190 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (4-F-Ph) -Ph O 8-191 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (4-CF ₃ -Ph) -Ph O 8-192 Me (CH ₂ ) ₃ H CH ₂ OEt 2- [4-Me-PhSO ₂ N (Me)]-5-Pyr O 8 -193 Me (CH ₂ ) ₃ H CH ₂ OEt 2-HO-5-Pyr O 8-194 Me (CH ₂ ) ₃ H CH ₂ OEt 2-BzO-5-Pyr O 8-195 Me (CH ₂ ) ₃ H CH ₂ OEt 4-[(Pyr-4) SO ₂ ] -Ph O 8-196 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (2,4-di-MeO-Ph) -Ph O 8-197 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (2,5-di-MeO- Ph) -Ph O 8-198 Me (CH ₂ ) ₃ H CH ₂ OEt 3-HO-Ph O 8-199 Me (CH ₂ ) ₃ H CH ₂ OEt 4-HO-Ph O 8-200 Me (CH ₂ ) ₃ H CH ₂ OEt 5-AcO-2-HO-3,4,6-tri-Me-Ph O 8-201 Me (CH ₂ ) ₃ H CH ₂ OEt 4-HO-3,5-di-Me -Ph O 8-202 Me (CH ₂ ) ₃ H CH ₂ OEt 3-AcO-Ph O 8-203 Me (CH ₂ ) ₃ H CH ₂ OEt 4-AcO-Ph O ───────── ─────────────────────────.

[0139]

[Table 9] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 9-1 H CH (Me) CH ₂ H CH ₂ OEt Ph O 9- 2 H CH (Me) CH ₂ H CH ₂ OEt 1-Np O 9- 3 H CH (Me) CH ₂ H CH ₂ OEt 2-Np O 9- 4 H CH (Me) CH ₂ H CH ₂ OEt 4-Me-Ph O 9- 5 H CH (Me) CH ₂ H CH ₂ OEt 4-Et-Ph O 9-6 H CH (Me) CH ₂ H CH ₂ OEt 3-iPr-Ph O 9- 7 H CH (Me) CH ₂ H CH ₂ OEt 4-iPr-Ph O 9- 8 H CH (Me) CH ₂ H CH ₂ OEt 3-tBu-Ph O 9- 9 H CH (Me) CH ₂ H CH ₂ OEt 4-tBu-Ph O 9- 10 H CH (Me) CH ₂ H CH ₂ OEt 3-Cl-Ph O 9- 11 H CH (Me) CH ₂ H CH ₂ OEt 4-Cl-Ph O 9- 12 H CH (Me) CH ₂ H CH ₂ OEt 3-Br-Ph O 9- 13 H CH (Me) CH ₂ H CH ₂ OEt 4-Br-Ph O 9- 14 H CH (Me) CH ₂ H CH ₂ OEt 3-Ph-Ph O 9-15 H CH (Me) CH ₂ H CH ₂ OEt 4-Ph-Ph O 9-16 H CH (Me) CH ₂ H CH ₂ OEt 3-Bz-Ph O 9-17 H CH (Me) CH ₂ H CH ₂ OEt 4-Bz-Ph O 9-18 H CH (Me) CH ₂ H CH ₂ OEt 3-PhO-Ph O 9-19 H CH (Me) CH ₂ H CH ₂ OEt 4-PhO-Ph O 9-20 H CH (Me) CH ₂ H CH ₂ OEt 3-PhS-Ph O 9- 21 H CH (Me) CH ₂ H CH ₂ OEt 4-PhS-Ph O 9-22 H CH (Me) CH ₂ H CH ₂ OEt 3-PhSO ₂ -Ph O 9-23 H CH (Me) CH ₂ H CH ₂ OEt 4-PhSO ₂ -Ph O 9 -24 H CH (Me) CH ₂ H CH ₂ OEt 3- (Imid-1) -Ph O 9- 25 H CH (Me) CH ₂ H CH ₂ OEt 4- (Imid-1) -Ph O 9- 26 H CH (Me) CH ₂ H CH ₂ OEt 3- (Imid-4) -Ph O 9- 27 H CH (Me) CH ₂ H CH ₂ OEt 4- (Imid-4) -Ph O 9- 28 H CH (Me) CH ₂ H CH ₂ OEt 3- (Fur-2) -Ph O 9- 29 H CH (Me) CH ₂ H CH ₂ OEt 4- (Fur-2) -Ph O 9-30 H CH (Me ) CH ₂ H CH ₂ OEt 3- (Thi-2) -Ph O 9- 31 H CH (Me) CH ₂ H CH ₂ OEt 4- (Thi-2) -Ph O 9- 32 H CH (Me) CH ₂ H CH ₂ OEt 3- (Thi-3) -Ph O 9- 33 H CH (Me) CH ₂ H CH ₂ OEt 4- (Thi-3) -Ph O 9- 34 H CH (Me) CH ₂ H CH ₂ OEt 3- (Pyr-2) -Ph O 9- 35 H CH (Me) CH ₂ H CH ₂ OEt 4- (Pyr-2) -Ph O 9- 36 H CH (Me) CH ₂ H CH ₂ OEt 3- (Pyr-3) -Ph O 9- 37 H CH (Me) CH ₂ H CH ₂ OEt 4- (Pyr-3) -Ph O 9- 38 H CH (Me) CH ₂ H CH ₂ OEt 3 -(Pyr-4) -Ph O 9- 39 H CH (Me) CH ₂ H CH ₂ OEt 4- (Pyr-4) -Ph O 9-40 H CH (Me) CH ₂ H CH ₂ OEt 3- ( Oxa-2) -Ph O 9- 41 H CH (Me) CH ₂ H CH ₂ OEt 4- (Oxa-2) -Ph O 9- 42 H CH (Me) CH ₂ H CH ₂ OEt 3- (Oxa-4) -Ph O 9- 43 H CH (Me) CH ₂ H CH ₂ OEt 4- (Oxa-4) -Ph O 9- 44 H CH (Me) CH ₂ H CH ₂ OEt 3- (Oxa-5) -Ph O 9- 45 H CH (Me) CH ₂ H CH ₂ OEt 4- (Oxa-5) -Ph O 9- 46 H CH (Me) CH ₂ H CH ₂ OEt 3- (Thiz-2) -Ph O 9- 47 H CH (Me) CH ₂ H CH ₂ OEt 4- (Thiz -2) -Ph O 9- 48 H CH (Me) CH ₂ H CH ₂ OEt 3- (Thiz-4) -Ph O 9- 49 H CH (Me) CH ₂ H CH ₂ OEt 4- (Thiz-4 ) -Ph O 9- 50 H CH (Me) CH ₂ H CH ₂ OEt 3- (Thiz-5) -Ph O 9- 51 H CH (Me) CH ₂ H CH ₂ OEt 4- (Thiz-5)- Ph O 9- 52 H CH (Me) CH ₂ H CH ₂ OEt 1-Me-2-Pyrr O 9- 53 H CH (Me) CH ₂ H CH ₂ OEt 1-Ph-2-Pyrr O 9- 54 H CH (Me) CH ₂ H CH ₂ OEt 1-Bz-2-Pyrr O 9- 55 H CH (Me) CH ₂ H CH ₂ OEt 5-Me-2-Fur O 9-56 H CH (Me) CH ₂ H CH ₂ OEt 5-Ph-2-Fur O 9- 57 H CH (Me) CH ₂ H CH ₂ OEt 5-Me-2-Thi O 9- 58 H CH (Me) CH ₂ H CH ₂ OEt 5- Ph-2-Thi O 9- 59 H CH (Me) CH ₂ H CH ₂ OEt 5-Me-3-Thi O 9-60 H CH (Me) CH ₂ H CH ₂ OEt 5-Ph-3-Thi O 9- 61 H CH (Me) CH ₂ H CH ₂ OEt 1-Me-3-Pyza O 9- 62 H CH (Me) CH ₂ H CH ₂ OEt 1-Ph-3-Pyza O 9- 63 H CH ( Me) CH ₂ H CH ₂ OEt 1-Me-2-Imid O 9 -64 H CH (Me) CH ₂ H CH ₂ OEt 1-Ph-2-Imid O 9- 65 H CH (Me) CH ₂ H CH ₂ OEt 1-Me-4-Imid O 9- 66 H CH (Me ) CH ₂ H CH ₂ OEt 1-Ph-4-Imid O 9- 67 H CH (Me) CH ₂ H CH ₂ OEt 4-Oxa O 9- 68 H CH (Me) CH ₂ H CH ₂ OEt 5-Oxa O 9- 69 H CH (Me) CH ₂ H CH ₂ OEt 2-Me-4-Oxa O 9- 70 H CH (Me) CH ₂ H CH ₂ OEt 2-Ph-4-Oxa O 9- 71 H CH (Me) CH ₂ H CH ₂ OEt 2-Me-5-Oxa O 9- 72 H CH (Me) CH ₂ H CH ₂ OEt 2-Ph-5-Oxa O 9- 73 H CH (Me) CH ₂ H CH ₂ OEt 4-Me-2-Ph-5-Oxa O 9- 74 H CH (Me) CH ₂ H CH ₂ OEt 5-Me-2-Ph-4-Oxa O 9- 75 H CH (Me) CH ₂ H CH ₂ OEt 4-Thiz O 9- 76 H CH (Me) CH ₂ H CH ₂ OEt 5-Thiz O 9- 77 H CH (Me) CH ₂ H CH ₂ OEt 2-Me-4-Thiz O 9 -78 H CH (Me) CH ₂ H CH ₂ OEt 2-Ph-4-Thiz O 9- 79 H CH (Me) CH ₂ H CH ₂ OEt 2-Me-5-Thiz O 9- 80 H CH (Me ) CH ₂ H CH ₂ OEt 2-Ph-5-Thiz O 9- 81 H CH (Me) CH ₂ H CH ₂ OEt 4-Me-2-Ph-5-Thiz O 9- 82 H CH (Me) CH ₂ H CH ₂ OEt 5-Me-2-Ph-4-Thiz O 9- 83 H CH (Me) CH ₂ H CH ₂ OEt 1-Me-4-Pyza O 9- 84 H CH (Me) CH ₂ H CH ₂ OEt 1-Ph-4-Pyza O 9- 85 H CH (Me) CH ₂ H CH ₂ OEt 2-Me-4-Isox O 9- 86 H CH (Me) CH ₂ H CH ₂ OEt 2-Ph -4-Isox O 9- 87 H CH (Me) CH ₂ H CH ₂ OEt 2-Pyr O 9- 88 H CH (Me) CH ₂ H CH ₂ OEt 3-Pyr O 9- 89 H CH (Me) CH ₂ H CH ₂ OEt 4-Pyr O 9- 90 H CH (Me) CH ₂ H CH ₂ OEt 3-Me-5-Pyr O 9- 91 H CH (Me) CH ₂ H CH ₂ OEt 3-Et-5-Pyr O 9 -92 H CH (Me) CH ₂ H CH ₂ OEt 3-Ph-5-Pyr O 9- 93 H CH (Me) CH ₂ H CH ₂ OEt 2-Me-5-Pyr O 9- 94 H CH (Me ) CH ₂ H CH ₂ OEt 2-Et-5-Pyr O 9- 95 H CH (Me) CH ₂ H CH ₂ OEt 2-Ph-5-Pyr O 9- 96 H CH (Me) CH ₂ H CH ₂ OEt 2-MeO-5-Pyr O 9- 97 H CH (Me) CH ₂ H CH ₂ OEt 2-EtO-5-Pyr O 9- 98 H CH (Me) CH ₂ H CH ₂ OEt 2-iPrO-5 -Pyr O 9- 99 H CH (Me) CH ₂ H CH ₂ OEt 2-MeS-5-Pyr O 9-100 H CH (Me) CH ₂ H CH ₂ OEt 2-EtS-5-Pyr O 9-101 H CH (Me) CH ₂ H CH ₂ OEt 2-iPrS-5-Pyr O 9-102 H CH (Me) CH ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pyr O 9-103 H CH (Me) CH ₂ H CH ₂ OEt 2-EtSO ₂ -5-Pyr O 9-104 H CH (Me) CH ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pyr O 9-105 H CH (Me) CH ₂ H CH ₂ OEt 2-Bz-5-Pyr O 9-106 H CH (Me) CH ₂ H CH ₂ OEt 2-PhO-5-Pyr O 9-107 H CH (Me) CH ₂ H CH ₂ OEt 2-PhS- 5-Pyr O 9-108 H CH (Me) CH ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pyr O 9-109 H CH (Me) CH ₂ H CH ₂ OEt 3-Me- 6-Pyr O 9-110 H CH (Me) CH ₂ H CH ₂ OEt 3-Ph-6-Pyr O 9-111 H CH (Me) CH ₂ H CH ₂ OEt 2-Me-6-Pyr O 9- 112 H CH (Me) CH ₂ H CH ₂ OEt 2-Ph-6-Pyr O 9-113 H CH (Me) CH ₂ H CH ₂ OEt 2-Me-4-Pym O 9-114 H CH (Me) CH ₂ H CH ₂ OEt 2-Ph-4-Pym O 9-115 H CH (Me) CH ₂ H CH ₂ OEt 2-MeO-4-Pym O 9-116 H CH (Me) CH ₂ H CH ₂ OEt 2-EtO-4-Pym O 9-117 H CH (Me) CH ₂ H CH ₂ OEt 2-iPrO-4-Pym O 9-118 H CH (Me) CH ₂ H CH ₂ OEt 2-MeS-4- Pym O 9-119 H CH (Me) CH ₂ H CH ₂ OEt 2-EtS-4-Pym O 9-120 H CH (Me) CH ₂ H CH ₂ OEt 2-iPrS-4-Pym O 9-121 H CH (Me) CH ₂ H CH ₂ OEt 6-MeS-4-Pym O 9-122 H CH (Me) CH ₂ H CH ₂ OEt 6-EtS-4-Pym O 9-123 H CH (Me) CH ₂ H CH ₂ OEt 6-iPrS-4-Pym O 9-124 H CH (Me) CH ₂ H CH ₂ OEt 2-PhS-4-Pym O 9-125 H CH (Me) CH ₂ H CH ₂ OEt 2- MeSO ₂ -4-Pym O 9-126 H CH (Me) CH ₂ H CH ₂ OEt 2-EtSO ₂ -4-Pym O 9-127 H CH (Me) CH ₂ H CH ₂ OEt 2-iPrSO ₂ -4 -Pym O 9-128 H CH (Me) CH ₂ H CH ₂ OEt 2-PhSO ₂ -4-Pym O 9-129 H CH (Me) CH ₂ H CH ₂ OEt 2-Me-5-Pym O 9- 130 H CH (Me) CH ₂ H CH ₂ OEt 2-Ph-5-Pym O 9-131 H CH (Me) CH ₂ H CH ₂ OEt 2-MeO-5-Pym O 9-132 H CH ( Me) CH ₂ H CH ₂ OEt 2-EtO-5-Pym O 9-133 H CH (Me) CH ₂ H CH ₂ OEt 2-iPrO-5-Pym O 9-134 H CH (Me) CH ₂ H CH ₂ OEt 2-MeS-5-Pym O 9-135 H CH (Me) CH ₂ H CH ₂ OEt 2-EtS-5-Pym O 9-136 H CH (Me) CH ₂ H CH ₂ OEt 2-iPrS- 5-Pym O 9-137 H CH (Me) CH ₂ H CH ₂ OEt 2-PhS-5-Pym O 9-138 H CH (Me) CH ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pym O 9 -139 H CH (Me) CH ₂ H CH ₂ OEt 2-EtSO ₂ -5-Pym O 9-140 H CH (Me) CH ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pym O 9-141 H CH (Me) CH ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pym O 9-142 H CH (Me) CH ₂ H CH ₂ OEt 2-Ind O 9-143 H CH (Me) CH ₂ H CH ₂ OEt 3-Ind O 9-144 H CH (Me) CH ₂ H CH ₂ OEt 1-Me-2-Ind O 9-145 H CH (Me) CH ₂ H CH ₂ OEt 1-Me-3-Ind O 9- 146 H CH (Me) CH ₂ H CH ₂ OEt 2-Bimid O 9-147 H CH (Me) CH ₂ H CH ₂ OEt 2-Boxa O 9-148 H CH (Me) CH ₂ H CH ₂ OEt 2- Bthiz O 9-149 H CH (Me) CH ₂ H CH ₂ OEt 2-Quin O 9-150 H CH (Me) CH ₂ H CH ₂ OEt 3-Quin O 9-151 H CH (Me) CH ₂ H CH ₂ OEt 4-Quin O 9-152 H CH (Me) CH ₂ H CH ₂ OEt 1-iQuin O 9-153 H CH (Me) CH ₂ H CH ₂ OEt 3-iQuin O 9-154 H CH (Me) CH ₂ H CH ₂ OEt 4-iQuin O 9-155 H CH (Me) CH ₂ H CH ₂ OEt 3-Me O-Ph O 9-156 H CH (Me) CH ₂ H CH ₂ OEt 4-MeO-Ph O 9-157 H CH (Me) CH ₂ H CH ₂ OEt 3-EtO-Ph O 9-158 H CH ( Me) CH ₂ H CH ₂ OEt 4-EtO-Ph O 9-159 H CH (Me) CH ₂ H CH ₂ OEt 3-iPrO-Ph O 9-160 H CH (Me) CH ₂ H CH ₂ OEt 4- iPrO-Ph O 9-161 H CH (Me) CH ₂ H CH ₂ OEt 3-MeS-Ph O 9-162 H CH (Me) CH ₂ H CH ₂ OEt 4-MeS-Ph O 9-163 H CH ( Me) CH ₂ H CH ₂ OEt 3-EtS-Ph O 9-164 H CH (Me) CH ₂ H CH ₂ OEt 4-EtS-Ph O 9-165 H CH (Me) CH ₂ H CH ₂ OEt 3- iPrS-Ph O 9-166 H CH (Me) CH ₂ H CH ₂ OEt 4-iPrS-Ph O 9-167 H CH (Me) CH ₂ H CH ₂ OEt 3-MeSO ₂ -Ph O 9-168 H CH (Me) CH ₂ H CH ₂ OEt 4-MeSO ₂ -Ph O 9-169 H CH (Me) CH ₂ H CH ₂ OEt 3-EtSO ₂ -Ph O 9-170 H CH (Me) CH ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 9-171 H CH (Me) CH ₂ H CH ₂ OEt 3-iPrSO ₂ -Ph O 9-172 H CH (Me) CH ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 9-173 H CH (Me) CH ₂ H CH ₂ OEt 3- (1-Me-Imid-4) -Ph O 9-174 H CH (Me) CH ₂ H CH ₂ OEt 4- (1-Me-Imid -4) -Ph O 9-175 H CH (Me) CH ₂ H CH ₂ OEt 1-Me-2-Ph-4-Imid O 9-176 H CH (Me) CH ₂ H CH ₂ OEt 1,4- di-Me-2-Ph-5-Imid O 9-177 H CH (Me) CH ₂ H CH ₂ OEt 1,5-di-Me-2-Ph-4-Imid O 9-178 H CH (Me) CH ₂ H CH ₂ OEt 3,4-MdO-Ph O 9-179 H CH (Me) CH ₂ H CH ₂ OEt 4- (4-MeO-Ph) -Ph O 9-180 H CH ( Me) CH ₂ H CH ₂ OEt 4- (3,4-MdO-Ph) -Ph O 9 -181 H CH (Me) CH ₂ H CH ₂ OEt 4- [PhSO ₂ N (Me)]-Ph O 9 -182 H CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ N (Me)]-Ph O 9-183 H CH (Me) CH ₂ H CH ₂ OEt 4- (PhSO ₂ NH) -Ph O 9-184 H CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ NH] -Ph O 9-185 H CH (Me) CH ₂ H CH ₂ OEt 4- [(Pyr-2) SO ₂ ] -Ph O 9-186 H CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ ] -Ph O 9-187 H CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ N (Me)]-Ph O 9-188 H CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ NH] -Ph O 9-189 H CH (Me) CH ₂ H CH ₂ OEt 4- (4-Me-Ph) -Ph O 9-190 H CH (Me) CH ₂ H CH ₂ OEt 4- (4-F-Ph) -Ph O 9-191 H CH (Me) CH ₂ H CH ₂ OEt 4- (4-CF ₃ -Ph) -Ph O 9-192 H CH (Me) CH ₂ H CH ₂ OEt 2- [4-Me -PhSO ₂ N (Me)]-5-Pyr O 9-193 H CH (Me) CH ₂ H CH ₂ OEt 2-HO-5-Pyr O 9-194 H CH (Me) CH ₂ H CH ₂ OEt 2 -BzO-5-Pyr O 9-195 H CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-4) SO ₂ ] -Ph O 9-196 H CH (Me) CH ₂ H CH ₂ OEt 4 -(2,4-di-MeO-Ph) -Ph O 9-197 H CH (Me) CH ₂ H CH ₂ OEt 4- (2,5-di-MeO- Ph) -Ph O 9-198 H CH (Me) CH ₂ H CH ₂ OEt 3-HO-Ph O 9-199 H CH (Me) CH ₂ H CH ₂ OEt 4-HO-Ph O 9-200 H CH (Me) CH ₂ H CH ₂ OEt 5-AcO-2-HO-3,4,6-tri-Me-Ph O 9-201 H CH (Me) CH ₂ H CH ₂ OEt 4-HO-3,5 -di-Me-Ph O 9-202 H CH (Me) CH ₂ H CH ₂ OEt 3-AcO-Ph O 9-203 H CH (Me) CH ₂ H CH ₂ OEt 4-AcO-Ph O ─── ───────────────────────────────.

[0140]

[Table 10] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 10- 1 Me CH (Me) CH ₂ H CH ₂ OEt Ph O 10- 2 Me CH (Me) CH ₂ H CH ₂ OEt 1-Np O 10- 3 Me CH (Me) CH ₂ H CH ₂ OEt 2-Np O 10- 4 Me CH (Me) CH ₂ H CH ₂ OEt 4-Me-Ph O 10- 5 Me CH (Me) CH ₂ H CH ₂ OEt 4-Et-Ph O 10- 6 Me CH (Me) CH ₂ H CH ₂ OEt 3-iPr-Ph O 10- 7 Me CH (Me) CH ₂ H CH ₂ OEt 4-iPr-Ph O 10- 8 Me CH (Me) CH ₂ H CH ₂ OEt 3-tBu-Ph O 10- 9 Me CH (Me) CH ₂ H CH ₂ OEt 4-tBu-Ph O 10-10 Me CH (Me) CH ₂ H CH ₂ OEt 3-Cl-Ph O 10- 11 Me CH (Me) CH ₂ H CH ₂ OEt 4-Cl-Ph O 10- 12 Me CH (Me) CH ₂ H CH ₂ OEt 3-Br-Ph O 10- 13 Me CH (Me) CH ₂ H CH ₂ OEt 4-Br-Ph O 10- 14 Me CH (Me) CH ₂ H CH ₂ OEt 3-Ph-Ph O 10-15 Me CH (Me) CH ₂ H CH ₂ OEt 4-Ph-Ph O 10-16 Me CH (Me) CH ₂ H CH ₂ OEt 3-Bz-Ph O 10-17 Me CH (Me) CH ₂ H CH ₂ OEt 4-Bz-Ph O 10-18 Me CH (Me) CH ₂ H CH ₂ OEt 3-PhO-Ph O 10-19 Me CH (Me) CH ₂ H CH ₂ OEt 4-PhO-Ph O 10-20 Me CH (Me) CH ₂ H CH ₂ OEt 3-PhS-Ph O 10- 21 Me CH (Me) CH ₂ H CH ₂ OEt 4-PhS-Ph O 10- 22 Me CH (Me) CH ₂ H CH ₂ OEt 3-PhSO ₂ -Ph O 10- 23 Me CH (Me) CH ₂ H CH ₂ OEt 4-PhSO ₂ -Ph O 10- 24 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Imid-1) -Ph O 10- 25 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Imid-1) -Ph O 10- 26 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Imid-4) -Ph O 10- 27 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Imid-4) -Ph O 10- 28 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Fur-2) -Ph O 10- 29 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Fur-2) -Ph O 10-30 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Thi-2) -Ph O 10- 31 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Thi-2) -Ph O 10- 32 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Thi-3) -Ph O 10- 33 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Thi-3) -Ph O 10- 34 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Pyr-2) -Ph O 10- 35 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Pyr -2) -Ph O 10- 36 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Pyr-3) -Ph O 10- 37 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Pyr-3 ) -Ph O 10- 38 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Pyr-4) -Ph O 10- 39 Me CH (Me) CH ₂ H CH ₂ OEt 4- ( Pyr-4) -Ph O 10-40 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Oxa-2) -Ph O 10- 41 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Oxa- 2) -Ph O 10- 42 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Oxa-4) -Ph O 10- 43 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Oxa-4) -Ph O 10- 44 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Oxa-5) -Ph O 10- 45 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Oxa-5) -Ph O 10- 46 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Thiz-2) -Ph O 10- 47 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Thiz-2) -Ph O 10 -48 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Thiz-4) -Ph O 10- 49 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Thiz-4) -Ph O 10-50 Me CH (Me) CH ₂ H CH ₂ OEt 3- (Thiz-5) -Ph O 10- 51 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Thiz-5) -Ph O 10- 52 Me CH (Me) CH ₂ H CH ₂ OEt 1-Me-2-Pyrr O 10- 53 Me CH (Me) CH ₂ H CH ₂ OEt 1-Ph-2-Pyrr O 10- 54 Me CH (Me) CH ₂ H CH ₂ OEt 1-Bz-2-Pyrr O 10- 55 Me CH (Me) CH ₂ H CH ₂ OEt 5-Me-2-Fur O 10- 56 Me CH (Me) CH ₂ H CH ₂ OEt 5-Ph -2-Fur O 10- 57 Me CH (Me) CH ₂ H CH ₂ OEt 5-Me-2-Thi O 10- 58 Me CH (Me) CH ₂ H CH ₂ OEt 5-Ph-2-Thi O 10 -59 Me CH (Me) CH ₂ H CH ₂ OEt 5-Me-3-Thi O 10-60 Me CH (Me) CH ₂ H CH ₂ OEt 5-Ph-3-Thi O 10- 61 Me CH (Me) CH ₂ H CH ₂ OEt 1-Me-3-Pyza O 10- 62 Me CH (Me) CH ₂ H CH ₂ OEt 1-Ph-3-Pyza O 10- 63 Me CH (Me) CH ₂ H CH ₂ OEt 1-Me-2-Imid O 10- 64 Me CH (Me) CH ₂ H CH ₂ OEt 1-Ph-2-Imid O 10- 65 Me CH (Me) CH ₂ H CH ₂ OEt 1- Me-4-Imid O 10- 66 Me CH (Me) CH ₂ H CH ₂ OEt 1-Ph-4-Imid O 10- 67 Me CH (Me) CH ₂ H CH ₂ OEt 4-Oxa O 10- 68 Me CH (Me) CH ₂ H CH ₂ OEt 5-Oxa O 10- 69 Me CH (Me) CH ₂ H CH ₂ OEt 2-Me-4-Oxa O 10- 70 Me CH (Me) CH ₂ H CH ₂ OEt 2-Ph-4-Oxa O 10- 71 Me CH (Me) CH ₂ H CH ₂ OEt 2-Me-5-Oxa O 10- 72 Me CH (Me) CH ₂ H CH ₂ OEt 2-Ph-5- Oxa O 10- 73 Me CH (Me) CH ₂ H CH ₂ OEt 4-Me-2-Ph-5-Oxa O 10- 74 Me CH (Me) CH ₂ H CH ₂ OEt 5-Me-2-Ph- 4-Oxa O 10- 75 Me CH (Me) CH ₂ H CH ₂ OEt 4-Thiz O 10- 76 Me CH (Me) CH ₂ H CH ₂ OEt 5-Thiz O 10- 77 Me CH (Me) CH ₂ H CH ₂ OEt 2-Me-4-Thiz O 10- 78 Me CH (Me) CH ₂ H CH ₂ OEt 2-Ph-4-Thiz O 10- 79 Me CH (Me) CH ₂ H CH ₂ OEt 2- Me-5-Thiz O 10- 80 Me CH (Me) CH ₂ H CH ₂ OEt 2-Ph-5-Thiz O 10- 81 Me CH (Me) CH ₂ H CH ₂ OEt 4-Me-2-Ph- 5-Thiz O 10- 82 Me CH (Me) CH ₂ H CH ₂ OEt 5-Me-2-Ph-4-Thiz O 10- 83 Me CH (Me) CH ₂ H CH ₂ OEt 1-Me-4-Pyza O 10- 84 Me CH (Me) CH ₂ H CH ₂ OEt 1-Ph-4-Pyza O 10- 85 Me CH (Me) CH ₂ H CH ₂ OEt 2-Me-4-Isox O 10- 86 Me CH (Me) CH ₂ H CH ₂ OEt 2-Ph-4-Isox O 10- 87 Me CH (Me) CH ₂ H CH ₂ OEt 2 -Pyr O 10- 88 Me CH (Me) CH ₂ H CH ₂ OEt 3-Pyr O 10- 89 Me CH (Me) CH ₂ H CH ₂ OEt 4-Pyr O 10- 90 Me CH (Me) CH ₂ H CH ₂ OEt 3-Me-5-Pyr O 10- 91 Me CH (Me) CH ₂ H CH ₂ OEt 3-Et-5-Pyr O 10- 92 Me CH (Me) CH ₂ H CH ₂ OEt 3-Ph -5-Pyr O 10- 93 Me CH (Me) CH ₂ H CH ₂ OEt 2-Me-5-Pyr O 10- 94 Me CH (Me) CH ₂ H CH ₂ OEt 2-Et-5-Pyr O 10 -95 Me CH (Me) CH ₂ H CH ₂ OEt 2-Ph-5-Pyr O 10- 96 Me CH (Me) CH ₂ H CH ₂ OEt 2-MeO-5-Pyr O 10- 97 Me CH (Me ) CH ₂ H CH ₂ OEt 2-EtO-5-Pyr O 10- 98 Me CH (Me) CH ₂ H CH ₂ OEt 2-iPrO-5-Pyr O 10- 99 Me CH (Me) CH ₂ H CH ₂ OEt 2-MeS-5-Pyr O 10-100 Me CH (Me) CH ₂ H CH ₂ OEt 2-EtS-5-Pyr O 10-101 Me CH (Me) CH ₂ H CH ₂ OEt 2-iPrS-5 -Pyr O 10-102 Me CH (Me) CH ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pyr O 10 -103 Me CH (Me) CH ₂ H CH ₂ OEt 2-EtSO ₂ -5-Pyr O 10 -104 Me CH (Me) CH ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pyr O 10- 105 Me CH (Me) CH ₂ H CH ₂ OEt 2-Bz-5-Pyr O 10-106 Me CH (Me) CH ₂ H CH ₂ OEt 2-PhO-5-Pyr O 10-107 Me CH (Me) CH ₂ H CH ₂ OEt 2-PhS-5-Pyr O 10-108 Me CH (Me) CH ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pyr O 10-109 Me CH (Me) CH ₂ H CH ₂ OEt 3-Me-6-Pyr O 10-110 Me CH (Me) CH ₂ H CH ₂ OEt 3-Ph-6-Pyr O 10-111 Me CH (Me) CH ₂ H CH ₂ OEt 2-Me-6 -Pyr O 10-112 Me CH (Me) CH ₂ H CH ₂ OEt 2-Ph-6-Pyr O 10-113 Me CH (Me) CH ₂ H CH ₂ OEt 2-Me-4-Pym O 10-114 Me CH (Me) CH ₂ H CH ₂ OEt 2-Ph-4-Pym O 10-115 Me CH (Me) CH ₂ H CH ₂ OEt 2-MeO-4-Pym O 10-116 Me CH (Me) CH ₂ H CH ₂ OEt 2-EtO-4-Pym O 10-117 Me CH (Me) CH ₂ H CH ₂ OEt 2-iPrO-4-Pym O 10-118 Me CH (Me) CH ₂ H CH ₂ OEt 2 -MeS-4-Pym O 10-119 Me CH (Me) CH ₂ H CH ₂ OEt 2-EtS-4-Pym O 10-120 Me CH (Me) CH ₂ H CH ₂ OEt 2-iPrS-4-Pym O 10-121 Me CH (Me) CH ₂ H CH ₂ OEt 6-MeS-4-Pym O 10-122 Me CH (Me) CH ₂ H CH ₂ OEt 6-EtS-4-Pym O 10-123 Me CH (Me) CH ₂ H CH ₂ OEt 6-iPrS-4-Pym O 10-124 Me CH (Me) CH ₂ H CH ₂ OEt 2-PhS-4-Pym O 10-125 Me CH (Me) CH ₂ H CH ₂ OEt 2-MeSO ₂ -4-Pym O 10-126 Me CH (Me) CH ₂ H CH ₂ OEt 2 -EtSO ₂ -4-Pym O 10-127 Me CH (Me) CH ₂ H CH ₂ OEt 2-iPrSO ₂ -4-Pym O 10-128 Me CH (Me) CH ₂ H CH ₂ OEt 2-PhSO _2- 4-Pym O 10-129 Me CH (Me) CH ₂ H CH ₂ OEt 2-Me-5-Pym O 10-130 Me CH (Me) CH ₂ H CH ₂ OEt 2-Ph-5-Pym O 10- 131 Me CH (Me) CH ₂ H CH ₂ OEt 2-MeO-5-Pym O 10-132 Me CH (Me) CH ₂ H CH ₂ OEt 2-EtO-5-Pym O 10-133 Me CH (Me) CH ₂ H CH ₂ OEt 2-iPrO-5-Pym O 10-134 Me CH (Me) CH ₂ H CH ₂ OEt 2-MeS-5-Pym O 10-135 Me CH (Me) CH ₂ H CH ₂ OEt 2-EtS-5-Pym O 10-136 Me CH (Me) CH ₂ H CH ₂ OEt 2-iPrS-5-Pym O 10-137 Me CH (Me) CH ₂ H CH ₂ OEt 2-PhS-5- Pym O 10-138 Me CH (Me) CH ₂ H CH ₂ OEt 2-MeSO ₂ -5-Pym O 10-139 Me CH (Me) CH ₂ H CH ₂ OEt 2-EtSO ₂ -5-Pym O 10- 140 Me CH (Me) CH ₂ H CH ₂ OEt 2-iPrSO ₂ -5-Pym O 10-141 Me CH (Me) CH ₂ H CH ₂ OEt 2-PhSO ₂ -5-Pym O 10-142 Me CH ( Me) CH ₂ H CH ₂ OEt 2-Ind O 10-143 Me CH (Me) CH ₂ H CH ₂ OEt 3-Ind O 10-144 Me CH (Me) CH ₂ H CH ₂ OEt 1-Me-2- Ind O 10-145 Me CH (Me) CH ₂ H CH ₂ OEt 1-Me-3-Ind O 10-146 Me CH (Me) CH ₂ H CH ₂ OEt 2-Bimid O 10-147 Me CH (Me) CH ₂ H CH ₂ OEt 2-Boxa O 10-148 Me CH (M e) CH ₂ H CH ₂ OEt 2-Bthiz O 10-149 Me CH (Me) CH ₂ H CH ₂ OEt 2-Quin O 10-150 Me CH (Me) CH ₂ H CH ₂ OEt 3-Quin O 10- 151 Me CH (Me) CH ₂ H CH ₂ OEt 4-Quin O 10-152 Me CH (Me) CH ₂ H CH ₂ OEt 1-iQuin O 10-153 Me CH (Me) CH ₂ H CH ₂ OEt 3- iQuin O 10-154 Me CH (Me) CH ₂ H CH ₂ OEt 4-iQuin O 10-155 Me CH (Me) CH ₂ H CH ₂ OEt 3-MeO-Ph O 10-156 Me CH (Me) CH ₂ H CH ₂ OEt 4-MeO-Ph O 10-157 Me CH (Me) CH ₂ H CH ₂ OEt 3-EtO-Ph O 10-158 Me CH (Me) CH ₂ H CH ₂ OEt 4-EtO-Ph O 10-159 Me CH (Me) CH ₂ H CH ₂ OEt 3-iPrO-Ph O 10-160 Me CH (Me) CH ₂ H CH ₂ OEt 4-iPrO-Ph O 10-161 Me CH (Me) CH ₂ H CH ₂ OEt 3-MeS-Ph O 10-162 Me CH (Me) CH ₂ H CH ₂ OEt 4-MeS-Ph O 10-163 Me CH (Me) CH ₂ H CH ₂ OEt 3-EtS-Ph O 10-164 Me CH (Me) CH ₂ H CH ₂ OEt 4-EtS-Ph O 10-165 Me CH (Me) CH ₂ H CH ₂ OEt 3-iPrS-Ph O 10-166 Me CH (Me) CH ₂ H CH ₂ OEt 4-iPrS-Ph O 10-167 Me CH (Me) CH ₂ H CH ₂ OEt 3-MeSO ₂ -Ph O 10-168 Me CH (Me) CH ₂ H CH ₂ OEt 4-MeSO _2- Ph O 10-169 Me CH (Me) CH ₂ H CH ₂ OEt 3-EtSO ₂ -Ph O 10-170 Me CH (Me) CH ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 10-171 Me CH ( Me ) CH ₂ H CH ₂ OEt 3-iPrSO ₂ -Ph O 10-172 Me CH (Me) CH ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 10-173 Me CH (Me) CH ₂ H CH ₂ OEt 3 -(1-Me-Imid-4) -Ph O 10-174 Me CH (Me) CH ₂ H CH ₂ OEt 4- (1-Me-Imid-4) -Ph O 10-175 Me CH (Me) CH ₂ H CH ₂ OEt 1-Me-2-Ph-4-Imid O 10-176 Me CH (Me) CH ₂ H CH ₂ OEt 1,4-di-Me-2-Ph-5-Imid O 10-177 Me CH (Me) CH ₂ H CH ₂ OEt 1,5-di-Me-2-Ph-4-Imid O 10-178 Me CH (Me) CH ₂ H CH ₂ OEt 3,4-MdO-Ph O 10 -179 Me CH (Me) CH ₂ H CH ₂ OEt 4- (4-MeO-Ph) -Ph O 10 -180 Me CH (Me) CH ₂ H CH ₂ OEt 4- (3,4-MdO-Ph) -Ph O 10-181 Me CH (Me) CH ₂ H CH ₂ OEt 4- [PhSO ₂ N (Me)]-Ph
O 10-182 Me CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ N (Me)]-Ph O 10-183 Me CH (Me) CH ₂ H CH ₂ OEt 4- ( PhSO ₂ NH) -Ph O 10-184 Me CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ NH] -Ph O 10-185 Me CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ ] -Ph O 10-186 Me CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-3) SO ₂ ] -Ph O 10-187 Me CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ N (Me)]-Ph O 10-188 Me CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-2) SO ₂ NH] -Ph O 10-189 Me CH (Me) CH ₂ H CH ₂ OEt 4- (4-Me-Ph) -Ph O 10-190 Me CH (Me) CH ₂ H CH ₂ OEt 4- (4-F- Ph) -Ph O 10-191 Me CH (Me) CH ₂ H CH ₂ OEt 4- (4-CF ₃ -Ph) -Ph O 10-192 Me CH (Me) CH ₂ H CH ₂ OEt 2- [4 -Me-PhSO ₂ N (Me)]-5-Pyr O 10-193 Me CH (Me) CH ₂ H CH ₂ OEt 2-HO-5-Pyr O 10-194 Me CH (Me) CH ₂ H CH ₂ OEt 2-BzO-5-Pyr O 10-195 Me CH (Me) CH ₂ H CH ₂ OEt 4-[(Pyr-4) SO ₂ ] -Ph O 10-196 Me CH (Me) CH ₂ H CH ₂ OEt 4- (2,4-di-MeO-Ph) -Ph O 10-197 Me CH (Me) CH ₂ H CH ₂ OEt 4- (2,5-di-MeO-Ph) -Ph O 10-198 Me CH (Me) CH ₂ H CH ₂ OEt 3-HO-Ph O 10-199 Me CH (Me) CH ₂ H CH ₂ OEt 4-HO-Ph O 10-200 Me CH (Me) CH ₂ H CH ₂ OEt 5-AcO-2-HO-3,4,6-tri-Me-Ph O 10-201 Me CH (Me) CH ₂ H CH ₂ OEt 4-HO-3,5-di-Me-Ph O 10-202 Me CH (Me) CH ₂ H CH ₂ OEt 3-AcO-Ph O 10 -203 Me CH (Me) CH ₂ H CH ₂ OEt 4-AcO-Ph O ─────────────────────────────── ───.

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[Table 11] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 11- 1 HC (Me) ₂ CH ₂ H CH ₂ OEt 4-Et-Ph O 11- 2 HC (Me) ₂ CH ₂ H CH ₂ OEt 4-iPr-Ph O 11-3 HC (Me) ₂ CH ₂ H CH ₂ OEt 3-Ph-Ph O 11 -4 HC (Me) ₂ CH ₂ H CH ₂ OEt 4-Ph-Ph O 11-5 HC (Me) ₂ CH ₂ H CH ₂ OEt 3-Pyr O 11-6 HC (Me) ₂ CH ₂ H CH ₂ OEt 5-Me-3-Pyr O 11-7 HC (Me) ₂ CH ₂ H CH ₂ OEt 5-Et-3-Pyr O 11- 8 HC (Me) ₂ CH ₂ H CH ₂ OEt 5-Ph-3 -Pyr O 11- 9 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-Me-3-Pyr O 11-10 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-Et-3-Pyr O 11-11 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-Ph-3-Pyr O 11-12 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-MeO-3-Pyr O 11-13 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-EtO-3-Pyr O 11-14 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-iPrO-3-Pyr O 11-15 HC (Me) ₂ CH ₂ H CH ₂ OEt 6 -MeS-3-Pyr O 11- 16 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-EtS-3-Pyr O 11-17 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-iPrS-3-Pyr O 11-18 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-MeSO ₂ -3-Pyr O 11-19 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 11-20 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-iPrSO ₂ -3-Pyr O 11- 21 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-Bz-3-Pyr O 11-22 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-PhO-3-Pyr O 11-23 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-PhS- 3-Pyr O 11-24 HC (Me) ₂ CH ₂ H CH ₂ OEt 6-PhSO ₂ -3-Pyr O 11-25 HC (Me) ₂ CH ₂ H CH ₂ OEt 2-Quin O 11- 26 HC ( Me) ₂ CH ₂ H CH ₂ OEt 4-MeO-Ph O 11- 27 HC (Me) ₂ CH ₂ H CH ₂ OEt 4-EtO-Ph O 11- 28 HC (Me) ₂ CH ₂ H CH ₂ OEt 4 -iPrO-Ph O 11- 29 HC (Me) ₂ CH ₂ H CH ₂ OEt 4-MeS-Ph O 11-30 HC (Me) ₂ CH ₂ H CH ₂ OEt 4-EtS-Ph O 11- 31 HC ( Me) ₂ CH ₂ H CH ₂ OEt 4-iPrS-Ph O 11- 32 HC (Me) ₂ CH ₂ H CH ₂ OEt 4-MeSO ₂ -Ph O 11- 33 HC (Me) ₂ CH ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 11- 34 HC (Me) ₂ CH ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 11- 35 HC (Me) ₂ CH ₂ H CH ₂ OEt 4- (Pyr-2) Ph O 11- 36 HC (Me) ₂ CH ₂ H CH ₂ OEt 4- (Pyr-3) Ph O 11- 37 HC (Me) ₂ CH ₂ H CH ₂ OEt 4- (Pyr-3) Ph O 11- 38 HC (Me) ₂ CH ₂ H CH ₂ OEt 3-Ph-6-Py r O ──────────────────────────────────.

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[Table 12] Example R ¹ R ² R ³ Z W X Y compound number ──────────────────────────────────── 12- 1 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-Et-Ph O 12- 2 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-iPr-Ph O 12- 3 Me C (Me) ₂ CH ₂ H CH ₂ OEt 3-Ph- Ph O 12- 4 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-Ph-Ph O 12- 5 Me C (Me) ₂ CH ₂ H CH ₂ OEt 3-Pyr O 12- 6 Me C (Me) ₂ CH ₂ H CH ₂ OEt 5-Me-3-Pyr O 12- 7 Me C (Me) ₂ CH ₂ H CH ₂ OEt 5-Et-3-Pyr O 12- 8 Me C (Me) ₂ CH ₂ H CH ₂ OEt 5-Ph-3-Pyr O 12- 9 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-Me-3-Pyr O 12- 10 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6 -Et-3-Pyr O 12- 11 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-Ph-3-Pyr O 12-12 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-MeO-3 -Pyr O 12- 13 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-EtO-3-Pyr O 12- 14 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-iPrO-3-Pyr O 12 -15 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-MeS-3-Pyr O 12-16 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-EtS-3-Pyr O 12-17 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-iPrS-3-Pyr O 12-18 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-MeSO ₂ -3-Pyr O 12- 19 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 12-20 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6- iPrSO ₂ -3-Pyr O 12- 21 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-Bz-3-Pyr O 12-22 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-PhO-3 -Pyr O 12- 23 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-PhS-3-Pyr O 12- 24 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-PhSO ₂ -3-Pyr O 12- 25 Me C (Me) ₂ CH ₂ H CH ₂ OEt 2-Quin O 12- 26 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-MeO-Ph O 12- 27 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-EtO-Ph O 12- 28 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-iPrO-Ph O 12- 29 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-MeS -Ph O 12- 30 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-EtS-Ph O 12- 31 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-iPrS-Ph O 12- 32 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-MeSO ₂ -Ph O 12- 33 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 12- 34 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 12- 35 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4- (Pyr-2) Ph O 12- 36 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4- (Pyr-3) Ph O 12- 37 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4- (Pyr-3) Ph O 12- 38 Me C (Me) ₂ CH ₂ H CH ₂ OEt 3-Ph-6-Pyr O ─────────── ───────────────────────.

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[Table 13] Example R ¹ R ² R ³ ZW X Y Compound number ──────────────────────────────────── 13- 1 H CH ₂ CH (Me) H CH ₂ OEt 4-Et-Ph O 13- 2 H CH ₂ CH (Me) H CH ₂ OEt 4-iPr-Ph O 13- 3 H CH ₂ CH (Me) H CH ₂ OEt 3-Ph-Ph O 13 -4 H CH ₂ CH (Me) H CH ₂ OEt 4-Ph-Ph O 13-5 H CH ₂ CH (Me) H CH ₂ OEt 3-Pyr O 13-6 H CH ₂ CH (Me) H CH ₂ OEt 5-Me-3-Pyr O 13-7 H CH ₂ CH (Me) H CH ₂ OEt 5-Et-3-Pyr O 13- 8 H CH ₂ CH (Me) H CH ₂ OEt 5-Ph-3 -Pyr O 13- 9 H CH ₂ CH (Me) H CH ₂ OEt 6-Me-3-Pyr O 13- 10 H CH ₂ CH (Me) H CH ₂ OEt 6-Et-3-Pyr O 13-11 H CH ₂ CH (Me) H CH ₂ OEt 6-Ph-3-Pyr O 13-12 H CH ₂ CH (Me) H CH ₂ OEt 6-MeO-3-Pyr O 13- 13 H CH ₂ CH (Me ) H CH ₂ OEt 6-EtO-3-Pyr O 13-14 H CH ₂ CH (Me) H CH ₂ OEt 6-iPrO-3-Pyr O 13-15 H CH ₂ CH (Me) H CH ₂ OEt 6 -MeS-3-Pyr O 13- 16 H CH ₂ CH (Me) H CH ₂ OEt 6-EtS-3-Pyr O 13-17 H CH ₂ CH (Me) H CH ₂ OEt 6-iPrS-3-Pyr O 13-18 H CH ₂ CH (Me) H CH ₂ OEt 6-MeSO ₂ -3-Pyr O 13-19 H CH ₂ CH ( Me) H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 13-20 H CH ₂ CH (Me) H CH ₂ OEt 6-iPrSO ₂ -3-Pyr O 13- 21 H CH ₂ CH (Me) H CH ₂ OEt 6-Bz-3-Pyr O 13-22 H CH ₂ CH (Me) H CH ₂ OEt 6-PhO-3-Pyr O 13-23 H CH ₂ CH (Me) H CH ₂ OEt 6-PhS- 3-Pyr O 13-24 H CH ₂ CH (Me) H CH ₂ OEt 6-PhSO ₂ -3-Pyr O 13-25 H CH ₂ CH (Me) H CH ₂ OEt 2-Quin O 13- 26 H CH ₂ CH (Me) H CH ₂ OEt 4-MeO-Ph O 13- 27 H CH ₂ CH (Me) H CH ₂ OEt 4-EtO-Ph O 13- 28 H CH ₂ CH (Me) H CH ₂ OEt 4 -iPrO-Ph O 13- 29 H CH ₂ CH (Me) H CH ₂ OEt 4-MeS-Ph O 13-30 H CH ₂ CH (Me) H CH ₂ OEt 4-EtS-Ph O 13- 31 H CH ₂ CH (Me) H CH ₂ OEt 4-iPrS-Ph O 13- 32 H CH ₂ CH (Me) H CH ₂ OEt 4-MeSO ₂ -Ph O 13- 33 H CH ₂ CH (Me) H CH ₂ OEt 4-EtSO ₂ -Ph O 13- 34 H CH ₂ CH (Me) H CH ₂ OEt 4-iPrSO ₂ -Ph O 13- 35 H CH ₂ CH (Me) H CH ₂ OEt 4- (Pyr-2) Ph O 13- 36 H CH ₂ CH (Me) H CH ₂ OEt 4- (Pyr-3) Ph O 13- 37 H CH ₂ CH (Me) H CH ₂ OEt 4- (Pyr-3) Ph O 13- 38 H CH ₂ CH (Me) H CH ₂ OEt 3-Ph-6-Py r O ──────────────────────────────────.

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[Table 14] Example R ¹ R ² R ³ ZW X Y Compound number ──────────────────────────────────── 14- 1 Me CH ₂ CH (Me) H CH ₂ OEt 4-Et-Ph O 14- 2 Me CH ₂ CH (Me) H CH ₂ OEt 4-iPr-Ph O 14- 3 Me CH ₂ CH (Me) H CH ₂ OEt 3-Ph-Ph O 14 -4 Me CH ₂ CH (Me) H CH ₂ OEt 4-Ph-Ph O 14-5 Me CH ₂ CH (Me) H CH ₂ OEt 3-Pyr O 14-6 Me CH ₂ CH (Me) H CH ₂ OEt 5-Me-3-Pyr O 14- 7 Me CH ₂ CH (Me) H CH ₂ OEt 5-Et-3-Pyr O 14- 8 Me CH ₂ CH (Me) H CH ₂ OEt 5-Ph-3 -Pyr O 14- 9 Me CH ₂ CH (Me) H CH ₂ OEt 6-Me-3-Pyr O 14- 10 Me CH ₂ CH (Me) H CH ₂ OEt 6-Et-3-Pyr O 14- 11 Me CH ₂ CH (Me) H CH ₂ OEt 6-Ph-3-Pyr O 14-12 Me CH ₂ CH (Me) H CH ₂ OEt 6-MeO-3-Pyr O 14- 13 Me CH ₂ CH (Me ) H CH ₂ OEt 6-EtO-3-Pyr O 14-14 Me CH ₂ CH (Me) H CH ₂ OEt 6-iPrO-3-Pyr O 14-15 Me CH ₂ CH (Me) H CH ₂ OEt 6 -MeS-3-Pyr O 14- 16 Me CH ₂ CH (Me) H CH ₂ OEt 6-EtS -3-Pyr O 14- 17 Me CH ₂ CH (Me) H CH ₂ OEt 6-iPrS-3-Pyr O 14-18 Me CH ₂ CH (Me) H CH ₂ OEt 6-MeSO ₂ -3-Pyr O 14-19 Me CH ₂ CH (Me) H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 14-20 Me CH ₂ CH (Me) H CH ₂ OEt 6-iPrSO ₂ -3-Pyr O 14-21 Me CH ₂ CH (Me) H CH ₂ OEt 6-Bz-3-Pyr O 14-22 Me CH ₂ CH (Me) H CH ₂ OEt 6-PhO-3-Pyr O 14- 23 Me CH ₂ CH (Me) H CH ₂ OEt 6-PhS-3-Pyr O 14-24 Me CH ₂ CH (Me) H CH ₂ OEt 6-PhSO ₂ -3-Pyr O 14-25 Me CH ₂ CH (Me) H CH ₂ OEt 2 -Quin O 14- 26 Me CH ₂ CH (Me) H CH ₂ OEt 4-MeO-Ph O 14- 27 Me CH ₂ CH (Me) H CH ₂ OEt 4-EtO-Ph O 14- 28 Me CH ₂ CH (Me) H CH ₂ OEt 4-iPrO-Ph O 14- 29 Me CH ₂ CH (Me) H CH ₂ OEt 4-MeS-Ph O 14-30 Me CH ₂ CH (Me) H CH ₂ OEt 4-EtS -Ph O 14- 31 Me CH ₂ CH (Me) H CH ₂ OEt 4-iPrS-Ph O 14- 32 Me CH ₂ CH (Me) H CH ₂ OEt 4-MeSO ₂ -Ph O 14- 33 Me CH ₂ CH (Me) H CH ₂ OEt 4-EtSO ₂ -Ph O 14- 34 Me CH ₂ CH (Me) H CH ₂ OEt 4-iPrSO ₂ -Ph O 14- 35 Me CH ₂ CH (Me) H CH ₂ OEt 4- (Pyr-2) Ph O 14- 36 Me CH ₂ CH (Me) H CH ₂ OEt 4- (Pyr-3) Ph O 14- 37 Me CH ₂ CH (Me) H CH ₂ OEt 4- (Pyr -3) Ph O 14- 38 Me CH ₂ CH (Me) H CH ₂ OEt 3-Ph-6-Pyr O ────────────────────────────── ────.

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[Table 15] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 15- 1 H CH (Me) CH (Me ) H CH ₂ OEt 4-Et-Ph O 15- 2 H CH (Me) CH (Me) H CH ₂ OEt 4-iPr-Ph O 15- 3 H CH (Me) CH (Me) H CH ₂ OEt 3 -Ph-Ph O 15- 4 H CH (Me) CH (Me) H CH ₂ OEt 4-Ph-Ph O 15- 5 H CH (Me) CH (Me) H CH ₂ OEt 3-Pyr O 15-6 H CH (Me) CH (Me) H CH ₂ OEt 5-Me-3-Pyr O 15- 7 H CH (Me) CH (Me) H CH ₂ OEt 5-Et-3-Pyr O 15- 8 H CH (Me) CH (Me) H CH ₂ OEt 5-Ph-3-Pyr O 15- 9 H CH (Me) CH (Me) H CH ₂ OEt 6-Me-3-Pyr O 15-10 H CH (Me ) CH (Me) H CH ₂ OEt 6-Et-3-Pyr O 15- 11 H CH (Me) CH (Me) H CH ₂ OEt 6-Ph-3-Pyr O 15-12 H CH (Me) CH (Me) H CH ₂ OEt 6-MeO-3-Pyr O 15- 13 H CH (Me) CH (Me) H CH ₂ OEt 6-EtO-3-Pyr O 15- 14 H CH (Me) CH (Me ) H CH ₂ OEt 6-iPrO-3-Pyr O 15- 15 H CH (Me) CH (Me) H CH ₂ OEt 6-MeS-3-Pyr O 15-16 H CH (Me) CH (Me) H CH ₂ OEt 6-EtS -3-Pyr O 15- 17 H CH (Me) CH (Me) H CH ₂ OEt 6-iPrS-3-Pyr O 15- 18 H CH (Me) CH (Me) H CH ₂ OEt 6-MeSO _2- 3-Pyr O 15- 19 H CH (Me) CH (Me) H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 15-20 H CH (Me) CH (Me) H CH ₂ OEt 6-iPrSO _2- 3-Pyr O 15- 21 H CH (Me) CH (Me) H CH ₂ OEt 6-Bz-3-Pyr O 15-22 H CH (Me) CH (Me) H CH ₂ OEt 6-PhO-3- Pyr O 15-23 H CH (Me) CH (Me) H CH ₂ OEt 6-PhS-3-Pyr O 15-24 H CH (Me) CH (Me) H CH ₂ OEt 6-PhSO ₂ -3-Pyr O 15-25 H CH (Me) CH (Me) H CH ₂ OEt 2-Quin O 15- 26 H CH (Me) CH (Me) H CH ₂ OEt 4-MeO-Ph O 15- 27 H CH (Me ) CH (Me) H CH ₂ OEt 4-EtO-Ph O 15- 28 H CH (Me) CH (Me) H CH ₂ OEt 4-iPrO-Ph O 15- 29 H CH (Me) CH (Me) H CH ₂ OEt 4-MeS-Ph O 15-30 H CH (Me) CH (Me) H CH ₂ OEt 4-EtS-Ph O 15- 31 H CH (Me) CH (Me) H CH ₂ OEt 4-iPrS -Ph O 15- 32 H CH (Me) CH (Me) H CH ₂ OEt 4-MeSO ₂ -Ph O 15- 33 H CH (Me) CH (Me) H CH ₂ OEt 4-EtSO ₂ -Ph O 15 -34 H CH (Me) CH (Me) H CH ₂ OEt 4-iPrSO ₂ -Ph O 15- 35 H CH (Me) CH (Me) H CH ₂ OEt 4- (Pyr-2) Ph O 15- 36 H CH (Me) CH (Me) H CH ₂ OEt 4- (Pyr-3) Ph O 15- 37 H CH (Me) CH (Me) H CH ₂ OEt 4- (Pyr-3) Ph O 15- 38 H CH (Me) CH (Me) H CH ₂ OEt 3-Ph-6-Pyr O ──────────────────────────── ──────.

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[Table 16] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 16-1 Me CH (Me) CH (Me ) H CH ₂ OEt 4-Et-Ph O 16- 2 Me CH (Me) CH (Me) H CH ₂ OEt 4-iPr-Ph O 16- 3 Me CH (Me) CH (Me) H CH ₂ OEt 3 -Ph-Ph O 16- 4 Me CH (Me) CH (Me) H CH ₂ OEt 4-Ph-Ph O 16- 5 Me CH (Me) CH (Me) H CH ₂ OEt 3-Pyr O 16-6 Me CH (Me) CH (Me) H CH ₂ OEt 5-Me-3-Pyr O 16- 7 Me CH (Me) CH (Me) H CH ₂ OEt 5-Et-3-Pyr O 16- 8 Me CH (Me) CH (Me) H CH ₂ OEt 5-Ph-3-Pyr O 16- 9 Me CH (Me) CH (Me) H CH ₂ OEt 6-Me-3-Pyr O 16-10 Me CH (Me ) CH (Me) H CH ₂ OEt 6-Et-3-Pyr O 16-11 Me CH (Me) CH (Me) H CH ₂ OEt 6-Ph-3-Pyr O 16-12 Me CH (Me) CH (Me) H CH ₂ OEt 6-MeO-3-Pyr O 16-13 Me CH (Me) CH (Me) H CH ₂ OEt 6-EtO-3-Pyr O 16-14 Me CH (Me) CH (Me ) H CH ₂ OEt 6-iPrO-3-Pyr O 16- 15 Me CH (Me) CH (Me) H CH ₂ OEt 6-MeS-3-Pyr O 16-16 Me CH (Me) CH (Me) H CH ₂ OEt 6-EtS-3-Pyr O 16-17 Me CH (Me) CH (Me) H CH ₂ OEt 6-iPrS-3-Pyr O 16-18 Me CH (Me) CH (Me) H CH ₂ OEt 6-MeSO ₂ -3-Pyr O 16-19 Me CH (Me) CH (Me) H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 16-20 Me CH (Me) CH (Me) H CH ₂ OEt 6-iPrSO ₂ -3-Pyr O 16-21 Me CH (Me) CH (Me) H CH ₂ OEt 6-Bz-3-Pyr O 16-22 Me CH (Me) CH (Me) H CH ₂ OEt 6-PhO-3-Pyr O 16-23 Me CH (Me) CH (Me) H CH ₂ OEt 6-PhS-3-Pyr O 16-24 Me CH (Me) CH (Me) H CH ₂ OEt 6 -PhSO ₂ -3-Pyr O 16- 25 Me CH (Me) CH (Me) H CH ₂ OEt 2-Quin O 16- 26 Me CH (Me) CH (Me) H CH ₂ OEt 4-MeO-Ph O 16- 27 Me CH (Me) CH (Me) H CH ₂ OEt 4-EtO-Ph O 16- 28 Me CH (Me) CH (Me) H CH ₂ OEt 4-iPrO-Ph O 16- 29 Me CH ( Me) CH (Me) H CH ₂ OEt 4-MeS-Ph O 16-30 Me CH (Me) CH (Me) H CH ₂ OEt 4-EtS-Ph O 16- 31 Me CH (Me) CH (Me) H CH ₂ OEt 4-iPrS-Ph O 16- 32 Me CH (Me) CH (Me) H CH ₂ OEt 4-MeSO ₂ -Ph O 16-33 Me CH (Me) CH (Me) H CH ₂ OEt 4 -EtSO ₂ -Ph O 16- 34 Me CH (Me) CH (Me) H CH ₂ OEt 4-iPrSO ₂ -Ph O 16- 35 Me CH (Me) CH (Me) H CH ₂ OEt 4- (Pyr- 2) Ph O 16- 36 Me CH (Me) CH (Me) H CH ₂ OEt 4- (Pyr-3) Ph O 16- 37 Me CH (Me ) CH (Me) H CH ₂ OEt 4- (Pyr-3) Ph O 16- 38 Me CH (Me) CH (Me) H CH ₂ OEt 3-Ph-6-Pyr O ──────── ──────────────────────────.

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[Table 17] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 17- 1 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Et-Ph S 17- 2 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPr-Ph S 17- 3 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-Ph S 17- 4 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Ph-Ph S 17-5 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Pyr S 17-6 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Me-3 -Pyr S 17-7 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Et-3-Pyr S 17- 8 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-3-Pyr S 17-9 Me ( CH ₂ ) ₂ H CH ₂ OEt 6-Me-3-Pyr S 17-10 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Et-3-Pyr S 17-11 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Ph-3-Pyr S 17-12 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeO-3-Pyr S 17-13 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtO-3-Pyr S 17-14 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrO-3-Pyr S 17-15 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeS-3-Pyr S 17-16 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtS-3-Pyr S 17-17 Me (CH ₂ ) ₂ H C H ₂ OEt 6-iPrS-3-Pyr S 17-18 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeSO ₂ -3-Pyr S 17-19 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtSO ₂ -3-Pyr S 17-20 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrSO ₂ -3-Pyr S 17- 21 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Bz-3-Pyr S 17- _{22 Me (CH 2) 2 H} CH 2 OEt 6-PhO-3-Pyr S 17- 23 Me (CH 2) 2 H CH 2 OEt 6-PhS-3-Pyr S 17- 24 Me (CH 2) 2 H CH ₂ OEt 6-PhSO ₂ -3-Pyr S 17- 25 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Quin S 17- 26 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeO-Ph S 17- 27 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtO-Ph S 17- 28 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrO-Ph S 17- 29 Me (CH ₂ ) ₂ H CH ₂ OEt 4 -MeS-Ph S 17-30 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtS-Ph S 17- 31 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrS-Ph S 17- 32 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeSO ₂ -Ph S 17-33 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtSO ₂ -Ph S 17- 34 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph S 17- 35 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-2) Ph S 17- 36 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-3) Ph S 17- 37 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-3) Ph S 17- 38 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-6-Pyr S ────────── ─ ──────────────────────.

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[Table 18] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 18- 1 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Et-Ph NMe 18- 2 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPr-Ph NMe 18- 3 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-Ph NMe 18- 4 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Ph-Ph NMe 18-5 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Pyr NMe 18-6 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Me-3 -Pyr NMe 18- 7 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Et-3-Pyr NMe 18- 8 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-3-Pyr NMe 18- 9 Me ( CH ₂ ) ₂ H CH ₂ OEt 6-Me-3-Pyr NMe 18-10 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Et-3-Pyr NMe 18-11 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Ph-3-Pyr NMe 18-12 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeO-3-Pyr NMe 18-13 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtO-3-Pyr NMe 18-14 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrO-3-Pyr NMe 18-15 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeS-3-Pyr NMe 18-16 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtS-3 -Pyr NMe 18-17 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrS-3-Pyr NMe 18-18 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeSO ₂ -3-Pyr NMe 18-19 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtSO ₂ -3-Pyr NMe 18-20 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrSO ₂ -3-Pyr NMe 18- 21 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Bz-3-Pyr NMe 18-22 Me (CH ₂ ) ₂ H CH ₂ OEt 6-PhO-3-Pyr NMe 18-23 Me (CH ₂ ) ₂ H CH ₂ OEt 6-PhS-3 -Pyr NMe 18- 24 Me (CH ₂ ) ₂ H CH ₂ OEt 6-PhSO ₂ -3-Pyr NMe 18- 25 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Quin NMe 18- 26 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeO-Ph NMe 18- 27 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtO-Ph NMe 18- 28 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrO-Ph NMe 18 -29 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeS-Ph NMe 18-30 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtS-Ph NMe 18- 31 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrS-Ph NMe 18- 32 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeSO ₂ -Ph NMe 18-33 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtSO ₂ -Ph NMe 18- 34 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph NMe 18- 35 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-2) Ph NMe 18- 36 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-3) Ph NMe 18- 37 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-3) Ph NMe 18- 38 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-6-Pyr NMe ─────────────────────────────── ───.

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[Table 19] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 19- 1 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Et-Ph NAc 19- 2 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPr-Ph NAc 19- 3 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-Ph NAc 19- 4 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Ph-Ph NAc 19-5 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Pyr NAc 19-6 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Me-3 -Pyr NAc 19- 7 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Et-3-Pyr NAc 19- 8 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-3-Pyr NAc 19- 9 Me ( CH ₂ ) ₂ H CH ₂ OEt 6-Me-3-Pyr NAc 19-10 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Et-3-Pyr NAc 19-11 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Ph-3-Pyr NAc 19-12 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeO-3-Pyr NAc 19-13 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtO-3-Pyr NAc 19-14 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrO-3-Pyr NAc 19-15 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeS-3-Pyr NAc 19-16 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtS-3 -Pyr NAc 19-17 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrS-3-Pyr NAc 19-18 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeSO ₂ -3-Pyr NAc 19-19 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtSO ₂ -3-Pyr NAc 19-20 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrSO ₂ -3-Pyr NAc 19-21 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Bz-3-Pyr NAc 19-22 Me (CH ₂ ) ₂ H CH ₂ OEt 6-PhO-3-Pyr NAc 19-23 Me (CH ₂ ) ₂ H CH ₂ OEt 6-PhS-3 -Pyr NAc 19- 24 Me (CH ₂ ) ₂ H CH ₂ OEt 6-PhSO ₂ -3-Pyr NAc 19- 25 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Quin NAc 19- 26 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeO-Ph NAc 19- 27 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtO-Ph NAc 19- 28 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrO-Ph NAc 19 -29 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeS-Ph NAc 19-30 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtS-Ph NAc 19- 31 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrS-Ph NAc 19- 32 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeSO ₂ -Ph NAc 19- 33 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtSO ₂ -Ph NAc 19- 34 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph NAc 19- 35 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-2) Ph NAc 19- 36 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-3) Ph NAc 19- 37 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-3) Ph NAc 19- 38 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-6-Pyr NAc ─────────────────────────────── ───.

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[Table 20] ──────────────────────────────────── Examples R ¹ R ² R ³ Z W X Y compound number ──────────────────────────────────── 20- 1 Me (CH ₂ ) ₂ 2- Cl CH ₂ OEt 4-Et-Ph O 20- 2 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4-iPr-Ph O 20- 3 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 3-Ph- Ph O 20- 4 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4-Ph-Ph O 20- 5 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 3-Pyr O 20- 6 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 5-Me-3-Pyr O 20- 7 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 5-Et-3-Pyr O 20- 8 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 5-Ph-3-Pyr O 20- 9 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6-Me-3-Pyr O 20- 10 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6 -Et-3-Pyr O 20- 11 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6-Ph-3-Pyr O 20- 12 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6-MeO-3 -Pyr O 20- 13 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6-EtO-3-Pyr O 20-14 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6-iPrO-3-Pyr O 20 _{- 15 Me (CH 2) 2} 2-Cl CH 2 OEt 6-MeS-3-Pyr O 20- 16 Me (CH 2) 2 2-C l CH ₂ OEt 6-EtS-3-Pyr O 20-17 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6-iPrS-3-Pyr O 20-18 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6-MeSO ₂ -3-Pyr O 20- 19 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6-EtSO ₂ -3-Pyr O 20- 20 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6- _{iPrSO 2 -3-Pyr O 20- 21} Me (CH 2) 2 2-Cl CH 2 OEt 6-Bz-3-Pyr O 20- 22 Me (CH 2) 2 2-Cl CH 2 OEt 6-PhO-3 -Pyr O 20- 23 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6-PhS-3-Pyr O 20- 24 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 6-PhSO ₂ -3-Pyr O 20- 25 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 2-Quin O 20- 26 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4-MeO-Ph O 20- 27 Me (CH ₂ ) ₂ 2 -Cl CH ₂ OEt 4-EtO-Ph O 20- 28 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4-iPrO-Ph O 20- 29 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4-MeS -Ph O 20- 30 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4-EtS-Ph O 20- 31 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4-iPrS-Ph O 20- 32 Me ( CH ₂ ) ₂ 2-Cl CH ₂ OEt 4-MeSO ₂ -Ph O 20- 33 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4-EtSO ₂ -Ph O 20- 34 Me (CH ₂ ) ₂ 2- Cl CH ₂ OEt 4-iPrSO ₂ -Ph O 20- 35 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4- (Pyr-2) Ph O 20- 36 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4- (Pyr-3) Ph O 20- 37 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 4- (Pyr-3) Ph O 20- 38 Me (CH ₂ ) ₂ 2-Cl CH ₂ OEt 3-Ph-6-Pyr O ────────── ────────────────────────.

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[Table 21] Example R ¹ R ² R ³ ZW X Y compound No. _{──────────────────────────────────── 21- 1 Me (CH 2)} 2 3- Cl CH ₂ OEt 4-Et-Ph O 21- 2 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 4-iPr-Ph O 21- 3 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 3-Ph- Ph O 21- 4 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 4-Ph-Ph O 21- 5 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 3-Pyr O 21- 6 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 5-Me-3-Pyr O 21- 7 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 5-Et-3-Pyr O 21- 8 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 5-Ph-3-Pyr O 21-9 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 6-Me-3-Pyr O 21-10 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 6 -Et-3-Pyr O 21- 11 Me (CH 2) 2 3-Cl CH 2 OEt 6-Ph-3-Pyr O 21- 12 Me (CH 2) 2 3-Cl CH 2 OEt 6-MeO-3 _{-Pyr O 21- 13 Me (CH 2} ) 2 3-Cl CH 2 OEt 6-EtO-3-Pyr O 21- 14 Me (CH 2) 2 3-Cl CH 2 OEt 6-iPrO-3-Pyr O 21 _{- 15 Me (CH 2) 2} 3-Cl CH 2 OEt 6-MeS-3-Pyr O 21- 16 Me (CH 2) 2 3-C _{l CH 2 OEt 6-EtS-} 3-Pyr O 21- 17 Me (CH 2) 2 3-Cl CH 2 OEt 6-iPrS-3-Pyr O 21- 18 Me (CH 2) 2 3-Cl CH 2 OEt _{6-MeSO 2 -3-Pyr O} 21- 19 Me (CH 2) 2 3-Cl CH 2 OEt 6-EtSO 2 -3-Pyr O 21- 20 Me (CH 2) 2 3-Cl CH 2 OEt 6- _{iPrSO 2 -3-Pyr O 21- 21} Me (CH 2) 2 3-Cl CH 2 OEt 6-Bz-3-Pyr O 21- 22 Me (CH 2) 2 3-Cl CH 2 OEt 6-PhO-3 _{-Pyr O 21- 23 Me (CH 2} ) 2 3-Cl CH 2 OEt 6-PhS-3-Pyr O 21- 24 Me (CH 2) 2 3-Cl CH 2 OEt 6-PhSO 2 -3-Pyr O 21- 25 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 2-Quin O 21- 26 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 4-MeO-Ph O 21- 27 Me (CH ₂ ) ₂ 3 -Cl CH ₂ OEt 4-EtO-Ph O 21- 28 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 4-iPrO-Ph O 21- 29 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 4-MeS _{-Ph O 21- 30 Me (CH 2} ) 2 3-Cl CH 2 OEt 4-EtS-Ph O 21- 31 Me (CH 2) 2 3-Cl CH 2 OEt 4-iPrS-Ph O 21- 32 Me ( _{CH 2) 2 3-Cl CH} 2 OEt 4-MeSO 2 -Ph O 21- 33 Me (CH 2) 2 3-Cl CH 2 OEt 4-EtSO 2 -Ph O 21- 34 Me (CH 2) 2 3- Cl CH ₂ OEt 4-iPrSO ₂ -Ph O 21- 35 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 4- (Pyr-2) Ph O 21- 36 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 4- (Pyr-3) Ph O 21- 37 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 4- (Pyr-3) Ph O 21- 38 Me (CH ₂ ) ₂ 3-Cl CH ₂ OEt 3-Ph-6-Pyr O ────────── ────────────────────────.

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[Table 22] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 22- 1 Me (CH ₂ ) ₂ 2- MeO CH ₂ OEt 4-Et-Ph O 22- 2 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 4-iPr-Ph O 22- 3 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 3-Ph- _{Ph O 22- 4 Me (CH 2} ) 2 2-MeO CH 2 OEt 4-Ph-Ph O 22- 5 Me (CH 2) 2 2-MeO CH 2 OEt 3-Pyr O 22- 6 Me (CH 2) ₂ 2-MeO CH ₂ OEt 5-Me-3-Pyr O 22- 7 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 5-Et-3-Pyr O 22- 8 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 5-Ph-3-Pyr O 22-9 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 6-Me-3-Pyr O 22-10 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 6 -Et-3-Pyr O 22- 11 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 6-Ph-3-Pyr O 22-12 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 6-MeO-3 -Pyr O 22- 13 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 6-EtO-3-Pyr O 22-14 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 6-iPrO-3-Pyr O 22 -15 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 6-MeS-3-Pyr O 22-16 M _{e (CH 2) 2 2-} MeO CH 2 OEt 6-EtS-3-Pyr O 22- 17 Me (CH 2) 2 2-MeO CH 2 OEt 6-iPrS-3-Pyr O 22- 18 Me (CH 2 ) ₂ 2-MeO CH ₂ OEt 6-MeSO ₂ -3-Pyr O 22-19 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 6-EtSO ₂ -3-Pyr O 22-20 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 6-iPrSO ₂ -3-Pyr O 22- 21 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 6-Bz-3-Pyr O 22- 22 Me (CH ₂ ) ₂ 2-MeO _{CH 2 OEt 6-PhO-3} -Pyr O 22- 23 Me (CH 2) 2 2-MeO CH 2 OEt 6-PhS-3-Pyr O 22- 24 Me (CH 2) 2 2-MeO CH 2 OEt 6 -PhSO ₂ -3-Pyr O 22- 25 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 2-Quin O 22- 26 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 4-MeO-Ph O 22- 27 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 4-EtO-Ph O 22- 28 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 4-iPrO-Ph O 22- 29 Me (CH ₂ ) ₂ 2 -MeO CH ₂ OEt 4-MeS-Ph O 22-30 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 4-EtS-Ph O 22- 31 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 4-iPrS -Ph O 22- 32 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 4-MeSO ₂ -Ph O 22- 33 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 4-EtSO ₂ -Ph O 22- 34 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 4-iPrSO ₂ -Ph O 22- 35 Me (CH ₂ ) ₂ 2-MeO CH ₂ OEt 4- (Pyr-2) Ph O 22- 36 Me (CH ₂ ) ₂ 2-MeO CH _{2 OEt 4- (Pyr-3)} Ph O 22- 37 Me (CH 2) 2 2-MeO CH 2 OEt 4- (Pyr-4) Ph O 22- 38 Me (CH 2) 2 2-MeO CH 2 OEt 3-Ph-6-Pyr O ──────────────────────────────────.

[0153]

[Table 23] Example R ¹ R ² R ³ ZW X Y compound No. _{──────────────────────────────────── 23- 1 Me (CH 2)} 2 3- MeO CH ₂ OEt 4-Et-Ph O 23- 2 Me (CH ₂ ) ₂ 3-MeO CH ₂ OEt 4-iPr-Ph O 23- 3 Me (CH ₂ ) ₂ 3-MeO CH ₂ OEt 3-Ph- _{Ph O 23- 4 Me (CH 2} ) 2 3-MeO CH 2 OEt 4-Ph-Ph O 23- 5 Me (CH 2) 2 3-MeO CH 2 OEt 3-Pyr O 23- 6 Me (CH 2) _{2 3-MeO CH 2 OEt 5} -Me-3-Pyr O 23- 7 Me (CH 2) 2 3-MeO CH 2 OEt 5-Et-3-Pyr O 23- 8 Me (CH 2) 2 3-MeO _{CH 2 OEt 5-Ph-3} -Pyr O 23- 9 Me (CH 2) 2 3-MeO CH 2 OEt 6-Me-3-Pyr O 23- 10 Me (CH 2) 2 3-MeO CH 2 OEt 6 -Et-3-Pyr O 23- 11 Me (CH 2) 2 3-MeO CH 2 OEt 6-Ph-3-Pyr O 23- 12 Me (CH 2) 2 3-MeO CH 2 OEt 6-MeO-3 _{-Pyr O 23- 13 Me (CH 2} ) 2 3-MeO CH 2 OEt 6-EtO-3-Pyr O 23- 14 Me (CH 2) 2 3-MeO CH 2 OEt 6-iPrO-3-Pyr O 23 -15 Me (CH ₂ ) ₂ 3-MeO CH ₂ OEt 6-MeS-3-Pyr O 23-16 M _{e (CH 2) 2 3-} MeO CH 2 OEt 6-EtS-3-Pyr O 23- 17 Me (CH 2) 2 3-MeO CH 2 OEt 6-iPrS-3-Pyr O 23- 18 Me (CH 2 ) ₂ 3-MeO CH ₂ OEt 6-MeSO ₂ -3-Pyr O 23-19 Me (CH ₂ ) ₂ 3-MeO CH ₂ OEt 6-EtSO ₂ -3-Pyr O 23-20 Me (CH ₂ ) ₂ 3-MeO CH ₂ OEt 6-iPrSO ₂ -3-Pyr O 23- 21 Me (CH ₂ ) ₂ 3-MeO CH ₂ OEt 6-Bz-3-Pyr O 23- 22 Me (CH ₂ ) ₂ 3-MeO _{CH 2 OEt 6-PhO-3} -Pyr O 23- 23 Me (CH 2) 2 3-MeO CH 2 OEt 6-PhS-3-Pyr O 23- 24 Me (CH 2) 2 3-MeO CH 2 OEt 6 _{-PhSO 2 -3-Pyr O 23- 25} Me (CH 2) 2 3-MeO CH 2 OEt 2-Quin O 23- 26 Me (CH 2) 2 3-MeO CH 2 OEt 4-MeO-Ph O 23- _{27 Me (CH 2) 2 3} -MeO CH 2 OEt 4-EtO-Ph O 23- 28 Me (CH 2) 2 3-MeO CH 2 OEt 4-iPrO-Ph O 23- 29 Me (CH 2) 2 3 _{-MeO CH 2 OEt 4-MeS-} Ph O 23- 30 Me (CH 2) 2 3-MeO CH 2 OEt 4-EtS-Ph O 23- 31 Me (CH 2) 2 3-MeO CH 2 OEt 4-iPrS -Ph O 23- 32 Me (CH ₂ ) ₂ 3-MeO CH ₂ OEt 4-MeSO ₂ -Ph O 23- 33 Me (CH ₂ ) ₂ 3-MeO CH ₂ OEt 4-EtSO ₂ -Ph O 23- 34 _{Me (CH 2) 2 3-} MeO CH 2 OEt 4-iPrSO 2 -Ph O 23- 35 Me (CH 2) 2 3-MeO CH 2 OEt 4- (Pyr-2) Ph O 23- 36 Me (CH 2 ) ₂ 3-MeO CH ₂ OEt 4- (Pyr-3) Ph O 23- 37 Me (CH ₂ ) ₂ 3-MeO CH ₂ OEt 4- (Pyr-4) Ph O 23- 38 Me (CH ₂ ) ₂ 3-MeO CH ₂ OEt 3-Ph-6-Pyr O ──────────────────────────────────.

[0154]

[Table 24] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 24- 1 Me (CH ₂ ) ₂ H CH ₂ OPr 4-Et-Ph O 24- 2 Me (CH ₂ ) ₂ H CH ₂ OPr 4-iPr-Ph O 24- 3 Me (CH ₂ ) ₂ H CH ₂ OPr 3-Ph-Ph O 24- 4 Me (CH ₂ ) ₂ H CH ₂ OPr 4-Ph-Ph O 24- 5 Me (CH ₂ ) ₂ H CH ₂ OPr 3-Pyr O 24- 6 Me (CH ₂ ) ₂ H CH ₂ OPr 5-Me-3 -Pyr O 24- 7 Me (CH ₂ ) ₂ H CH ₂ OPr 5-Et-3-Pyr O 24- 8 Me (CH ₂ ) ₂ H CH ₂ OPr 5-Ph-3-Pyr O 24- 9 Me ( CH ₂ ) ₂ H CH ₂ OPr 6-Me-3-Pyr O 24- 10 Me (CH ₂ ) ₂ H CH ₂ OPr 6-Et-3-Pyr O 24- 11 Me (CH ₂ ) ₂ H CH ₂ OPr 6-Ph-3-Pyr O 24- 12 Me (CH ₂ ) ₂ H CH ₂ OPr 6-MeO-3-Pyr O 24- 13 Me (CH ₂ ) ₂ H CH ₂ OPr 6-EtO-3-Pyr O 24- 14 Me (CH ₂ ) ₂ H CH ₂ OPr 6-iPrO-3-Pyr O 24- 15 Me (CH ₂ ) ₂ H CH ₂ OPr 6-MeS-3-Pyr O 24- 16 Me (CH ₂ ) ₂ H CH ₂ OPr 6-EtS-3-Pyr O 24- 17 Me (CH ₂ ) ₂ H C H ₂ OPr 6-iPrS-3-Pyr O 24- 18 Me (CH ₂ ) ₂ H CH ₂ OPr 6-MeSO ₂ -3-Pyr O 24-19 Me (CH ₂ ) ₂ H CH ₂ OPr 6-EtSO ₂ -3-Pyr O 24- 20 Me (CH ₂ ) ₂ H CH ₂ OPr 6-iPrSO ₂ -3-Pyr O 24- 21 Me (CH ₂ ) ₂ H CH ₂ OPr 6-Bz-3-Pyr O 24- 22 Me (CH ₂ ) ₂ H CH ₂ OPr 6-PhO-3-Pyr O 24- 23 Me (CH ₂ ) ₂ H CH ₂ OPr 6-PhS-3-Pyr O 24- 24 Me (CH ₂ ) ₂ H CH ₂ OPr 6-PhSO ₂ -3-Pyr O 24-25 Me (CH ₂ ) ₂ H CH ₂ OPr 2-Quin O 24-26 Me (CH ₂ ) ₂ H CH ₂ OPr 4-MeO-Ph O 24- 27 Me (CH ₂ ) ₂ H CH ₂ OPr 4-EtO-Ph O 24-28 Me (CH ₂ ) ₂ H CH ₂ OPr 4-iPrO-Ph O 24-29 Me (CH ₂ ) ₂ H CH ₂ OPr 4 -MeS-Ph O 24-30 Me (CH ₂ ) ₂ H CH ₂ OPr 4-EtS-Ph O 24-31 Me (CH ₂ ) ₂ H CH ₂ OPr 4-iPrS-Ph O 24-32 Me (CH ₂ ) ₂ H CH ₂ OPr 4-MeSO ₂ -Ph O 24-33 Me (CH ₂ ) ₂ H CH ₂ OPr 4-EtSO ₂ -Ph O 24-34 Me (CH ₂ ) ₂ H CH ₂ OPr 4-iPrSO ₂ -Ph O 24-35 Me (CH ₂ ) ₂ H CH ₂ OPr 4- (Pyr-2) Ph O 24-36 Me (CH ₂ ) ₂ H CH ₂ OPr 4- (Pyr-3) Ph O 24-37 Me (CH ₂ ) ₂ H CH ₂ OPr 4- (Pyr-4) Ph O 24-38 Me (CH ₂ ) ₂ H CH ₂ OPr 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0155]

[Table 25] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 25- 1 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-Et-Ph O 25- 2 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-iPr-Ph O 25- 3 Me (CH ₂ ) ₂ H CH ₂ OiPr 3-Ph-Ph O 25- 4 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-Ph-Ph O 25-5 Me (CH ₂ ) ₂ H CH ₂ OiPr 3-Pyr O 25-6 Me (CH ₂ ) ₂ H CH ₂ OiPr 5-Me-3 -Pyr O 25- 7 Me (CH ₂ ) ₂ H CH ₂ OiPr 5-Et-3-Pyr O 25- 8 Me (CH ₂ ) ₂ H CH ₂ OiPr 5-Ph-3-Pyr O 25- 9 Me ( CH ₂ ) ₂ H CH ₂ OiPr 6-Me-3-Pyr O 25- 10 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-Et-3-Pyr O 25- 11 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-Ph-3-Pyr O 25-12 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-MeO-3-Pyr O 25- 13 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-EtO-3-Pyr O 25-14 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-iPrO-3-Pyr O 25- 15 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-MeS-3-Pyr O 25- 16 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-EtS-3-Pyr O 25-17 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-iPrS-3-Pyr O 25-18 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-MeSO ₂ -3-Pyr O 25-19 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-EtSO ₂ -3-Pyr O 25-20 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-iPrSO ₂ -3-Pyr O 25- 21 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-Bz -3-Pyr O 25- 22 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-PhO-3-Pyr O 25- 23 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-PhS-3-Pyr O 25- 24 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-PhSO ₂ -3-Pyr O 25-25 Me (CH ₂ ) ₂ H CH ₂ OiPr 2-Quin O 25-26 Me (CH ₂ ) ₂ H CH ₂ OiPr 4 -MeO-Ph O 25- 27 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-EtO-Ph O 25- 28 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-iPrO-PhO 25- 29 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-MeS-Ph O 25-30 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-EtS-Ph O 25- 31 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-iPrS-Ph O 25- 32 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-MeSO ₂ -Ph O 25- 33 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-EtSO ₂ -Ph O 25- 34 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-iPrSO ₂ -Ph O 25- 35 Me (CH ₂ ) ₂ H CH ₂ OiPr 4- (Pyr-2) Ph O 25- 36 Me (CH ₂ ) ₂ H CH ₂ OiPr 4- (Pyr- 3) Ph O 25- 37 Me (CH ₂ ) ₂ H CH ₂ OiPr 4- (Pyr-4) Ph O 25- 38 Me (CH ₂ ) ₂ H CH ₂ OiPr 3-Ph-6-Py r O ──────────────────────────────────.

[0156]

[Table 26] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 26- 1 Me (CH ₂ ) ₂ H CH ₂ SMe 4-Et-Ph O 26- 2 Me (CH ₂ ) ₂ H CH ₂ SMe 4-iPr-Ph O 26- 3 Me (CH ₂ ) ₂ H CH ₂ SMe 3-Ph-Ph O 26- 4 Me (CH ₂ ) ₂ H CH ₂ SMe 4-Ph-Ph O 26-5 Me (CH ₂ ) ₂ H CH ₂ SMe 3-Pyr O 26-6 6 Me (CH ₂ ) ₂ H CH ₂ SMe 5-Me-3 -Pyr O 26- 7 Me (CH ₂ ) ₂ H CH ₂ SMe 5-Et-3-Pyr O 26- 8 Me (CH ₂ ) ₂ H CH ₂ SMe 5-Ph-3-Pyr O 26- 9 Me ( CH ₂ ) ₂ H CH ₂ SMe 6-Me-3-Pyr O 26-10 Me (CH ₂ ) ₂ H CH ₂ SMe 6-Et-3-Pyr O 26- 11 Me (CH ₂ ) ₂ H CH ₂ SMe 6-Ph-3-Pyr O 26- 12 Me (CH ₂ ) ₂ H CH ₂ SMe 6-MeO-3-Pyr O 26- 13 Me (CH ₂ ) ₂ H CH ₂ SMe 6-EtO-3-Pyr O 26- 14 Me (CH ₂ ) ₂ H CH ₂ SMe 6-iPrO-3-Pyr O 26-15 Me (CH ₂ ) ₂ H CH ₂ SMe 6-MeS-3-Pyr O 26-16 Me (CH ₂ ) ₂ H CH ₂ SMe 6-EtS-3-Pyr O 26-17 Me (CH ₂ ) ₂ H C H ₂ SMe 6-iPrS-3-Pyr O 26-18 Me (CH ₂ ) ₂ H CH ₂ SMe 6-MeSO ₂ -3-Pyr O 26-19 Me (CH ₂ ) ₂ H CH ₂ SMe 6-EtSO ₂ -3-Pyr O 26- 20 Me (CH ₂ ) ₂ H CH ₂ SMe 6-iPrSO ₂ -3-Pyr O 26- 21 Me (CH ₂ ) ₂ H CH ₂ SMe 6-Bz-3-Pyr O 26- _{22 Me (CH 2) 2 H} CH 2 SMe 6-PhO-3-Pyr O 26- 23 Me (CH 2) 2 H CH 2 SMe 6-PhS-3-Pyr O 26- 24 Me (CH 2) 2 H CH ₂ SMe 6-PhSO ₂ -3-Pyr O 26- 25 Me (CH ₂ ) ₂ H CH ₂ SMe 2-Quin O 26- 26 Me (CH ₂ ) ₂ H CH ₂ SMe 4-MeO-Ph O 26- 27 Me (CH ₂ ) ₂ H CH ₂ SMe 4-EtO-Ph O 26- 28 Me (CH ₂ ) ₂ H CH ₂ SMe 4-iPrO-Ph O 26- 29 Me (CH ₂ ) ₂ H CH ₂ SMe 4 -MeS-Ph O 26- 30 Me (CH ₂ ) ₂ H CH ₂ SMe 4-EtS-Ph O 26- 31 Me (CH ₂ ) ₂ H CH ₂ SMe 4-iPrS-Ph O 26- 32 Me (CH ₂ ) ₂ H CH ₂ SMe 4-MeSO ₂ -Ph O 26-33 Me (CH ₂ ) ₂ H CH ₂ SMe 4-EtSO ₂ -Ph O 26- 34 Me (CH ₂ ) ₂ H CH ₂ SMe 4-iPrSO ₂ -Ph O 26- 35 Me (CH ₂ ) ₂ H CH ₂ SMe 4- (Pyr-2) Ph O 26- 36 Me (CH ₂ ) ₂ H CH ₂ SMe 4- (Pyr-3) Ph O 26- 37 Me (CH ₂ ) ₂ H CH ₂ SMe 4- (Pyr-4) Ph O 26- 38 Me (CH ₂ ) ₂ H CH ₂ SMe 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0157]

[Table 27] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 27- 1 Me (CH ₂ ) ₂ H CH ₂ SEt 4-Et-Ph O 27- 2 Me (CH ₂ ) ₂ H CH ₂ SEt 4-iPr-Ph O 27- 3 Me (CH ₂ ) ₂ H CH ₂ SEt 3-Ph-Ph O 27- 4 Me (CH ₂ ) ₂ H CH ₂ SEt 4-Ph-Ph O 27- 5 Me (CH ₂ ) ₂ H CH ₂ SEt 3-Pyr O 27- 6 Me (CH ₂ ) ₂ H CH ₂ SEt 5-Me-3 -Pyr O 27- 7 Me (CH ₂ ) ₂ H CH ₂ SEt 5-Et-3-Pyr O 27- 8 Me (CH ₂ ) ₂ H CH ₂ SEt 5-Ph-3-Pyr O 27- 9 Me ( CH ₂ ) ₂ H CH ₂ SEt 6-Me-3-Pyr O 27-10 Me (CH ₂ ) ₂ H CH ₂ SEt 6-Et-3-Pyr O 27-11 Me (CH ₂ ) ₂ H CH ₂ SEt 6-Ph-3-Pyr O 27- 12 Me (CH ₂ ) ₂ H CH ₂ SEt 6-MeO-3-Pyr O 27- 13 Me (CH ₂ ) ₂ H CH ₂ SEt 6-EtO-3-Pyr O 27- 14 Me (CH ₂ ) ₂ H CH ₂ SEt 6-iPrO-3-Pyr O 27- 15 Me (CH ₂ ) ₂ H CH ₂ SEt 6-MeS-3-Pyr O 27- 16 Me (CH ₂ ) ₂ H CH ₂ SEt 6-EtS-3-Pyr O 27-17 Me (CH ₂ ) ₂ H C H ₂ SEt 6-iPrS-3-Pyr O 27-18 Me (CH ₂ ) ₂ H CH ₂ SEt 6-MeSO ₂ -3-Pyr O 27-19 Me (CH ₂ ) ₂ H CH ₂ SEt 6-EtSO ₂ -3-Pyr O 27- 20 Me (CH ₂ ) ₂ H CH ₂ SEt 6-iPrSO ₂ -3-Pyr O 27- 21 Me (CH ₂ ) ₂ H CH ₂ SEt 6-Bz-3-Pyr O 27- _{22 Me (CH 2) 2 H} CH 2 SEt 6-PhO-3-Pyr O 27- 23 Me (CH 2) 2 H CH 2 SEt 6-PhS-3-Pyr O 27- 24 Me (CH 2) 2 H CH ₂ SEt 6-PhSO ₂ -3-Pyr O 27- 25 Me (CH ₂ ) ₂ H CH ₂ SEt 2-Quin O 27- 26 Me (CH ₂ ) ₂ H CH ₂ SEt 4-MeO-Ph O 27- 27 Me (CH ₂ ) ₂ H CH ₂ SEt 4-EtO-Ph O 27- 28 Me (CH ₂ ) ₂ H CH ₂ SEt 4-iPrO-Ph O 27- 29 Me (CH ₂ ) ₂ H CH ₂ SEt 4 -MeS-Ph O 27- 30 Me (CH ₂ ) ₂ H CH ₂ SEt 4-EtS-Ph O 27- 31 Me (CH ₂ ) ₂ H CH ₂ SEt 4-iPrS-Ph O 27- 32 Me (CH ₂ ) ₂ H CH ₂ SEt 4-MeSO ₂ -Ph O 27- 33 Me (CH ₂ ) ₂ H CH ₂ SEt 4-EtSO ₂ -Ph O 27- 34 Me (CH ₂ ) ₂ H CH ₂ SEt 4-iPrSO ₂ -Ph O 27- 35 Me (CH ₂ ) ₂ H CH ₂ SEt 4- (Pyr-2) Ph O 27- 36 Me (CH ₂ ) ₂ H CH ₂ SEt 4- (Pyr-3) Ph O 27- 37 Me (CH ₂ ) ₂ H CH ₂ SEt 4- (Pyr-4) Ph O 27- 38 Me (CH ₂ ) ₂ H CH ₂ SEt 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0158]

[Table 28] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 28- 1 Me (CH ₂ ) ₂ H CH ₂ SPr 4-Et-Ph O 28- 2 Me (CH ₂ ) ₂ H CH ₂ SPr 4-iPr-Ph O 28- 3 Me (CH ₂ ) ₂ H CH ₂ SPr 3-Ph-Ph O 28- 4 Me (CH ₂ ) ₂ H CH ₂ SPr 4-Ph-Ph O 28-5 Me (CH ₂ ) ₂ H CH ₂ SPr 3-Pyr O 28-6 6 Me (CH ₂ ) ₂ H CH ₂ SPr 5-Me-3 -Pyr O 28- 7 Me (CH ₂ ) ₂ H CH ₂ SPr 5-Et-3-Pyr O 28- 8 Me (CH ₂ ) ₂ H CH ₂ SPr 5-Ph-3-Pyr O 28- 9 Me ( CH ₂ ) ₂ H CH ₂ SPr 6-Me-3-Pyr O 28-10 Me (CH ₂ ) ₂ H CH ₂ SPr 6-Et-3-Pyr O 28-11 Me (CH ₂ ) ₂ H CH ₂ SPr 6-Ph-3-Pyr O 28-12 Me (CH ₂ ) ₂ H CH ₂ SPr 6-MeO-3-Pyr O 28- 13 Me (CH ₂ ) ₂ H CH ₂ SPr 6-EtO-3-Pyr O 28- 14 Me (CH ₂ ) ₂ H CH ₂ SPr 6-iPrO-3-Pyr O 28-15 Me (CH ₂ ) ₂ H CH ₂ SPr 6-MeS-3-Pyr O 28-16 Me (CH ₂ ) ₂ H CH ₂ SPr 6-EtS-3-Pyr O 28-17 Me (CH ₂ ) ₂ H C H ₂ SPr 6-iPrS-3-Pyr O 28-18 Me (CH ₂ ) ₂ H CH ₂ SPr 6-MeSO ₂ -3-Pyr O 28-19 Me (CH ₂ ) ₂ H CH ₂ SPr 6-EtSO ₂ -3-Pyr O 28- 20 Me (CH ₂ ) ₂ H CH ₂ SPr 6-iPrSO ₂ -3-Pyr O 28- 21 Me (CH ₂ ) ₂ H CH ₂ SPr 6-Bz-3-Pyr O 28- _{22 Me (CH 2) 2 H} CH 2 SPr 6-PhO-3-Pyr O 28- 23 Me (CH 2) 2 H CH 2 SPr 6-PhS-3-Pyr O 28- 24 Me (CH 2) 2 H CH ₂ SPr 6-PhSO ₂ -3-Pyr O 28- 25 Me (CH ₂ ) ₂ H CH ₂ SPr 2-Quin O 28- 26 Me (CH ₂ ) ₂ H CH ₂ SPr 4-MeO-Ph O 28- 27 Me (CH ₂ ) ₂ H CH ₂ SPr 4-EtO-Ph O 28-28 Me (CH ₂ ) ₂ H CH ₂ SPr 4-iPrO-Ph O 28-29 Me (CH ₂ ) ₂ H CH ₂ SPr 4 -MeS-Ph O 28-30 Me (CH ₂ ) ₂ H CH ₂ SPr 4-EtS-Ph O 28-31 Me (CH ₂ ) ₂ H CH ₂ SPr 4-iPrS-Ph O 28-32 Me (CH ₂ ) ₂ H CH ₂ SPr 4-MeSO ₂ -Ph O 28- 33 Me (CH ₂ ) ₂ H CH ₂ SPr 4-EtSO ₂ -Ph O 28- 34 Me (CH ₂ ) ₂ H CH ₂ SPr 4-iPrSO ₂ -Ph O 28- 35 Me (CH ₂ ) ₂ H CH ₂ SPr 4- (Pyr-2) Ph O 28- 36 Me (CH ₂ ) ₂ H CH ₂ SPr 4- (Pyr-3) Ph O 28- 37 Me (CH ₂ ) ₂ H CH ₂ SPr 4- (Pyr-4) Ph O 28- 38 Me (CH ₂ ) ₂ H CH ₂ SPr 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0159]

[Table 29] Example R ¹ R ² R ³ Z W X Y compound number ──────────────────────────────────── 29- 1 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-Et-Ph O 29- 2 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-iPr-Ph O 29- 3 Me (CH ₂ ) ₂ H CH ₂ SiPr 3-Ph-Ph O 29- 4 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-Ph-Ph O 29- 5 Me (CH ₂ ) ₂ H CH ₂ SiPr 3-Pyr O 29- 6 Me (CH ₂ ) ₂ H CH ₂ SiPr 5-Me-3 -Pyr O 29- 7 Me (CH ₂ ) ₂ H CH ₂ SiPr 5-Et-3-Pyr O 29- 8 Me (CH ₂ ) ₂ H CH ₂ SiPr 5-Ph-3-Pyr O 29- 9 Me ( CH ₂ ) ₂ H CH ₂ SiPr 6-Me-3-Pyr O 29-10 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-Et-3-Pyr O 29-11 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-Ph-3-Pyr O 29-12 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-MeO-3-Pyr O 29- 13 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-EtO-3-Pyr O 29- 14 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-iPrO-3-Pyr O 29-15 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-MeS-3-Pyr O 29-16 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-EtS-3-Pyr O 29-17 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-iPrS-3-Pyr O 29-18 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-MeSO ₂ -3-Pyr O 29-19 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-EtSO ₂ -3-Pyr O 29-20 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-iPrSO ₂ -3-Pyr O 29- 21 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-Bz -3-Pyr O 29- 22 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-PhO-3-Pyr O 29- 23 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-PhS-3-Pyr O 29- 24 Me (CH ₂ ) ₂ H CH ₂ SiPr 6-PhSO ₂ -3-Pyr O 29-25 Me (CH ₂ ) ₂ H CH ₂ SiPr 2-Quin O 29-26 Me (CH ₂ ) ₂ H CH ₂ SiPr 4 -MeO-Ph O 29- 27 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-EtO-Ph O 29- 28 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-iPrO-Ph O 29- 29 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-MeS-Ph O 29-30 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-EtS-Ph O 29- 31 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-iPrS-Ph O 29- 32 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-MeSO ₂ -Ph O 29- 33 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-EtSO ₂ -Ph O 29- 34 Me (CH ₂ ) ₂ H CH ₂ SiPr 4-iPrSO ₂ -Ph O 29- 35 Me (CH ₂ ) ₂ H CH ₂ SiPr 4- (Pyr-2) Ph O 29- 36 Me (CH ₂ ) ₂ H CH ₂ SiPr 4- (Pyr- 3) Ph O 29- 37 Me (CH ₂ ) ₂ H CH ₂ SiPr 4- (Pyr-4) Ph O 29- 38 Me (CH ₂ ) ₂ H CH ₂ SiPr 3-Ph-6-Py r O ──────────────────────────────────.

[0160]

[Table 30] 例 示 Examples R ¹ R ² R ³ Z W X Y compound number ──────────────────────────────────── 30- 1 Me (CH ₂ ) ₂ H CH ₂ OPh 4-Et-Ph O 30- 2 Me (CH ₂ ) ₂ H CH ₂ OPh 4-iPr-Ph O 30- 3 Me (CH ₂ ) ₂ H CH ₂ OPh 3-Ph-Ph O 30- 4 Me (CH ₂ ) ₂ H CH ₂ OPh 4-Ph-Ph O 30-5 Me (CH ₂ ) ₂ H CH ₂ OPh 3-Pyr O 30-6 Me (CH ₂ ) ₂ H CH ₂ OPh 5-Me-3 -Pyr O 30- 7 Me (CH ₂ ) ₂ H CH ₂ OPh 5-Et-3-Pyr O 30- 8 Me (CH ₂ ) ₂ H CH ₂ OPh 5-Ph-3-Pyr O 30- 9 Me ( CH ₂ ) ₂ H CH ₂ OPh 6-Me-3-Pyr O 30-10 Me (CH ₂ ) ₂ H CH ₂ OPh 6-Et-3-Pyr O 30-11 Me (CH ₂ ) ₂ H CH ₂ OPh 6-Ph-3-Pyr O 30-12 Me (CH ₂ ) ₂ H CH ₂ OPh 6-MeO-3-Pyr O 30- 13 Me (CH ₂ ) ₂ H CH ₂ OPh 6-EtO-3-Pyr O 30-14 Me (CH ₂ ) ₂ H CH ₂ OPh 6-iPrO-3-Pyr O 30-15 Me (CH ₂ ) ₂ H CH ₂ OPh 6-MeS-3-Pyr O 30-16 Me (CH ₂ ) ₂ H CH ₂ OPh 6-EtS-3-Pyr O 30-17 Me (CH ₂ ) ₂ H C H ₂ OPh 6-iPrS-3-Pyr O 30-18 Me (CH ₂ ) ₂ H CH ₂ OPh 6-MeSO ₂ -3-Pyr O 30-19 Me (CH ₂ ) ₂ H CH ₂ OPh 6-EtSO ₂ -3-Pyr O 30- 20 Me (CH ₂ ) ₂ H CH ₂ OPh 6-iPrSO ₂ -3-Pyr O 30- 21 Me (CH ₂ ) ₂ H CH ₂ OPh 6-Bz-3-Pyr O 30- _{22 Me (CH 2) 2 H} CH 2 OPh 6-PhO-3-Pyr O 30- 23 Me (CH 2) 2 H CH 2 OPh 6-PhS-3-Pyr O 30- 24 Me (CH 2) 2 H CH ₂ OPh 6-PhSO ₂ -3-Pyr O 30- 25 Me (CH ₂ ) ₂ H CH ₂ OPh 2-Quin O 30- 26 Me (CH ₂ ) ₂ H CH ₂ OPh 4-MeO-Ph O 30- 27 Me (CH ₂ ) ₂ H CH ₂ OPh 4-EtO-Ph O 30-28 Me (CH ₂ ) ₂ H CH ₂ OPh 4-iPrO-Ph O 30-29 Me (CH ₂ ) ₂ H CH ₂ OPh 4 -MeS-Ph O 30-30 Me (CH ₂ ) ₂ H CH ₂ OPh 4-EtS-Ph O 30-31 Me (CH ₂ ) ₂ H CH ₂ OPh 4-iPrS-Ph O 30-32 Me (CH ₂ ) ₂ H CH ₂ OPh 4-MeSO ₂ -Ph O 30- 33 Me (CH ₂ ) ₂ H CH ₂ OPh 4-EtSO ₂ -Ph O 30- 34 Me (CH ₂ ) ₂ H CH ₂ OPh 4-iPrSO ₂ -Ph O 30- 35 Me (CH ₂ ) ₂ H CH ₂ OPh 4- (Pyr-2) Ph O 30- 36 Me (CH ₂ ) ₂ H CH ₂ OPh 4- (Pyr-3) Ph O 30- 37 Me (CH ₂ ) ₂ H CH ₂ OPh 4- (Pyr-4) Ph O 30- 38 Me (CH ₂ ) ₂ H CH ₂ OPh 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0161]

[Table 31] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 31- 1 Me (CH ₂ ) ₂ H CH ₂ SPh 4-Et-Ph O 31- 2 Me (CH ₂ ) ₂ H CH ₂ SPh 4-iPr-Ph O 31- 3 Me (CH ₂ ) ₂ H CH ₂ SPh 3-Ph-Ph O 31- 4 Me (CH ₂ ) ₂ H CH ₂ SPh 4-Ph-Ph O 31-5 Me (CH ₂ ) ₂ H CH ₂ SPh 3-Pyr O 31-6 Me (CH ₂ ) ₂ H CH ₂ SPh 5-Me-3 -Pyr O 31- 7 Me (CH ₂ ) ₂ H CH ₂ SPh 5-Et-3-Pyr O 31- 8 Me (CH ₂ ) ₂ H CH ₂ SPh 5-Ph-3-Pyr O 31- 9 Me ( CH ₂ ) ₂ H CH ₂ SPh 6-Me-3-Pyr O 31-10 Me (CH ₂ ) ₂ H CH ₂ SPh 6-Et-3-Pyr O 31-11 Me (CH ₂ ) ₂ H CH ₂ SPh 6-Ph-3-Pyr O 31-12 Me (CH ₂ ) ₂ H CH ₂ SPh 6-MeO-3-Pyr O 31-13 Me (CH ₂ ) ₂ H CH ₂ SPh 6-EtO-3-Pyr O 31-14 Me (CH ₂ ) ₂ H CH ₂ SPh 6-iPrO-3-Pyr O 31-15 Me (CH ₂ ) ₂ H CH ₂ SPh 6-MeS-3-Pyr O 31-16 Me (CH ₂ ) ₂ H CH ₂ SPh 6-EtS-3-Pyr O 31-17 Me (CH ₂ ) ₂ H C H ₂ SPh 6-iPrS-3-Pyr O 31-18 Me (CH ₂ ) ₂ H CH ₂ SPh 6-MeSO ₂ -3-Pyr O 31-19 Me (CH ₂ ) ₂ H CH ₂ SPh 6-EtSO ₂ -3-Pyr O 31-20 Me (CH ₂ ) ₂ H CH ₂ SPh 6-iPrSO ₂ -3-Pyr O 31- 21 Me (CH ₂ ) ₂ H CH ₂ SPh 6-Bz-3-Pyr O 31- _{22 Me (CH 2) 2 H} CH 2 SPh 6-PhO-3-Pyr O 31- 23 Me (CH 2) 2 H CH 2 SPh 6-PhS-3-Pyr O 31- 24 Me (CH 2) 2 H CH ₂ SPh 6-PhSO ₂ -3-Pyr O 31-25 Me (CH ₂ ) ₂ H CH ₂ SPh 2-Quin O 31- 26 Me (CH ₂ ) ₂ H CH ₂ SPh 4-MeO-Ph O 31- 27 Me (CH ₂ ) ₂ H CH ₂ SPh 4-EtO-Ph O 31- 28 Me (CH ₂ ) ₂ H CH ₂ SPh 4-iPrO-Ph O 31- 29 Me (CH ₂ ) ₂ H CH ₂ SPh 4 -MeS-Ph O 31-30 Me (CH ₂ ) ₂ H CH ₂ SPh 4-EtS-Ph O 31- 31 Me (CH ₂ ) ₂ H CH ₂ SPh 4-iPrS-Ph O 31- 32 Me (CH ₂ ) ₂ H CH ₂ SPh 4-MeSO ₂ -Ph O 31- 33 Me (CH ₂ ) ₂ H CH ₂ SPh 4-EtSO ₂ -Ph O 31- 34 Me (CH ₂ ) ₂ H CH ₂ SPh 4-iPrSO ₂ -Ph O 31- 35 Me (CH ₂ ) ₂ H CH ₂ SPh 4- (Pyr-2) Ph O 31- 36 Me (CH ₂ ) ₂ H CH ₂ SPh 4- (Pyr-3) Ph O 31- 37 Me (CH ₂ ) ₂ H CH ₂ SPh 4- (Pyr-4) Ph O 31- 38 Me (CH ₂ ) ₂ H CH ₂ SPh 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0162]

[Table 32] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 32- 1 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-Et-Ph O 32- 2 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-iPr-Ph O 32- 3 Me (CH ₂ ) ₂ H CH ₂ NHPh 3-Ph-Ph O 32- 4 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-Ph-Ph O 32- 5 Me (CH ₂ ) ₂ H CH ₂ NHPh 3-Pyr O 32- 6 Me (CH ₂ ) ₂ H CH ₂ NHPh 5-Me-3 -Pyr O 32- 7 Me (CH ₂ ) ₂ H CH ₂ NHPh 5-Et-3-Pyr O 32- 8 Me (CH ₂ ) ₂ H CH ₂ NHPh 5-Ph-3-Pyr O 32- 9 Me ( CH ₂ ) ₂ H CH ₂ NHPh 6-Me-3-Pyr O 32- 10 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-Et-3-Pyr O 32- 11 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-Ph-3-Pyr O 32- 12 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-MeO-3-Pyr O 32-13 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-EtO-3-Pyr O 32- 14 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-iPrO-3-Pyr O 32- 15 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-MeS-3-Pyr O 32- 16 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-EtS-3-Pyr O 32-17 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-iPrS-3-Pyr O 32-18 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-MeSO ₂ -3-Pyr O 32-19 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-EtSO ₂ -3-Pyr O 32- 20 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-iPrSO ₂ -3-Pyr O 32-21 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-Bz -3-Pyr O 32-22 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-PhO-3-Pyr O 32-23 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-PhS-3-Pyr O 32- 24 Me (CH ₂ ) ₂ H CH ₂ NHPh 6-PhSO ₂ -3-Pyr O 32-25 Me (CH ₂ ) ₂ H CH ₂ NHPh 2-Quin O 32-26 Me (CH ₂ ) ₂ H CH ₂ NHPh 4 -MeO-Ph O 32-27 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-EtO-Ph O 32-28 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-iPrO-Ph O 32-29 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-MeS-Ph O 32- 30 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-EtS-Ph O 32-31 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-iPrS-Ph O 32-32 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-MeSO ₂ -Ph O 32-33 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-EtSO ₂ -Ph O 32-34 Me (CH ₂ ) ₂ H CH ₂ NHPh 4-iPrSO ₂ -Ph O 32-35 Me (CH ₂ ) ₂ H CH ₂ NHPh 4- (Pyr-2) Ph O 32-36 Me (CH ₂ ) ₂ H CH ₂ NHPh 4- (Pyr- 3) Ph O 32-37 Me (CH ₂ ) ₂ H CH ₂ NHPh 4- (Pyr-4) Ph O 32-38 Me (CH ₂ ) ₂ H CH ₂ NHPh 3-Ph-6-Py r O ──────────────────────────────────.

[0163]

[Table 33] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 33-1 Me (CH ₂ ) ₂ H − OMe 4-Et-Ph O 33- 2 Me (CH ₂ ) ₂ H- OMe 4-iPr-Ph O 33- 3 Me (CH ₂ ) ₂ H- OMe 3-Ph-Ph O 33- 4 Me (CH ₂ ) ₂ H-OMe 4-Ph-Ph O 33-5 Me (CH ₂ ) ₂ H-OMe 3-Pyr O 33-6 Me (CH ₂ ) ₂ H-OMe 5-Me-3-Pyr O 33-7 Me (CH ₂ ) ₂ H-OMe 5-Et-3-Pyr O 33-8 Me (CH ₂ ) ₂ H-OMe 5-Ph-3-Pyr O 33-9 Me (CH ₂ ) ₂ H-OMe 6 -Me-3-Pyr O 33-10 Me (CH ₂ ) ₂ H− OMe 6-Et-3-Pyr O 33-11 Me (CH ₂ ) ₂ H− OMe 6-Ph-3-Pyr O 33-12 Me (CH ₂ ) ₂ H-OMe 6-MeO-3-Pyr O 33-13 Me (CH ₂ ) ₂ H-OMe 6 -EtO-3-Pyr O 33-14 Me (CH ₂ ) ₂ H-OMe 6 -iPrO-3-Pyr O 33-15 Me (CH ₂ ) ₂ H− OMe 6-MeS-3-Pyr O 33-16 Me (CH ₂ ) ₂ H− OMe 6-EtS-3-Pyr O 33-17 Me (CH ₂ ) ₂ H − OMe 6-iPrS-3- Pyr O 33-18 Me (CH ₂ ) ₂ H− OMe 6-MeSO ₂ -3-Pyr O 33-19 Me (CH ₂ ) ₂ H− OMe 6-EtSO ₂ -3-Pyr O 33-20 Me (CH _{2) 2 H - OMe 6-} iPrSO 2 -3-Pyr O 33- 21 Me (CH 2) 2 H - OMe 6-Bz-3-Pyr O 33- 22 Me (CH 2) 2 H - OMe 6-PhO -3-Pyr O 33- 23 Me ( CH 2) 2 H - OMe 6-PhS-3-Pyr O 33- 24 Me (CH 2) 2 H - OMe 6-PhSO 2 -3-Pyr O 33- 25 Me (CH ₂ ) ₂ H-OMe 2-Quin O 33- 26 Me (CH ₂ ) ₂ H-OMe 4-MeO-Ph O 33- 27 Me (CH ₂ ) ₂ H- OMe 4-EtO-Ph O 33- 28 Me (CH ₂ ) ₂ H-OMe 4-iPrO-Ph O 33-29 Me (CH ₂ ) ₂ H-OMe 4-MeS-Ph O 33-30 Me (CH ₂ ) ₂ H-OMe 4-EtS- Ph O 33- 31 Me (CH ₂ ) ₂ H− OMe 4-iPrS-Ph O 33- 32 Me (CH ₂ ) ₂ H− OMe 4-MeSO ₂ -Ph O 33- 33 Me (CH ₂ ) ₂ H − OMe 4-EtSO ₂ -Ph O 33- 34 Me (CH ₂ ) ₂ H− OMe 4-iPrSO ₂ -Ph O 33- 35 Me (CH ₂ ) ₂ H− OMe 4- (Pyr-2) Ph O 33- 36 Me (CH ₂ ) ₂ H-OMe 4- (Pyr-3) Ph O 33- 37 Me (CH ₂ ) ₂ H-OMe 4- (Pyr-4) Ph O 33- 38 Me (CH ₂ ) ₂ H − OMe 3-Ph-6-Pyr O ──────────────────────── ──────────.

[0164]

[Table 34] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 34- 1 Me (CH ₂ ) ₂ H − OEt 4-Et-Ph O 34- 2 Me (CH ₂ ) ₂ H- OEt 4-iPr-Ph O 34- 3 Me (CH ₂ ) ₂ H- OEt 3-Ph-Ph O 34- 4 Me (CH ₂ ) ₂ H-OEt 4-Ph-Ph O 34-5 Me (CH ₂ ) ₂ H-OEt 3-Pyr O 34-6 Me (CH ₂ ) ₂ H-OEt 5-Me-3-Pyr O 34-7 Me (CH ₂ ) ₂ H-OEt 5-Et-3-Pyr O 34- 8 Me (CH ₂ ) ₂ H-OEt 5-Ph-3-Pyr O 34- 9 Me (CH ₂ ) ₂ H-OEt 6 -Me-3-Pyr O 34- 10 Me (CH ₂ ) ₂ H− OEt 6-Et-3-Pyr O 34− 11 Me (CH ₂ ) ₂ H− OEt 6-Ph-3-Pyr O 34-12 Me (CH ₂ ) ₂ H-OEt 6-MeO-3-Pyr O 34-13 Me (CH ₂ ) ₂ H-OEt 6-EtO-3-Pyr O 34-14 Me (CH ₂ ) ₂ H-OEt 6 -iPrO-3-Pyr O 34- 15 Me (CH ₂ ) ₂ H-OEt 6-MeS-3-Pyr O 34- 16 Me (CH ₂ ) ₂ H-OEt 6-EtS-3-Pyr O 34- 17 Me (CH ₂ ) ₂ H − OEt 6-iPrS-3- Pyr O 34-18 Me (CH ₂ ) ₂ H− OEt 6-MeSO ₂ -3-Pyr O 34-19 Me (CH ₂ ) ₂ H− OEt 6-EtSO ₂ -3-Pyr O 34-20 Me (CH ₂ ) ₂ H-OEt 6-iPrSO ₂ -3-Pyr O 34- 21 Me (CH ₂ ) ₂ H- OEt 6-Bz-3-Pyr O 34- 22 Me (CH ₂ ) ₂ H- OEt 6-PhO -3-Pyr O 34- 23 Me ( CH 2) 2 H - OEt 6-PhS-3-Pyr O 34- 24 Me (CH 2) 2 H - OEt 6-PhSO 2 -3-Pyr O 34- 25 Me (CH ₂ ) ₂ H-OEt 2-Quin O 34- 26 Me (CH ₂ ) ₂ H-OEt 4-MeO-Ph O 34- 27 Me (CH ₂ ) ₂ H-OEt 4-EtO-Ph O 34- 28 Me (CH ₂ ) ₂ H-OEt 4-iPrO-Ph O 34-29 Me (CH ₂ ) ₂ H-OEt 4-MeS-Ph O 34-30 Me (CH ₂ ) ₂ H-OEt 4-EtS- Ph O 34- 31 Me (CH ₂ ) ₂ H- OEt 4-iPrS-Ph O 34- 32 Me (CH ₂ ) ₂ H- OEt 4-MeSO ₂ -Ph O 34- 33 Me (CH ₂ ) ₂ H − OEt 4-EtSO ₂ -Ph O 34- 34 Me (CH ₂ ) ₂ H- OEt 4-iPrSO ₂ -Ph O 34- 35 Me (CH ₂ ) ₂ H- OEt 4- (Pyr-2) Ph O 34- 36 Me (CH ₂ ) ₂ H-OEt 4- (Pyr-3) Ph O 34- 37 Me (CH ₂ ) ₂ H-OEt 4- (Pyr-4) Ph O 34- 38 Me (CH ₂ ) ₂ H − OEt 3-Ph-6-Pyr O ──────────────────────── ──────────.

[0165]

[Table 35] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 35- 1 Me (CH ₂ ) ₂ H − OPr 4-Et-Ph O 35- 2 Me (CH ₂ ) ₂ H-OPr 4-iPr-Ph O 35- 3 Me (CH ₂ ) ₂ H-OPr 3-Ph-Ph O 35- 4 Me (CH ₂ ) ₂ H-OPr 4-Ph-Ph O 35- 5 Me (CH ₂ ) ₂ H-OPr 3-Pyr O 35- 6 Me (CH ₂ ) ₂ H-OPr 5-Me-3-Pyr O 35- 7 Me (CH ₂ ) ₂ H-OPr 5-Et-3-Pyr O 35- 8 Me (CH ₂ ) ₂ H-OPr 5-Ph-3-Pyr O 35- 9 Me (CH ₂ ) ₂ H-OPr 6 -Me-3-Pyr O 35- 10 Me (CH ₂ ) ₂ H-OPr 6-Et-3-Pyr O 35-11 Me (CH ₂ ) ₂ H-OPr 6-Ph-3-Pyr O 35-12 Me (CH ₂ ) ₂ H-OPr 6-MeO-3-Pyr O 35-13 Me (CH ₂ ) ₂ H-OPr 6-EtO-3-Pyr O 35-14 Me (CH ₂ ) ₂ H-OPr 6 -iPrO-3-Pyr O 35-15 Me (CH ₂ ) ₂ H-OPr 6-MeS-3-Pyr O 35-16 16 Me (CH ₂ ) ₂ H-OPr 6-EtS-3-Pyr O 35-17 Me (CH ₂ ) ₂ H − OPr 6-iPrS-3- Pyr O 35-18 Me (CH ₂ ) ₂ H-OPr 6-MeSO ₂ -3-Pyr O 35-19 Me (CH ₂ ) ₂ H-OPr 6-EtSO ₂ -3-Pyr O 35-20 Me (CH ₂ ) ₂ H-OPr 6-iPrSO ₂ -3-Pyr O 35- 21 Me (CH ₂ ) ₂ H-OPr 6-Bz-3-Pyr O 35- 22 Me (CH ₂ ) ₂ H-OPr 6-PhO -3-Pyr O 35- 23 Me (CH ₂ ) ₂ H-OPr 6-PhS-3-Pyr O 35- 24 Me (CH ₂ ) ₂ H-OPr 6-PhSO ₂ -3-Pyr O 35- 25 Me (CH ₂ ) ₂ H-OPr 2-Quin O 35- 26 Me (CH ₂ ) ₂ H-OPr 4-MeO-Ph O 35- 27 Me (CH ₂ ) ₂ H-OPr 4-EtO-Ph O 35- 28 Me (CH ₂ ) ₂ H-OPr 4-iPrO-Ph O 35-29 Me (CH ₂ ) ₂ H-OPr 4-MeS-Ph O 35-30 Me (CH ₂ ) ₂ H-OPr 4-EtS- Ph O 35- 31 Me (CH ₂ ) ₂ H − OPr 4-iPrS-Ph O 35- 32 Me (CH ₂ ) ₂ H − OPr 4-MeSO ₂ -Ph O 35- 33 Me (CH ₂ ) ₂ H − OPr 4-EtSO ₂ -Ph O 35- 34 Me (CH ₂ ) ₂ H-OPr 4-iPrSO ₂ -Ph O 35- 35 Me (CH ₂ ) ₂ H-OPr 4- (Pyr-2) Ph O 35- 36 Me (CH ₂ ) ₂ H-OPr 4- (Pyr-3) Ph O 35- 37 Me (CH ₂ ) ₂ H-OPr 4- (Pyr-4) Ph O 35- 38 Me (CH ₂ ) ₂ H − OPr 3-Ph-6-Pyr O ──────────────────────── ──────────.

[0166]

[Table 36] Example R ¹ R ² R ³ ZW X Y Compound No. ──────────────────────────────────── 36- 1 Me (CH ₂ ) ₂ H ( CH ₂ ) ₂ OiPr 4-Et-Ph O 36- 2 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-iPr-Ph O 36- 3 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 3 -Ph-Ph O 36- 4 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-Ph-Ph O 36- 5 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 3-Pyr O 36-6 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 5-Me-3-Pyr O 36-7 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 5-Et-3-Pyr O 36-8 Me ( CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 5-Ph-3-Pyr O 36-9 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-Me-3-Pyr O 36-10 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-Et-3-Pyr O 36-11 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-Ph-3-Pyr O 36-12 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-MeO-3-Pyr O 36- 13 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-EtO-3-Pyr O 36- 14 Me (CH ₂ ) ₂ H ( CH ₂ ) ₂ OiPr 6-iPrO-3-Pyr O 36-15 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-MeS-3-Pyr O 36-16 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-EtS-3-Pyr O 36-17 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-iPrS-3-Pyr O 36-18 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-MeSO ₂ -3-Pyr O 36-19 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6 -EtSO ₂ -3-Pyr O 36-20 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6 -iPrSO ₂ -3-Pyr O 36-21 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6 -Bz-3-Pyr O 36-22 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-PhO-3-Pyr O 36-23 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-PhS -3-Pyr O 36- 24 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-PhSO ₂ -3-Pyr O 36- 25 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 2-Quin O 36- 26 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-MeO-Ph O 36- 27 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-EtO-Ph O 36- 28 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-iPrO-Ph O 36-29 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-MeS-Ph O 36-30 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-EtS-Ph O 36- 31 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-iPrS-Ph O 36- 32 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4- MeSO ₂ -Ph O 36- 33 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-EtSO ₂ -Ph O 36- 34 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-iPrSO ₂ -Ph O 36- 35 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4- (Pyr-2) Ph O 36- 36 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4- (Pyr-3) Ph O 36- 37 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4- (Pyr-4) Ph O 36- 38 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 3-Ph-6-Pyr O ───── ─────────────────────────────.

[0167]

[Table 37] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 37- 1 Me (CH ₂ ) ₂ H ( CH ₂ ) ₂ OMe 4-Et-Ph O 37- 2 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-iPr-Ph O 37- 3 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 3 -Ph-Ph O 37- 4 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-Ph-Ph O 37- 5 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 3-Pyr O 37- 6 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 5-Me-3-Pyr O 37- 7 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 5-Et-3-Pyr O 37- 8 Me ( CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 5-Ph-3-Pyr O 37-9 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-Me-3-Pyr O 37-10 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-Et-3-Pyr O 37-11 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-Ph-3-Pyr O 37-12 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-MeO-3-Pyr O 37-13 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-EtO-3-Pyr O 37-14 Me (CH ₂ ) ₂ H ( CH ₂ ) ₂ OMe 6-iPrO-3-Pyr O 37-15 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-MeS-3 -Pyr O 37-16 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-EtS-3-Pyr O 37-17 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-iPrS-3-Pyr O 37-18 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-MeSO ₂ -3-Pyr O 37-19 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-EtSO ₂ -3-Pyr O 37-20 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-iPrSO ₂ -3-Pyr O 37-21 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-Bz-3-Pyr O 37- 22 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-PhO-3-Pyr O 37-23 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-PhS-3-Pyr O 37- 24 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 6-PhSO ₂ -3-Pyr O 37-25 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 2-Quin O 37-26 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-MeO-Ph O 37- 27 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-EtO-Ph O 37- 28 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-iPrO-Ph O 37- 29 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-MeS-Ph O 37-30 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-EtS -Ph O 37- 31 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-iPrS-Ph O 37-32 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-MeSO ₂ -Ph O 37- 33 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-EtSO ₂ -Ph O 37-34 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4-iPrSO ₂ -Ph O 37-35 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4- (Pyr- 2) Ph O 37- 36 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4- (Pyr-3) Ph O 37- 37 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 4- (Pyr- 4) Ph O 37- 38 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OMe 3-Ph-6-Pyr O ────────────────────── ────────────.

[0168]

[Table 38] Example R ¹ R ² R ³ ZW X Y Compound No. ──────────────────────────────────── 38- 1 Me (CH ₂ ) ₂ H ( CH ₂ ) ₂ OEt 4-Et-Ph O 38- 2 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-iPr-Ph O 38- 3 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 3 -Ph-Ph O 38-4 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-Ph-Ph O 38-5 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 3-Pyr O 38-6 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 5-Me-3-Pyr O 38-7 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 5-Et-3-Pyr O 38-8 Me ( CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 5-Ph-3-Pyr O 38-9 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-Me-3-Pyr O 38-10 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-Et-3-Pyr O 38-11 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-Ph-3-Pyr O 38-12 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-MeO-3-Pyr O 38-13 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-EtO-3-Pyr O 38-14 Me (CH ₂ ) ₂ H ( CH ₂ ) ₂ OEt 6-iPrO-3-Pyr O 38-15 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-MeS-3 -Pyr O 38-16 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-EtS-3-Pyr O 38-17 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-iPrS-3-Pyr O 38-18 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-MeSO ₂ -3-Pyr O 38-19 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-EtSO ₂ -3-Pyr O 38-20 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-iPrSO ₂ -3-Pyr O 38- 21 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-Bz-3-Pyr O _{38- 22 Me (CH 2) 2} H (CH 2) 2 OEt 6-PhO-3-Pyr O 38- 23 Me (CH 2) 2 H (CH 2) 2 OEt 6-PhS-3-Pyr O 38- 24 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 6-PhSO ₂ -3-Pyr O 38-25 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 2-Quin O 38-26 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-MeO-Ph O 38- 27 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-EtO-Ph O 38- 28 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-iPrO-Ph O 38- 29 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-MeS-Ph O 38-30 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-EtS -Ph O 38-31 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-iPrS-Ph O 38-32 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-MeSO ₂ -Ph O 38- 33 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-EtSO ₂ -Ph O 38-34 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4-iPrSO ₂ -Ph O 38-35 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4- (Pyr- 2) Ph O 38- 36 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4- (Pyr-3) Ph O 38- 37 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 4- (Pyr- 4) Ph O 38- 38 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OEt 3-Ph-6-Pyr O ────────────────────── ────────────.

[0169]

[Table 39] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 39- 1 Me (CH ₂ ) ₂ H ( CH ₂ ) ₂ OPr 4-Et-Ph O 39- 2 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-iPr-Ph O 39- 3 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 3 -Ph-Ph O 39- 4 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-Ph-Ph O 39- 5 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 3-Pyr O 39- 6 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 5-Me-3-Pyr O 39-7 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 5-Et-3-Pyr O 39-8 Me ( CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 5-Ph-3-Pyr O 39-9 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-Me-3-Pyr O 39-10 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-Et-3-Pyr O 39-11 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-Ph-3-Pyr O 39-12 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-MeO-3-Pyr O 39-13 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-EtO-3-Pyr O 39-14 Me (CH ₂ ) ₂ H ( CH ₂ ) ₂ OPr 6-iPrO-3-Pyr O 39-15 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-MeS-3 -Pyr O 39-16 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-EtS-3-Pyr O 39-17 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-iPrS-3-Pyr O 39-18 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-MeSO ₂ -3-Pyr O 39-19 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-EtSO ₂ -3-Pyr O 39-20 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-iPrSO ₂ -3-Pyr O 39- 21 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-Bz-3-Pyr O _{39- 22 Me (CH 2) 2} H (CH 2) 2 OPr 6-PhO-3-Pyr O 39- 23 Me (CH 2) 2 H (CH 2) 2 OPr 6-PhS-3-Pyr O 39- 24 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 6-PhSO ₂ -3-Pyr O 39-25 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 2-Quin O 39-26 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-MeO-Ph O 39- 27 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-EtO-Ph O 39- 28 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-iPrO-Ph O 39- 29 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-MeS-Ph O 39-30 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-EtS -Ph O 39- 31 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-iPrS-Ph O 39- 32 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-MeSO ₂ -Ph O 39- 33 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-EtSO ₂ -Ph O 39-34 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4-iPrSO ₂ -Ph O 39-35 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4- (Pyr- 2) Ph O 39- 36 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4- (Pyr-3) Ph O 39- 37 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 4- (Pyr- 4) Ph O 39- 38 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OPr 3-Ph-6-Pyr O ────────────────────── ────────────.

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[Table 40] 例 示 Examples R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 40- 1 Me (CH ₂ ) ₂ H ( CH ₂ ) ₂ OiPr 4-Et-Ph O 40- 2 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-iPr-Ph O 40- 3 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 3 -Ph-Ph O 40- 4 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-Ph-Ph O 40- 5 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 3-Pyr O 40-6 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 5-Me-3-Pyr O 40- 7 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 5-Et-3-Pyr O 40- 8 Me ( CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 5-Ph-3-Pyr O 40-9 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-Me-3-Pyr O 40-10 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-Et-3-Pyr O 40-11 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-Ph-3-Pyr O 40-12 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-MeO-3-Pyr O 40- 13 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-EtO-3-Pyr O 40- 14 Me (CH ₂ ) ₂ H ( CH ₂ ) ₂ OiPr 6-iPrO-3-Pyr O 40-15 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-MeS-3-Pyr O 40-16 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-EtS-3-Pyr O 40-17 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-iPrS-3-Pyr O 40-18 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-MeSO ₂ -3-Pyr O 40-19 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6 -EtSO ₂ -3-Pyr O 40-20 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6 -iPrSO ₂ -3-Pyr O 40-21 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6 -Bz-3-Pyr O 40-22 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-PhO-3-Pyr O 40-23 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-PhS -3-Pyr O 40-24 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 6-PhSO ₂ -3-Pyr O 40-25 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 2-Quin O 40- 26 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-MeO-Ph O 40- 27 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-EtO-Ph O 40- 28 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-iPrO-Ph O 40-29 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-MeS-Ph O 40-30 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-EtS-Ph O 40- 31 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-iPrS-Ph O 40- 32 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4- MeSO ₂ -Ph O 40- 33 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-EtSO ₂ -Ph O 40- 34 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4-iPrSO ₂ -Ph O 40- 35 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4- (Pyr-2) Ph O 40- 36 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4- (Pyr-3) Ph O 40- 37 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 4- (Pyr-4) Ph O 40- 38 Me (CH ₂ ) ₂ H (CH ₂ ) ₂ OiPr 3-Ph-6-Pyr O ───── ─────────────────────────────.

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[Table 41] 例 示 Examples R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 41-1 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4-Et-Ph O 41- 2 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4-iPr-Ph O 41- 3 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 3-Ph-Ph O 41 -4 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4-Ph-Ph O 41-5 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 3-Pyr O 41-6 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 5-Me-3-Pyr O 41- 7 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 5-Et-3-Pyr O 41- 8 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 5-Ph-3 _{-Pyr O 41- 9 Me (CH 2} ) 2 H CH 2 NH 2 6-Me-3-Pyr O 41- 10 Me (CH 2) 2 H CH 2 NH 2 6-Et-3-Pyr O 41- 11 _{Me (CH 2) 2 H CH} 2 NH 2 6-Ph-3-Pyr O 41- 12 Me (CH 2) 2 H CH 2 NH 2 6-MeO-3-Pyr O 41- 13 Me (CH 2) 2 _{H CH 2 NH 2 6-EtO} -3-Pyr O 41- 14 Me (CH 2) 2 H CH 2 NH 2 6-iPrO-3-Pyr O 41- 15 Me (CH 2) 2 H CH 2 NH 2 6 -MeS-3-Pyr O 41- 16 Me (CH 2) 2 H CH 2 NH 2 6-EtS-3-Pyr O 41- 17 _{Me (CH 2) 2 H CH} 2 NH 2 6-iPrS-3-Pyr O 41- 18 Me (CH 2) 2 H CH 2 NH 2 6-MeSO 2 -3-Pyr O 41- 19 Me (CH 2) _{2 H CH 2 NH 2 6-} EtSO 2 -3-Pyr O 41- 20 Me (CH 2) 2 H CH 2 NH 2 6-iPrSO 2 -3-Pyr O 41- 21 Me (CH 2) 2 H CH 2 _{NH 2 6-Bz-3-} Pyr O 41- 22 Me (CH 2) 2 H CH 2 NH 2 6-PhO-3-Pyr O 41- 23 Me (CH 2) 2 H CH 2 NH 2 6-PhS- 3-Pyr O 41- 24 Me ( CH 2) 2 H CH 2 NH 2 6-PhSO 2 -3-Pyr O 41- 25 Me (CH 2) 2 H CH 2 NH 2 2-Quin O 41- 26 Me ( CH ₂ ) ₂ H CH ₂ NH ₂ 4-MeO-Ph O 41- 27 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4-EtO-Ph O 41- 28 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4 -iPrO-Ph O 41- 29 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4-MeS-Ph O 41-30 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4-EtS-Ph O 41- 31 Me ( CH ₂ ) ₂ H CH ₂ NH ₂ 4-iPrS-Ph O 41- 32 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4-MeSO ₂ -Ph O 41- 33 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4-EtSO ₂ -Ph O 41- 34 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4-iPrSO ₂ -Ph O 41- 35 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4- (Pyr-2) Ph O 41- 36 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4- (Pyr-3) Ph O 41- 37 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 4- (Pyr-4) Ph O 41- 38 Me (CH ₂ ) ₂ H CH ₂ NH ₂ 3-Ph-6-Py r O ──────────────────────────────────.

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[Table 42] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 42-1 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-Et-Ph O 42- 2 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-iPr-Ph O 42- 3 Me (CH ₂ ) ₂ H CH ₂ NHMe 3-Ph-Ph O 42- 4 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-Ph-Ph O 42-5 Me (CH ₂ ) ₂ H CH ₂ NHMe 3-Pyr O 42-6 Me (CH ₂ ) ₂ H CH ₂ NHMe 5-Me-3 -Pyr O 42- 7 Me (CH ₂ ) ₂ H CH ₂ NHMe 5-Et-3-Pyr O 42- 8 Me (CH ₂ ) ₂ H CH ₂ NHMe 5-Ph-3-Pyr O 42- 9 Me ( CH ₂ ) ₂ H CH ₂ NHMe 6-Me-3-Pyr O 42-10 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-Et-3-Pyr O 42-11 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-Ph-3-Pyr O 42-12 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-MeO-3-Pyr O 42- 13 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-EtO-3-Pyr O 42- 14 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-iPrO-3-Pyr O 42-15 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-MeS-3-Pyr O 42-16 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-EtS-3-Pyr O 42-17 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-iPrS-3-Pyr O 42-18 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-MeSO ₂ -3-Pyr O 42-19 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-EtSO ₂ -3-Pyr O 42-20 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-iPrSO ₂ -3-Pyr O 42- 21 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-Bz -3-Pyr O 42- 22 Me ( CH 2) 2 H CH 2 NHMe 6-PhO-3-Pyr O 42- 23 Me (CH 2) 2 H CH 2 NHMe 6-PhS-3-Pyr O 42- 24 Me (CH ₂ ) ₂ H CH ₂ NHMe 6-PhSO ₂ -3-Pyr O 42-25 Me (CH ₂ ) ₂ H CH ₂ NHMe 2-Quin O 42- 26 Me (CH ₂ ) ₂ H CH ₂ NHMe 4 -MeO-Ph O 42- 27 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-EtO-Ph O 42- 28 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-iPrO-Ph O 42- 29 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-MeS-Ph O 42-30 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-EtS-Ph O 42- 31 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-iPrS-Ph O 42- 32 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-MeSO ₂ -Ph O 42- 33 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-EtSO ₂ -Ph O 42- 34 Me (CH ₂ ) ₂ H CH ₂ NHMe 4-iPrSO ₂ -Ph O 42- 35 Me (CH ₂ ) ₂ H CH ₂ NHMe 4- (Pyr-2) Ph O 42- 36 Me (CH ₂ ) ₂ H CH ₂ NHMe 4- (Pyr- 3) Ph O 42- 37 Me (CH ₂ ) ₂ H CH ₂ NHMe 4- (Pyr-4) Ph O 42- 38 Me (CH ₂ ) ₂ H CH ₂ NHMe 3-Ph-6-Py r O ──────────────────────────────────.

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[Table 43] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 43- 1 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-Et-Ph O 43- 2 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-iPr-Ph O 43- 3 Me (CH ₂ ) ₂ H CH ₂ NHEt 3-Ph-Ph O 43- 4 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-Ph-Ph O 43-5 Me (CH ₂ ) ₂ H CH ₂ NHEt 3-Pyr O 43-6 Me (CH ₂ ) ₂ H CH ₂ NHEt 5-Me-3 -Pyr O 43- 7 Me (CH ₂ ) ₂ H CH ₂ NHEt 5-Et-3-Pyr O 43- 8 Me (CH ₂ ) ₂ H CH ₂ NHEt 5-Ph-3-Pyr O 43- 9 Me ( CH ₂ ) ₂ H CH ₂ NHEt 6-Me-3-Pyr O 43-10 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-Et-3-Pyr O 43-11 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-Ph-3-Pyr O 43-12 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-MeO-3-Pyr O 43- 13 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-EtO-3-Pyr O 43-14 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-iPrO-3-Pyr O 43- 15 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-MeS-3-Pyr O 43-16 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-EtS-3-Pyr O 43-17 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-iPrS-3-Pyr O 43-18 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-MeSO ₂ -3-Pyr O 43-19 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-EtSO ₂ -3-Pyr O 43-20 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-iPrSO ₂ -3-Pyr O 43-21 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-Bz -3-Pyr O 43- 22 Me ( CH 2) 2 H CH 2 NHEt 6-PhO-3-Pyr O 43- 23 Me (CH 2) 2 H CH 2 NHEt 6-PhS-3-Pyr O 43- 24 Me (CH ₂ ) ₂ H CH ₂ NHEt 6-PhSO ₂ -3-Pyr O 43-25 Me (CH ₂ ) ₂ H CH ₂ NHEt 2-Quin O 43- 26 Me (CH ₂ ) ₂ H CH ₂ NHEt 4 -MeO-Ph O 43- 27 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-EtO-Ph O 43- 28 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-iPrO-Ph O 43- 29 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-MeS-Ph O 43-30 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-EtS-Ph O 43- 31 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-iPrS-Ph O 43- 32 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-MeSO ₂ -Ph O 43- 33 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-EtSO ₂ -Ph O 43- 34 Me (CH ₂ ) ₂ H CH ₂ NHEt 4-iPrSO ₂ -Ph O 43- 35 Me (CH ₂ ) ₂ H CH ₂ NHEt 4- (Pyr-2) Ph O 43- 36 Me (CH ₂ ) ₂ H CH ₂ NHEt 4- (Pyr- 3) Ph O 43- 37 Me (CH ₂ ) ₂ H CH ₂ NHEt 4- (Pyr-4) Ph O 43- 38 Me (CH ₂ ) ₂ H CH ₂ NHEt 3-Ph-6-Py r O ──────────────────────────────────.

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[Table 44] 例 示 Examples R ¹ R ² R ³ Z W X Y compound number ──────────────────────────────────── 44- 1 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-Et-Ph O 44- 2 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-iPr-Ph O 44- 3 Me (CH ₂ ) ₂ H CH ₂ NHPr 3-Ph-Ph O 44- 4 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-Ph-Ph O 44-5 Me (CH ₂ ) ₂ H CH ₂ NHPr 3-Pyr O 44-6 Me (CH ₂ ) ₂ H CH ₂ NHPr 5-Me-3 -Pyr O 44- 7 Me (CH ₂ ) ₂ H CH ₂ NHPr 5-Et-3-Pyr O 44- 8 Me (CH ₂ ) ₂ H CH ₂ NHPr 5-Ph-3-Pyr O 44- 9 Me ( CH ₂ ) ₂ H CH ₂ NHPr 6-Me-3-Pyr O 44-10 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-Et-3-Pyr O 44-11 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-Ph-3-Pyr O 44-12 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-MeO-3-Pyr O 44- 13 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-EtO-3-Pyr O 44-14 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-iPrO-3-Pyr O 44-15 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-MeS-3-Pyr O 44-16 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-EtS-3-Pyr O 44-17 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-iPrS-3-Pyr O 44-18 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-MeSO ₂ -3-Pyr O 44-19 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-EtSO ₂ -3-Pyr O 44-20 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-iPrSO ₂ -3-Pyr O 44-21 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-Bz -3-Pyr O 44- 22 Me ( CH 2) 2 H CH 2 NHPr 6-PhO-3-Pyr O 44- 23 Me (CH 2) 2 H CH 2 NHPr 6-PhS-3-Pyr O 44- 24 Me (CH ₂ ) ₂ H CH ₂ NHPr 6-PhSO ₂ -3-Pyr O 44-25 Me (CH ₂ ) ₂ H CH ₂ NHPr 2-Quin O 44- 26 Me (CH ₂ ) ₂ H CH ₂ NHPr 4 -MeO-Ph O 44- 27 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-EtO-Ph O 44- 28 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-iPrO-Ph O 44- 29 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-MeS-Ph O 44-30 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-EtS-Ph O 44- 31 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-iPrS-Ph O 44- 32 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-MeSO ₂ -Ph O 44- 33 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-EtSO ₂ -Ph O 44- 34 Me (CH ₂ ) ₂ H CH ₂ NHPr 4-iPrSO ₂ -Ph O 44- 35 Me (CH ₂ ) ₂ H CH ₂ NHPr 4- (Pyr-2) Ph O 44- 36 Me (CH ₂ ) ₂ H CH ₂ NHPr 4- (Pyr- 3) Ph O 44- 37 Me (CH ₂ ) ₂ H CH ₂ NHPr 4- (Pyr-4) Ph O 44- 38 Me (CH ₂ ) ₂ H CH ₂ NHPr 3-Ph-6-Py r O ──────────────────────────────────.

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[Table 45] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 45- 1 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-Et-Ph O 45- 2 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-iPr-Ph O 45- 3 Me (CH ₂ ) ₂ H CH ₂ NHiPr 3-Ph-Ph O 45- 4 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-Ph-Ph O 45-5 Me (CH ₂ ) ₂ H CH ₂ NHiPr 3-Pyr O 45-6 Me (CH ₂ ) ₂ H CH ₂ NHiPr 5-Me-3 -Pyr O 45- 7 Me (CH ₂ ) ₂ H CH ₂ NHiPr 5-Et-3-Pyr O 45- 8 Me (CH ₂ ) ₂ H CH ₂ NHiPr 5-Ph-3-Pyr O 45- 9 Me ( CH ₂ ) ₂ H CH ₂ NHiPr 6-Me-3-Pyr O 45-10 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-Et-3-Pyr O 45- 11 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-Ph-3-Pyr O 45-12 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-MeO-3-Pyr O 45- 13 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-EtO-3-Pyr O 45- 14 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-iPrO-3-Pyr O 45- 15 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-MeS-3-Pyr O 45- 16 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-EtS -3-Pyr O 45- 17 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-iPrS-3-Pyr O 45- 18 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-MeSO ₂ -3-Pyr O 45- 19 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-EtSO ₂ -3-Pyr O 45-20 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-iPrSO ₂ -3-Pyr O 45-21 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-Bz-3-Pyr O 45-22 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-PhO-3-Pyr O 45-23 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-PhS -3-Pyr O 45-24 Me (CH ₂ ) ₂ H CH ₂ NHiPr 6-PhSO ₂ -3-Pyr O 45-25 Me (CH ₂ ) ₂ H CH ₂ NHiPr 2-Quin O 45-26 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-MeO-Ph O 45- 27 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-EtO-Ph O 45- 28 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-iPrO-Ph O 45- 29 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-MeS-Ph O 45-30 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-EtS-Ph O 45- 31 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-iPrS-Ph O 45- 32 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-MeSO ₂ -Ph O 45- 33 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-EtSO ₂ -Ph O 45- 34 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4-iPrSO ₂ -Ph O 45- 35 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4- (Pyr-2) Ph O 45- 36 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4- (Pyr-3) Ph O 45- 37 Me (CH ₂ ) ₂ H CH ₂ NHiPr 4- (Pyr-4) Ph O 45- 38 Me (CH ₂ ) ₂ H CH ₂ NHiPr 3-Ph-6-Pyr O ─────────────────────────────── ───.

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[Table 46] 例 示 Examples R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 46- 1 Me (CH ₂ ) ₂ H CH ₂ N (Me) ₂ 4-Et-Ph O 46- 2 Me (CH ₂ ) ₂ H CH ₂ N (Me) ₂ 4-iPr-Ph O 46- 3 Me (CH ₂ ) ₂ H CH ₂ N (Me _{) 2 3-Ph-Ph O} 46- 4 Me (CH 2) 2 H CH 2 N (Me) 2 4-Ph-Ph O 46- 5 Me (CH 2) 2 H CH 2 N (Me) 2 3- _{Pyr O 46- 6 Me (CH 2} ) 2 H CH 2 N (Me) 2 5-Me-3-Pyr O 46- 7 Me (CH 2) 2 H CH 2 N (Me) 2 5-Et-3- _{Pyr O 46- 8 Me (CH 2} ) 2 H CH 2 N (Me) 2 5-Ph-3-Pyr O 46- 9 Me (CH 2) 2 H CH 2 N (Me) 2 6-Me-3- _{Pyr O 46- 10 Me (CH 2} ) 2 H CH 2 N (Me) 2 6-Et-3-Pyr O 46- 11 Me (CH 2) 2 H CH 2 N (Me) 2 6-Ph-3- _{Pyr O 46- 12 Me (CH 2} ) 2 H CH 2 N (Me) 2 6-MeO-3-Pyr O 46- 13 Me (CH 2) 2 H CH 2 N (Me) 2 6-EtO-3- _{Pyr O 46- 14 Me (CH 2} ) 2 H CH 2 N (Me) 2 6-iPrO-3-Pyr O 46- 15 Me (CH 2) 2 H CH 2 N (Me) 2 6-MeS-3- Pyr O 46- 16 M _{e (CH 2) 2 H CH} 2 N (Me) 2 6-EtS-3-Pyr O 46- 17 Me (CH 2) 2 H CH 2 N (Me) 2 6-iPrS-3-Pyr O 46- 18 _{Me (CH 2) 2 H CH} 2 N (Me) 2 6-MeSO 2 -3-Pyr O 46- 19 Me (CH 2) 2 H CH 2 N (Me) 2 6-EtSO 2 -3-Pyr O 46 _{- 20 Me (CH 2) 2} H CH 2 N (Me) 2 6-iPrSO 2 -3-Pyr O 46- 21 Me (CH 2) 2 H CH 2 N (Me) 2 6-Bz-3-Pyr O _{46- 22 Me (CH 2) 2} H CH 2 N (Me) 2 6-PhO-3-Pyr O 46- 23 Me (CH 2) 2 H CH 2 N (Me) 2 6-PhS-3-Pyr O 46- 24 Me (CH ₂ ) ₂ H CH ₂ N (Me) ₂ 6-PhSO ₂ -3-Pyr O 46- 25 Me (CH ₂ ) ₂ H CH ₂ N (Me) ₂ 2-Quin O 46- 26 _{Me (CH 2) 2 H CH} 2 N (Me) 2 4-MeO-Ph O 46- 27 Me (CH 2) 2 H CH 2 N (Me) 2 4-EtO-Ph O 46- 28 Me (CH 2 ) ₂ H CH ₂ N (Me) ₂ 4-iPrO-Ph O 46- 29 Me (CH ₂ ) ₂ H CH ₂ N (Me) ₂ 4-MeS-Ph O 46-30 Me (CH ₂ ) ₂ H CH ₂ N (Me) ₂ 4-EtS-Ph O 46- 31 Me (CH ₂ ) ₂ H CH ₂ N (Me) ₂ 4-iPrS-Ph O 46- 32 Me (CH ₂ ) ₂ H CH ₂ N (Me ) ₂ 4-MeSO ₂ -Ph O 46- 33 Me (CH ₂ ) ₂ H CH ₂ N (Me) ₂ 4-EtSO ₂ -Ph O 46- 34 Me (CH ₂ ) ₂ H CH ₂ N (Me) ₂ 4-iPrSO ₂ -Ph O 46- 35 Me (CH ₂ ) ₂ H CH ₂ N (Me) ₂ 4- (Pyr-2) Ph O 46- 36 Me (CH ₂ ) ₂ H CH ₂ N _{(Me) 2 4- (Pyr-} 3) Ph O 46- 37 Me (CH 2) 2 H CH 2 N (Me) 2 4- (Pyr-4) Ph O 46- 38 Me (CH 2) 2 H CH ₂ N (Me) ₂ 3-Ph-6-Pyr O ──────────────────────────────────.

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[Table 47] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 47- 1 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4-Et-Ph O 47- 2 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4-iPr-Ph O 47- 3 Me (CH ₂ ) ₂ H CH ₂ N (Et _{) 2 3-Ph-Ph O} 47- 4 Me (CH 2) 2 H CH 2 N (Et) 2 4-Ph-Ph O 47- 5 Me (CH 2) 2 H CH 2 N (Et) 2 3- _{Pyr O 47- 6 Me (CH 2} ) 2 H CH 2 N (Et) 2 5-Me-3-Pyr O 47- 7 Me (CH 2) 2 H CH 2 N (Et) 2 5-Et-3- _{Pyr O 47- 8 Me (CH 2} ) 2 H CH 2 N (Et) 2 5-Ph-3-Pyr O 47- 9 Me (CH 2) 2 H CH 2 N (Et) 2 6-Me-3- _{Pyr O 47- 10 Me (CH 2} ) 2 H CH 2 N (Et) 2 6-Et-3-Pyr O 47- 11 Me (CH 2) 2 H CH 2 N (Et) 2 6-Ph-3- _{Pyr O 47- 12 Me (CH 2} ) 2 H CH 2 N (Et) 2 6-MeO-3-Pyr O 47- 13 Me (CH 2) 2 H CH 2 N (Et) 2 6-EtO-3- _{Pyr O 47- 14 Me (CH 2} ) 2 H CH 2 N (Et) 2 6-iPrO-3-Pyr O 47- 15 Me (CH 2) 2 H CH 2 N (Et) 2 6-MeS-3- Pyr O 47-16 M _{e (CH 2) 2 H CH} 2 N (Et) 2 6-EtS-3-Pyr O 47- 17 Me (CH 2) 2 H CH 2 N (Et) 2 6-iPrS-3-Pyr O 47- 18 _{Me (CH 2) 2 H CH} 2 N (Et) 2 6-MeSO 2 -3-Pyr O 47- 19 Me (CH 2) 2 H CH 2 N (Et) 2 6-EtSO 2 -3-Pyr O 47 _{- 20 Me (CH 2) 2} H CH 2 N (Et) 2 6-iPrSO 2 -3-Pyr O 47- 21 Me (CH 2) 2 H CH 2 N (Et) 2 6-Bz-3-Pyr O _{47- 22 Me (CH 2) 2} H CH 2 N (Et) 2 6-PhO-3-Pyr O 47- 23 Me (CH 2) 2 H CH 2 N (Et) 2 6-PhS-3-Pyr O 47- 24 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 6-PhSO ₂ -3-Pyr O 47-25 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 2-Quin O 47- 26 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4-MeO-Ph O 47- 27 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4-EtO-Ph O 47- 28 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4-iPrO-Ph O 47- 29 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4-MeS-Ph O 47-30 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4-EtS-Ph O 47- 31 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4-iPrS-Ph O 47- 32 Me (CH ₂ ) ₂ H CH ₂ N (Et ) ₂ 4-MeSO ₂ -Ph O 47- 33 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4-EtSO ₂ -Ph O 47- 34 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4-iPrSO ₂ -Ph O 47- 35 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4- (Pyr-2) Ph O 47- 36 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4- (Pyr-3) Ph O 47- 37 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 4- (Pyr-4) Ph O 47- 38 Me (CH ₂ ) ₂ H CH ₂ N (Et) ₂ 3-Ph-6-Pyr O ──────────────────────────────────.

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[Table 48] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 48- 1 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 4-Et-Ph O 48- 2 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 4-iPr-Ph O 48- 3 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 3-Ph-Ph O 48-4 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 4-Ph-Ph O 48-5 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 3-Pyr O 48-6 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 5-Me-3-Pyr O 48-7 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 5-Et-3-Pyr O 48- 8 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 5-Ph-3-Pyr O 48- 9 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-Me-3-Pyr O 48-10 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-Et-3-Pyr O 48-11 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-Ph-3-Pyr O 48-12 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-MeO-3-Pyr O 48- 13 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-EtO-3-Pyr O 48- 14 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-iPrO -3-Pyr O 48-15 Me (CH ₂ ) ₂ H CH ₂ N ( Me) (Ph) 6-MeS-3-Pyr O 48-16 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-EtS-3-Pyr O 48-17 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-iPrS-3-Pyr O 48-18 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-MeSO ₂ -3-Pyr O 48-19 Me ( CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-EtSO ₂ -3-Pyr O 48-20 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-iPrSO ₂ -3-Pyr O 48-21 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-Bz-3-Pyr O 48-22 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-PhO -3-Pyr O 48-23 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 6-PhS-3-Pyr O 48-24 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph ) 6-PhSO ₂ -3-Pyr O 48-25 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 2-Quin O 48- 26 Me (CH ₂ ) ₂ H CH ₂ N (Me) ( Ph) 4-MeO-Ph O 48- 27 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 4-EtO-Ph O 48- 28 Me (CH ₂ ) ₂ H CH ₂ N (Me) ( Ph) 4-iPrO-Ph O 48- 29 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 4-MeS-Ph O 48-30 Me (CH ₂ ) ₂ H CH ₂ N (Me) ( Ph) 4-EtS-Ph O 48- 31 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 4-iPrS-Ph O 48- 32 Me (CH ₂ ) ₂ H CH ₂ N (Me) ( Ph) 4-MeSO ₂ -Ph O 48- 33 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 4-EtSO ₂ -Ph O 48- 34 Me (CH ₂ ) ₂ H CH ₂ N (Me ) (Ph) 4-iPrSO ₂ -Ph O 48- 35 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 4- (Pyr-2) Ph O 48- 36 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 4- (Pyr-3) Ph O 48- 37 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 4- (Pyr-4) Ph O 48- 38 Me (CH ₂ ) ₂ H CH ₂ N (Me) (Ph) 3 -Ph-6-Pyr O ──────────────────────────────────.

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[Table 49] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 49- 1 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 4-Et-Ph O 49- 2 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 4-iPr-Ph O 49- 3 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 3-Ph-Ph O 49-4 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 4-Ph-Ph O 49-5 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 3-Pyr O 49-6 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 5-Me-3-Pyr O 49-7 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 5-Et-3-Pyr O 49-8 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 5-Ph-3-Pyr O 49- 9 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-Me-3-Pyr O 49-10 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-Et-3-Pyr O 49-11 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-Ph-3-Pyr O 49-12 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-MeO-3-Pyr O 49- 13 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-EtO-3-Pyr O 49- 14 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-iPrO -3-Pyr O 49- 15 Me (CH ₂ ) ₂ H CH ₂ N ( Et) (Ph) 6-MeS-3-Pyr O 49-16 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-EtS-3-Pyr O 49-17 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-iPrS-3-Pyr O 49-18 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-MeSO ₂ -3-Pyr O 49-19 Me ( CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-EtSO ₂ -3-Pyr O 49-20 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-iPrSO ₂ -3-Pyr O 49- 21 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-Bz-3-Pyr O 49- 22 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-PhO -3-Pyr O 49-23 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 6-PhS-3-Pyr O 49-24 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph ) 6-PhSO ₂ -3-Pyr O 49-25 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 2-Quin O 49- 26 Me (CH ₂ ) ₂ H CH ₂ N (Et) ( Ph) 4-MeO-Ph O 49- 27 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 4-EtO-Ph O 49- 28 Me (CH ₂ ) ₂ H CH ₂ N (Et) ( Ph) 4-iPrO-Ph O 49- 29 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 4-MeS-Ph O 49-30 Me (CH ₂ ) ₂ H CH ₂ N (Et) ( Ph) 4-EtS-Ph O 49- 31 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 4-iPrS-Ph O 49- 32 Me (CH ₂ ) ₂ H CH ₂ N (Et) ( Ph) 4-MeSO ₂ -Ph O 49- 33 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 4-EtSO ₂ -Ph O 49- 34 Me (CH ₂ ) ₂ H CH ₂ N (Et ) (Ph) 4-iPrSO ₂ -Ph O 49- 35 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 4- (Pyr-2) Ph O 49- 36 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 4- (Pyr-3) Ph O 49- 37 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 4- (Pyr-4) Ph O 49- 38 Me (CH ₂ ) ₂ H CH ₂ N (Et) (Ph) 3 -Ph-6-Pyr O ──────────────────────────────────.

[0180]

[Table 50] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 50- 1 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 4-Et-Ph O 50- 2 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 4-iPr-Ph O 50- 3 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 3-Ph- _{Ph O 50- 4 Me (CH 2} ) 2 H CH 2 1-Pyrr 4-Ph-Ph O 50- 5 Me (CH 2) 2 H CH 2 1-Pyrr 3-Pyr O 50- 6 Me (CH 2) ₂ H CH ₂ 1-Pyrr 5-Me-3-Pyr O 50- 7 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 5-Et-3-Pyr O 50- 8 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 5-Ph-3 -Pyr O 50- 9 Me (CH 2) 2 H CH 2 1-Pyrr 6-Me-3-Pyr O 50- 10 Me (CH 2) 2 H CH 2 1-Pyrr 6 -Et-3-Pyr O 50- 11 Me (CH 2) 2 H CH 2 1-Pyrr 6-Ph-3-Pyr O 50- 12 Me (CH 2) 2 H CH 2 1-Pyrr 6-MeO-3 _{-Pyr O 50- 13 Me (CH 2} ) 2 H CH 2 1-Pyrr 6-EtO-3-Pyr O 50- 14 Me (CH 2) 2 H CH 2 1-Pyrr 6-iPrO-3-Pyr O 50 -15 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 6-MeS-3-Pyr O 50-16 Me (CH ₂ ) ₂ H C _{H 2 1-Pyrr 6-EtS} -3-Pyr O 50- 17 Me (CH 2) 2 H CH 2 1-Pyrr 6-iPrS-3-Pyr O 50- 18 Me (CH 2) 2 H CH 2 1- _{Pyrr 6-MeSO 2 -3-Pyr} O 50- 19 Me (CH 2) 2 H CH 2 1-Pyrr 6-EtSO 2 -3-Pyr O 50- 20 Me (CH 2) 2 H CH 2 1-Pyrr 6 _{-iPrSO 2 -3-Pyr O 50- 21} Me (CH 2) 2 H CH 2 1-Pyrr 6-Bz-3-Pyr O 50- 22 Me (CH 2) 2 H CH 2 1-Pyrr 6-PhO- 3-Pyr O 50- 23 Me ( CH 2) 2 H CH 2 1-Pyrr 6-PhS-3-Pyr O 50- 24 Me (CH 2) 2 H CH 2 1-Pyrr 6-PhSO 2 -3-Pyr _{O 50- 25 Me (CH 2)} 2 H CH 2 1-Pyrr 2-Quin O 50- 26 Me (CH 2) 2 H CH 2 1-Pyrr 4-MeO-Ph O 50- 27 Me (CH 2) 2 H CH ₂ 1-Pyrr 4-EtO-Ph O 50- 28 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 4-iPrO-Ph O 50- 29 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 4- MeS-Ph O 50- 30 Me ( CH 2) 2 H CH 2 1-Pyrr 4-EtS-Ph O 50- 31 Me (CH 2) 2 H CH 2 1-Pyrr 4-iPrS-Ph O 50- 32 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 4-MeSO ₂ -Ph O 50- 33 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 4-EtSO ₂ -Ph O 50- 34 Me (CH ₂ ) ₂ H _{CH 2 1-Pyrr 4-iPrSO} 2 -Ph O 50- 35 Me (CH 2) 2 H CH 2 1-Pyrr 4- (Pyr-2) Ph O 50- 36 Me (CH 2) 2 H CH 2 1- Pyrr 4- (Pyr-3) Ph O 50- 37 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 4- (Pyr-4) Ph O 50- 38 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrr 3-Ph-6-Pyr O ────────── ────────────────────────.

[0181]

[Table 51] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 51-1 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrd 4-Et-Ph O 51- 2 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrd 4-iPr-Ph O 51- 3 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrd 3-Ph- _{Ph O 51- 4 Me (CH 2} ) 2 H CH 2 1-Pyrd 4-Ph-Ph O 51- 5 Me (CH 2) 2 H CH 2 1-Pyrd 3-Pyr O 51- 6 Me (CH 2) ₂ H CH ₂ 1-Pyrd 5-Me-3-Pyr O 51-7 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrd 5-Et-3-Pyr O 51-8 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrd 5-Ph-3 -Pyr O 51- 9 Me (CH 2) 2 H CH 2 1-Pyrd 6-Me-3-Pyr O 51- 10 Me (CH 2) 2 H CH 2 1-Pyrd 6 -Et-3-Pyr O 51- 11 Me (CH 2) 2 H CH 2 1-Pyrd 6-Ph-3-Pyr O 51- 12 Me (CH 2) 2 H CH 2 1-Pyrd 6-MeO-3 _{-Pyr O 51- 13 Me (CH 2} ) 2 H CH 2 1-Pyrd 6-EtO-3-Pyr O 51- 14 Me (CH 2) 2 H CH 2 1-Pyrd 6-iPrO-3-Pyr O 51 -15 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrd 6-MeS-3-Pyr O 51-16 Me (CH ₂ ) ₂ H C _{H 2 1-Pyrd 6-EtS} -3-Pyr O 51- 17 Me (CH 2) 2 H CH 2 1-Pyrd 6-iPrS-3-Pyr O 51- 18 Me (CH 2) 2 H CH 2 1- _{Pyrd 6-MeSO 2 -3-Pyr} O 51- 19 Me (CH 2) 2 H CH 2 1-Pyrd 6-EtSO 2 -3-Pyr O 51- 20 Me (CH 2) 2 H CH 2 1-Pyrd 6 _{-iPrSO 2 -3-Pyr O 51- 21} Me (CH 2) 2 H CH 2 1-Pyrd 6-Bz-3-Pyr O 51- 22 Me (CH 2) 2 H CH 2 1-Pyrd 6-PhO- 3-Pyr O 51- 23 Me ( CH 2) 2 H CH 2 1-Pyrd 6-PhS-3-Pyr O 51- 24 Me (CH 2) 2 H CH 2 1-Pyrd 6-PhSO 2 -3-Pyr _{O 51- 25 Me (CH 2)} 2 H CH 2 1-Pyrd 2-Quin O 51- 26 Me (CH 2) 2 H CH 2 1-Pyrd 4-MeO-Ph O 51- 27 Me (CH 2) 2 _{H CH 2 1-Pyrd 4-} EtO-Ph O 51- 28 Me (CH 2) 2 H CH 2 1-Pyrd 4-iPrO-Ph O 51- 29 Me (CH 2) 2 H CH 2 1-Pyrd 4- MeS-Ph O 51- 30 Me ( CH 2) 2 H CH 2 1-Pyrd 4-EtS-Ph O 51- 31 Me (CH 2) 2 H CH 2 1-Pyrd 4-iPrS-Ph O 51- 32 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrd 4-MeSO ₂ -Ph O 51- 33 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrd 4-EtSO ₂ -Ph O 51- 34 Me (CH ₂ ) ₂ H _{CH 2 1-Pyrd 4-iPrSO} 2 -Ph O 51- 35 Me (CH 2) 2 H CH 2 1-Pyrd 4- (Pyr-2) Ph O 51- 36 Me (CH 2) 2 H CH 2 1- Pyrd 4- (Pyr-3) Ph O 51- 37 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrd 4- (Pyr-4) Ph O 51- 38 Me (CH ₂ ) ₂ H CH ₂ 1-Pyrd 3-Ph-6-Pyr O ────────── ────────────────────────.

[0182]

[Table 52] Example R ¹ R ² R ³ ZW X Y Compound number ──────────────────────────────────── 52- 1 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 4-Et-Ph O 52- 2 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 4-iPr-Ph O 52- 3 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 3-Ph- _{Ph O 52- 4 Me (CH 2} ) 2 H CH 2 1-Imid 4-Ph-Ph O 52- 5 Me (CH 2) 2 H CH 2 1-Imid 3-Pyr O 52- 6 Me (CH 2) ₂ H CH ₂ 1-Imid 5-Me-3-Pyr O 52- 7 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 5-Et-3-Pyr O 52- 8 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 5-Ph-3 -Pyr O 52- 9 Me (CH 2) 2 H CH 2 1-Imid 6-Me-3-Pyr O 52- 10 Me (CH 2) 2 H CH 2 1-Imid 6 -Et-3-Pyr O 52- 11 Me (CH 2) 2 H CH 2 1-Imid 6-Ph-3-Pyr O 52- 12 Me (CH 2) 2 H CH 2 1-Imid 6-MeO-3 _{-Pyr O 52- 13 Me (CH 2} ) 2 H CH 2 1-Imid 6-EtO-3-Pyr O 52- 14 Me (CH 2) 2 H CH 2 1-Imid 6-iPrO-3-Pyr O 52 -15 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 6-MeS-3-Pyr O 52-16 Me (CH ₂ ) ₂ H C H ₂ 1-Imid 6-EtS-3-Pyr O 52-17 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 6-iPrS-3-Pyr O 52-18 Me (CH ₂ ) ₂ H CH ₂ 1- _{Imid 6-MeSO 2 -3-Pyr} O 52- 19 Me (CH 2) 2 H CH 2 1-Imid 6-EtSO 2 -3-Pyr O 52- 20 Me (CH 2) 2 H CH 2 1-Imid 6 _{-iPrSO 2 -3-Pyr O 52- 21} Me (CH 2) 2 H CH 2 1-Imid 6-Bz-3-Pyr O 52- 22 Me (CH 2) 2 H CH 2 1-Imid 6-PhO- 3-Pyr O 52- 23 Me ( CH 2) 2 H CH 2 1-Imid 6-PhS-3-Pyr O 52- 24 Me (CH 2) 2 H CH 2 1-Imid 6-PhSO 2 -3-Pyr _{O 52- 25 Me (CH 2)} 2 H CH 2 1-Imid 2-Quin O 52- 26 Me (CH 2) 2 H CH 2 1-Imid 4-MeO-Ph O 52- 27 Me (CH 2) 2 H CH ₂ 1-Imid 4-EtO-Ph O 52- 28 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 4-iPrO-Ph O 52- 29 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 4- MeS-Ph O 52- 30 Me ( CH 2) 2 H CH 2 1-Imid 4-EtS-Ph O 52- 31 Me (CH 2) 2 H CH 2 1-Imid 4-iPrS-Ph O 52- 32 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 4-MeSO ₂ -Ph O 52- 33 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 4-EtSO ₂ -Ph O 52- 34 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 4-iPrSO ₂ -Ph O 52- 35 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 4- (Pyr-2) Ph O 52- 36 Me (CH ₂ ) ₂ H CH ₂ 1- Imid 4- (Pyr-3) Ph O 52- 37 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 4- (Pyr-4) Ph O 52- 38 Me (CH ₂ ) ₂ H CH ₂ 1-Imid 3-Ph-6-Pyr O ────────── ────────────────────────.

[0183]

[Table 53] Example R ¹ R ² R ³ ZW X Y Compound number ──────────────────────────────────── 53-1 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 4-Et-Ph O 53- 2 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 4-iPr-Ph O 53- 3 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 3-Ph- _{Ph O 53- 4 Me (CH 2} ) 2 H CH 2 1-Pip 4-Ph-Ph O 53- 5 Me (CH 2) 2 H CH 2 1-Pip 3-Pyr O 53- 6 Me (CH 2) ₂ H CH ₂ 1-Pip 5-Me-3-Pyr O 53- 7 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 5-Et-3-Pyr O 53- 8 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 5-Ph-3 -Pyr O 53- 9 Me (CH 2) 2 H CH 2 1-Pip 6-Me-3-Pyr O 53- 10 Me (CH 2) 2 H CH 2 1-Pip 6 -Et-3-Pyr O 53- 11 Me (CH 2) 2 H CH 2 1-Pip 6-Ph-3-Pyr O 53- 12 Me (CH 2) 2 H CH 2 1-Pip 6-MeO-3 _{-Pyr O 53- 13 Me (CH 2} ) 2 H CH 2 1-Pip 6-EtO-3-Pyr O 53- 14 Me (CH 2) 2 H CH 2 1-Pip 6-iPrO-3-Pyr O 53 _{- 15 Me (CH 2) 2} H CH 2 1-Pip 6-MeS-3-Pyr O 53- 16 Me (CH 2) 2 H CH 2 1-Pip 6-EtS -3-Pyr O 53- 17 Me ( CH 2) 2 H CH 2 1-Pip 6-iPrS-3-Pyr O 53- 18 Me (CH 2) 2 H CH 2 1-Pip 6-MeSO 2 -3- _{Pyr O 53- 19 Me (CH 2} ) 2 H CH 2 1-Pip 6-EtSO 2 -3-Pyr O 53- 20 Me (CH 2) 2 H CH 2 1-Pip 6-iPrSO 2 -3-Pyr O 53- 21 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 6-Bz-3-Pyr O 53- 22 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 6-PhO-3-Pyr O 53- 23 Me _{(CH 2) 2 H CH 2} 1-Pip 6-PhS-3-Pyr O 53- 24 Me (CH 2) 2 H CH 2 1-Pip 6-PhSO 2 -3-Pyr O 53- 25 Me (CH 2 _{) 2 H CH 2 1-Pip} 2-Quin O 53- 26 Me (CH 2) 2 H CH 2 1-Pip 4-MeO-Ph O 53- 27 Me (CH 2) 2 H CH 2 1-Pip 4- EtO-Ph O 53- 28 Me ( CH 2) 2 H CH 2 1-Pip 4-iPrO-Ph O 53- 29 Me (CH 2) 2 H CH 2 1-Pip 4-MeS-Ph O 53- 30 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 4-EtS-Ph O 53- 31 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 4-iPrS-Ph O 53- 32 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 4-MeSO ₂ -Ph O 53- 33 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 4-EtSO ₂ -Ph O 53- 34 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 4-iPrSO _{2 -Ph O 53- 35 Me (CH} 2) 2 H CH 2 1-Pip 4- (Pyr-2) Ph O 53- 36 Me (CH 2) 2 H CH 2 1-Pip 4- (Pyr-3) Ph O 53- 37 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 4- (Pyr-4) Ph O 53- 38 Me (CH ₂ ) ₂ H CH ₂ 1-Pip 3-Ph-6-Pyr O ───────────────────────────── ─────.

[0184]

[Table 54] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 54- 1 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 4-Et-Ph O 54- 2 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 4-iPr-Ph O 54- 3 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 3-Ph- _{Ph O 54- 4 Me (CH 2} ) 2 H CH 2 1-Mor 4-Ph-Ph O 54- 5 Me (CH 2) 2 H CH 2 1-Mor 3-Pyr O 54- 6 Me (CH 2) ₂ H CH ₂ 1-Mor 5-Me-3-Pyr O 54- 7 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 5-Et-3-Pyr O 54- 8 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 5-Ph-3 -Pyr O 54- 9 Me (CH 2) 2 H CH 2 1-Mor 6-Me-3-Pyr O 54- 10 Me (CH 2) 2 H CH 2 1-Mor 6 -Et-3-Pyr O 54- 11 Me (CH 2) 2 H CH 2 1-Mor 6-Ph-3-Pyr O 54- 12 Me (CH 2) 2 H CH 2 1-Mor 6-MeO-3 _{-Pyr O 54- 13 Me (CH 2} ) 2 H CH 2 1-Mor 6-EtO-3-Pyr O 54- 14 Me (CH 2) 2 H CH 2 1-Mor 6-iPrO-3-Pyr O 54 _{- 15 Me (CH 2) 2} H CH 2 1-Mor 6-MeS-3-Pyr O 54- 16 Me (CH 2) 2 H CH 2 1-Mor 6-EtS -3-Pyr O 54- 17 Me ( CH 2) 2 H CH 2 1-Mor 6-iPrS-3-Pyr O 54- 18 Me (CH 2) 2 H CH 2 1-Mor 6-MeSO 2 -3- _{Pyr O 54- 19 Me (CH 2} ) 2 H CH 2 1-Mor 6-EtSO 2 -3-Pyr O 54- 20 Me (CH 2) 2 H CH 2 1-Mor 6-iPrSO 2 -3-Pyr O 54- 21 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 6-Bz-3-Pyr O 54- 22 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 6-PhO-3-Pyr O 54- 23 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 6-PhS-3-Pyr O 54-24 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 6-PhSO ₂ -3-Pyr O 54-25 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 2-Quin O 54- 26 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 4-MeO-Ph O 54- 27 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 4- EtO-Ph O 54- 28 Me ( CH 2) 2 H CH 2 1-Mor 4-iPrO-Ph O 54- 29 Me (CH 2) 2 H CH 2 1-Mor 4-MeS-Ph O 54- 30 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 4-EtS-Ph O 54- 31 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 4-iPrS-Ph O 54- 32 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 4-MeSO ₂ -Ph O 54- 33 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 4-EtSO ₂ -Ph O 54- 34 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 4-iPrSO _{2 -Ph O 54- 35 Me (CH} 2) 2 H CH 2 1-Mor 4- (Pyr-2) Ph O 54- 36 Me (CH 2) 2 H CH 2 1-Mor 4- (Pyr-3) Ph O 54- 37 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 4- (Pyr-4) Ph O 54- 38 Me (CH ₂ ) ₂ H CH ₂ 1-Mor 3-Ph-6-Pyr O ───────────────────────────── ─────.

[0185]

[Table 55] Example R ¹ R ² R ³ ZW X Y Compound number ──────────────────────────────────── 55- 1 Me (CH ₂ ) ₂ H CH ₂ OH 4-Et-Ph O 55- 2 Me (CH ₂ ) ₂ H CH ₂ OH 4-iPr-Ph O 55- 3 Me (CH ₂ ) ₂ H CH ₂ OH 3-Ph-Ph O 55- 4 Me (CH ₂ ) ₂ H CH ₂ OH 4-Ph-Ph O 55-5 Me (CH ₂ ) ₂ H CH ₂ OH 3-Pyr O 55-6 Me (CH ₂ ) ₂ H CH ₂ OH 5-Me-3 -Pyr O 55- 7 Me (CH ₂ ) ₂ H CH ₂ OH 5-Et-3-Pyr O 55- 8 Me (CH ₂ ) ₂ H CH ₂ OH 5-Ph-3-Pyr O 55- 9 Me ( CH ₂ ) ₂ H CH ₂ OH 6-Me-3-Pyr O 55-10 Me (CH ₂ ) ₂ H CH ₂ OH 6-Et-3-Pyr O 55- 11 Me (CH ₂ ) ₂ H CH ₂ OH 6-Ph-3-Pyr O 55-12 Me (CH ₂ ) ₂ H CH ₂ OH 6-MeO-3-Pyr O 55- 13 Me (CH ₂ ) ₂ H CH ₂ OH 6-EtO-3-Pyr O 55- 14 Me (CH ₂ ) ₂ H CH ₂ OH 6-iPrO-3-Pyr O 55- 15 Me (CH ₂ ) ₂ H CH ₂ OH 6-MeS-3-Pyr O 55- 16 Me (CH ₂ ) ₂ H CH ₂ OH 6-EtS-3-Pyr O 55-17 Me (CH ₂ ) ₂ H CH ₂ OH 6-iPrS-3- Pyr O 55- 18 Me (CH ₂ ) ₂ H CH ₂ OH 6-MeSO ₂ -3-Pyr O 55- 19 Me (CH ₂ ) ₂ H CH ₂ OH 6-EtSO ₂ -3-Pyr O 55- 20 Me (CH ₂ ) ₂ H CH ₂ OH 6-iPrSO ₂ -3-Pyr O 55- 21 Me (CH ₂ ) ₂ H CH ₂ OH 6-Bz-3-Pyr O 55- 22 Me (CH ₂ ) ₂ H CH ₂ OH 6-PhO-3-Pyr O 55- 23 Me (CH ₂ ) ₂ H CH ₂ OH 6-PhS-3-Pyr O 55- 24 Me (CH ₂ ) ₂ H CH ₂ OH 6-PhSO ₂ -3 -Pyr O 55- 25 Me (CH ₂ ) ₂ H CH ₂ OH 2-Quin O 55- 26 Me (CH ₂ ) ₂ H CH ₂ OH 4-MeO-Ph O 55- 27 Me (CH ₂ ) ₂ H CH ₂ OH 4-EtO-Ph O 55- 28 Me (CH ₂ ) ₂ H CH ₂ OH 4-iPrO-Ph O 55- 29 Me (CH ₂ ) ₂ H CH ₂ OH 4-MeS-Ph O 55-30 Me (CH ₂ ) ₂ H CH ₂ OH 4-EtS-Ph O 55- 31 Me (CH ₂ ) ₂ H CH ₂ OH 4-iPrS-Ph O 55- 32 Me (CH ₂ ) ₂ H CH ₂ OH 4-MeSO ₂ -Ph O 55- 33 Me (CH ₂ ) ₂ H CH ₂ OH 4-EtSO ₂ -Ph O 55- 34 Me (CH ₂ ) ₂ H CH ₂ OH 4-iPrSO ₂ -Ph O 55- 35 Me (CH ₂ ) ₂ H CH ₂ OH 4- (Pyr-2) Ph O 55- 36 Me (CH ₂ ) ₂ H CH ₂ OH 4- (Pyr-3) Ph O 55- 37 Me (CH ₂ ) ₂ H CH ₂ OH 4- (Pyr-4) Ph O 55- 38 Me (CH ₂ ) ₂ H CH ₂ OH 3-Ph-6-Pyr O ─────────────────── ───── ──────────.

[0186]

[Table 56] Example R ¹ R ² R ³ Z W X Y compound number ──────────────────────────────────── 56- 1 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Et-Ph O 56- 2 Me (CH ₂ ) ₂ H CH ₂ OMe 4-iPr-Ph O 56- 3 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Ph-Ph O 56- 4 Me (CH ₂ ) ₂ H CH ₂ OMe 4-Ph-Ph O 56- 5 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Pyr O 56- 6 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Me-3 -Pyr O 56- 7 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Et-3-Pyr O 56- 8 Me (CH ₂ ) ₂ H CH ₂ OMe 5-Ph-3-Pyr O 56- 9 Me ( CH ₂ ) ₂ H CH ₂ OMe 6-Me-3-Pyr O 56-10 Me (CH ₂ ) ₂ H CH ₂ OMe 6-Et-3-Pyr O 56- 11 Me (CH ₂ ) ₂ H CH ₂ OMe 6-Ph-3-Pyr O 56- 12 Me (CH ₂ ) ₂ H CH ₂ OMe 6-MeO-3-Pyr O 56- 13 Me (CH ₂ ) ₂ H CH ₂ OMe 6-EtO-3-Pyr O 56- 14 Me (CH ₂ ) ₂ H CH ₂ OMe 6-iPrO-3-Pyr O 56- 15 Me (CH ₂ ) ₂ H CH ₂ OMe 6-MeS-3-Pyr O 56- 16 Me (CH ₂ ) ₂ H CH ₂ OMe 6-EtS-3-Pyr O 56-17 Me (CH ₂ ) ₂ H C H ₂ OMe 6-iPrS-3-Pyr O 56-18 Me (CH ₂ ) ₂ H CH ₂ OMe 6-MeSO ₂ -3-Pyr O 56-19 Me (CH ₂ ) ₂ H CH ₂ OMe 6-EtSO ₂ -3-Pyr O 56- 20 Me (CH ₂ ) ₂ H CH ₂ OMe 6-iPrSO ₂ -3-Pyr O 56- 21 Me (CH ₂ ) ₂ H CH ₂ OMe 6-Bz-3-Pyr O 56- 22 Me (CH ₂ ) ₂ H CH ₂ OMe 6-PhO-3-Pyr O 56- 23 Me (CH ₂ ) ₂ H CH ₂ OMe 6-PhS-3-Pyr O 56- 24 Me (CH ₂ ) ₂ H CH ₂ OMe 6-PhSO ₂ -3-Pyr O 56- 25 Me (CH ₂ ) ₂ H CH ₂ OMe 2-Quin O 56- 26 Me (CH ₂ ) ₂ H CH ₂ OMe 4-MeO-Ph O 56- 27 Me (CH ₂ ) ₂ H CH ₂ OMe 4-EtO-Ph O 56- 28 Me (CH ₂ ) ₂ H CH ₂ OMe 4-iPrO-Ph O 56- 29 Me (CH ₂ ) ₂ H CH ₂ OMe 4 -MeS-Ph O 56- 30 Me (CH ₂ ) ₂ H CH ₂ OMe 4-EtS-Ph O 56- 31 Me (CH ₂ ) ₂ H CH ₂ OMe 4-iPrS-Ph O 56- 32 Me (CH ₂ ) ₂ H CH ₂ OMe 4-MeSO ₂ -Ph O 56-33 Me (CH ₂ ) ₂ H CH ₂ OMe 4-EtSO ₂ -Ph O 56- 34 Me (CH ₂ ) ₂ H CH ₂ OMe 4-iPrSO ₂ -Ph O 56- 35 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Pyr-2) Ph O 56- 36 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Pyr-3) Ph O 56- 37 Me (CH ₂ ) ₂ H CH ₂ OMe 4- (Pyr-4) Ph O 56- 38 Me (CH ₂ ) ₂ H CH ₂ OMe 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0187]

[Table 57] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 57- 1 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Et-Ph O 57- 2 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPr-Ph O 57- 3 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-Ph O 57- 4 Me (CH ₂ ) ₂ H CH ₂ OEt 4-Ph-Ph O 57-5 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Pyr O 57-6 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Me-3 -Pyr O 57- 7 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Et-3-Pyr O 57- 8 Me (CH ₂ ) ₂ H CH ₂ OEt 5-Ph-3-Pyr O 57- 9 Me ( CH ₂ ) ₂ H CH ₂ OEt 6-Me-3-Pyr O 57-10 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Et-3-Pyr O 57-11 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Ph-3-Pyr O 57- 12 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeO-3-Pyr O 57- 13 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtO-3-Pyr O 57- 14 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrO-3-Pyr O 57- 15 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeS-3-Pyr O 57- 16 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtS-3-Pyr O 57-17 Me (CH ₂ ) ₂ H C H ₂ OEt 6-iPrS-3-Pyr O 57-18 Me (CH ₂ ) ₂ H CH ₂ OEt 6-MeSO ₂ -3-Pyr O 57-19 Me (CH ₂ ) ₂ H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 57- 20 Me (CH ₂ ) ₂ H CH ₂ OEt 6-iPrSO ₂ -3-Pyr O 57- 21 Me (CH ₂ ) ₂ H CH ₂ OEt 6-Bz-3-Pyr O 57- _{22 Me (CH 2) 2 H} CH 2 OEt 6-PhO-3-Pyr O 57- 23 Me (CH 2) 2 H CH 2 OEt 6-PhS-3-Pyr O 57- 24 Me (CH 2) 2 H CH ₂ OEt 6-PhSO ₂ -3-Pyr O 57- 25 Me (CH ₂ ) ₂ H CH ₂ OEt 2-Quin O 57- 26 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeO-Ph O 57- 27 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtO-Ph O 57- 28 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrO-Ph O 57- 29 Me (CH ₂ ) ₂ H CH ₂ OEt 4 -MeS-Ph O 57-30 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtS-Ph O 57- 31 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrS-Ph O 57- 32 Me (CH ₂ ) ₂ H CH ₂ OEt 4-MeSO ₂ -Ph O 57- 33 Me (CH ₂ ) ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 57- 34 Me (CH ₂ ) ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 57- 35 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-2) Ph O 57- 36 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-3) Ph O 57- 37 Me (CH ₂ ) ₂ H CH ₂ OEt 4- (Pyr-4) Ph O 57- 38 Me (CH ₂ ) ₂ H CH ₂ OEt 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0188]

[Table 58] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 58- 1 Me (CH ₂ ) ₂ H CH ₂ OPr 4-Et-Ph O 58- 2 Me (CH ₂ ) ₂ H CH ₂ OPr 4-iPr-Ph O 58- 3 Me (CH ₂ ) ₂ H CH ₂ OPr 3-Ph-Ph O 58- 4 Me (CH ₂ ) ₂ H CH ₂ OPr 4-Ph-Ph O 58-5 Me (CH ₂ ) ₂ H CH ₂ OPr 3-Pyr O 58-6 Me (CH ₂ ) ₂ H CH ₂ OPr 5-Me-3 -Pyr O 58- 7 Me (CH ₂ ) ₂ H CH ₂ OPr 5-Et-3-Pyr O 58- 8 Me (CH ₂ ) ₂ H CH ₂ OPr 5-Ph-3-Pyr O 58- 9 Me ( CH ₂ ) ₂ H CH ₂ OPr 6-Me-3-Pyr O 58-10 Me (CH ₂ ) ₂ H CH ₂ OPr 6-Et-3-Pyr O 58-11 Me (CH ₂ ) ₂ H CH ₂ OPr 6-Ph-3-Pyr O 58-12 Me (CH ₂ ) ₂ H CH ₂ OPr 6-MeO-3-Pyr O 58- 13 Me (CH ₂ ) ₂ H CH ₂ OPr 6-EtO-3-Pyr O 58- 14 Me (CH ₂ ) ₂ H CH ₂ OPr 6-iPrO-3-Pyr O 58- 15 Me (CH ₂ ) ₂ H CH ₂ OPr 6-MeS-3-Pyr O 58- 16 Me (CH ₂ ) ₂ H CH ₂ OPr 6-EtS-3-Pyr O 58-17 Me (CH ₂ ) ₂ H C H ₂ OPr 6-iPrS-3-Pyr O 58-18 Me (CH ₂ ) ₂ H CH ₂ OPr 6-MeSO ₂ -3-Pyr O 58-19 Me (CH ₂ ) ₂ H CH ₂ OPr 6-EtSO ₂ -3-Pyr O 58-20 Me (CH ₂ ) ₂ H CH ₂ OPr 6-iPrSO ₂ -3-Pyr O 58- 21 Me (CH ₂ ) ₂ H CH ₂ OPr 6-Bz-3-Pyr O 58- _{22 Me (CH 2) 2 H} CH 2 OPr 6-PhO-3-Pyr O 58- 23 Me (CH 2) 2 H CH 2 OPr 6-PhS-3-Pyr O 58- 24 Me (CH 2) 2 H CH ₂ OPr 6-PhSO ₂ -3-Pyr O 58- 25 Me (CH ₂ ) ₂ H CH ₂ OPr 2-Quin O 58- 26 Me (CH ₂ ) ₂ H CH ₂ OPr 4-MeO-Ph O 58- 27 Me (CH ₂ ) ₂ H CH ₂ OPr 4-EtO-Ph O 58- 28 Me (CH ₂ ) ₂ H CH ₂ OPr 4-iPrO-Ph O 58- 29 Me (CH ₂ ) ₂ H CH ₂ OPr 4 -MeS-Ph O 58-30 Me (CH ₂ ) ₂ H CH ₂ OPr 4-EtS-Ph O 58-31 Me (CH ₂ ) ₂ H CH ₂ OPr 4-iPrS-Ph O 58-32 Me (CH ₂ ) ₂ H CH ₂ OPr 4-MeSO ₂ -Ph O 58-33 Me (CH ₂ ) ₂ H CH ₂ OPr 4-EtSO ₂ -Ph O 58- 34 Me (CH ₂ ) ₂ H CH ₂ OPr 4-iPrSO ₂ -Ph O 58- 35 Me (CH ₂ ) ₂ H CH ₂ OPr 4- (Pyr-2) Ph O 58- 36 Me (CH ₂ ) ₂ H CH ₂ OPr 4- (Pyr-3) Ph O 58- 37 Me (CH ₂ ) ₂ H CH ₂ OPr 4- (Pyr-4) Ph O 58- 38 Me (CH ₂ ) ₂ H CH ₂ OPr 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0189]

[Table 59] 例 示 Examples R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 59-1 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-Et-Ph O 59- 2 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-iPr-Ph O 59- 3 Me (CH ₂ ) ₂ H CH ₂ OiPr 3-Ph-Ph O 59- 4 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-Ph-Ph O 59- 5 Me (CH ₂ ) ₂ H CH ₂ OiPr 3-Pyr O 59- 6 Me (CH ₂ ) ₂ H CH ₂ OiPr 5-Me-3 -Pyr O 59- 7 Me (CH ₂ ) ₂ H CH ₂ OiPr 5-Et-3-Pyr O 59- 8 Me (CH ₂ ) ₂ H CH ₂ OiPr 5-Ph-3-Pyr O 59- 9 Me ( CH ₂ ) ₂ H CH ₂ OiPr 6-Me-3-Pyr O 59-10 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-Et-3-Pyr O 59- 11 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-Ph-3-Pyr O 59-12 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-MeO-3-Pyr O 59- 13 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-EtO-3-Pyr O 59- 14 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-iPrO-3-Pyr O 59- 15 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-MeS-3-Pyr O 59- 16 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-EtS-3-Pyr O 59-17 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-iPrS-3-Pyr O 59-18 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-MeSO ₂ -3-Pyr O 59-19 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-EtSO ₂ -3-Pyr O 59-20 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-iPrSO ₂ -3-Pyr O 59- 21 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-Bz -3-Pyr O 59- 22 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-PhO-3-Pyr O 59- 23 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-PhS-3-Pyr O 59- 24 Me (CH ₂ ) ₂ H CH ₂ OiPr 6-PhSO ₂ -3-Pyr O 59-25 Me (CH ₂ ) ₂ H CH ₂ OiPr 2-Quin O 59-26 Me (CH ₂ ) ₂ H CH ₂ OiPr 4 -MeO-Ph O 59- 27 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-EtO-Ph O 59- 28 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-iPrO-PhO 59- 29 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-MeS-Ph O 59-30 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-EtS-Ph O 59- 31 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-iPrS-Ph O 59- 32 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-MeSO ₂ -Ph O 59- 33 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-EtSO ₂ -Ph O 59- 34 Me (CH ₂ ) ₂ H CH ₂ OiPr 4-iPrSO ₂ -Ph O 59- 35 Me (CH ₂ ) ₂ H CH ₂ OiPr 4- (Pyr-2) Ph O 59- 36 Me (CH ₂ ) ₂ H CH ₂ OiPr 4- (Pyr- 3) Ph O 59- 37 Me (CH ₂ ) ₂ H CH ₂ OiPr 4- (Pyr-4) Ph O 59- 38 Me (CH ₂ ) ₂ H CH ₂ OiPr 3-Ph-6-Py r O ──────────────────────────────────.

[0190]

[Table 60] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 60- 1 Me (CH ₂ ) ₃ H CH ₂ OMe 4-Et-Ph O 60- 2 Me (CH ₂ ) ₃ H CH ₂ OMe 4-iPr-Ph O 60- 3 Me (CH ₂ ) ₃ H CH ₂ OMe 3-Ph-Ph O 60- 4 Me (CH ₂ ) ₃ H CH ₂ OMe 4-Ph-Ph O 60-5 Me (CH ₂ ) ₃ H CH ₂ OMe 3-Pyr O 60-6 6 Me (CH ₂ ) ₃ H CH ₂ OMe 5-Me-3 -Pyr O 60- 7 Me (CH ₂ ) ₃ H CH ₂ OMe 5-Et-3-Pyr O 60- 8 Me (CH ₂ ) ₃ H CH ₂ OMe 5-Ph-3-Pyr O 60- 9 Me ( CH ₂ ) ₃ H CH ₂ OMe 6-Me-3-Pyr O 60-10 Me (CH ₂ ) ₃ H CH ₂ OMe 6-Et-3-Pyr O 60-11 Me (CH ₂ ) ₃ H CH ₂ OMe 6-Ph-3-Pyr O 60- 12 Me (CH ₂ ) ₃ H CH ₂ OMe 6-MeO-3-Pyr O 60- 13 Me (CH ₂ ) ₃ H CH ₂ OMe 6-EtO-3-Pyr O 60- 14 Me (CH ₂ ) ₃ H CH ₂ OMe 6-iPrO-3-Pyr O 60-15 Me (CH ₂ ) ₃ H CH ₂ OMe 6-MeS-3-Pyr O 60-16 Me (CH ₂ ) ₃ H CH ₂ OMe 6-EtS-3-Pyr O 60-17 Me (CH ₂ ) ₃ H C H ₂ OMe 6-iPrS-3-Pyr O 60-18 Me (CH ₂ ) ₃ H CH ₂ OMe 6-MeSO ₂ -3-Pyr O 60-19 Me (CH ₂ ) ₃ H CH ₂ OMe 6-EtSO ₂ -3-Pyr O 60- 20 Me (CH ₂ ) ₃ H CH ₂ OMe 6-iPrSO ₂ -3-Pyr O 60- 21 Me (CH ₂ ) ₃ H CH ₂ OMe 6-Bz-3-Pyr O 60- _{22 Me (CH 2) 3 H} CH 2 OMe 6-PhO-3-Pyr O 60- 23 Me (CH 2) 3 H CH 2 OMe 6-PhS-3-Pyr O 60- 24 Me (CH 2) 3 H CH ₂ OMe 6-PhSO ₂ -3-Pyr O 60- 25 Me (CH ₂ ) ₃ H CH ₂ OMe 2-Quin O 60- 26 Me (CH ₂ ) ₃ H CH ₂ OMe 4-MeO-Ph O 60- 27 Me (CH ₂ ) ₃ H CH ₂ OMe 4-EtO-Ph O 60-28 Me (CH ₂ ) ₃ H CH ₂ OMe 4-iPrO-Ph O 60-29 Me (CH ₂ ) ₃ H CH ₂ OMe 4 -MeS-Ph O 60-30 Me (CH ₂ ) ₃ H CH ₂ OMe 4-EtS-Ph O 60-31 Me (CH ₂ ) ₃ H CH ₂ OMe 4-iPrS-Ph O 60-32 Me (CH ₂ ) ₃ H CH ₂ OMe 4-MeSO ₂ -Ph O 60- 33 Me (CH ₂ ) ₃ H CH ₂ OMe 4-EtSO ₂ -Ph O 60- 34 Me (CH ₂ ) ₃ H CH ₂ OMe 4-iPrSO ₂ -Ph O 60- 35 Me (CH ₂ ) ₃ H CH ₂ OMe 4- (Pyr-2) Ph O 60- 36 Me (CH ₂ ) ₃ H CH ₂ OMe 4- (Pyr-3) Ph O 60- 37 Me (CH ₂ ) ₃ H CH ₂ OMe 4- (Pyr-4) Ph O 60- 38 Me (CH ₂ ) ₃ H CH ₂ OMe 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0191]

[Table 61] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 61- 1 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Et-Ph O 61- 2 Me (CH ₂ ) ₃ H CH ₂ OEt 4-iPr-Ph O 61- 3 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Ph-Ph O 61- 4 Me (CH ₂ ) ₃ H CH ₂ OEt 4-Ph-Ph O 61-5 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Pyr O 61-6 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Me-3 -Pyr O 61- 7 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Et-3-Pyr O 61- 8 Me (CH ₂ ) ₃ H CH ₂ OEt 5-Ph-3-Pyr O 61- 9 Me ( CH ₂ ) ₃ H CH ₂ OEt 6-Me-3-Pyr O 61-10 Me (CH ₂ ) ₃ H CH ₂ OEt 6-Et-3-Pyr O 61-11 Me (CH ₂ ) ₃ H CH ₂ OEt 6-Ph-3-Pyr O 61-12 Me (CH ₂ ) ₃ H CH ₂ OEt 6-MeO-3-Pyr O 61- 13 Me (CH ₂ ) ₃ H CH ₂ OEt 6-EtO-3-Pyr O 61- 14 Me (CH ₂ ) ₃ H CH ₂ OEt 6-iPrO-3-Pyr O 61-15 Me (CH ₂ ) ₃ H CH ₂ OEt 6-MeS-3-Pyr O 61-16 Me (CH ₂ ) ₃ H CH ₂ OEt 6-EtS-3-Pyr O 61-17 Me (CH ₂ ) ₃ H C H ₂ OEt 6-iPrS-3-Pyr O 61-18 Me (CH ₂ ) ₃ H CH ₂ OEt 6-MeSO ₂ -3-Pyr O 61-19 Me (CH ₂ ) ₃ H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 61-20 Me (CH ₂ ) ₃ H CH ₂ OEt 6-iPrSO ₂ -3-Pyr O 61- 21 Me (CH ₂ ) ₃ H CH ₂ OEt 6-Bz-3-Pyr O 61- _{22 Me (CH 2) 3 H} CH 2 OEt 6-PhO-3-Pyr O 61- 23 Me (CH 2) 3 H CH 2 OEt 6-PhS-3-Pyr O 61- 24 Me (CH 2) 3 H CH ₂ OEt 6-PhSO ₂ -3-Pyr O 61- 25 Me (CH ₂ ) ₃ H CH ₂ OEt 2-Quin O 61- 26 Me (CH ₂ ) ₃ H CH ₂ OEt 4-MeO-Ph O 61- 27 Me (CH ₂ ) ₃ H CH ₂ OEt 4-EtO-Ph O 61-28 Me (CH ₂ ) ₃ H CH ₂ OEt 4-iPrO-Ph O 61-29 Me (CH ₂ ) ₃ H CH ₂ OEt 4 -MeS-Ph O 61-30 Me (CH ₂ ) ₃ H CH ₂ OEt 4-EtS-Ph O 61-31 Me (CH ₂ ) ₃ H CH ₂ OEt 4-iPrS-Ph O 61-32 Me (CH ₂ ) ₃ H CH ₂ OEt 4-MeSO ₂ -Ph O 61-33 Me (CH ₂ ) ₃ H CH ₂ OEt 4-EtSO ₂ -Ph O 61- 34 Me (CH ₂ ) ₃ H CH ₂ OEt 4-iPrSO ₂ -Ph O 61- 35 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Pyr-2) Ph O 61- 36 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Pyr-3) Ph O 61- 37 Me (CH ₂ ) ₃ H CH ₂ OEt 4- (Pyr-4) Ph O 61- 38 Me (CH ₂ ) ₃ H CH ₂ OEt 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0192]

[Table 62] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 62-1 Me (CH ₂ ) ₃ H CH ₂ OPr 4-Et-Ph O 62- 2 Me (CH ₂ ) ₃ H CH ₂ OPr 4-iPr-Ph O 62- 3 Me (CH ₂ ) ₃ H CH ₂ OPr 3-Ph-Ph O 62- 4 Me (CH ₂ ) ₃ H CH ₂ OPr 4-Ph-Ph O 62-5 Me (CH ₂ ) ₃ H CH ₂ OPr 3-Pyr O 62-6 6 Me (CH ₂ ) ₃ H CH ₂ OPr 5-Me-3 -Pyr O 62- 7 Me (CH ₂ ) ₃ H CH ₂ OPr 5-Et-3-Pyr O 62- 8 Me (CH ₂ ) ₃ H CH ₂ OPr 5-Ph-3-Pyr O 62- 9 Me ( CH ₂ ) ₃ H CH ₂ OPr 6-Me-3-Pyr O 62-10 Me (CH ₂ ) ₃ H CH ₂ OPr 6-Et-3-Pyr O 62-11 Me (CH ₂ ) ₃ H CH ₂ OPr 6-Ph-3-Pyr O 62-12 Me (CH ₂ ) ₃ H CH ₂ OPr 6-MeO-3-Pyr O 62- 13 Me (CH ₂ ) ₃ H CH ₂ OPr 6-EtO-3-Pyr O 62- 14 Me (CH ₂ ) ₃ H CH ₂ OPr 6-iPrO-3-Pyr O 62- 15 Me (CH ₂ ) ₃ H CH ₂ OPr 6-MeS-3-Pyr O 62- 16 Me (CH ₂ ) ₃ H CH ₂ OPr 6-EtS-3-Pyr O 62-17 Me (CH ₂ ) ₃ H C H ₂ OPr 6-iPrS-3-Pyr O 62-18 Me (CH ₂ ) ₃ H CH ₂ OPr 6-MeSO ₂ -3-Pyr O 62-19 Me (CH ₂ ) ₃ H CH ₂ OPr 6-EtSO ₂ -3-Pyr O 62-20 Me (CH ₂ ) ₃ H CH ₂ OPr 6-iPrSO ₂ -3-Pyr O 62- 21 Me (CH ₂ ) ₃ H CH ₂ OPr 6-Bz-3-Pyr O 62- _{22 Me (CH 2) 3 H} CH 2 OPr 6-PhO-3-Pyr O 62- 23 Me (CH 2) 3 H CH 2 OPr 6-PhS-3-Pyr O 62- 24 Me (CH 2) 3 H CH ₂ OPr 6-PhSO ₂ -3-Pyr O 62- 25 Me (CH ₂ ) ₃ H CH ₂ OPr 2-Quin O 62- 26 Me (CH ₂ ) ₃ H CH ₂ OPr 4-MeO-Ph O 62- 27 Me (CH ₂ ) ₃ H CH ₂ OPr 4-EtO-Ph O 62- 28 Me (CH ₂ ) ₃ H CH ₂ OPr 4-iPrO-Ph O 62- 29 Me (CH ₂ ) ₃ H CH ₂ OPr 4 -MeS-Ph O 62- 30 Me (CH ₂ ) ₃ H CH ₂ OPr 4-EtS-Ph O 62- 31 Me (CH ₂ ) ₃ H CH ₂ OPr 4-iPrS-Ph O 62- 32 Me (CH ₂ ) ₃ H CH ₂ OPr 4-MeSO ₂ -Ph O 62-33 Me (CH ₂ ) ₃ H CH ₂ OPr 4-EtSO ₂ -Ph O 62- 34 Me (CH ₂ ) ₃ H CH ₂ OPr 4-iPrSO ₂ -Ph O 62- 35 Me (CH ₂ ) ₃ H CH ₂ OPr 4- (Pyr-2) Ph O 62- 36 Me (CH ₂ ) ₃ H CH ₂ OPr 4- (Pyr-3) Ph O 62- 37 Me (CH ₂ ) ₃ H CH ₂ OPr 4- (Pyr-4) Ph O 62- 38 Me (CH ₂ ) ₃ H CH ₂ OPr 3-Ph-6-Pyr O ────────── ─ ──────────────────────.

[0193]

[Table 63] Example R ¹ R ² R ³ ZW X Y Compound number ──────────────────────────────────── 63-1 Me CH (Me) CH ₂ H CH ₂ OEt 4-Et-Ph O 63- 2 Me CH (Me) CH ₂ H CH ₂ OEt 4-iPr-Ph O 63- 3 Me CH (Me) CH ₂ H CH ₂ OEt 3-Ph-Ph O 63 -4 Me CH (Me) CH ₂ H CH ₂ OEt 4-Ph-Ph O 63-5 Me CH (Me) CH ₂ H CH ₂ OEt 3-Pyr O 63-6 Me CH (Me) CH ₂ H CH ₂ OEt 5-Me-3-Pyr O 63- 7 Me CH (Me) CH ₂ H CH ₂ OEt 5-Et-3-Pyr O 63- 8 Me CH (Me) CH ₂ H CH ₂ OEt 5-Ph-3 -Pyr O 63- 9 Me CH (Me) CH ₂ H CH ₂ OEt 6-Me-3-Pyr O 63- 10 Me CH (Me) CH ₂ H CH ₂ OEt 6-Et-3-Pyr O 63-11 Me CH (Me) CH ₂ H CH ₂ OEt 6-Ph-3-Pyr O 63-12 Me CH (Me) CH ₂ H CH ₂ OEt 6-MeO-3-Pyr O 63- 13 Me CH (Me) CH ₂ H CH ₂ OEt 6-EtO-3-Pyr O 63-14 Me CH (Me) CH ₂ H CH ₂ OEt 6-iPrO-3-Pyr O 63-15 Me CH (Me) CH ₂ H CH ₂ OEt 6 -MeS-3-Pyr O 63-16 Me CH (Me) CH ₂ H CH ₂ OEt 6-EtS-3-Pyr O 63-17 Me CH (Me) CH ₂ H CH ₂ OEt 6-iPrS-3-Pyr O 63-18 Me CH (Me) CH ₂ H CH ₂ OEt 6-MeSO ₂ -3-Pyr O 63-19 Me CH (Me) CH ₂ H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 63-20 Me CH (Me) CH ₂ H CH ₂ OEt 6-iPrSO ₂ -3-Pyr O 63- 21 Me CH (Me) CH ₂ H CH ₂ OEt 6-Bz-3-Pyr O 63- 22 Me CH (Me) CH ₂ H CH ₂ OEt 6-PhO-3-Pyr O 63- 23 Me CH (Me) CH ₂ H CH ₂ OEt 6-PhS- 3-Pyr O 63- 24 Me CH (Me) CH ₂ H CH ₂ OEt 6-PhSO ₂ -3-Pyr O 63- 25 Me CH (Me) CH ₂ H CH ₂ OEt 2-Quin O 63- 26 Me CH (Me) CH ₂ H CH ₂ OEt 4-MeO-Ph O 63- 27 Me CH (Me) CH ₂ H CH ₂ OEt 4-EtO-Ph O 63- 28 Me CH (Me) CH ₂ H CH ₂ OEt 4 -iPrO-Ph O 63- 29 Me CH (Me) CH ₂ H CH ₂ OEt 4-MeS-Ph O 63- 30 Me CH (Me) CH ₂ H CH ₂ OEt 4-EtS-Ph O 63- 31 Me CH (Me) CH ₂ H CH ₂ OEt 4-iPrS-Ph O 63- 32 Me CH (Me) CH ₂ H CH ₂ OEt 4-MeSO ₂ -Ph O 63- 33 Me CH (Me) CH ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 63- 34 Me CH (Me) CH ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 63- 35 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Pyr-2) Ph O 63- 36 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Pyr-3) Ph O 63- 37 Me CH (Me) CH ₂ H CH ₂ OEt 4- (Pyr-4) Ph O 63- 38 Me CH (Me) CH ₂ H CH ₂ OEt 3-Ph-6-Py r O ──────────────────────────────────.

[0194]

[Table 64] Example R ¹ R ² R ³ ZW X Y Compound number ──────────────────────────────────── 64- 1 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-Et-Ph O 64- 2 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-iPr-Ph O 64- 3 Me C (Me) ₂ CH ₂ H CH ₂ OEt 3-Ph- Ph O 64- 4 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-Ph-Ph O 64- 5 Me C (Me) ₂ CH ₂ H CH ₂ OEt 3-Pyr O 64- 6 Me C (Me) ₂ CH ₂ H CH ₂ OEt 5-Me-3-Pyr O 64- 7 Me C (Me) ₂ CH ₂ H CH ₂ OEt 5-Et-3-Pyr O 64- 8 Me C (Me) ₂ CH ₂ H CH ₂ OEt 5-Ph-3-Pyr O 64- 9 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-Me-3-Pyr O 64- 10 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6 -Et-3-Pyr O 64- 11 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-Ph-3-Pyr O 64- 12 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-MeO-3 -Pyr O 64- 13 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-EtO-3-Pyr O 64- 14 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-iPrO-3-Pyr O 64 -15 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-MeS-3-Pyr O 64- 16 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-EtS-3-Pyr O 64-17 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-iPrS-3-Pyr O 64- 18 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-MeSO ₂ -3-Pyr O 64- 19 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 64- 20 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6- iPrSO ₂ -3-Pyr O 64-21 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-Bz-3-Pyr O 64-22 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-PhO-3 -Pyr O 64- 23 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-PhS-3-Pyr O 64- 24 Me C (Me) ₂ CH ₂ H CH ₂ OEt 6-PhSO ₂ -3-Pyr O 64- 25 Me C (Me) ₂ CH ₂ H CH ₂ OEt 2-Quin O 64- 26 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-MeO-Ph O 64-27 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-EtO-Ph O 64-28 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-iPrO-Ph O 64-29 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-MeS -Ph O 64- 30 Me C (Me ) 2 CH 2 H CH 2 OEt 4-EtS-Ph O 64- 31 Me C (Me) 2 CH 2 H CH 2 OEt 4-iPrS-Ph O 64- 32 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-MeSO ₂ -Ph O 64-33 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-EtSO ₂ -Ph O 64-34 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4-iPrSO ₂ -Ph O 64-35 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4- (Pyr-2) Ph O 64-36 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4- (Pyr-3) Ph O 64-37 Me C (Me) ₂ CH ₂ H CH ₂ OEt 4- (Pyr-4) Ph O 64-38 Me C (Me) ₂ CH ₂ H CH ₂ OEt 3-Ph-6-Pyr O ─────────── ───────────────────────.

[0195]

[Table 65] Example R ¹ R ² R ³ ZW X Y Compound number ──────────────────────────────────── 65- 1 Me CH ₂ CH (Me) H CH ₂ OEt 4-Et-Ph O 65- 2 Me CH ₂ CH (Me) H CH ₂ OEt 4-iPr-Ph O 65- 3 Me CH ₂ CH (Me) H CH ₂ OEt 3-Ph-Ph O 65 -4 Me CH ₂ CH (Me) H CH ₂ OEt 4-Ph-Ph O 65-5 Me CH ₂ CH (Me) H CH ₂ OEt 3-Pyr O 65-6 Me CH ₂ CH (Me) H CH ₂ OEt 5-Me-3-Pyr O 65- 7 Me CH ₂ CH (Me) H CH ₂ OEt 5-Et-3-Pyr O 65- 8 Me CH ₂ CH (Me) H CH ₂ OEt 5-Ph-3 -Pyr O 65- 9 Me CH ₂ CH (Me) H CH ₂ OEt 6-Me-3-Pyr O 65- 10 Me CH ₂ CH (Me) H CH ₂ OEt 6-Et-3-Pyr O 65-11 Me CH ₂ CH (Me) H CH ₂ OEt 6-Ph-3-Pyr O 65-12 Me CH ₂ CH (Me) H CH ₂ OEt 6-MeO-3-Pyr O 65- 13 Me CH ₂ CH (Me ) H CH ₂ OEt 6-EtO-3-Pyr O 65- 14 Me CH ₂ CH (Me) H CH ₂ OEt 6-iPrO-3-Pyr O 65- 15 Me CH ₂ CH (Me) H CH ₂ OEt 6 -MeS-3-Pyr O 65- 16 Me CH ₂ CH (Me) H CH ₂ OEt 6-EtS -3-Pyr O 65- 17 Me CH ₂ CH (Me) H CH ₂ OEt 6-iPrS-3-Pyr O 65-18 Me CH ₂ CH (Me) H CH ₂ OEt 6-MeSO ₂ -3-Pyr O 65-19 Me CH ₂ CH (Me) H CH ₂ OEt 6-EtSO ₂ -3-Pyr O 65-20 Me CH ₂ CH (Me) H CH ₂ OEt 6-iPrSO ₂ -3-Pyr O 65- 21 Me CH ₂ CH (Me) H CH ₂ OEt 6-Bz-3-Pyr O 65-22 Me CH ₂ CH (Me) H CH ₂ OEt 6-PhO-3-Pyr O 65- 23 Me CH ₂ CH (Me) H CH ₂ OEt 6-PhS-3-Pyr O 65-24 Me CH ₂ CH (Me) H CH ₂ OEt 6-PhSO ₂ -3-Pyr O 65-25 Me CH ₂ CH (Me) H CH ₂ OEt 2 -Quin O 65- 26 Me CH ₂ CH (Me) H CH ₂ OEt 4-MeO-Ph O 65- 27 Me CH ₂ CH (Me) H CH ₂ OEt 4-EtO-Ph O 65- 28 Me CH ₂ CH (Me) H CH ₂ OEt 4-iPrO-Ph O 65- 29 Me CH ₂ CH (Me) H CH ₂ OEt 4-MeS-Ph O 65-30 Me CH ₂ CH (Me) H CH ₂ OEt 4-EtS -Ph O 65- 31 Me CH ₂ CH (Me) H CH ₂ OEt 4-iPrS-Ph O 65- 32 Me CH ₂ CH (Me) H CH ₂ OEt 4-MeSO ₂ -Ph O 65- 33 Me CH ₂ CH (Me) H CH ₂ OEt 4-EtSO ₂ -Ph O 65- 34 Me CH ₂ CH (Me) H CH ₂ OEt 4-iPrSO ₂ -Ph O 65- 35 Me CH ₂ CH (Me) H CH ₂ OEt 4- (Pyr-2) Ph O 65- 36 Me CH ₂ CH (Me) H CH ₂ OEt 4- (Pyr-3) Ph O 65- 37 Me CH ₂ CH (Me) H CH ₂ OEt 4- (Pyr -4) Ph O 65- 38 Me CH ₂ CH (Me) H CH ₂ OEt 3-Ph-6-Pyr O ────────────────────────────── ────.

[0196]

[Table 66] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 66- 1 Me (CH ₂ ) ₂ H CH ₂ Ph 4-Ph-Ph O 66- 2 Me (CH ₂ ) ₂ H CH ₂ Ph 4- (Pyr-2) Ph O 66- 3 Me (CH ₂ ) ₂ H CH ₂ CH ₂ Ph 4-Ph-Ph O 66- 4 Me (CH ₂ ) ₂ H CH ₂ CH ₂ Ph 4- (Pyr-2) Ph O 66- 5 Me (CH ₂ ) ₂ H CH ₂ (CH ₂ ) ₂ Ph 4-Ph-Ph O 66 -6 Me (CH ₂ ) ₂ H CH ₂ (CH ₂ ) ₂ Ph 4- (Pyr-2) Ph O 66-7 Me (CH ₂ ) ₂ H CH ₂ (CH ₂ ) ₃ Ph 4-Ph-Ph O 66- 8 Me (CH ₂ ) ₂ H CH ₂ (CH ₂ ) ₃ Ph 4- (Pyr-2) Ph O 66- 9 Me (CH ₂ ) ₂ H CH ₂ (CH ₂ ) ₄ Ph 4-Ph-Ph O 66- 10 Me (CH ₂ ) ₂ H CH ₂ (CH ₂ ) ₄ Ph 4- (Pyr-2) Ph O 66- 11 Me (CH ₂ ) ₂ H CH ₂ (CH ₂ ) ₅ Ph 4-Ph- Ph O 66-12 Me (CH ₂ ) ₂ H CH ₂ (CH ₂ ) ₅ Ph 4- (Pyr-2) Ph O 66-13 Me (CH ₂ ) ₂ H CH ₂ (CH ₂ ) ₆ Ph 4-Ph _{-Ph O 66- 14 Me (CH 2} ) 2 H CH 2 (CH 2) 6 Ph 4- (Pyr-2) Ph O ────── ───────────────────────────.

[0197]

[Table 67] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 67- 1 Me (CH ₂ ) ₂ H CH ₂ Me 4-Ph-Ph O 67- 2 Me (CH ₂ ) ₂ H CH ₂ Me 4- (Pyr-2) Ph O 67- 3 Me (CH ₂ ) ₂ H CH ₂ Et 4-Ph-Ph O 67 -4 Me (CH ₂ ) ₂ H CH ₂ Et 4- (Pyr-2) Ph O 67-5 Me (CH ₂ ) ₂ H CH ₂ Pr 4-Ph-Ph O 67-6 Me (CH ₂ ) ₂ H CH ₂ Pr 4- (Pyr-2) Ph O 67- 7 Me (CH ₂ ) ₂ H CH ₂ Bu 4-Ph-Ph O 67- 8 Me (CH ₂ ) ₂ H CH ₂ Bu 4- (Pyr-2 ) Ph O 67- 9 Me (CH ₂ ) ₂ H CH ₂ Pen 4-Ph-Ph O 67- 10 Me (CH ₂ ) ₂ H CH ₂ Pen 4- (Pyr-2) Ph O 67- 11 Me (CH ₂ ) ₂ H CH ₂ Hex 4-Ph-Ph O 67-12 Me (CH ₂ ) ₂ H CH ₂ Hex 4- (Pyr-2) Ph O ─────────────── ───────────────────.

[0198]

[Table 68] Example R ¹ R ² R ³ ZW X Y compound number ──────────────────────────────────── 68- 1 Me (CH ₂ ) ₂ H CH ₂ OPh 4-Ph-Ph O 68- 2 Me (CH ₂ ) ₂ H CH ₂ OPh 4- (Pyr-2) Ph O 68- 3 Me (CH ₂ ) ₂ H CH ₂ OCH ₂ Ph 4-Ph-Ph O 68- 4 Me (CH ₂ ) ₂ H CH ₂ OCH ₂ Ph 4- (Pyr-2) Ph O 68- 5 Me (CH ₂ ) ₂ H CH ₂ O (CH ₂ ) ₂ Ph 4-Ph-Ph O 68- 6 Me (CH ₂ ) ₂ H CH ₂ O (CH ₂ ) ₂ Ph 4- (Pyr-2) Ph O 68- 7 Me (CH ₂ ) ₂ H CH ₂ O (CH ₂ ) ₃ Ph 4-Ph -Ph O 68- 8 Me (CH ₂ ) ₂ H CH ₂ O (CH ₂ ) ₃ Ph 4- (Pyr-2) Ph O 68- 9 Me (CH ₂ ) ₂ H CH ₂ O (CH ₂ ) ₄ Ph 4-Ph-Ph O 68-10 Me (CH ₂ ) ₂ H CH ₂ O (CH ₂ ) ₄ Ph 4- (Pyr-2) Ph O 68-11 Me (CH ₂ ) ₂ H CH ₂ O (CH ₂ ) ₅ Ph 4-Ph-Ph O 68-12 Me (CH ₂ ) ₂ H CH ₂ O (CH ₂ ) ₅ Ph 4- (Pyr-2) Ph O 68-13 Me (CH ₂ ) ₂ H CH ₂ O _{(CH 2) 6 Ph 4-} Ph-Ph O 68- 14 Me (CH 2) 2 H CH 2 O (CH 2) 6 Ph 4- (Pyr-2) Ph O ─ ────────────────────────────────.

In the above table, (1) Preferably, exemplified compound numbers 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1
-10, 1-11, 1-14, 1-15, 1-16, 1
-17, 1-18, 1-19, 1-20, 1-21, 1
-22, 1-23, 1-24, 1-25, 1-26, 1
-27, 1-28, 1-29, 1-30, 1-31, 1
-32, 1-33, 1-34, 1-35, 1-36, 1
-37, 1-38, 1-39, 1-40, 1-41, 1
-42, 1-43, 1-44, 1-45, 1-53, 1
-56, 1-58, 1-60, 1-66, 1-70, 1
-72, 1-78, 1-80, 1-87, 1-88, 1
-89, 1-90, 1-91, 1-92, 1-93, 1
-94, 1-95, 1-96, 1-97, 1-98, 1
-99, 1-100, 1-101, 1-102, 1-1
03, 1-104, 1-105, 1-106, 1-10
7, 1-108, 1-109, 1-110, 1-11
1, 1-112, 1-144, 1-145, 1-14
6, 1-147, 1-148, 1-149, 1-15
0, 1-155, 1-156, 1-157, 1-15
8, 1-161, 1-162, 1-163, 1-16
4, 1-165, 1-166, 1-167, 1-16
8, 1-169, 1-170, 1-171, 1-17
2, 1-175, 1-176, 1-180, 1-18
1, 1-182, 1-183, 1-184, 1-18
5, 1-186, 1-187, 1-188, 1-18
9, 1-190, 1-191, 1-192, 1-19
3, 1-194, 1-195, 1-196, 1-19
7, 1-198, 1-199, 1-200, 1-20
1, 1-202, 1-203, 2-1, 2-2, 2-
3, 2-4, 2-5, 2-7, 2-10, 2-11, 2
-14, 2-15, 2-16, 2-17, 2-18, 2
-19, 2-20, 2-21, 2-22, 2-23, 2
-24, 2-25, 2-26, 2-27, 2-28, 2
-29, 2-30, 2-31, 2-32, 2-33, 2
-34, 2-35, 2-36, 2-37, 2-38, 2
-39, 2-40, 2-41, 2-42, 2-43, 2
-44, 2-45, 2-53, 2-56, 2-58, 2
-60, 2-66, 2-70, 2-72, 2-78, 2
-80, 2-87, 2-88, 2-89, 2-90, 2
-91, 2-92, 2-93, 2-94, 2-95, 2
-96, 2-97, 2-98, 2-99, 2-100,
2-101, 2-102, 2-103, 2-104, 2
-105, 2-106, 2-107, 2-108, 2-
109, 2-110, 2-111, 2-112, 2-1
44, 2-145, 2-146, 2-147, 2-14
8, 2-149, 2-150, 2-155, 2-15
6, 2-157, 2-158, 2-161, 2-16
2, 2-163, 2-164, 2-165, 2-16
6, 2-167, 2-168, 2-169, 2-17
0, 2-171, 2-172, 2-175, 2-17
6, 2-180, 2-181, 2-182, 2-18
3, 2-184, 2-185, 2-186, 2-18
7, 2-188, 2-189, 2-190, 2-19
1, 2-192, 2-193, 2-194, 2-19
5, 2-196, 2-197, 2-198, 2-19
9, 2-200, 2-201, 2-202, 2-20
3, 3-1, 3-2, 3-3, 3-4, 3-5, 3-
7, 3-10, 3-11, 3-14, 3-15, 3-1
6, 3-17, 3-18, 3-19, 3-20, 3-2
1, 3-22, 3-23, 3-24, 3-25, 3-2
6, 3-27, 3-28, 3-29, 3-30, 3-3
1, 3-32, 3-33, 3-34, 3-35, 3-3
6, 3-37, 3-38, 3-39, 3-40, 3-4
1, 3-42, 3-43, 3-44, 3-45, 3-5
3, 3-56, 3-58, 3-60, 3-66, 3-7
0, 3-72, 3-78, 3-80, 3-87, 3-8
8, 3-89, 3-90, 3-91, 3-92, 3-9
3, 3-94, 3-95, 3-96, 3-97, 3-9
8, 3-99, 3-100, 3-101, 3-102,
3-103, 3-104, 3-105, 3-106, 3
-107, 3-108, 3-109, 3-110, 3-
111, 3-112, 3-144, 3-145, 3-1
46, 3-147, 3-148, 3-149, 3-15
0, 3-155, 3-156, 3-157, 3-15
8, 3-161, 3-162, 3-163, 3-16
4, 3-165, 3-166, 3-167, 3-16
8, 3-169, 3-170, 3-171, 3-17
2, 3-175, 3-176, 3-180, 3-18
1, 3-182, 3-183, 3-184, 3-18
5, 3-186, 3-187, 3-188, 3-18
9, 3-190, 3-191, 3-192, 3-19
3, 3-194, 3-195, 3-196, 3-19
7, 3-198, 3-199, 3-200, 3-20
1, 3-202, 3-203, 4-1 4-2, 4-
3, 4-4, 4-5, 4-7, 4-10, 4-11, 4
-14, 4-15, 4-16, 4-17, 4-18, 4
-19, 4-20, 4-21, 4-22, 4-23, 4
-24, 4-25, 4-26, 4-27, 4-28, 4
-29, 4-30, 4-31, 4-32, 4-33, 4
-34, 4-35, 4-36, 4-37, 4-38, 4
-39, 4-40, 4-41, 4-42, 4-43, 4
-44, 4-45, 4-53, 4-56, 4-58, 4
-60, 4-66, 4-70, 4-72, 4-78, 4
-80, 4-87, 4-88, 4-89, 4-90, 4
-91, 4-92, 4-93, 4-94, 4-95, 4
-96, 4-97, 4-98, 4-99, 4-100,
4-101, 4-102, 4-103, 4-104, 4
-105, 4-106, 4-107, 4-108, 4-
109, 4-110, 4-111, 4-112, 4-1
44, 4-145, 4-146, 4-147, 4-14
8, 4-149, 4-150, 4-155, 4-15
6, 4-157, 4-158, 4-161, 4-16
2, 4-163, 4-164, 4-165, 4-16
6, 4-167, 4-168, 4-169, 4-17
0, 4-171, 4-172, 4-175, 4-17
6, 4-180, 4-181, 4-182, 4-18
3, 4-184, 4-185, 4-186, 4-18
7, 4-188, 4-189, 4-190, 4-19
1, 4-192, 4-193, 4-194, 4-19
5, 4-196, 4-197, 4-198, 4-19
9, 4-200, 4-201, 4-202, 4-20
3, 5-1, 5-2, 5-3, 5-4, 5-5, 5-
7, 5-10, 5-11, 5-14, 5-15, 5-1
6, 5-17, 5-18, 5-19, 5-20, 5-2
1, 5-22, 5-23, 5-24, 5-25, 5-2
6, 5-27, 5-28, 5-29, 5-30, 5-3
1, 5-32, 5-33, 5-34, 5-35, 5-3
6, 5-37, 5-38, 5-39, 5-40, 5-4
1, 5-42, 5-43, 5-44, 5-45, 5-5
3, 5-56, 5-58, 5-60, 5-66, 5-7
0, 5-72, 5-78, 5-80, 5-87, 5-8
8, 5-89, 5-90, 5-91, 5-92, 5-9
3, 5-94, 5-95, 5-96, 5-97, 5-9
8, 5-99, 5-100, 5-101, 5-102,
5-103, 5-104, 5-105, 5-106, 5
-107, 5-108, 5-109, 5-110, 5-
111, 5-112, 5-144, 5-145, 5-1
46, 5-147, 5-148, 5-149, 5-15
0, 5-155, 5-156, 5-157, 5-15
8, 5-161, 5-162, 5-163, 5-16
4, 5-165, 5-166, 5-167, 5-16
8, 5-169, 5-170, 5-171, 5-17
2, 5-175, 5-176, 5-180, 5-18
1, 5-182, 5-183, 5-184, 5-18
5, 5-186, 5-187, 5-188, 5-18
9, 5-190, 5-191, 5-192, 5-19
3, 5-194, 5-195, 5-196, 5-19
7, 5-198, 5-199, 5-200, 5-20
1, 5-202, 5-203, 6-1, 6-2, 6
3, 6-4, 6-5, 6-7, 6-10, 6-11, 6
-14, 6-15, 6-16, 6-17, 6-18, 6
-19, 6-20, 6-21, 6-22, 6-23, 6
-24, 6-25, 6-26, 6-27, 6-28, 6
-29, 6-30, 6-31, 6-32, 6-33, 6
-34, 6-35, 6-36, 6-37, 6-38, 6
-39, 6-40, 6-41, 6-42, 6-43, 6
-44, 6-45, 6-53, 6-56, 6-58, 6
-60, 6-66, 6-70, 6-72, 6-78, 6
-80, 6-87, 6-88, 6-89, 6-90, 6
-91, 6-92, 6-93, 6-94, 6-95, 6
-96, 6-97, 6-98, 6-99, 6-100,
6-101, 6-102, 6-103, 6-104, 6
-105, 6-106, 6-107, 6-108, 6
109, 6-110, 6-111, 6-112, 6-1
44, 6-145, 6-146, 6-147, 6-14
8, 6-149, 6-150, 6-155, 6-15
6, 6-157, 6-158, 6-161, 6-16
2, 6-163, 6-164, 6-165, 6-16
6, 6-167, 6-168, 6-169, 6-17
0, 6-171, 6-172, 6-175, 6-17
6, 6-180, 6-181, 6-182, 6-18
3, 6-184, 6-185, 6-186, 6-18
7, 6-188, 6-189, 6-190, 6-19
1, 6-192, 6-193, 6-194, 6-19
5, 6-196, 6-197, 6-198, 6-19
9, 6-200, 6-201, 6-202, 6-20
3, 7-1, 7-2, 7-3, 7-4, 7-5, 7-
7, 7-10, 7-11, 7-14, 7-15, 7-1
6, 7-17, 7-18, 7-19, 7-20, 7-2
1, 7-22, 7-23, 7-24, 7-25, 7-2
6, 7-27, 7-28, 7-29, 7-30, 7-3
1, 7-32, 7-33, 7-34, 7-35, 7-3
6, 7-37, 7-38, 7-39, 7-40, 7-4
1, 7-42, 7-43, 7-44, 7-45, 7-5
3, 7-56, 7-58, 7-60, 7-66, 7-7
0, 7-72, 7-78, 7-80, 7-87, 7-8
8, 7-89, 7-90, 7-91, 7-92, 7-9
3, 7-94, 7-95, 7-96, 7-97, 7-9
8, 7-99, 7-100, 7-101, 7-102,
7-103, 7-104, 7-105, 7-106, 7
-107, 7-108, 7-109, 7-110, 7-
111, 7-112, 7-144, 7-145, 7-1
46, 7-147, 7-148, 7-149, 7-15
0, 7-155, 7-156, 7-157, 7-15
8, 7-161, 7-162, 7-163, 7-16
4, 7-165, 7-166, 7-167, 7-16
8, 7-169, 7-170, 7-171, 7-17
2, 7-175, 7-176, 7-180, 7-18
1, 7-182, 7-183, 7-184, 7-18
5, 7-186, 7-187, 7-188, 7-18
9, 7-190, 7-191, 7-192, 7-19
3, 7-194, 7-195, 7-196, 7-19
7, 7-198, 7-199, 7-200, 7-20
1, 7-202, 7-203, 8-1, 8-2, 8-
3, 8-4, 8-5, 8-7, 8-10, 8-11, 8
-14, 8-15, 8-16, 8-17, 8-18, 8
-19, 8-20, 8-21, 8-22, 8-23, 8
-24, 8-25, 8-26, 8-27, 8-28, 8
-29, 8-30, 8-31, 8-32, 8-33, 8
-34, 8-35, 8-36, 8-37, 8-38, 8
-39, 8-40, 8-41, 8-42, 8-43, 8
-44, 8-45, 8-53, 8-56, 8-58, 8
-60, 8-66, 8-70, 8-72, 8-78, 8
-80, 8-87, 8-88, 8-89, 8-90, 8
-91, 8-92, 8-93, 8-94, 8-95, 8
-96, 8-97, 8-98, 8-99, 8-100,
8-101, 8-102, 8-103, 8-104, 8
-105, 8-106, 8-107, 8-108, 8-
109, 8-110, 8-111, 8-112, 8-1
44, 8-145, 8-146, 8-147, 8-14
8, 8-149, 8-150, 8-155, 8-15
6, 8-157, 8-158, 8-161, 8-16
2, 8-163, 8-164, 8-165, 8-16
6, 8-167, 8-168, 8-169, 8-17
0, 8-171, 8-172, 8-175, 8-17
6, 8-180, 8-181, 8-182, 8-18
3, 8-184, 8-185, 8-186, 8-18
7, 8-188, 8-189, 8-190, 8-19
1, 8-192, 8-193, 8-194, 8-19
5, 8-196, 8-197, 8-198, 8-19
9, 8-200, 8-201, 8-202, 8-20
3,9-1,9-2,9-3,9-4,9-5,9-
7, 9-10, 9-11, 9-14, 9-15, 9-1
6, 9-17, 9-18, 9-19, 9-20, 9-2
1, 9-22, 9-23, 9-24, 9-25, 9-2
6, 9-27, 9-28, 9-29, 9-30, 9-3
1, 9-32, 9-33, 9-34, 9-35, 9-3
6, 9-37, 9-38, 9-39, 9-40, 9-4
1, 9-42, 9-43, 9-44, 9-45, 9-5
3, 9-56, 9-58, 9-60, 9-66, 9-7
0, 9-72, 9-78, 9-80, 9-87, 9-8
8, 9-89, 9-90, 9-91, 9-92, 9-9
3, 9-94, 9-95, 9-96, 9-97, 9-9
8, 9-99, 9-100, 9-101, 9-102,
9-103, 9-104, 9-105, 9-106, 9
-107, 9-108, 9-109, 9-110, 9-
111, 9-112, 9-144, 9-145, 9-1
46, 9-147, 9-148, 9-149, 9-15
0, 9-155, 9-156, 9-157, 9-15
8, 9-161, 9-162, 9-163, 9-16
4, 9-165, 9-166, 9-167, 9-16
8, 9-169, 9-170, 9-171, 9-17
2, 9-175, 9-176, 9-180, 9-18
1, 9-182, 9-183, 9-184, 9-18
5, 9-186, 9-187, 9-188, 9-18
9, 9-190, 9-191, 9-192, 9-19
3, 9-194, 9-195, 9-196, 9-19
7, 9-198, 9-199, 9-200, 9-20
1, 9-202, 9-203, 10-1, 10-2, 1
0-3, 10-4, 10-5, 10-7, 10-10,
10-11, 10-14, 10-15, 10-16, 1
0-17, 10-18, 10-19, 10-20, 10
-21, 10-22, 10-23, 10-24, 10-
25, 10-26, 10-27, 10-28, 10-2
9, 10-30, 10-31, 10-32, 10-3
3, 10-34, 10-35, 10-36, 10-3
7, 10-38, 10-39, 10-40, 10-4
1, 10-42, 10-43, 10-44, 10-4
5, 10-53, 10-56, 10-58, 10-6
0, 10-66, 10-70, 10-72, 10-7
8, 10-80, 10-87, 10-88, 10-8
9, 10-90, 10-91, 10-92, 10-9
3, 10-94, 10-95, 10-96, 10-9
7, 10-98, 10-99, 10-100, 10-1
01, 10-102, 10-103, 10-104, 1
0-105, 10-106, 10-107, 10-10
8, 10-109, 10-110, 10-111, 10
-112, 10-144, 10-145, 10-14
6, 10-147, 10-148, 10-149, 10
-150, 10-155, 10-156, 10-15
7, 10-158, 10-161, 10-162, 10
-163, 10-164, 10-165, 10-16
6, 10-167, 10-168, 10-169, 10
-170, 10-171, 10-172, 10-17
5, 10-176, 10-180, 10-181, 10
-182, 10-183, 10-184, 10-18
5, 10-186, 10-187, 10-188, 10
-189, 10-190, 10-191, 10-19
2, 10-193, 10-194, 10-195, 10
-196, 10-197, 10-198, 10-19
9, 10-200, 10-201, 10-202, 10
-203, 11-4, 11-11, 11-12, 11-
13, 11-14, 11-35, 11-36, 11-3
7, 11-38, 12-4, 12-11, 12-12,
12-13, 12-14, 12-35, 12-36, 1
2-37, 12-38, 13-4, 13-11, 13-
12, 13-13, 13-14, 13-35, 13-3
6, 13-37, 13-38, 14-4, 14-11,
14-12, 14-13, 14-14, 14-35, 1
4-36, 14-37, 14-38, 15-4, 15-
11, 15-12, 15-13, 15-14, 15-3
5, 15-36, 15-37, 15-38, 16-4,
16-11, 16-12, 16-13, 16-14, 1
6-35, 16-36, 16-37, 16-38, 17
-4, 17-11, 17-12, 17-13, 17-1
4, 17-35, 17-36, 17-37, 17-3
8, 18-4, 18-11, 18-12, 18-13,
18-14, 18-35, 18-36, 18-37, 1
8-38, 19-4, 19-11, 19-12, 19-
13, 19-14, 19-35, 19-36, 19-3
7, 19-38, 20-4, 20-11, 20-12,
20-13, 20-14, 20-35, 20-36, 2
0-37, 20-38, 21-4, 21-11, 21-
12, 21-13, 21-14, 21-35, 21-3
6, 21-37, 21-38, 22-4, 22-11,
22-12, 22-13, 22-14, 22-35, 2
2-36, 22-37, 22-38, 23-4, 23
11, 23-12, 23-13, 23-14, 23-3
5, 23-36, 23-37, 23-38, 24-4,
24-11, 24-12, 24-13, 24-14, 2
4-35, 24-36, 24-37, 24-38, 25
-4, 25-11, 25-12, 25-13, 25-1
4, 25-35, 25-36, 25-37, 25-3
8, 26-4, 26-11, 26-12, 26-13,
26-14, 26-35, 26-36, 26-37, 2
6-38, 27-4, 27-11, 27-12, 27-
13, 27-14, 27-35, 27-36, 27-3
7, 27-38, 28-4, 28-11, 28-12,
28-13, 28-14, 28-35, 28-36, 2
8-37, 28-38, 29-4, 29-11, 29-
12, 29-13, 29-14, 29-35, 29-3
6, 29-37, 29-38, 30-4, 30-11,
30-12, 30-13, 30-14, 30-35, 3
0-36, 30-37, 30-38, 31-4, 31-
11, 31-12, 31-13, 31-14, 31-3
5, 31-36, 31-37, 31-38, 32-4,
32-11, 32-12, 32-13, 32-14, 3
2-35, 32-36, 32-37, 32-38, 33
-4, 33-11, 33-12, 33-13, 33-1
4, 33-35, 33-36, 33-37, 33-3
8, 34-4, 34-11, 34-12, 34-13,
34-14, 34-35, 34-36, 34-37, 3
4-38, 35-4, 35-11, 35-12, 35-
13, 35-14, 35-35, 35-36, 35-3
7, 35-38, 36-4, 36-11, 36-12,
36-13, 36-14, 36-35, 36-36, 3
6-37, 36-38, 37-4, 37-11, 37-
12, 37-13, 37-14, 37-35, 37-3
6, 37-37, 37-38, 38-4, 38-11,
38-12, 38-13, 38-14, 38-35, 3
8-36, 38-37, 38-38, 39-4, 39-
11, 39-12, 39-13, 39-14, 39-3
5, 39-36, 39-37, 39-38, 40-4,
40-11, 40-12, 40-13, 40-14, 4
0-35, 40-36, 40-37, 40-38, 41
-4, 41-11, 41-12, 41-13, 41-1
4, 41-35, 41-36, 41-37, 41-3
8, 42-4, 42-11, 42-12, 42-13,
42-14, 42-35, 42-36, 42-37, 4
2-38, 43-4, 43-11, 43-12, 43-
13, 43-14, 43-35, 43-36, 43-3
7, 43-38, 44-4, 44-11, 44-12,
44-13, 44-14, 44-35, 44-36, 4
4-37, 44-38, 45-4, 45-11, 45-
12, 45-13, 45-14, 45-35, 45-3
6, 45-37, 45-38, 46-4, 46-11,
46-12, 46-13, 46-14, 46-35, 4
6-36, 46-37, 46-38, 47-4, 47-
11, 47-12, 47-13, 47-14, 47-3
5, 47-36, 47-37, 47-38, 48-4,
48-11, 48-12, 48-13, 48-14, 4
8-35, 48-36, 48-37, 48-38, 49
-4, 49-11, 49-12, 49-13, 49-1
4, 49-35, 49-36, 49-37, 49-3
8, 50-4, 50-11, 50-12, 50-13,
50-14, 50-35, 50-36, 50-37, 5
0-38, 51-4, 51-11, 51-12, 51-
13, 51-14, 51-35, 51-36, 51-3
7, 51-38, 52-4, 52-11, 52-12,
52-13, 52-14, 52-35, 52-36, 5
2-37, 52-38, 53-4, 53-11, 53-
12, 53-13, 53-14, 53-35, 53-3
6, 53-37, 53-38, 54-4, 54-11,
54-12, 54-13, 54-14, 54-35, 5
4-36, 54-37, 54-38, 55-4, 55-
11, 55-12, 55-13, 55-14, 55-3
5, 55-36, 55-37, 55-38, 66-3,
66-4, 66-5, 66-6, 66-7, 66-8,
66-9, 66-10, 66-11, 66-12, 66
-13, 66-14, 67-1, 67-2, 67-3,
67-4, 67-5, 67-6, 67-7, 67-8,
67-9, 67-10, 67-11, 67-12, 68
-1, 68-2, 68-3, 68-4, 68-5, 68
-6, 68-7, 68-8, 68-9, 68-10, 6
8-11, 68-12, 68-13, 68-14.

(2) More preferably, Exemplified Compound Nos. 1-1, 1-2, 1-3, 1-10, 1-11, 1-1
4, 1-15, 1-16, 1-17, 1-18, 1-1
9, 1-20, 1-21, 1-22, 1-23, 1-2
5, 1-29, 1-31, 1-33, 1-34, 1-3
5, 1-36, 1-37, 1-38, 1-39, 1-4
1, 1-43, 1-45, 1-87, 1-88, 1-8
9, 1-90, 1-91, 1-92, 1-93, 1-9
4, 1-95, 1-96, 1-97, 1-98, 1-9
9, 1-100, 1-101, 1-102, 1-10
3, 1-104, 1-105, 1-106, 1-10
7, 1-108, 1-109, 1-110, 1-11
1, 1-112, 1-149, 1-150, 1-15
6, 1-158, 1-162, 1-164, 1-16
6, 1-168, 1-170, 1-172, 1-17
5, 1-176, 1-180, 1-181, 1-18
2, 1-183, 1-184, 1-185, 1-18
6, 1-187, 1-188, 1-189, 1-19
0, 1-191, 1-192, 1-193, 1-19
4, 1-195, 1-196, 1-197, 1-19
8, 1-199, 1-200, 1-201, 1-20
2, 1-203, 2-1, 2-2, 2-3, 2-10,
2-11, 2-14, 2-15, 2-16, 2-17,
2-18, 2-19, 2-20, 2-21, 2-22,
2-23, 2-25, 2-29, 2-31, 2-33,
2-34, 2-35, 2-36, 2-37, 2-38,
2-39, 2-41, 2-43, 2-45, 2-87,
2-88, 2-89, 2-90, 2-91, 2-92,
2-93, 2-94, 2-95, 2-96, 2-97,
2-98, 2-99, 2-100, 2-101, 2-1
02, 2-103, 2-104, 2-105, 2-10
6, 2-107, 2-108, 2-109, 2-11
0, 2-111, 2-112, 2-149, 2-15
0, 2-156, 2-158, 2-162, 2-16
4, 2-166, 2-168, 2-170, 2-17
2, 2-175, 2-176, 2-180, 2-18
1, 2-182, 2-183, 2-184, 2-18
5, 2-186, 2-187, 2-188, 2-18
9, 2-190, 2-191, 2-192, 2-19
3, 2-194, 2-195, 2-196, 2-19
7, 2-198, 2-199, 2-200, 2-20
1, 2-202, 2-203, 3-1, 3-2, 3-
3, 3-10, 3-11, 3-14, 3-15, 3-1
6, 3-17, 3-18, 3-19, 3-20, 3-2
1, 3-22, 3-23, 3-25, 3-29, 3-3
1, 3-33, 3-34, 3-35, 3-36, 3-3
7, 3-38, 3-39, 3-41, 3-43, 3-4
5, 3-87, 3-88, 3-89, 3-90, 3-9
1, 3-92, 3-93, 3-94, 3-95, 3-9
6, 3-97, 3-98, 3-99, 3-100, 3-
101, 3-102, 3-103, 3-104, 3-1
05, 3-106, 3-107, 3-108, 3-10
9, 3-110, 3-111, 3-112, 3-14
9, 3-150, 3-156, 3-158, 3-16
2, 3-164, 3-166, 3-168, 3-17
0, 3-172, 3-175, 3-176, 3-18
0, 3-181, 3-182, 3-183, 3-18
4, 3-185, 3-186, 3-187, 3-18
8, 3-189, 3-190, 3-191, 3-19
2, 3-193, 3-194, 3-195, 3-19
6, 3-197, 3-198, 3-199, 3-20
0, 3-201, 3-202, 3-203, 4-15,
4-35, 4-37, 4-39, 4-95, 4-96,
4-97, 4-98, 4-110, 5-15, 5-3
5, 5-37, 5-39, 5-95, 5-96, 5-9
7, 5-98, 5-110, 6-1, 6-2, 6-3,
6-10, 6-11, 6-14, 6-15, 6-16,
6-17, 6-18, 6-19, 6-20, 6-21,
6-22, 6-23, 6-25, 6-29, 6-31,
6-33, 6-34, 6-35, 6-36, 6-37,
6-38, 6-39, 6-41, 6-43, 6-45,
6-87, 6-88, 6-89, 6-90, 6-91,
6-92, 6-93, 6-94, 6-95, 6-96,
6-97, 6-98, 6-99, 6-100, 6-10
1, 6-102, 6-103, 6-104, 6-10
5, 6-106, 6-107, 6-108, 6-10
9, 6-110, 6-111, 6-112, 6-14
9, 6-150, 6-156, 6-158, 6-16
2, 6-164, 6-166, 6-168, 6-17
0, 6-172, 6-175, 6-176, 6-18
0, 6-181, 6-182, 6-183, 6-18
4, 6-185, 6-186, 6-187, 6-18
8, 6-189, 6-190, 6-191, 6-19
2, 6-193, 6-194, 6-195, 6-19
6, 6-197, 6-198, 6-199, 6-20
0, 6-201, 6-202, 6-203, 7-15,
7-35, 7-37, 7-39, 7-95, 7-96,
7-97, 7-98, 7-110, 8-1, 8-2, 8
-3, 8-10, 8-11, 8-14, 8-15, 8-
16, 8-17, 8-18, 8-19, 8-20, 8-
21, 8-22, 8-23, 8-25, 8-29, 8-
31, 8-33, 8-34, 8-35, 8-36, 8-
37, 8-38, 8-39, 8-41, 8-43, 8-
45, 8-87, 8-88, 8-89, 8-90, 8-
91, 8-92, 8-93, 8-94, 8-95, 8-
96, 8-97, 8-98, 8-99, 8-100, 8
−101, 8-102, 8-103, 8-104, 8-
105, 8-106, 8-107, 8-108, 8-1
09, 8-110, 8-111, 8-112, 8-14
9, 8-150, 8-156, 8-158, 8-16
2, 8-164, 8-166, 8-168, 8-17
0, 8-172, 8-175, 8-176, 8-18
0, 8-181, 8-182, 8-183, 8-18
4, 8-185, 8-186, 8-187, 8-18
8, 8-189, 8-190, 8-191, 8-19
2, 8-193, 8-194, 8-195, 8-19
6, 8-197, 8-198, 8-199, 8-20
0, 8-201, 8-202, 8-203, 9-15,
9-35, 9-37, 9-39, 9-95, 9-96,
9-97, 9-98, 9-110, 10-1, 10-
2, 10-3, 10-10, 10-11, 10-14,
10-15, 10-16, 10-17, 10-18, 1
0-19, 10-20, 10-21, 10-22, 10
-23, 10-25, 10-29, 10-31, 10-
33, 10-34, 10-35, 10-36, 10-3
7, 10-38, 10-39, 10-41, 10-4
3, 10-45, 10-87, 10-88, 10-8
9, 10-90, 10-91, 10-92, 10-9
3, 10-94, 10-95, 10-96, 10-9
7, 10-98, 10-99, 10-100, 10-1
01, 10-102, 10-103, 10-104, 1
0-105, 10-106, 10-107, 10-10
8, 10-109, 10-110, 10-111, 10
-112, 10-149, 10-150, 10-15
6, 10-158, 10-162, 10-164, 10
-166, 10-168, 10-170, 10-17
2, 10-175, 10-176, 10-180, 10
-181, 10-182, 10-183, 10-18
4, 10-185, 10-186, 10-187, 10
-188, 10-189, 10-190, 10-19
1, 10-192, 10-193, 10-194, 10
-195, 10-196, 10-197, 10-19
8, 10-199, 10-200, 10-201, 10
-202, 10-203, 24-4, 24-11, 24
-12, 24-13, 24-14, 24-35, 24-
36, 24-37, 24-38, 25-4, 25-1
1, 25-12, 25-13, 25-14, 25-3
5, 25-36, 25-37, 25-38, 26-4,
26-11, 26-12, 26-13, 26-14, 2
6-35, 26-36, 26-37, 26-38, 27
-4, 27-11, 27-12, 27-13, 27-1
4, 27-35, 27-36, 27-37, 27-3
8, 28-4, 28-11, 28-12, 28-13,
28-14, 28-35, 28-36, 28-37, 2
8-38, 29-4, 29-11, 29-12, 29-
13, 29-14, 29-35, 29-36, 29-3
7, 29-38, 30-4, 30-11, 30-12,
30-13, 30-14, 30-35, 30-36, 3
0-37, 30-38, 31-4, 31-11, 31-
12, 31-13, 31-14, 31-35, 31-3
6, 31-37, 31-38, 32-4, 32-11,
32-12, 32-13, 32-14, 32-35, 3
2-36, 32-37, 32-38, 33-4, 33-
11, 33-12, 33-13, 33-14, 33-3
5, 33-36, 33-37, 33-38, 34-4,
34-11, 34-12, 34-13, 34-14, 3
4-35, 34-36, 34-37, 34-38, 35
-4, 35-11, 35-12, 35-13, 35-1
4, 35-35, 35-36, 35-37, 35-3
8, 36-4, 36-11, 36-12, 36-13,
36-14, 36-35, 36-36, 36-37, 3
6-38, 37-4, 37-11, 37-12, 37-
13, 37-14, 37-35, 37-36, 37-3
7, 37-38, 38-4, 38-11, 38-12,
38-13, 38-14, 38-35, 38-36, 3
8-37, 38-38, 39-4, 39-11, 39-
12, 39-13, 39-14, 39-35, 39-3
6, 39-37, 39-38, 40-4, 40-11,
40-12, 40-13, 40-14, 40-35, 4
0-36, 40-37, 40-38, 41-4, 41-
11, 41-12, 41-13, 41-14, 41-3
5, 41-36, 41-37, 41-38, 42-4,
42-11, 42-12, 42-13, 42-14, 4
2-35, 42-36, 42-37, 42-38, 43
-4, 43-11, 43-12, 43-13, 43-1
4, 43-35, 43-36, 43-37, 43-3
8, 44-4, 44-11, 44-12, 44-13,
44-14, 44-35, 44-36, 44-37, 4
4-38, 45-4, 45-11, 45-12, 45-
13, 45-14, 45-35, 45-36, 45-3
7, 45-38, 47-4, 47-11, 47-12,
47-13, 47-14, 47-35, 47-36, 4
7-37, 47-38, 49-4, 49-11, 49-
12, 49-13, 49-14, 49-35, 49-3
6, 49-37, 49-38, 50-4, 50-11,
50-12, 50-13, 50-14, 50-35, 5
0-36, 50-37, 50-38, 51-4, 51-
11, 51-12, 51-13, 51-14, 51-3
5, 51-36, 51-37, 51-38, 52-4,
52-11, 52-12, 52-13, 52-14, 5
2-35, 52-36, 52-37, 52-38, 53
-4, 53-11, 53-12, 53-13, 53-1
4, 53-35, 53-36, 53-37, 53-3
8, 54-4, 54-11, 54-12, 54-13,
54-14, 54-35, 54-36, 54-37, 5
4-38, 66-3, 66-4, 66-5, 66-6,
66-7, 66-8, 66-9, 66-10, 66-1
1, 66-12, 66-13, 66-14, 67-1,
67-2, 67-3, 67-4, 67-5, 67-6,
67-7, 67-8, 67-9, 67-10, 67-1
1, 67-12, 68-1, 68-2, 68-3, 68
-4, 68-5, 68-6, 68-7, 68-8, 68
-9, 68-10.

(3) More preferably, Exemplified Compound Nos. 1-14, 1-15, 1-16, 1-17, 1-18,
1-19, 1-20, 1-21, 1-22, 1-23,
1-29, 1-31, 1-33, 1-34, 1-35,
1-36, 1-37, 1-38, 1-39, 1-41,
1-43, 1-45, 1-88, 1-90, 1-91,
1-92, 1-93, 1-94, 1-95, 1-96,
1-97, 1-98, 1-99, 1-100, 1-10
1, 1-102, 1-103, 1-104, 1-10
5, 1-106, 1-107, 1-108, 1-10
9, 1-110, 1-181, 1-182, 1-18
3, 1-184, 1-185, 1-186, 1-18
7, 1-188, 1-189, 1-192, 1-19
3, 1-195, 2-14, 2-15, 2-16, 2-
17, 2-18, 2-19, 2-20, 2-21, 2-
22, 2-23, 2-29, 2-31, 2-33, 2-
34, 2-35, 2-36, 2-37, 2-38, 2-
39, 2-41, 2-43, 2-45, 2-88, 2-
90, 2-91, 2-92, 2-93, 2-94, 2-
95, 2-96, 2-97, 2-98, 2-99, 2-
100, 2-101, 2-102, 2-103, 2-1
04, 2-105, 2-106, 2-107, 2-10
8, 2-109, 2-110, 2-181, 2-18
2, 2-183, 2-184, 2-185, 2-18
6, 2-187, 2-188, 2-189, 2-19
2, 2-193, 2-195, 3-14, 3-15, 3
-16, 3-17, 3-18, 3-19, 3-20, 3
-21, 3-22, 3-23, 3-29, 3-31,3
-33, 3-34, 3-35, 3-36, 3-37,
-38, 3-39, 3-41, 3-43, 3-45, 3
-88, 3-90, 3-91, 3-92, 3-93, 3
-94, 3-95, 3-96, 3-97, 3-98, 3
-99, 3-100, 3-101, 3-102, 3-1
03, 3-104, 3-105, 3-106, 3-10
7, 3-108, 3-109, 3-110, 3-18
1, 3-182, 3-183, 3-184, 3-18
5, 3-186, 3-187, 3-188, 3-18
9, 3-192, 3-193, 3-195, 5-15,
5-35, 5-37, 5-39, 5-95, 5-96,
5-97, 5-98, 5-110, 6-15, 6-3
5, 6-37, 6-39, 6-95, 6-96, 6-9
7, 6-98, 6-110, 24-4, 24-11, 2
4-12, 24-13, 24-14, 24-35, 24
-36, 24-37, 24-38, 25-4, 25-1
1, 25-12, 25-13, 25-14, 25-3
5, 25-36, 25-37, 25-38, 26-4,
26-11, 26-12, 26-13, 26-14, 2
6-35, 26-36, 26-37, 26-38, 27
-4, 27-11, 27-12, 27-13, 27-1
4, 27-35, 27-36, 27-37, 27-3
8, 28-4, 28-11, 28-12, 28-13,
28-14, 28-35, 28-36, 28-37, 2
8-38, 29-4, 29-11, 29-12, 29-
13, 29-14, 29-35, 29-36, 29-3
7, 29-38, 30-4, 30-11, 30-12,
30-13, 30-14, 30-35, 30-36, 3
0-37, 30-38, 31-4, 31-11, 31-
12, 31-13, 31-14, 31-35, 31-3
6, 31-37, 31-38, 32-4, 32-11,
32-12, 32-13, 32-14, 32-35, 3
2-36, 32-37, 32-38, 33-4, 33-
11, 33-12, 33-13, 33-14, 33-3
5, 33-36, 33-37, 33-38, 34-4,
34-11, 34-12, 34-13, 34-14, 3
4-35, 34-36, 34-37, 34-38, 35
-4, 35-11, 35-12, 35-13, 35-1
4, 35-35, 35-36, 35-37, 35-3
8, 36-4, 36-11, 36-12, 36-13,
36-14, 36-35, 36-36, 36-37, 3
6-38, 37-4, 37-11, 37-12, 37-
13, 37-14, 37-35, 37-36, 37-3
7, 37-38, 38-4, 38-11, 38-12,
38-13, 38-14, 38-35, 38-36, 3
8-37, 38-38, 39-4, 39-11, 39-
12, 39-13, 39-14, 39-35, 39-3
6, 39-37, 39-38, 40-4, 40-11,
40-12, 40-13, 40-14, 40-35, 4
0-36, 40-37, 40-38, 41-4, 41-
11, 41-12, 41-13, 41-14, 41-3
5, 41-36, 41-37, 41-38, 42-4,
42-11, 42-12, 42-13, 42-14, 4
2-35, 42-36, 42-37, 42-38, 43
-4, 43-11, 43-12, 43-13, 43-1
4, 43-35, 43-36, 43-37, 43-3
8, 44-4, 44-11, 44-12, 44-13,
44-14, 44-35, 44-36, 44-37, 4
4-38, 45-4, 45-11, 45-12, 45-
13, 45-14, 45-35, 45-36, 45-3
7, 45-38, 47-4, 47-11, 47-12,
47-13, 47-14, 47-35, 47-36, 4
7-37, 47-38, 49-4, 49-11, 49-
12, 49-13, 49-14, 49-35, 49-3
6, 49-37, 49-38, 50-4, 50-11,
50-12, 50-13, 50-14, 50-35, 5
0-36, 50-37, 50-38, 51-4, 51-
11, 51-12, 51-13, 51-14, 51-3
5, 51-36, 51-37, 51-38, 52-4,
52-11, 52-12, 52-13, 52-14, 5
2-35, 52-36, 52-37, 52-38, 53
-4, 53-11, 53-12, 53-13, 53-1
4, 53-35, 53-36, 53-37, 53-3
8, 54-4, 54-11, 54-12, 54-13,
54-14, 54-35, 54-36, 54-37, 5
4-38, 66-5, 66-6, 66-7, 66-8,
66-9, 66-10, 67-5, 67-6, 67-
7, 67-8, 68-2, 68-3.

(4) More preferably, Exemplified Compound Nos. 1-15, 1-17, 1-19, 1-21, 1-23,
1-35, 1-37, 1-39, 1-95, 1-96,
1-97, 1-98, 1-99, 1-100, 1-10
1, 1-102, 1-103, 1-104, 1-10
5, 1-108, 1-183, 1-185, 1-18
7, 1-189, 1-195, 2-15, 2-17, 2
-19, 2-21, 2-23, 2-35, 2-37, 2
-39, 2-95, 2-96, 2-97, 2-98, 2
-99, 2-100, 2-101, 2-102, 2-1
03, 2-104, 2-105, 2-108, 2-18
3, 2-185, 2-187, 2-189, 2-19
5, 3-15, 3-17, 3-19, 3-21, 3-2
3, 3-35, 3-37, 3-39, 3-95, 3-9
6, 3-97, 3-98, 3-99, 3-100, 3-
101, 3-102, 3-103, 3-104, 3-1
05, 3-108, 3-183, 3-185, 3-18
7, 3-189, 3-195, 5-15, 5-35, 5
-37, 5-39, 24-4, 24-11, 24-3
5, 24-36, 24-37, 25-4, 25-11,
25-35, 25-36, 25-37, 26-4, 26
-11, 26-35, 26-36, 26-37, 27-
4, 27-11, 27-35, 27-36, 27-3
7, 28-4, 28-11, 28-35, 28-36,
28-37, 29-4, 29-11, 29-35, 29
-36, 29-37, 30-4, 30-11, 30-3
5, 30-36, 30-37, 31-4, 31-11,
31-35, 31-36, 31-37, 32-4, 32
-11, 32-35, 32-36, 32-37, 33-
4, 33-11, 33-35, 33-36, 33-3
7, 34-4, 34-11, 34-35, 34-36,
34-37, 35-4, 35-11, 35-35, 35
-36, 35-37, 36-4, 36-11, 36-3
5, 36-36, 36-37, 37-4, 37-11,
37-35, 37-36, 37-37, 38-4, 38
-11, 38-35, 38-36, 38-37, 39-
4, 39-11, 39-35, 39-36, 39-3
7, 40-4, 40-11, 40-35, 40-36,
40-37, 41-4, 41-11, 41-35, 41
-36, 41-37, 42-4, 42-11, 42-3
5, 42-36, 42-37, 43-4, 43-11,
43-35, 43-36, 43-37, 44-4, 44
-11, 44-35, 44-36, 44-37, 45-
4, 45-11, 45-35, 45-36, 45-3
7, 47-4, 47-11, 47-35, 47-36,
47-37, 49-4, 49-11, 49-35, 49
-36, 49-37, 50-4, 50-11, 50-3
5, 50-36, 50-37, 51-4, 51-11,
51-35, 51-36, 51-37, 52-4, 52
-11, 52-35, 52-36, 52-37, 53-
4, 53-11, 53-35, 53-36, 53-3
7, 54-4, 54-11, 54-35, 54-36,
54-37, 66-6, 66-8, 66-10, 67-
6, 67-8, 68-2.

(5) More preferably, Exemplified Compound Nos. 2-15, 2-17, 2-19, 2-21, 2-23,
2-35, 2-37, 2-39, 2-95, 2-96,
2-97, 2-98, 2-99, 2-100, 2-10
1, 2-102, 2-103, 2-104, 2-10
5, 2-108, 2-183, 2-185, 2-18
7, 2-189, 2-195, 3-15, 3-17, 3
-19, 3-21, 3-23, 3-35, 3-37, 3
-39, 3-95, 3-96, 3-97, 3-98, 3
-99, 3-100, 3-101, 3-102, 3-1
03, 3-104, 3-105, 3-108, 3-18
3, 3-185, 3-187, 3-189, 3-19
5, 6-15, 6-35, 6-37, 6-39, 24-
4, 24-11, 24-35, 24-36, 24-3
7, 25-4, 25-11, 25-35, 25-36,
25-37, 26-4, 26-11, 26-35, 26
-36, 26-37, 27-4, 27-11, 27-3
5, 27-36, 27-37, 28-4, 28-11,
28-35, 28-36, 28-37, 31-4, 31
-11, 31-35, 31-36, 31-37, 32-
4, 32-11, 32-35, 32-36, 32-3
7, 42-4, 42-11, 42-35, 42-36,
42-37, 43-4, 43-11, 43-35, 43
-36, 43-37, 44-4, 44-11, 44-3
5, 44-36, 44-37, 45-4, 45-11,
45-35, 45-36, 45-37, 47-4, 47
-11, 47-35, 47-36, 47-37, 49-
4, 49-11, 49-35, 49-36, 49-3
7, 50-4, 50-11, 50-35, 50-36,
50-37, 51-4, 51-11, 51-35, 51
-36, 51-37, 52-4, 52-11, 52-3
5, 52-36, 52-37, 53-4, 53-11,
53-35, 53-36, 53-37, 54-4, 54
-11, 54-35, 54-36, 54-37, 66-
6, 66-8, 66-10, 67-6, 67-8, 68
-2.

(6) More preferably, Exemplified Compound Nos. 2-15, 2-23, 2-35, 2-37, 2-39,
2-95, 2-96, 2-97, 2-98, 2-10
5, 3-15, 3-23, 3-35, 3-37, 3-3
9, 3-95, 3-96, 3-97, 3-98, 3-1
05, 6-15, 6-35, 6-37, 24-4, 24
-11, 24-35, 24-36, 25-4, 25-1
1, 25-35, 25-36, 26-4, 26-11,
26-35, 26-36, 27-4, 27-11, 27
-35, 27-36, 28-4, 28-11, 28-3
5, 28-36, 31-4, 31-11, 31-35,
31-36, 32-4, 32-11, 32-35, 32
-36, 42-4, 42-11, 42-35, 42-3
6, 43-4, 43-11, 43-35, 43-36,
44-4, 44-11, 44-35, 44-36, 45
-4, 45-11, 45-35, 45-36, 47-
4, 47-11, 47-35, 47-36, 49-4,
49-11, 49-35, 49-36, 50-4, 50
-11, 50-35, 50-36, 66-8, 66-1
0, 67-6, 67-8, 68-2.

(7) More preferably, Exemplified Compound No. 2-15) 2-ethoxy-3- [4- [2-[[1-
(4-biphenylyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2-23) 2-ethoxy-3- [4- [2-[[1-
(4-phenylsulfonylphenyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2-35) 2-ethoxy-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2-37) 2-ethoxy-3- [4- [2-[[1-
[4- (3-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2-39) 2-ethoxy-3- [4- [2-[[1-
[4- (4-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2-95) 2-ethoxy-3- [4- [2-[[1-
(2-phenyl-5-pyridyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2-96) 2-ethoxy-3- [4- [2-[[1-
(2-methoxy-5-pyridyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2-97) 2-ethoxy-3- [4- [2-[[1-
(2-ethoxy-5-pyridyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2-98) 2-ethoxy-3- [4- [2-[[1-
(2-isopropoxy-5-pyridyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2-105) 3- [4- [2-[[1- (2-benzyl-5-pyridyl) ethylidene] amino ] Oxy] ethoxy] phenyl] -2-ethoxypropionic acid, 6-35) 2-methoxy-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 24-35) 2-propoxy-3- [4- [2-[[1
-[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 25-35) 2-isopropoxy-3- [4- [2-
[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 26-35) 2-methylthio-3- [4- [2-[[1
-[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 27-35) 2-ethylthio-3- [4- [2-[[1
-[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 28-35) 2-propylthio-3- [4- [2-
[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 31-35) 2-phenylthio-3- [4- [2-
[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 32-4) 3- [4- [2-[[1- (4-Biphenylyl) ethylidene] amino [Oxy] ethoxy] phenyl] -2- (phenylamino) propionic acid, 32-35) 2-phenylamino-3- [4- [2-
[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 42-35) 2-methylamino-3- [4- [2-
[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 43-35) 2-ethylamino-3- [4- [2-
[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 44-35) 2-Propylamino-3- [4- [2-
[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 45-35) 2-isopropylamino-3- [4- [2
-[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 47-35) 2- (N, N-diethylamino) -3-
[4- [2-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl]
Propionic acid, 49-4) 3- [4- [2-[[1- (4-biphenylyl) ethylidene] aminooxy] ethoxy] phenyl] -2- [N-phenyl-N-ethylamino] propionic acid, 50 -4) 3- [4- [2-[[1- (4-biphenylyl) ethylidene] aminooxy] ethoxy] phenyl] -2-pyrrolylpropionic acid, 66-8) 2- (3-phenylpropyl)- 3- [4
-[2-[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 66-10) 2- (4-phenylbutyl) -3- [4-
[2-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 67-6) 2-propyl-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 67-8) 2-butyl-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid or 68-2) 2-phenoxy-3- [4- [2-[[1
-[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid.

(8) Most preferably, Exemplified Compound No. 2-15) 2-ethoxy-3- [4- [2-[[1-
(4-Biphenylyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2-35) 2-ethoxy-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 26-35) 2-methylthio-3- [4- [2-[[1
-[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 31-35) 2-phenylthio-3- [4- [2-
[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 32-4) 3- [4- [2-[[1- (4-Biphenylyl) ethylidene] amino [Oxy] ethoxy] phenyl] -2- (phenylamino) propionic acid, 43-35) 2-ethylamino-3- [4- [2-
[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 66-8) 2- (3-phenylpropyl) -3- [4
-[2-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 67-8) 2-Butyl-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid or 68-2) 2-phenoxy-3- [4- [2-[[1
-[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid.

[0207]

BEST MODE FOR CARRYING OUT THE INVENTION The phenylalkylcarboxylic acid derivative having the above general formula (I), its pharmacologically acceptable salt or its pharmacologically acceptable ester of the present invention can be easily produced according to the following Method A. You.

<< Method A >>

[0209]

Embedded image

In the above formula, R ¹ , R ² , R ³ , X, Y and Z have the same meanings as described above, and W ¹ is the amino group when W represents a primary or secondary amino group. When the group represents an amino group protected by a usual protecting group such as t-butoxycarbonyl, and W ¹ represents another group, W ¹ represents W
And M represents an ester residue when the phenylalkylcarboxylic acid having the above general formula (I) forms an ester, and U represents a hydroxyl group, a halogen atom (preferably a chlorine atom or a bromine atom). Atom, iodine atom) or formula
A group having —O—SO ₂ —R ⁵ , wherein R ⁵ is an alkyl group having 1 to 6 carbon atoms such as methyl or ethyl;
A halogenated alkyl group having two or more; or phenyl, p
Alkyl having 1 to 4 carbons as a substituent such as tolyl, p-nitrophenyl or p-bromophenyl, nitro or aryl having 6 to 10 carbons which may have a halogen) Show.

Step A1 Step A1 is a step of producing a compound having the general formula (IV), and reacting the compound having the general formula (II) with the compound having the general formula (III). Manufactured by

When U is a hydroxyl group, the usual Mitsunobu reaction [O. Mitsunobu, Synthesis, p.
Year)].

The reaction is usually carried out by bringing an azo compound into contact with a phosphine in the presence of a solvent.
As the azo compounds of the reaction reagent, C ₁ -C ₄ alkyl azodicarboxylates such as diethyl azodicarboxylate,
Azodicarboxamides such as 1,1 '-(azodicarbonyl) dipiperidine are used. Examples of the phosphines include triarylphosphines such as triphenylphosphine and tri (C) such as tributylphosphine.
Such as ₁ -C ₄ alkyl) phosphine is used.

The reaction is generally and preferably effected in the presence of a solvent. The solvent to be used is not particularly limited as long as it does not affect the reaction, and examples thereof include hydrocarbons such as benzene, toluene, xylene, hexane, and heptane; chloroform, methylene chloride, carbon tetrachloride, and 1,2- Halogenated hydrocarbons such as dichloroethane; ethers such as diethyl ether, tetrahydrofuran and dioxane; amides such as dimethylformamide, dimethylacetamide and hexamethylphosphoric triamide; or a mixed solvent thereof is preferably used. , Preferably hydrocarbons, halogenated hydrocarbons or ethers.
The reaction temperature is from 10 ° C to 100 ° C, preferably 2 ° C.
0 ° C to 80 ° C.

The reaction time varies depending on the reaction reagent, reaction temperature, solvent and the like, but is usually 1 hour to 3 days, preferably 5 hours to 2 days.

U is a halogen atom or a group represented by the formula —O—SO ₂
When it is a group having —R ⁵ (wherein R ⁵ has the same meaning as described above), the reaction is carried out in an inert solvent in the presence of a base.

The base used is preferably an alkali metal carbonate such as sodium carbonate or potassium carbonate; an alkali metal hydride such as sodium hydride, potassium hydride or lithium hydride; sodium methoxide, sodium Alkali metal alkoxides such as ethoxide, potassium t-butoxide, lithium methoxide; alkyl lithiums such as butyl lithium and methyl lithium; lithium amides such as lithium diethylamide, lithium diisopropylamide, lithium bis (trimethylsilyl) amide; Alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; or 1,5-diazabicyclo [4.3.0] non-5-ene, 1,8-diazabicyclo [5.4.0] undeca-
A tertiary organic amine such as 7-ene, N, N-diisopropylethylamine; more preferably an alkali metal carbonate, alkali metal hydride or alkali metal alkoxide;

The inert solvent used in the reaction is not particularly limited as long as it does not participate in the reaction. Examples thereof include hydrocarbons such as benzene and toluene; ethers such as tetrahydrofuran and dioxane; methanol, ethanol, and t.
Alcohols such as butanol; amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidinone; ketones such as acetone and 2-butanone; nitriles such as acetonitrile; sulfoxides such as dimethylsulfoxide; Or a mixed solvent thereof, preferably an ether, an amide, a ketone or a sulfoxide.

When this reaction is carried out in the presence of a phase transfer catalyst such as benzyltriethylammonium iodide or tetrabutylammonium iodide, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide is used as a base. It is carried out in a two-layer solvent of water and halogenated hydrocarbons such as methylene chloride and chloroform.

[0220] The reaction temperature is from -10 ° C to 120 ° C, preferably from 10 ° C to 100 ° C.

The reaction time varies depending on the reagent used, the reaction temperature and the like, but is 30 minutes to 48 hours, preferably 1 hour to 16 hours.

When W ¹ represents a primary or secondary amino group protected by a usual protecting group such as t-butoxycarbonyl, after the reaction is completed, a known method such as an acid such as hydrochloric acid is used. For 30 minutes to 2 hours at room temperature for deprotection.

Step A2 Step A2 is a step of producing a phenylalkylcarboxylic acid derivative having the general formula (I), and removing the ester residue of the compound having the general formula (IV). Will be

This step is achieved by hydrolysis with a base in the presence of a solvent. The solvent used in this reaction is not particularly limited as long as it does not affect the reaction, and examples thereof include ethers such as diethyl ether, tetrahydrofuran and dioxane; alcohols such as methanol and ethanol; water; Is preferably used.

Examples of the base used in the reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate. can give. Preferably, it is an alkali metal hydroxide.

The reaction temperature varies depending on the solvent and the base used, but is from 0 ° C. to 100 ° C., preferably from 10 ° C.
To 80 ° C.

The reaction time varies depending on the solvent, base, reaction temperature and the like used, but is usually from 10 minutes to 24 hours, preferably from 30 minutes to 16 hours.

In this step, when the ester residue is a t-butyl group, diphenylmethyl group or p-methoxybenzyl group, formic acid, acetic acid, trifluoroacetic acid, methanesulfone It is also carried out by reacting with an acid, an organic acid such as benzenesulfonic acid, p-toluenesulfonic acid or trifluoromethanesulfonic acid, or a mineral acid such as hydrochloric acid or sulfuric acid. Preferably it is trifluoroacetic acid or hydrochloric acid.

In the present reaction, when a solvent is used, it is not particularly limited as long as it does not affect the reaction, and examples thereof include hydrocarbons such as benzene, toluene, xylene, hexane and heptane; chloroform, methylene chloride, and the like. Halogenated hydrocarbons such as carbon tetrachloride; ethers such as diethyl ether, tetrahydrofuran and dioxane; alcohols such as methanol and ethanol;
Amides such as dimethylformamide, dimethylacetamide and hexamethylphosphoric triamide; esters such as methyl acetate and ethyl acetate; water; or a mixed solvent thereof. Preferred are ethers.

The reaction temperature varies depending on the acid used, but is from -10 ° C to 120 ° C, preferably from 0 ° C to 100 ° C.

The reaction time varies depending on the acid used, the reaction temperature and the like, but is usually from 10 minutes to 24 hours.
Preferably it is 30 minutes to 16 hours.

In this step, when the ester residue is an aralkyl group such as a benzyl group or a diphenylmethyl group,
The reaction is also carried out by subjecting a compound having the general formula (IV) to a catalytic hydrogenation reaction. The catalyst used includes, for example, palladium-carbon, palladium black, platinum oxide, platinum black and the like, and is preferably palladium-carbon.

The reaction is generally and preferably effected in the presence of a solvent. The solvent used is not particularly limited as long as it does not affect the reaction, and examples thereof include hydrocarbons such as benzene, toluene, xylene, hexane, and heptane; and halogenated carbons such as chloroform, methylene chloride, and carbon tetrachloride. Hydrogens; ethers such as diethyl ether, tetrahydrofuran and dioxane; alcohols such as methanol, ethanol and isopropanol; amides such as dimethylformamide, dimethylacetamide and hexamethylphosphoric triamide; carboxylic acids such as formic acid and acetic acid Acids; or a mixed solvent thereof is used.
Preferably, they are alcohols.

The reaction temperature is from 10 ° C. to 140 ° C.
Preferably it is 20 ° C to 120 ° C.

The reaction time varies depending on the reaction reagent, reaction temperature, solvent and the like, but is usually 30 minutes to 3 days, preferably 1 hour to 1 day.

The compound having the general formula (IV) in Method A can also be produced according to Method B.

<< Method B >>

[0238]

Embedded image

In the above formula, R ¹ , R ² , R ³ , U, X,
Y, Z, W and M have the same meaning as described above.

Step B1 in Method B is a step for producing a compound having the general formula (IV), and reacting the compound having the general formula (V) with the compound having the general formula (VI). This is done by:

This reaction is carried out in the same manner as in Step A1 of Method A described in detail above.

The phenylalkylcarboxylic acid derivative having the general formula (I) of the present invention and the general formula (IV)
Can also be produced according to the following Method C.

<< Method C >>

[0244]

Embedded image

In the above formula, R ¹ , R ² , R ³ , U, X,
Y, W, W ¹ and M have the same meaning as described above.

R ⁶ represents a hydrogen atom and R ⁷ represents an amino-protecting group, or R ⁶ and R ⁷ together represent an amino-protecting group.

The protecting group for the amino group of R ⁷ is a protecting group well known in organic synthetic chemistry, for example, a C ₇ -C ₁₄ aralkyl group such as benzyl, diphenylmethyl, and trityl; formyl, trifluoroacetyl A C ₁ -C ₄ aliphatic acyl group which may be substituted by fluorine, such as
- butoxy C ₁ -C ₄ alkoxycarbonyl groups such as carbonyl; benzyloxycarbonyl, p- methoxybenzyloxycarbonyl or p- nitro methoxy or good benzyloxycarbonyl group optionally substituted with nitro, such as benzyloxycarbonyl; When R ⁶ and R ⁷ together represent an amino-protecting group, examples thereof include a phthaloyl group and the like, preferably benzyl, trityl, t-butoxycarbonyl, benzyloxycarbonyl or phthaloyl. is there.

Step C1 Step C1 is a step of producing a compound having the general formula (VIII), and reacting the compound having the general formula (VII) with the compound having the general formula (III). Done by

This step is performed in the same manner as in step A1 of method A.

Step C2 Step C2 is a step of producing a compound having the general formula (IX), and removing the amino-protecting group R ⁷ in the compound having the general formula (VIII). Done.

The deprotection reaction of a group in which the protecting group R ⁷ can be removed by catalytic reduction such as an aralkyl group or an aralkyloxycarbonyl group, or a group which can be removed by an acid such as a trityl group or t-butoxycarbonyl group is carried out by the method described in Method A. No. A
This is performed in the same manner as in the two steps.

When the protecting group R ⁷ is an aliphatic acyl group such as formyl or trifluoroacetyl, it is removed under basic conditions.

Examples of the base used include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide; and alkali metal carbonates such as sodium carbonate and potassium carbonate. Preferably, it is an alkali metal hydroxide.

This reaction is suitably carried out in an inert solvent such as alcohols such as methanol and ethanol; water; ethers such as tetrahydrofuran and dioxane; or a mixed solvent thereof. More preferred are alcohols.

The reaction temperature is between 0 ° C. and 100 ° C.
Preferably it is 10 ° C to 80 ° C.

The reaction time varies depending on the reaction reagent, reaction temperature, solvent and the like, but is usually 30 minutes to 24 hours, preferably 1 hour to 16 hours.

When R ⁶ and R ⁷ are taken together and the protecting group for the amino group is a phthaloyl group, the protecting group can be removed by treating with a hydrazine or a primary amine.

The hydrazines used include, for example, hydrazine, methylhydrazine, phenylhydrazine and the like, and hydrazine is preferred. Examples of the primary amine used include methylamine, ethylamine, propylamine, butylamine, isobutylamine, pentylamine and hexylamine, and propylamine or butylamine is preferred.

This reaction is carried out by using an inert agent such as methanol,
Alcohols such as ethanol; ethers such as tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; or mixed solvents thereof are preferably used. Preferably, they are alcohols.

The reaction temperature is between 0 ° C. and 100 ° C.
Preferably it is 10 ° C to 80 ° C.

The reaction time varies depending on the reaction reagent, reaction temperature, solvent and the like, but is usually 30 minutes to 24 hours, preferably 1 hour to 16 hours.

Step C3 Step C3 is a step for producing a compound having the general formula (IV), wherein the amino compound having the general formula (IX) and the carbonyl compound having the general formula (X) are dehydrated. This is performed by a condensation reaction.

This step is performed in an inert solvent. The inert solvent used is not particularly limited as long as it does not participate in the reaction. For example, hydrocarbons such as hexane, benzene and xylene; methylene chloride, chloroform, 1, 2
Halogenated hydrocarbons such as dichloroethane; ethers such as tetrahydrofuran and dioxane; alcohols such as methanol and ethanol; esters such as ethyl acetate and butyl acetate; amides such as dimethylformamide and dimethylacetamide. And preferably hydrocarbons, halogenated hydrocarbons, ethers or alcohols.

The reaction temperature is between 0 ° C. and 120 ° C.
Preferably it is 10 ° C to 100 ° C.

The reaction time varies depending on the reaction reagent, reaction temperature, solvent and the like, but is usually 30 minutes to 24 hours, preferably 1 hour to 16 hours.

Step C4 In the step C4, the compound having the above general formula (IV) is protected when W ¹ is an amino group protected by a usual protecting group such as t-butoxycarbonyl. After removing the group, the ester residue is optionally removed to convert the ester residue into a compound having the general formula (I). In the reaction, removal of the protecting group for the amino group is carried out in the same manner as in Step A1 of Method A described above, and removal of the ester residue is carried out in Step A2 of Method A described above.
It is performed in the same manner as the process.

In the method A, the starting material represented by the general formula (I)
The compound having I) can be produced, for example, according to Method D.

<< Method D >>

[0269]

Embedded image

In the above formula, R ¹ , R ² and X have the same meanings as described above, and U ¹ is a halogen atom in U or a group having the formula —O—SO ₂ —R ⁵ (wherein R
⁵ has the same meaning as described above. ).

Formula (IIa) produced by the present method
Compounds having is U in formula (II) is a hydroxyl group compound, a compound having the general formula (IIb) has the general formula U in (II) is a halogen atom or the formula -O-SO ₂ -R ⁵ (Wherein R ⁵ has the same meaning as described above).

Step D1 Step D1 is a step for producing a compound having the general formula (XII), wherein the compound represented by the general formula (V) and the compound represented by the general formula (XI) It is performed by reacting.

In this reaction, U described in Step A1 of Method A is a halogen atom or a compound of the formula —O—SO ₂ —.
The reaction is carried out in the same manner as in the case of a group having R ⁵ (wherein, R ⁵ has the same meaning as described above).

Step D2 Step D2 is a step for producing a compound having the general formula (IIa), and is carried out by removing a tetrahydropyranyl group of the compound having the general formula (XII).

This reaction is carried out in the same manner as in the method for deprotection with an acid described in Step A2 of Method A.

Step D3 Step D3 is a step of producing a compound having the general formula (IIb).
The conversion is carried out by converting into a group having O ₂ -R ⁵ (wherein R ⁵ has the same meaning as described above).

When U ¹ in the compound having the general formula (IIa) is a halogen atom, the reaction is carried out by reacting the compound with a halogenating agent in the presence of a solvent.

The halogenating agent used is thionyl halide such as thionyl chloride or thionyl bromide; phosphorus pentahalide such as phosphorus pentachloride or phosphorus pentabromide; phosphorus oxychloride or phosphorus oxybromide. Phosphorus oxyhalide; oxalyl chloride; and the like, preferably thionyl halide or oxalyl chloride.

The inert solvent used is not particularly limited as long as it does not participate in the reaction. For example, hydrocarbons such as hexane, benzene, toluene and xylene; methylene chloride, chloroform and 1,2-dichloroethane Halogenated hydrocarbons; ethers such as tetrahydrofuran and dioxane; esters such as ethyl acetate and butyl acetate; and preferably halogenated hydrocarbons or ethers.

The reaction temperature is from -10 ° C to 100 ° C, preferably from 10 ° C to 80 ° C.

The reaction time varies depending on the reaction reagent, reaction temperature, solvent and the like, but is usually 30 minutes to 24 hours, preferably 1 hour to 16 hours.

Alternatively, the reaction is carried out according to the above general formula (IIa)
And a carbon tetrahalide such as carbon tetrachloride or carbon tetrabromide, N-bromosuccinimide or N
-Reacting with a halogenating agent such as N-halogenosuccinimide such as chlorosuccinimide in the presence of tri-C ₆ -C ₁₀ aryl or tri-C ₁ -C ₄ alkylphosphines such as triphenylphosphine and tributylphosphine. It is also done by doing. The reaction conditions for this reaction are the same as those for the Mitsunobu reaction described in Step A1 of Method A.

In the compound having the general formula (IIa), U ¹ is a group having the formula —O—SO ₂ —R ⁵ (wherein
R ⁵ has the same meaning as described above. ) In the case where in an inert solvent, in the presence of a base, wherein R ⁵ -SO ₂
A compound having —Cl (wherein R ⁵ has the same meaning as described above) or a compound having the formula (R ⁵ —SO ₂ ) ₂ O (where R ⁵ has the same meaning as described above) Shown.)
The reaction is carried out.

The base used is preferably a tertiary amine such as triethylamine, N-methylmorpholine, N, N-diisopropylethylamine.

The inert solvent used is not particularly limited as long as it does not participate in the reaction. For example, hydrocarbons such as hexane, benzene, toluene and xylene; methylene chloride, chloroform and 1,2-dichloroethane Halogenated hydrocarbons; ethers such as tetrahydrofuran and dioxane; esters such as ethyl acetate and butyl acetate; and preferably halogenated hydrocarbons or ethers.

The reaction temperature is from -10 ° C to 100 ° C, preferably from 0 ° C to 60 ° C.

The reaction time varies depending on the reaction reagent, reaction temperature, solvent and the like, but is usually 30 minutes to 24 hours, preferably 1 hour to 16 hours.

The starting compound having the general formula (V) is a known compound or can be easily produced according to a known method. In general, it is easily produced by a dehydration condensation reaction between a corresponding carbonyl compound and hydroxylamine (for example, New Experimental Chemistry, Vol. 14, (III), 132
5 pages, edited by The Chemical Society of Japan, published by Maruzen Co., Ltd .; "Comprehensive
Organic Functional Group Transformations ", Volume 3,
425, author ARKatritzby et al., Pergamon Publishing (UK), 1995, etc.).

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, 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.

The phenylalkylcarboxylic acid derivative having the above general formula (I), its pharmacologically acceptable salt or its pharmacologically acceptable ester of the present invention has excellent insulin resistance-improving action, anti-inflammatory action, and immunological action. Has a regulatory action, an aldose reductase inhibitory action, a 5-lipoxygenase inhibitory action, a lipid peroxide production inhibitory action, a PPAR activating action and an anti-osteoporosis action, for example, diabetes, hyperlipidemia, obesity, impaired glucose tolerance, insulin Resistant glucose intolerance, hypertension, fatty liver, diabetic complications (eg retinopathy, nephropathy,
Neurosis, cataract, coronary artery disease, etc.), arteriosclerosis, gestational diabetes, polycystic ovary syndrome, cardiovascular disease (eg, ischemic heart disease, etc.), cells caused by atherosclerosis or ischemic heart disease. Diseases primarily due to insulin resistance, such as damage (eg, brain injury caused by stroke); osteoarthritis, pain, fever, rheumatoid arthritis, inflammatory bowel disease, acne, sunburn, psoriasis, eczema, allergy It is useful as a prophylactic and / or therapeutic agent (particularly a therapeutic agent) for sexual diseases, asthma, GI ulcers, cancer, cachexia, autoimmune diseases, and inflammatory diseases such as pancreatitis; osteoporosis; cataracts and the like.

The phenylalkylcarboxylic acid derivative having the above general formula (I), its pharmaceutically acceptable salt or its ester of the present invention 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 preparations are prepared by using known auxiliaries which can be usually used in the field of known pharmaceutical preparations such as excipients, binders, disintegrants, lubricants, dissolving agents, flavoring agents, coating agents, etc. It can be formulated.

In the case of molding into tablets, carriers conventionally known in the art can be widely used, such as lactose, sucrose, sodium chloride, glucose, urea, starch, and the like.
Binding of excipients such as calcium carbonate, kaolin, crystalline cellulose, silicic acid, water, ethanol, propanol, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethylcellulose, shellac, methylcellulose, potassium phosphate, polyvinylpyrrolidone sugar Agent, dried starch, sodium alginate, agar powder, laminaran powder, sodium hydrogen carbonate, calcium carbonate, polyoxyethylene sorbitan fatty acid esters, sodium lauryl sulfate, monoglyceride stearate, starch, disintegrators such as lactose, sucrose, stearin, cacao Disintegration inhibitors such as butter and hydrogenated oil; quaternary ammonium bases; absorption promoters such as 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 form of pills, carriers conventionally known in the art can be widely used as carriers, for example, excipients such as glucose, lactose, starch, cocoa butter, hydrogenated vegetable oils, kaolin, talc, and the like. Examples thereof include rubber powder, tragacanth powder, binders such as gelatin and ethanol, and disintegrants such as laminaran agar. In molding into suppository form, those conventionally known in the art can be widely used as carriers, for example, polyethylene glycol, cocoa butter, higher alcohols, higher alcohol esters, gelatin, semi-synthetic glycerides and the like. it can.

When prepared as an injection, the liquid preparations and suspensions 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 a normal solubilizing agent, a buffer, a soothing agent, etc. 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. Is appropriate.

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

[0298]

EXAMPLES The present invention will be described in more detail with reference to Examples, Production Examples, Reference Examples and Formulation Examples, but the present invention is not limited thereto.

Production Example 1 2-ethoxy-3- [4- [2
-[[1- [4- (2-pyridyl) phenyl] ethylide
[Aminooxy] ethoxy] phenyl] propionic acid
Ethyl (Ethyl ester of Exemplified Compound No. 2-35) Ethyl 2-ethoxy-3- (4-hydroxyphenyl) propionate 242 mg of a 55% oily sodium hydride 49 mg in a mixed solution of N, N-dimethylformamide 4 ml and toluene 2 ml The mixture was stirred at room temperature for 30 minutes. To this solution, 340 mg of 4 ′-(2-pyridyl) acetophenone oxime O-2- (methanesulfonyloxy) ethyl ether obtained in Reference Example 2
-Dimethylformamide 3 ml solution is added dropwise,
For 3 hours. After completion of the reaction, ethyl acetate and water were added to the reaction solution, the ethyl acetate layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Silica gel column chromatography of the residue (ethyl acetate: hexane = 3: 7)
373 mg of the target compound was obtained in the form of a syrup. This compound crystallized on standing.

1) Melting point 59-61 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) in deuterated chloroform as an internal standard
¹ H-nuclear magnetic resonance spectrum (27
0 MHz) is as follows. 1.16 (3H, t, J = 7 Hz), 1.23 (3H, t, J = 7 Hz), 2.28
(3H, s), 2.95 (2H, d, J = 6.5 Hz), 3.29-3.40 (1H,
m), 3.54-3.65 (1H, m), 3.97 (1H, t, J = 6.5 Hz), 4.
17 (2H, q, J = 7 Hz), 4.28 (2H, t, J = 5 Hz), 4.55 (2
H, t, J = 5 Hz), 6.88 (2H, d, J = 8.5 Hz), 7.16 (2H,
d, J = 8.5 Hz), 7.22-7.27 (1H, m), 7.75-7.80 (2H,
m), 7.76 (2H, d, J = 8.5 Hz), 8.01 (2H, d, J = 8.5 H
z), 8.70 (1H, d, J = 5 Hz).

Production Example 2 2-ethoxy-3- [4- [2
-[[1- [4- (2-pyridyl) phenyl] ethylide
[Aminooxy] ethoxy] phenyl] propionic acid (Exemplified Compound No. 2-35) 2-ethoxy-3- [4- [2-] obtained in Production Example 1
To a solution of 310 mg of ethyl [[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionate and 5 ml of ethanol was added 1.30 ml of a 1N aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 1.5 hours. Stirred. After completion of the reaction, ethanol was distilled off from the reaction mixture under reduced pressure, and the pH was adjusted to 3 by adding 1N hydrochloric acid. The obtained product was extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crude crystalline target compound was washed with isopropyl ether and hexane to obtain 232 mg of the target compound. .

1) Melting point 133-135 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) in deuterated chloroform as an internal standard
¹ H-nuclear magnetic resonance spectrum (27
0 MHz) is as follows. 1.18 (3H, t, J = 7 Hz), 2.28 (3H, s), 2.95 (1H, d,
d, J = 7.5, 14 Hz), 3.08 (1H, d, d, J = 4.5, 14 Hz),
3.39-3.50 (1H, m), 3.55-3.66 (1H, m), 4.04 (1H, d,
d, J = 4.5, 7.5 Hz), 4.29 (2H, t, J = 5 Hz), 4.56 (2
H, t, J = 5Hz), 6.89 (2H, d, J = 8.5 Hz), 7.17 (2H,
d, J = 8.5 Hz), 7.25-7.30 (1H, m), 7.74 (2H, d, J = 8.
5 Hz), 7.76-7.80 (2H, m), 7.96 (2H, d, J = 8.5Hz),
8.72 (1H, d, J = 4.5 Hz).

Production Example 3 2-Phenylthio-3- [4-
[2-[[1- [4- (2-pyridyl) phenyl] ethyl]
[Ridene] aminooxy] ethoxy] phenyl] propio
Phosphate methyl (Compound methyl ester No. 31-35) obtained in Reference Example 1 2 - [[1- [4- (2-pyridyl) phenyl] ethylidene] aminoxy] ethanol 256 mg, obtained in Reference Example 7 Methyl 3- (4-hydroxyphenyl) -2- (phenylthio) propionate 288 mg, triphenylphosphine 289 mg
And 5 ml of tetrahydrofuran in a toluene solution of 222 mg of diethyl azodicarboxylate 3.3 m
1 was added dropwise. After stirring at room temperature for 18 hours, the reaction solution was concentrated, and the obtained residue was subjected to silica gel column chromatography twice (ethyl acetate: hexane = 1: 2 and ethyl acetate: benzene = 1: 4) to give a syrup. 366 mg of the desired compound in the form of were obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 2.27 (3H, s), 3.00 (1H, d, d, J = 6, 14 Hz), 3.14 (1
H, d, d, J = 9, 14 Hz), 3.58 (3H, s), 3.86 (1H, d, d,
J = 6, 9 Hz), 4.27 (2H, t, J = 5 Hz), 4.55 (2H, t, J =
5 Hz), 6.87 (2H, d, J = 8.5 Hz), 7.10 (2H, d, J = 8.5
Hz), 7.22-7.34 (4H, m), 7.41-7.45 (2H, m), 7.72
7.80 (2H, m), 7.76 (2H, d, J = 8.5Hz), 8.01 (2H,
d, J = 8.5 Hz), 8.71 (1H, d, J = 4.5 Hz).

Production Example 4 2-Phenylthio-3- [4-
[2-[[1- [4- (2-pyridyl) phenyl] ethyl]
[Ridene] aminooxy] ethoxy] phenyl] propio
Acid (Exemplified Compound No. 31-35) 2-Phenylthio-3- [4- [2] obtained in Production Example 3
To a mixed solution of 350 mg of methyl [-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionate, 3 ml of methanol and 2 ml of dioxane was added 2.00 ml of a 1N aqueous sodium hydroxide solution. Stirred at C for 4 hours. After completion of the reaction, the reaction solution was concentrated, diluted with water, adjusted to pH 3 by adding 1N hydrochloric acid, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated to obtain 324 mg of the target compound as a foamy solid.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 2.24 (3H, s), 3.01 (1H, d, d, J = 6, 14 Hz), 3.15 (1
H, d, d, J = 9.5, 14 Hz), 3.87 (1H, d, d, J = 6, 9.5
Hz), 4.30 (2H, t, J = 5 Hz), 4.54 (2H, t, J = 5 Hz),
6.87 (2H, d, J = 8.5 Hz), 7.13 (2H, d, J = 8.5 Hz), 7.
23-7.32 (4H, m), 7.43-7.49 (2H, m), 7.64 (2H, d, J
= 8.5 Hz), 7.68-7.80 (2H, m), 7.85 (2H, d, J = 8.5
Hz), 8.66 (1H, d, J = 5.5 Hz).

Production Example 5 2-phenylamino-3- [4
-[2-[[1- [4- (2-pyridyl) phenyl] d
Tylidene] aminooxy] ethoxy] phenyl] propy
Ethyl onoate (ethyl ester of Exemplified Compound No. 32-35) 256 mg of 2-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethanol obtained in Reference Example 1, obtained in Reference Example 5 285 mg of ethyl 3- (4-hydroxyphenyl) -2- (phenylamino) propionate, 289 m of triphenylphosphine
g and 222 mg of diethyl azodicarboxylate were reacted and worked up according to Production Example 3 to obtain 375 mg of a crystalline target compound.

1) Melting point 140 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) as an internal standard in deuterated chloroform
¹ H-nuclear magnetic resonance spectrum (27
0 MHz) is as follows. 1.19 (3H, t, J = 7 Hz), 2.28 (3H, s), 3.00-3.14 (2
H, m), 4.13 (2H, q, J = 7 Hz), 4.15 (1H, brs), 4.26
-4.34 (3H, m), 4.55 (2H, t, J = 5 Hz), 6.60 (2H,
d, J = 8.5 Hz), 6.73 (1H, t, J = 7.5 Hz), 6.88 (2H, d,
J = 8.5 Hz), 7.09 (2H, d, J = 8.5 Hz), 7.13-7.27 (3H,
m), 7.75-7.78 (2H, m), 7.76 (2H, d, J = 8.5 Hz),
8.01 (2H, d, J = 8.5 Hz), 8.71 (1H, d, J = 4.5 Hz).

Production Example 6 2-phenylamino-3- [4
-[2-[[1- [4- (2-pyridyl) phenyl] d
Tylidene] aminooxy] ethoxy] phenyl] propy
Ononic acid (Exemplified Compound No. 32-35) 2-phenylamino-3- [4- obtained in Production Example 5
According to Production Example 4, using 260 mg of ethyl [2-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionate and 1.00 ml of 1N aqueous sodium hydroxide, The reaction was performed. After completion of the reaction, the reaction solution was concentrated and diluted with water, and the pH was adjusted to 4 with 1N hydrochloric acid, and the precipitated crude target compound was collected by filtration. The obtained crude target compound was washed with water and isopropyl ether to obtain 224 m of the target compound.
g was obtained.

1) Melting point: 149-152 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) in deuterated chloroform as an internal standard
¹ H-nuclear magnetic resonance spectrum (27
0 MHz) is as follows. 2.27 (3H, s), 3.04 (1H, d, d, J = 6.5, 14 Hz), 3.17
(1H, d, d, J = 5.5, 14 Hz), 4.25-4.30 (3H, m), 4.54
(2H, t, J = 5 Hz), 6.60 (2H, d, J = 8 Hz), 6.69 (1H,
d, J = 7.5 Hz), 6.87 (2H, d, J = 8.5 Hz), 7.12-7.17
(4H, m), 7.25-7.30 (1H, m), 7.76 (2H, d, J = 8.5 H
z), 7.77-7.83 (2H, m), 8.01 (2H, d, J = 8.5 Hz), 8.
71 (1H, d, J = 4.5 Hz).

Production Example 7 2- (N, N-diethylamido)
No) -3- [4- [2-[[1- [4- (2-pyridi
Ru) phenyl] ethylidene] aminooxy] ethoxy]
Phenyl] ethyl propionate (Exemplified Compound No. 47
Ethyl ester of -35) 337 mg of 4 '-(2-pyridyl) acetophenone oxime O-2- (methanesulfonyloxy) ethyl ether obtained in Reference Example 2;
Ethyl (N, N-diethylamino) -3- (4-hydroxyphenyl) propionate 243 mg and 55%
The reaction and after-treatment were carried out according to Production Example 1 using 44 mg of oily sodium hydride to obtain 481 mg of the target compound in the form of a syrup.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 1.02 (6H, t, J = 7 Hz), 1.16 (3H, t, J = 7 Hz), 2.28
(3H, s), 2.52 (2H, sextet, J = 7 Hz), 2.78 (2H, sex
tet, J = 7 Hz), 2.80 (1H, d, d, J = 6, 13.5 Hz), 3.01
(1H, d, d, J = 9, 13.5 Hz), 3.56 (1H, d, d, J = 6, 9 H
z), 4.00-4.14 (2H, m), 4.27 (2H, t, J = 5 Hz), 4.55
(2H, t, J = 5 Hz), 6.86 (2H, d, J = 8.5 Hz), 7.12 (2
H, d, J = 8.5 Hz), 7.22-7.27 (1H, m), 7.75-7.78 (4
H, m), 8.01 (2H, d, J = 8.5 Hz), 8.70 (1H, d, J = 4.5
Hz).

Production Example 8 2- (N, N-diethylamido)
No) -3- [4- [2-[[1- [4- (2-pyridi
Ru) phenyl] ethylidene] aminooxy] ethoxy]
Phenyl] propionic acid (Exemplary Compound No. 47-3
5) 2- (N, N-diethylamino)-obtained in Production Example 7
474 mg of ethyl 3- [4- [2-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionate, methanol 5
2.75 ml of a 1N aqueous sodium hydroxide solution was added to a mixed solution of 3 ml of dioxane and 3 ml of dioxane.
Stirred for hours. After completion of the reaction, methanol and dioxane were distilled off from the reaction mixture under reduced pressure, and the mixture was diluted with water. Then, 2.75 ml of 1N hydrochloric acid was added to adjust the pH to 4, and the precipitated crude target compound was collected by filtration. The obtained crude target compound was washed with water and isopropyl ether to obtain 440 mg of the target compound. 1) Melting point 157-159 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated dimethyl sulfoxide using TMS (tetramethylsilane) as an internal standard. Is as follows. 0.96 (6H, t, J = 7 Hz), 2.23 (3H, s), 2.54-2.78 (5
H, m), 2.96 (1H, d, d, J = 7.5, 14 Hz), 3.48 (1H, t,
J = 7 Hz), 4.25 (2H, t, J = 5 Hz), 4.46 (2H, t, J = 5 H
z), 6.88 (2H, d, J = 8.5 Hz), 7.16 (2H, d, J = 8.5 H
z), 7.35-7.40 (1H, m), 7.80 (2H, d, J = 8.5 Hz), 7.
90 (1H, d, t, J = 1.5, 7.5 Hz), 8.01 (1H, d, J = 8 H
z), 8.13 (2H, d, J = 8.5 Hz), 8.68 (1H, d, J = 4 Hz)
.

Production Example 9 3- [4- [2-[[1- (4
-Biphenylyl) ethylidene] aminooxy] ethoxy
[S] phenyl] -2- (phenylamino) propionic acid
Ethyl (ethyl ester of Exemplified Compound No. 32-4) 2-[[1- (4-biphenylyl)) obtained in Reference Example 3.
179 mg of ethylidene] aminooxy] ethanol,
3- (4-hydroxyphenyl)-obtained in Reference Example 5
Ethyl 2- (phenylamino) propionate 200m
g, 183 mg of triphenylphosphine and 122 mg of diethyl azodicarboxylate were reacted and worked up according to Production Example 3 to obtain 282 mg of the target compound in the form of a syrup.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 1.19 (3H, t, J = 7 Hz), 2.27 (3H, s), 3.00-3.14 (2
H, m), 4.12 (2H, d, q, J = 1, 7 Hz), 4.25-4.33 (3H,
m), 4.54 (2H, t, J = 5 Hz), 6.60 (2H, d, J = 8.5 Hz),
6.73 (1H, t, J = 7.5 Hz), 6.88 (2H, d, J = 8.5 Hz),
7.08 (2H, d, J = 8.5 Hz), 7.16 (2H, t, J = 7.5 Hz), 7.
33-7.48 (3H, m), 7.58-7.61 (4H, m), 7.70-7.74 (2H,
m).

Production Example 10 3- [4- [2-[[1-
(4-Biphenylyl) ethylidene] aminooxy] eth
[Xy] phenyl] -2- (phenylamino) propion
Acid (Exemplified Compound No. 32-4) 3- [4- [2-[[1- (4-biphenylyl) ethylidene] aminooxy] ethoxy] phenyl] -2- (phenylamino) propion obtained in Production Example 9 A solution of lithium hydroxide monohydrate 72 mg and water 3 ml was added to a solution of ethyl acid 282 mg and dioxane 3 ml, and the mixture was stirred at 60 ° C. for 1 hour. After completion of the reaction, the reaction solution was concentrated and diluted with water. Then 1N hydrochloric acid 1.7 was added.
1 ml was added and the resulting product was extracted with a large amount of hot ethyl acetate. The extract was concentrated to about 5 ml, and the resulting precipitate was collected by filtration to obtain 229 mg of the desired compound.

1) Melting point: 184-187 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: ¹ H-nuclear magnetic resonance spectrum measured in deuterated dimethyl sulfoxide using TMS (tetramethylsilane) as an internal standard (270 MHz) is as follows. 2.20 (3H, s), 2.90 (1H, d, d, J = 8, 14 Hz), 3.00 (1
H, d, d, J = 6, 14 Hz), 4.05 (2H, d, d, J = 6, 8 Hz),
4.25 (2H, t, J = 5 Hz), 4.46 (2H, t, J = 5 Hz), 6.51
-6.58 (3H, m), 6.89 (2H, d, J = 8.5 Hz), 7.05 (2H,
t, J = 8 Hz), 7.21 (2H, t, J = 8.5 Hz), 7.36-7.51 (3H,
m), 7.68-7.77 (6H, m).

Production Example 11 3- [4- [2-[[1-
(4-Biphenylyl) ethylidene] aminooxy] eth
[Xy] phenyl] -2- (N-phenyl-N-ethyla
Ethyl mino) propionate (Exemplified Compound No. 49-4)
2-[[1- (4-biphenylyl) obtained in Reference Example 3.
Ethylidene] aminooxy] ethanol 230 mg,
3- (4-hydroxyphenyl)-obtained in Reference Example 6
Ethyl 2- (N-phenyl-N-ethylamino) propionate 300 mg, triphenylphosphine 236
The reaction and after-treatment were carried out according to Production Example 3 using the compound (1 mg) and diethyl azodicarboxylate (157 mg) to obtain 353 mg of the target compound in the form of a syrup.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.08 (3H, t, J = 7 Hz), 1.15 (3H, t, J =
7 Hz), 2.27 (3H, s), 3.05 (1H, d, d, J = 7.5, 14 H
z), 3.24-3.46 (3H, m), 4.09 (2H, q, J = 7 Hz), 4.26
(2H, t, J = 5 Hz), 4.39 (1H, t, J = 7.5 Hz), 4.53 (2
H, t, J = 5 Hz), 6.66-6.76 (3H, m), 6.86 (2H, d, J
= 8.5 Hz), 7.10 (2H, d, J = 8.5 Hz), 7.18-7.25 (2H,
m), 7.33-7.38 (1H, m), 7.45 (2H, d, J = 7.5 Hz), 7.
58-7.61 (4H, m), 7.72 (2H, d, J = 8.5 Hz). Production Example 12 3- [4- [2-[[1- (4-biphenyl)
Lyl) ethylidene] aminooxy] ethoxy] phenyl
2-]-(N-phenyl-N-ethylamino) propyl
Ononic acid / hydrochloride ( hydrochloride of Exemplified Compound No. 49-4) 3- [4- [2-[[1- (4-
Biphenylyl) ethylidene] aminooxy] ethoxy]
Phenyl] -2- (N-phenyl-N-ethylamino)
Using 353 mg of ethyl propionate and 2 ml of a 1N aqueous solution of sodium hydroxide, the reaction and post-treatment were carried out according to Production Example 4, and the obtained product was further treated with a 4N hydrogen chloride dioxane solution to give an amorphous powder. 280 mg of the compound hydrochloride were obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: TMS as internal standard in deuterated dimethyl sulfoxide
The ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured using (tetramethylsilane) is as follows. 0.94 (3H, t, J = 7 Hz), 2.21 (3H, s), 3.02 (1H, d,
d, J = 9, 14 Hz), 3.17 (1H, d, d, J = 6, 14 Hz), 3.20
-3.40 (2H, m), 4.23 (2H, t, J = 5 Hz), 4.45 (2H, t,
J = 5 Hz), 4.53 (1H, d, d, J = 6, 9 Hz), 6.61-6.72 (3
H, m), 6.86 (2H, d, J = 8.5 Hz), 7.12-7.17 (4H, m),
7.36-7.51 (3H, m), 7.69-7.78 (6H, m).

Production Example 133- [4- [2-[[1-
(4-Biphenylyl) ethylidene] aminooxy] eth
Ethyl [xy] phenyl] -2-pyrrolylpropionate
(Ethyl ester of Exemplified Compound No. 50-4) 2-[[1- (4-biphenylyl) obtained in Reference Example 4.
[Ethylidene] aminooxy] ethyl methanesulfone
333 mg, 3- (4-hydrogen) obtained in Reference Example 8.
Ethyl (xyphenyl) -2-pyrrolylpropionate 2
60 mg and 55% oily sodium hydride 50 mg
The reaction and after-treatment are carried out according to Production Example 1 using
440 mg of the target compound was obtained in the form of a gum.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 1.20 (3H, t, J = 7 Hz), 2.27 (3H, s), 3.19 (1H, d,
d, J = 8.5, 14 Hz), 3.34 (1H, d, d, J = 6.5, 14 Hz),
4.17 (2H, q, J = 7 Hz), 4.25 (2H, t, J = 5 Hz), 4.52
(1H, t, J = 5 Hz), 4.68 (1H, d, d, J = 6.5, 8.5 Hz),
6.13-6.15 (2H, m), 6.71-6.73 (2H, m), 6.82 (2H, d,
J = 8.5 Hz), 6.93 (2H, d, J = 8.5 Hz), 7.33-7.48 (3H,
m), 7.58-7.61 (4H, m), 7.72 (2H, d, J = 8.5 Hz).

Production Example 14 3- [4- [2-[[1-
(4-Biphenylyl) ethylidene] aminooxy] eth
Xy] phenyl] -2-pyrrolylpropionic acid (Exemplified Compound No. 50-4) 3- [4- [2-[[1- (4-
Biphenylyl) ethylidene] aminooxy] ethoxy]
Phenyl] -2-pyrrolylpropionate ethyl 167m
g and lithium hydroxide monohydrate (42 mg), the reaction and post-treatment were carried out according to Production Example 10.
135 mg of crystalline target compound were obtained.

1) Melting point: 163-165 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: ¹ H measured in deuterated chloroform and a small amount of deuterated dimethyl sulfoxide using TMS (tetramethylsilane) as an internal standard. -The nuclear magnetic resonance spectrum (270 MHz) is as follows. 2.26 (3H, s), 3.17 (1H, d, d, J = 9.5, 14 Hz), 3.38
(1H, d, d, J = 5.5, 14 Hz), 4.24 (2H, t, J = 5 Hz),
4.51 (2H, t, J = 5 Hz), 4.67 (1H, d, d, J = 5.5, 9.5
Hz), 6.09-6.11 (2H, m), 6.70-6.72 (2H, m), 6.80
(2H, d, J = 8.5 Hz), 6.92 (2H, d, J = 8.5 Hz), 7.33-7.
48 (3H, m), 7.56-7.62 (4H, m), 7.72 (2H, d, J = 8.5
Hz).

Production Example 15 2-ethylamino-3- [4
-[2-[[1- [4- (2-pyridyl) phenyl] d
Tylidene] aminooxy] ethoxy] phenyl] propy
Ethyl onoate / hydrochloride (ethyl ester / hydrochloride of Exemplified Compound No. 43-35) (a) 2-N- (t-butoxycarbonyl) ethyl
Mino-3- [4- [2-[[1- [4- (2-pyridi
Ru) phenyl] ethylidene] aminooxy] ethoxy]
Ethyl phenyl] propionate 256 mg of 2-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethanol obtained in Reference Example 1, 2-N- (t- When 337 mg of ethyl butoxycarbonyl) ethylamino-3- (4-hydroxyphenyl) propionate, 289 mg of triphenylphosphine and 556 mg of diisopropyl azodicarboxylate are reacted and worked up according to Production Example 3, a syrup-like product is obtained. 320 mg of the desired compound were obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 0.92 (3H, t, J = 7 Hz), 1.18-1.32 (3H, m), 1.45 (9
H, s), 2.29 (3H, s), 2.55-2.85 (1H, m), 3.00-3.40
(3H, m), 3.85-4.25 (3H, m), 4.28 (2H, t, J = 5 Hz),
4.55 (2H, t, J = 5 Hz), 6.88 (2H, d, J = 8.5 Hz), 7.0
5-7.14 (2H, brd, J = 8.5 Hz), 7.22-7.26 (1H, m), 7.7
5-7.82 (4H, m), 8.01 (2H, d, J = 8.5 Hz), 8.71 (1H,
d, J = 5 Hz).

(B) 2-ethylamino-3- [4-
[2-[[1- [4- (2-pyridyl) phenyl] ethyl]
[Ridene] aminooxy] ethoxy] phenyl] propio
Ethyl phosphate / hydrochloride 2-N- (t-butoxycarbonyl) ethylamino-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] ethyl propionate 3
12 mg was dissolved in 5 ml of a 4N hydrogen chloride / dioxane solution, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction solution was concentrated, and the obtained residue was triturated in ethyl ether and collected by filtration.
was gotten.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: TMS as internal standard in deuterated dimethyl sulfoxide
The ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured using (tetramethylsilane) is as follows. 1.10 (3H, t, J = 7 Hz), 1.24 (3H, t, J = 7 Hz), 2.25
(3H, s), 2.95-3.06 (2H, m), 3.39 (1H, q, J = 7 Hz),
4.08 (2H, q, J = 7 Hz), 4.18-4.22 (1H, m), 4.29 (2
H, t, J = 5 Hz), 4.50 (2H, t, J = 5 Hz), 6.95 (2H, d,
J = 8.5 Hz), 7.16 (2H, d, J = 8.5 Hz), 7.59-7.64 (1
H, m), 7.85 (2H, d, J = 8.5 Hz), 8.15 (2H, d, J = 8.5 H
z), 8.17-8.21 (2H, m), 8.77 (1H, d, J = 5 Hz).

Production Example 162-ethylamino-3- [4
-[2-[[1- [4- (2-pyridyl) phenyl] d
Tylidene] aminooxy] ethoxy] phenyl] propy
On-acid(Exemplified Compound No. 43-35) 2-Ethylamino-3- [4- obtained in Production Example 15
[2-[[1- [4- (2-pyridyl) phenyl] ethyl]
[Ridene] aminooxy] ethoxy] phenyl] propio
273 mg of ethyl phosphate and 1N aqueous sodium hydroxide
The reaction was carried out according to Production Example 2 using 2.4 ml of the solution.
The resulting reaction solution is adjusted to pH 4 with 1N hydrochloric acid.
Then, the target compound was precipitated as a precipitate. Filter this,
Eyes with a melting point of 220-222 ° C (decomposition) when washed with water
186 mg of the target compound were obtained. Production Example 172-methylthio-3- [4- [2-[[1
-[4- (2-pyridyl) phenyl] ethylidene] ami
Nooxy] ethoxy] phenyl] ethyl propionate
(Ethyl ester of Exemplified Compound No. 26-35) 4 ′-(2-pyridyl) acetophene obtained in Reference Example 2
Nonoxime O-2- (methanesulfonyloxy)
1.26 g of chill ether, obtained in Reference Example 11 (b)
3- (4-hydroxyphenyl) -2- (methylthio
E) 0.83 g of ethyl propionate and 55% oiliness
The same procedure as in Production Example 1 was carried out using 0.17 g of sodium hydride.
Syrup-like target after reaction and after-treatment
1.50 g of the compound were obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.22 (3H, t, J = 7 Hz), 2.16 (3H, s),
2.28 (3H, s), 2.90 (1H, d, d, J = 6.5, 14 Hz), 3.15
(1H, d, d, J = 9,14 Hz), 3.40 (1H, d, d, J = 6.5, 9 H
z), 4.13 (2H, d, q, J = 3, 7 Hz), 4.28 (2H, t, J = 5 H
z), 4.55 (2H, t, J = 5 Hz), 6.89 (2H, d, J = 8.5 H
z), 7.13 (2H, d, J = 8.5 Hz), 7.22-7.27 (1H, m), 7.
75-7.78 (4H, m), 8.01 (2H, d, J = 8.5 Hz), 8.71 (1H,
d, J = 4.5 Hz).

Production Example 18 2-Methylthio-3- [4-
[2-[[1- [4- (2-pyridyl) phenyl] ethyl]
[Ridene] aminooxy] ethoxy] phenyl] propio
Acid (Exemplified Compound No. 26-35) 2-Methylthio-3- [4- [2] obtained in Production Example 17
-[[2-[[1- [4- (2-pyridyl) phenyl]]
Ethylidene] aminooxy] ethoxy] phenyl] ethyl propionate 1.20 g and ethanol 20 m
1N aqueous solution of sodium hydroxide 5.05 ml
Was added and stirred at 50 ° C. for 30 minutes. After completion of the reaction, ethanol was distilled off from the reaction solution under reduced pressure.
5.05 ml of hydrochloric acid was added, and the precipitated product was extracted with ethyl acetate. The obtained extract was dried over anhydrous magnesium sulfate and then distilled off under reduced pressure. The obtained residual powder was washed with isopropyl ether to obtain 0.95 g of the desired compound.

1) Melting point 114-118 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) in deuterated chloroform as an internal standard
¹ H-nuclear magnetic resonance spectrum (27
0 MHz) is as follows.

2.22 (3H, s), 2.25 (3H, s), 2.91 (1
H, d, d, J = 5.5, 14 Hz), 3.18 (1H, d, d, J = 10,14 H
z), 3.44 (1H, d, d, J = 5.5, 10 Hz), 4.33 (2H, t, J =
5.5 Hz), 4.55 (2H, t, J = 5.5 Hz), 6.89 (2H, d, J = 8.
5 Hz), 7.15 (2H, d, J = 8.5 Hz), 7.26-7.32 (1H,
m), 7.63 (2H, d, J = 8.5 Hz), 7.71-7.84 (2H, m), 7.
87 (2H, d, J = 8.5 Hz), 8.70 (1H, d, J = 4.5 Hz).

Production Example 19 2- (3-Phenylpropionate)
) -3- [4- [2-[[1- [4- (2-pyridi
Ru) phenyl] ethylidene] aminooxy] ethoxy]
Phenyl] ethyl propionate (Exemplified Compound No. 66
Ethyl ester of -8) 4 '-(2-pyridyl) acetophenone oxime O-2- (methanesulfonyloxy) ethyl ether obtained in Reference Example 2.09 g, 2- (meth) sulfonyloxy obtained in Reference Example 12 (c) The reaction and after-treatment according to Production Example 1 using 1.00 g of ethyl (4-hydroxybenzyl) -5-phenylvalerate and 160 mg of 55% oily sodium hydride gave 1.54 g of a crystalline target compound. was gotten.

1) Melting point 53-55 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) as an internal standard in chloroform-d
¹ H-nuclear magnetic resonance spectrum (27
0 MHz) is as follows.

1.14 (3H, t, J = 7 Hz), 1.49-1.75 (4H,
m), 2.28 (3H, s), 2.56-2.71 (4H, m), 2.84 (1H, d,
d, J = 7.5, 12.5 Hz), 4.05 (2H, q, J = 7 Hz), 4.27 (2
H, t, J = 5 Hz), 4.55 (2H, t, J = 5 Hz), 6.86 (2H, d,
J = 8.5 Hz), 7.05 (2H, d, J = 8.5 Hz), 7.12-7.29 (6
H, m), 7.75-7.78 (4H, m), 8.01 (2H, d, J = 8.5 Hz),
8.70 (1H, d, J = 5 Hz).

Production Example 20 2- (3-phenylpropyl)
) -3- [4- [2-[[1- [4- (2-pyridi
Ru) phenyl] ethylidene] aminooxy] ethoxy]
Phenyl] propionic acid (Exemplified Compound No. 66-8) 2- (3-phenylpropyl)-obtained in Production Example 19
0.67 g of potassium hydroxide was added to a solution of 1.20 g of ethyl 3- [4- [2-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionate and 20 ml of ethanol. The mixture was stirred at 80 ° C. for 2 hours. After completion of the reaction, the reaction solution was concentrated, water, ice and ethyl acetate were added to the obtained residue, and the mixture was adjusted to pH 4 with 3N hydrochloric acid. Then the ethyl acetate layer was separated. The obtained extract was dried over anhydrous magnesium sulfate and then distilled off under reduced pressure to obtain 1.10 g of the target compound as a gum.

415 mg of the obtained target compound was dissolved in 10 ml of ethanol, and a 1N aqueous solution of sodium hydroxide was added.
0.80 ml was added, the mixture was concentrated, and the obtained solid was washed with ethyl ether to obtain 0.42 g of a sodium salt of the target compound as an amorphous solid.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: TMS as internal standard in deuterated dimethyl sulfoxide
The ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured using (tetramethylsilane) is as follows.

1.40-1.67 (5H, m), 2.24 (3H, s), 2.3
6-2.51 (4H, m), 2.83 (2H, d, d, J = 7, 13.5 Hz), 4.2
3 (2H, t, J = 4 Hz), 4.48 (2H, t, J = 4 Hz), 6.81 (2H,
 d, J = 8.5 Hz), 7.06-7.12 (5H, m), 7.17-7.23 (2H,
m), 7.35 (1H, d, d, J = 5, 6 Hz), 7.79 (2H, d, J = 8.5
 Hz), 7.87 (1H, d, t, J = 1.5, 8Hz), 7.97 (1H, d, J =
8 Hz), 8.12 (2H, d, J = 8.5 Hz), 8.67 (1H, d, J = 5 H
z). Production Example 212-phenoxy-3- [4- [2-[[1
-[4- (2-pyridyl) phenyl] ethylidene] ami
Nooxy] ethoxy] phenyl] ethyl propionate
(Ethyl ester of Exemplified Compound No. 68-2) 4 ′-(2-pyridyl) acetophen obtained in Reference Example 2
Nonoxime O-2- (methanesulfonyloxy)
1.18 g of chill ether, obtained in Reference Example 13 (c)
3- (4-hydroxyphenyl) -2-phenoxyp
1.28 g of ethyl propionate and 55% oily hydrogenation
Using 154 mg of sodium, the reaction was performed according to Production Example 1.
After the reaction and post-treatment, the syrupy target compound
1.28 g were obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.19 (3H, t, J = 7Hz), 2.26 (3H, s),
3.17-3.20 (2H, m), 4.17 (2H, q, J = 7Hz), 4.27 (2H, t,
J = 5Hz), 4.54 (2H, t, J = 5Hz), 4.74 (1H, d, d, J = 5.
5, 6.5Hz), 6.82-6.96 (5H, m), 7.21-7.26 (5H, m),
7.74-7.77 (4H, m), 8.01 (2H, d, J = 8.5Hz), 8.70
(1H, d, J = 5Hz).

Production Example 22 2-phenoxy-3- [4-
[2-[[1- [4- (2-pyridyl) phenyl] ethyl]
[Ridene] aminooxy] ethoxy] phenyl] propio
Acid (Exemplified Compound No. 68-2) 2-phenoxy-3- [4- [2] obtained in Production Example 20
Using 1.28 g of ethyl-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionate and 7.00 ml of 1N aqueous sodium hydroxide, the reaction was carried out according to Production Example 18. After work-up, the desired compound in crystalline powder 1.13
g was obtained.

1) Melting point: 145 ° -148 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) as an internal standard in deuterated chloroform
¹ H-nuclear magnetic resonance spectrum (27
0 MHz) is as follows.

2.25 (3H, s), 3.22 (2H, d, J = 6 Hz),
4.29 (2H, t, J = 4.5Hz), 4.54 (2H, t, J = 4.5Hz), 4.81
(1H, t, J = 6Hz), 6.86-6.97 (5H, m), 7.21-7.31 (5H,
m), 7.67-7.89 (6H, m), 8.72 (1H, d, J = 5Hz).

Production Example 23 2-butyl-3- [4- [2
-[[1- [4- (2-pyridyl) phenyl] ethylide
[Aminooxy] ethoxy] phenyl] propionic acid
Ethyl (ethyl ester of Exemplified Compound No. 67-8) 1.35 g of 4 '-(2-pyridyl) acetophenone oxime O-2- (methanesulfonyloxy) ethyl ether obtained in Reference Example 2, Reference Example 14 (c) Ethyl 2- (4-hydroxybenzyl) caproate obtained in
1.00 g and 55% oily sodium hydride 200
When the reaction and after-treatment were carried out using mg in accordance with Production Example 1, 0.94 g of the syrupy target compound was obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

0.87 (3H, t, J = 7 Hz), 1.16 (3H, t, J = 7
Hz), 1.20-1.40 (4H, m), 1.40-1.70 (2H, m), 2.28
(3H, s), 2.51-2.72 (2H, m), 2.86 (1H, d, d, J = 8.5,
13.5Hz), 4.06 (2H, q, J = 7Hz), 4.27 (2H, t, J = 5H
z), 4.54 (2H, t, J = 5Hz), 6.87 (2H, d, 8.5Hz), 7.0
7 (2H, d, J = 8.5Hz), 7.21-7.27 (1H, m), 7.71-7.80
(4H, m), 8.01 (2H, d, J = 8.5Hz), 8.71 (1H, d, J = 5H
z).

Production Example 24 2-butyl-3- [4- [2
-[[1- [4- (2-pyridyl) phenyl] ethylide
[ Aminooxy ] ethoxy] phenyl] propionic acid (Exemplified Compound No. 67-8) 2-butyl-3- [4- [2-] obtained in Reference Example 23
Using 0.94 g of ethyl [[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] benzyl] propionate and 3.86 ml of 1N aqueous sodium hydroxide, the reaction was carried out according to Production Example 18, followed by reaction. After the treatment, 0.69 g of a gum-like target product was obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

0.88 (3H, t, J = 8.5Hz), 1.23-1.37 (4H,
m), 1.43-1.73 (2H, m), 2.60-2.74 (2H, m), 2.90
(1H, d, d, J = 8.5, 13.5Hz), 4.30 (2H, t, J = 5Hz), 4.
55 (2H, t, J = 5Hz), 6.87 (2H, d, J = 8.5Hz), 7.10 (2
H, d, J = 8.5Hz), 7.24-7.28 (1H, m), 7.68-7.81 (4
H, m), 7.95 (2H, d, J = 8.5Hz), 8.70 (1H, d, J = 5Hz)
.

Production Example 25 2-butyl-3- [4- [2
-[[1- [4- (2-pyridyl) phenyl] ethylide
[Aminooxy] ethoxy] phenyl] propionic acid
-Sodium salt ( sodium salt of Exemplified Compound No. 67-8) 2-butyl-3- [4- [2-
When 0.69 g of [[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid is treated with 1.50 ml of 1N sodium hydroxide according to the method of Production Example 20, 0.65 g of a powdery sodium salt of the target compound was obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: TMS as internal standard in deuterated dimethyl sulfoxide
The ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured using (tetramethylsilane) is as follows.

0.79 (3H, t, J = 6.5Hz), 1.04-1.30 (5H,
m), 1.30-1.49 (1H, m), 2.09-2.25 (1H, m), 2.23
(3H, s), 2.39 (1H, d, d, J = 7.5, 13.5Hz), 2.78 (1H,
d, d, J = 7.5, 13.5Hz), 4.23 (2H, t, J = 4.5Hz), 4.47
(2H, t, J = 4.5Hz), 6.83 (2H, d, J = 8.5Hz), 7.07
(2H, d, J = 8.5Hz), 7.37 (1H, d, d, J = 6, 7.5Hz), 7.8
0 (2H, d, J = 8.5Hz), 7.90 (1H, d, t, J = 2, 8.5Hz),
8.00 (1H, d, J = 8Hz), 8.13 (2H, d, J = 8.5Hz), 8.69
(1H, d, J = 4.5Hz).

Reference Example 1 2-[[1- [4- (2-pyridyl)
Jill) phenyl] ethylidene] aminooxy] ethanol
Le (a) 4 '- in (2-pyridyl) acetophenone 4- (2-pyridyl) solution of benzimidazole nitrile 3.10g and dichloromethane 120 ml, in a nitrogen atmosphere,
After 21 ml of a 3M methylmagnesium bromide-diethyl ether solution was added dropwise under ice cooling, the reaction solution was stirred at room temperature for 20 hours. After completion of the reaction, an aqueous ammonium chloride solution and ethyl acetate were added to the reaction solution, and the mixture was stirred. The ethyl acetate layer was separated from the reaction solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography (ethyl acetate: hexane =
1: 2) to give a crystalline crude target compound.
This was further washed with diisopropyl ether-hexane to obtain 1.56 g of the target compound.

1) Melting point: 116-118 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) in deuterated chloroform as an internal standard
¹ H-nuclear magnetic resonance spectrum (27)
0Mz) is as follows. 2.66 (3H, s), 7.30 (1H, d, d, J = 4.5, 9 Hz), 7.79
-7.81 (2H, m), 8.05-8.13 (4H, m), 8.74 (1H, d, J =
4.5 Hz).

(B) 4 '-(2-pyridyl) acetophen
To a sodium methoxide-methanol solution prepared from a solution of 14.1 g of non-oxime sodium and 300 ml of methanol, 46.0 g of hydroxylamine hydrochloride was added.
Stirred at C for 30 minutes. Reference Example 1 (a)
4 '-(2-pyridyl) acetophenone 2 obtained in
3.0 g was added, and the mixture was stirred at 50 ° C. for 3 hours. After completion of the reaction, the reaction solution was concentrated, and 0.3 l of ethyl acetate and 0.3 l of water were added to the residue, followed by stirring, and 10.98 g of the precipitated target compound was collected by filtration. The ethyl acetate layer in the filtrate was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystalline residue was washed with diisopropyl ether to obtain 12.56 g of the target compound.

1) Melting point 177-178 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) in deuterated chloroform as an internal standard
¹ H-nuclear magnetic resonance spectrum (27
0Mz) is as follows. 2.20 (3H, s), 7.35 (1H, d, d, J = 4, 7.5 Hz), 7.78
(2H, d, J = 8.5 Hz), 7.89 (1H, d, d, J = 7.5, 8 Hz),
8.00 (1H, d, J = 8 Hz), 8.12 (2H, d, J = 8.5 Hz), 8.68
(1H, d, J = 4 Hz).

(C) 4 '-(2-pyridyl) acetophen
Non-oxime O-2-[(tetrahydropyran-2
-Yl) oxy] ethyl ether 2- (2-bromoethoxy) tetrahydropyran
20 g, 1.30 g of 4 ′-(2-pyridyl) acetophenone oxime obtained in Reference Example 1 (b) and N,
6.00 g of potassium carbonate was added to a solution of 27 ml of N-dimethylacetamide, and the mixture was stirred at 80 ° C for 16 hours. After completion of the reaction, the reaction solution was dissolved in ethyl acetate and water, the ethyl acetate layer was separated, and the extract was dried over anhydrous magnesium sulfate. After the ethyl acetate was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography (hexane: ethyl acetate =
Purification by 3: 1) gave 2.01 g of the desired compound in the form of a syrup.

(D) 2-[[1- [4- (2-pyridyl)
L ) phenyl] ethylidene] aminooxy] ethanol 2.01 g of 4 '-(2-pyridyl) acetophenone oxime O-2-[(tetrahydropyran-2-yl) oxy] ethyl ether obtained in Reference Example 1 (c) and 1.30 g of p-toluenesulfonic acid monohydrate was added to a solution of 30 ml of methanol, and the mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate and aqueous sodium bicarbonate, neutralized with sodium bicarbonate powder, and the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The extract was concentrated under reduced pressure to obtain a crystalline crude target compound. This was washed with diisopropyl ether-hexane to obtain 1.35 g of the target compound.

1) Melting point 74-76 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) as an internal standard in deuterated chloroform
¹ H-nuclear magnetic resonance spectrum (27
0Mz) is as follows. 2.31 (3H, s), 2.57 (1H, t, J = 6Hz), 3.95-3.99 (2
H, m), 4.34-4.36 (2H, m), 7.24-7.27 (1H, m), 7.74
-7.77 (4H, m), 8.02 (2H, d, J = 8.5 Hz), 8.71 (1H,
d, d, J = 1.5, 5 Hz).

Reference Example 2 4'-2- (2-pyridyl) a
Cetophenone oxime O-2- (methanesulfonyl
Xy) ethyl ether 1.00 g of 2-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethanol obtained in Reference Example 1 and methanesulfonyl chloride 493
After 0.82 ml of triethylamine was added dropwise to a solution of 10 mg of dichloromethane containing mg, the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the reaction solution was concentrated, and the residue was dissolved in ethyl acetate and water. Then, the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. Concentration of the ethyl acetate layer provided a crystalline residue. This was washed with isopropyl ether and hexane to yield 1.26 g of the desired compound.
was gotten.

1) Melting point 99-101 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) as an internal standard in chloroform-d
¹ H-nuclear magnetic resonance spectrum (27
0Mz) is as follows. 2.30 (3H, s), 3.04 (3H, s), 4.46-4.49 (2H, m),
4.55-4.58 (2H, m), 7.23-7.28 (1H, m), 7.74-7.78 (4
H, m), 8.02 (2H, d, J = 8.5 Hz), 8.71 (1H, d, J = 5 H
z).

Reference Example 3 2-[[1- (4-biphenyli)
L) ethylidene] aminooxy] ethanol (a) 4-acetylbiphenyl oxime O-2-
[(Tetrahydropyran-2-yl) oxy] ethyl
-Tel 2- (2-bromoethoxy) tetrahydropyran 1
5.8 g, 4-acetylbiphenyl oxime 6.4
0 g and potassium carbonate 20.9 g, Reference Example 1
The reaction and after-treatment according to (c) gave 10.2 g of the target compound in the form of a syrup.

(B) 2- [1- (4-biphenylyl) d
[Tylideneaminooxy] ethanol 4-acetylbiphenyl oxime O-2-[(tetrahydropyran-2-yl) obtained in Reference Example 3 (a)
Reference Example 1 using 10.2 g of [oxy] ethyl ether
The reaction and after-treatment according to (d) gave 6.53 g of the target compound.

1) Melting point 128-130 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) in deuterated chloroform as an internal standard
¹ H-nuclear magnetic resonance spectrum (27
0Mz) is as follows. 2.30 (3H, s), 2.58 (1H, br.s), 3.95-3.99 (2H,
m), 4.32-4.36 (2H, m), 7.36-7.48 (3H, m), 7.59-7.
62 (4H, m), 7.71 (2H, d, J = 8.5 Hz).

Reference Example 4 2-[[1- (4-biphenyli)
Le) ethylidene] aminooxy] ethyl methanesulfo
Sulfonate obtained in Reference Example 3 2 - [[1- (4-biphenylyl)
Using 3.20 g of [ethylideneaminooxy] ethanol, 1.49 g of methanesulfonyl chloride and 1.80 g of triethylamine, the reaction and post-treatment were carried out according to Reference Example 2, to obtain 3.80 g of the target compound.

1) Melting point: 103-104 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) in deuterated chloroform as an internal standard
¹ H-nuclear magnetic resonance spectrum (27
0Mz) is as follows.

2.30 (3H, s), 3.04 (3H, s), 4.45-4.4
8 (2H, m), 4.54-4.58 (2H, m), 7.34-7.48 (3H, m),
7.61 (4H, d, J = 8.5 Hz), 7.73 (2H, d, J = 8.5 Hz).

Reference Example 5 3- (4-hydroxyphenyl)
Ethyl) -2- (phenylamino) propionate (a) 3- (4-benzyloxyphenyl) -2- (f
After stirring a mixture of 4.00 g of ethyl 3- (4-benzyloxyphenyl) -2-methanesulfonyloxypropionate and 5 ml of aniline at 110 ° C. for 24 hours, the reaction product was subjected to silica gel column chromatography (ethyl acetate:
Purification by hexane (1: 4) gave 3.94 g of the target compound in the form of a syrup.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 Mz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 1.17 (3H, t, J = 7 Hz), 3.00-3.14 (2H, m), 4.12 (2H,
d, q, J = 1.5, 7 Hz), 4.30 (1H, t, J = 6 Hz), 5.04
(2H, s), 6.60 (2H, d, J = 8.5 Hz), 6.73 (1H, t, J = 7.
5 Hz), 6.89 (2H, d, J = 8.5 Hz), 7.09 (2H, d, J = 8.5
Hz), 7.16 (2H, d, J = 8.5 Hz), 7.31-7.44 (5H, m).

(B) 3- (4-hydroxyphenyl)-
Ethyl 2- (phenylamino) propionate A mixed solution of 3.94 g of ethyl 3- (4-benzyloxyphenyl ) -2- (phenylamino) propionate obtained in Reference Example 5 (a), 40 ml of ethanol and 20 ml of tetrahydrofuran Then, 0.80 g of 5% palladium-carbon was added, and the mixture was stirred at 50 ° C. for 6 hours under a normal hydrogen pressure. After the catalyst was filtered off from the reaction mixture, the solvent was distilled off, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 2) to give 2.95 g of the desired compound in the form of a syrup. Was done.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 Mz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 1.19 (3H, t, J = 7 Hz), 3.00-3.13 (2H, m), 4.13 (2
H, d, q, J = 1, 7 Hz), 4.30 (1H, brt, J = 6 Hz), 4.88
(1H, brs), 6.60 (2H, d, J = 8 Hz), 6.71-6.76 (3H,
m), 7.03 (2H, d, J = 8 Hz), 7.14-7.20 (2H, m).

Reference Example 6 3- (4-hydroxyphenyl)
) -2- (N-phenyl-N-ethylamino) propyl
Ethyl onoate (a) 3- (4-benzyloxyphenyl) -2- (N
Ethyl-phenyl-N-ethylamino) propionate Using 4.50 g of ethyl 3- (4-benzyloxyphenyl) -2-methanesulfonyloxypropionate and 5.6 ml of N-ethylaniline, The reaction and post-treatment were carried out according to the procedure to obtain 6.30 g of a mixture of the target compound and N-ethylaniline in the form of syrup.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 Mz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 1.07 (3H, t, 3H, J = 7 Hz), 1.14 (3H, t, J = 7 Hz),
3.01-3.45 (4H, m), 4.09 (2H, q, J = 7 Hz), 4.39
(1H, t, J = 7.5 Hz), 5.02 (2H, s), 6.66-6.75 (3H,
m), 6.87 (2H, d, J = 8 Hz), 7.10 (2H, d, J = 8.5 H
z), 7.15-7.25 (2H, m), 7.31-7.44 (5H, m).

(B) 3- (4-hydroxyphenyl)-
2- (N-phenyl-N-ethylamino) propionic acid
Ethyl Reference Example 6 (a) obtained in 3- (4-benzyloxyphenyl)-2-(N- phenyl--N- ethylamino) mixtures of propionic acid ethyl and N- ethylaniline 6.
The reaction and after-treatment were carried out according to Reference Example 5 (b) using 30 g to obtain 2.37 g of the target compound in the form of a syrup.

1) 1H-nuclear magnetic resonance spectrum: δ p
pm: 1H-nuclear magnetic resonance spectrum (270 Mz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 1.07 (3H, t, J = 7 Hz), 1.15 (3H, t, J = 7 Hz), 3.05
(1H, d, d, J = 8, 14 Hz), 3.26 (1H, d, d, J = 7.5, 14
Hz), 3.30-3.46 (2H, m), 4.10 (2H, q, J = 7 Hz), 4.3
8 (1H, t, J = 8 Hz), 4.75 (1H, br.s), 6.67-6.79 (5H,
m), 7.05 (2H, d, J = 8.5 Hz), 7.18-7.26 (2H, m).

Reference Example 7 3- (4-hydroxyphenyl)
Methyl) -2- (phenylthio) propionate (a) 3- (4-methoxymethoxyphenyl) -2-
Methyl (phenylthio) propionate 745 mg of methyl 3- (4-methoxymethoxyphenyl) -2-methanesulfonyloxypropionate, 310 mg of thiophenol and 390 mg of potassium carbonate
After stirring a solution of 15 ml of N, N-dimethylformamide containing for 0.5 hour at 50 ° C., ethyl acetate and water were added,
Then, the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 4) to give 698 mg of the desired compound in the form of a syrup.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 Mz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 3.00 (1H, d, d, J = 6.5, 14 Hz), 3.15 (1H, d, d, J =
9, 14 Hz), 3.47 (3H, s), 3.59 (3H, s), 3.86 (1H,
d, d, J = 6.5, 9 Hz), 5.15 (2H, s), 6.94 (2H, d, J =
8.5 Hz), 7.10 (2H, d, J = 8.5 Hz), 7.29-7.33 (3H,
m), 7.40-7.45 (2H, m).

(B) 3- (4-hydroxyphenyl)-
Methyl 2- (phenylthio) propionate A solution of 689 mg of methyl 3- (4-methoxymethoxyphenyl) -2- (phenylthio) propionate obtained in Reference Example 7 (a) in 3 ml of 4N hydrogen chloride / dioxane was added at room temperature to a solution of 0.1 ml. After stirring for 5 hours, the mixture was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate and water, the ethyl acetate layer was separated, dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain 595 mg of the target compound in the form of a syrup.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 Mz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 2.99 (1H, d, d, J = 6.5, 14 Hz), 3.12 (1H, d, d, J =
9, 14 Hz), 3.58 (3H, s), 3.86 (1H, d, d, J = 6.5, 9
Hz), 4.97 (1H, br s), 6.72 (2H, d, J = 8.5 Hz), 7.0
5 (2H, d, J = 8.5 Hz), 7.23-7.34 (3H, m), 7.40-7.45
(2H, m).

Reference Example 8 3- (4-hydroxyphenyl)
E) ethyl 2-pyrrolylpropionate (a) 3- (4-benzyloxyphenyl) -2-pyrro
Ethyl rilpropionate 3.30 g of ethyl 3- (4-benzyloxyphenyl) -2-aminopropionate 80 ml of dichloromethane
Add 1,4-dichloro-1,4-dimethoxybutane to the solution
3.30 g was added, and Amberlyst A-21 20
g was added and stirred at room temperature for 18 hours. After completion of the reaction, the reaction solution was filtered. The filtrate is concentrated, and the obtained residue is subjected to silica gel column chromatography (ethyl acetate: hexane =
1: 5) to give 1.00 g of the desired compound in the form of a syrup. 1) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) in deuterated chloroform as an internal standard
¹ H-nuclear magnetic resonance spectrum (27
0Mz) is as follows. 1.19 (3H, t, J = 7 Hz), 3.19 (1H, d, d, J = 8.5, 14 H
z), 3.34 (1H, d, d, J = 7, 14 Hz), 4.14 (2H, q, J = 7
Hz), 4.68 (1H, d, d, J = 7, 8.5 Hz), 5.01 (2H, s),
6.15 (2H, t, J = 2 Hz), 6.73 (2H, t, J = 2 Hz), 6.84
(2H, d, J = 8.5 Hz), 6.94 (2H, d, J = 8.5 Hz), 7.28-7.
43 (5H, m).

(B) 3- (4-hydroxyphenyl)-
2- [N- (phenyl) ethylamino] propionic acid
Obtained in chill Reference Example 8 (a) 3- (4- benzyloxyphenyl) -2-pyrrolyl propionate 1.00
g and 5% palladium-carbon 0.12 g, and the reaction and post-treatment were carried out according to Reference Example 5 (b) to obtain 0.71 g of the syrupy target compound.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 Mz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 1.20 (3H, t, J = 7 Hz), 3.18 (1H, d, d, J = 8.5, 14 H
z), 3.33 (1H, d, d, J = 7, 14 Hz), 4.15 (2H, q, J = 7
Hz), 4.67 (1H, d, d, J = 7, 8.5 Hz), 4.80 (1H, s),
6.14 (2H, t, J = 2 Hz), 6.71 (2H, d, J = 8.5 Hz), 6.72
(2H, d, J = 2 Hz), 6.88 (2H, d, J = 8.5 Hz).

Reference Example 9 2- (N, N-diethylamido)
D) -3- (4-Hydroxyphenyl) propionic acid
To a solution of 491 mg of chill DL-tyrosine ethyl ester hydrochloride in 5 ml of methanol were added 0.3 ml of acetic acid and 0.5 ml of acetaldehyde, and 126 mg of sodium cyanoborohydride was added under ice-cooling, followed by stirring at room temperature for 2 hours. After completion of the reaction, the reaction solution was concentrated, and the obtained residue was dissolved in ethyl acetate and water, and then the ethyl acetate layer was separated. The extract was washed with aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (methanol: dichloromethane =
1:20) to give 420 mg of the desired compound in the form of a syrup.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 Mz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows. 1.02 (6H, t, J = 7 Hz), 1.16 (3H, t, J = 7 Hz), 2.53
(2H, sextet, J = 7 Hz), 2.79 (2H, sextet, J = 7 Hz),
2.81 (1H, d, d, J = 6, 13.5 Hz), 2.99 (1H, d, d, J =
9, 13.5 Hz), 3.55 (1H, d, d, J = 6, 9 Hz), 4.02-4.11
(2H, m), 6.72 (2H, d, J = 8.5 Hz), 7.02 (2H, d, J =
8.5 Hz).

Reference Example 10 2-N- (t-butoxycal
Bonyl) ethylamino-3- (4-hydroxyphenyl)
E) Ethyl propionate (a) 2-ethylamino-3- (4-hydroxyphenyl )
E ) Ethyl propionate DL-tyrosine ethyl ester hydrochloride (983 mg), acetaldehyde (0.26 ml) and sodium cyanoborohydride (100 mg) were reacted and worked up according to Reference Example 9 to obtain a syrupy target compound.
15 mg were obtained. It crystallized on standing.

1) Melting point 87-89 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) in deuterated chloroform as an internal standard
¹ H-nuclear magnetic resonance spectrum (27
0 MHz) is as follows.

1.08 (3H, t, J = 7 Hz), 1.18 (3H, t, J =
7 Hz), 2.48-2.72 (2H, m), 2.82-2.96 (2H, m), 3.50
(1H, t, J = 7 Hz), 4.11 (2H, q, J = 7 Hz), 6.68 (2H,
d, J = 8.5 Hz), 7.01 (2H, d, J = 8.5 Hz).

(B) 2-N- (t-botoxycarboni
L) Ethylamino-3- (4-hydroxyphenyl) p
Ethyl ropionate 2-ethylamino-3- obtained in Reference Example 10 (a)
Ethyl (4-hydroxyphenyl) propionate 56
To a solution of 9 mg, 785 mg of di-t-butyl dicarbonate and 10 ml of dichloromethane was added dropwise 1 ml of triethylamine under ice-cooling, followed by stirring at room temperature for 4 hours. After completion of the reaction, the reaction solution was concentrated, and the obtained residue was dissolved in ethyl acetate and water, and then the ethyl acetate layer was separated. The obtained extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate-hexane = 1: 1).
By subjecting it to 2), 663 mg of the syrupy target compound was obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

0.90 (3H, brt, J = 7 Hz), 1.21-1.31 (3
H, m), 1.45 (9H, s), 3.15-3.37 (1H, m), 3.08 (1H,
d, d, J = 10, 14 Hz), 3.15-3.37 (1H, m), 3.24 (1H,
d, d, J = 5, 14 Hz), 3.85-4.30 (3H, m), 6.76 (2H, br
d, J = 8.5 Hz), 7.00-7.11 (2H, m).

Reference Example 11 3- (4-hydroxyphenyl)
Ethyl) -2- (methylthio) propionate (a) 3- (4-methoxymethoxyphenyl) -2-me
Ethyl tylthiopropionate A solution of 17.2 g of ethyl 3- (4-methoxymethoxyphenyl) -2-methanesulfonyloxypropionate, 4.20 g of sodium thiomethoxide and 300 ml of N, N-dimethylformamide at 50 ° C. 5
Stirred for hours. After completion of the reaction, ethyl acetate and water were added to the reaction solution, and then the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The obtained extract was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 4) to give a syrup of the desired compound 1.
1.37 g were obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
The ¹ H-nuclear magnetic resonance spectrum (270 Mz) measured in pm deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.22 (3H, t, J = 7 Hz), 2.17 (3H, s),
2.91 (1H, d, d, J = 6.5, 14 Hz), 3.15 (1H, d, d, J = 9,
14 Hz), 3.41 (1H, d, d, J = 6.5, 9 Hz), 3.47 (2H,
s), 4.09-4.23 (2H, m), 5.15 (3H, s), 6.96 (2H, d,
J = 8.5 Hz), 7.13 (2H, d, J = 8.5 Hz).

(B) 3- (4-hydroxyphenyl)-
Ethyl 2- (methylthio) propionate Ethyl 3- (4-methoxymethoxyphenyl) -2-methylthio) propionate obtained in Reference Example 11 (a)
When 2.01 g and 4N hydrogen chloride-dioxane 11 ml were used for the reaction and post-treatment according to Reference Example 7 (b), 1.70 g of the syrupy target compound was obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.22 (3H, t, J = 7.5 Hz), 2.17 (3H, s),
2.89 (1H, d, d, J = 6.5, 14 Hz), 3.13 (1H, d, d, J =
9, 14 Hz), 3.41 (1H, d, d, J = 6.5, 14 Hz), 4.09-4.2
0 (2H, m), 5.05 (1H, s), 6.74 (2H, d, J = 8.5 Hz),
7.07 (2H, d, J = 8.5 Hz).

Reference Example 12 2- (4-hydroxybenzyl)
L) -5-phenylvaleric acid ethyl (a) 2- (4-benzyloxybenzyl) -2- (3
1.-Phenylpropyl) malonate diethyl 2- (3-phenylpropyl) malonate
To a mixed solution of 78 g, toluene 20 ml and N, N-dimethylacetamide 10 ml was added 0.48 g of 55% oily sodium hydride, and the mixture was stirred at room temperature for 30 minutes. Then, 2.45 g of 4-benzyloxybenzyl chloride was added thereto, and the mixture was added at room temperature for 30 minutes and then at 60.degree.
Stirred at C for 30 minutes. After completion of the reaction, ethyl acetate and water were added to the reaction solution, and then the ethyl acetate layer was separated. The obtained extract was dried over anhydrous magnesium sulfate and concentrated.
The obtained residue was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 9) to give 3.91 g of the desired compound in the form of a syrup.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.21 (6H, s), 1.57-1.66 (2H, m), 1.7
6-1.85 (2H, m), 2.61 (2H, t, J = 6.5 Hz), 3.14 (2H,
s), 4.15 (4H, d, q, J = 1.5, 7Hz), 5.01 (2H, s), 6.
79 (2H, d, J = 8.5 Hz), 6.89 (2H, d, J = 8.5 Hz), 7.15
-7.44 (10H, m).

(B) 2- (4-benzyloxybenzyl )
E) -5-phenylethyl valerate 3.91 g of diethyl 2- (4-benzyloxybenzyl) -2- (3-phenylpropyl) malonate obtained in Reference Example 12 (a), 30 ml of 2-methoxyethanol
Potassium hydroxide 2.0 in a mixed solution of
0 g was added, and the mixture was stirred on a 130 ° C. oil bath for 1.5 hours.
After completion of the reaction, the reaction solution was concentrated, water and ethyl acetate were added to the concentrated solution, and then 6N hydrochloric acid was added to make the solution acidic. Next, the ethyl acetate layer was separated, washed with brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residual syrup was dissolved in 20 ml of xylene, stirred for 1 hour, and then concentrated.
The obtained syrupy 2- (4-benzyloxybenzyl) -5-phenylvaleric acid was dissolved in ethanol (40 ml), concentrated sulfuric acid (1 ml) was added, the mixture was stirred at 80 ° C. for 3 hours, and then left at room temperature for 16 hours. The reaction solution was concentrated, the residue was dissolved in ethyl acetate and water, and the ethyl acetate layer was separated. The obtained extract was dried over anhydrous magnesium sulfate and concentrated to obtain 3.32 g of a syrupy target compound.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.13 (3H, t, J = 7 Hz), 1.50-1.80 (4H,
m), 2.53-2.71 (4H, m), 2.82-2.90 (1H, m), 4.04 (2
H, q, J = 7 Hz), 5.04 (2H, s), 6.87 (2H, d, J = 8.5 H
z), 7.05 (2H, d, J = 8.5 Hz), 7.10-7.44 (10H, m).

(C) 2- (4-hydroxybenzyl)-
Ethyl 5-phenylvalerate Reference Example 5 was obtained using 3.32 g of ethyl 2- (4-benzyloxybenzyl) -5-phenylvalerate obtained in Reference Example 12 (b) and 0.4 g of 5% palladium-carbon.
When the reaction and post-treatment were carried out according to (b), 2.56 g of the target compound in the form of a syrup was obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.14 (3H, t, J = 7 Hz), 1.50-1.75 (4H,
m), 2.53-2.71 (4H, m), 2.78-2.87 (1H, m), 4.05 (2
H, q, J = 7 Hz), 6.70 (2H, d, J = 8.5 Hz), 6.98 (2H,
d, J = 8.5 Hz), 7.12-7.29 (5H, m).

Reference Example 13 3- (4-hydroxyphenyl)
E) 2-Phenoxypropionate ethyl (a) 2- (4-benzyloxybenzyl) -2-fe
Nokishimaron diethyl phenoxy Cimarron diethyl 2.81 g, 4-benzyloxybenzyl chloride 2.59g and 55%
Reference Example 12 using 530 mg of oily sodium hydride
When the reaction and post-treatment were carried out according to (a), 3.10 g of the syrupy target compound was obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.12 (6H, t, J = 7Hz), 3.57 (2H, s),
4.15 (4H, q, J = 7Hz), 5.02 (2H, s), 6.84-7.14 (6H,
m), 7.22-7.41 (8H, m).

(B) 3- (4-benzyloxyphenyi )
L) Ethyl 2-phenoxypropionate Diethyl 2- (4-benzyloxybenzyl) -2-phenoxymalonate obtained in Reference Example 13 (a) 3.1
When 0 g and 2.10 g of potassium hydroxide were used for the reaction and post-treatment according to Reference Example 12 (b), syrupy 3- (4-benzyloxyphenyl) -2-
Through phenoxypropionic acid, 2.10 g of the target compound in the form of a syrup were obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.18 (3H, t, J = 7Hz), 3.11-3.20 (2H,
m), 4.16 (2H, q, J = 7Hz), 4.74 (1H, d, d, J = 5.5, 6.
5Hz), 5.04 (2H, s), 6.84 (2H, d, J = 8Hz), 6.91 (2
H, d, J = 8.5Hz), 6.92-6.97 (1H, m), 7.05-7.09 (1
H, m), 7.22 (2H, d, J = 8.5 Hz), 7.20-7.43 (6H, m).

(C) 3- (4-hydroxyphenyl)-
1. Ethyl 2-phenoxypropionate Ethyl 3- (4-benzyloxyphenyl) -2-phenoxypropionate obtained in Reference Example 13 (b)
When 10 g and 5% palladium carbon (0.32 g) were used for the reaction and post-treatment according to Reference Example 5 (b), 1.01 g of the syrupy target compound was obtained.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

1.19 (3H, t, J = 7Hz), 3.10-3.24 (2H,
m), 4.17 (2H, q, J = 7Hz), 4.74 (1H, d, d, J = 6, 7H
z), 5.00 (1H, s), 6.74 (2H, d, J = 8.5Hz), 6.84 (2
H, d, J = 8Hz), 6.95 (1H, t, J = 7.5Hz), 7.16 (2H,
d, J = 8.5Hz), 7.21-7.26 (2H, m).

Reference Example 14 2- (4-hydroxybenzyl)
L) Ethyl caproate (a) 2- (4-benzyloxybenzyl) -2-butyi
Rumaron diethyl butyl malonate 2.16 g, using 4-benzyloxybenzyl chloride 2.44g and 55% oily sodium hydride 480 mg, Reference Example 12
When the reaction and post-treatment were carried out according to (a), 3.67 g of a crystalline target compound was obtained.

1) Melting point 73 ° C. 2) ¹ H-nuclear magnetic resonance spectrum: δ ppm: TMS (tetramethylsilane) as an internal standard in deuterated chloroform
¹ H-nuclear magnetic resonance spectrum (27
0 MHz) is as follows.

0.91 (3H, t, J = 7Hz), 1.24 (6H, t, J = 7
Hz), 1.20-1.38 (4H, m), 1.74-1.80 (2H, m), 3.18
(2H, s), 4.11-4.23 (4H, m), 5.02 (2H, s), 6.86 (2
(H, d, J = 8.5Hz), 6.99 (2H, d, J = 8.5Hz), 7.31-7.44
(5H, m).

(B) 2- (4-benzyloxybenzyl )
R) Ethyl caproate 3.60 g of diethyl 2- (4-benzyloxybenzyl) -2-butylmalonate obtained in Reference Example 14 (a)
Reference Example 1 using 2.00 g of potassium hydroxide and potassium hydroxide
The reaction and work-up according to 2 (b) gave, via crystalline 2- (4-benzyloxybenzyl) caproic acid, 2.71 g of the syrupy target compound.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

0.87 (3H, t, J = 7Hz), 1.14 (3H, t, J = 7
Hz), 1.20-1.70 (6H, m), 2.51-2.72 (2H, m), 2.85
(1H, d, d, J = 8.5, 13.5Hz), 4.05 (2H, q, J = 7Hz), 5.
03 (2H, s), 6.88 (2H, d, J = 8.5Hz), 7.07 (2H, d, J =
8.5Hz), 7.31-7.45 (5H, m).

(C) 2- (4-hydroxybenzyl) ca
With prong obtained in ethyl Reference Example 14 (b) 2- (4- benzyloxybenzyl) caproate ethyl 2.71g and 5% palladium on carbon 0.40 g, the reaction according to Reference Example 5 (b) and Post-treatment gave 1.90 g of the desired compound in the form of a syrup.

1) ¹ H-nuclear magnetic resonance spectrum: δ p
pm: ¹ H-nuclear magnetic resonance spectrum (270 MHz) measured in deuterated chloroform using TMS (tetramethylsilane) as an internal standard is as follows.

0.87 (3H, t, J = 7Hz), 1.16 (3H, t, J = 7
Hz), 1.20-1.35 (4H, m), 1.40-1.70 (2H, m), 2.53-
2.72 (2H, m), 2.84 (1H, d, d, J = 8.5, 13.5Hz), 4.06
(2H, q, J = 7Hz), 4.93 (1H, s), 6.72 (2H, d, J = 8.5H
z), 7.02 (2H, d, J = 8.5Hz).

[Examples] Hypoglycemic action (method 1 ) Male KK mice weighing 40 g or more and exhibiting hyperglycemic conditions
1 mg / kg of each compound was added to polyethylene glycol 40
0: 0.5% W / V carboxymethylcellulose physiological saline was mixed with a 1: 1 solvent and orally administered, and left for 18 hours under satiety conditions. Next, blood was collected from the tail vein under anesthesia, and the blood glucose level was measured using a glucose analyzer (GL-101 (trade name), manufactured by Mitsubishi Chemical Corporation).

The blood glucose lowering rate was determined by the following equation. Hypoglycemic rate (%) = [(solvent-administered group blood glucose level−compound-administered group blood glucose level) / solvent-administered group blood glucose level] × 100 The results are shown in Table 69.

[0430]

[Table 69] ──────────────────────────────────── Test compound Hypoglycemic rate (%) ──化合物 Compound of Production Example 2 21.9 Compound of Production Example 4 * 20. 2 Compound of Production Example 10 24.1 Compound of Production Example 16 26.9 ─.

* Shows the blood glucose lowering rate 3 hours after administration of the test compound. Table 69 shows that the compounds of the present invention exhibited excellent hypoglycemic action.

Hypoglycemic Action (Method 2 ) Male KK mice weighing 40 g or more and showing a hyperglycemic state
Each compound was mixed with powder feed F-2 (Funabashi Farm) at a ratio of 0.01% (about 10 mg / kg / day) and administered for 3 days. Separately, mice that received only powdered feed were used as a control group. Subsequently, blood was collected from the tail vein under anesthesia, and the blood glucose level in the plasma obtained by centrifugation was measured using a glucoloader F (A & T).
Manufactured by the company).

The blood glucose lowering rate was determined by the following equation. Hypoglycemic rate (%) = [(control group blood glucose level−compound administration group blood glucose level) / control group blood glucose level] × 100 The results obtained are shown in Table 70.

[0434]

[Table 70] ──────────────────────────────────── Test compound Hypoglycemic rate (%) ──化合物 Compound of Production Example 18 20.4 Compound of Production Example 20 47.0 ──────────────────────────────────.

As can be seen from Table 70, the compounds of the present invention exhibited an excellent hypoglycemic effect.

[Formulation Examples] (1) Capsule Preparation Example 2 Compound 10 mg Lactose 110 mg Corn starch 58 mg Magnesium stearate 2 mg 180 mg The powder of each of the above-mentioned components was mixed well, and a 60 mesh mesh was prepared. Pass through a sieve (mesh standard is based on Tyler standard). 180 mg of the obtained powder is weighed and filled into a gelatin capsule (No. 3) to prepare a capsule.

[0437] Mix well the powder of each component shown above,
Compress to tablets of mg weight. If necessary, these tablets may be coated with sugar or a film.

(3) Granule Preparation Example 2 10 mg Lactose 839 mg Corn Starch 150 mg Hydroxypropylcellulose 1 mg 1000 mg Mix well the powders of the above components, wet with pure water, basket Granulate with a granulator and dry to obtain granules.

[0439]

EFFECT OF THE INVENTION The phenylalkylcarboxylic acid derivative of the present invention, its pharmacologically acceptable salt or its pharmacologically acceptable ester is useful for the treatment of diabetes, hyperlipidemia, obesity, glucose intolerance, insulin resistance Glucose intolerance, hypertension, diabetic complications, arteriosclerosis, gestational diabetes, polycystic ovary syndrome, cardiovascular disease, atherosclerosis, cell damage caused by ischemic heart disease, osteoarthritis, rheumatism It is useful as a prophylactic and / or therapeutic agent for osteoarthritis allergic disease, asthma disease, cancer disease, autoimmune disease, pancreatitis, osteoporosis, cataract and the like.

────────────────────────────────────────────────── ─── front page continued (51) Int.Cl. ⁶ identifications FI A61K 31/00 606 A61K 31/00 606N 609 609J 609F 609 611 611C 615 615 619 619E 619A 627 627F 629 629 629A 635 635 637 637A 637E 643 643D 31/19 602 31/19 602 31/195 31/195 31/34 601 31/34 601 31/36 31/36 31/38 601 31/38 601 31/40 31/40 607 607 31/415 606 31 / 415 606 613 613 31/42 31/42 31/425 601 31/425 601 31/44 31/44 601 601 603 603 605 605 31/445 601 31/445 601 31/47 31/47 31/495 31 / 495 31/50 31/50 31/505 31/505 31/535 605 31/535 605 31/695 31 / 695 C07D 207/335 C07D 207/335 209/14 209/14 209/30 209/30 213/64 213/64 213/70 213/70 213/71 213/71 215/14 215/14 217/14 217 / 14 231/12 231/12 A 233/61 102 233/61 102 233/64 102 233/64 102 105 105 105 235/16 235/16 237/08 237/08 239/26 239/26 239/34 239 / 34 239/38 239/38 241/12 241/12 261/08 261/08 263/32 263/32 263/54 263/54 307/52 307/52 317/58 317/58 401/12 233 401/12 233 403/12 207 403/12 207 // C07C 251/24 C07C 251/24 C07D 277/28 C07D 277/28 277/64 277/64 295/12 295/12 Z 333/22 333/22 (72) Invention Person Toshihiko Fujiwara 1-58, Hiromachi, Shinagawa-ku, Tokyo Within Sankyo Co., Ltd.

Claims (66)

[Claims] 1. A compound of the general formula [Wherein, R ¹ represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, and R ² represents a linear or branched alkyl group having 2 to 6 carbon atoms. R ³ represents (i) a hydrogen atom, (ii) a C 1 to C 6 alkylene group.
A linear or branched alkyl group having
(Iii) a linear or branched alkoxy group having 1 to 4 carbon atoms, (iv) 1 to 4 carbon atoms
Linear or branched alkylthio groups having
(Vi) a halogen atom, (vi) a nitro group, (vi)
i) linear or branched dialkylamino groups having the same or different alkyls each having 1 to 4 carbon atoms; (viii) 1 to 3 substituted α groups to be described later
Or an aryl group having 6 to 10 carbon atoms which may have (ix) 1 to 3 carbon atoms which may have 1 to 3 substituents α described below in the aryl moiety.
Z represents a single bond or a linear or branched alkylene group having 1 to 6 carbon atoms; W represents (i) a straight-chain or alkylene group having 1 to 6 carbon atoms; A chain or branched alkyl group, (ii) a hydroxy group,
(Iii) a linear or branched alkoxy group having 1 to 4 carbon atoms, (iv) 1 to 4 carbon atoms
Linear or branched alkylthio groups having
(V) an amino group, (vi) a linear or branched monoalkylamino group having 1 to 4 carbon atoms,
(Vii) straight-chain or branched dialkylamino groups having the same or different alkyls each having 1 to 4 carbon atoms, (viii) straight-chain or branched dialkylamino groups having 1 to 4 carbon atoms An N-alkyl-N-arylamino group having an aryl having 6 to 10 carbon atoms optionally having 1 to 3 substituents α in the alkyl and aryl portions of (ix) 1 to 3 6 to 1 carbon atoms which may have a substituent α described below.
(X) an aryloxy group having 1 to 3 carbon atoms and 6 to 10 carbon atoms which may have a substituent α described later,
An arylthio group having 1 to 3 carbon atoms and 6 to 10 carbon atoms which may have a substituent α described later, and (xii) an aryl moiety having 1 to 3 substituents α described later. (Xiii) an aralkyl group having 1 to 3 carbon atoms and optionally having 7 to 12 carbon atoms which may have a substituent α described later, which has 6 to 10 carbon atoms, (Xiv) an aralkyloxy group having 7 to 12 carbon atoms which may have 1 to 3 substituents α described later in the aryl moiety, and (xv) 1 to 3 substituents described later in the aryl moiety. an aralkylthio group having 7 to 12 carbon atoms optionally having α; (xvi) an aryl moiety having 7 to 12 carbon atoms optionally having 1 to 3 substituents α described below. Aralkylamino group having, (xvi
i) a 1-pyrrolyl group, (xviii) a 1-pyrrolidinyl group, (xix) a 1-imidazolyl group, (xx) a piperidino group or (xxi) a morpholino group, and X represents 1 to 3 substituents α described below. Selected from the group consisting of an aryl group having 6 to 10 carbon atoms optionally having 1 to 3 or an oxygen atom, a nitrogen atom, and a sulfur atom optionally having 1 to 3 substituents α described below. Ring or 2 containing 1 to 4 heteroatoms
A 5- to 10-membered heteroaromatic ring group, wherein the substituent α is (i) a linear or branched alkyl group having 1 to 6 carbon atoms, and (ii) a 1 to 4 carbon atoms. A straight-chain or branched-chain alkyl halide group having (i) a hydroxy group;
v) a linear or branched aliphatic acyloxy group having 1 to 4 carbon atoms, (v) a C1 to 4 carbon atom
Linear or branched alkoxy groups having
(Vi) a linear or branched alkylenedioxy group having 1 to 4 carbon atoms; (vii) an aralkyloxy group having 7 to 12 carbon atoms; (viii) a aralkyloxy group having 1 to 4 carbon atoms. A straight or branched alkylthio group having 1 to 4 carbon atoms, (ix) a straight or branched alkylsulfonyl group having 1 to 4 carbon atoms, (x) a halogen atom,
(xiii) linear or branched dialkylamino groups having the same or different alkyls each having 1 to 4 carbon atoms, (xiii) having 7 carbon atoms
(Xiv) an aryl group having 6 to 10 carbon atoms (where the aryl moiety is a linear or branched alkyl having 1 to 6 carbon atoms, 1 to 4 carbon atoms) Linear or branched alkyl halide having 1 to 4 carbon atoms, linear or branched alkoxy having 1 to 4 carbon atoms, halogen or linear or branched alkyl having 1 to 4 carbon atoms. (Xv) an aryloxy group having 6 to 10 carbon atoms (where the aryl moiety is a linear or branched having 1 to 6 carbon atoms) Linear alkyl, linear or branched alkyl halide having 1 to 4 carbon atoms, linear or branched alkoxy having 1 to 4 carbon atoms, (Xvi) an arylthio group having 6 to 10 carbon atoms (the aryl moiety may be substituted with a linear or branched alkylenedioxy having 1 to 4 carbon atoms); Linear or branched alkyl having 1 to 6 carbons, linear or branched alkyl halide having 1 to 4 carbons, 1 to 4 carbons
May be substituted with a straight-chain or branched alkoxy having one or two carbon atoms, a halogen or a straight-chain or branched alkylenedioxy having 1 to 4 carbon atoms. (Xvii) an arylsulfonyl group having 6 to 10 carbon atoms (where the aryl moiety is a straight-chain or branched alkyl having 1 to 6 carbons, a straight-chain having 1 to 4 carbons) Or branched alkyl halides, straight or branched alkoxy having 1 to 4 carbon atoms, halogen or straight or branched alkyl having 1 to 4 carbon atoms (Xvi may be substituted with dioxy).
ii) an arylsulfonylamino group having 6 to 10 carbon atoms (the aryl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl having 1 to 4 carbons) Branched alkyl halide, straight or branched alkoxy having 1 to 4 carbon atoms, halogen or 1 to 4 carbon atoms
It may be substituted by a straight-chain or branched alkylenedioxy having two or more carbon atoms. The nitrogen atom of the amino moiety may be substituted with a linear or branched alkyl having 1 to 6 carbons. (Xix) one ring or two containing 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur
A 5- to 10-membered heteroaromatic ring group, (xx) an oxygen atom,
A monocyclic or bicyclic 5- to 10-membered heteroaromatic oxy group containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom and a sulfur atom; (xxi) consisting of an oxygen atom, a nitrogen atom and a sulfur atom A monocyclic or bicyclic 5- to 10-membered heteroaromatic thio group containing 1 to 4 heteroatoms selected from the group; (xxiii) a heteroatom selected from the group consisting of oxygen, nitrogen and sulfur A monocyclic or bicyclic 5- to 10-membered heteroaromatic ring sulfonyl group containing 1 to 4
(Xxiii) a monocyclic or bicyclic 5- to 10-membered heteroaromatic sulfonylamino group containing 1 to 4 heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom (the nitrogen atom in the amino moiety May be substituted with linear or branched alkyl having 1 to 6 carbons), and Y is an oxygen atom, a sulfur atom or a compound of the formula> N A group having —R ⁴ (wherein R ⁴ is a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, or a linear or branched alkyl group having 1 to 8 carbon atoms) A linear aliphatic acyl group or an aromatic acyl group). And a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof as an active ingredient. 2. The phenylalkylcarboxylic acid derivative according to claim 1, wherein R ¹ is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, a pharmaceutically acceptable derivative thereof. Or a pharmacologically acceptable ester thereof as an active ingredient. 3. The phenylalkylcarboxylic acid derivative according to claim 1, wherein R ¹ is a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, and a pharmaceutically acceptable derivative thereof. Or a pharmacologically acceptable ester thereof as an active ingredient. 4. The phenylalkylcarboxylic acid derivative according to claim 1, wherein R ¹ is a hydrogen atom or an alkyl group having 1 or 2 carbon atoms, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable salt thereof. An insulin resistance improving agent containing an ester as an active ingredient. 5. The method according to claim 1, wherein R ¹ is an alkyl group having 1 or 2 carbon atoms, a phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof. An insulin resistance improving agent contained as a component. 6. The phenylalkylcarboxylic acid derivative according to claim 1, wherein R ² is a linear or branched alkylene group having 2 to 5 carbon atoms, a pharmaceutically acceptable salt thereof or An insulin resistance improving agent containing the pharmacologically acceptable ester as an active ingredient. 7. The phenylalkylcarboxylic acid derivative according to claim 1, wherein R ² is a linear or branched alkylene group having 2 to 4 carbon atoms, a pharmaceutically acceptable salt thereof or An insulin resistance improving agent containing the pharmacologically acceptable ester as an active ingredient. 8. The method according to claim 1, wherein a phenylalkylcarboxylic acid derivative wherein R ² is an ethylene group, a trimethylene group or a methylethylene group, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable ester thereof is used as an active ingredient. Insulin resistance improving agent contained as a drug. 9. The method according to claim 1, wherein the phenylalkylcarboxylic acid derivative wherein R ² is an ethylene group, a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof as an active ingredient. Agent. 10. The method according to claim 1, wherein R ³ is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, An agent for improving insulin resistance comprising as an active ingredient a phenylalkylcarboxylic acid derivative which is an alkylthio group or a halogen atom having several or two, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof. 11. The method according to claim 1, wherein the phenylalkylcarboxylic acid derivative wherein R ³ is a hydrogen atom, a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof as an active ingredient. Agent. 12. The method according to claim 1, wherein X is 1 to 3
Aryl groups having 6 to 10 carbon atoms optionally having a substituent α described later, or 1 to 3 oxygen atoms, nitrogen atoms and sulfur optionally having a substituent α described below A 5- to 10-membered heteroaromatic group (comprising one or two rings) containing 1 to 4 heteroatoms selected from the group consisting of atoms, wherein the substituent α is (i) Linear or branched alkyl having 1 to 6 carbons, (ii) linear or branched alkyl halide having 1 to 4 carbons, (iii) hydroxy, (iv )
A straight-chain or branched alkanoyloxy having 1 to 4 carbon atoms, (v) a straight-chain or branched alkoxy having 1 to 4 carbon atoms, (vi)
Linear or branched alkylenedioxy having 1 to 4 carbon atoms, (vii) 7 to 12 carbon atoms
Aralkyloxy having (viii) 1 carbon atoms
(Ix) linear or branched alkylsulfonyl having 1 to 4 carbon atoms, (x) fluorine atom, (xi) chlorine atom (Xii) a bromine atom,
(Xiii) aralkyl having 7 to 12 carbon atoms, (xiv) phenyl (the phenyl moiety has 1 carbon atom)
Linear or branched alkyl having 1 to 4 carbon atoms, linear or branched alkyl halide having 1 to 4 carbon atoms, linear or branched alkyl having 1 to 4 carbon atoms, It may be substituted by a branched alkoxy, a halogen or a linear or branched alkylenedioxy having 1 to 4 carbon atoms. ),
(Xv) phenoxy (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl halide having 1 to 4 carbons, carbon Linear or branched alkoxy having 1 to 4 carbon atoms, halogen or 1 carbon atom
And may be substituted with a straight-chain or branched alkylenedioxy having 4 to 4 carbon atoms. ), (Xvi)
Phenylthio (the phenyl moiety is a straight-chain or branched alkyl having 1 to 6 carbons, a straight-chain or branched alkyl halide having 1 to 4 carbons, (Xvii) straight-chain or branched alkoxy having 4 carbon atoms, halogen or straight-chain or branched alkylenedioxy having 1 to 4 carbon atoms.), (Xvii) Phenylsulfonyl (the phenyl moiety is a straight-chain or branched alkyl having 1 to 6 carbons,
Straight-chain or branched alkyl halide having 1 to 4 carbon atoms, straight-chain or branched alkoxy having 1 to 4 carbon atoms, halogen or straight-chain having 1 to 4 carbon atoms Alternatively, it may be substituted with a branched alkylenedioxy. ), (Xviii)
Phenylsulfonylamino (the phenyl moiety has 1 carbon atom)
Linear or branched alkyl having 1 to 4 carbon atoms, linear or branched alkyl halide having 1 to 4 carbon atoms, linear or branched alkyl having 1 to 4 carbon atoms, It may be substituted by a branched alkoxy, a halogen or a linear or branched alkylenedioxy having 1 to 4 carbon atoms. The nitrogen atom of the amino moiety may be substituted with a linear or branched alkyl having 1 to 6 carbons. ), (Xix) ruffle, (xx) thienyl,
(Xxi) oxazolyl, (xxii) isoxazolyl, (xxiii) thiazolyl, (xxiv) pyridyl, (xxv) pyridyloxy, (xxvi) pyridylthio, (xxvii) pyridylsulfonyl,
(Xxviii) imidazolyl (the nitrogen atom of the ring may be substituted by linear or branched alkyl having 1 to 6 carbon atoms) and (xxix) pyridylsulfonylamino (nitrogen of the amino moiety Wherein the atoms may be substituted by linear or branched alkyl having 1 to 6 carbon atoms.) Phenylalkylcarboxylic acid derivatives which are selected from the group consisting of
An insulin sensitizing agent comprising a pharmacologically acceptable salt or a pharmacologically acceptable ester thereof as an active ingredient. 13. The method according to claim 1, wherein X is 1 to 3
Phenyl groups optionally having a substituent α described below,
A naphthyl group, an imidazolyl group, an oxazolyl group, a pyridyl group, an indolyl group, a quinolyl group or an isoquinolyl group, wherein the substituent α is (i) a linear or branched chain having 1 to 6 carbon atoms. Alkyl, (ii) linear or branched alkyl halide having 1 to 4 carbon atoms, (iii) hydroxy, (iv)
A straight-chain or branched alkanoyloxy having 1 to 4 carbon atoms, (v) a straight-chain or branched alkoxy having 1 to 4 carbon atoms, (vi)
Methylenedioxy, (vii) aralkyloxy having 7 to 12 carbon atoms, (viii) linear or branched alkylthio having 1 to 4 carbon atoms, (ix) 1 to 4 carbon atoms (X) a fluorine atom, (xi) a chlorine atom, (xiii) a bromine atom, (xiii) an aralkyl having 7 to 12 carbon atoms, (xiv) phenyl The phenyl moiety is methyl,
It may be substituted with trifluoromethyl, methoxy, fluoro or methylenedioxy. (Xv) phenoxy (the phenyl moiety may be substituted with methyl, trifluoromethyl, methoxy, fluoro or methylenedioxy), (xvi) phenylthio (the phenyl moiety is methyl, trifluoromethyl, methoxy , Phenylsulfonyl, wherein the phenyl moiety is methyl, trifluoromethyl, methoxy,
It may be substituted by fluoro or methylenedioxy. ), (Xviii) phenylsulfonylamino (the phenyl moiety may be substituted by methyl, trifluoromethyl, methoxy, fluoro or methylenedioxy, wherein the nitrogen atom of the amino moiety has 1 to 6 carbon atoms)
May be substituted with a straight-chain or branched-chain alkyl. ), (Xix) ruffle, (xx)
Thienyl, (xxi) oxazolyl, (xxii)
Isoxazolyl, (xxiii) thiazolyl,
(Xxiv) pyridyl, (xxv) pyridyloxy,
(Xxvi) pyridylthio, (xxvii) pyridylsulfonyl, (xxviii) imidazolyl (the nitrogen atom of the ring may be substituted by linear or branched alkyl having 1 to 6 carbon atoms) and xxix) pyridylsulfonylamino, wherein the nitrogen atom of the amino moiety may be substituted by linear or branched alkyl having 1 to 6 carbon atoms. An insulin resistance improving agent comprising a phenylalkylcarboxylic acid derivative, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable ester thereof as an active ingredient. 14. The method according to claim 1, wherein X is 1 to 3
Phenyl groups optionally having a substituent α described below,
A naphthyl group, an imidazolyl group, an oxazolyl group, a pyridyl group, an indolyl group, a quinolyl group or an isoquinolyl group, wherein the substituent α is (i) a linear or branched chain having 1 to 6 carbon atoms. Alkyl, (ii) linear or branched alkyl halide having 1 to 4 carbon atoms, (iii) hydroxy, (iv)
A straight-chain or branched alkanoyloxy having 1 to 4 carbon atoms, (v) a straight-chain or branched alkoxy having 1 to 4 carbon atoms, (vi)
Methylenedioxy, (vii) benzyloxy,
(Viii) phenethyloxy, (ix) naphthylmethoxy, (x) linear or branched alkylthio having 1 to 4 carbons, (xi) linear or branched alkylthio having 1 to 4 carbons (Xiii) fluorine atom, (xiii) chlorine atom, (xiv) bromine atom, (xv) benzyl,
(Xvi) phenyl (the phenyl moiety may be substituted with methyl, trifluoromethyl, methoxy, fluoro or methylenedioxy), (xvii) phenoxy (the phenyl moiety is methyl, trifluoromethyl, methoxy, fluoro Or (xviii) phenylthio, (xix) phenylsulfonyl, (xx) phenylsulfonylamino, (xxi) N-methylphenylsulfonylamino, (xxii) furyl, (xx
iii) thienyl, (xxiv) oxazolyl, (x
xx) isoxazolyl, (xxvi) thiazolyl,
(Xxvii) pyridyl, (xxviii) pyridyloxy, (xxix) pyridylthio, (xxx) pyridylsulfonyl, (xxxi) pyridylsulfonylamino, (xxxi)
i) N-methylpyridylsulfonylamino and (x
xxiii) phenylalkylcarboxylic acid selected from the group consisting of imidazolyl (the ring nitrogen atom may be substituted by linear or branched alkyl having 1 to 6 carbon atoms) An insulin sensitizing agent comprising a derivative, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable ester thereof as an active ingredient. 15. The method according to claim 1, wherein X is 1 to 2
Phenyl groups optionally having a substituent α described below,
A naphthyl group, a pyridyl group, an indolyl group, a quinolyl group or an isoquinolyl group, wherein the substituent α is a linear or branched alkyl having 1 to 3 carbon atoms, 1 to 3 fluorine atoms Methyl having 1 to 2 carbon atoms, alkanoyloxy having 1 to 2 carbon atoms, linear or branched alkoxy having 1 to 3 carbon atoms,
Methylenedioxy, benzyloxy, alkylthio having 1 or 2 carbon atoms, 1 carbon atom
Alkylsulfonyl having two or more, fluorine, chlorine, bromine, benzyl, phenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 3,4-methylenedioxy Phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, furyl, thienyl, oxazolyl, thiazolyl, imidazolyl, N-
A phenylalkylcarboxylic acid derivative selected from the group consisting of methylimidazolyl, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino; a pharmaceutically acceptable salt thereof; An insulin sensitizing agent containing an acceptable ester as an active ingredient. 16. The method according to claim 1, wherein X is one phenyl group, naphthyl group, pyridyl group, quinolyl group or isoquinolyl group which may have one substituent α described below, wherein α is methyl, ethyl, isopropyl,
Trifluoromethyl, hydroxy, acetoxy, methoxy, ethoxy, isopropoxy, methylenedioxy, benzyloxy, alkylthio having 1 to 2 carbons, alkylsulfonyl having 1 to 2 carbons,
Chlorine atom, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl,
Pyridyloxy, pyridylthio, pyridylsulfonyl,
Insulin resistance containing a phenylalkyl carboxylic acid derivative selected from the group consisting of pyridylsulfonylamino and N-methylpyridylsulfonylamino, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable ester thereof as an active ingredient An improving agent. 17. The method according to claim 1, wherein X is one phenyl group which may have a substituent α described below, wherein the substituent α is methyl, hydroxy, acetoxy, chlorine atom, Is selected from the group consisting of benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl; or Wherein the substituent α is methoxy, ethoxy, isopropoxy, benzyloxy, alkylthio having 1 to 2 carbons, and 1 to 2 carbons. Having alkylsulfonyl, benzyl, phenyl, phenoxy, phenylthio, phenyl Insulin containing a phenylalkylcarboxylic acid derivative selected from the group consisting of sulfonyl, phenylsulfonylamino and N-methylphenylsulfonylamino, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable ester thereof as an active ingredient A resistance improving agent. 18. The method according to claim 1, wherein X is one phenyl group optionally having a substituent α described below, wherein the substituent α is a hydroxy, chlorine atom, benzyl, phenyl, Phenoxy, phenylthio, pyridyl,
An insulin sensitizing agent comprising, as an active ingredient, a phenylalkylcarboxylic acid derivative selected from the group consisting of pyridyloxy and pyridylthio, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable ester thereof. 19. The method according to claim 1, wherein Y is an oxygen atom,
A sulfur atom or a group having the formula> NR ⁴ , wherein R ⁴
Represents a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, or a linear or branched alkanoyl group having 2 to 5 carbon atoms. A) a phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof as an active ingredient. 20. The insulin resistance-improving action according to claim 1, which comprises a phenylalkylcarboxylic acid derivative wherein Y is an oxygen atom, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable ester thereof as an active ingredient. Agent. 21. The phenylalkylcarboxylic acid derivative according to claim 1, wherein Z is a single bond or a linear or branched alkylene group having 1 to 4 carbon atoms, and a pharmaceutically acceptable derivative thereof. An agent for improving insulin resistance comprising a salt or a pharmaceutically acceptable ester thereof as an active ingredient. 22. The phenylalkylcarboxylic acid derivative according to claim 1, wherein Z is a linear or branched alkylene group having 1 to 4 carbon atoms, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable salt thereof. An agent for improving insulin resistance comprising a pharmacologically acceptable ester as an active ingredient. 23. The method according to claim 1, wherein Z is an alkylene group having 1 or 2 carbon atoms, a phenylalkylcarboxylic acid derivative, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable ester thereof as an active ingredient. Insulin resistance improving agent contained as a drug. 24. The method of claim 1, wherein the phenylalkylcarboxylic acid derivative wherein Z is a methylene group, a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof is contained as an active ingredient to improve insulin resistance. Agent. 25. The method according to claim 1, wherein W is (i) a linear or branched alkyl group having 1 to 6 carbon atoms, and (ii) a linear chain having 1 to 4 carbon atoms. (Iii) a linear or branched alkylthio group having 1 to 4 carbon atoms, (iv) a linear or branched alkyl group having 1 to 4 carbon atoms Chain-like monoalkylamino group,
(V) linear or branched dialkylamino groups having the same or different alkyls each having 1 to 4 carbon atoms; (vi) linear or branched dialkylamino groups having 1 to 4 carbon atoms. An N-alkyl-N-arylamino group having 1 to 3 aryl groups having 6 to 10 carbon atoms which may have a substituent α described below in the alkyl and aryl moieties of (vii) 1 to 3 aryloxy groups having 6 to 10 carbon atoms optionally having a substituent α described below, (v
iii) an arylthio group having 6 to 10 carbon atoms which may have 1 to 3 substituents α described later in the aryl moiety, and (ix) 1 to 3 substituents α described later in the aryl moiety. An arylamino group having 6 to 10 carbon atoms which may be possessed; (x) an aralkyl having 1 to 3 carbon atoms having 7 to 12 carbon atoms which may have a substituent α described later in the aryl moiety; Group, (x
i) a 1-pyrrolyl group, (xiii) a 1-pyrrolidinyl group, (xiii) a 1-imidazolyl group, (xiv) a piperidino group or (x
v) a morpholino group, wherein the substituted α is (i) a linear or branched alkyl having 1 to 6 carbons, (ii) a linear alkyl having 1 to 4 carbons Or a branched alkyl halide, (iii) hydroxy, (iv)
A straight-chain or branched alkanoyloxy having 1 to 4 carbon atoms, (v) a straight-chain or branched alkoxy having 1 to 4 carbon atoms, (vi)
Linear or branched alkylenedioxy having 1 to 4 carbon atoms, (vii) 7 to 12 carbon atoms
Aralkyloxy having (viii) 1 carbon atoms
(Ix) linear or branched alkylsulfonyl having 1 to 4 carbon atoms, (x) fluorine atom, (xi) chlorine atom (Xii) a bromine atom,
(Xiii) aralkyl having 7 to 12 carbon atoms, (xiv) phenyl (the phenyl moiety has 1 carbon atom)
Linear or branched alkyl having 1 to 4 carbon atoms, linear or branched alkyl halide having 1 to 4 carbon atoms, linear or branched alkyl having 1 to 4 carbon atoms, It may be substituted by a branched alkoxy, a halogen or a linear or branched alkylenedioxy having 1 to 4 carbon atoms. ),
(Xv) phenoxy (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl halide having 1 to 4 carbons, carbon Linear or branched alkoxy having 1 to 4 carbon atoms, halogen or 1 carbon atom
And may be substituted with a straight-chain or branched alkylenedioxy having 4 to 4 carbon atoms. ), (Xvi)
Phenylthio (the phenyl moiety is a straight-chain or branched alkyl having 1 to 6 carbons, a straight-chain or branched alkyl halide having 1 to 4 carbons, (Xvii) straight-chain or branched alkoxy having 4 carbon atoms, halogen or straight-chain or branched alkylenedioxy having 1 to 4 carbon atoms.), (Xvii) Phenylsulfonyl (the phenyl moiety is a straight-chain or branched alkyl having 1 to 6 carbons,
Straight-chain or branched alkyl halide having 1 to 4 carbon atoms, straight-chain or branched alkoxy having 1 to 4 carbon atoms, halogen or straight-chain having 1 to 4 carbon atoms Alternatively, it may be substituted with a branched alkylenedioxy. ), (Xviii)
Phenylsulfonylamino (the phenyl moiety has 1 carbon atom)
Linear or branched alkyl having 1 to 4 carbon atoms, linear or branched alkyl halide having 1 to 4 carbon atoms, linear or branched alkyl having 1 to 4 carbon atoms, It may be substituted by a branched alkoxy, a halogen or a linear or branched alkylenedioxy having 1 to 4 carbon atoms. The nitrogen atom of the amino moiety may be substituted with a linear or branched alkyl having 1 to 6 carbons. ), (Xix) ruffle, (xx) thienyl,
(Xxi) oxazolyl, (xxii) isoxazolyl, (xxiii) thiazolyl, (xxiv) pyridyl, (xxv) pyridyloxy, (xxvi) pyridylthio, (xxvii) pyridylsulfonyl,
(Xxviii) imidazolyl (the nitrogen atom of the ring may be substituted by linear or branched alkyl having 1 to 6 carbon atoms) and (xxix) pyridylsulfonylamino (nitrogen of the amino moiety Wherein the atoms may be substituted by linear or branched alkyl having 1 to 6 carbon atoms.) Phenylalkylcarboxylic acid derivatives which are selected from the group consisting of
An insulin sensitizing agent comprising a pharmacologically acceptable salt or a pharmacologically acceptable ester thereof as an active ingredient. 26. The method according to claim 1, wherein W is (i) a linear or branched alkyl group having 1 to 6 carbon atoms, and (ii) a straight chain having 1 to 4 carbon atoms. (Iii) a linear or branched alkylthio group having 1 to 4 carbon atoms, (iv) a linear or branched alkyl group having 1 to 4 carbon atoms Chain-like monoalkylamino group,
(V) linear or branched dialkylamino groups having the same or different alkyls each having 1 to 4 carbon atoms; (vi) linear or branched dialkylamino groups having 1 to 4 carbon atoms. An N-alkyl-N-arylamino group having 1 to 3 aryl groups having 6 to 10 carbon atoms which may have a substituent α described below in the alkyl and aryl moieties of (vii) 1 to 3 aryloxy groups having 6 to 10 carbon atoms optionally having a substituent α described below, (v
iii) an arylthio group having 6 to 10 carbon atoms which may have 1 to 3 substituents α described later in the aryl moiety, and (ix) 1 to 3 substituents α described later in the aryl moiety. An arylamino group having 6 to 10 carbon atoms which may be possessed; (x) an aralkyl having 1 to 3 carbon atoms having 7 to 12 carbon atoms which may have a substituent α described later in the aryl moiety; Group or
(Xi) a 1-pyrrolyl group, wherein the substituted α is hydroxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, pyridyl,
An insulin sensitizing agent comprising, as an active ingredient, a phenylalkylcarboxylic acid derivative selected from the group consisting of pyridyloxy and pyridylthio, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable ester thereof. 27. The method according to claim 1, wherein W is (i) a linear or branched alkyl group having 1 to 4 carbon atoms, and (ii) a linear chain having 1 to 4 carbon atoms. (Iii) a linear or branched alkylthio group having 1 to 4 carbon atoms, (iv) a linear or branched alkyl group having 1 to 4 carbon atoms Chain-like monoalkylamino group,
(V) linear or branched dialkylamino groups having the same or different alkyls each having 1 to 4 carbon atoms; (vi) linear or branched dialkylamino groups having 1 to 4 carbon atoms. Alkyl and C 6 -C 10
An N-alkyl-N-arylamino group having an aryl having two or more (vii) phenoxy groups, (vii
i) phenylthiothio group, (ix) phenylamino group, (x) aralkyl group having 7 to 10 carbon atoms, (xi) 1-pyrrolyl group, (xii) 1-pyrrolidinyl group or (xiii) 1-imidazolyl An insulin sensitizing agent comprising, as an active ingredient, a phenylalkylcarboxylic acid derivative as a group, a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof. 28. The method according to claim 1, wherein W is (i) a propyl or butyl group, and (ii) C 1 to C 3
Linear or branched alkoxy groups having
(Iii) a straight-chain or branched alkylthio group having 1 to 3 carbon atoms, (iv) a straight-chain or branched monoalkylamino group having 1 to 3 carbon atoms, (v ) Diethylamino group, (vi) N-phenyl-N-ethylamino group, (vii) phenoxy group, (viii) phenylthio group, (ix) phenylamino group, (x) 3-phenylpropyl group, (x
i) 4-phenylbutyl group or (xii) a phenylalkylcarboxylic acid derivative which is a 1-pyrrolyl group, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof as an active ingredient, an agent for improving insulin resistance. . 29. The method according to claim 1, wherein W is butyl, ethoxy, methylthio, ethylamino, diethylamino, N-phenyl-N-ethylamino, phenoxy, phenylthio, phenylamino, 3-
An insulin resistance improving agent comprising, as an active ingredient, a phenylalkylcarboxylic acid derivative which is a phenylpropyl group or a 1-pyrrolyl group, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable ester thereof. 30. The method according to claim 1, wherein W is a butyl group,
Ethoxy, methylthio, ethylamino, phenoxy, phenylthio, phenylamino or 3-
An insulin resistance improving agent comprising a phenylalkylcarboxylic acid derivative which is a phenylpropyl group, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof as an active ingredient. 31. The method according to claim 1, wherein R ¹ is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms; R ² is a group having 2 to 5 carbon atoms. R ³ is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkylene group having 1 to 4 carbon atoms,
An alkoxy group having 1 to 2 carbon atoms, an alkylthio group having 1 to 2 carbon atoms or a halogen atom;
Is a single bond or a linear or branched alkylene group having 1 to 4 carbon atoms; W is (i) a linear or branched alkyl group having 1 to 6 carbon atoms (Ii) a linear or branched alkoxy group having 1 to 4 carbon atoms, (iii) a linear or branched alkylthio group having 1 to 4 carbon atoms, (iv) A linear or branched monoalkylamino group having 1 to 4 carbon atoms, (v)
The same or different, each alkyl is a straight-chain or branched dialkylamino group having 1 to 4 carbon atoms, (vi) a straight-chain or branched alkyl having 1 to 4 carbon atoms, and An N-alkyl-N-arylamino group having 1 to 3 aryls having 6 to 10 carbon atoms which may have a substituent α described below, which is described later, and (vii) 1 to 3 3 to 3 aryloxy groups having 6 to 10 carbon atoms which may have a substituent α described below, and (viii) having 1 to 3 substituents α described later in the aryl moiety. An arylthio group having 6 to 10 carbon atoms which may be substituted, or (ix) having no 1 to 3 carbon atoms which may have 1 to 3 substituents α described later in the aryl portion, which will be described later. (X) 1 to 3 aralkyl groups having 7 to 12 carbon atoms which may have a substituent α described later in the aryl portion, and (xi) 1-pyrrolyl A group, (xii) a 1-pyrrolidinyl group, (xii)
i) a 1-imidazolyl group, (xiv) a piperidino group or (xv) a morpholino group; and X has 1 to 3 carbon atoms and 6 to 10 carbon atoms which may have a substituent α described later. Aryl group, or 1-3
A 5- to 10-membered ring (1 ring or 1 ring) containing 1 to 4 hetero atoms selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom optionally having Wherein the substituent α described later is: (i) a linear or branched alkyl having 1 to 6 carbon atoms,
(Ii) a linear or branched alkyl halide having 1 to 4 carbon atoms, (iii) hydroxy, (iv) a linear or branched alkanoyl having 1 to 4 carbon atoms. Oxy, (v) carbon number 1
Linear or branched alkoxy having 4 to 4 carbon atoms, (vi) linear or branched alkylenedioxy having 1 to 4 carbon atoms, (vii) 7 to 12 carbon atoms. Having aralkyloxy, (vii
i) a linear or branched alkylthio having 1 to 4 carbons, (ix) a linear or branched alkylsulfonyl having 1 to 4 carbons,
(X) a fluorine atom, (xi) a chlorine atom, (xii)
A bromine atom, (xiii) an aralkyl having 7 to 12 carbon atoms, (xiv) phenyl (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbon atoms, and 1 to 4 carbon atoms) A straight-chain or branched alkyl halide having 1 to 4 carbon atoms, a straight-chain or branched alkoxy having 1 to 4 carbon atoms, a halogen or a straight-chain or branched alkyl having 1 to 4 carbon atoms (Xv) phenoxy (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, 1 to 4 carbons) A straight-chain or branched alkyl halide having 1 to 4 carbon atoms, a straight-chain or branched alkoxy having 1 to 4 carbon atoms, halogen or 1 to 4 carbon atoms. That may be substituted with a straight-chain or branched alkylenedioxy.),
(Xvi) phenylthio, wherein the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons,
Straight or branched alkyl halide having 1 to 4 carbon atoms, straight or branched alkoxy having 1 to 4 carbon atoms, halogen or having 1 to 4 carbon atoms It may be substituted with a linear or branched alkylenedioxy. ), (Xv
ii) phenylsulfonyl (the phenyl moiety has 1 carbon atom)
Linear or branched alkyl having 1 to 4 carbon atoms, linear or branched alkyl halide having 1 to 4 carbon atoms, linear or branched alkyl having 1 to 4 carbon atoms, It may be substituted by a branched alkoxy, a halogen or a linear or branched alkylenedioxy having 1 to 4 carbon atoms. ),
(Xviii) phenylsulfonylamino (where the phenyl moiety is a linear or branched alkyl having 1 to 6 carbons, a linear or branched alkyl halide having 1 to 4 carbons) May be substituted by linear or branched alkoxy having 1 to 4 carbons, halogen, or linear or branched alkylenedioxy having 1 to 4 carbons. The nitrogen atom of the amino moiety may be substituted by a linear or branched alkyl having 1 to 6 carbon atoms.), (Xix) furyl, (xx) thienyl, (xxi) oxazolyl, (Xxii) isoxazolyl, (xxiii) thiazolyl, (xxi)
v) pyridyl, (xxv) pyridyloxy, (xx
vi) pyridylthio, (xxvii) pyridylsulfonyl, (xxviii) imidazolyl (the nitrogen atom of the ring may be substituted by linear or branched alkyl having 1 to 6 carbon atoms) and (xxi)
x) pyridylsulfonylamino, wherein the nitrogen atom of the amino moiety may be substituted by a straight-chain or branched alkyl having 1 to 6 carbon atoms. ; Y is an oxygen atom, in a sulfur atom or the formula> N-R ⁴ group having the formula (, R ⁴ is a hydrogen atom,
It represents a linear or branched alkyl group having 1 to 3 carbon atoms or a linear or branched alkanoyl group having 2 to 5 carbon atoms. A) phenylalkylcarboxylic acid derivative, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable ester thereof as an active ingredient; 32. The method according to claim 1, wherein R ¹ is a linear or branched alkyl group having 1 to 4 carbon atoms; R ² is a linear chain having 2 to 5 carbon atoms. A branched or branched alkylene group;
R ³ is hydrogen atom; Z is a straight-chain or branched alkylene group having four C 1 -C; W straight or correspondingly with the six to (i) C 1 -C A branched alkyl group; (ii) a linear or branched alkoxy group having 1 to 4 carbon atoms;
ii) a linear or branched alkylthio group having 1 to 4 carbon atoms, (iv) a linear or branched monoalkylamino group having 1 to 4 carbon atoms, (v) The same or different, each alkyl is a straight-chain or branched dialkylamino group having 1 to 4 carbon atoms, (vi) a straight-chain or branched alkyl having 1 to 4 carbon atoms, and An N-alkyl-N-arylamino group having 1 to 3 aryl groups having 6 to 10 carbon atoms which may have a substituent α described below in the aryl moiety, and (vii) 1 to 3 in the aryl moiety. Aryloxy groups having 6 to 10 carbon atoms which may have a substituent α described below,
(Viii) an arylthio group having 1 to 3 carbon atoms having 6 to 10 carbon atoms which may have a substituent α described later, and (ix) an aryl moiety having 1 to 3 substituents α described later in the aryl moiety. An arylamino group having 6 to 10 carbon atoms which may have (x) an aryl moiety having 1 to 3 carbon atoms having 7 to 12 carbon atoms which may have a substituent α described later. An aralkyl group or (xi) 1-pyrrolyl group; X is one phenyl group which may have a substituent α described later, wherein the substituent α is a hydroxy, chlorine atom, benzyl, phenyl , Phenoxy, phenylthio, pyridyl,
Insulin selected from the group consisting of pyridyloxy and pyridylthio; Y is an oxygen atom; a phenylalkylcarboxylic acid derivative, a pharmaceutically acceptable salt thereof or an insulin containing a pharmaceutically acceptable ester thereof as an active ingredient A resistance improving agent. 33. The method according to claim 1, wherein R ¹ is an alkyl group having 1 or 2 carbon atoms;
R ² is an ethylene group; R ³ is a hydrogen atom; Z is a methylene group; W is (i) a propyl or butyl group; (ii) a straight or branched chain having 1 to 3 carbon atoms. A chain alkoxy group, (iii) carbon number 1
A straight-chain or branched alkylthio group having 1 to 3 carbon atoms, (iv) a straight-chain or branched monoalkylamino group having 1 to 3 carbon atoms, (v) a diethylamino group, (vi ) N-phenyl-N-ethylamino group, (vii) phenoxy group, (viii)
A phenylthio group, (ix) a phenylamino group,
(X) a 3-phenylpropyl group, (xi) a 4-phenylbutyl group or (xii) a 1-pyrrolyl group;
X is one phenyl group which may have a substituent α described below, wherein the substituent α is methyl, hydroxy, acetoxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenyl Pyridyl which is selected from the group consisting of sulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl; or X is a pyridyl optionally having one substituent α described later. Wherein the substituent α is methoxy, ethoxy, isopropoxy, benzyloxy, alkylthio having 1 or 2 carbons, alkylsulfonyl having 1 or 2 carbons, benzyl, phenyl, phenoxy, phenylthio, Phenylsulfonyl, phenylsulfonylamino And N-methylphenylsulfonylamino; Y is an oxygen atom; a phenylalkylcarboxylic acid derivative, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable ester thereof as an active ingredient An insulin resistance improving agent to be contained. 34. The method of claim 1, wherein R ¹ is an alkyl group having 1 or 2 carbon atoms;
R ² is an ethylene group; R ³ is a hydrogen atom; Z is a methylene group; W is (i) a propyl or butyl group; (ii) a straight or branched chain having 1 to 3 carbon atoms. A chain alkoxy group, (iii) carbon number 1
A straight-chain or branched alkylthio group having 1 to 3 carbon atoms, (iv) a straight-chain or branched monoalkylamino group having 1 to 3 carbon atoms, (v) a diethylamino group, (vi A) N-phenyl-N-ethylamino group, (vii) a phenoxy group, (viii)
A phenylthio group, (ix) a phenylamino group,
(X) a 3-phenylpropyl group, (xi) a 4-phenylbutyl group or (xii) a 1-pyrrolyl group;
X is one phenyl group optionally having a substituent α described below, wherein the substituent α is a hydroxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, pyridyl,
Insulin selected from the group consisting of pyridyloxy and pyridylthio; Y is an oxygen atom; a phenylalkylcarboxylic acid derivative, a pharmaceutically acceptable salt thereof or an insulin containing a pharmaceutically acceptable ester thereof as an active ingredient A resistance improving agent. 35. The method according to claim 1, wherein R ¹ is an alkyl group having 1 or 2 carbon atoms;
R ² is an ethylene group; R ³ is a hydrogen atom; Z is a methylene group; W is a butyl group, an ethoxy group, a methylthio group, an ethylamino group, a diethylamino group, an N-phenyl-N-ethylamino group Phenoxy, phenylthio, phenylamino, 3-phenylpropyl or 1-pyrrolyl; X is one phenyl which may have a substituent α described below, α is hydroxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, pyridyl,
Insulin selected from the group consisting of pyridyloxy and pyridylthio; Y is an oxygen atom; a phenylalkylcarboxylic acid derivative, a pharmaceutically acceptable salt thereof or an insulin containing a pharmaceutically acceptable ester thereof as an active ingredient A resistance improving agent. 36. The method of claim 1, wherein R ¹ is an alkyl group having 1 or 2 carbon atoms;
R ² is an ethylene group; R ³ is a hydrogen atom; Z is a methylene group; W is a butyl group, an ethoxy group, a methylthio group, an ethylamino group, a phenoxy group, a phenylthio group, a phenylamino group or X is a phenyl group optionally having one substituent α described below, wherein the substituent α is a hydroxy, chlorine atom, benzyl, phenyl, phenoxy, phenylthio, pyridyl,
Insulin selected from the group consisting of pyridyloxy and pyridylthio; Y is an oxygen atom; a phenylalkylcarboxylic acid derivative, a pharmaceutically acceptable salt thereof or an insulin containing a pharmaceutically acceptable ester thereof as an active ingredient A resistance improving agent. 37. The method according to claim 1, wherein 1) 2-ethoxy-3- [4- [2-[[1- (4-biphenylyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2) 2 -Ethoxy-3- [4- [2-[[1- (4-phenylsulfonylphenyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid; 3) 2-ethoxy-3- [4- [2-[[ 1- [4-
(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 4) 2-ethoxy-3- [4- [2-[[1- [4-]
(3-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 5) 2-ethoxy-3- [4- [2-[[1- [4-]
(4-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 6) 2-ethoxy-3- [4- [2-[[1- (2-phenyl-5-pyridyl) ethylidene] aminooxy ] Ethoxy] phenyl] propionic acid, 7) 2-ethoxy-3- [4- [2-[[1- (2-methoxy-5-pyridyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 8) 2 -Ethoxy-3- [4- [2-[[1- (2-ethoxy-5-pyridyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid; 9) 2-ethoxy-3- [4- [2- [[1- (2-Isopropoxy-5-pyridyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 10) 3- [4- [2-[[1- (2-benzyl) -5-
Pyridyl) ethylidene] amino] oxy] ethoxy] phenyl] -2-ethoxypropionic acid, 11) 2-methoxy-3- [4- [2-[[1- [4-
(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 12) 2-propoxy-3- [4- [2-[[1- [4
-(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 13) 2-isopropoxy-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 14) 2-methylthio-3- [4- [2-[[1- [4
-(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 15) 2-ethylthio-3- [4- [2-[[1- [4
-(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid 16) 2-propylthio-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid 17) 2-phenylthio-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 18) 3- [4- [2-[[1- (4-biphenylyl)]
[Ethylidene] aminooxy] ethoxy] phenyl] -2
-(Phenylamino) propionic acid, 19) 2-phenylamino-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 20) 2-methylamino-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 21) 2-ethylamino-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 22) 2-propylamino-3- [4- [2-[[1-
[4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 23) 2-isopropylamino-3- [4- [2-
[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 24) 2- (N, N-diethylamino) -3- [4-
[2-[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 25) 3- [4- [2-[[1- (4-biphenylyl)]
[Ethylidene] aminooxy] ethoxy] phenyl] -2
-[N-phenyl-N-ethylamino] propionic acid, 26) 3- [4- [2-[[1- (4-biphenylyl)]
[Ethylidene] aminooxy] ethoxy] phenyl] -2
-Pyrrolylpropionic acid, 27) 2- (3-phenylpropyl) -3- [4- [2
-[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 28) 2- (4-phenylbutyl) -3- [4- [2-
[[1- [4- (2-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 29) 2-propyl-3- [4- [2-[[1- [4-
(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 30) 2-butyl-3- [4- [2-[[1- [4-]
(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, or 31) 2-phenoxy-3- [4- [2-[[1- [4
-(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, a phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof is effective. An insulin resistance improving agent contained as a component. 38. The method according to claim 1, wherein 1) 2-ethoxy-3- [4- [2-[[1- (4-biphenylyl) ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 2) 2 -Ethoxy-3- [4- [2-[[1- [4-
(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 3) 2-methylthio-3- [4- [2-[[1- [4-]
(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid 4) 2-phenylthio-3- [4- [2-[[1- [4
-(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 5) 3- [4- [2-[[1- (4-biphenylyl) ethylidene] aminooxy] ethoxy] phenyl] -2 −
(Phenylamino) propionic acid, 6) 2-ethylamino-3- [4- [2-[[1- [4
-(2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid 7) 2- (3-phenylpropyl) -3- [4- [2-
[[1- [4- (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, 8) 2-butyl-3- [4- [2-[[1- [4- (2
-Pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, or 9) 2-phenoxy-3- [4- [2-[[1- [4-
A phenylalkylcarboxylic acid derivative selected from the group consisting of (2-pyridyl) phenyl] ethylidene] aminooxy] ethoxy] phenyl] propionic acid, a pharmacologically acceptable salt thereof and a pharmacologically acceptable ester thereof as an active ingredient. Insulin resistance improving agent contained as a drug. 39. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. Anti-inflammatory agent contained. 40. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. An immunomodulatory agent containing. 41. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. Aldose reductase inhibitor. 42. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. 5-lipoxygenase inhibitor. 43. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. Lipid peroxide production inhibitor. 44. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A PPAR activating agent to be contained. 45. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. An anti-osteoporosis agent containing. 46. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for diabetes containing. 47. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for hyperlipidemia. 48. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for obesity containing. 49. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for glucose intolerance contained therein. 50. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or preventive agent for insulin-resistant non-glucose intolerance, comprising: 51. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for hypertension to contain. 52. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for diabetic complications. 53. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. An agent for treating or preventing arteriosclerosis. 54. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for gestational diabetes to be contained. 55. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. An agent for treating or preventing polycystic ovary syndrome. 56. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for a cardiovascular disease. 57. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for atherosclerosis. 58. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. An agent for treating or preventing cell damage caused by ischemic heart disease. 59. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. An agent for treating or preventing osteoarthritis. 60. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for rheumatoid arthritis. 61. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. An agent for treating or preventing an allergic disease to be contained. 62. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for asthma disease to be contained. 63. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for a cancer disease to be contained. 64. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. An agent for treating or preventing an autoimmune disease to be contained. 65. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. An agent for treating or preventing pancreatitis. 66. A phenylalkylcarboxylic acid derivative, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to claim 1 selected from [claims 1] to [38] as an active ingredient. A therapeutic or prophylactic agent for cataract.